JP2009533392A5 - - Google Patents
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- Publication number
- JP2009533392A5 JP2009533392A5 JP2009504741A JP2009504741A JP2009533392A5 JP 2009533392 A5 JP2009533392 A5 JP 2009533392A5 JP 2009504741 A JP2009504741 A JP 2009504741A JP 2009504741 A JP2009504741 A JP 2009504741A JP 2009533392 A5 JP2009533392 A5 JP 2009533392A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- methylandrostan
- methyleneandrostan
- enyl
- methylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 hydroxy, methoxy Chemical group 0.000 claims description 122
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000468 ketone group Chemical group 0.000 claims description 6
- 229930194542 Keto Natural products 0.000 claims description 5
- ZMDJOPZTDZPBCS-XXZKLPIOSA-N (5s,6s,8r,9s,10r,13s,14s)-3-(2-aminoethoxyimino)-5-hydroxy-6,10,13-trimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@]12C)CC(=NOCCN)C[C@]1(O)[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@H]21 ZMDJOPZTDZPBCS-XXZKLPIOSA-N 0.000 claims description 3
- MNJDAFFYIMEQGR-LZXLFTNQSA-N (5s,6s,8r,9s,10r,13s,14s)-3-(3-aminopropoxyimino)-5-hydroxy-6,10,13-trimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@]12C)CC(=NOCCCN)C[C@]1(O)[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@H]21 MNJDAFFYIMEQGR-LZXLFTNQSA-N 0.000 claims description 3
- IZCKKFUGQBEJCL-LZXLFTNQSA-N (5s,6s,8r,9s,10r,13s,14s)-5-hydroxy-6,10,13-trimethyl-3-[2-(methylamino)ethoxyimino]-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1C[C@H](C)[C@]1(O)[C@]2(C)CCC(=NOCCNC)C1 IZCKKFUGQBEJCL-LZXLFTNQSA-N 0.000 claims description 3
- QPADLKFPLWEPNY-PCWRDYCRSA-N (5s,6s,8r,9s,10r,13s,14s)-5-hydroxy-6,10,13-trimethyl-3-[3-(methylamino)propoxyimino]-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1C[C@H](C)[C@]1(O)[C@]2(C)CCC(=NOCCCNC)C1 QPADLKFPLWEPNY-PCWRDYCRSA-N 0.000 claims description 3
- PPZWNYRHUCKSDQ-VCJHBGCNSA-N (5R,8R,9S,10R,13S,14S)-10,13-dimethyl-3-[2-(methylamino)ethoxyimino]-6-methylidene-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound CNCCON=C1C[C@@H]2C(C[C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)=O)C)[C@]2(CC1)C)=C PPZWNYRHUCKSDQ-VCJHBGCNSA-N 0.000 claims description 2
- RWGFAACMTZTSMH-LHQSUDNYSA-N (5R,8R,9S,10R,13S,14S)-10,13-dimethyl-3-[3-(methylamino)propoxyimino]-6-methylidene-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound CNCCCON=C1C[C@@H]2C(C[C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)=O)C)[C@]2(CC1)C)=C RWGFAACMTZTSMH-LHQSUDNYSA-N 0.000 claims description 2
- JECNZFUADDFHDL-FNSJINJNSA-N (5R,8R,9S,10R,13S,14S)-3-(2-aminoethoxyimino)-10,13-dimethyl-6-methylidene-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound NCCON=C1C[C@@H]2C(C[C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)=O)C)[C@]2(CC1)C)=C JECNZFUADDFHDL-FNSJINJNSA-N 0.000 claims description 2
- KLRXSGDIIZNUFW-VCJHBGCNSA-N (5R,8R,9S,10R,13S,14S)-3-(3-aminopropoxyimino)-10,13-dimethyl-6-methylidene-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound NCCCON=C1C[C@@H]2C(C[C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)=O)C)[C@]2(CC1)C)=C KLRXSGDIIZNUFW-VCJHBGCNSA-N 0.000 claims description 2
