JP2017501981A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- YNGHSZPXZMUJPU-UHFFFAOYSA-N 5-(1-cyclohexylpyrazol-4-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=CC=C1)C1=CN(N=C1)C1CCCCC1 YNGHSZPXZMUJPU-UHFFFAOYSA-N 0.000 claims 1
- NSNMRJXCOZGSAQ-UHFFFAOYSA-N 5-(1-cyclohexylpyrazol-4-yl)-3-(5-phenylfuran-2-yl)pyridin-2-amine Chemical compound C1(CCCCC1)N1N=CC(=C1)C=1C=C(C(=NC1)N)C=1OC(=CC1)C1=CC=CC=C1 NSNMRJXCOZGSAQ-UHFFFAOYSA-N 0.000 claims 1
- FUCKGKKXLCPNQH-UHFFFAOYSA-N 5-(1-cyclohexylpyrazol-4-yl)-3-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NC(=NO1)C1=C(Cl)C=CC=C1Cl)C1=CN(N=C1)C1CCCCC1 FUCKGKKXLCPNQH-UHFFFAOYSA-N 0.000 claims 1
- QMLYOFTXXIEGFQ-UHFFFAOYSA-N 5-(1-cyclohexylpyrazol-4-yl)-3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl)C1=CN(N=C1)C1CCCCC1 QMLYOFTXXIEGFQ-UHFFFAOYSA-N 0.000 claims 1
- ZLVSUDOVHNJOJX-UHFFFAOYSA-N 5-(1-piperidin-4-ylpyrazol-4-yl)-3-(5-pyrazin-2-yl-1,3,4-oxadiazol-2-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CN=CC=N1)C1=CN(N=C1)C1CCNCC1 ZLVSUDOVHNJOJX-UHFFFAOYSA-N 0.000 claims 1
- NKJFEMLLHDYMTM-UHFFFAOYSA-N 5-(1-piperidin-4-ylpyrazol-4-yl)-3-(5-pyridin-2-yl-1,3,4-oxadiazol-2-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=NC=CC=C1)C1=CN(N=C1)C1CCNCC1 NKJFEMLLHDYMTM-UHFFFAOYSA-N 0.000 claims 1
- OSXWFYLTVRKXLB-UHFFFAOYSA-N 5-(1-piperidin-4-ylpyrazol-4-yl)-3-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=CN=C1)C1=CN(N=C1)C1CCNCC1 OSXWFYLTVRKXLB-UHFFFAOYSA-N 0.000 claims 1
- AUTCDZNPLXPORG-UHFFFAOYSA-N 5-(1-piperidin-4-ylpyrazol-4-yl)-3-(5-pyridin-3-yl-1,3-oxazol-2-yl)pyridin-2-amine Chemical compound N1CCC(CC1)N1N=CC(=C1)C=1C=C(C(=NC1)N)C=1OC(=CN1)C=1C=NC=CC1 AUTCDZNPLXPORG-UHFFFAOYSA-N 0.000 claims 1
- CFHBHAREIOQQCM-UHFFFAOYSA-N 5-(1-piperidin-4-ylpyrazol-4-yl)-3-[5-(1,3-thiazol-2-yl)-1,3,4-oxadiazol-2-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=NC=CS1)C1=CN(N=C1)C1CCNCC1 CFHBHAREIOQQCM-UHFFFAOYSA-N 0.000 claims 1
- RGWJDOSCIYCLMZ-UHFFFAOYSA-N 5-(1-piperidin-4-ylpyrazol-4-yl)-3-[5-[4-(trifluoromethyl)-1,3-thiazol-2-yl]-1,3,4-oxadiazol-2-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=NC(=CS1)C(F)(F)F)C1=CN(N=C1)C1CCNCC1 RGWJDOSCIYCLMZ-UHFFFAOYSA-N 0.000 claims 1
- OABOFXQLOAGHIV-UHFFFAOYSA-N 5-[1-(1-ethylpiperidin-4-yl)pyrazol-4-yl]-3-(5-phenyl-1,3-oxazol-2-yl)pyridin-2-amine Chemical compound C(C)N1CCC(CC1)N1N=CC(=C1)C=1C=C(C(=NC1)N)C=1OC(=CN1)C1=CC=CC=C1 OABOFXQLOAGHIV-UHFFFAOYSA-N 0.000 claims 1
- WTCGJXUAFGJEPJ-UHFFFAOYSA-N 5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]-3-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-2-amine Chemical class CN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NC(=NO1)C1=CC=CC=C1 WTCGJXUAFGJEPJ-UHFFFAOYSA-N 0.000 claims 1
- NASVYGPSNNCSLJ-UHFFFAOYSA-N 5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyridin-2-amine Chemical class CN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NOC(=N1)C1=CC=CC=C1 NASVYGPSNNCSLJ-UHFFFAOYSA-N 0.000 claims 1
