JP5755731B2 - Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体のｃ−２８アミド - Google Patents
Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体のｃ−２８アミド Download PDFInfo
- Publication number
- JP5755731B2 JP5755731B2 JP2013513340A JP2013513340A JP5755731B2 JP 5755731 B2 JP5755731 B2 JP 5755731B2 JP 2013513340 A JP2013513340 A JP 2013513340A JP 2013513340 A JP2013513340 A JP 2013513340A JP 5755731 B2 JP5755731 B2 JP 5755731B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- cyclopenta
- pentamethyl
- substituted
- 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.)
- Expired - Fee Related
Links
- 0 CC(C)([C@]1CC2)C(C(*)[U]C(*)C(O)=O)=CC[C@]1(C)[C@@](CC1)[C@]2(C)[C@@]2(C)[C@]1[C@@]([C@](*)CC1)[C@@]1(*)CC2 Chemical compound CC(C)([C@]1CC2)C(C(*)[U]C(*)C(O)=O)=CC[C@]1(C)[C@@](CC1)[C@]2(C)[C@@]2(C)[C@]1[C@@]([C@](*)CC1)[C@@]1(*)CC2 0.000 description 7
- RBKAZZIJGKVWQX-ZHOFKQHZSA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c(cc2)ccc2C(O)=O)[C@]13C(NCCN(C)C)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c(cc2)ccc2C(O)=O)[C@]13C(NCCN(C)C)=O RBKAZZIJGKVWQX-ZHOFKQHZSA-N 0.000 description 3
- ZQJMRLTWLKCXLF-WECSNRJHSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N(C)CCN(C)C)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N(C)CCN(C)C)=O ZQJMRLTWLKCXLF-WECSNRJHSA-N 0.000 description 2
- YYKWJXFSVOBNNK-RVOCSARKSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CC(O)=O)c1ccccc1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CC(O)=O)c1ccccc1)=O YYKWJXFSVOBNNK-RVOCSARKSA-N 0.000 description 2
- SJDINYHFHWSDCG-BDYKDQQASA-N CC(C)([C@@H]1CC2)C(c(ccc(C(O)=O)c3)c3F)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CC1)CCS1(=O)=O)=O Chemical compound CC(C)([C@@H]1CC2)C(c(ccc(C(O)=O)c3)c3F)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CC1)CCS1(=O)=O)=O SJDINYHFHWSDCG-BDYKDQQASA-N 0.000 description 2
- IYXWIGIBQRBZEA-SOPZNGSOSA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c(cc2)ccc2C(O)=O)[C@]13C(NCCC(O)=O)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c(cc2)ccc2C(O)=O)[C@]13C(NCCC(O)=O)=O IYXWIGIBQRBZEA-SOPZNGSOSA-N 0.000 description 2
- REUSEPFORFXNQD-AXODBVIISA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c(cc2)ccc2C(O)=O)[C@]13C(NCCc1ccccn1)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c(cc2)ccc2C(O)=O)[C@]13C(NCCc1ccccn1)=O REUSEPFORFXNQD-AXODBVIISA-N 0.000 description 2
- YJXVZBXAWFVTPL-MFUKUDMTSA-N CC(C)(C)OC(N1CCN(CCNC([C@@](CC[C@H]2C(C)=C)(CC3)[C@H]2[C@@H](CC2)[C@]3(C)[C@](C)(CC3)[C@H]2[C@]2(C)[C@@H]3C(C)(C)C(c(cc3)ccc3C(O)=O)=CC2)=O)CC1)=O Chemical compound CC(C)(C)OC(N1CCN(CCNC([C@@](CC[C@H]2C(C)=C)(CC3)[C@H]2[C@@H](CC2)[C@]3(C)[C@](C)(CC3)[C@H]2[C@]2(C)[C@@H]3C(C)(C)C(c(cc3)ccc3C(O)=O)=CC2)=O)CC1)=O YJXVZBXAWFVTPL-MFUKUDMTSA-N 0.000 description 1
- PLWLVOBLJPYYJO-DTIOYNMSSA-N CC(C)(CCC(C)(C1)N)[C@@]1(C)NC Chemical compound CC(C)(CCC(C)(C1)N)[C@@]1(C)NC PLWLVOBLJPYYJO-DTIOYNMSSA-N 0.000 description 1
- GEGZCOBMYHMNDO-LNXAQSDPSA-N CC(C)([C@@H]1CC2)C(c(cc3)cc(C(O)=O)c3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(C)C)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)cc(C(O)=O)c3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(C)C)=O GEGZCOBMYHMNDO-LNXAQSDPSA-N 0.000 description 1