- KXXQWDNLSDTIID-YZKULWDZSA-N (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-3-[2-(methylamino)ethoxyimino]-7-methylidene-1,2,4,5,6,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound CNCCON=C1C[C@@H]2CC([C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)=O)C)[C@]2(CC1)C)=C KXXQWDNLSDTIID-YZKULWDZSA-N 0.000 claims description 2
- CVUAYAMZHNGCTH-LQUXNCDFSA-N (5S,8R,9S,10S,13S,14S)-3-(2-aminoethoxyimino)-10,13-dimethyl-7-methylidene-1,2,4,5,6,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound NCCON=C1C[C@@H]2CC([C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)=O)C)[C@]2(CC1)C)=C CVUAYAMZHNGCTH-LQUXNCDFSA-N 0.000 claims description 2
- SVHDCRLIMUWBMF-YZKULWDZSA-N (5S,8R,9S,10S,13S,14S)-3-(3-aminopropoxyimino)-10,13-dimethyl-7-methylidene-1,2,4,5,6,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound NCCCON=C1C[C@@H]2CC([C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)=O)C)[C@]2(CC1)C)=C SVHDCRLIMUWBMF-YZKULWDZSA-N 0.000 claims description 2
- MRJWKEBFNLYXCC-QMFQMFHYSA-N (5r,7r,8r,9s,10r,13s,14s)-3-(2-aminoethoxyimino)-5-hydroxy-7,10,13-trimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1[C@H](C)C[C@]1(O)[C@]2(C)CCC(=NOCCN)C1 MRJWKEBFNLYXCC-QMFQMFHYSA-N 0.000 claims description 2
- NJSFDLXETOYWJG-LBRFZRMISA-N (5r,7r,8r,9s,10r,13s,14s)-3-(3-aminopropoxyimino)-5-hydroxy-7,10,13-trimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1[C@H](C)C[C@]1(O)[C@]2(C)CCC(=NOCCCN)C1 NJSFDLXETOYWJG-LBRFZRMISA-N 0.000 claims description 2
- IJCYMAMLVBSHCF-LBRFZRMISA-N (5r,7r,8r,9s,10r,13s,14s)-5-hydroxy-7,10,13-trimethyl-3-[2-(methylamino)ethoxyimino]-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1[C@H](C)C[C@]1(O)[C@]2(C)CCC(=NOCCNC)C1 IJCYMAMLVBSHCF-LBRFZRMISA-N 0.000 claims description 2
- GLHFUAGUGIBDFY-MVCQNYRTSA-N (5r,8r,9s,10r,13s,14s)-3-(2-aminoethoxyimino)-5-hydroxy-10,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C(=NOCCN)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@]21O GLHFUAGUGIBDFY-MVCQNYRTSA-N 0.000 claims description 2
- NSMBUWUAJOJVNK-XZQQMQJFSA-N (5r,8r,9s,10r,13s,14s)-3-(2-aminoethoxyimino)-5-hydroxy-10,13-dimethyl-7-methylidene-2,4,6,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C(=NOCCN)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C(=C)C[C@]21O NSMBUWUAJOJVNK-XZQQMQJFSA-N 0.000 claims description 2
- IIZPLRIDFUZHNC-HLMGQEERSA-N (5r,8r,9s,10r,13s,14s)-3-(3-aminopropoxyimino)-5-hydroxy-10,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C(=NOCCCN)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@]21O IIZPLRIDFUZHNC-HLMGQEERSA-N 0.000 claims description 2
- JFMZMWDAIYEPDD-FCZDUJBQSA-N (5r,8r,9s,10r,13s,14s)-3-(3-aminopropoxyimino)-5-hydroxy-10,13-dimethyl-7-methylidene-2,4,6,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C(=NOCCCN)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C(=C)C[C@]21O JFMZMWDAIYEPDD-FCZDUJBQSA-N 0.000 claims description 2
- OHYXHLBJEIZZCG-HLMGQEERSA-N (5r,8r,9s,10r,13s,14s)-5-hydroxy-10,13-dimethyl-3-[2-(methylamino)ethoxyimino]-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC[C@]1(O)[C@]2(C)CCC(=NOCCNC)C1 OHYXHLBJEIZZCG-HLMGQEERSA-N 0.000 claims description 2
- WIMLFPYUGKQJDZ-FCZDUJBQSA-N (5r,8r,9s,10r,13s,14s)-5-hydroxy-10,13-dimethyl-3-[2-(methylamino)ethoxyimino]-7-methylidene-2,4,6,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1C(=C)C[C@]1(O)[C@]2(C)CCC(=NOCCNC)C1 WIMLFPYUGKQJDZ-FCZDUJBQSA-N 0.000 claims description 2
- NDCITPBESYWIMN-ROSOUBNMSA-N (5r,8r,9s,10r,13s,14s)-5-hydroxy-10,13-dimethyl-3-[3-(methylamino)propoxyimino]-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC[C@]1(O)[C@]2(C)CCC(=NOCCCNC)C1 NDCITPBESYWIMN-ROSOUBNMSA-N 0.000 claims description 2
- WEDKMKPZOAFEQB-BNWJRGKBSA-N (5r,8r,9s,10r,13s,14s)-5-hydroxy-10,13-dimethyl-3-[3-(methylamino)propoxyimino]-7-methylidene-2,4,6,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1C(=C)C[C@]1(O)[C@]2(C)CCC(=NOCCCNC)C1 WEDKMKPZOAFEQB-BNWJRGKBSA-N 0.000 claims description 2
- ISNZJCJQIXOROZ-RLZRBERESA-N (5s,8r,9s,10r,13s,14s)-3-(2-aminoethoxyimino)-5-hydroxy-10,13-dimethyl-6-methylidene-2,4,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C(=NOCCN)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)[C@]21O ISNZJCJQIXOROZ-RLZRBERESA-N 0.000 claims description 2
- HFSUMZGFDAKXIJ-BIHGRHEHSA-N (5s,8r,9s,10r,13s,14s)-3-(3-aminopropoxyimino)-5-hydroxy-10,13-dimethyl-6-methylidene-2,4,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C(=NOCCCN)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)[C@]21O HFSUMZGFDAKXIJ-BIHGRHEHSA-N 0.000 claims description 2
- WDCFIUBLEDMUBT-BIHGRHEHSA-N (5s,8r,9s,10r,13s,14s)-5-hydroxy-10,13-dimethyl-3-[2-(methylamino)ethoxyimino]-6-methylidene-2,4,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC(=C)[C@]1(O)[C@]2(C)CCC(=NOCCNC)C1 WDCFIUBLEDMUBT-BIHGRHEHSA-N 0.000 claims description 2
- RHJAQECPTTWIHF-PFGPNTLWSA-N (5s,8r,9s,10r,13s,14s)-5-hydroxy-10,13-dimethyl-3-[3-(methylamino)propoxyimino]-6-methylidene-2,4,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC(=C)[C@]1(O)[C@]2(C)CCC(=NOCCCNC)C1 RHJAQECPTTWIHF-PFGPNTLWSA-N 0.000 claims description 2
- GPYIOUIOOLOMBI-JRFAEIQQSA-N (6s,8r,9s,10s,13s,14s)-3-(2-aminoethoxyimino)-6,10,13-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@]12C)CC(=NOCCN)CC1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@H]21 GPYIOUIOOLOMBI-JRFAEIQQSA-N 0.000 claims description 2
- FDKAFVIVSZKGQQ-FLPCDVSNSA-N (6s,8r,9s,10s,13s,14s)-3-(3-aminopropoxyimino)-6,10,13-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@]12C)CC(=NOCCCN)CC1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@H]21 FDKAFVIVSZKGQQ-FLPCDVSNSA-N 0.000 claims description 2
- NMHWWKMETYYWSP-FLPCDVSNSA-N (6s,8r,9s,10s,13s,14s)-6,10,13-trimethyl-3-[2-(methylamino)ethoxyimino]-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1C[C@H](C)C1[C@]2(C)CCC(=NOCCNC)C1 NMHWWKMETYYWSP-FLPCDVSNSA-N 0.000 claims description 2
- OAFZCBUDZIATEM-JLNKZOJSSA-N (6s,8r,9s,10s,13s,14s)-6,10,13-trimethyl-3-[3-(methylamino)propoxyimino]-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1C[C@H](C)C1[C@]2(C)CCC(=NOCCCNC)C1 OAFZCBUDZIATEM-JLNKZOJSSA-N 0.000 claims description 2
