AU2013347771B2 - Compounds and their methods of use - Google Patents
Compounds and their methods of use Download PDFInfo
- Publication number
- AU2013347771B2 AU2013347771B2 AU2013347771A AU2013347771A AU2013347771B2 AU 2013347771 B2 AU2013347771 B2 AU 2013347771B2 AU 2013347771 A AU2013347771 A AU 2013347771A AU 2013347771 A AU2013347771 A AU 2013347771A AU 2013347771 B2 AU2013347771 B2 AU 2013347771B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- oct
- pharmaceutically acceptable
- bis
- acceptable salt
- 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.)
- Ceased
Links
- 0 COc1ccccc1CC(NC1=CCN=C([C@](CCC2)C[C@@]2c2nnc(NC(Cc3ncccc3)=O)[s]2)S1)=* Chemical compound COc1ccccc1CC(NC1=CCN=C([C@](CCC2)C[C@@]2c2nnc(NC(Cc3ncccc3)=O)[s]2)S1)=* 0.000 description 26
- ORLZHHOWTODPEL-WDSKDSINSA-N Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(N)[s]2)[s]1 Chemical compound Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(N)[s]2)[s]1 ORLZHHOWTODPEL-WDSKDSINSA-N 0.000 description 3
- GDSDUMCXSKBVSG-UHFFFAOYSA-N CCOC(C(C(OCC)=O)c1ncccn1)=O Chemical compound CCOC(C(C(OCC)=O)c1ncccn1)=O GDSDUMCXSKBVSG-UHFFFAOYSA-N 0.000 description 2
- BHLDBPUFFUAMGE-HOTGVXAUSA-N COc1cccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cccc(OC)n4)=O)[s]3)[s]2)=O)n1 Chemical compound COc1cccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cccc(OC)n4)=O)[s]3)[s]2)=O)n1 BHLDBPUFFUAMGE-HOTGVXAUSA-N 0.000 description 2
- LPVDSXDDCBBRMS-IRXDYDNUSA-N O=C(Cc1cccc(OC(F)(F)F)c1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ncccc3)=O)[s]2)[s]1 Chemical compound O=C(Cc1cccc(OC(F)(F)F)c1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ncccc3)=O)[s]2)[s]1 LPVDSXDDCBBRMS-IRXDYDNUSA-N 0.000 description 2
- YCYKGQJUTRXAFP-UHFFFAOYSA-N Bc1cc(CC(OC)=O)ccc1 Chemical compound Bc1cc(CC(OC)=O)ccc1 YCYKGQJUTRXAFP-UHFFFAOYSA-N 0.000 description 1
- MASZPNYJHWSABL-KOXVQWLPSA-N C/N=C/c1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(C5=NC5)ccn4)=O)[s]3)[s]2)=O)ncc1 Chemical compound C/N=C/c1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(C5=NC5)ccn4)=O)[s]3)[s]2)=O)ncc1 MASZPNYJHWSABL-KOXVQWLPSA-N 0.000 description 1
- CIFSKZDQGRCLBN-UHFFFAOYSA-N CC(CCC1)CC1C(O)=O Chemical compound CC(CCC1)CC1C(O)=O CIFSKZDQGRCLBN-UHFFFAOYSA-N 0.000 description 1
- CZYUDVJUSHSHTB-UIOOFZCWSA-N CC(Nc1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(NC(C)=O)ccc4)=C)[s]3)[s]2)=C)ccc1)=O Chemical compound CC(Nc1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(NC(C)=O)ccc4)=C)[s]3)[s]2)=C)ccc1)=O CZYUDVJUSHSHTB-UIOOFZCWSA-N 0.000 description 1
- LHGGTNDAFRYLGW-SFHVURJKSA-N CCC[C@@H](CCc1nnc(NC(Cc2nc(N(C3)CC3(F)F)ccc2)=O)[s]1)c1nnc(NC(Cc2cccc(N(C3)CC3(F)F)n2)=O)[s]1 Chemical compound CCC[C@@H](CCc1nnc(NC(Cc2nc(N(C3)CC3(F)F)ccc2)=O)[s]1)c1nnc(NC(Cc2cccc(N(C3)CC3(F)F)n2)=O)[s]1 LHGGTNDAFRYLGW-SFHVURJKSA-N 0.000 description 1
- KNPJNOHLMPVMLN-VXKWHMMOSA-N CCNc1cccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(NCC)ccc4)=O)[s]3)[s]2)=O)c1 Chemical compound CCNc1cccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(NCC)ccc4)=O)[s]3)[s]2)=O)c1 KNPJNOHLMPVMLN-VXKWHMMOSA-N 0.000 description 1
- CAERSDJFKGMKLY-UHFFFAOYSA-N CCOC(Cc1cc(Br)ccc1)=O Chemical compound CCOC(Cc1cc(Br)ccc1)=O CAERSDJFKGMKLY-UHFFFAOYSA-N 0.000 description 1
- BTRGZBIXPLFVNK-UHFFFAOYSA-N CCOC(Cc1ccc(C)cc1)=O Chemical compound CCOC(Cc1ccc(C)cc1)=O BTRGZBIXPLFVNK-UHFFFAOYSA-N 0.000 description 1
- AZEPHFQYDLVEOU-UHFFFAOYSA-N CCOC(Cc1nccc(OCC)c1)=O Chemical compound CCOC(Cc1nccc(OCC)c1)=O AZEPHFQYDLVEOU-UHFFFAOYSA-N 0.000 description 1
- DZQZAEMLHNEMEN-UHFFFAOYSA-N CCOC(Cc1ncccn1)=O Chemical compound CCOC(Cc1ncccn1)=O DZQZAEMLHNEMEN-UHFFFAOYSA-N 0.000 description 1
- CEVJFQNAYZKCBO-ROUUACIJSA-N CCOc1cnc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc(cc4)ncc4OCC)=O)[s]3)[s]2)=O)cc1 Chemical compound CCOc1cnc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc(cc4)ncc4OCC)=O)[s]3)[s]2)=O)cc1 CEVJFQNAYZKCBO-ROUUACIJSA-N 0.000 description 1