- IFTFQTYDMRQJNF-UHFFFAOYSA-N 5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]-3-(5-phenyl-1,2-oxazol-3-yl)pyridin-2-amine Chemical compound CN1CCC(CC1)N1N=CC(=C1)C=1C=C(C(=NC1)N)C1=NOC(=C1)C1=CC=CC=C1 IFTFQTYDMRQJNF-UHFFFAOYSA-N 0.000 claims 1
- AMLUBOSNOTVUMY-UHFFFAOYSA-N 5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]-3-(5-phenylfuran-2-yl)pyridin-2-amine Chemical compound CN1CCC(CC1)N1N=CC(=C1)C=1C=C(C(=NC1)N)C=1OC(=CC1)C1=CC=CC=C1 AMLUBOSNOTVUMY-UHFFFAOYSA-N 0.000 claims 1
- WHQOMJWLBMZZDH-UHFFFAOYSA-N 5-[1-(oxan-4-yl)pyrazol-4-yl]-3-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-2-amine Chemical class NC1=NC=C(C=C1C1=NC(=NO1)C1=CC=CC=C1)C1=CN(N=C1)C1CCOCC1 WHQOMJWLBMZZDH-UHFFFAOYSA-N 0.000 claims 1
- NDHRUYJCMQIAIN-UHFFFAOYSA-N 5-[1-(oxan-4-yl)pyrazol-4-yl]-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyridin-2-amine Chemical class NC1=NC=C(C=C1C1=NOC(=N1)C1=CC=CC=C1)C1=CN(N=C1)C1CCOCC1 NDHRUYJCMQIAIN-UHFFFAOYSA-N 0.000 claims 1
- HJRCLFOGOWNDNS-UHFFFAOYSA-N 5-[1-(oxan-4-yl)pyrazol-4-yl]-3-(5-phenyl-1,2-oxazol-3-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=CC(=NO1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCOCC1)N HJRCLFOGOWNDNS-UHFFFAOYSA-N 0.000 claims 1
- IKJNBPBLHLFGQM-UHFFFAOYSA-N 5-[1-(oxan-4-yl)pyrazol-4-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-amine Chemical class NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=CC=C1)C1=CN(N=C1)C1CCOCC1 IKJNBPBLHLFGQM-UHFFFAOYSA-N 0.000 claims 1
- GDVFZYDOIBDCCA-UHFFFAOYSA-N 5-[1-(oxan-4-yl)pyrazol-4-yl]-3-(5-phenylfuran-2-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=CC=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCOCC1)N GDVFZYDOIBDCCA-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- UOWPSVOKDAOBCP-UHFFFAOYSA-N C(C)N1CCC(CC1)N1N=CC(=C1)C=1C=C(C(=NC=1)N)C1=NC(=NO1)C1=CC=CC=C1 Chemical class C(C)N1CCC(CC1)N1N=CC(=C1)C=1C=C(C(=NC=1)N)C1=NC(=NO1)C1=CC=CC=C1 UOWPSVOKDAOBCP-UHFFFAOYSA-N 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- OGFCSEPSMQGHLO-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)C1=NN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCN(CC1)CC)N Chemical compound ClC1=C(C(=CC=C1)Cl)C1=NN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCN(CC1)CC)N OGFCSEPSMQGHLO-UHFFFAOYSA-N 0.000 claims 1
- DJEGJYBUVIDGJW-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)C1=NOC(=N1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCN(CC1)C)N Chemical compound ClC1=C(C(=CC=C1)Cl)C1=NOC(=N1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCN(CC1)C)N DJEGJYBUVIDGJW-UHFFFAOYSA-N 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- PMWFLUQQAYVKTR-UHFFFAOYSA-N [4-[4-[6-amino-5-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-cyclopropylmethanone Chemical compound NC1=C(C=C(C=N1)C1=CN(N=C1)C1CCN(CC1)C(=O)C1CC1)C1=NC(=NO1)C1=CC=CC=C1 PMWFLUQQAYVKTR-UHFFFAOYSA-N 0.000 claims 1
