JP2016536348A5 - - Google Patents
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- Publication number
- JP2016536348A5 JP2016536348A5 JP2016545243A JP2016545243A JP2016536348A5 JP 2016536348 A5 JP2016536348 A5 JP 2016536348A5 JP 2016545243 A JP2016545243 A JP 2016545243A JP 2016545243 A JP2016545243 A JP 2016545243A JP 2016536348 A5 JP2016536348 A5 JP 2016536348A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrol
- octahydrocyclopenta
- hydroxy
- benzyl
- rac
- 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 —OC (O) Oalkyl Chemical group 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 72
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000000651 prodrug Substances 0.000 claims description 17
- 229940002612 prodrug Drugs 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 125000005466 alkylenyl group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 14
- 235000010290 biphenyl Nutrition 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- JTWNGNLQNPZTSM-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-5-ol Chemical compound C1NCC2CC(O)CC21 JTWNGNLQNPZTSM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 6
- PFQYYQCYAUKHMU-ZQCLUDFMSA-N O[C@@H](CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1)c1ccc(O)cc1 Chemical compound O[C@@H](CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1)c1ccc(O)cc1 PFQYYQCYAUKHMU-ZQCLUDFMSA-N 0.000 claims description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- XRRDFIPYLFCYLU-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical group [CH2]C1=CC(C)=CC(C)=C1 XRRDFIPYLFCYLU-UHFFFAOYSA-N 0.000 claims description 4
- APQPXQPJQDJASQ-BHWSWFIUSA-N 4-[2-[(3aR,6aS)-5-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1-hydroxyethyl]-2-fluorophenol Chemical compound C([C@H]1CN(C[C@H]1C1)CC(O)C=2C=C(F)C(O)=CC=2)C1CC1=CC=CC=C1 APQPXQPJQDJASQ-BHWSWFIUSA-N 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- HCJJHOOZJPOUQO-HGBKABEASA-N C(C1=CC=CC=C1)C1C[C@@H]2[C@@H](CN(C2)CC(O)C2=CC=C(C=C2)O)C1 Chemical compound C(C1=CC=CC=C1)C1C[C@@H]2[C@@H](CN(C2)CC(O)C2=CC=C(C=C2)O)C1 HCJJHOOZJPOUQO-HGBKABEASA-N 0.000 claims description 4
- ZMXDIGRWFXFDSK-FWZHVETRSA-N O[C@H](CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1)c1ccc(O)c(F)c1 Chemical compound O[C@H](CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1)c1ccc(O)c(F)c1 ZMXDIGRWFXFDSK-FWZHVETRSA-N 0.000 claims description 4
- PFQYYQCYAUKHMU-AFTWLNQJSA-N O[C@H](CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1)c1ccc(O)cc1 Chemical compound O[C@H](CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1)c1ccc(O)cc1 PFQYYQCYAUKHMU-AFTWLNQJSA-N 0.000 claims description 4
- XCEHEPNIWGDJSA-QIDMFYOTSA-N Oc1ccc(cc1)C(=O)CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1 Chemical compound Oc1ccc(cc1)C(=O)CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1 XCEHEPNIWGDJSA-QIDMFYOTSA-N 0.000 claims description 4
- RESCXVGYLBDWJR-DIZYECFSSA-N [H][C@@]12CC(CCC3=CC=CC=C3)C[C@]1([H])CN(C2)C(C)C(=O)C1=CC=C(O)C=C1 Chemical compound [H][C@@]12CC(CCC3=CC=CC=C3)C[C@]1([H])CN(C2)C(C)C(=O)C1=CC=C(O)C=C1 RESCXVGYLBDWJR-DIZYECFSSA-N 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- QZPCSULOKOSWNR-JNKARSBBSA-N (3aR,6aS)-2-[2-(3-fluoro-4-hydroxyphenyl)-2-hydroxyethyl]-5-(thiophen-2-ylmethyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound OC(CN1C[C@H]2CC(O)(Cc3cccs3)C[C@H]2C1)c1ccc(O)c(F)c1 QZPCSULOKOSWNR-JNKARSBBSA-N 0.000 claims description 2
- VYOMOXYFWDGTBY-BAUKFBFWSA-N (3aR,6aS)-2-[2-hydroxy-2-(5-hydroxypyridin-2-yl)ethyl]-5-(thiophen-2-ylmethyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound OC(CN1C[C@H]2CC(O)(Cc3cccs3)C[C@H]2C1)c1ccc(O)cn1 VYOMOXYFWDGTBY-BAUKFBFWSA-N 0.000 claims description 2
- NSJHOSQXVMTFQM-RGMRCXJASA-N (3aR,6aS)-5-[(2,4-difluorophenyl)methyl]-2-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound OC(CN1C[C@H]2CC(O)(Cc3ccc(F)cc3F)C[C@H]2C1)c1ccc(O)cc1 NSJHOSQXVMTFQM-RGMRCXJASA-N 0.000 claims description 2
- AZLDSEZCQWHGHA-XBLGPDGASA-N (3aR,6aS)-5-[(2-fluorophenyl)methyl]-2-[2-hydroxy-2-(5-hydroxypyridin-2-yl)ethyl]-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound OC(CN1C[C@H]2CC(O)(Cc3ccccc3F)C[C@H]2C1)c1ccc(O)cn1 AZLDSEZCQWHGHA-XBLGPDGASA-N 0.000 claims description 2
- WEMHIAGNPGOQRU-VSOVRNOCSA-N (3aR,6aS)-5-benzyl-5-hydroxy-N-(3-isocyanophenyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound OC1(Cc2ccccc2)C[C@@H]2CN(C[C@@H]2C1)C(=O)Nc1cccc(c1)[N+]#[C-] WEMHIAGNPGOQRU-VSOVRNOCSA-N 0.000 claims description 2
- MWMWEMIEPGTVSP-YLQYIJTPSA-N (3aR,6aS)-5-hydroxy-5-(3-methoxyphenyl)-N-[3-(trifluoromethyl)phenyl]-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound COc1cccc(c1)C1(O)C[C@@H]2CN(C[C@@H]2C1)C(=O)Nc1cccc(c1)C(F)(F)F MWMWEMIEPGTVSP-YLQYIJTPSA-N 0.000 claims description 2
- VBKPXXQYVGKMHK-MIJOPJBOSA-N (3aR,6aS)-N-[(1R)-1-(4-chlorophenyl)ethyl]-5-phenyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxamide Chemical compound C[C@@H](NC(=O)N1C[C@@H]2CC(C[C@@H]2C1)c1ccccc1)c1ccc(Cl)cc1 VBKPXXQYVGKMHK-MIJOPJBOSA-N 0.000 claims description 2
- WXJNBVAQZMIKCE-PMQSPZGISA-N (3aS,6aR)-2-[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]-5-(2-methylphenyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound CC(C(O)c1ccc(O)cc1)N1C[C@H]2CC(O)(C[C@H]2C1)c1ccccc1C WXJNBVAQZMIKCE-PMQSPZGISA-N 0.000 claims description 2
- SBUZGMJCINGHKO-BURSYGDYSA-N (3aS,6aR)-2-[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]-5-(3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound COc1cccc(c1)C1(O)C[C@@H]2CN(C[C@@H]2C1)C(C)C(O)c1ccc(O)cc1 SBUZGMJCINGHKO-BURSYGDYSA-N 0.000 claims description 2
- CPOVDNSVLDVVSG-BXBLUCELSA-N (3aS,6aR)-2-[2-(2,4-dichlorophenyl)-2-hydroxyethyl]-5-(3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound COc1cccc(c1)C1(O)C[C@@H]2CN(CC(O)c3ccc(Cl)cc3Cl)C[C@@H]2C1 CPOVDNSVLDVVSG-BXBLUCELSA-N 0.000 claims description 2
- SIGYQMUQWMMSCD-HJIICKRWSA-N (3aS,6aR)-5-(4-tert-butylphenyl)-2-[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound CC(C(O)c1ccc(O)cc1)N1C[C@H]2CC(O)(C[C@H]2C1)c1ccc(cc1)C(C)(C)C SIGYQMUQWMMSCD-HJIICKRWSA-N 0.000 claims description 2
- RQOLBIBZMGXZGB-KLHFOMLHSA-N (3aS,6aR)-5-benzyl-2-[2-hydroxy-2-(5-hydroxypyrimidin-2-yl)ethyl]-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-5-ol Chemical compound OC(CN1C[C@H]2CC(O)(Cc3ccccc3)C[C@H]2C1)c1ncc(O)cn1 RQOLBIBZMGXZGB-KLHFOMLHSA-N 0.000 claims description 2
- YYYZLOJZUGBUIK-DBIVSCPCSA-N (3aS,6aR)-5-hydroxy-5-phenyl-N-[3-(trifluoromethyl)phenyl]-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound OC1(C[C@@H]2CN(C[C@@H]2C1)C(=O)Nc1cccc(c1)C(F)(F)F)c1ccccc1 YYYZLOJZUGBUIK-DBIVSCPCSA-N 0.000 claims description 2
- IUOYVWOXGSUNHI-GWTOYCKXSA-N (3aS,6aR)-5-hydroxy-N-(3-methoxyphenyl)-5-phenyl-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound COc1cccc(NC(=O)N2C[C@H]3CC(O)(C[C@H]3C2)c2ccccc2)c1 IUOYVWOXGSUNHI-GWTOYCKXSA-N 0.000 claims description 2
- VPJMVLYBHCIDKJ-AQKKSAQBSA-N (3aS,6aR)-5-hydroxy-N-(4-methoxyphenyl)-5-(2-methylphenyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound COc1ccc(NC(=O)N2C[C@H]3CC(O)(C[C@H]3C2)c2ccccc2C)cc1 VPJMVLYBHCIDKJ-AQKKSAQBSA-N 0.000 claims description 2
- IBXXYQUJTVQCPF-DBIVSCPCSA-N (3aS,6aR)-N-(3-chlorophenyl)-5-hydroxy-5-phenyl-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound OC1(C[C@@H]2CN(C[C@@H]2C1)C(=O)Nc1cccc(Cl)c1)c1ccccc1 IBXXYQUJTVQCPF-DBIVSCPCSA-N 0.000 claims description 2
- DZDBLXQHFIZAAW-GWTOYCKXSA-N (3aS,6aR)-N-(4-fluorophenyl)-5-hydroxy-5-(2-methylphenyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound Cc1ccccc1C1(O)C[C@@H]2CN(C[C@@H]2C1)C(=O)Nc1ccc(F)cc1 DZDBLXQHFIZAAW-GWTOYCKXSA-N 0.000 claims description 2
- LRYLRPDMQKPKSR-DBIVSCPCSA-N (3aS,6aR)-N-(4-fluorophenyl)-5-hydroxy-5-phenyl-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound OC1(C[C@@H]2CN(C[C@@H]2C1)C(=O)Nc1ccc(F)cc1)c1ccccc1 LRYLRPDMQKPKSR-DBIVSCPCSA-N 0.000 claims description 2
- PHUWIPHSPPUUSA-DFPSAQRASA-N (3aS,6aR)-N-[(1R)-1-(4-chlorophenyl)ethyl]-5-hydroxy-5-phenyl-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxamide Chemical compound C[C@@H](NC(=O)N1C[C@H]2CC(O)(C[C@H]2C1)c1ccccc1)c1ccc(Cl)cc1 PHUWIPHSPPUUSA-DFPSAQRASA-N 0.000 claims description 2
- FIYMUDZJRXYWEK-UHFFFAOYSA-N 1-(3-fluorophenyl)-2-(5-hydroxy-5-phenyl-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)ethanone Chemical compound OC1(CC2CN(CC(=O)c3cccc(F)c3)CC2C1)c1ccccc1 FIYMUDZJRXYWEK-UHFFFAOYSA-N 0.000 claims description 2
- NPABWUSBHDDOIE-UHFFFAOYSA-N 1-(3-fluorophenyl)-2-[5-hydroxy-5-(3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl]ethanone Chemical compound COc1cccc(c1)C1(O)CC2CN(CC(=O)c3cccc(F)c3)CC2C1 NPABWUSBHDDOIE-UHFFFAOYSA-N 0.000 claims description 2
- ZUEIFROVSPJZID-UHFFFAOYSA-N 1-(3-methoxyphenyl)-2-(5-phenyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)ethanol Chemical compound COc1cccc(c1)C(O)CN1CC2CC(CC2C1)c1ccccc1 ZUEIFROVSPJZID-UHFFFAOYSA-N 0.000 claims description 2
- WUOKNHZBPBQFKF-UHFFFAOYSA-N 2-(5-hydroxy-5-phenyl-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl)-1-[4-(2-hydroxypropan-2-yl)phenyl]ethanone Chemical compound OC1(CC2C(CN(C2)CC(=O)C2=CC=C(C=C2)C(C)(C)O)C1)C1=CC=CC=C1 WUOKNHZBPBQFKF-UHFFFAOYSA-N 0.000 claims description 2
- TZRWHKGJPHYGTE-DETIRCLXSA-N 2-[(3aS,6aR)-5-hydroxy-5-(2-phenylethyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-1-(4-hydroxyphenyl)ethanone Chemical compound Oc1ccc(cc1)C(=O)CN1C[C@H]2CC(O)(CCc3ccccc3)C[C@H]2C1 TZRWHKGJPHYGTE-DETIRCLXSA-N 0.000 claims description 2
- NTEMGKPIJVFNOH-UHFFFAOYSA-N 2-[5-hydroxy-5-(2-phenylethyl)-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-1-[4-(3-methylphenyl)phenyl]ethanone Chemical compound Cc1cccc(c1)-c1ccc(cc1)C(=O)CN1CC2CC(O)(CCc3ccccc3)CC2C1 NTEMGKPIJVFNOH-UHFFFAOYSA-N 0.000 claims description 2
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- AXKPQCBUIPSASF-HLVUACMISA-N 3-[2-[(3aR,6aS)-5-benzyl-5-hydroxy-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrol-2-yl]acetyl]-3H-pyridazin-6-one Chemical compound OC1(Cc2ccccc2)C[C@@H]2CN(CC(=O)C3C=CC(=O)N=N3)C[C@@H]2C1 AXKPQCBUIPSASF-HLVUACMISA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- VMKIBZYOSZSRRE-TZKKQGAMSA-N 6-[2-[(3aS,6aR)-5-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1-hydroxyethyl]pyridin-3-ol Chemical compound [H][C@@]12CC(CC3=CC=CC=C3)C[C@]1([H])CN(CC(O)C1=CC=C(O)C=N1)C2 VMKIBZYOSZSRRE-TZKKQGAMSA-N 0.000 claims description 2
- PFQYYQCYAUKHMU-QXXBNALYSA-N C(C1=CC=CC=C1)C1(CC2C(CN(C2)C[C@H](C2=CC=C(C=C2)O)O)C1)O Chemical class C(C1=CC=CC=C1)C1(CC2C(CN(C2)C[C@H](C2=CC=C(C=C2)O)O)C1)O PFQYYQCYAUKHMU-QXXBNALYSA-N 0.000 claims description 2
- GSHLJAKBPQOIHN-YQQQUEKLSA-N C(C1=CC=CC=C1)C1C[C@@H]2[C@@H](CN(C2)C(=O)NC2=CC(=CC=C2)OC)C1 Chemical compound C(C1=CC=CC=C1)C1C[C@@H]2[C@@H](CN(C2)C(=O)NC2=CC(=CC=C2)OC)C1 GSHLJAKBPQOIHN-YQQQUEKLSA-N 0.000 claims description 2
- KOKCXVREFYJHHZ-JKKSXJTRSA-N C(C1=CC=CC=C1)C1C[C@@H]2[C@@H](CN(C2)C(C(=O)C2=CC=C(C=C2)O)C)C1 Chemical compound C(C1=CC=CC=C1)C1C[C@@H]2[C@@H](CN(C2)C(C(=O)C2=CC=C(C=C2)O)C)C1 KOKCXVREFYJHHZ-JKKSXJTRSA-N 0.000 claims description 2
- BAJUYSVVGOEBEF-CTXDPNEZSA-N C(C1=CC=CC=C1)C1C[C@@H]2[C@@H](CN(C2)CC(=O)C2=CC=C(C=C2)O)C1 Chemical compound C(C1=CC=CC=C1)C1C[C@@H]2[C@@H](CN(C2)CC(=O)C2=CC=C(C=C2)O)C1 BAJUYSVVGOEBEF-CTXDPNEZSA-N 0.000 claims description 2
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2014
- 2014-09-26 EP EP18202051.1A patent/EP3461827B1/en active Active
- 2014-09-26 TW TW103133682A patent/TW201605791A/zh unknown
- 2014-09-26 CN CN201480058773.3A patent/CN105916843B/zh active Active
- 2014-09-26 ES ES18202051T patent/ES2910848T3/es active Active
- 2014-09-26 ES ES14849302T patent/ES2707739T3/es active Active
- 2014-09-26 US US14/498,462 patent/US9540324B2/en active Active
- 2014-09-26 AR ARP140103584A patent/AR097794A1/es unknown
- 2014-09-26 UY UY0001035750A patent/UY35750A/es not_active Application Discontinuation
- 2014-09-26 JP JP2016545243A patent/JP6546596B2/ja active Active
- 2014-09-26 EP EP14849302.6A patent/EP3036221B1/en active Active
- 2014-09-26 WO PCT/US2014/057800 patent/WO2015048507A1/en not_active Ceased
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2016
- 2016-11-23 US US15/360,824 patent/US10052306B2/en active Active
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2018
- 2018-07-23 US US16/042,806 patent/US11116749B2/en active Active
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2021
- 2021-08-10 US US17/398,622 patent/US12161624B2/en active Active
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