- GNRHBYCQGMOXLD-OALUTQOASA-N CC[C@@H](C[C@H](CC)c1nnc(NC(Cc2ccc(CN)cn2)=O)[s]1)c1nnc(NC(Cc2ncc(CN)cc2)=O)[s]1 Chemical compound CC[C@@H](C[C@H](CC)c1nnc(NC(Cc2ccc(CN)cn2)=O)[s]1)c1nnc(NC(Cc2ncc(CN)cc2)=O)[s]1 GNRHBYCQGMOXLD-OALUTQOASA-N 0.000 description 1
- IXNWODOJXMAKDF-ACHIHNKUSA-N CN(CC1)CCC1c1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(C5CCN(C)CC5)ccc4)=O)[s]3)[s]2)=O)ccc1 Chemical compound CN(CC1)CCC1c1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(C5CCN(C)CC5)ccc4)=O)[s]3)[s]2)=O)ccc1 IXNWODOJXMAKDF-ACHIHNKUSA-N 0.000 description 1
- NQQYJZZNWQRLDL-PMACEKPBSA-N CNc1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(NC)ccc4)=O)[s]3)[s]2)=O)ccc1 Chemical compound CNc1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(NC)ccc4)=O)[s]3)[s]2)=O)ccc1 NQQYJZZNWQRLDL-PMACEKPBSA-N 0.000 description 1
- XADSVCKQRXFYAX-RYUDHWBXSA-N CNc1nc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4c[s]c(NC)n4)=O)[s]3)[s]2)=O)c[s]1 Chemical compound CNc1nc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4c[s]c(NC)n4)=O)[s]3)[s]2)=O)c[s]1 XADSVCKQRXFYAX-RYUDHWBXSA-N 0.000 description 1
- NYAZLFKSCFNMKV-UHFFFAOYSA-N COC(Cc(cc1)cnc1Cl)=O Chemical compound COC(Cc(cc1)cnc1Cl)=O NYAZLFKSCFNMKV-UHFFFAOYSA-N 0.000 description 1
- DVYWFSXIRABQKA-UHFFFAOYSA-N COC(Cc(cc1)ncc1C(O)=C)=O Chemical compound COC(Cc(cc1)ncc1C(O)=C)=O DVYWFSXIRABQKA-UHFFFAOYSA-N 0.000 description 1
- XTQKFBGFHDNUFY-UHFFFAOYSA-N COC(Cc1c[s]c(N)n1)=O Chemical compound COC(Cc1c[s]c(N)n1)=O XTQKFBGFHDNUFY-UHFFFAOYSA-N 0.000 description 1
- PTUBPGRSZCVDCM-UHFFFAOYSA-N COC(Cc1cc(N2CCCC2)ccc1)=O Chemical compound COC(Cc1cc(N2CCCC2)ccc1)=O PTUBPGRSZCVDCM-UHFFFAOYSA-N 0.000 description 1
- QUFHQILFHCCMMA-UHFFFAOYSA-N COC(Cc1cc(OC)ccn1)=O Chemical compound COC(Cc1cc(OC)ccn1)=O QUFHQILFHCCMMA-UHFFFAOYSA-N 0.000 description 1
- MSPVJLQSTROFGA-UHFFFAOYSA-N COC(Cc1cccc(N2CCC2)c1)=O Chemical compound COC(Cc1cccc(N2CCC2)c1)=O MSPVJLQSTROFGA-UHFFFAOYSA-N 0.000 description 1
- RSAZQXGQPHMNFK-UHFFFAOYSA-N COC(Cc1nc(OC)ccc1)=O Chemical compound COC(Cc1nc(OC)ccc1)=O RSAZQXGQPHMNFK-UHFFFAOYSA-N 0.000 description 1
- NTLCULCHINMENJ-VYRBHSGPSA-N COc1c(CC(Nc2nnc([C@@H](CCC3)CC3c3nnc(NC(Cc4ncccc4OC)=O)[s]3)[s]2)=O)nccc1 Chemical compound COc1c(CC(Nc2nnc([C@@H](CCC3)CC3c3nnc(NC(Cc4ncccc4OC)=O)[s]3)[s]2)=O)nccc1 NTLCULCHINMENJ-VYRBHSGPSA-N 0.000 description 1
- BHERQMNDGHXDLU-ROUUACIJSA-N COc1ccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc(cc4)cnc4OC)=O)[s]3)[s]2)=O)cn1 Chemical compound COc1ccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc(cc4)cnc4OC)=O)[s]3)[s]2)=O)cn1 BHERQMNDGHXDLU-ROUUACIJSA-N 0.000 description 1
- YZCJEAPEIJCVED-HOTGVXAUSA-N COc1ccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc(cc4)ncc4OC)=O)[s]3)[s]2)=O)nc1 Chemical compound COc1ccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc(cc4)ncc4OC)=O)[s]3)[s]2)=O)nc1 YZCJEAPEIJCVED-HOTGVXAUSA-N 0.000 description 1
- YEPCSSRUAMEQGL-ROUUACIJSA-N COc1ccccc1CC(Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ncccc3)=O)[s]2)[s]1)=O Chemical compound COc1ccccc1CC(Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ncccc3)=O)[s]2)[s]1)=O YEPCSSRUAMEQGL-ROUUACIJSA-N 0.000 description 1
- XQORFPCVQWDORM-ROUUACIJSA-N COc1nccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4ccnc(OC)c4)=O)[s]3)[s]2)=O)c1 Chemical compound COc1nccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4ccnc(OC)c4)=O)[s]3)[s]2)=O)c1 XQORFPCVQWDORM-ROUUACIJSA-N 0.000 description 1
- MWVSSYOXUWYVTJ-UHFFFAOYSA-N Cc1cc(OC)ccn1 Chemical compound Cc1cc(OC)ccn1 MWVSSYOXUWYVTJ-UHFFFAOYSA-N 0.000 description 1