- MFRODIFWILXSAP-YGVNNQDLSA-N (7r,8r,9s,10s,13s,14s)-3-(2-aminoethoxyimino)-7,10,13-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1[C@H](C)CC1[C@]2(C)CCC(=NOCCN)C1 MFRODIFWILXSAP-YGVNNQDLSA-N 0.000 claims description 2
- WZMLNVFIMCHEMB-ALUDSUMFSA-N (7r,8r,9s,10s,13s,14s)-3-(3-aminopropoxyimino)-7,10,13-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC[C@H]3[C@@H]1[C@H](C)CC1[C@]2(C)CCC(=NOCCCN)C1 WZMLNVFIMCHEMB-ALUDSUMFSA-N 0.000 claims description 2
- LOKKXHYPMAGVFS-ALUDSUMFSA-N (7r,8r,9s,10s,13s,14s)-7,10,13-trimethyl-3-[2-(methylamino)ethoxyimino]-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2[C@@]3(C)CCC(=NOCCNC)CC3C[C@@H](C)[C@H]2[C@@H]2CCC(=O)[C@]21C LOKKXHYPMAGVFS-ALUDSUMFSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 7
- QZLYKIGBANMMBK-UGCZWRCOSA-N androstane group Chemical group [C@@H]12CCC[C@@]1(C)CC[C@H]1[C@H]2CC[C@H]2CCCC[C@]12C QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 230000002503 metabolic effect Effects 0.000 claims 6
- 239000002207 metabolite Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 230000003287 optical effect Effects 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 239000002243 precursor Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- AUNVBIZZXOXJJM-YMMDYLBISA-N (5s,6s,8r,9s,10r,13s,14s)-3-(2-aminocyclopentyl)oxyimino-5-hydroxy-6,10,13-trimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C([C@]1(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@@H]2C[C@@H]([C@]1(C1)O)C)CC1=NOC1CCCC1N AUNVBIZZXOXJJM-YMMDYLBISA-N 0.000 claims 2
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 claims 2
- 208000010061 Autosomal Dominant Polycystic Kidney Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- 244000166550 Strophanthus gratus Species 0.000 claims 2
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- NOGFKPDHLJKVMN-DUJLXMMVSA-N (7R,8R,9S,10S,13R,14S)-3-(2-aminopropoxyimino)-7,10,13-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one Chemical compound NC(CON=C1CC2C[C@H]([C@H]3[C@@H]4CCC([C@]4(C)CC[C@@H]3[C@]2(CC1)C)=O)C)C NOGFKPDHLJKVMN-DUJLXMMVSA-N 0.000 description 1
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- USEVKSGANQDRKI-UPPAANNFSA-N (7r,8r,9s,10s,13s,14s)-7,10,13-trimethyl-3-[3-(methylamino)propoxyimino]-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2[C@@]3(C)CCC(=NOCCCNC)CC3C[C@@H](C)[C@H]2[C@@H]2CCC(=O)[C@]21C USEVKSGANQDRKI-UPPAANNFSA-N 0.000 description 1
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| PCT/EP2007/053524 WO2007118832A2 (en) | 2006-04-13 | 2007-04-11 | Amino derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
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| US8168621B2 (en) | 2005-09-30 | 2012-05-01 | Endece, Llc | 6-substituted estradiol derivatives and methods of use |
| US10174070B2 (en) | 2005-09-30 | 2019-01-08 | Endece Llc | 6-substituted estradiol derivatives and methods of use |
| JP5290189B2 (ja) * | 2006-11-30 | 2013-09-18 | エンディース エルエルシー | ６−アルコキシアルキルエストラジオール誘導体およびその使用 |
| JP5738267B2 (ja) * | 2009-03-23 | 2015-06-24 | シグマ−タウ・インドゥストリエ・ファルマチェウチケ・リウニテ・ソシエタ・ペル・アチオニＳｉｇｍａ−Ｔａｕ Ｉｎｄｕｓｔｒｉｅ Ｆａｒｍａｃｅｕｔｉｃｈｅ Ｒｉｕｎｉｔｅ Ｓｏｃｉｅｔａ Ｐｅｒ Ａｚｉｏｎｉ | タンパク尿、糸球体硬化、及び腎不全の治療に有用な５−β，１４−β−アンドロスタン誘導体 |
| WO2010149666A1 (en) | 2009-06-22 | 2010-12-29 | Medexis S.A. | Methods for treating neoplasia |
| WO2017149052A1 (en) * | 2016-03-02 | 2017-09-08 | Patheon Austria Gmbh Co. & Kg | Process and intermediates for the production of 17(20)-ene b-seco steroids |
| EP3962921B1 (en) * | 2019-04-27 | 2025-11-05 | Health Research, Inc. | Coumarin-modified androgens for the treatment of prostate cancer |
| FI3805243T3 (fi) * | 2019-10-09 | 2024-02-07 | Windtree Therapeutics Inc | Androstaanijohdannaisia, joilla on aktiivisuus puhtaina tai pääasiallisesti puhtaina SERCA2a:n stimulaattoreina, sydämen vajaatoiminnan hoitoon |
| CN111040012B (zh) * | 2019-12-27 | 2022-04-15 | 山东安弘制药有限公司 | 一种依西美坦螺环氧乙烷杂质的制备方法 |
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| GB868303A (en) | 1956-09-08 | 1961-05-17 | Syntex Sa | New cyclopentanophenanthrene derivatives and process for the production thereof |
| BE589491A (enExample) * | 1959-04-10 | |||
| US3210386A (en) | 1961-01-09 | 1965-10-05 | Upjohn Co | 3-aminoethers of 3beta-hydroxy androstanes |
| DE1187236B (de) | 1961-03-28 | 1965-02-18 | Searle & Co | Verfahren zur Herstellung von 17beta-Aminosteroiden |
| GB1042292A (en) * | 1961-11-08 | 1966-09-14 | Organon Labor Ltd | 5ª‡-hydroxy-6ª‰-amino steroids and the preparation thereof |
| US3120515A (en) | 1962-05-31 | 1964-02-04 | Sterling Drug Inc | 5-cyano steroids, their preparation, and derivatives thereof |
| US5144017A (en) * | 1988-07-13 | 1992-09-01 | University Of Manitoba | Compounds that bind to digitalis receptor |
| US5522847A (en) * | 1993-06-18 | 1996-06-04 | Kalis; Amy G. | Pacifier with novelty electronic display |
| US5662685A (en) * | 1996-08-13 | 1997-09-02 | Uhler; Gary S. | Sound producing pacifier |
| DE19633349A1 (de) * | 1996-08-19 | 1998-02-26 | Sigma Tau Ind Farmaceuti | Neue 6-Hydroxy- und 6-Oxo-androstan-Derivate, die auf das kardiovaskuläre System wirken und pharmazeutische Zusammensetzungen, die diese enthalten |
| US6066161A (en) * | 1997-07-26 | 2000-05-23 | Parella; Nicole D. X. | Baby pacifier apparatus with remote control locator |
| DE19906159A1 (de) * | 1999-02-09 | 2000-08-10 | Schering Ag | 16-Hydroxyestratriene als selektiv wirksame Estrogene |
| DK1689410T3 (da) * | 2003-11-26 | 2008-09-08 | Bayer Schering Pharma Ag | Forebyggelse og behandling af hypertensive hjertesygdomme ved de selektive östrogener 8beta-vinyl-estra-1,3,5(10)-trien-3,17beta-diol og 17beta-fluor-9alpha-vinyl-estra-1,3,5(10)-trien-3,16alpha-diol |
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- 2007-04-11 JP JP2009504741A patent/JP5438503B2/ja not_active Expired - Fee Related
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- 2007-04-11 PT PT77279925T patent/PT2004668E/pt unknown
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- 2007-04-11 PL PL07727992T patent/PL2004668T3/pl unknown
- 2007-04-11 MX MX2008012942A patent/MX2008012942A/es active IP Right Grant
- 2007-04-11 AR ARP070101523A patent/AR060427A1/es not_active Application Discontinuation
- 2007-04-11 EA EA200870434A patent/EA015257B1/ru not_active IP Right Cessation
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