JP2017501981A5 - - Google Patents
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- Publication number
- JP2017501981A5 JP2017501981A5 JP2016534735A JP2016534735A JP2017501981A5 JP 2017501981 A5 JP2017501981 A5 JP 2017501981A5 JP 2016534735 A JP2016534735 A JP 2016534735A JP 2016534735 A JP2016534735 A JP 2016534735A JP 2017501981 A5 JP2017501981 A5 JP 2017501981A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrazol
- oxadiazol
- amine
- piperidin
- 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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- 150000001875 compounds Chemical class 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 7
- -1 5-phenyloxazol-2-yl Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- TZHAMZFQCRXJQL-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2-phenylethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(CC1=CC=CC=C1)=O)C1=NC(=NO1)C1=CC=CC=C1 TZHAMZFQCRXJQL-UHFFFAOYSA-N 0.000 claims 1
- BGWDTMSGTXYLFQ-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(C)=O)C1=NC(=NO1)C1=CC=CC=C1 BGWDTMSGTXYLFQ-UHFFFAOYSA-N 0.000 claims 1
- LMUXUZFXNUNSIF-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2-phenylethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(CC1=CC=CC=C1)=O)C=1OC(=NN1)C1=C(C=CC=C1Cl)Cl LMUXUZFXNUNSIF-UHFFFAOYSA-N 0.000 claims 1
- JDZXATSSHQQCKE-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-4-methylpentan-1-one Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(CCC(C)C)=O)C=1OC(=NN1)C1=C(C=CC=C1Cl)Cl JDZXATSSHQQCKE-UHFFFAOYSA-N 0.000 claims 1
- YWKNLZNQZUWUJN-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCC(CC1)N1C=C(C=N1)C1=CC(C2=NN=C(O2)C2=C(Cl)C=CC=C2Cl)=C(N)N=C1 YWKNLZNQZUWUJN-UHFFFAOYSA-N 0.000 claims 1
- BEZNVVMPNAFFQH-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)N1CCC(CC1)N1C=C(C=N1)C1=CC(C2=NC=C(O2)C2=CC(Cl)=CC=C2)=C(N)N=C1 BEZNVVMPNAFFQH-UHFFFAOYSA-N 0.000 claims 1
- UDJOVSNJZDGILO-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2-phenylethanone Chemical compound NC1=C(C=C(C=N1)C1=CN(N=C1)C1CCN(CC1)C(=O)CC1=CC=CC=C1)C1=NC=C(O1)C1=CC(Cl)=CC=C1 UDJOVSNJZDGILO-UHFFFAOYSA-N 0.000 claims 1
- NQYVWMHYPZYTJQ-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(C)=O)C=1OC(=CN1)C1=CC(=CC=C1)Cl NQYVWMHYPZYTJQ-UHFFFAOYSA-N 0.000 claims 1
- UTPPMYCLWHXGRC-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2-phenylethanone Chemical compound NC1=C(C=C(C=N1)C1=CN(N=C1)C1CCN(CC1)C(=O)CC1=CC=CC=C1)C1=NC=C(O1)C1=CC=C(Cl)C=C1 UTPPMYCLWHXGRC-UHFFFAOYSA-N 0.000 claims 1
- HJCIOJLLUQLYKS-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCC(CC1)N1C=C(C=N1)C1=CC(C2=NC=C(O2)C2=CC=C(Cl)C=C2)=C(N)N=C1 HJCIOJLLUQLYKS-UHFFFAOYSA-N 0.000 claims 1
- JCTRWHSQGKHHPN-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=NOC(=N1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N JCTRWHSQGKHHPN-UHFFFAOYSA-N 0.000 claims 1
- RXYFHESTJMGSCY-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=NOC(=N1)C=1C(=NC=C(C1)C=1C=NNC1)N RXYFHESTJMGSCY-UHFFFAOYSA-N 0.000 claims 1
- QPDGXWQHCVITNT-UHFFFAOYSA-N 3-(5-benzyl-1,3,4-oxadiazol-2-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(CC2=CC=CC=C2)O1)C1=CN(N=C1)C1CCNCC1 QPDGXWQHCVITNT-UHFFFAOYSA-N 0.000 claims 1
- ANVAZPCRAOPQIJ-UHFFFAOYSA-N 3-(5-phenyl-1,2,4-oxadiazol-3-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NOC(=N1)C1=CC=CC=C1)C1=CN(N=C1)C1CCNCC1 ANVAZPCRAOPQIJ-UHFFFAOYSA-N 0.000 claims 1
