KR101886467B1 - Hiv 성숙 억제 활성을 갖는 c-17 및 c-3 변형 트리테르페노이드 - Google Patents
Hiv 성숙 억제 활성을 갖는 c-17 및 c-3 변형 트리테르페노이드 Download PDFInfo
- Publication number
- KR101886467B1 KR101886467B1 KR1020137023070A KR20137023070A KR101886467B1 KR 101886467 B1 KR101886467 B1 KR 101886467B1 KR 1020137023070 A KR1020137023070 A KR 1020137023070A KR 20137023070 A KR20137023070 A KR 20137023070A KR 101886467 B1 KR101886467 B1 KR 101886467B1
- Authority
- KR
- South Korea
- Prior art keywords
- cyclopenta
- octadecahydro
- chrysene
- pentamethyl
- prop
- 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.)
- Active
Links
- 0 CC1CN(*)CCC1 Chemical compound CC1CN(*)CCC1 0.000 description 9
- RPYLNIGRILDSPE-CNJVCTELSA-N CC(C(N[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)N(CC1)CCS1(=O)=O Chemical compound CC(C(N[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)N(CC1)CCS1(=O)=O RPYLNIGRILDSPE-CNJVCTELSA-N 0.000 description 1
- MJBQUCZMSRYBSQ-PIHDDTHSSA-N CC(C)(C)N1CCN(CCN[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)CC1 Chemical compound CC(C)(C)N1CCN(CCN[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)CC1 MJBQUCZMSRYBSQ-PIHDDTHSSA-N 0.000 description 1
- ZOXVBQGVPIXQKX-KZIDLCPPSA-N CC(C)(C)OC(N1CC(CN[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)CCC1)=O Chemical compound CC(C)(C)OC(N1CC(CN[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)CCC1)=O ZOXVBQGVPIXQKX-KZIDLCPPSA-N 0.000 description 1
- XINAMINQGZVCRF-DHOUCCEOSA-N CC(C)(C)OC(N1CC(CN[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(OC)=O)=CC2)CCC1)=O Chemical compound CC(C)(C)OC(N1CC(CN[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(OC)=O)=CC2)CCC1)=O XINAMINQGZVCRF-DHOUCCEOSA-N 0.000 description 1
- MYKBUJHADMMUMQ-WVRTZRCQSA-N CC(C)(C)OC(N[C@@](CC[C@H]1C(C)=C)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@](C)(CC1)[C@@H]2C(C)(C)[C@H]1O)=O Chemical compound CC(C)(C)OC(N[C@@](CC[C@H]1C(C)=C)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@](C)(CC1)[C@@H]2C(C)(C)[C@H]1O)=O MYKBUJHADMMUMQ-WVRTZRCQSA-N 0.000 description 1
- AWWLEBXWLHWNOH-RVAHKPIVSA-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@@]21NC(C(c1ccc[s]1)N(CC1)CCS1(=O)=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@@]21NC(C(c1ccc[s]1)N(CC1)CCS1(=O)=O)=O AWWLEBXWLHWNOH-RVAHKPIVSA-N 0.000 description 1
- ASXPTHBDXDDNKW-JYXJZUCQSA-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@@]21NC(C(c1ccccc1)N(CC1)CCS1(=O)=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@@]21NC(C(c1ccccc1)N(CC1)CCS1(=O)=O)=O ASXPTHBDXDDNKW-JYXJZUCQSA-N 0.000 description 1
- ILKSBUNBKRINBT-QSIOBENTSA-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@@]21NC(CN(CC1)CCC1(F)F)=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@@]21NC(CN(CC1)CCC1(F)F)=O ILKSBUNBKRINBT-QSIOBENTSA-N 0.000 description 1
- PVLITSNKZLGYNL-QSIOBENTSA-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@@]21NC(CN(CC1)CCS1(=O)=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@@]21NC(CN(CC1)CCS1(=O)=O)=O PVLITSNKZLGYNL-QSIOBENTSA-N 0.000 description 1
- SELFDDRRABSMOC-LTKOBFLPSA-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@@]21NC(CN1CCN(CCO)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@@]21NC(CN1CCN(CCO)CC1)=O SELFDDRRABSMOC-LTKOBFLPSA-N 0.000 description 1
