JP2009525960A5 - - Google Patents
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- Publication number
- JP2009525960A5 JP2009525960A5 JP2008551297A JP2008551297A JP2009525960A5 JP 2009525960 A5 JP2009525960 A5 JP 2009525960A5 JP 2008551297 A JP2008551297 A JP 2008551297A JP 2008551297 A JP2008551297 A JP 2008551297A JP 2009525960 A5 JP2009525960 A5 JP 2009525960A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- thiazol
- alkyl
- phenyl
- trifluoromethyl
- 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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- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 76
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 32
- 125000001072 heteroaryl group Chemical group 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- RUQPVADMLMMXDR-IBGZPJMESA-N (2s)-1-n-(5-isoquinolin-6-yl-1,3-thiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 RUQPVADMLMMXDR-IBGZPJMESA-N 0.000 claims 1
- ONHHLCOLUPUJHO-DEOSSOPVSA-N (2s)-1-n-(5-isoquinolin-6-yl-4-phenyl-1,3-thiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](N)CC=1C=CC(=CC=1)C(F)(F)F)NC(SC=1C=2C=C3C=CN=CC3=CC=2)=NC=1C1=CC=CC=C1 ONHHLCOLUPUJHO-DEOSSOPVSA-N 0.000 claims 1
- PRXJKVDDVOWRHR-SFHVURJKSA-N (2s)-1-n-(5-phthalazin-6-yl-1,3-thiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=NN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 PRXJKVDDVOWRHR-SFHVURJKSA-N 0.000 claims 1
- VGRYHOBWAAWMSO-NRFANRHFSA-N (2s)-1-n-[4-(furan-2-yl)-5-isoquinolin-6-yl-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](N)CC=1C=CC(=CC=1)C(F)(F)F)NC(SC=1C=2C=C3C=CN=CC3=CC=2)=NC=1C1=CC=CO1 VGRYHOBWAAWMSO-NRFANRHFSA-N 0.000 claims 1
- OTYWCJLDOQPLSL-KRWDZBQOSA-N (2s)-1-n-[4-(methoxymethyl)-5-(1,6-naphthyridin-2-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical class C([C@H](N)CNC1=NC(=C(S1)C=1N=C2C=CN=CC2=CC=1)COC)C1=CC=C(C(F)(F)F)C=C1 OTYWCJLDOQPLSL-KRWDZBQOSA-N 0.000 claims 1
- BOQHAWYNJHNJKM-KRWDZBQOSA-N (2s)-1-n-[4-(methoxymethyl)-5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C(C)=NNC2=CC=1)COC)C1=CC=C(C(F)(F)F)C=C1 BOQHAWYNJHNJKM-KRWDZBQOSA-N 0.000 claims 1
- WFNHFDUUHUGBIS-FQEVSTJZSA-N (2s)-1-n-[4-(methoxymethyl)-5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3-thiazol-2-yl]-2-n-(2-morpholin-4-ylethyl)-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC1=NC(=C(S1)C=1SC2=CN=CC=C2N=1)COC)NCCN1CCOCC1)C1=CC=C(C(F)(F)F)C=C1 WFNHFDUUHUGBIS-FQEVSTJZSA-N 0.000 claims 1
- QNPXGYWAPZLUDI-AWEZNQCLSA-N (2s)-1-n-[4-(methoxymethyl)-5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1SC2=CN=CC=C2N=1)COC)C1=CC=C(C(F)(F)F)C=C1 QNPXGYWAPZLUDI-AWEZNQCLSA-N 0.000 claims 1
- IUFSFRMTTMOBER-KRWDZBQOSA-N (2s)-1-n-[4-methyl-5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-2-yl]-3-phenylpropane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C(C)=NNC2=CC=1)C)C1=CC=CC=C1 IUFSFRMTTMOBER-KRWDZBQOSA-N 0.000 claims 1
- KMDQAOCMEQUOAQ-INIZCTEOSA-N (2s)-1-n-[5-(1,6-naphthyridin-2-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1N=C2C=CN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 KMDQAOCMEQUOAQ-INIZCTEOSA-N 0.000 claims 1
- MPLUPNJRXQZQLR-KRWDZBQOSA-N (2s)-1-n-[5-(1h-indazol-5-yl)-4-(methoxymethyl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C=NNC2=CC=1)COC)C1=CC=C(C(F)(F)F)C=C1 MPLUPNJRXQZQLR-KRWDZBQOSA-N 0.000 claims 1