- GFKVJXHHXRAWNK-ROUUACIJSA-N Cc1ccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4ncc(C)cc4)=O)[s]3)[s]2)=O)nc1 Chemical compound Cc1ccc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4ncc(C)cc4)=O)[s]3)[s]2)=O)nc1 GFKVJXHHXRAWNK-ROUUACIJSA-N 0.000 description 1
- AWDCQBLOCBSBNR-ZGJBTBESSA-N Cc1cccc(CC(Nc2nnc([C@@H](CCC3)CC3c3nnc(NC([C@@H](c4ccccc4)O)=O)[s]3)[s]2)O)c1 Chemical compound Cc1cccc(CC(Nc2nnc([C@@H](CCC3)CC3c3nnc(NC([C@@H](c4ccccc4)O)=O)[s]3)[s]2)O)c1 AWDCQBLOCBSBNR-ZGJBTBESSA-N 0.000 description 1
- RJCFWJNYLJRLRC-UHFFFAOYSA-N Cc1nc(CC(O)=O)c[s]1 Chemical compound Cc1nc(CC(O)=O)c[s]1 RJCFWJNYLJRLRC-UHFFFAOYSA-N 0.000 description 1
- WIMNZMOEBDPZTB-UHFFFAOYSA-N Cc1nc(OC)ccc1 Chemical compound Cc1nc(OC)ccc1 WIMNZMOEBDPZTB-UHFFFAOYSA-N 0.000 description 1
- FPVVTFKRGSIONE-UHFFFAOYSA-N Cc1nnc(NC(Cc2ncccc2)=O)[s]1 Chemical compound Cc1nnc(NC(Cc2ncccc2)=O)[s]1 FPVVTFKRGSIONE-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N Clc1ncccn1 Chemical compound Clc1ncccn1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- FUEKZGULXDUQPN-NPGWBMRXSA-N N#Cc1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(C5CNCCC5)ccc4)=O)[s]3)[s]2)=O)ccc1 Chemical compound N#Cc1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(C5CNCCC5)ccc4)=O)[s]3)[s]2)=O)ccc1 FUEKZGULXDUQPN-NPGWBMRXSA-N 0.000 description 1
- LCXVDFHODGJIQI-PMACEKPBSA-N NC(C1)CN1c1nc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cccc(C#N)c4)=O)[s]3)[s]2)=O)ccc1 Chemical compound NC(C1)CN1c1nc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cccc(C#N)c4)=O)[s]3)[s]2)=O)ccc1 LCXVDFHODGJIQI-PMACEKPBSA-N 0.000 description 1
- JEPNPXYFKLIGKF-UWVGGRQHSA-N Nc1nc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4c[s]c(N)n4)=O)[s]3)[s]2)=O)c[s]1 Chemical compound Nc1nc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4c[s]c(N)n4)=O)[s]3)[s]2)=O)c[s]1 JEPNPXYFKLIGKF-UWVGGRQHSA-N 0.000 description 1
- ORLZHHOWTODPEL-UHFFFAOYSA-N Nc1nnc(C(CCC2)CC2c2nnc(N)[s]2)[s]1 Chemical compound Nc1nnc(C(CCC2)CC2c2nnc(N)[s]2)[s]1 ORLZHHOWTODPEL-UHFFFAOYSA-N 0.000 description 1
- QDLBXAGTCLPUSV-RFZPGFLSSA-N Nc1nnc(C[C@@H]2[C@@H](Cc3nnc(N)[s]3)C2)[s]1 Chemical compound Nc1nnc(C[C@@H]2[C@@H](Cc3nnc(N)[s]3)C2)[s]1 QDLBXAGTCLPUSV-RFZPGFLSSA-N 0.000 description 1
- YOYFJZRYLFYLGQ-YPJRHXLCSA-N O=C(CC1C=NC(N(C2)CC2(F)F)=CC1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ccc(N(C4)CC4(F)F)nc3)=O)[s]2)[s]1 Chemical compound O=C(CC1C=NC(N(C2)CC2(F)F)=CC1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ccc(N(C4)CC4(F)F)nc3)=O)[s]2)[s]1 YOYFJZRYLFYLGQ-YPJRHXLCSA-N 0.000 description 1
- JVHIEPDWHCUBTK-HOTGVXAUSA-N O=C(CC1CC1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3cccc(N(C4)CC4(F)F)n3)=O)[s]2)[s]1 Chemical compound O=C(CC1CC1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3cccc(N(C4)CC4(F)F)n3)=O)[s]2)[s]1 JVHIEPDWHCUBTK-HOTGVXAUSA-N 0.000 description 1
- FWIOQNRAEMDDSM-UWVGGRQHSA-N O=C(CCC(F)(F)F)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(CCC(F)(F)F)=O)[s]2)[s]1 Chemical compound O=C(CCC(F)(F)F)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(CCC(F)(F)F)=O)[s]2)[s]1 FWIOQNRAEMDDSM-UWVGGRQHSA-N 0.000 description 1
- CGWLADZIZKOVJQ-ZEQRLZLVSA-N O=C(Cc(cc1)ccc1N(CCF)CCF)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc(cc3)ccc3N(C3)CC3(F)F)=O)[s]2)[s]1 Chemical compound O=C(Cc(cc1)ccc1N(CCF)CCF)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc(cc3)ccc3N(C3)CC3(F)F)=O)[s]2)[s]1 CGWLADZIZKOVJQ-ZEQRLZLVSA-N 0.000 description 1
- RIUKVRAKTWJASS-IRXDYDNUSA-N O=C(Cc(cc1)ncc1N(C1)CC1F)Nc1nnc([C@@H](CC2)C[C@H]2c2nnc(NC(Cc(nc3)ccc3N(C3)CC3F)=O)[s]2)[s]1 Chemical compound O=C(Cc(cc1)ncc1N(C1)CC1F)Nc1nnc([C@@H](CC2)C[C@H]2c2nnc(NC(Cc(nc3)ccc3N(C3)CC3F)=O)[s]2)[s]1 RIUKVRAKTWJASS-IRXDYDNUSA-N 0.000 description 1
- CDIHVIDWEXYVPY-KBPBESRZSA-N O=C(Cc(cc1)ncc1OC(F)F)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc(nc3)ccc3OC(F)F)=O)[s]2)[s]1 Chemical compound O=C(Cc(cc1)ncc1OC(F)F)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc(nc3)ccc3OC(F)F)=O)[s]2)[s]1 CDIHVIDWEXYVPY-KBPBESRZSA-N 0.000 description 1
