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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- LEICLQSPUKYOCA-INIZCTEOSA-N 5-[2-[[(2s)-2-amino-3-[4-(trifluoromethyl)phenyl]propyl]amino]-4-(methoxymethyl)-1,3-thiazol-5-yl]-3-methyl-1h-benzimidazol-2-one Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2N(C)C(=O)NC2=CC=1)COC)C1=CC=C(C(F)(F)F)C=C1 LEICLQSPUKYOCA-INIZCTEOSA-N 0.000 claims 1
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- CELYFJOYJNTTEV-AWEZNQCLSA-N 6-[2-[[(2s)-2-amino-3-(1h-indol-3-yl)propyl]amino]-1,3-thiazol-5-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC=C2C(C[C@@H](CNC=3SC(=CN=3)C=3C=C4OC(=O)NC4=CC=3)N)=CNC2=C1 CELYFJOYJNTTEV-AWEZNQCLSA-N 0.000 claims 1
- 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
- FNQWGQWNXGGAFV-AWEZNQCLSA-N 6-[2-[[(2s)-2-amino-3-(4-methoxyphenyl)propyl]amino]-1,3-thiazol-5-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(OC)=CC=C1C[C@H](N)CNC1=NC=C(C=2C=C3OC(=O)NC3=CC=2)S1 FNQWGQWNXGGAFV-AWEZNQCLSA-N 0.000 claims 1
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- LCTODEYEWLOXRB-INIZCTEOSA-N [2-[[(2s)-2-amino-3-[4-(trifluoromethyl)phenyl]propyl]amino]-5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-4-yl]methanol Chemical compound C([C@H](N)CNC=1SC(=C(N=1)CO)C1=CC=C2NN=C(C2=C1)C)C1=CC=C(C(F)(F)F)C=C1 LCTODEYEWLOXRB-INIZCTEOSA-N 0.000 claims 1
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| UA103319C2 (en) * | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
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| EA201170349A1 (ru) * | 2008-08-18 | 2011-08-30 | Йейл Юниверсити | Модуляторы mif |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | 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 |
| JP5770102B2 (ja) * | 2008-12-19 | 2015-08-26 | ジェネンテック， インコーポレイテッド | 複素環化合物と使用方法 |
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| WO2011049625A1 (en) | 2009-10-20 | 2011-04-28 | Mansour Samadpour | Method for aflatoxin screening of products |
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| 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 |
| MX2012012052A (es) * | 2010-04-16 | 2013-03-21 | Abbvie Inc | Inhibidores de ftalazin-(2h)-ona de cinasas. |
| WO2011130921A1 (en) * | 2010-04-23 | 2011-10-27 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| EP2579872A4 (en) * | 2010-04-23 | 2013-11-13 | Merck Sharp & Dohme | HAMMER OF ACT ACTIVITY |
| JO2998B1 (ar) | 2010-06-04 | 2016-09-05 | Amgen Inc | مشتقات بيبيريدينون كمثبطات mdm2 لعلاج السرطان |
| PH12013502240B1 (en) | 2011-05-04 | 2018-06-27 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of protein kinase |
| WO2013049250A1 (en) | 2011-09-27 | 2013-04-04 | Amgen Inc. | Heterocyclic compounds as mdm2 inhibitors for the treatment of cancer |
| CN103304468A (zh) * | 2012-03-13 | 2013-09-18 | 华东师范大学 | 一种氧化吲哚的一锅法串联合成方法 |
| US9499533B2 (en) | 2012-03-27 | 2016-11-22 | Shionogi & Co., Ltd. | Aromatic 5-membered heterocyclic derivative having TRPV4-Inhibiting activity |
