JP2018530571A5 - - Google Patents
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- JP2018530571A5 JP2018530571A5 JP2018518487A JP2018518487A JP2018530571A5 JP 2018530571 A5 JP2018530571 A5 JP 2018530571A5 JP 2018518487 A JP2018518487 A JP 2018518487A JP 2018518487 A JP2018518487 A JP 2018518487A JP 2018530571 A5 JP2018530571 A5 JP 2018530571A5
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazol
- amine
- pyrimidin
- difluoromethyl
- cyclobutyl
- 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.)
- Granted
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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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| KR10-2015-0142014 | 2015-10-12 | ||
| KR20150142014 | 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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| Publication Number | Publication Date |
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| JP2018530571A JP2018530571A (ja) | 2018-10-18 |
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| CN107980040B (zh) | 2015-07-27 | 2021-11-26 | 株式会社钟根堂 | 作为组蛋白去乙酰酶6抑制剂的1,3,4-噁二唑磺酰胺衍生物及含其的医药组合物 |
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2016
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- 2016-10-11 HR HRP20230201TT patent/HRP20230201T1/hr unknown
- 2016-10-11 WO PCT/KR2016/011355 patent/WO2017065473A1/en not_active Ceased
- 2016-10-11 JP JP2018518487A patent/JP6697074B2/ja active Active
- 2016-10-11 DK DK16855690.0T patent/DK3362445T3/da active
- 2016-10-11 NZ NZ740809A patent/NZ740809A/en unknown
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- 2016-10-11 US US15/763,972 patent/US10494355B2/en active Active
- 2016-10-11 ES ES16855690T patent/ES2940413T3/es active Active
- 2016-10-11 HU HUE16855690A patent/HUE061967T2/hu unknown
- 2016-10-11 EP EP16855690.0A patent/EP3362445B1/en active Active
- 2016-10-11 KR KR1020160131245A patent/KR101839137B1/ko active Active
- 2016-10-11 MX MX2018004447A patent/MX384527B/es unknown
- 2016-10-11 RU RU2018117502A patent/RU2695133C1/ru active
- 2016-10-11 FI FIEP16855690.0T patent/FI3362445T3/fi active
- 2016-10-11 CN CN201680072029.8A patent/CN108699048B/zh active Active
- 2016-10-11 CA CA3001666A patent/CA3001666C/en active Active
- 2016-10-11 PL PL16855690.0T patent/PL3362445T3/pl unknown
- 2016-10-11 PT PT168556900T patent/PT3362445T/pt unknown
- 2016-10-12 TW TW105132939A patent/TWI694073B/zh active
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2018
- 2018-04-10 PH PH12018500773A patent/PH12018500773B1/en unknown
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