- JDGSDCHJHNHEDO-RWQDOXMISA-N CC(C)([C@@H]1CC2)C(c(cc3)cc(F)c3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(C)C)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)cc(F)c3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(C)C)=O JDGSDCHJHNHEDO-RWQDOXMISA-N 0.000 description 1
- JXFOBAQEYMBCPX-PQBBHEMQSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C(C)=C)=C)[C@@]21C(NCCN(C)C)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C(C)=C)=C)[C@@]21C(NCCN(C)C)=O JXFOBAQEYMBCPX-PQBBHEMQSA-N 0.000 description 1
- XRBQLYYEQKCQAE-LTJMNYHZSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C(C)=C)=C)[C@@]21C(NCCN1CCOCC1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C(C)=C)=C)[C@@]21C(NCCN1CCOCC1)=O XRBQLYYEQKCQAE-LTJMNYHZSA-N 0.000 description 1
- PTFCXDOCSKBATK-LTJMNYHZSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N(C)Cc1ccccc1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N(C)Cc1ccccc1)=O PTFCXDOCSKBATK-LTJMNYHZSA-N 0.000 description 1
- WHQWHUPNDJYFGB-WECSNRJHSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N1CCCCC1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N1CCCCC1)=O WHQWHUPNDJYFGB-WECSNRJHSA-N 0.000 description 1
- RLGPBYSVAHZOIS-WECSNRJHSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N1CCN(C)CC1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N1CCN(C)CC1)=O RLGPBYSVAHZOIS-WECSNRJHSA-N 0.000 description 1
- JMHUPTJKLABXEL-PQBBHEMQSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCCN(C)C(C)=O)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCCN(C)C(C)=O)=O JMHUPTJKLABXEL-PQBBHEMQSA-N 0.000 description 1
- IRERPUDTJLCLKC-WECSNRJHSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCCNC(C)=O)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCCNC(C)=O)=O IRERPUDTJLCLKC-WECSNRJHSA-N 0.000 description 1
- YXUQPFRGKSGEHC-WECSNRJHSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(C)C(C)=O)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(C)C(C)=O)=O YXUQPFRGKSGEHC-WECSNRJHSA-N 0.000 description 1
- UXZPRKAHCBPPDA-LYJCWSOSSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(C)C)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(C)C)=O UXZPRKAHCBPPDA-LYJCWSOSSA-N 0.000 description 1
- FUZHUQVOFWOYRT-RPSIQIFRSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CCC1)C1=O)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CCC1)C1=O)=O FUZHUQVOFWOYRT-RPSIQIFRSA-N 0.000 description 1
- UOXNIQRWLJYACR-RPAAZHKCSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN1CCN(C)CC1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN1CCN(C)CC1)=O UOXNIQRWLJYACR-RPAAZHKCSA-N 0.000 description 1
- ROJVPBPNULKQDR-LTJMNYHZSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCNc1ccccc1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCNc1ccccc1)=O ROJVPBPNULKQDR-LTJMNYHZSA-N 0.000 description 1
- MCVLIRRGFKHSAN-YDDYIPHKSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCO)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCO)=O MCVLIRRGFKHSAN-YDDYIPHKSA-N 0.000 description 1
- CAOWSZFTYZRODW-LTJMNYHZSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCc(cc1)ccc1OC)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCc(cc1)ccc1OC)=O CAOWSZFTYZRODW-LTJMNYHZSA-N 0.000 description 1