| WO2013173382A1 (en) | 2012-05-15 | 2013-11-21 | Amgen Inc. | Benzothiophene sulfonamides and other compounds that interact with glucokinase regulatory protein |
| KR102216606B1 (ko) | 2012-07-04 | 2021-02-17 | 리젠 파마슈티컬스 소시에떼 아노님 | 선택적 pi3k 델타 억제제 |
| EP2958902B1 (en) | 2013-02-19 | 2017-11-15 | Amgen Inc. | Cis-morpholinone and other compounds as mdm2 inhibitors for the treatment of cancer |
| CA2904152A1 (en) * | 2013-03-13 | 2014-10-02 | Boston Biomedical, Inc. | 3-(aryl or heteroaryl) methyleneindolin-2-one derivatives as inhibitors of cancer stem cell pathway kinases for the treatment of cancer |
| WO2014151863A1 (en) | 2013-03-14 | 2014-09-25 | Amgen Inc. | Heteroaryl acid morpholinone compounds as mdm2 inhibitors for the treatment of cancer |
| JOP20200296A1 (ar) | 2013-06-10 | 2017-06-16 | Amgen Inc | عمليات صنع وأشكال بلورية من mdm2 مثبط |
| PT3068393T (pt) | 2013-11-11 | 2022-06-14 | Amgen Inc | Terapia de combinação, incluindo um inibidor de mdm2 e um ou mais agentes farmaceuticamente ativos adicionais para o tratamento de cancros |
| KR20170122799A (ko) * | 2015-03-02 | 2017-11-06 | 리겔 파마슈티칼스, 인크. | TGF-β 억제제 |
| WO2017151409A1 (en) | 2016-02-29 | 2017-09-08 | University Of Florida Research Foundation, Incorporated | Chemotherapeutic methods |
| WO2017153527A1 (en) * | 2016-03-10 | 2017-09-14 | Astrazeneca Ab | Novel inhibitors of phosphatidylinositol 3-kinase gamma |
| JP7129420B6 (ja) | 2017-03-30 | 2024-02-02 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | Ｈｐｋ１阻害剤としてのイソキノリン |
| JOP20190272A1 (ar) | 2017-05-22 | 2019-11-21 | Amgen Inc | مثبطات kras g12c وطرق لاستخدامها |
| AR112797A1 (es) | 2017-09-08 | 2019-12-11 | Amgen Inc | Inhibidores de kras g12c y métodos para utilizarlos |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
| CA3127373A1 (en) | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd |
| AU2019230014B2 (en) | 2018-03-05 | 2024-11-28 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| WO2019213516A1 (en) | 2018-05-04 | 2019-11-07 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
| JP7369719B2 (ja) | 2018-06-12 | 2023-10-26 | アムジエン・インコーポレーテツド | ＫＲａｓ Ｇ１２Ｃ阻害剤及びそれを使用する方法 |
| TW202019905A (zh) | 2018-07-24 | 2020-06-01 | 瑞士商赫孚孟拉羅股份公司 | 異喹啉化合物及其用途 |
| TW202024053A (zh) | 2018-10-02 | 2020-07-01 | 美商建南德克公司 | 異喹啉化合物及其用途 |
| US11612606B2 (en) | 2018-10-03 | 2023-03-28 | Genentech, Inc. | 8-aminoisoquinoline compounds and uses thereof |
| JP7377679B2 (ja) | 2018-11-19 | 2023-11-10 | アムジエン・インコーポレーテツド | がん治療のためのｋｒａｓｇ１２ｃ阻害剤及び１種以上の薬学的に活性な追加の薬剤を含む併用療法 |
| EP3738593A1 (en) | 2019-05-14 | 2020-11-18 | Amgen, Inc | Dosing of kras inhibitor for treatment of cancers |
| CA3225293A1 (en) | 2019-05-21 | 2020-11-26 | Amgen Inc. | Solid state forms |
| US20220372018A1 (en) * | 2019-08-02 | 2022-11-24 | Amgen Inc. | Kif18a inhibitors |
| WO2021076655A1 (en) | 2019-10-15 | 2021-04-22 | Amgen Inc. | Combination therapy of kras inhibitor and shp2 inhibitor for treatment of cancers |
| US20230028414A1 (en) | 2019-12-16 | 2023-01-26 | Amgen Inc. | Dosing regimen of kras g12c inhibitor |