- BMLQBUZLVZOSBO-KRWDZBQOSA-N (2s)-1-n-[5-(1h-indazol-5-yl)-4-methyl-1,3-thiazol-2-yl]-3-phenylpropane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C=NNC2=CC=1)C)C1=CC=CC=C1 BMLQBUZLVZOSBO-KRWDZBQOSA-N 0.000 claims 1
- SXMJEDMPDDTFKV-INIZCTEOSA-N (2s)-1-n-[5-(1h-indazol-6-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2NN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 SXMJEDMPDDTFKV-INIZCTEOSA-N 0.000 claims 1
- SXZYABNLROKYBA-AWEZNQCLSA-N (2s)-1-n-[5-(3-amino-1,2-benzoxazol-5-yl)-1,3-thiazol-2-yl]-3-(1h-indol-3-yl)propane-1,2-diamine Chemical compound C1=CC=C2C(C[C@@H](CNC=3SC(=CN=3)C=3C=C4C(N)=NOC4=CC=3)N)=CNC2=C1 SXZYABNLROKYBA-AWEZNQCLSA-N 0.000 claims 1
- VWWGPEDOUGDOMJ-AWEZNQCLSA-N (2s)-1-n-[5-(3-amino-1,2-benzoxazol-5-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C(N)=NOC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 VWWGPEDOUGDOMJ-AWEZNQCLSA-N 0.000 claims 1
- HUZSZGBYKRTSEZ-HNNXBMFYSA-N (2s)-1-n-[5-(3-amino-1-methylindazol-6-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC=C(S1)C1=CC=C2C(N)=NN(C2=C1)C)C1=CC=C(C(F)(F)F)C=C1 HUZSZGBYKRTSEZ-HNNXBMFYSA-N 0.000 claims 1
- ZOEZQOZTOFGURN-AWEZNQCLSA-N (2s)-1-n-[5-(3-amino-1h-indazol-5-yl)-1,3-thiazol-2-yl]-3-(1h-indol-3-yl)propane-1,2-diamine Chemical compound C1=CC=C2C(C[C@@H](CNC=3SC(=CN=3)C=3C=C4C(N)=NNC4=CC=3)N)=CNC2=C1 ZOEZQOZTOFGURN-AWEZNQCLSA-N 0.000 claims 1
- FTDNCBJDYUWTID-AWEZNQCLSA-N (2s)-1-n-[5-(3-amino-1h-indazol-5-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C(N)=NNC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 FTDNCBJDYUWTID-AWEZNQCLSA-N 0.000 claims 1
- IEPJGUFCFUXIJJ-AWEZNQCLSA-N (2s)-1-n-[5-(3-amino-1h-indazol-6-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2NN=C(N)C2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 IEPJGUFCFUXIJJ-AWEZNQCLSA-N 0.000 claims 1
- GNXNUXBMLLVKCC-SFHVURJKSA-N (2s)-1-n-[5-(3-aminoisoquinolin-6-yl)-1,3-thiazol-2-yl]-3-(4-chlorophenyl)propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=C(N)N=CC2=CC=1)N)C1=CC=C(Cl)C=C1 GNXNUXBMLLVKCC-SFHVURJKSA-N 0.000 claims 1
- XLMDNKMMDBSPSJ-SFHVURJKSA-N (2s)-1-n-[5-(3-aminoisoquinolin-6-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=C(N)N=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 XLMDNKMMDBSPSJ-SFHVURJKSA-N 0.000 claims 1
- TYCJPDLIEVIZMC-INIZCTEOSA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-2-yl]-3-phenylpropane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC=C1 TYCJPDLIEVIZMC-INIZCTEOSA-N 0.000 claims 1
- AWXUWXYPLGCSOO-ZDUSSCGKSA-N (2s)-1-n-[5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3-thiazol-2-yl]-3-[3-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1SC2=CN=CC=C2N=1)N)C1=CC=CC(C(F)(F)F)=C1 AWXUWXYPLGCSOO-ZDUSSCGKSA-N 0.000 claims 1
- WBWWEGGTYJUJIS-ZDUSSCGKSA-N (2s)-1-n-[5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1SC2=CN=CC=C2N=1)N)C1=CC=C(C(F)(F)F)C=C1 WBWWEGGTYJUJIS-ZDUSSCGKSA-N 0.000 claims 1
- RREBSXDCHJHRDT-FXMQYSIJSA-N (2s)-1-n-[5-isoquinolin-6-yl-4-(1-methoxyethyl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C=CN=CC2=CC=1)C(C)OC)C1=CC=C(C(F)(F)F)C=C1 RREBSXDCHJHRDT-FXMQYSIJSA-N 0.000 claims 1
- OZEQEZSPZCUFMW-FQEVSTJZSA-N (2s)-1-n-[5-isoquinolin-6-yl-4-(methoxymethyl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C=CN=CC2=CC=1)COC)C1=CC=C(C(F)(F)F)C=C1 OZEQEZSPZCUFMW-FQEVSTJZSA-N 0.000 claims 1
- LVKPDCDJLJWKLG-FQEVSTJZSA-N (2s)-1-n-[5-isoquinolin-6-yl-4-(methylaminomethyl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C=CN=CC2=CC=1)CNC)C1=CC=C(C(F)(F)F)C=C1 LVKPDCDJLJWKLG-FQEVSTJZSA-N 0.000 claims 1
- BLAVYYFRUYHSSA-IBGZPJMESA-N (2s)-3-(1h-indol-3-yl)-1-n-(5-isoquinolin-6-yl-1,3-thiazol-2-yl)propane-1,2-diamine Chemical compound C1=CC=C2C(C[C@@H](CNC=3SC(=CN=3)C=3C=C4C=CN=CC4=CC=3)N)=CNC2=C1 BLAVYYFRUYHSSA-IBGZPJMESA-N 0.000 claims 1
- GNUDIMYDTZMJQX-AWEZNQCLSA-N (2s)-3-(1h-indol-3-yl)-1-n-[4-(methoxymethyl)-5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C1=NC=C2SC(C=3SC(NC[C@@H](N)CC=4C5=CC=CC=C5NC=4)=NC=3COC)=NC2=C1 GNUDIMYDTZMJQX-AWEZNQCLSA-N 0.000 claims 1
- RUAXRQMFJHIYOD-INIZCTEOSA-N (2s)-3-(1h-indol-3-yl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C1=CC=C2C(C[C@H](N)CNC3=NC=C(S3)C3=CC=C4NN=C(C4=C3)C)=CNC2=C1 RUAXRQMFJHIYOD-INIZCTEOSA-N 0.000 claims 1
- YYJTVOXCOOYFNN-HNNXBMFYSA-N (2s)-3-(1h-indol-3-yl)-1-n-[5-[3-(methylamino)-1h-indazol-5-yl]-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C1=CC=C2C(C[C@H](N)CNC3=NC=C(S3)C3=CC=C4NN=C(C4=C3)NC)=CNC2=C1 YYJTVOXCOOYFNN-HNNXBMFYSA-N 0.000 claims 1
- VGPQUILKMXOHDS-IBGZPJMESA-N (2s)-3-(3-chlorophenyl)-1-n-(5-isoquinolin-6-yl-1,3-thiazol-2-yl)propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=CC(Cl)=C1 VGPQUILKMXOHDS-IBGZPJMESA-N 0.000 claims 1
- SVFHQJXKRMSPEU-AWEZNQCLSA-N (2s)-3-(3-chlorophenyl)-1-n-[4-(methoxymethyl)-5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1SC2=CN=CC=C2N=1)COC)C1=CC=CC(Cl)=C1 SVFHQJXKRMSPEU-AWEZNQCLSA-N 0.000 claims 1
- OLXOCLWPQPPADC-AWEZNQCLSA-N (2s)-3-(3-chlorophenyl)-1-n-[5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-4-(2,2,2-trifluoroethoxymethyl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=C(COCC(F)(F)F)N=1)C=1SC2=CN=CC=C2N=1)N)C1=CC=CC(Cl)=C1 OLXOCLWPQPPADC-AWEZNQCLSA-N 0.000 claims 1
- CSYSTVVLDFRCMG-HNNXBMFYSA-N (2s)-3-(4-chlorophenyl)-1-n-[4-(ethoxymethyl)-5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1SC2=CN=CC=C2N=1)COCC)C1=CC=C(Cl)C=C1 CSYSTVVLDFRCMG-HNNXBMFYSA-N 0.000 claims 1
- AIBWDDHRUDOEOF-AWEZNQCLSA-N (2s)-3-(4-chlorophenyl)-1-n-[4-(methoxymethyl)-5-([1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1SC2=CN=CC=C2N=1)COC)C1=CC=C(Cl)C=C1 AIBWDDHRUDOEOF-AWEZNQCLSA-N 0.000 claims 1
- LJVIDZQPGQAVHM-INIZCTEOSA-N (2s)-3-(4-chlorophenyl)-1-n-[5-(1h-indazol-5-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=C(Cl)C=C1 LJVIDZQPGQAVHM-INIZCTEOSA-N 0.000 claims 1
- XJADBOIGESUADD-INIZCTEOSA-N (2s)-3-(4-chlorophenyl)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(Cl)C=C1 XJADBOIGESUADD-INIZCTEOSA-N 0.000 claims 1
- CQLSDNLEPHKRAL-IFFNBQHOSA-N (3E)-5-[2-[[(2S)-2-amino-3-(1H-indol-3-yl)propyl]amino]-1,3-thiazol-5-yl]-3-(furan-2-ylmethylidene)-1H-indol-2-one 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C([C@@H](N)CC=1C2=CC=CC=C2NC=1)NC(S1)=NC=C1C(C=C12)=CC=C1NC(=O)\C2=C\C1=CC=CO1 CQLSDNLEPHKRAL-IFFNBQHOSA-N 0.000 claims 1
- CQLSDNLEPHKRAL-ZHMVQQCMSA-N (3Z)-5-[2-[[(2S)-2-amino-3-(1H-indol-3-yl)propyl]amino]-1,3-thiazol-5-yl]-3-(furan-2-ylmethylidene)-1H-indol-2-one 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C([C@@H](N)CC=1C2=CC=CC=C2NC=1)NC(S1)=NC=C1C(C=C12)=CC=C1NC(=O)\C2=C/C1=CC=CO1 CQLSDNLEPHKRAL-ZHMVQQCMSA-N 0.000 claims 1