- CTGWPEWGABBAHV-PQBBHEMQSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCc1ccncc1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCc1ccncc1)=O CTGWPEWGABBAHV-PQBBHEMQSA-N 0.000 description 1
- ZJOLTRNFKJNUEJ-NFEAHYNFSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCc1ncc[nH]1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCc1ncc[nH]1)=O ZJOLTRNFKJNUEJ-NFEAHYNFSA-N 0.000 description 1
- AKNFOZKWGXFCFE-NDPXXONMSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCN(C)CCO)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCN(C)CCO)=O AKNFOZKWGXFCFE-NDPXXONMSA-N 0.000 description 1
- DKVSQQCPFBRTQK-OHRNCGRDSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCNCCO)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCNCCO)=O DKVSQQCPFBRTQK-OHRNCGRDSA-N 0.000 description 1
- ADNGUFJHARODKQ-ILCYPOACSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCNc1ccccc1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCNc1ccccc1)=O ADNGUFJHARODKQ-ILCYPOACSA-N 0.000 description 1
- LWSOXVHDMHNNDU-FZYCCUIASA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCOC)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCOC)=O LWSOXVHDMHNNDU-FZYCCUIASA-N 0.000 description 1
- KGKBFKAOAUZIFR-RPAAZHKCSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(OC)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCCN(C)C(C)=O)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(OC)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCCN(C)C(C)=O)=O KGKBFKAOAUZIFR-RPAAZHKCSA-N 0.000 description 1
- CARQFZMOHADUKC-BDYKDQQASA-N CC(C)([C@@H]1CC2)C(c(ccc(C(O)=O)c3)c3F)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CC1)CCC1(F)F)=O Chemical compound CC(C)([C@@H]1CC2)C(c(ccc(C(O)=O)c3)c3F)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CC1)CCC1(F)F)=O CARQFZMOHADUKC-BDYKDQQASA-N 0.000 description 1
- BNYFRFZRHWQDIQ-YLJBMROHSA-N CC(C)([C@@H]1CC2)C(c(ccc(C(O)=O)c3)c3F)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCN(CC1)CCC1(F)F)=O Chemical compound CC(C)([C@@H]1CC2)C(c(ccc(C(O)=O)c3)c3F)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21C(NCCN(CC1)CCC1(F)F)=O BNYFRFZRHWQDIQ-YLJBMROHSA-N 0.000 description 1
- VVHCSEKVBZTRRH-RPSIQIFRSA-N CC(C)([C@@H]1CC2)C(c3ccc(C(O)O)cc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CCC1)C1=O)=O Chemical compound CC(C)([C@@H]1CC2)C(c3ccc(C(O)O)cc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(NCCN(CCC1)C1=O)=O VVHCSEKVBZTRRH-RPSIQIFRSA-N 0.000 description 1
- GOXDHWRKTLQGMG-BWAJZPSWSA-N CC(C)([C@@H]1CC2)C(c3ccc(C(O)O)cc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N[C@@H](Cc1ccccc1)C(O)=O)=O Chemical compound CC(C)([C@@H]1CC2)C(c3ccc(C(O)O)cc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(N[C@@H](Cc1ccccc1)C(O)=O)=O GOXDHWRKTLQGMG-BWAJZPSWSA-N 0.000 description 1
- ZUSGPADKQOUQCH-GSWCUGAVSA-N CC(C)C[C@@H](C(O)=O)NC([C@@](CC[C@H]1C(C)=C)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(c(cc2)ccc2C(O)=O)=CC1)=O Chemical compound CC(C)C[C@@H](C(O)=O)NC([C@@](CC[C@H]1C(C)=C)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(c(cc2)ccc2C(O)=O)=CC1)=O ZUSGPADKQOUQCH-GSWCUGAVSA-N 0.000 description 1