| US12178902B1 (en) | 2020-01-12 | 2024-12-31 | University Of Southern California | Methods and compositions for fluid drainage by Piezo ion channel activation |
| CN111603466B (zh) * | 2020-06-29 | 2022-07-22 | 江南大学 | 一种乙酮类化合物在制备治疗肿瘤药物中的应用 |
| CN114014787B (zh) * | 2022-01-10 | 2022-03-22 | 苏州开元民生科技股份有限公司 | 一种制备(2s,3r)-对甲砜基苯丝氨酸乙酯的不对称合成方法 |
| CN116813608B (zh) * | 2023-06-08 | 2024-03-22 | 英矽智能科技(上海)有限公司 | 噻唑类化合物及其应用 |
Family Cites Families (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591600A (en) * | 1969-07-07 | 1971-07-06 | Stauffer Chemical Co | 2-aminothiazole phosphates and phosphonates |
| GB1435139A (en) * | 1972-08-17 | 1976-05-12 | Sumitomo Chemical Co | Thiazole derivatives |
| JPS5239827B2 (enExample) | 1973-11-08 | 1977-10-07 | ||
| US4086239A (en) * | 1977-07-01 | 1978-04-25 | Stauffer Chemical Company | Thiazole bis-phosphates and phosphonates, intermediates, and insecticidal compositions and methods |
| DK150068C (da) | 1978-06-02 | 1987-06-29 | Pfizer | Analogifremgangsmaade til fremstilling af aminothiazoler |
| US4297365A (en) * | 1978-08-04 | 1981-10-27 | Ciba-Geigy Corporation | Benzimidazoles and pharmaceutical preparations containing such compounds |
| US4451471A (en) * | 1981-03-18 | 1984-05-29 | Ciba-Geigy Corporation | Certain 2,4,5-tri-substituted thiazoles, pharmaceutical compositions containing same and methods of using same |
| FR2511375A1 (fr) * | 1981-08-17 | 1983-02-18 | Rhone Poulenc Sante | Nouveaux derives de la cephalosporine, leur preparation et les medicaments qui les contiennent |
| DE3630732A1 (de) * | 1986-09-10 | 1988-03-17 | Bayer Ag | 2-cyano-2-alkoximino-acetamide |
| US5232921A (en) * | 1987-03-12 | 1993-08-03 | Sanofi | Thiazole derivatives active on the cholinergic system, process for obtention and pharmaceutical compositions |
| JPH0753666B2 (ja) | 1987-09-14 | 1995-06-07 | 久光製薬株式会社 | 置換ジフェニルチアゾール誘導体からなる抗炎症剤 |
| FR2636628B1 (fr) * | 1988-08-25 | 1990-12-28 | Sanofi Sa | Derives du thiadiazole-1,3,4, leur procede d'obtention et compositions pharmaceutiques en contenant |
| US5302608A (en) * | 1988-11-18 | 1994-04-12 | Takeda Chemical Industries, Ltd. | Age formation inhibitors |
| US5145860A (en) * | 1989-01-05 | 1992-09-08 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole compounds and pharmaceutical composition comprising the same |
| US5550138A (en) * | 1992-03-25 | 1996-08-27 | Takeda Chemical Industries, Ltd. | Condensed thiadiazole derivative, method of its production, and use thereof |
| DE69526958T2 (de) * | 1994-11-29 | 2003-01-16 | Hisamitsu Pharmaceutical Co., Inc. | Antibakterielle oder bakterizide mittel, die 2-aminothiazolderivate und deren salze enthalten |
| FR2735777B1 (fr) | 1995-06-21 | 1997-09-12 | Sanofi Sa | Derives de 4-phenylaminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant |
| DE69923681T2 (de) | 1998-06-18 | 2006-01-12 | Bristol-Myers Squibb Co. | Kohlenstoff substituierte aminothiazole als inhibitoren von cyclin-abhängigen kinasen |