- BBAFIJXSLKRXFF-UHFFFAOYSA-N 3-(5-phenyl-1,2,4-oxadiazol-3-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=NC(=NO1)C=1C(=NC=C(C1)C=1C=NNC1)N BBAFIJXSLKRXFF-UHFFFAOYSA-N 0.000 claims 1
- GTVXNXCPIWOXMW-UHFFFAOYSA-N 3-(5-phenyl-1,2-oxazol-3-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=CC(=NO1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N GTVXNXCPIWOXMW-UHFFFAOYSA-N 0.000 claims 1
- OUEYCSALDJJZAE-UHFFFAOYSA-N 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=CC=C1)C1=CN(N=C1)C1CCNCC1 OUEYCSALDJJZAE-UHFFFAOYSA-N 0.000 claims 1
- YEIHOAOJELGJES-UHFFFAOYSA-N 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=CC=C1)C1=CNN=C1 YEIHOAOJELGJES-UHFFFAOYSA-N 0.000 claims 1
- QVQVNNUWZLJWNI-UHFFFAOYSA-N 3-(5-phenyl-1,3-oxazol-2-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N QVQVNNUWZLJWNI-UHFFFAOYSA-N 0.000 claims 1
- HUDJQOWWQNOZMU-UHFFFAOYSA-N 3-(5-phenylfuran-2-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=CC=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N HUDJQOWWQNOZMU-UHFFFAOYSA-N 0.000 claims 1
- HBBFYJYQLLHVLO-UHFFFAOYSA-N 3-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NC(=NO1)C1=C(Cl)C=CC=C1Cl)C1=CN(N=C1)C1CCNCC1 HBBFYJYQLLHVLO-UHFFFAOYSA-N 0.000 claims 1
- QOGFSNMJMBNROD-UHFFFAOYSA-N 3-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]-5-[1-(1-dodecylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound CCCCCCCCCCCCN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NC(=NO1)C1=C(Cl)C=CC=C1Cl QOGFSNMJMBNROD-UHFFFAOYSA-N 0.000 claims 1
- QGXKCALPBVKDSW-UHFFFAOYSA-N 3-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]-5-[1-(1-ethylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound CCN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NC(=NO1)C1=C(Cl)C=CC=C1Cl QGXKCALPBVKDSW-UHFFFAOYSA-N 0.000 claims 1
- VSCOLQXVVSAKLE-UHFFFAOYSA-N 3-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]-5-[1-(oxan-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound ClC1=C(C(=CC=C1)Cl)C1=NOC(=N1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCOCC1)N VSCOLQXVVSAKLE-UHFFFAOYSA-N 0.000 claims 1
- LJZCRZBUFCSJRX-UHFFFAOYSA-N 3-[5-(2,5-dichlorophenyl)-1,2,4-oxadiazol-3-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NOC(=N1)C1=C(Cl)C=CC(Cl)=C1)C1=CN(N=C1)C1CCNCC1 LJZCRZBUFCSJRX-UHFFFAOYSA-N 0.000 claims 1
- HJZZSPZLHHJFGM-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(F)C=CC(F)=C1)C1=CN(N=C1)C1CCNCC1 HJZZSPZLHHJFGM-UHFFFAOYSA-N 0.000 claims 1
- CUCXAKDPZVGKIC-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(F)C=CC(F)=C1)C1=CNN=C1 CUCXAKDPZVGKIC-UHFFFAOYSA-N 0.000 claims 1
- ZCLZKGMBFGLEIJ-UHFFFAOYSA-N 3-[5-(2,6-dichloro-3-fluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(Cl)C(F)=CC=C1Cl)C1=CN(N=C1)C1CCNCC1 ZCLZKGMBFGLEIJ-UHFFFAOYSA-N 0.000 claims 1
- OGNFWOZBNYTNOL-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl)C1=CN(N=C1)C1CCNCC1 OGNFWOZBNYTNOL-UHFFFAOYSA-N 0.000 claims 1
- DKTNXZWSOMKRAN-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1-piperidin-4-ylpyrrol-3-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl)C1=CN(C=C1)C1CCNCC1 DKTNXZWSOMKRAN-UHFFFAOYSA-N 0.000 claims 1
- IMQAWWNWZMSFBP-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1h-pyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C2=CNN=C2)C=C1C(O1)=NN=C1C1=C(Cl)C=CC=C1Cl IMQAWWNWZMSFBP-UHFFFAOYSA-N 0.000 claims 1
- FJLRRTVVKQMQDA-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-[1-(1-dodecylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound CCCCCCCCCCCCN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl FJLRRTVVKQMQDA-UHFFFAOYSA-N 0.000 claims 1
- ZBTBHQRMQLOGTA-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound CN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl ZBTBHQRMQLOGTA-UHFFFAOYSA-N 0.000 claims 1
- LWRKYLRRDIXJHM-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-[1-(oxan-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl)C1=CN(N=C1)C1CCOCC1 LWRKYLRRDIXJHM-UHFFFAOYSA-N 0.000 claims 1
- BMUXXIXZPXPFGC-UHFFFAOYSA-N 3-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]-5-(1-cyclohexylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC=1C=C(C=CC1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCCCC1)N BMUXXIXZPXPFGC-UHFFFAOYSA-N 0.000 claims 1
- RGCPVFHDBYPACT-UHFFFAOYSA-N 3-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC=1C=C(C=CC1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N RGCPVFHDBYPACT-UHFFFAOYSA-N 0.000 claims 1
- WJWSQCJSOYBLLQ-UHFFFAOYSA-N 3-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound ClC=1C=C(C=CC1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCN(CC1)C)N WJWSQCJSOYBLLQ-UHFFFAOYSA-N 0.000 claims 1
- WXZVALFJKXFFRX-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]-5-(1-cyclohexylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCCCC1)N WXZVALFJKXFFRX-UHFFFAOYSA-N 0.000 claims 1
- DIVKPPRZFNTJJY-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N DIVKPPRZFNTJJY-UHFFFAOYSA-N 0.000 claims 1
- NKXDTNWKAQEPET-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCN(CC1)C)N NKXDTNWKAQEPET-UHFFFAOYSA-N 0.000 claims 1
- UIKPZWWGPHOMGP-UHFFFAOYSA-N 3-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=C(F)C=C1)C1=CN(N=C1)C1CCNCC1 UIKPZWWGPHOMGP-UHFFFAOYSA-N 0.000 claims 1
- VMQUDSYSZTXZRK-UHFFFAOYSA-N 3-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=C(F)C=C1)C1=CNN=C1 VMQUDSYSZTXZRK-UHFFFAOYSA-N 0.000 claims 1
- MCFLGOFJLHHIAX-UHFFFAOYSA-N 3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound CC(C)(C)C1=CC=C(C=C1)C1=NN=C(O1)C1=CC(=CN=C1N)C1=CN(N=C1)C1CCNCC1 MCFLGOFJLHHIAX-UHFFFAOYSA-N 0.000 claims 1
- GKHGYSBHZFKTFG-UHFFFAOYSA-N 3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound CC(C)(C)C1=CC=C(C=C1)C1=NN=C(O1)C1=CC(=CN=C1N)C1=CNN=C1 GKHGYSBHZFKTFG-UHFFFAOYSA-N 0.000 claims 1
- JYVSYFGHYFXYBE-UHFFFAOYSA-N 3-[5-(cyclopropylmethyl)-1,3,4-oxadiazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical class NC1=NC=C(C=C1C1=NN=C(CC2CC2)O1)C1=CN(N=C1)C1CCNCC1 JYVSYFGHYFXYBE-UHFFFAOYSA-N 0.000 claims 1
- VZQVQDIGKKUMNO-UHFFFAOYSA-N 5-(1-cyclohexylpyrazol-4-yl)-3-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NC(=NO1)C1=CC=CC=C1)C1=CN(N=C1)C1CCCCC1 VZQVQDIGKKUMNO-UHFFFAOYSA-N 0.000 claims 1
- IJLBAXYWKUBUSP-UHFFFAOYSA-N 5-(1-cyclohexylpyrazol-4-yl)-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NOC(=N1)C1=CC=CC=C1)C1=CN(N=C1)C1CCCCC1 IJLBAXYWKUBUSP-UHFFFAOYSA-N 0.000 claims 1
- XINCQESLKPNWBI-UHFFFAOYSA-N 5-(1-cyclohexylpyrazol-4-yl)-3-(5-phenyl-1,2-oxazol-3-yl)pyridin-2-amine Chemical compound C1(CCCCC1)N1N=CC(=C1)C=1C=C(C(=NC1)N)C1=NOC(=C1)C1=CC=CC=C1 XINCQESLKPNWBI-UHFFFAOYSA-N 0.000 claims 1
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