- CJEBDIAEJSHYHU-ADLZBGDZSA-N CC(C)[C@H](CC1)C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)C2[C@]2(C)C4C(C)(C)C(c(cc4)ccc4C(OC)=O)=CC2)[C@]13C(O)=O Chemical compound CC(C)[C@H](CC1)C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)C2[C@]2(C)C4C(C)(C)C(c(cc4)ccc4C(OC)=O)=CC2)[C@]13C(O)=O CJEBDIAEJSHYHU-ADLZBGDZSA-N 0.000 description 1
- CKIYFPRGTJXTKI-CCNIEAMXSA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c(cc2)ccc2C(OC)=O)[C@]13C(Cl)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c(cc2)ccc2C(OC)=O)[C@]13C(Cl)=O CKIYFPRGTJXTKI-CCNIEAMXSA-N 0.000 description 1
- ADBVTNHLSCIOBK-WECSNRJHSA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(c(cc4)ccc4C(OC)=O)=CC2)[C@]13C(NCCN(C)C)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(c(cc4)ccc4C(OC)=O)=CC2)[C@]13C(NCCN(C)C)=O ADBVTNHLSCIOBK-WECSNRJHSA-N 0.000 description 1
- CHDVFHGMKRKZJV-MSEMWXCYSA-N CCCN(CCNC([C@@](CC[C@H]1C(C)=C)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(c(cc2)ccc2C(OC)=O)=CC1)=O)CC(OC)=O Chemical compound CCCN(CCNC([C@@](CC[C@H]1C(C)=C)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(c(cc2)ccc2C(OC)=O)=CC1)=O)CC(OC)=O CHDVFHGMKRKZJV-MSEMWXCYSA-N 0.000 description 1
- UTHUAKCBRXCAOS-TYPDTNHVSA-N C[C@@H](C(O)=O)NC([C@@](CC[C@H]1C(C)=C)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(c(cc2)ccc2C(O)=O)=CC1)=O Chemical compound C[C@@H](C(O)=O)NC([C@@](CC[C@H]1C(C)=C)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(c(cc2)ccc2C(O)=O)=CC1)=O UTHUAKCBRXCAOS-TYPDTNHVSA-N 0.000 description 1
- FUFAPKOCRZYSHH-CVTBAMPXSA-N C[C@H](CC1)[C@H](C)[C@H]2C3=CC[C@H]([C@@](C)(CC4)[C@@H](CC5)C(C)(C)[C@H]4O)[C@]5(C)[C@]3(C)CC[C@@]12C(OCc1ccccc1)=O Chemical compound C[C@H](CC1)[C@H](C)[C@H]2C3=CC[C@H]([C@@](C)(CC4)[C@@H](CC5)C(C)(C)[C@H]4O)[C@]5(C)[C@]3(C)CC[C@@]12C(OCc1ccccc1)=O FUFAPKOCRZYSHH-CVTBAMPXSA-N 0.000 description 1
- VGZBAUXKFOTNDN-KBSNOELUSA-N C[C@H](CC[C@@](CC1)([C@@H](CCC2)[C@@H]1C(C)=C)C(N1CCN(CCO)CC1)=O)[C@](C)(CC1)[C@H]2[C@]2(C)[C@@H]1C(C)(C)C(c(cc1)ccc1C(O)=O)=CC2 Chemical compound C[C@H](CC[C@@](CC1)([C@@H](CCC2)[C@@H]1C(C)=C)C(N1CCN(CCO)CC1)=O)[C@](C)(CC1)[C@H]2[C@]2(C)[C@@H]1C(C)(C)C(c(cc1)ccc1C(O)=O)=CC2 VGZBAUXKFOTNDN-KBSNOELUSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35133210P | 2010-06-04 | 2010-06-04 | |
| US61/351,332 | 2010-06-04 | ||
| PCT/US2011/038884 WO2011153319A1 (en) | 2010-06-04 | 2011-06-02 | C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013527243A JP2013527243A (ja) | 2013-06-27 |
| JP2013527243A5 JP2013527243A5 (OSRAM) | 2014-07-17 |
| JP5755731B2 true JP5755731B2 (ja) | 2015-07-29 |
Family
ID=44627254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013513340A Expired - Fee Related JP5755731B2 (ja) | 2010-06-04 | 2011-06-02 | Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体のｃ−２８アミド |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8802661B2 (OSRAM) |
| EP (1) | EP2576586B1 (OSRAM) |
| JP (1) | JP5755731B2 (OSRAM) |
| CN (1) | CN102985438B (OSRAM) |
| AR (1) | AR081638A1 (OSRAM) |
| BR (1) | BR112012030810A2 (OSRAM) |
| CA (1) | CA2801491C (OSRAM) |
| DK (1) | DK2576586T3 (OSRAM) |
| EA (1) | EA026140B1 (OSRAM) |
| ES (1) | ES2548905T3 (OSRAM) |
| HR (1) | HRP20150977T1 (OSRAM) |
| HU (1) | HUE026662T2 (OSRAM) |
| MX (1) | MX2012013628A (OSRAM) |
| PL (1) | PL2576586T3 (OSRAM) |