| US6407124B1 (en) | 1998-06-18 | 2002-06-18 | Bristol-Myers Squibb Company | Carbon substituted aminothiazole inhibitors of cyclin dependent kinases |
| GB9823873D0 (en) * | 1998-10-30 | 1998-12-30 | Pharmacia & Upjohn Spa | 2-ureido-thiazole derivatives,process for their preparation,and their use as antitumour agents |
| AU3487500A (en) | 1999-02-08 | 2000-08-25 | Lion Bioscience Ag | Thiazole derivatives and combinatorial libraries thereof |
| AUPP873799A0 (en) * | 1999-02-17 | 1999-03-11 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine compounds |
| UA71971C2 (en) * | 1999-06-04 | 2005-01-17 | Agoron Pharmaceuticals Inc | Diaminothiazoles, composition based thereon, a method for modulation of protein kinases activity, a method for the treatment of diseases mediated by protein kinases |
| JP2001114690A (ja) * | 1999-08-06 | 2001-04-24 | Takeda Chem Ind Ltd | ｐ３８ＭＡＰキナーゼ阻害剤 |
| WO2001010865A1 (en) * | 1999-08-06 | 2001-02-15 | Takeda Chemical Industries, Ltd. | p38MAP KINASE INHIBITORS |
| US7495018B2 (en) * | 2000-03-30 | 2009-02-24 | Takeda Pharmaceutical Company Limited | Substituted 1,3-thiazole compounds, their production and use |
| US6586453B2 (en) * | 2000-04-03 | 2003-07-01 | 3-Dimensional Pharmaceuticals, Inc. | Substituted thiazoles and the use thereof as inhibitors of plasminogen activator inhibitor-1 |
| US7074934B2 (en) * | 2000-06-13 | 2006-07-11 | Tularik Limited | Serine protease inhibitors |
| GT200100147A (es) | 2000-07-31 | 2002-06-25 | Derivados de imidazol | |
| JP4689801B2 (ja) | 2000-08-09 | 2011-05-25 | ケミプロ化成株式会社 | アミノチアゾール誘導体の製造方法 |
| JP2002053566A (ja) | 2000-08-11 | 2002-02-19 | Japan Tobacco Inc | チアゾール化合物及びその医薬用途 |
| GB0114185D0 (en) * | 2001-06-12 | 2001-08-01 | Protherics Molecular Design Lt | Compounds |
| US20040097555A1 (en) * | 2000-12-26 | 2004-05-20 | Shinegori Ohkawa | Concomitant drugs |
| AR032653A1 (es) * | 2001-02-09 | 2003-11-19 | Telik Inc | Inhibidores heterociclicos del trasportador de glicina 2 composiciones farmaceuticas, uso y metodos. |
| EP1256578B1 (en) * | 2001-05-11 | 2006-01-11 | Pfizer Products Inc. | Thiazole derivatives and their use as cdk inhibitors |
| EP1402900A1 (en) * | 2001-06-11 | 2004-03-31 | Takeda Chemical Industries, Ltd. | Medicinal compositions |
| AR039059A1 (es) * | 2001-08-06 | 2005-02-09 | Sanofi Aventis | Compuesto derivado de acilaminotiazol, su utilizacion, procedimientos para prepararlo, composicion farmaceutica que lo comprende, y compuestos intermediarios |
| DE60217140T2 (de) * | 2001-09-28 | 2007-04-19 | Cyclacel Ltd. | N-(4-(4-methylthiazol-5-yl)pyrimidin-2-yl)-n-phenylamine als antiproliferative verbindungen |
| GB0123589D0 (en) * | 2001-10-01 | 2001-11-21 | Syngenta Participations Ag | Organic compounds |
| JP2005510508A (ja) * | 2001-11-08 | 2005-04-21 | 藤沢薬品工業株式会社 | アデノシンアンタゴニストとしてのチアゾールピリダジノン類 |
| EP1474141A1 (en) | 2002-02-13 | 2004-11-10 | Pharmagene Laboratories Ltd | 5-ht2b receptor antagonists |
| MY156407A (en) * | 2002-02-28 | 2016-02-26 | Novartis Ag | 5-phenylthiazole derivatives and use as p13 kinase inhibitors |