- LUSRHBIKOIXOAC-AAWXNRKFSA-N (3e)-6-[2-[[(2s)-2-amino-3-(1h-indol-3-yl)propyl]amino]-1,3-thiazol-5-yl]-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound C([C@@H](N)CC=1C2=CC=CC=C2NC=1)NC(S1)=NC=C1C(C=C1NC2=O)=CC=C1\C2=C/C1=CN=CN1 LUSRHBIKOIXOAC-AAWXNRKFSA-N 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
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- HBAJEILBHKIJBU-AWEZNQCLSA-N 6-[2-[[(2s)-2-amino-3-(4-chlorophenyl)propyl]amino]-1,3-thiazol-5-yl]-3h-1,3-benzoxazol-2-one Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2OC(=O)NC2=CC=1)N)C1=CC=C(Cl)C=C1 HBAJEILBHKIJBU-AWEZNQCLSA-N 0.000 claims 1
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| CA2693473A1 (en) | 2007-07-17 | 2009-01-22 | Amgen Inc. | Thiadiazole modulators of pkb |
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| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| CN106243100B (zh) * | 2008-10-10 | 2019-04-09 | Vm生物医药公司 | 治疗酒精使用障碍，疼痛和其他疾病的药物组合与方法 |
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| EP2440556A1 (en) * | 2009-06-10 | 2012-04-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of phosphatidylinositol 3-kinase |
| SMT201700430T1 (it) | 2009-06-25 | 2018-01-11 | Alkermes Pharma Ireland Ltd | Composti eterociclici per il trattamento di disturbi neurologici e psicologici |
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| CA2777087C (en) | 2009-10-08 | 2017-10-31 | Glaxosmithkline Llc | Combination |
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| WO2011049625A1 (en) | 2009-10-20 | 2011-04-28 | Mansour Samadpour | Method for aflatoxin screening of products |
| EP3444242A3 (en) | 2009-11-05 | 2019-03-20 | Rhizen Pharmaceuticals S.A. | Novel benzopyran kinase modulators |
| US20130005979A1 (en) * | 2010-03-15 | 2013-01-03 | Kuraray Co. Ltd. | Thienopyridine derivative, method for producing same and organic semiconductor device using same |
| JP5578705B2 (ja) * | 2010-03-29 | 2014-08-27 | 公益財団法人相模中央化学研究所 | （アリール）ジフルオロ酢酸エステル誘導体及びその製造方法 |
| JP2013525303A (ja) * | 2010-04-16 | 2013-06-20 | アッヴィ・インコーポレイテッド | フタラジン−（２ｈ）−オン系キナーゼ阻害薬 |
| WO2011130921A1 (en) * | 2010-04-23 | 2011-10-27 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| US20130102605A1 (en) * | 2010-04-23 | 2013-04-25 | Peng Liang | Inhibitors of akt activity |
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- 2007-01-11 US US11/652,728 patent/US7514566B2/en active Active
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- 2007-01-11 CN CNA2007800097081A patent/CN101421265A/zh active Pending
- 2007-01-11 JP JP2008551297A patent/JP5199885B2/ja not_active Expired - Fee Related
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- 2007-01-11 AU AU2007207743A patent/AU2007207743B2/en not_active Ceased
- 2007-01-11 KR KR1020087019941A patent/KR20080091369A/ko not_active Withdrawn
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- 2007-01-17 TW TW096101796A patent/TW200738657A/zh unknown
- 2007-01-18 UY UY30098A patent/UY30098A1/es not_active Application Discontinuation
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2008
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2009
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