- WAGHMTJVWYWHGO-RYUDHWBXSA-N O=C(Cc1c[nH]cn1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3c[nH]cn3)=O)[s]2)[s]1 Chemical compound O=C(Cc1c[nH]cn1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3c[nH]cn3)=O)[s]2)[s]1 WAGHMTJVWYWHGO-RYUDHWBXSA-N 0.000 description 1
- IUJXCIJMSPZOMR-RYUDHWBXSA-N O=C(Cc1c[s]cn1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3c[s]cn3)=O)[s]2)[s]1 Chemical compound O=C(Cc1c[s]cn1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3c[s]cn3)=O)[s]2)[s]1 IUJXCIJMSPZOMR-RYUDHWBXSA-N 0.000 description 1
- WTHBDRARLLXAJL-ROUUACIJSA-N O=C(Cc1cc(OC(F)(F)F)ccc1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(C(c3ccccc3)=O)=O)[s]2)[s]1 Chemical compound O=C(Cc1cc(OC(F)(F)F)ccc1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(C(c3ccccc3)=O)=O)[s]2)[s]1 WTHBDRARLLXAJL-ROUUACIJSA-N 0.000 description 1
- JWVNPTICKUXGJW-VXKWHMMOSA-N O=C(Cc1cccc(N(C2)CC2F)c1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3cc(N(C4)CC4F)ccc3)=O)[s]2)[s]1 Chemical compound O=C(Cc1cccc(N(C2)CC2F)c1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3cc(N(C4)CC4F)ccc3)=O)[s]2)[s]1 JWVNPTICKUXGJW-VXKWHMMOSA-N 0.000 description 1
- XUQCNIWAHBIDOG-ROUUACIJSA-N O=C(Cc1cccc2c1OCO2)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3c4OCOc4ccc3)=O)[s]2)[s]1 Chemical compound O=C(Cc1cccc2c1OCO2)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3c4OCOc4ccc3)=O)[s]2)[s]1 XUQCNIWAHBIDOG-ROUUACIJSA-N 0.000 description 1
- HROAFZLZQSBWII-RTBURBONSA-N O=C(Cc1ccccc1)Nc1nnc(C[C@@H]2[C@@H](Cc3nnc(NC(Cc4ccccc4)=O)[s]3)C2)[s]1 Chemical compound O=C(Cc1ccccc1)Nc1nnc(C[C@@H]2[C@@H](Cc3nnc(NC(Cc4ccccc4)=O)[s]3)C2)[s]1 HROAFZLZQSBWII-RTBURBONSA-N 0.000 description 1
- IYDQQEVMJHDYHS-OALUTQOASA-N O=C(Cc1ccccc1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3cccc(N(C4)CC4(F)F)n3)=O)[s]2)[s]1 Chemical compound O=C(Cc1ccccc1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3cccc(N(C4)CC4(F)F)n3)=O)[s]2)[s]1 IYDQQEVMJHDYHS-OALUTQOASA-N 0.000 description 1
- IEQQLBZADPWICO-PMACEKPBSA-N O=C(Cc1nc(N2CCC2)ccc1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3cccc(N4CCC4)n3)=O)[s]2)[s]1 Chemical compound O=C(Cc1nc(N2CCC2)ccc1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3cccc(N4CCC4)n3)=O)[s]2)[s]1 IEQQLBZADPWICO-PMACEKPBSA-N 0.000 description 1
- AGGLFYIKNHWBEV-GJZGRUSLSA-N O=C(Cc1ncccc1)Nc1nnc([C@@H](CC2)C[C@H]2c2nnc(NC(Cc3ccccn3)=O)[s]2)[s]1 Chemical compound O=C(Cc1ncccc1)Nc1nnc([C@@H](CC2)C[C@H]2c2nnc(NC(Cc3ccccn3)=O)[s]2)[s]1 AGGLFYIKNHWBEV-GJZGRUSLSA-N 0.000 description 1
- MAUKIMUELFDNSU-KBPBESRZSA-N O=C(Cc1ncccn1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ncccn3)=O)[s]2)[s]1 Chemical compound O=C(Cc1ncccn1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ncccn3)=O)[s]2)[s]1 MAUKIMUELFDNSU-KBPBESRZSA-N 0.000 description 1
- IYHMKSBMAHJAAQ-KBPBESRZSA-N O=C(Cc1ncncc1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ccncn3)=O)[s]2)[s]1 Chemical compound O=C(Cc1ncncc1)Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ccncn3)=O)[s]2)[s]1 IYHMKSBMAHJAAQ-KBPBESRZSA-N 0.000 description 1
- GQKUYGIUWMOAFW-VXKWHMMOSA-N OCc1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(CO)ccc4)=O)[s]3)[s]2)=O)ccc1 Chemical compound OCc1cc(CC(Nc2nnc([C@@H](CCC3)C[C@H]3c3nnc(NC(Cc4cc(CO)ccc4)=O)[s]3)[s]2)=O)ccc1 GQKUYGIUWMOAFW-VXKWHMMOSA-N 0.000 description 1
- DHVXIMURILYPRM-RXJZEZJSSA-N O[C@@H](C(Nc1nnc([C@@H](CCC2)CC2c2nnc(NC(Cc3cccc(N(C4)CC4(F)F)n3)=O)[s]2)[s]1)=O)c1ccccc1 Chemical compound O[C@@H](C(Nc1nnc([C@@H](CCC2)CC2c2nnc(NC(Cc3cccc(N(C4)CC4(F)F)n3)=O)[s]2)[s]1)=O)c1ccccc1 DHVXIMURILYPRM-RXJZEZJSSA-N 0.000 description 1