| DE60316411T2 (de) | 2002-02-28 | 2008-06-12 | F. Hoffmann-La Roche Ag | Thiazolderivate als npy-rezeptorantagonisten |
| EP1507534A4 (en) * | 2002-05-10 | 2006-11-08 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| FR2842523A1 (fr) * | 2002-07-17 | 2004-01-23 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur application en therapeutique |
| BR0314611A (pt) * | 2002-10-09 | 2005-07-26 | Pfizer Prod Inc | Compostos de tiazol para o tratamento de distúrbios neurodegenerativos |
| EP1558607B1 (en) | 2002-10-30 | 2010-05-05 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of rock and other protein kinases |
| GB0226583D0 (en) * | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| AR042052A1 (es) | 2002-11-15 | 2005-06-08 | Vertex Pharma | Diaminotriazoles utiles como inhibidores de proteinquinasas |
| US20050004186A1 (en) | 2002-12-20 | 2005-01-06 | Pfizer Inc | MEK inhibiting compounds |
| FR2850380B1 (fr) * | 2003-01-23 | 2006-07-07 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur utilisation en therapeutique |
| JP2006182648A (ja) | 2003-04-08 | 2006-07-13 | Dai Ichi Seiyaku Co Ltd | ７員複素環誘導体 |
| AR044519A1 (es) * | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| ATE536353T1 (de) | 2003-08-20 | 2011-12-15 | Vertex Pharma | 2-(4-amino-1,2,5-oxadiazol-4-yl)-imidazol- verbindungen als protein kinase inhibitoren |
| EP1664006A2 (en) * | 2003-09-06 | 2006-06-07 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| GB0327380D0 (en) | 2003-11-25 | 2003-12-31 | Cyclacel Ltd | Method |
| GB0329275D0 (en) | 2003-12-18 | 2004-01-21 | Merck Sharp & Dohme | Therapeutic treatment |
| CN1926121B (zh) | 2004-01-12 | 2012-06-13 | 默克雪兰诺有限公司 | 噻唑衍生物及其应用 |
| NZ548531A (en) * | 2004-01-16 | 2010-01-29 | Sanofi Aventis | Acylaminothiazole derivatives, preparation method thereof and use of same in therapeutics |
| JP4813371B2 (ja) * | 2004-01-16 | 2011-11-09 | サノフイ−アベンテイス | アシルアミノチアゾール誘導体及びβ−アミロイド阻害剤としてのこれらの使用 |
| US20070185152A1 (en) * | 2004-03-02 | 2007-08-09 | Smithkline Beecham Corporation | Inhibitors of akt activity |
| DK1730119T3 (da) | 2004-03-23 | 2008-08-11 | Pfizer Prod Inc | Imidazolforbindelser til behandling af neurodegenerative forstyrrelser |
| CN1989131A (zh) * | 2004-03-30 | 2007-06-27 | 希龙公司 | 取代的噻吩衍生物用作抗癌药 |
| US7575751B2 (en) * | 2004-04-27 | 2009-08-18 | Research Development Foundation | Activin-A mutants |
| CA2571828A1 (en) * | 2004-05-21 | 2005-12-01 | Mpex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors and methods of treating bacterial infections |
| GB0411791D0 (en) | 2004-05-26 | 2004-06-30 | Cyclacel Ltd | Compounds |
| ES2401138T3 (es) | 2004-08-13 | 2013-04-17 | Genentech, Inc. | Inhibidores basados en tiazol de enzimas que usan ATP |
| WO2006038734A1 (en) * | 2004-10-08 | 2006-04-13 | Astellas Pharma Inc. | Pyridazinone derivatives cytokines inhibitors |
| MX2007004551A (es) * | 2004-10-18 | 2007-05-23 | Amgen Inc | Compuestos tiadiazol y metodos de uso. |
| SE0402735D0 (sv) | 2004-11-09 | 2004-11-09 | Astrazeneca Ab | Novel compounds |
| US20060178388A1 (en) * | 2005-02-04 | 2006-08-10 | Wrobleski Stephen T | Phenyl-substituted pyrimidine compounds useful as kinase inhibitors |
| KR100917511B1 (ko) * | 2005-02-28 | 2009-09-16 | 니뽄 다바코 산교 가부시키가이샤 | Ｓｙｋ 저해 활성을 갖는 신규한 아미노피리딘 화합물 |
| AU2006261327B2 (en) * | 2005-06-17 | 2012-07-05 | Apogee Biotechnology Corporation | Sphingosine kinase inhibitors |
| WO2007008541A2 (en) | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
| DE102005048072A1 (de) | 2005-09-24 | 2007-04-05 | Bayer Cropscience Ag | Thiazole als Fungizide |
| US7871982B2 (en) | 2005-12-09 | 2011-01-18 | Meiji Seika Kaisha, Ltd. | Lincomycin derivatives and antimicrobial agents comprising the same as active ingredient |
| EP1971597A2 (en) | 2005-12-12 | 2008-09-24 | Genelabs Technologies, Inc. | N-(5-membered heteroaromatic ring)-amido anti-viral compounds |
| US7897601B2 (en) | 2006-01-18 | 2011-03-01 | Intervet, Inc. | Cannabinoid receptor modulators |
| WO2007082805A1 (en) | 2006-01-18 | 2007-07-26 | F. Hoffmann-La Roche Ag | Cis-4, 5-biaryl-2-heterocyclic-imidazolines as mdm2 inhibitors |
| EP1981884B1 (en) | 2006-01-18 | 2012-06-13 | Amgen, Inc | Thiazole compounds as protein kinase b (pkb) inhibitors |
| US20080242694A1 (en) | 2006-09-18 | 2008-10-02 | D Sidocky Neil R | Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith |
-
2007
- 2007-01-11 EP EP07718125A patent/EP1981884B1/en active Active
- 2007-01-11 MY MYPI20082598A patent/MY149143A/en unknown
- 2007-01-11 US US11/652,728 patent/US7514566B2/en active Active
- 2007-01-11 JP JP2008551297A patent/JP5199885B2/ja not_active Expired - Fee Related
- 2007-01-11 BR BRPI0706621-0A patent/BRPI0706621A2/pt not_active IP Right Cessation
- 2007-01-11 CN CNA2007800097081A patent/CN101421265A/zh active Pending
- 2007-01-11 ES ES07718125T patent/ES2389062T3/es active Active
- 2007-01-11 KR KR1020087019941A patent/KR20080091369A/ko not_active Withdrawn
- 2007-01-11 EA EA200801716A patent/EA200801716A1/ru unknown
- 2007-01-11 WO PCT/US2007/000871 patent/WO2007084391A2/en not_active Ceased
- 2007-01-11 CA CA2636077A patent/CA2636077C/en not_active Expired - Fee Related
- 2007-01-11 AU AU2007207743A patent/AU2007207743B2/en not_active Ceased
- 2007-01-17 TW TW096101796A patent/TW200738657A/zh unknown
- 2007-01-18 UY UY30098A patent/UY30098A1/es not_active Application Discontinuation
- 2007-01-18 PE PE2007000057A patent/PE20071114A1/es not_active Application Discontinuation
- 2007-01-18 AR ARP070100212A patent/AR059064A1/es unknown
- 2007-11-01 UA UAA200810455A patent/UA91895C2/ru unknown
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2008
- 2008-07-10 IL IL192751A patent/IL192751A0/en unknown
- 2008-07-23 ZA ZA200806386A patent/ZA200806386B/xx unknown
- 2008-08-18 NO NO20083572A patent/NO20083572L/no not_active Application Discontinuation
- 2008-08-18 CR CR10211A patent/CR10211A/es not_active Application Discontinuation
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2009
- 2009-02-11 US US12/378,195 patent/US8084479B2/en active Active
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