- QBSPROMUWIVLTB-UHFFFAOYSA-N [4-[4-[6-amino-5-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-phenylmethanone Chemical compound NC1=C(C=C(C=N1)C1=CN(N=C1)C1CCN(CC1)C(=O)C1=CC=CC=C1)C1=NC(=NO1)C1=CC=CC=C1 QBSPROMUWIVLTB-UHFFFAOYSA-N 0.000 claims 1
- PUDFRLNKEKFHME-UHFFFAOYSA-N [4-[4-[6-amino-5-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-cyclopropylmethanone Chemical compound NC1=C(C=C(C=N1)C1=CN(N=C1)C1CCN(CC1)C(=O)C1CC1)C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl PUDFRLNKEKFHME-UHFFFAOYSA-N 0.000 claims 1
- PKBOAJABLLVLPJ-UHFFFAOYSA-N [4-[4-[6-amino-5-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-phenylmethanone Chemical compound NC1=C(C=C(C=N1)C1=CN(N=C1)C1CCN(CC1)C(=O)C1=CC=CC=C1)C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl PKBOAJABLLVLPJ-UHFFFAOYSA-N 0.000 claims 1
- KAELERLRUYCVFV-UHFFFAOYSA-N [4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(=O)C1=CC=C(C=C1)F)C=1OC(=CN1)C1=CC(=CC=C1)Cl KAELERLRUYCVFV-UHFFFAOYSA-N 0.000 claims 1
- INVUEKMKVZWSBL-UHFFFAOYSA-N [4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-cyclopropylmethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(=O)C1CC1)C=1OC(=CN1)C1=CC(=CC=C1)Cl INVUEKMKVZWSBL-UHFFFAOYSA-N 0.000 claims 1
- HEQNRLHOUUPPFC-UHFFFAOYSA-N [4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-phenylmethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(=O)C1=CC=CC=C1)C=1OC(=CN1)C1=CC(=CC=C1)Cl HEQNRLHOUUPPFC-UHFFFAOYSA-N 0.000 claims 1
- ZUVNHGCFQSYRDK-UHFFFAOYSA-N [4-[4-[6-amino-5-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-cyclopropylmethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(=O)C1CC1)C=1OC(=CN1)C1=CC=C(C=C1)Cl ZUVNHGCFQSYRDK-UHFFFAOYSA-N 0.000 claims 1
- SXTXSDDIYPYIRU-UHFFFAOYSA-N [4-[4-[6-amino-5-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-phenylmethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(=O)C1=CC=CC=C1)C=1OC(=CN1)C1=CC=C(C=C1)Cl SXTXSDDIYPYIRU-UHFFFAOYSA-N 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 0 Cc1c(*)c(ICC*)c(*)nc1N Chemical compound Cc1c(*)c(ICC*)c(*)nc1N 0.000 description 14
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361909830P | 2013-11-27 | 2013-11-27 | |
| US201361909828P | 2013-11-27 | 2013-11-27 | |
| US61/909,828 | 2013-11-27 | ||
| US61/909,830 | 2013-11-27 | ||
| PCT/US2014/067709 WO2015081257A2 (en) | 2013-11-27 | 2014-11-26 | Aminopyridine derivatives as tam family kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017501981A JP2017501981A (ja) | 2017-01-19 |
| JP2017501981A5 true JP2017501981A5 (enExample) | 2017-11-16 |
| JP6496731B2 JP6496731B2 (ja) | 2019-04-03 |
Family
ID=52146717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016534735A Active JP6496731B2 (ja) | 2013-11-27 | 2014-11-26 | Ｔａｍファミリーキナーゼ阻害剤としてのアミノピリジン誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US10233176B2 (enExample) |
| EP (1) | EP3074390B1 (enExample) |
| JP (1) | JP6496731B2 (enExample) |
| KR (1) | KR102398473B1 (enExample) |