- UGZTYDXKDJDDPH-IRFCIJBXSA-N O[C@@H](C(Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ccccc3)=O)[s]2)[s]1)=O)c1ccccc1 Chemical compound O[C@@H](C(Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ccccc3)=O)[s]2)[s]1)=O)c1ccccc1 UGZTYDXKDJDDPH-IRFCIJBXSA-N 0.000 description 1
- UGZTYDXKDJDDPH-ZJOUEHCJSA-N O[C@H](C(Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ccccc3)=O)[s]2)[s]1)=O)c1ccccc1 Chemical compound O[C@H](C(Nc1nnc([C@@H](CCC2)C[C@H]2c2nnc(NC(Cc3ccccc3)=O)[s]2)[s]1)=O)c1ccccc1 UGZTYDXKDJDDPH-ZJOUEHCJSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2018202954A AU2018202954A1 (en) | 2012-11-22 | 2018-04-30 | Compounds and their methods of use |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2012/085023 WO2014079011A1 (en) | 2012-11-22 | 2012-11-22 | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
| AUPCT/CN2012/085023 | 2012-11-22 | ||
| PCT/CN2013/000294 WO2014079136A1 (en) | 2012-11-22 | 2013-03-15 | Compounds, pharmaceutical compositions and uses as glutaminase inhibitors for treating cancers thereof |
| AUPCT/CN2013/000294 | 2013-03-15 | ||
| PCT/CN2013/001428 WO2014079150A1 (en) | 2012-11-22 | 2013-11-21 | Compounds and their methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018202954A Division AU2018202954A1 (en) | 2012-11-22 | 2018-04-30 | Compounds and their methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2013347771A1 AU2013347771A1 (en) | 2015-06-11 |
| AU2013347771B2 true AU2013347771B2 (en) | 2018-02-01 |
Family
ID=50775393
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013347771A Ceased AU2013347771B2 (en) | 2012-11-22 | 2013-11-21 | Compounds and their methods of use |
| AU2018202954A Abandoned AU2018202954A1 (en) | 2012-11-22 | 2018-04-30 | Compounds and their methods of use |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018202954A Abandoned AU2018202954A1 (en) | 2012-11-22 | 2018-04-30 | Compounds and their methods of use |
Country Status (36)
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8604016B2 (en) | 2011-11-21 | 2013-12-10 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| KR102220175B1 (ko) | 2012-11-16 | 2021-02-24 | 칼리테라 바이오사이언시즈, 인코포레이티드 | 헤테로사이클릭 글루타미나아제 억제제 |
| EA029531B1 (ru) | 2012-11-21 | 2018-04-30 | Аджиос Фармасьютикалз, Инк. | Соединения, ингибирующие глутаминазу, и содержащие эти соединения фармацевтические композиции и их применение |
| WO2014079011A1 (en) | 2012-11-22 | 2014-05-30 | Agios Pharmaceuticals, Inc. | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
| MX2015006939A (es) * | 2012-12-03 | 2015-09-08 | Calithera Biosciences Inc | Tratamiento de cancer con inhibidores heterociclicos de glutaminasa. |
| EP2943485B1 (en) | 2013-01-14 | 2017-09-20 | Incyte Holdings Corporation | Bicyclic aromatic carboxamide compounds useful as pim kinase inhibitors |
| PE20191245A1 (es) | 2013-01-15 | 2019-09-18 | Incyte Holdings Corp | Compuestos de tiazolcarboxamidas y piridinacarboxamida utiles como inhibidores de quinasa pim |
| CN105658653A (zh) | 2013-08-23 | 2016-06-08 | 因赛特公司 | 可用作pim激酶抑制剂的呋喃并-和噻吩并-吡啶甲酰胺化合物 |
| CN111393431A (zh) | 2014-01-06 | 2020-07-10 | 理森制药股份公司 | 谷氨酰胺酶抑制剂 |
| CN106231900B (zh) * | 2014-03-21 | 2019-05-28 | 阿吉奥斯制药公司 | 化合物及其使用方法 |
| ES2759434T3 (es) * | 2014-04-30 | 2020-05-11 | Pfizer | Derivados de diheterociclo unidos a cicloalquilo |
| GB201409624D0 (en) | 2014-05-30 | 2014-07-16 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| CN107074805B (zh) | 2014-07-03 | 2021-02-26 | 德州大学系统董事会 | 用于治疗疾病的gls1抑制剂 |
| WO2016010897A1 (en) | 2014-07-14 | 2016-01-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as pim kinase inhibitors |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| WO2016014890A1 (en) * | 2014-07-24 | 2016-01-28 | Calithera Biosciences, Inc. | Treatment of multiple myeloma with heterocyclic inhibitors of glutaminase |
| WO2016022969A1 (en) | 2014-08-07 | 2016-02-11 | Calithera Biosciences, Inc. | Crystal forms of glutaminase inhibitors |
| US10245254B2 (en) | 2014-10-03 | 2019-04-02 | University of Pittsburgh—of the Commonwealth System of Higher Education | Glutaminase inhibitors |
| CA2981762A1 (en) | 2015-04-06 | 2016-10-13 | Calithera Biosciences, Inc. | Treatment of lung cancer with inhibitors of glutaminase |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| EP3316887B1 (en) * | 2015-06-30 | 2020-04-08 | Board of Regents, The University of Texas System | Gls1 inhibitors for treating disease |
| AR105967A1 (es) | 2015-09-09 | 2017-11-29 | Incyte Corp | Sales de un inhibidor de pim quinasa |
| US9920032B2 (en) | 2015-10-02 | 2018-03-20 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| US10258619B2 (en) | 2015-10-05 | 2019-04-16 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors and immuno-oncology agents |
| TW201731511A (zh) * | 2015-11-30 | 2017-09-16 | 阿斯特捷利康公司 | １，３，４-噻二唑化合物及其在治療癌症中之用途 |
| CN106890184B (zh) * | 2015-12-18 | 2019-06-25 | 诺言医药科技(上海)有限公司 | 抗肿瘤的谷氨酰胺酶抑制剂和肿瘤血管生成抑制剂药物组合物及其应用 |
| JP6976248B2 (ja) | 2015-12-22 | 2021-12-08 | ボード オブ リージェンツ、ザ ユニバーシテイ オブ テキサス システム | （ｒ）−１−（４−（６−（２−（４−（３，３−ジフルオロシクロブトキシ）−６−メチルピリジン−２−イル）アセトアミド）ピリダジン−３−イル）−２−フルオロブチル）−ｎ−メチル−１ｈ−１，２，３−トリアゾール−４−カルボキサミドの塩形態および多形体 |
| WO2018039441A1 (en) | 2016-08-25 | 2018-03-01 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| KR20190040302A (ko) * | 2016-08-25 | 2019-04-17 | 칼리테라 바이오사이언시즈, 인코포레이티드 | 글루타미나제 억제제와의 병용 요법 |
| EP3697764B1 (en) | 2017-10-18 | 2025-06-11 | Board Of Regents, The University Of Texas System | Gls-1 inhibitors for use in the treatment of cancer |
| AR113922A1 (es) | 2017-12-08 | 2020-07-01 | Incyte Corp | Terapia de combinación de dosis baja para el tratamiento de neoplasias mieloproliferativas |
| CA3102279A1 (en) | 2018-06-01 | 2019-12-05 | Cornell University | Combination therapy for pi3k-associated disease or disorder |
| WO2020096916A2 (en) | 2018-11-08 | 2020-05-14 | Merck Sharp & Dohme Corp. | Inhibitors of histone deacetylase useful for the treatment or prevention of hiv infection |
| WO2020191356A1 (en) * | 2019-03-21 | 2020-09-24 | Goncalves Marcus | Anti-fructose therapy for colorectal and small intestine cancers |
| CN110746416A (zh) * | 2019-09-05 | 2020-02-04 | 中国药科大学 | 含有三氮唑结构的谷氨酰胺酶gls1抑制剂或其可药用的盐、其制备方法及用途 |
| CN112898200A (zh) * | 2021-01-20 | 2021-06-04 | 都创(上海)医药科技股份有限公司 | 5-溴-6-甲氧基吡啶-2-羧酸酯的合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013078123A1 (en) * | 2011-11-21 | 2013-05-30 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2037257A1 (en) | 1970-07-28 | 1972-02-03 | Farbwerke Hoechst AG, vorm. Meister Lucius & Brüning, 6000 Frankfurt | Poly-(5-amino-1,3,4-thiadiazol-2-yl) derivs prepn - intermediates for drug and polymer prodn |
| US4070400A (en) | 1975-10-16 | 1978-01-24 | Merck & Co., Inc. | Diphenyl polyamides having a cyclohexylene moiety |
| US4376110A (en) | 1980-08-04 | 1983-03-08 | Hybritech, Incorporated | Immunometric assays using monoclonal antibodies |
| US4366241A (en) | 1980-08-07 | 1982-12-28 | Syva Company | Concentrating zone method in heterogeneous immunoassays |
| US4517288A (en) | 1981-01-23 | 1985-05-14 | American Hospital Supply Corp. | Solid phase system for ligand assay |
| CA1291031C (en) | 1985-12-23 | 1991-10-22 | Nikolaas C.J. De Jaeger | Method for the detection of specific binding agents and their correspondingbindable substances |
| US4843155A (en) | 1987-11-19 | 1989-06-27 | Piotr Chomczynski | Product and process for isolating RNA |
| SU1761672A1 (ru) * | 1990-05-22 | 1992-09-15 | Белгородский технологический институт строительных материалов им.И.А.Гришманова | Способ получени тонкодисперсного мела |
| CA2155759A1 (en) | 1993-03-29 | 1994-10-13 | Bernd Janssen | 1-amino-3-phenoxy propane derivatives as modulators of multi-drug resistance |
| US5895748A (en) | 1996-11-27 | 1999-04-20 | Johnson; Keith R. | Panel of antibodies for detecting cadherins and catenins in tissues and method of using the panel of antibodies |
| JP2002518380A (ja) * | 1998-06-18 | 2002-06-25 | ブリストル−マイヤーズ スクイブ カンパニー | サイクリン依存キナーゼの炭素置換アミノチアゾール抑制剤 |
| EP1388734B1 (en) | 2002-08-01 | 2004-03-03 | MTM Laboratories AG | Method for solution based diagnosis |
| AU3316600A (en) | 1999-02-22 | 2000-09-21 | Torben F. Orntoft | Gene expression in bladder tumors |
| US20030054985A1 (en) | 2000-02-22 | 2003-03-20 | Stuart Aaronson | N-cadherin modulated migration, invasion, and metastasis |
| US6974667B2 (en) | 2000-06-14 | 2005-12-13 | Gene Logic, Inc. | Gene expression profiles in liver cancer |
| US6451828B1 (en) * | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| WO2006040569A1 (en) | 2004-10-14 | 2006-04-20 | Astex Therapeutics Limited | Thiophene amide compounds for use in the treatment or prophylaxis of cancers |
| US20080182865A1 (en) | 2005-03-11 | 2008-07-31 | Witta Samir E | Histone deacetylase inhibitors sensitize cancer cells to epidermal growth factor inhibitors |
| ATE477495T1 (de) | 2005-03-16 | 2010-08-15 | Osi Pharm Inc | Biologische marker prediktiv für das ansprechen von krebs auf inhibitoren der kinase des rezeptors für epidermalen wachstumsfaktor |
| US8716472B2 (en) | 2006-10-16 | 2014-05-06 | University Of Rochester | Tripodal cyclohexane derivatives and their use as carbohydrate receptors |
| US8563695B2 (en) | 2007-11-19 | 2013-10-22 | Genentech, Inc. | Antibodies that bind β2 |
| JP2011516826A (ja) | 2008-03-07 | 2011-05-26 | オーエスアイ・フアーマスーテイカルズ・インコーポレーテツド | 間葉系様腫瘍細胞またはこの形成を阻害する作用剤の同定のための方法 |
| EP2399129B1 (en) | 2009-02-20 | 2015-11-25 | Michael P. Lisanti | A method of diagnosis or prognosis of a neoplasm comprising determining the level of expression of a protein in stromal cells adjacent to the neoplasm |
| WO2010111504A2 (en) | 2009-03-25 | 2010-09-30 | Cornell University | Inhibition of glutaminase c |
| WO2010120966A1 (en) | 2009-04-17 | 2010-10-21 | Osi Pharmaceuticals, Inc. | Biological markers predictive of anti-cancer response to epidermal growth factor receptor kinase inhibitors |
| US20130109643A1 (en) * | 2010-05-10 | 2013-05-02 | The Johns Hopkins University | Metabolic inhibitor against tumors having an idh mutation |
| US20130109592A1 (en) | 2010-06-23 | 2013-05-02 | University Of Louisville Research Foundation, Inc. | Methods for detecting cancer |
| US10064885B2 (en) | 2010-07-09 | 2018-09-04 | Massachusetts Institute Of Technology | Metabolic gene, enzyme, and flux targets for cancer therapy |
| UY33930A (es) | 2011-03-04 | 2012-10-31 | Novartis Ag | Inhibidores novedosos de quinasas |
| CN102827073A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| JP2015514062A (ja) | 2012-03-15 | 2015-05-18 | ザ リサーチ ファウンデーション フォー ザ ステイト ユニバーシティ オブ ニューヨーク | Ｅ−カドヘリンの細胞外ドメインの阻害剤を含む併用療法 |
| EA029531B1 (ru) | 2012-11-21 | 2018-04-30 | Аджиос Фармасьютикалз, Инк. | Соединения, ингибирующие глутаминазу, и содержащие эти соединения фармацевтические композиции и их применение |
| WO2014079011A1 (en) | 2012-11-22 | 2014-05-30 | Agios Pharmaceuticals, Inc. | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
| US9029531B2 (en) | 2012-11-22 | 2015-05-12 | Agios Pharmaceuticals, Inc. | Compounds and their methods of use |
| US20160008380A1 (en) | 2013-03-06 | 2016-01-14 | The Johns Hopkins University | Targeting glutamine metabolism in brain tumors |
| CN111393431A (zh) | 2014-01-06 | 2020-07-10 | 理森制药股份公司 | 谷氨酰胺酶抑制剂 |
| CN106231900B (zh) | 2014-03-21 | 2019-05-28 | 阿吉奥斯制药公司 | 化合物及其使用方法 |
-
2012
- 2012-11-22 WO PCT/CN2012/085023 patent/WO2014079011A1/en not_active Ceased
-
2013
- 2013-03-15 WO PCT/CN2013/000294 patent/WO2014079136A1/en not_active Ceased
- 2013-11-21 DK DK13857585.7T patent/DK2922850T3/en active
- 2013-11-21 UA UAA201506066A patent/UA117360C2/uk unknown
- 2013-11-21 EA EA201590987A patent/EA030646B1/ru not_active IP Right Cessation
- 2013-11-21 EA EA201890754A patent/EA201890754A1/ru unknown
- 2013-11-21 PE PE2015000674A patent/PE20151072A1/es unknown
- 2013-11-21 US US14/646,634 patent/US10087172B2/en active Active
- 2013-11-21 JP JP2015543242A patent/JP6333277B2/ja not_active Expired - Fee Related
- 2013-11-21 RS RS20181133A patent/RS57859B1/sr unknown
- 2013-11-21 SG SG11201504049VA patent/SG11201504049VA/en unknown
- 2013-11-21 PL PL13857585T patent/PL2922850T3/pl unknown
- 2013-11-21 TR TR2018/12360T patent/TR201812360T4/tr unknown
- 2013-11-21 EP EP18183580.2A patent/EP3456719A1/en not_active Withdrawn
- 2013-11-21 PT PT13857585T patent/PT2922850T/pt unknown
- 2013-11-21 CA CA2893510A patent/CA2893510C/en active Active
- 2013-11-21 KR KR1020157016414A patent/KR20150085079A/ko not_active Ceased
- 2013-11-21 MY MYPI2015001355A patent/MY177344A/en unknown
- 2013-11-21 NZ NZ708382A patent/NZ708382A/en unknown
- 2013-11-21 HU HUE13857585A patent/HUE040111T2/hu unknown
- 2013-11-21 CN CN201380070365.5A patent/CN104936954B/zh not_active Expired - Fee Related
- 2013-11-21 SG SG10201609940RA patent/SG10201609940RA/en unknown
- 2013-11-21 EP EP13857585.7A patent/EP2922850B1/en active Active
- 2013-11-21 CN CN201810824418.2A patent/CN108727307A/zh active Pending
- 2013-11-21 AU AU2013347771A patent/AU2013347771B2/en not_active Ceased
- 2013-11-21 SM SM20180504T patent/SMT201800504T1/it unknown
- 2013-11-21 MX MX2015006493A patent/MX367389B/es active IP Right Grant
- 2013-11-21 WO PCT/CN2013/001428 patent/WO2014079150A1/en not_active Ceased
- 2013-11-21 LT LTEP13857585.7T patent/LT2922850T/lt unknown
- 2013-11-21 HR HRP20181628TT patent/HRP20181628T1/hr unknown
- 2013-11-21 ES ES13857585.7T patent/ES2690390T3/es active Active
- 2013-11-21 SI SI201331140T patent/SI2922850T1/sl unknown
- 2013-11-21 BR BR112015011830A patent/BR112015011830A2/pt not_active Application Discontinuation
- 2013-11-22 TW TW107111990A patent/TW201906825A/zh unknown
- 2013-11-22 TW TW102142566A patent/TWI629268B/zh not_active IP Right Cessation
- 2013-11-22 AR ARP130104322A patent/AR093598A1/es unknown
-
2015
- 2015-05-21 IL IL238958A patent/IL238958B/en not_active IP Right Cessation
- 2015-05-22 PH PH12015501150A patent/PH12015501150B1/en unknown
- 2015-05-22 CL CL2015001392A patent/CL2015001392A1/es unknown
- 2015-05-22 SA SA515360469A patent/SA515360469B1/ar unknown
- 2015-06-15 CR CR20150316A patent/CR20150316A/es unknown
- 2015-06-22 EC ECIEPI201526557A patent/ECSP15026557A/es unknown
-
2017
- 2017-11-24 PH PH12017502141A patent/PH12017502141A1/en unknown
-
2018
- 2018-04-24 JP JP2018082754A patent/JP2018150316A/ja active Pending
- 2018-04-30 AU AU2018202954A patent/AU2018202954A1/en not_active Abandoned
- 2018-08-17 CY CY20181100864T patent/CY1120581T1/el unknown
- 2018-08-21 US US16/107,220 patent/US10689375B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013078123A1 (en) * | 2011-11-21 | 2013-05-30 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2013347771B2 (en) | Compounds and their methods of use | |
| US9029531B2 (en) | Compounds and their methods of use | |
| AU2013347933C1 (en) | Glutaminase inhibitors and methods of use | |
| AU2015231053B2 (en) | Compounds and their methods of use | |
| HK1214593B (en) | Compounds and their methods of use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: LES LABORATOIRES SERVIER SAS Free format text: FORMER OWNER(S): AGIOS PHARMACEUTICALS, INC. |
|
| DA2 | Applications for amendment section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE NAME OF THE PATENTEE TO READ LES LABORATOIRES SERVIER |
|
| HB | Alteration of name in register |
Owner name: LES LABORATOIRES SERVIER Free format text: FORMER NAME(S): LES LABORATOIRES SERVIER SAS |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |