AU2014290512A1 - Methods, systems, and compositions for promoting bone growth - Google Patents
Methods, systems, and compositions for promoting bone growth Download PDFInfo
- Publication number
- AU2014290512A1 AU2014290512A1 AU2014290512A AU2014290512A AU2014290512A1 AU 2014290512 A1 AU2014290512 A1 AU 2014290512A1 AU 2014290512 A AU2014290512 A AU 2014290512A AU 2014290512 A AU2014290512 A AU 2014290512A AU 2014290512 A1 AU2014290512 A1 AU 2014290512A1
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- AU
- Australia
- Prior art keywords
- oxopyrrolidin
- hydroxy
- methyl
- difluoro
- thiophene
- 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.)
- Abandoned
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- 238000000034 method Methods 0.000 title claims description 92
- 230000008468 bone growth Effects 0.000 title description 9
- 230000001737 promoting effect Effects 0.000 title description 7
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims abstract description 56
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 113
- -1 C 1 C 3 alkoxy Chemical group 0.000 claims description 109
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
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- NDBMETWZNQYRFP-YOIRJEGESA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s)-3-hydroxydec-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CCCC#CCC[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 NDBMETWZNQYRFP-YOIRJEGESA-N 0.000 claims description 3
- ZSNYVRWVRBCGAF-IGXNXKSNSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s)-3-hydroxynon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CCC#CCC[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 ZSNYVRWVRBCGAF-IGXNXKSNSA-N 0.000 claims description 3
- ARNNZUVXJVDGJW-JJGIJDNGSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s)-3-hydroxyoct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CC#CCC[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 ARNNZUVXJVDGJW-JJGIJDNGSA-N 0.000 claims description 3
- QCQZBSOBEKMLKJ-JJGIJDNGSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s)-3-hydroxyoct-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CCCCC[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 QCQZBSOBEKMLKJ-JJGIJDNGSA-N 0.000 claims description 3
- UMYXRXWDPHAKGZ-YWDXQQJVSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4r)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CCC#CC[C@@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 UMYXRXWDPHAKGZ-YWDXQQJVSA-N 0.000 claims description 3
- XLCABUXIRDDWSG-GJWBGHMGSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-7-phenylhept-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)C#CC1=CC=CC=C1 XLCABUXIRDDWSG-GJWBGHMGSA-N 0.000 claims description 3
- PBEADSCFVAUBQH-OFQUAYIFSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyldec-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CCCC#CC[C@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 PBEADSCFVAUBQH-OFQUAYIFSA-N 0.000 claims description 3
- UMYXRXWDPHAKGZ-XLJJWPCRSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CCC#CC[C@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 UMYXRXWDPHAKGZ-XLJJWPCRSA-N 0.000 claims description 3
- KYVPVSMNVVVAAD-OTSVUREYSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CC#CC[C@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 KYVPVSMNVVVAAD-OTSVUREYSA-N 0.000 claims description 3
- SXKFGUFPKNABIY-OTSVUREYSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyloct-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound CCCC[C@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 SXKFGUFPKNABIY-OTSVUREYSA-N 0.000 claims description 3
- WHBBPUSLNFAUJV-HXIYYJMWSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-phenylpent-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@@H]1/C=C/[C@H](O)[C@@H](C)C=2C=CC=CC=2)C(F)(F)C(=O)N1CCCC1=CC=C(C(O)=O)S1 WHBBPUSLNFAUJV-HXIYYJMWSA-N 0.000 claims description 3
- GWWAGJDSDSCGLK-RCZSKKKRSA-N 5-[3-[(5s)-3,3-difluoro-5-[(3r,4s)-3-hydroxy-4-methyl-7-phenylheptyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@H](O)CC[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CCC1=CC=CC=C1 GWWAGJDSDSCGLK-RCZSKKKRSA-N 0.000 claims description 3
- DEQPIOBZNPCKJE-GLDDHKADSA-N 7-[(2R)-2-[(E,3S)-3-hydroxy-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C(/[C@@H](O)CCCCc1ccccc1)=C\[C@@H]1N(CCCCCCC(O)=O)C(=O)CC1 DEQPIOBZNPCKJE-GLDDHKADSA-N 0.000 claims description 3
- DBZBLAFPTDAAPH-VMNGNHSPSA-N 7-[(2r)-2-[(e,3r)-3-hydroxyhept-1-en-4-ynyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CCC#C[C@H](O)\C=C\[C@H]1CCC(=O)N1CCCCCCC(O)=O DBZBLAFPTDAAPH-VMNGNHSPSA-N 0.000 claims description 3
- XLBCQUAHSNWMTQ-FNUDCVAISA-N 7-[(2r)-2-[(e,3s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CC#CCC(C)[C@H](O)\C=C\[C@H]1CCC(=O)N1CCCCCCC(O)=O XLBCQUAHSNWMTQ-FNUDCVAISA-N 0.000 claims description 3
- DBZBLAFPTDAAPH-AOOXPWSASA-N 7-[(2r)-2-[(e,3s)-3-hydroxyhept-1-en-4-ynyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CCC#C[C@@H](O)\C=C\[C@H]1CCC(=O)N1CCCCCCC(O)=O DBZBLAFPTDAAPH-AOOXPWSASA-N 0.000 claims description 3
- CHLXVWPOHSBADP-GUPMMHBCSA-N 7-[(2r)-2-[(e,3s,4r)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C([C@@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)CC1)CCCCCCC(O)=O)CCC1=CC=CC=C1 CHLXVWPOHSBADP-GUPMMHBCSA-N 0.000 claims description 3
- CHLXVWPOHSBADP-FXDNMFHBSA-N 7-[(2r)-2-[(e,3s,4s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)CC1)CCCCCCC(O)=O)CCC1=CC=CC=C1 CHLXVWPOHSBADP-FXDNMFHBSA-N 0.000 claims description 3
- UJPIOOJJAAMYNA-HSFNZESZSA-N 7-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CC([C@@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCCCCC(O)=O)CCCC1=CC=CC=C1 UJPIOOJJAAMYNA-HSFNZESZSA-N 0.000 claims description 3
- KWEXZQZQGLFDSE-OAEJALACSA-N 7-[(5r)-3,3-difluoro-5-[(e,3r,4r)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CC#CC[C@@H](C)[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(O)=O KWEXZQZQGLFDSE-OAEJALACSA-N 0.000 claims description 3
- ZSUOOBFOIDLLEI-LPJXYHDHSA-N 7-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CCC#CC[C@H](C)[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(O)=O ZSUOOBFOIDLLEI-LPJXYHDHSA-N 0.000 claims description 3
- KWEXZQZQGLFDSE-ZCKSSPOOSA-N 7-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CC#CC[C@H](C)[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(O)=O KWEXZQZQGLFDSE-ZCKSSPOOSA-N 0.000 claims description 3
- UJPIOOJJAAMYNA-YNLQGXKESA-N 7-[(5r)-3,3-difluoro-5-[(e,3s,4r)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C([C@@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCCCCC(O)=O)CCC1=CC=CC=C1 UJPIOOJJAAMYNA-YNLQGXKESA-N 0.000 claims description 3
- KWEXZQZQGLFDSE-PHAHAWKESA-N 7-[(5r)-3,3-difluoro-5-[(e,3s,4r)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CC#CC[C@@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(O)=O KWEXZQZQGLFDSE-PHAHAWKESA-N 0.000 claims description 3
- UJPIOOJJAAMYNA-ZFBSANRWSA-N 7-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCCCCC(O)=O)CCC1=CC=CC=C1 UJPIOOJJAAMYNA-ZFBSANRWSA-N 0.000 claims description 3
- KWEXZQZQGLFDSE-PMCDXHSFSA-N 7-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CC#CC[C@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(O)=O KWEXZQZQGLFDSE-PMCDXHSFSA-N 0.000 claims description 3
- 235000019739 Dicalciumphosphate Nutrition 0.000 claims description 3
- CRUNFNWPSSJCFB-QLHPQISQSA-N O[C@@H](/C=C/[C@@H]1N(C(CC1)=O)CCCC1=CC=C(S1)C(=O)O)[C@@H](CCCCCC1=CC=CC=C1)C Chemical compound O[C@@H](/C=C/[C@@H]1N(C(CC1)=O)CCCC1=CC=C(S1)C(=O)O)[C@@H](CCCCCC1=CC=CC=C1)C CRUNFNWPSSJCFB-QLHPQISQSA-N 0.000 claims description 3
- ZXECFDRPIPRVFB-CRODIQNZSA-N O[C@H](/C=C/[C@@H]1N(C(CC1)=O)CCCC1=CC=C(S1)C(=O)O)[C@@H](CCC1=CC=CC=C1)C Chemical compound O[C@H](/C=C/[C@@H]1N(C(CC1)=O)CCCC1=CC=C(S1)C(=O)O)[C@@H](CCC1=CC=CC=C1)C ZXECFDRPIPRVFB-CRODIQNZSA-N 0.000 claims description 3
- 229910000390 dicalcium phosphate Inorganic materials 0.000 claims description 3
- 229940038472 dicalcium phosphate Drugs 0.000 claims description 3
- DAJAZGMSWQEQIQ-BPZODPGYSA-N ethyl 4-[2-[(2R)-2-[(E,3S,4S)-3-hydroxy-4-methylnon-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]ethyl]benzoate Chemical compound c1cc(C(=O)OCC)ccc1CCN1[C@@H](\C=C\[C@@H](O)[C@@H](C)CC#CCC)CCC1=O DAJAZGMSWQEQIQ-BPZODPGYSA-N 0.000 claims description 3
- DAJAZGMSWQEQIQ-LRCPYKSLSA-N ethyl 4-[2-[(2r)-2-[(e,3r,4s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]ethyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1CCN1C(=O)CC[C@@H]1\C=C\[C@H](O)[C@@H](C)CC#CCC DAJAZGMSWQEQIQ-LRCPYKSLSA-N 0.000 claims description 3
- DPIIPICOSBDYFN-JMQOMVKFSA-N methyl 4-[2-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]ethyl]benzoate Chemical compound CCC#CCC(C)[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCC1=CC=C(C(=O)OC)C=C1 DPIIPICOSBDYFN-JMQOMVKFSA-N 0.000 claims description 3
- WOUCGIVTGQFWSE-FUTHQCHMSA-N methyl 4-[2-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxyoct-1-enyl]-2-oxopyrrolidin-1-yl]ethyl]benzoate Chemical compound CCCCC[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCC1=CC=C(C(=O)OC)C=C1 WOUCGIVTGQFWSE-FUTHQCHMSA-N 0.000 claims description 3
- WOUCGIVTGQFWSE-JUFISIKESA-N methyl 4-[2-[(5r)-3,3-difluoro-5-[(e,3s)-3-hydroxyoct-1-enyl]-2-oxopyrrolidin-1-yl]ethyl]benzoate Chemical compound CCCCC[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCC1=CC=C(C(=O)OC)C=C1 WOUCGIVTGQFWSE-JUFISIKESA-N 0.000 claims description 3
- DPIIPICOSBDYFN-MPRFVXRBSA-N methyl 4-[2-[(5r)-3,3-difluoro-5-[(e,3s,4r)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]ethyl]benzoate Chemical compound CCC#CC[C@@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCC1=CC=C(C(=O)OC)C=C1 DPIIPICOSBDYFN-MPRFVXRBSA-N 0.000 claims description 3
- DPIIPICOSBDYFN-DIINUUSZSA-N methyl 4-[2-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]ethyl]benzoate Chemical compound CCC#CC[C@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCC1=CC=C(C(=O)OC)C=C1 DPIIPICOSBDYFN-DIINUUSZSA-N 0.000 claims description 3
- JUSJTDLHSOSXJS-CMGJWZOBSA-N methyl 5-[3-[(2r)-2-[(e,3r)-3-hydroxy-4-methyl-7-phenylhept-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]prop-1-ynyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C#CCN1C(=O)CC[C@@H]1\C=C\[C@H](O)C(C)CC#CC1=CC=CC=C1 JUSJTDLHSOSXJS-CMGJWZOBSA-N 0.000 claims description 3
- MPQNGSFETCOJTQ-CMGJWZOBSA-N methyl 5-[3-[(2r)-2-[(e,3r)-3-hydroxy-4-methyl-7-phenylhept-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)CC[C@@H]1\C=C\[C@H](O)C(C)CC#CC1=CC=CC=C1 MPQNGSFETCOJTQ-CMGJWZOBSA-N 0.000 claims description 3
- ROBDZQUCFGAGKN-CMGJWZOBSA-N methyl 5-[3-[(2r)-2-[(e,3r)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]prop-1-ynyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C#CCN1C(=O)CC[C@@H]1\C=C\[C@H](O)C(C)CCCC1=CC=CC=C1 ROBDZQUCFGAGKN-CMGJWZOBSA-N 0.000 claims description 3
- LWTJYNJWUFYPPE-CMGJWZOBSA-N methyl 5-[3-[(2r)-2-[(e,3r)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)CC[C@@H]1\C=C\[C@H](O)C(C)CCCC1=CC=CC=C1 LWTJYNJWUFYPPE-CMGJWZOBSA-N 0.000 claims description 3
- VMFROVKJYQMOJO-TYXBMBSUSA-N methyl 5-[3-[(2r)-2-[(e,3r)-3-hydroxy-4-methylnon-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]prop-1-ynyl]thiophene-2-carboxylate Chemical compound CCC#CCC(C)[C@@H](O)\C=C\[C@H]1CCC(=O)N1CC#CC1=CC=C(C(=O)OC)S1 VMFROVKJYQMOJO-TYXBMBSUSA-N 0.000 claims description 3
- AVZCAQNCYODQHK-TYXBMBSUSA-N methyl 5-[3-[(2r)-2-[(e,3r)-3-hydroxy-4-methylnon-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound CCC#CCC(C)[C@@H](O)\C=C\[C@H]1CCC(=O)N1CCCC1=CC=C(C(=O)OC)S1 AVZCAQNCYODQHK-TYXBMBSUSA-N 0.000 claims description 3
- JUSJTDLHSOSXJS-ALWTYZOZSA-N methyl 5-[3-[(2r)-2-[(e,3s)-3-hydroxy-4-methyl-7-phenylhept-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]prop-1-ynyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C#CCN1C(=O)CC[C@@H]1\C=C\[C@@H](O)C(C)CC#CC1=CC=CC=C1 JUSJTDLHSOSXJS-ALWTYZOZSA-N 0.000 claims description 3
- MPQNGSFETCOJTQ-ALWTYZOZSA-N methyl 5-[3-[(2r)-2-[(e,3s)-3-hydroxy-4-methyl-7-phenylhept-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)CC[C@@H]1\C=C\[C@@H](O)C(C)CC#CC1=CC=CC=C1 MPQNGSFETCOJTQ-ALWTYZOZSA-N 0.000 claims description 3
- ROBDZQUCFGAGKN-ALWTYZOZSA-N methyl 5-[3-[(2r)-2-[(e,3s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]prop-1-ynyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C#CCN1C(=O)CC[C@@H]1\C=C\[C@@H](O)C(C)CCCC1=CC=CC=C1 ROBDZQUCFGAGKN-ALWTYZOZSA-N 0.000 claims description 3
- LWTJYNJWUFYPPE-ALWTYZOZSA-N methyl 5-[3-[(2r)-2-[(e,3s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)CC[C@@H]1\C=C\[C@@H](O)C(C)CCCC1=CC=CC=C1 LWTJYNJWUFYPPE-ALWTYZOZSA-N 0.000 claims description 3
- VMFROVKJYQMOJO-KIEQSATHSA-N methyl 5-[3-[(2r)-2-[(e,3s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]prop-1-ynyl]thiophene-2-carboxylate Chemical compound CCC#CCC(C)[C@H](O)\C=C\[C@H]1CCC(=O)N1CC#CC1=CC=C(C(=O)OC)S1 VMFROVKJYQMOJO-KIEQSATHSA-N 0.000 claims description 3
- AVZCAQNCYODQHK-KXGHQGSMSA-N methyl 5-[3-[(2r)-2-[(e,3s,4r)-3-hydroxy-4-methylnon-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound CCC#CC[C@@H](C)[C@H](O)\C=C\[C@H]1CCC(=O)N1CCCC1=CC=C(C(=O)OC)S1 AVZCAQNCYODQHK-KXGHQGSMSA-N 0.000 claims description 3
- AVZCAQNCYODQHK-NIHFNGFISA-N methyl 5-[3-[(2r)-2-[(e,3s,4s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound CCC#CC[C@H](C)[C@H](O)\C=C\[C@H]1CCC(=O)N1CCCC1=CC=C(C(=O)OC)S1 AVZCAQNCYODQHK-NIHFNGFISA-N 0.000 claims description 3
- BCRHPIFEIDKGNM-CUWPLCDZSA-N methyl 5-[3-[(5R)-3,3-difluoro-5-[(E,3R,4S)-3-hydroxy-4-methyl-5-phenylpent-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound FC1(C(N([C@H](C1)C=C[C@@H]([C@H](CC1=CC=CC=C1)C)O)CCCC1=CC=C(S1)C(=O)OC)=O)F BCRHPIFEIDKGNM-CUWPLCDZSA-N 0.000 claims description 3
- VFBYHYHGZSKRPG-XKGZKEIXSA-N methyl 5-[3-[(5R)-3,3-difluoro-5-[(E,3R,4S)-3-hydroxy-4-phenylpent-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound FC1(C(N([C@H](C1)C=C[C@H]([C@@H](C)C1=CC=CC=C1)O)CCCC1=CC=C(S1)C(=O)OC)=O)F VFBYHYHGZSKRPG-XKGZKEIXSA-N 0.000 claims description 3
- MBEOOVLGUZLPHP-MLUCLSGHSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound CCC#CCC(C)[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(=O)OC)S1 MBEOOVLGUZLPHP-MLUCLSGHSA-N 0.000 claims description 3
- JETIPLMXLYZJNV-DMGQIGSTSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxyoct-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound CCCCC[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(=O)OC)S1 JETIPLMXLYZJNV-DMGQIGSTSA-N 0.000 claims description 3
- ZRZLHROEQSMNNK-DYRIQIPYSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyl-6-phenylhex-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)C(F)(F)C[C@@H]1\C=C\[C@H](O)[C@@H](C)CCC1=CC=CC=C1 ZRZLHROEQSMNNK-DYRIQIPYSA-N 0.000 claims description 3
- YDVKBTDHNPLJJJ-BQMVMUGMSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)C(F)(F)C[C@@H]1\C=C\[C@H](O)[C@@H](C)CCCC1=CC=CC=C1 YDVKBTDHNPLJJJ-BQMVMUGMSA-N 0.000 claims description 3
- JETIPLMXLYZJNV-IGXNXKSNSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3s)-3-hydroxyoct-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound CCCCC[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(=O)OC)S1 JETIPLMXLYZJNV-IGXNXKSNSA-N 0.000 claims description 3
- MBEOOVLGUZLPHP-OUHUKIOISA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4r)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound CCC#CC[C@@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(=O)OC)S1 MBEOOVLGUZLPHP-OUHUKIOISA-N 0.000 claims description 3
- BCRHPIFEIDKGNM-YAZIDRQLSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-5-phenylpent-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)C(F)(F)C[C@@H]1\C=C\[C@@H](O)[C@@H](C)CC1=CC=CC=C1 BCRHPIFEIDKGNM-YAZIDRQLSA-N 0.000 claims description 3
- ZRZLHROEQSMNNK-GJWBGHMGSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-6-phenylhex-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)C(F)(F)C[C@@H]1\C=C\[C@@H](O)[C@@H](C)CCC1=CC=CC=C1 ZRZLHROEQSMNNK-GJWBGHMGSA-N 0.000 claims description 3
- YDVKBTDHNPLJJJ-LKLUEYJESA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)C(F)(F)C[C@@H]1\C=C\[C@@H](O)[C@@H](C)CCCC1=CC=CC=C1 YDVKBTDHNPLJJJ-LKLUEYJESA-N 0.000 claims description 3
- MMODYAGSYAJBBK-WWTZYMIRSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-8-phenyloct-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)C(F)(F)C[C@@H]1\C=C\[C@@H](O)[C@@H](C)CCCCC1=CC=CC=C1 MMODYAGSYAJBBK-WWTZYMIRSA-N 0.000 claims description 3
- MBEOOVLGUZLPHP-OFQUAYIFSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound CCC#CC[C@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCC1=CC=C(C(=O)OC)S1 MBEOOVLGUZLPHP-OFQUAYIFSA-N 0.000 claims description 3
- VFBYHYHGZSKRPG-WDKHOGGPSA-N methyl 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-phenylpent-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1CCCN1C(=O)C(F)(F)C[C@@H]1\C=C\[C@H](O)[C@@H](C)C1=CC=CC=C1 VFBYHYHGZSKRPG-WDKHOGGPSA-N 0.000 claims description 3
- BGSLXPGZDJWFFO-MBJQPMTPSA-N methyl 7-[(2r)-2-[(e,3r)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]heptanoate Chemical compound C1CC(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\[C@H](O)C(C)CCCC1=CC=CC=C1 BGSLXPGZDJWFFO-MBJQPMTPSA-N 0.000 claims description 3
- BGSLXPGZDJWFFO-HECPXKJDSA-N methyl 7-[(2r)-2-[(e,3s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]heptanoate Chemical compound C1CC(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\[C@@H](O)C(C)CCCC1=CC=CC=C1 BGSLXPGZDJWFFO-HECPXKJDSA-N 0.000 claims description 3
- FCFQGZGDLMMISZ-PKPZZJCKSA-N methyl 7-[(2r)-2-[(e,3s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]heptanoate Chemical compound COC(=O)CCCCCCN1[C@@H](\C=C\[C@@H](O)C(C)CC#CC)CCC1=O FCFQGZGDLMMISZ-PKPZZJCKSA-N 0.000 claims description 3
- AHIJGACYLCKNAD-TYTHLOSQSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e)-3-hydroxy-4-methyl-7-phenylhept-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound C1C(F)(F)C(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\C(O)C(C)CC#CC1=CC=CC=C1 AHIJGACYLCKNAD-TYTHLOSQSA-N 0.000 claims description 3
- FSZQXOIHLKQMEG-OPJULODUSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e)-3-hydroxy-4-methyldec-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound CCCC#CCC(C)C(O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(=O)OC FSZQXOIHLKQMEG-OPJULODUSA-N 0.000 claims description 3
- HCKHINANORSZQG-KTRCDEGTSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e)-3-hydroxy-7-phenylhept-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound C1C(F)(F)C(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\C(O)CCC#CC1=CC=CC=C1 HCKHINANORSZQG-KTRCDEGTSA-N 0.000 claims description 3
- JBNVNCQHQOLBKU-ALXVWFSLSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound C1C(F)(F)C(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\[C@H](O)C(C)CCCC1=CC=CC=C1 JBNVNCQHQOLBKU-ALXVWFSLSA-N 0.000 claims description 3
- VHRJVUYFZQBEIY-CEGZRWDUSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound COC(=O)CCCCCCN1[C@@H](\C=C\[C@H](O)C(C)CC#CC)CC(F)(F)C1=O VHRJVUYFZQBEIY-CEGZRWDUSA-N 0.000 claims description 3
- AVYDNIUSLHLZJM-FYBNUODKSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxy-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound C1C(F)(F)C(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\[C@H](O)CCCCC1=CC=CC=C1 AVYDNIUSLHLZJM-FYBNUODKSA-N 0.000 claims description 3
- VHRJVUYFZQBEIY-FQQZZHAUSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3r,4r)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound COC(=O)CCCCCCN1[C@@H](\C=C\[C@H](O)[C@H](C)CC#CC)CC(F)(F)C1=O VHRJVUYFZQBEIY-FQQZZHAUSA-N 0.000 claims description 3
- NNQOPMDJSKGOML-SNLJXXQOSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound CCC#CC[C@H](C)[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(=O)OC NNQOPMDJSKGOML-SNLJXXQOSA-N 0.000 claims description 3
- VHRJVUYFZQBEIY-LPJXYHDHSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound COC(=O)CCCCCCN1[C@@H](\C=C\[C@H](O)[C@@H](C)CC#CC)CC(F)(F)C1=O VHRJVUYFZQBEIY-LPJXYHDHSA-N 0.000 claims description 3
- AVYDNIUSLHLZJM-IRAQTCESSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3s)-3-hydroxy-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound C1C(F)(F)C(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\[C@@H](O)CCCCC1=CC=CC=C1 AVYDNIUSLHLZJM-IRAQTCESSA-N 0.000 claims description 3
- JBNVNCQHQOLBKU-OAVCZXIDSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3s,4r)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound C1C(F)(F)C(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\[C@@H](O)[C@H](C)CCCC1=CC=CC=C1 JBNVNCQHQOLBKU-OAVCZXIDSA-N 0.000 claims description 3
- VHRJVUYFZQBEIY-KXZRJNSZSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3s,4r)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound COC(=O)CCCCCCN1[C@@H](\C=C\[C@@H](O)[C@H](C)CC#CC)CC(F)(F)C1=O VHRJVUYFZQBEIY-KXZRJNSZSA-N 0.000 claims description 3
- JBNVNCQHQOLBKU-PEQASXHNSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound C1C(F)(F)C(=O)N(CCCCCCC(=O)OC)[C@H]1\C=C\[C@@H](O)[C@@H](C)CCCC1=CC=CC=C1 JBNVNCQHQOLBKU-PEQASXHNSA-N 0.000 claims description 3
- NNQOPMDJSKGOML-QUMINBJRSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methylnon-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound CCC#CC[C@H](C)[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(=O)OC NNQOPMDJSKGOML-QUMINBJRSA-N 0.000 claims description 3
- VHRJVUYFZQBEIY-GPVXIOJZSA-N methyl 7-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-oxopyrrolidin-1-yl]heptanoate Chemical compound COC(=O)CCCCCCN1[C@@H](\C=C\[C@@H](O)[C@@H](C)CC#CC)CC(F)(F)C1=O VHRJVUYFZQBEIY-GPVXIOJZSA-N 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 150000003180 prostaglandins Chemical class 0.000 claims description 3
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims 38
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 12
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 claims 8
- AWMIWDCKBUKDKJ-XGRPXUFSSA-N 4-[2-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]ethyl]benzoic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCC=1C=CC(=CC=1)C(O)=O)CCC1=CC=CC=C1 AWMIWDCKBUKDKJ-XGRPXUFSSA-N 0.000 claims 2
- JMHMEEBPWHFLBX-AQLJEJBYSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyl-5-phenylpent-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)C1=CC=CC=C1 JMHMEEBPWHFLBX-AQLJEJBYSA-N 0.000 claims 2
- ZECQOPFVRSEFGC-XMUVQSOXSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyl-6-phenylhex-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CC1=CC=CC=C1 ZECQOPFVRSEFGC-XMUVQSOXSA-N 0.000 claims 2
- UXQWNSWYEJSWBM-DYRIQIPYSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CCC1=CC=CC=C1 UXQWNSWYEJSWBM-DYRIQIPYSA-N 0.000 claims 2
- WQNDXGHRPMQDFT-BQMVMUGMSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyl-8-phenyloct-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CCCC1=CC=CC=C1 WQNDXGHRPMQDFT-BQMVMUGMSA-N 0.000 claims 2
- AGGYHZMNJSBHQQ-VDRBLYDVSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3r,4s)-3-hydroxy-4-methyl-9-phenylnon-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CCCCC1=CC=CC=C1 AGGYHZMNJSBHQQ-VDRBLYDVSA-N 0.000 claims 2
- JMHMEEBPWHFLBX-KRPHMAJBSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-5-phenylpent-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)C1=CC=CC=C1 JMHMEEBPWHFLBX-KRPHMAJBSA-N 0.000 claims 2
- ZECQOPFVRSEFGC-QFVHRSDDSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-6-phenylhex-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CC1=CC=CC=C1 ZECQOPFVRSEFGC-QFVHRSDDSA-N 0.000 claims 2
- UXQWNSWYEJSWBM-GJWBGHMGSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-7-phenylhept-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CCC1=CC=CC=C1 UXQWNSWYEJSWBM-GJWBGHMGSA-N 0.000 claims 2
- WQNDXGHRPMQDFT-LKLUEYJESA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-8-phenyloct-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CCCC1=CC=CC=C1 WQNDXGHRPMQDFT-LKLUEYJESA-N 0.000 claims 2
- AGGYHZMNJSBHQQ-WWTZYMIRSA-N 5-[3-[(5r)-3,3-difluoro-5-[(e,3s,4s)-3-hydroxy-4-methyl-9-phenylnon-1-enyl]-2-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H](C)[C@H](O)\C=C\[C@@H]1N(C(=O)C(F)(F)C1)CCCC=1SC(=CC=1)C(O)=O)CCCCC1=CC=CC=C1 AGGYHZMNJSBHQQ-WWTZYMIRSA-N 0.000 claims 2
- TYKCTEYDUIYVJB-BYZSIXFTSA-N 7-[(2r)-2-[(e,3r)-3-hydroxy-5-phenylpent-1-en-4-ynyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C(/[C@@H](O)C#CC=1C=CC=CC=1)=C\[C@H]1CCC(=O)N1CCCCCCC(O)=O TYKCTEYDUIYVJB-BYZSIXFTSA-N 0.000 claims 2
- IQWSFXPFHDYOFM-AEKMKHNFSA-N 7-[(2r)-2-[(e,3r)-3-hydroxy-7-phenylhept-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C([C@@H](O)\C=C\[C@@H]1N(C(=O)CC1)CCCCCCC(O)=O)CC#CC1=CC=CC=C1 IQWSFXPFHDYOFM-AEKMKHNFSA-N 0.000 claims 2
- DEQPIOBZNPCKJE-AEKMKHNFSA-N 7-[(2r)-2-[(e,3r)-3-hydroxy-7-phenylhept-1-enyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C([C@@H](O)\C=C\[C@@H]1N(C(=O)CC1)CCCCCCC(O)=O)CCCC1=CC=CC=C1 DEQPIOBZNPCKJE-AEKMKHNFSA-N 0.000 claims 2
- TYKCTEYDUIYVJB-DQEWXYAXSA-N 7-[(2r)-2-[(e,3s)-3-hydroxy-5-phenylpent-1-en-4-ynyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C(/[C@H](O)C#CC=1C=CC=CC=1)=C\[C@H]1CCC(=O)N1CCCCCCC(O)=O TYKCTEYDUIYVJB-DQEWXYAXSA-N 0.000 claims 2
- IQWSFXPFHDYOFM-GLDDHKADSA-N 7-[(2r)-2-[(e,3s)-3-hydroxy-7-phenylhept-1-en-6-ynyl]-5-oxopyrrolidin-1-yl]heptanoic acid Chemical compound C([C@H](O)\C=C\[C@@H]1N(C(=O)CC1)CCCCCCC(O)=O)CC#CC1=CC=CC=C1 IQWSFXPFHDYOFM-GLDDHKADSA-N 0.000 claims 2
- PWZMQIUUWBQDQW-HMUVLFPJSA-N 7-[(5r)-3,3-difluoro-5-[(e,3r)-3-hydroxyoct-1-enyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CCCCC[C@@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(O)=O PWZMQIUUWBQDQW-HMUVLFPJSA-N 0.000 claims 2
- PWZMQIUUWBQDQW-WFPWZJHXSA-N 7-[(5r)-3,3-difluoro-5-[(e,3s)-3-hydroxyoct-1-enyl]-2-oxopyrrolidin-1-yl]heptanoic acid Chemical compound CCCCC[C@H](O)\C=C\[C@H]1CC(F)(F)C(=O)N1CCCCCCC(O)=O PWZMQIUUWBQDQW-WFPWZJHXSA-N 0.000 claims 2
- 101710151715 Protein 7 Proteins 0.000 claims 2
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
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- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Urology & Nephrology (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US201361856370P | 2013-07-19 | 2013-07-19 | |
| US61/856,370 | 2013-07-19 | ||
| US201461928843P | 2014-01-17 | 2014-01-17 | |
| US61/928,843 | 2014-01-17 | ||
| PCT/US2014/047138 WO2015009991A2 (en) | 2013-07-19 | 2014-07-18 | Methods, systems, and compositions for promoting bone growth |
Publications (2)
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| AU2014290512A1 true AU2014290512A1 (en) | 2015-11-12 |
| AU2014290512A8 AU2014290512A8 (en) | 2016-06-16 |
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| AU2014290512A Abandoned AU2014290512A1 (en) | 2013-07-19 | 2014-07-18 | Methods, systems, and compositions for promoting bone growth |
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| EP (1) | EP3021879A2 (enExample) |
| JP (1) | JP2016527006A (enExample) |
| KR (1) | KR20160048054A (enExample) |
| CN (1) | CN105392505A (enExample) |
| AU (1) | AU2014290512A1 (enExample) |
| CA (1) | CA2910398A1 (enExample) |
| PH (1) | PH12015502854A1 (enExample) |
| WO (1) | WO2015009991A2 (enExample) |
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| EP3176162B1 (en) | 2012-07-19 | 2020-05-27 | Cayman Chemical Company, Inc. | Difluorolactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated disease and conditions |
| JP2017525407A (ja) * | 2014-06-20 | 2017-09-07 | 株式会社スリー・ディー・マトリックス | 歯の骨間隙を充填するための材料および方法 |
| EP3617217B1 (en) | 2014-12-09 | 2022-09-07 | Warsaw Orthopedic, Inc. | Process for the production of oxysterols |
| WO2016196925A1 (en) * | 2015-06-04 | 2016-12-08 | The Regents Of The University Of California | Composition for bone and methods of making and using the same |
| CN105012995B (zh) * | 2015-06-04 | 2018-03-09 | 武汉维斯第医用科技股份有限公司 | 一种含促骨愈合药物的胶原蛋白海绵及其制备方法 |
| US9878070B2 (en) | 2015-06-17 | 2018-01-30 | Warsaw Orthopedic, Inc. | Malleable implants including an oxysterol and methods of use |
| US9877836B2 (en) | 2015-07-10 | 2018-01-30 | Warsaw Orthopedic, Inc. | Compression resistant implants including an oxysterol and methods of use |
| US9987289B2 (en) | 2015-07-10 | 2018-06-05 | Warsaw Orthopedic, Inc. | Slow release oxysterols and methods of use |
| US10632230B2 (en) | 2015-07-10 | 2020-04-28 | Warsaw Orthopedic, Inc. | Implants having a high drug load of an oxysterol and methods of use |
| US12171909B2 (en) | 2015-07-10 | 2024-12-24 | Warsaw Orthopedic, Inc. | Implants having a drug load of an oxysterol and methods of use |
| HU231033B1 (hu) | 2016-03-22 | 2019-12-30 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Eljárás 3-as kötést tartalmazó optikailag aktív karbonsavak, karbonsav sók és karbonsav származékok előállítására |
| CN105816919B (zh) * | 2016-05-23 | 2019-06-11 | 烟台正海生物科技股份有限公司 | 一种含有天然纳米羟基磷灰石的复合材料及其制备方法 |
| EP3526242A1 (en) | 2016-10-12 | 2019-08-21 | University of Copenhagen | Peptide dual agonists of gipr and glp2r |
| US11384114B2 (en) | 2016-12-09 | 2022-07-12 | Warsaw Orthopedic, Inc. | Polymorphic forms of an oxysterol and methods of making them |
| CN106699604B (zh) * | 2017-01-09 | 2019-01-01 | 四川同晟生物医药有限公司 | 一种沙库比曲及其中间体的制备方法 |
| US10434106B2 (en) | 2017-05-19 | 2019-10-08 | Warsaw Orthopedic, Inc. | Oxysterol-statin compounds for bone growth |
| US11464888B2 (en) | 2017-06-12 | 2022-10-11 | Warsaw Orthopedic, Inc. | Moldable formulations containing an oxysterol in an acellular tissue matrix |
| CN108822090B (zh) * | 2018-08-17 | 2020-11-17 | 杭州乐敦科技有限公司 | 一种他汀类药物中间体的制备方法 |
| CA3112625A1 (en) * | 2018-09-14 | 2020-03-19 | Orthocell Limited | Artificial periosteum for delivery of bone active agents |
| EP3902805A4 (en) | 2018-12-28 | 2023-03-01 | SPV Therapeutics Inc. | CYCLINE-DEPENDENT KINASE INHIBITORS |
| EP3920929A4 (en) * | 2019-02-04 | 2023-02-22 | Emory University | SCLEROSTIN INHIBITORS THAT PROMOTE EXPRESSION OF BONE MORPHOGENETIC PROTEINS |
| CN110590351B (zh) * | 2019-08-23 | 2021-05-25 | 中国科学院上海硅酸盐研究所 | 一种黑色生物活性陶瓷粉体及其应用 |
| CN114014647B (zh) * | 2021-10-21 | 2022-12-16 | 华南理工大学 | 一种硅酸锌复合磷酸三钙陶瓷支架及其制备方法与应用 |
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-
2014
- 2014-07-18 AU AU2014290512A patent/AU2014290512A1/en not_active Abandoned
- 2014-07-18 EP EP14750837.8A patent/EP3021879A2/en not_active Withdrawn
- 2014-07-18 CA CA2910398A patent/CA2910398A1/en not_active Abandoned
- 2014-07-18 US US14/905,663 patent/US10729810B2/en active Active
- 2014-07-18 JP JP2016527117A patent/JP2016527006A/ja active Pending
- 2014-07-18 WO PCT/US2014/047138 patent/WO2015009991A2/en not_active Ceased
- 2014-07-18 KR KR1020167001059A patent/KR20160048054A/ko not_active Withdrawn
- 2014-07-18 CN CN201480039423.2A patent/CN105392505A/zh active Pending
-
2015
- 2015-12-22 PH PH12015502854A patent/PH12015502854A1/en unknown
Also Published As
| Publication number | Publication date |
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| PH12015502854A1 (en) | 2016-03-28 |
| KR20160048054A (ko) | 2016-05-03 |
| US10729810B2 (en) | 2020-08-04 |
| WO2015009991A8 (en) | 2015-12-17 |
| CA2910398A1 (en) | 2015-01-22 |
| WO2015009991A2 (en) | 2015-01-22 |
| JP2016527006A (ja) | 2016-09-08 |
| WO2015009991A3 (en) | 2015-07-16 |
| AU2014290512A8 (en) | 2016-06-16 |
| US20160158413A1 (en) | 2016-06-09 |
| EP3021879A2 (en) | 2016-05-25 |
| CN105392505A (zh) | 2016-03-09 |
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