| PT (1) | PT2576586E (OSRAM) |
| RS (1) | RS54239B1 (OSRAM) |
| SI (1) | SI2576586T1 (OSRAM) |
| SM (1) | SMT201500272B (OSRAM) |
| TW (1) | TW201201792A (OSRAM) |
| WO (1) | WO2011153319A1 (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG192144A1 (en) * | 2011-01-31 | 2013-08-30 | Bristol Myers Squibb Co | C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity |
| PL2670764T3 (pl) * | 2011-01-31 | 2016-02-29 | Bristol Myers Squibb Co | C-28 aminy zmodyfikowanych C-3 pochodnych kwasu betulinowego jako inhibitory dojrzewania HIV |
| SG11201400331WA (en) | 2011-09-21 | 2014-08-28 | Bristol Myers Squibb Co | Novel betulinic acid derivatives with antiviral activity |
| US8906889B2 (en) * | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| US8889854B2 (en) * | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| WO2014105926A1 (en) | 2012-12-31 | 2014-07-03 | Hetero Research Foundation | Novel betulinic acid proline derivatives as hiv inhibitors |
| JP6186010B2 (ja) * | 2013-02-06 | 2017-08-23 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｈｉｖ成熟阻害活性を有するｃ−１９修飾トリテルペノイド類 |
| BR112015019590A2 (pt) * | 2013-02-25 | 2017-07-18 | Bristol Myers Squibb Co | derivados de ácido betulínico modificado com c-3 alquila e alquenila úteis no tratamento de hiv |
| HUE051719T2 (hu) | 2014-04-11 | 2021-03-29 | Viiv Healthcare Uk No 4 Ltd | Triterpenoidok HIV érésgátló aktivitással, amelyek a 3-helyzetben egy halogénalkil-szubsztituenst hordozó nem-aromás gyûrûvel helyettesítettek |
| US9920090B2 (en) | 2014-06-19 | 2018-03-20 | VIIV Healthcare UK (No.5) Limited | Betulinic acid derivatives with HIV maturation inhibitory activity |
| WO2015198263A2 (en) * | 2014-06-26 | 2015-12-30 | Hetero Research Foundation | Novel betulinic proline substituted derivatives as hiv inhibitors |
| US20170129916A1 (en) | 2014-06-26 | 2017-05-11 | Hetero Research Foundation | Novel betulinic proline imidazole derivatives as hiv inhibitors |
| EP3218388A1 (en) | 2014-11-14 | 2017-09-20 | VIIV Healthcare UK (No.5) Limited | C17-aryl substituted betulinic acid analogs |
| RU2017118489A (ru) * | 2014-11-14 | 2018-12-14 | ВАЙВ ХЕЛТКЕР ЮКей (N5) ЛИМИТЕД | Оксолупеновые производные |
| MA40886B1 (fr) | 2015-02-09 | 2020-03-31 | Hetero Research Foundation | Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-28 en tant qu'inhibiteurs du vih |
| WO2016147099A2 (en) | 2015-03-16 | 2016-09-22 | Hetero Research Foundation | C-3 novel triterpenone with c-28 amide derivatives as hiv inhibitors |
| KR20180028535A (ko) | 2015-07-28 | 2018-03-16 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 감염을 예방하거나 치료하기 위한 베투인 유도체 |
| JP2018521093A (ja) | 2015-07-28 | 2018-08-02 | グラクソスミスクライン、インテレクチュアル、プロパティー、（ナンバー２）、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ （Ｎｏ．２） Ｌｉｍｉｔｅｄ | Ｈｉｖ感染を予防または治療するためのベツイン誘導体 |
| JP2018528231A (ja) * | 2015-09-24 | 2018-09-27 | グラクソスミスクライン、インテレクチュアル、プロパティー、（ナンバー２）、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ （Ｎｏ．２） Ｌｉｍｉｔｅｄ | Ｈｉｖ成熟阻害活性を有する化合物 |
| EP3405474A1 (en) | 2016-01-20 | 2018-11-28 | Glaxosmithkline Intellectual Property (No. 2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
| AR107512A1 (es) | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