- JCNQVHWDBJAZRP-GWQUHLBTSA-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@@]21NC(C[n]1nncc1)=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@@]21NC(C[n]1nncc1)=O JCNQVHWDBJAZRP-GWQUHLBTSA-N 0.000 description 1
- KSEJHPFDAZFZNK-NFKLAVEJSA-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@@]21NC(Cc1cccnc1)=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@@]21NC(Cc1cccnc1)=O KSEJHPFDAZFZNK-NFKLAVEJSA-N 0.000 description 1
- ACZBXAHBIRGOAO-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@@]21NC(NCCCN(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@@]21NC(NCCCN(C)C)=O ACZBXAHBIRGOAO-WECSNRJHSA-N 0.000 description 1
- WDQCUEVVTGCAHY-CNJVCTELSA-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@@]21NCC(CCC1)CN1C(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@@]21NCC(CCC1)CN1C(O)=O WDQCUEVVTGCAHY-CNJVCTELSA-N 0.000 description 1
- VFQZQGDZAZZQAT-LCYMYPGXSA-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@@]21NCCC(F)(F)F 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@@]21NCCC(F)(F)F VFQZQGDZAZZQAT-LCYMYPGXSA-N 0.000 description 1
- NHXGXAYTPACMRC-PIHDDTHSSA-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@@]21NCCN(CC1)CCN1C(C1CC1)=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@@]21NCCN(CC1)CCN1C(C1CC1)=O NHXGXAYTPACMRC-PIHDDTHSSA-N 0.000 description 1
- IHTYYYOPVAXEDG-NMOVGBSOSA-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@@]21NCCNS(C1CC1)(=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@@]21NCCNS(C1CC1)(=O)=O IHTYYYOPVAXEDG-NMOVGBSOSA-N 0.000 description 1
- GYIAXBBOCOHMOJ-NFKLAVEJSA-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@@]21NCCNc1ccccn1 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@@]21NCCNc1ccccn1 GYIAXBBOCOHMOJ-NFKLAVEJSA-N 0.000 description 1
- XRKIAWVOKCLSOB-FJMUSEAASA-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@@]21NCCNc1cccnc1 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@@]21NCCNc1cccnc1 XRKIAWVOKCLSOB-FJMUSEAASA-N 0.000 description 1
- CYQWNFYDKCUCPR-RXSNDKFZSA-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@@]21Nc1nc(-c2ccc[s]2)c[s]1 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@@]21Nc1nc(-c2ccc[s]2)c[s]1 CYQWNFYDKCUCPR-RXSNDKFZSA-N 0.000 description 1
- YWAOPMYURACBJP-XCEJYUQWSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(OC)=O)=CC[C@]1(C)[C@@H](CC1)C2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)C21N Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(OC)=O)=CC[C@]1(C)[C@@H](CC1)C2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)C21N YWAOPMYURACBJP-XCEJYUQWSA-N 0.000 description 1
- YWAOPMYURACBJP-SLLAXXTQSA-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@@]21N 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@@]21N YWAOPMYURACBJP-SLLAXXTQSA-N 0.000 description 1
- UWERXWZDTULCPU-NFKLAVEJSA-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@@]21NC(CN(CC1)CCC1(F)F)=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@@]21NC(CN(CC1)CCC1(F)F)=O UWERXWZDTULCPU-NFKLAVEJSA-N 0.000 description 1
- ZIFMOWUGDAHYDQ-ZPJAASTHSA-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@@]21N 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@@]21N ZIFMOWUGDAHYDQ-ZPJAASTHSA-N 0.000 description 1
- ZHCATVSURSHVAG-UGCOLIGPSA-N CC(C)N1CCN(CC(N[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 Chemical compound CC(C)N1CCN(CC(N[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 ZHCATVSURSHVAG-UGCOLIGPSA-N 0.000 description 1