| CN (2) | CN105764514B (enExample) |
| AU (1) | AU2014354711B2 (enExample) |
| BR (1) | BR112016012146B1 (enExample) |
| CA (1) | CA2930324C (enExample) |
| IL (1) | IL245660B (enExample) |
| MX (2) | MX373365B (enExample) |
| WO (1) | WO2015081257A2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
| WO2019060693A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES THEREOF |
| AU2018338314B2 (en) | 2017-09-22 | 2024-12-12 | Kymera Therapeutics, Inc | Protein degraders and uses thereof |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| EP3737666A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | PROTEIN DEGRADATION AGENTS AND ASSOCIATED USES |
| EP3737675A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| WO2020010210A1 (en) * | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Mertk degraders and uses thereof |
| EP3817748A4 (en) | 2018-07-06 | 2022-08-24 | Kymera Therapeutics, Inc. | TRICYCLIC CRBN LIGANDS AND USES THEREOF |
| WO2020010227A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| BR112021005054A2 (pt) * | 2018-09-18 | 2021-06-08 | Signalchem Lifesciences Corporation | terapia de combinação para tratamento contra câncer no sangue |
| SG11202105424PA (en) | 2018-11-30 | 2021-06-29 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| US12521438B2 (en) | 2019-06-10 | 2026-01-13 | Kymera Therapeutics, Inc. | SMARCA degraders and uses thereof |
| JP2023509366A (ja) | 2019-12-17 | 2023-03-08 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| WO2021127283A2 (en) | 2019-12-17 | 2021-06-24 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| PH12022551522A1 (en) | 2019-12-23 | 2024-01-29 | Kymera Therapeutics Inc | Smarca degraders and uses thereof |
| PH12022552458A1 (en) | 2020-03-19 | 2024-01-22 | Kymera Therapeutics Inc | Mdm2 degraders and uses thereof |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| CN112707898A (zh) * | 2020-12-21 | 2021-04-27 | 徐新杰 | 一种杂芳基取代的吡嗪衍生物及其应用 |
| MX2023007852A (es) | 2020-12-30 | 2023-07-07 | Kymera Therapeutics Inc | Degradadores de cinasas asociadas al receptor de interleucina-1 (irak) y usos de los mismos. |
| EP4284368B1 (en) * | 2021-02-01 | 2024-12-11 | SignalChem Lifesciences Corporation | Use of the axl inhibitor slc-391 as antiviral therapeutic agent |
| WO2022174268A1 (en) | 2021-02-15 | 2022-08-18 | Kymera Therapeutics, Inc. | Irak4 degraders and uses thereof |
| AU2022271290A1 (en) | 2021-05-07 | 2023-11-23 | Kymera Therapeutics, Inc. | Cdk2 degraders and uses thereof |
| WO2023076556A1 (en) | 2021-10-29 | 2023-05-04 | Kymera Therapeutics, Inc. | Irak4 degraders and synthesis thereof |
| IL314437A (en) | 2022-01-31 | 2024-09-01 | Kymera Therapeutics Inc | IRAK joints and their uses |
| WO2025170888A1 (en) | 2024-02-05 | 2025-08-14 | Signalchem Lifesciences Corporation | A combination of the axl inhibitor slc-391 and a pd-1 inhibitor for use in the treatment of blood cancer |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7884119B2 (en) | 2005-09-07 | 2011-02-08 | Rigel Pharmaceuticals, Inc. | Triazole derivatives useful as Axl inhibitors |
| PE20070978A1 (es) | 2006-02-14 | 2007-11-15 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE FOSFATIDILINOSITOL 3-QUINASAS (PI3Ks) |
| CA2646701A1 (en) * | 2006-03-22 | 2007-10-04 | Vertex Pharmaceuticals Incorporated | C-met protein kinase inhibitors for the treatment of proliferative disorders |
| EP1900727A1 (en) | 2006-08-30 | 2008-03-19 | Cellzome Ag | Aminopyridine derivatives as kinase inhibitors |
| WO2008045978A1 (en) | 2006-10-10 | 2008-04-17 | Rigel Pharmaceuticals, Inc. | Pinane-substituted pyrimidinediamine derivatives useful as axl inhibitors |
| US7879856B2 (en) | 2006-12-22 | 2011-02-01 | Rigel Pharmaceuticals, Inc. | Diaminothiazoles useful as Axl inhibitors |
| PT2078010E (pt) | 2006-12-29 | 2014-05-07 | Rigel Pharmaceuticals Inc | Triazoles substituídos com heteroarilos policíclicos úteis como inibidores de axl |
| EP2484679B1 (en) | 2006-12-29 | 2016-09-28 | Rigel Pharmaceuticals, Inc. | N3-heteroaryl substituted triazoles and n5-heteroaryl substitued triazoles useful as axl inhibitors |
| EP2114954B1 (en) | 2006-12-29 | 2013-02-13 | Rigel Pharmaceuticals, Inc. | Bicyclic aryl and bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2710230C (en) | 2006-12-29 | 2016-02-23 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic aryl and bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| EP2079736B1 (en) | 2006-12-29 | 2017-10-18 | Rigel Pharmaceuticals, Inc. | Substituted triazoles useful as axl inhibitors |
| AU2008240188A1 (en) | 2007-04-13 | 2008-10-23 | Supergen, Inc. | Axl kinase inhibitors useful for the treatment of cancer or hyperproliferative disorders |
| PE20090717A1 (es) * | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| GB0713259D0 (en) | 2007-07-09 | 2007-08-15 | Astrazeneca Ab | Pyrazine derivatives 954 |
| WO2009024825A1 (en) | 2007-08-21 | 2009-02-26 | Astrazeneca Ab | 2-pyrazinylbenzimidazole derivatives as receptor tyrosine kinase inhibitors |
| GB0719803D0 (en) | 2007-10-10 | 2007-11-21 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| CA2703653A1 (en) | 2007-10-25 | 2009-04-30 | Astrazeneca Ab | Pyridine and pyrazine derivatives -083 |
| JP5635909B2 (ja) | 2007-10-26 | 2014-12-03 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ａｘｌ阻害剤として有用な多環アリール置換トリアゾール及び多環ヘテロアリール置換トリアゾール |
| WO2009099982A1 (en) * | 2008-02-04 | 2009-08-13 | Osi Pharmaceuticals, Inc. | 2-aminopyridine kinase inhibitors |
| CA2716949A1 (en) | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | N- (6-aminopyridin-3-yl) -3- (sulfonamido) benzamide derivatives as b-raf inhibitors for the treatment of cancer |
| JP5746015B2 (ja) | 2008-04-16 | 2015-07-08 | マックス プランク ゲゼルシャフト ツゥアー フェデルゥン デル ヴィッセンシャフテン エー フォー | Ａｘｌキナーゼ阻害剤としてのキノリン誘導体 |
| US8349838B2 (en) | 2008-07-09 | 2013-01-08 | Rigel Pharmaceuticals, Inc. | Polycyclic heteroaryl substituted triazoles useful as Axl inhibitors |
| SI2328888T1 (sl) * | 2008-07-09 | 2013-03-29 | Rigel Pharmaceuticals, Inc. | Premoščeni biciklični heteroaril substituirani triazoli, uporabni kot inhibitorji Axl |
| BRPI1007046B1 (pt) | 2009-01-16 | 2019-07-16 | Rigel Pharmaceuticals, Inc. | Inibidores axl para uso em terapia de combinação para evitar, tratar ou controlar o câncer metastático. |
| WO2010090764A1 (en) | 2009-02-09 | 2010-08-12 | Supergen, Inc. | Pyrrolopyrimidinyl axl kinase inhibitors |
| EP2311809A1 (en) | 2009-10-16 | 2011-04-20 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Quinolinyloxyphenylsulfonamides |
| JP5675850B2 (ja) * | 2010-02-05 | 2015-02-25 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ヘタリール−［１，８］ナフチリジン誘導体 |
| WO2011138751A2 (en) | 2010-05-04 | 2011-11-10 | Pfizer Inc. | Heterocyclic derivatives as alk inhibitors |
| AU2011253021A1 (en) * | 2010-05-12 | 2012-11-29 | Vertex Pharmaceuticals Incorporated | 2 -aminopyridine derivatives useful as inhibitors of ATR kinase |
| EP2423208A1 (en) | 2010-08-28 | 2012-02-29 | Lead Discovery Center GmbH | Pharmaceutically active compounds as Axl inhibitors |
| WO2012087938A1 (en) * | 2010-12-20 | 2012-06-28 | Glaxosmithkline Llc | Quinazolinone derivatives as antiviral agents |
| ES2759615T3 (es) | 2011-04-01 | 2020-05-11 | Univ Utah Res Found | Análogos de N-fenilpirimidina-2-amina sustituidos como inhibidores de la quinasa AXL |
| DK2780338T3 (en) | 2011-11-14 | 2016-12-19 | Ignyta Inc | Uracil AS AXL- AND C-MET kinase inhibitors |
| CA2863515C (en) | 2012-01-31 | 2018-02-27 | Daiichi Sankyo Company, Limited | Pyridone derivatives |
| WO2013162061A1 (ja) | 2012-04-26 | 2013-10-31 | 第一三共株式会社 | 二環性ピリミジン化合物 |
| CN104903311B (zh) * | 2013-01-02 | 2016-11-09 | H.隆德贝克有限公司 | 作为lrrk2抑制剂的氨基吡啶衍生的化合物 |
-
2014
- 2014-11-26 CN CN201480065032.8A patent/CN105764514B/zh active Active
- 2014-11-26 MX MX2016006815A patent/MX373365B/es active IP Right Grant
- 2014-11-26 JP JP2016534735A patent/JP6496731B2/ja active Active
- 2014-11-26 US US15/039,609 patent/US10233176B2/en active Active
- 2014-11-26 CA CA2930324A patent/CA2930324C/en active Active
- 2014-11-26 EP EP14819178.6A patent/EP3074390B1/en active Active
- 2014-11-26 WO PCT/US2014/067709 patent/WO2015081257A2/en not_active Ceased
- 2014-11-26 KR KR1020167016444A patent/KR102398473B1/ko active Active
- 2014-11-26 AU AU2014354711A patent/AU2014354711B2/en active Active
- 2014-11-26 CN CN201910548630.5A patent/CN110156770B/zh active Active
- 2014-11-26 BR BR112016012146-5A patent/BR112016012146B1/pt active IP Right Grant
-
2016
- 2016-05-16 IL IL245660A patent/IL245660B/en active IP Right Grant
- 2016-05-25 MX MX2020005181A patent/MX2020005181A/es unknown
-
2019
- 2019-01-22 US US16/254,208 patent/US10723725B2/en active Active
-
2020
- 2020-06-11 US US16/899,494 patent/US11034686B2/en active Active
- 2020-06-11 US US16/899,489 patent/US11034685B2/en active Active