| US20190135857A1 (en) * | 2016-06-30 | 2019-05-09 | Viiv Healthcare Uk (No. 5) Limited | Triterpenoid inhibitors of human immunodeficiency virus replication |
| EP4321164A3 (en) | 2018-04-24 | 2024-04-17 | ViiV Healthcare UK (No.5) Limited | Compounds with hiv maturation inhibitory activity |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
| US10343997B1 (en) | 2018-12-04 | 2019-07-09 | King Saud University | Ursolic acid derivatives |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| US5679828A (en) * | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| ES2281960T3 (es) * | 1998-03-02 | 2007-10-01 | The University Of North Carolina At Chapel Hill | Derivados acilados de betulina y dihidrobetulina, su preparacion y su uso. |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| ZA200502824B (en) * | 2002-09-26 | 2007-04-25 | Panacos Pharmaceuticals Inc | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| US20050014730A1 (en) | 2003-04-02 | 2005-01-20 | Carlson Robert M. | Anti-fungal formulation of triterpene and essential oil |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| CA2560266A1 (en) | 2004-03-17 | 2005-09-29 | Panacos Pharmaceuticals, Inc. | Pharmaceutical salts of 3-o-(3',3'-dimethylsuccinyl) betulinic acid |
| WO2005112929A2 (en) * | 2004-05-20 | 2005-12-01 | Cornell Research Foundation, Inc. | Anti-hiv-1 activity of betulinol derivatives |
| US7282521B2 (en) | 2004-05-24 | 2007-10-16 | University Of North Carolina At Chapel Hill | Anti-retroviral moronic acid derivatives |
| TW200628161A (en) * | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| WO2007098247A2 (en) * | 2006-02-21 | 2007-08-30 | Achillion Pharmaceuticals, Inc. | Substituted taraxastanes useful for treating viral infections |
| WO2008097341A2 (en) | 2006-07-26 | 2008-08-14 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| WO2008127364A2 (en) * | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| WO2008115281A2 (en) * | 2006-10-16 | 2008-09-25 | Myriad Genetics, Inc. | Compounds for treating viral infections |
| US20090062243A1 (en) * | 2007-08-03 | 2009-03-05 | Advanced Life Sciences, Inc. | Lupane-Type Triterpenoids Modified at 30-Position and Analogues Thereof |
| WO2009042166A1 (en) | 2007-09-25 | 2009-04-02 | Panacos Pharmaceuticals, Inc. | Liquid bevirimat dosage forms for oral administration |
| CA2714049A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17.beta. lupane derivatives |
| WO2009114083A2 (en) | 2008-03-03 | 2009-09-17 | Panacos Pharmaceuticals, Inc. | Determinants of antiviral response |
| BRPI0911422B8 (pt) * | 2008-04-18 | 2021-05-25 | Reata Pharmaceuticals Inc | compostos moduladores inflamatórios antioxidantes, composição farmacêutica e usos dos mesmos |
| WO2011100308A1 (en) * | 2010-02-11 | 2011-08-18 | Glaxosmithkline Llc | Derivatives of betulin |
-
2011
- 2011-06-02 ES ES11726564.5T patent/ES2548905T3/es active Active
- 2011-06-02 DK DK11726564.5T patent/DK2576586T3/en active
- 2011-06-02 RS RS20150587A patent/RS54239B1/sr unknown
- 2011-06-02 PL PL11726564T patent/PL2576586T3/pl unknown
- 2011-06-02 CA CA2801491A patent/CA2801491C/en not_active Expired - Fee Related
- 2011-06-02 JP JP2013513340A patent/JP5755731B2/ja not_active Expired - Fee Related