- NCZIQWVESNNUFH-UQZKPVNUSA-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(/C=C\C(\C(O)=O)=C/C)=C)[C@]13NCC(NC)=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(/C=C\C(\C(O)=O)=C/C)=C)[C@]13NCC(NC)=O NCZIQWVESNNUFH-UQZKPVNUSA-N 0.000 description 1
- CYKUHNITAWAWKC-BDPLOQFQSA-N CC1(CC1)C(N1CCN(CCN[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)CC1)O Chemical compound CC1(CC1)C(N1CCN(CCN[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)CC1)O CYKUHNITAWAWKC-BDPLOQFQSA-N 0.000 description 1
- ZXMCFDKIKJIYDX-XPGGRJDFSA-N CCc1c[s]c(N[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)ccc3/C(/OC)=[O]/CCC(CN([C@@](CC[C@H]3C(C)=C)(CC4)[C@H]3[C@@H](CC3)[C@]4(C)[C@](C)(CC4)[C@H]3[C@]3(C)[C@@H]4C(C)(C)C(c(cc4)ccc4C(OC)=O)=CC3)c3nc(CC)c[s]3)=O)=CC2)n1 Chemical compound CCc1c[s]c(N[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)ccc3/C(/OC)=[O]/CCC(CN([C@@](CC[C@H]3C(C)=C)(CC4)[C@H]3[C@@H](CC3)[C@]4(C)[C@](C)(CC4)[C@H]3[C@]3(C)[C@@H]4C(C)(C)C(c(cc4)ccc4C(OC)=O)=CC3)c3nc(CC)c[s]3)=O)=CC2)n1 ZXMCFDKIKJIYDX-XPGGRJDFSA-N 0.000 description 1
- XKWZLZLVNFUCBL-UHFFFAOYSA-N CS(C1CCNCC1)(=O)=O Chemical compound CS(C1CCNCC1)(=O)=O XKWZLZLVNFUCBL-UHFFFAOYSA-N 0.000 description 1
- ULIYQAUQKZDZOX-UHFFFAOYSA-N FC(CCI)(F)F Chemical compound FC(CCI)(F)F ULIYQAUQKZDZOX-UHFFFAOYSA-N 0.000 description 1
- MJOUJKDTBGXKIU-UHFFFAOYSA-N FC1(CCNCC1)F Chemical compound FC1(CCNCC1)F MJOUJKDTBGXKIU-UHFFFAOYSA-N 0.000 description 1
- QLHMLVWNDAKKON-UHFFFAOYSA-N [O-][N+](c(cccc1)c1S(NCCN(CC1)CCS1(=O)=O)(=O)=O)=O Chemical compound [O-][N+](c(cccc1)c1S(NCCN(CC1)CCS1(=O)=O)(=O)=O)=O QLHMLVWNDAKKON-UHFFFAOYSA-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
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161437893P | 2011-01-31 | 2011-01-31 | |
| US61/437,893 | 2011-01-31 | ||
| PCT/US2012/022852 WO2012106190A1 (en) | 2011-01-31 | 2012-01-27 | C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140016279A KR20140016279A (ko) | 2014-02-07 |
| KR101886467B1 true KR101886467B1 (ko) | 2018-08-07 |
Family
ID=45567147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137023070A Active KR101886467B1 (ko) | 2011-01-31 | 2012-01-27 | Hiv 성숙 억제 활성을 갖는 c-17 및 c-3 변형 트리테르페노이드 |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US8846647B2 (https=) |
| EP (1) | EP2670765B1 (https=) |
| JP (1) | JP6001560B2 (https=) |
| KR (1) | KR101886467B1 (https=) |
| CN (1) | CN103429607B (https=) |
| AR (1) | AR085053A1 (https=) |
| AU (1) | AU2012212509B2 (https=) |
| BR (1) | BR112013019419A2 (https=) |
| CA (1) | CA2826113C (https=) |
| CL (1) | CL2013002185A1 (https=) |
| CO (1) | CO6751275A2 (https=) |
| EA (1) | EA022470B1 (https=) |
| ES (1) | ES2653847T3 (https=) |
| IL (1) | IL227678B (https=) |
| MA (1) | MA34909B1 (https=) |
| MY (1) | MY162186A (https=) |
| PE (1) | PE20141152A1 (https=) |
| PH (1) | PH12013501528A1 (https=) |
| PT (1) | PT2670765T (https=) |
| SG (1) | SG192144A1 (https=) |
| TN (1) | TN2013000321A1 (https=) |
| TW (1) | TWI628188B (https=) |
| UY (1) | UY33886A (https=) |
| WO (1) | WO2012106190A1 (https=) |
| ZA (1) | ZA201306546B (https=) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5529851B2 (ja) | 2008-04-18 | 2014-06-25 | リアタ ファーマシューティカルズ インコーポレイテッド | 抗酸化炎症モジュレーター：ｃ−１７においてアミノ改変およびその他の改変を加えたオレアノール酸誘導体 |
| KR101713140B1 (ko) | 2008-04-18 | 2017-03-08 | 리타 파마슈티컬스 잉크. | Ｃ-환에서 포화된 산화방지성 염증 조절제 올레아놀산 유도체 |
| MX2010011439A (es) | 2008-04-18 | 2011-01-25 | Reata Pharmaceuticals Inc | Moduladores de inflamacion antioxidantes: derivados del acido oleanolico homologacion c-17. |
| WO2009146218A2 (en) | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| CN103596929B (zh) | 2010-12-17 | 2016-10-19 | 里亚塔医药公司 | 作为抗氧化发炎调节剂的吡唑及嘧啶三环烯酮 |
| HUE026371T2 (en) * | 2011-01-31 | 2016-05-30 | Bristol Myers Squibb Co | C-28 amines from modified C-3 betulinic acid derivatives as anti-HIV matrices |
| MX348862B (es) | 2011-03-11 | 2017-07-03 | Reata Pharmaceuticals Inc | Derivados c4-monometil triterpenoides y sus metodos de uso. |
| MX2014002936A (es) | 2011-09-21 | 2014-04-25 | Bristol Myers Squibb Co | Nuevos derivados de acido betulinico con actividad antiviral. |
| US8906889B2 (en) * | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| TWI623548B (zh) | 2012-04-27 | 2018-05-11 | 瑞塔醫藥有限責任公司 | 齊墩果酸（ｂａｒｄｏｘｏｌｏｎｅ ｍｅｔｈｙｌ）之２，２-二氟基丙醯胺衍生物、多晶型及其使用方法 |
| US8889854B2 (en) | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| WO2013188818A1 (en) | 2012-06-15 | 2013-12-19 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| BR112015003101B1 (pt) * | 2012-08-15 | 2022-06-14 | Glaxo Group Limited | Processo para a preparação de um composto |
| WO2014040073A1 (en) | 2012-09-10 | 2014-03-13 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| JP6243428B2 (ja) | 2012-09-10 | 2017-12-06 | リアタ ファーマシューティカルズ インコーポレイテッド | オレアノール酸のｃ１７−アルカンジイルおよびアルケンジイル誘導体ならびにその使用方法 |
| 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 |
| KR20150121712A (ko) * | 2013-02-25 | 2015-10-29 | 브리스톨-마이어스 스큅 컴퍼니 | Hiv의 치료에 유용한 c-3 알킬 및 알케닐 개질된 베툴린산 유도체 |
| UY36070A (es) | 2014-04-11 | 2015-10-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Triterpenoides con actividad inhibidora de la maduración de hiv |
| WO2015195776A1 (en) | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| US9969767B2 (en) | 2014-11-14 | 2018-05-15 | VIIV Healthcare UK (No.5) Limited | Oxolupene derivatives |
| CN107250152A (zh) * | 2014-11-14 | 2017-10-13 | Viiv保健英国第五有限公司 | C17‑芳基取代的桦木酸类似物 |
| EP3283467A1 (en) * | 2015-04-14 | 2018-02-21 | VIIV Healthcare UK(No.4) Limited | Methods of producing an hiv maturation inhibitor |
| US20180194799A1 (en) | 2015-07-28 | 2018-07-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017017609A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017025901A1 (en) * | 2015-08-11 | 2017-02-16 | Hetero Research Foundation | Novel c28-analogues with c3-modifications of triterpene derivatives as hiv inhibitors |
| JP7074674B2 (ja) | 2015-09-23 | 2022-05-24 | リアタ ファーマシューティカルズ インコーポレイテッド | Ｉｌ－１７の阻害及び他の使用のためのｃ４修飾オレアノール酸誘導体 |
| KR20180054826A (ko) | 2015-09-24 | 2018-05-24 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 성숙 억제 활성을 갖는 화합물 |
| EP3377177A2 (en) | 2015-11-20 | 2018-09-26 | VIIV Healthcare UK(No.4) Limited | Hiv maturation inhibitor formulations |
| 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 |
| EP3478703A1 (en) * | 2016-06-30 | 2019-05-08 | ViiV Healthcare UK (No.5) Limited | Triterpenoid inhibitors of human immunodeficiency virus replication |
| WO2018044822A1 (en) * | 2016-08-31 | 2018-03-08 | Viiv Healthcare Company | Combinations and uses and treatments thereof |
| MX2020001412A (es) | 2017-08-04 | 2020-08-03 | Ardelyx Inc | Compuestos y métodos para tratar la hiperpotasemia. |
| JP6926939B2 (ja) * | 2017-10-23 | 2021-08-25 | 東京エレクトロン株式会社 | 半導体装置の製造方法 |
| JP6977474B2 (ja) * | 2017-10-23 | 2021-12-08 | 東京エレクトロン株式会社 | 半導体装置の製造方法 |
| ES2970042T3 (es) | 2018-04-24 | 2024-05-24 | Viiv Healthcare Uk No 5 Ltd | Compuestos con actividad inhibidora de la maduración del VIH |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
| US12060340B2 (en) | 2018-06-20 | 2024-08-13 | Reata Pharmaceuticals, Inc | Cysteine-dependent inverse agonists of nuclear receptors ROR-gamma/ROR-gamma-t and methods of treating diseases or disorders therewith |
| PH12021551892A1 (en) | 2019-02-07 | 2022-08-01 | Ardelyx Inc | Glycyrrhetinic acid derivatives for use in treating hyperkalemia |
| AU2020222299C1 (en) | 2019-02-11 | 2024-05-16 | Hetero Labs Limited | Novel triterpene derivatives as HIV inhibitors |
| EP3999522B1 (en) | 2019-07-19 | 2025-09-03 | Reata Pharmaceuticals, Inc. | C17 polar-substituted heteroaromatic synthetic triterpenoids and methods of use thereof |
| GB2598300A (en) * | 2020-08-21 | 2022-03-02 | Univ Durham | Cross-linking method and applications in bioconjugation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009100532A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | NOVEL 17ß LUPANE DERIVATIVES |
Family Cites Families (17)
| 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 |
| US20020137755A1 (en) | 2000-12-04 | 2002-09-26 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| WO2004089357A2 (en) | 2003-04-02 | 2004-10-21 | Regents Of The University Of Minnesota | 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 |
| BRPI0508854A (pt) | 2004-03-17 | 2007-08-28 | Panacos Pharmaceuticals Inc | sais farmacêuticos de ácido-3-o-(3',3'-dimetilsuccinil) betulìnico |
| TW200628161A (en) * | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| US8067620B2 (en) | 2005-05-04 | 2011-11-29 | Medicines For Malaria Venture Mmv | Dispiro 1,2,4-trioxolane antimalarials |
| 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 |
| US9067966B2 (en) * | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| RS54239B1 (sr) * | 2010-06-04 | 2015-12-31 | Bristol-Myers Squibb Company | C-28 amidi modifikovanih derivata c-3 betulinske kiseline kao inhibitori sazrevanja hiv-a |
| US8754068B2 (en) * | 2010-06-04 | 2014-06-17 | Bristol-Myers Squibb Company | Modified C-3 betulinic acid derivatives as HIV maturation inhibitors |
-
2012
- 2012-01-27 US US13/359,727 patent/US8846647B2/en active Active
- 2012-01-27 WO PCT/US2012/022852 patent/WO2012106190A1/en not_active Ceased
- 2012-01-27 PT PT127029478T patent/PT2670765T/pt unknown
- 2012-01-27 JP JP2013551362A patent/JP6001560B2/ja active Active
- 2012-01-27 MY MYPI2013701325A patent/MY162186A/en unknown
- 2012-01-27 PH PH1/2013/501528A patent/PH12013501528A1/en unknown
- 2012-01-27 PE PE2013001719A patent/PE20141152A1/es active IP Right Grant
- 2012-01-27 ES ES12702947.8T patent/ES2653847T3/es active Active
- 2012-01-27 BR BR112013019419A patent/BR112013019419A2/pt not_active Application Discontinuation
- 2012-01-27 SG SG2013056858A patent/SG192144A1/en unknown
- 2012-01-27 CN CN201280014966.XA patent/CN103429607B/zh active Active
- 2012-01-27 AU AU2012212509A patent/AU2012212509B2/en active Active
- 2012-01-27 CA CA2826113A patent/CA2826113C/en active Active
- 2012-01-27 EP EP12702947.8A patent/EP2670765B1/en active Active
- 2012-01-27 KR KR1020137023070A patent/KR101886467B1/ko active Active
- 2012-01-27 MA MA36183A patent/MA34909B1/fr unknown
- 2012-01-27 EA EA201391127A patent/EA022470B1/ru not_active IP Right Cessation
- 2012-01-31 TW TW101103140A patent/TWI628188B/zh active
- 2012-01-31 UY UY0001033886A patent/UY33886A/es not_active Application Discontinuation
- 2012-01-31 AR ARP120100314A patent/AR085053A1/es unknown
-
2013
- 2013-07-26 TN TNP2013000321A patent/TN2013000321A1/fr unknown
- 2013-07-28 IL IL227678A patent/IL227678B/en active IP Right Grant
- 2013-07-30 CL CL2013002185A patent/CL2013002185A1/es unknown
- 2013-08-27 CO CO13203030A patent/CO6751275A2/es unknown
- 2013-08-30 ZA ZA2013/06546A patent/ZA201306546B/en unknown
-
2014
- 2014-07-24 US US14/339,572 patent/US20140343000A1/en not_active Abandoned
-
2016
- 2016-02-04 US US15/015,741 patent/US20160151387A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009100532A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | NOVEL 17ß LUPANE DERIVATIVES |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101886467B1 (ko) | Hiv 성숙 억제 활성을 갖는 c-17 및 c-3 변형 트리테르페노이드 | |
| KR20150013157A (ko) | Hiv 성숙 억제 활성을 갖는 트리테르페노이드의 c-17 비시클릭 아민 | |
| 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 | |
| KR20150115881A (ko) | Hiv 성숙 억제 활성을 갖는 c-19 변형된 트리테르페노이드 | |
| CA2826257A1 (en) | C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors | |
| EP2895471B1 (en) | Piperidine amide derivatives as hiv attachment inhibitors | |
| CA3013417C (en) | C-3 and c-17 modified triterpenoids as hiv-1 inhibitors | |
| CA2849475A1 (en) | Novel betulinic acid derivatives with antiviral activity | |
| CA2944778A1 (en) | Triterpenoids with hiv maturation inhibitory activity | |
| NZ614871B2 (en) | C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity | |
| HK40053429A (en) | C-3 and c-17 modified triterpenoids as hiv-1 inhibitors | |
| HK1256866B (en) | C-3 and c-17 modified triterpenoids as hiv-1 inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20130830 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20170112 Comment text: Request for Examination of Application |
|
| N231 | Notification of change of applicant | ||
| PN2301 | Change of applicant |
Patent event date: 20171220 Comment text: Notification of Change of Applicant Patent event code: PN23011R01D |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20180320 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20180726 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20180801 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20180801 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| FPAY | Annual fee payment |
Payment date: 20210723 Year of fee payment: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20210723 Start annual number: 4 End annual number: 4 |
|
| FPAY | Annual fee payment |
Payment date: 20220722 Year of fee payment: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20220722 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20230801 Start annual number: 6 End annual number: 6 |