- 2011-06-02 US US13/151,722 patent/US8802661B2/en not_active Expired - Fee Related
- 2011-06-02 WO PCT/US2011/038884 patent/WO2011153319A1/en not_active Ceased
- 2011-06-02 HR HRP20150977TT patent/HRP20150977T1/hr unknown
- 2011-06-02 CN CN201180035812.4A patent/CN102985438B/zh not_active Expired - Fee Related
- 2011-06-02 HU HUE11726564A patent/HUE026662T2/en unknown
- 2011-06-02 EP EP11726564.5A patent/EP2576586B1/en active Active
- 2011-06-02 PT PT117265645T patent/PT2576586E/pt unknown
- 2011-06-02 SI SI201130604T patent/SI2576586T1/sl unknown
- 2011-06-02 EA EA201270800A patent/EA026140B1/ru not_active IP Right Cessation
- 2011-06-02 BR BR112012030810A patent/BR112012030810A2/pt not_active IP Right Cessation
- 2011-06-02 MX MX2012013628A patent/MX2012013628A/es active IP Right Grant
- 2011-06-03 TW TW100119710A patent/TW201201792A/zh unknown
- 2011-06-03 AR ARP110101945A patent/AR081638A1/es not_active Application Discontinuation
-
2015
- 2015-10-30 SM SM201500272T patent/SMT201500272B/it unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN102985438B (zh) | 2016-05-18 |
| CN102985438A (zh) | 2013-03-20 |
| HUE026662T2 (en) | 2016-06-28 |
| US8802661B2 (en) | 2014-08-12 |
| PL2576586T3 (pl) | 2016-01-29 |
| RS54239B1 (sr) | 2015-12-31 |
| WO2011153319A1 (en) | 2011-12-08 |
| MX2012013628A (es) | 2012-12-17 |
| AR081638A1 (es) | 2012-10-10 |
| SMT201500272B (it) | 2016-01-08 |
| EA026140B1 (ru) | 2017-03-31 |
| CA2801491C (en) | 2018-01-23 |
| TW201201792A (en) | 2012-01-16 |
| EP2576586A1 (en) | 2013-04-10 |
| PT2576586E (pt) | 2015-10-23 |
| EA201270800A1 (ru) | 2013-04-30 |
| CA2801491A1 (en) | 2011-12-08 |
| BR112012030810A2 (pt) | 2019-09-24 |
| ES2548905T3 (es) | 2015-10-21 |
| JP2013527243A (ja) | 2013-06-27 |
| EP2576586B1 (en) | 2015-08-12 |
| SI2576586T1 (sl) | 2015-11-30 |
| US20120142653A1 (en) | 2012-06-07 |
| DK2576586T3 (en) | 2015-11-23 |
| HRP20150977T1 (hr) | 2015-10-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5755731B2 (ja) | Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体のｃ−２８アミド | |
| JP6000283B2 (ja) | Ｈｉｖ成熟阻害剤としてのｃ−３修飾ベツリン酸誘導体のｃ−２８アミン | |
| JP5752789B2 (ja) | Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体 | |
| JP6155285B2 (ja) | Ｈｉｖ成熟阻害活性のあるｃ−３シクロアルケニルトリテルペノイド | |
| JP6212545B2 (ja) | Ｈｉｖ成熟阻害活性を有するｃ−１７二環式アミンのトリテルペノイド | |
| JP6001560B2 (ja) | Ｈｉｖ成熟阻害活性を有するｃ−１７およびｃ−３修飾トリテルペノイド | |
| JP6186012B2 (ja) | Ｃ−３アルキルおよびアルケニル修飾ベツリン酸誘導体 | |
| AU2014215468B2 (en) | C-19 modified triterpenoids with HIV maturation inhibitory activity | |
| KR102411082B1 (ko) | 할로알킬 치환기를 지니는 비방향족 고리에 의해 위치 3에서 치환된，ｈｉｖ 성숙화 억제 활성을 갖는 트리테르페노이드 | |
| HK40041853A (en) | Triterpenoids with hiv maturation inhibitory activity | |
| JP2017533934A (ja) | Ｃ１７アリール置換ベツリン酸類似体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140527 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140527 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150414 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150423 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150519 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150527 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5755731 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |