JP2017535515A5 - - Google Patents
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- Publication number
- JP2017535515A5 JP2017535515A5 JP2017514880A JP2017514880A JP2017535515A5 JP 2017535515 A5 JP2017535515 A5 JP 2017535515A5 JP 2017514880 A JP2017514880 A JP 2017514880A JP 2017514880 A JP2017514880 A JP 2017514880A JP 2017535515 A5 JP2017535515 A5 JP 2017535515A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethylbenzoyl
- hydroxy
- tert
- butyl
- carbohydrazide
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 239000001257 hydrogen Substances 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 21
- 239000012453 solvate Substances 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 16
- -1 -B (OH) 2 Chemical compound 0.000 claims 14
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 13
- 125000003107 substituted aryl group Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 9
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- RRSFXVIAIFZVSB-UHFFFAOYSA-N 2H-oxazaborinine-6-carbohydrazide Chemical compound O1NB=CC=C1C(=O)NN RRSFXVIAIFZVSB-UHFFFAOYSA-N 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 150000008064 anhydrides Chemical class 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 108090000623 proteins and genes Proteins 0.000 claims 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 4
- 125000005518 carboxamido group Chemical group 0.000 claims 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 4
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- RTDMKWGJUQKCRJ-UHFFFAOYSA-N oxaborole-5-carbohydrazide Chemical compound O1B=CC=C1C(=O)NN RTDMKWGJUQKCRJ-UHFFFAOYSA-N 0.000 claims 3
- RPBXPUFDEBMSMV-UHFFFAOYSA-N oxazaborepine-7-carbohydrazide Chemical compound O1N=BC=CC=C1C(=O)NN RPBXPUFDEBMSMV-UHFFFAOYSA-N 0.000 claims 3
- 108091033319 polynucleotide Proteins 0.000 claims 3
- 102000040430 polynucleotide Human genes 0.000 claims 3
- 239000002157 polynucleotide Substances 0.000 claims 3
- 241000238631 Hexapoda Species 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229920001184 polypeptide Polymers 0.000 claims 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- BNTVCWONOSYDEP-UHFFFAOYSA-N 2h-oxazaborinine Chemical compound N1OC=CC=B1 BNTVCWONOSYDEP-UHFFFAOYSA-N 0.000 claims 1
- JFEMHWVSALXNSW-AREMUKBSSA-N 3-(cyanomethoxy)-n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C(C(=C1OCC#N)C)=CC=C1B1OC(C)(C)C(C)(C)O1 JFEMHWVSALXNSW-AREMUKBSSA-N 0.000 claims 1
- GCUQFTCAAIVGTC-MUUNZHRXSA-N 3-(difluoromethoxy)-n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylhexan-3-yl]-2-methyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C(C(=C1OC(F)F)C)=CC=C1CCCB1OC(C)(C)C(C)(C)O1 GCUQFTCAAIVGTC-MUUNZHRXSA-N 0.000 claims 1
- OBWNEOCIDVZYBK-XMMPIXPASA-N 3-[4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylhexan-3-yl]amino]carbamoyl]-2-hydroxy-3-methylphenyl]propylboronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C1=CC=C(CCCB(O)O)C(O)=C1C OBWNEOCIDVZYBK-XMMPIXPASA-N 0.000 claims 1
- UWMMACCPPFLACV-RUZDIDTESA-N 3-[4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylhexan-3-yl]amino]carbamoyl]-2-methoxy-3-methylphenyl]propylboronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C1=CC=C(CCCB(O)O)C(OC)=C1C UWMMACCPPFLACV-RUZDIDTESA-N 0.000 claims 1
- OOPNOHXDSLMFPZ-UHFFFAOYSA-N 3-[4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-hydroxy-3-methylphenyl]propylboronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(O)C(CCCB(O)O)=CC=2)C)C(C)(C)C)=C1 OOPNOHXDSLMFPZ-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000019838 Blood disease Diseases 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- LXWUJSWUUJNQNO-UHFFFAOYSA-N C(C)(C)(C)N(NC(=O)C1=CC2=C(B(NN=C2)O)C=C1)C(C1=CC(=CC(=C1)C)C)=O Chemical compound C(C)(C)(C)N(NC(=O)C1=CC2=C(B(NN=C2)O)C=C1)C(C1=CC(=CC(=C1)C)C)=O LXWUJSWUUJNQNO-UHFFFAOYSA-N 0.000 claims 1
- FZBHLQDUKUABTI-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC(=C(C=C1)B(O)O)C=O Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC(=C(C=C1)B(O)O)C=O FZBHLQDUKUABTI-UHFFFAOYSA-N 0.000 claims 1
- XRBXPOJUONJPST-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC(=C(C=C1)B(O)O)NS(=O)(=O)C1=CC=CC=C1 Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC(=C(C=C1)B(O)O)NS(=O)(=O)C1=CC=CC=C1 XRBXPOJUONJPST-UHFFFAOYSA-N 0.000 claims 1
- RHXUOIICUWOVRY-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(N(C(=N2)NC(C)C)C(C)C)O)C=C1 Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(N(C(=N2)NC(C)C)C(C)C)O)C=C1 RHXUOIICUWOVRY-UHFFFAOYSA-N 0.000 claims 1
- FYKDRFDYVNLNOO-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(N(C(N2)=O)C2=CC=CC=C2)O)C=C1 Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(N(C(N2)=O)C2=CC=CC=C2)O)C=C1 FYKDRFDYVNLNOO-UHFFFAOYSA-N 0.000 claims 1
- QPWHXEXOSGPBNI-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(N(C(N2)=S)C2=CC=CC=C2)O)C=C1 Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(N(C(N2)=S)C2=CC=CC=C2)O)C=C1 QPWHXEXOSGPBNI-UHFFFAOYSA-N 0.000 claims 1
- JQEWSDHYLBFBLD-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(N(N=C2)C)O)C=C1 Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(N(N=C2)C)O)C=C1 JQEWSDHYLBFBLD-UHFFFAOYSA-N 0.000 claims 1
- YMFGKMBUKGYLEY-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(NN=C2)O)C=C1 Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(NN=C2)O)C=C1 YMFGKMBUKGYLEY-UHFFFAOYSA-N 0.000 claims 1
- HHLHIJKKPQXTHD-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=CN=CC(=C1C)OC)=O)C(=O)C1=C(C=C(C=C1)B(O)O)F Chemical compound C(C)(C)(C)N(NC(C1=CN=CC(=C1C)OC)=O)C(=O)C1=C(C=C(C=C1)B(O)O)F HHLHIJKKPQXTHD-UHFFFAOYSA-N 0.000 claims 1
- APFAWHAGGXFNKN-OAQYLSRUSA-N CC(C)([C@@H](CC)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC(=C(C=1)B(O)O)C=O)C Chemical compound CC(C)([C@@H](CC)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC(=C(C=1)B(O)O)C=O)C APFAWHAGGXFNKN-OAQYLSRUSA-N 0.000 claims 1
- RHVCJTHIKONXAC-JOCHJYFZSA-N CC(C)([C@@H](CC)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(N(N=C2)S(=O)(=O)C)O)C=1)C Chemical compound CC(C)([C@@H](CC)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(N(N=C2)S(=O)(=O)C)O)C=1)C RHVCJTHIKONXAC-JOCHJYFZSA-N 0.000 claims 1
- OJCSASVFVDSIFO-UHFFFAOYSA-N CC1(C)OB(C(C=CC(C(NN)=O)=C2C)=C2OCCOC)OC1(C)C Chemical compound CC1(C)OB(C(C=CC(C(NN)=O)=C2C)=C2OCCOC)OC1(C)C OJCSASVFVDSIFO-UHFFFAOYSA-N 0.000 claims 1
- SEGSYYAFLOFMRK-AREMUKBSSA-N CC=1C=C(C(=O)N(NC(=O)C2=CC3=C(B(N(C(N3)=S)C3=CC=CC=C3)O)C=C2)[C@@H](C(C)(C)C)CC)C=C(C=1)C Chemical compound CC=1C=C(C(=O)N(NC(=O)C2=CC3=C(B(N(C(N3)=S)C3=CC=CC=C3)O)C=C2)[C@@H](C(C)(C)C)CC)C=C(C=1)C SEGSYYAFLOFMRK-AREMUKBSSA-N 0.000 claims 1
- MGRHTYRCDSMPHE-OAQYLSRUSA-N CC=1C=C(C(=O)N(NC(=O)C2=CC3=C(B(NN=C3)O)C=C2)[C@@H](C(C)(C)C)CC)C=C(C=1)C Chemical compound CC=1C=C(C(=O)N(NC(=O)C2=CC3=C(B(NN=C3)O)C=C2)[C@@H](C(C)(C)C)CC)C=C(C=1)C MGRHTYRCDSMPHE-OAQYLSRUSA-N 0.000 claims 1
- XFPQVOQRTHJSPP-OAQYLSRUSA-N CC=1C=C(C(=O)N(NC(=O)C=2C=CC(=C(C=2)B(O)O)C=O)[C@@H](C(C)(C)C)CC)C=C(C=1)C Chemical compound CC=1C=C(C(=O)N(NC(=O)C=2C=CC(=C(C=2)B(O)O)C=O)[C@@H](C(C)(C)C)CC)C=C(C=1)C XFPQVOQRTHJSPP-OAQYLSRUSA-N 0.000 claims 1
- ZNLZBJVSHMOMIS-MUUNZHRXSA-N CC=1C=C(C(=O)N(NC(=O)C=2C=CC3=C(B(N(N=C3)S(=O)(=O)C3=CC=C(C)C=C3)O)C=2)[C@@H](C(C)(C)C)CC)C=C(C=1)C Chemical compound CC=1C=C(C(=O)N(NC(=O)C=2C=CC3=C(B(N(N=C3)S(=O)(=O)C3=CC=C(C)C=C3)O)C=2)[C@@H](C(C)(C)C)CC)C=C(C=1)C ZNLZBJVSHMOMIS-MUUNZHRXSA-N 0.000 claims 1
- XBHDYEJEPNNWHP-UHFFFAOYSA-N COC1=CC=CC(C(=O)NN(C(=O)C2=CC(N)=C(C=C2)B2OC(C)(C)C(C)(C)O2)C(C)(C)C)=C1C Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C2=CC(N)=C(C=C2)B2OC(C)(C)C(C)(C)O2)C(C)(C)C)=C1C XBHDYEJEPNNWHP-UHFFFAOYSA-N 0.000 claims 1
- 208000020446 Cardiac disease Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- NBZSSKOAYNUKMA-JOCHJYFZSA-N N'-(3,5-dimethylbenzoyl)-N'-[(3R)-2,2-dimethylpentan-3-yl]-1-hydroxy-2-methyl-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound CC=1C=C(C(=O)N(NC(=O)C=2C=CC3=C(B(N(N=C3)C)O)C=2)[C@@H](C(C)(C)C)CC)C=C(C=1)C NBZSSKOAYNUKMA-JOCHJYFZSA-N 0.000 claims 1
- FJHLOPPHQGZSOT-OAQYLSRUSA-N N'-(3,5-dimethylbenzoyl)-N'-[(3R)-2,2-dimethylpentan-3-yl]-1-hydroxy-2H-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound CC=1C=C(C(=O)N(NC(=O)C=2C=CC3=C(B(NN=C3)O)C=2)[C@@H](C(C)(C)C)CC)C=C(C=1)C FJHLOPPHQGZSOT-OAQYLSRUSA-N 0.000 claims 1
- VKMARDNAKOMLEA-UHFFFAOYSA-N N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-1-hydroxy-2-(4-methylphenyl)-3-oxo-4H-2,4,1-benzodiazaborinine-6-carbohydrazide Chemical compound C(C)(C)(C)N(NC(=O)C1=CC2=C(B(N(C(N2)=O)C2=CC=C(C=C2)C)O)C=C1)C(C1=CC(=CC(=C1)C)C)=O VKMARDNAKOMLEA-UHFFFAOYSA-N 0.000 claims 1
- CFTHIOJJOOLQOX-UHFFFAOYSA-N N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-1-hydroxy-2-phenyl-3-sulfanylidene-4H-2,4,1-benzodiazaborinine-6-carbohydrazide Chemical compound C(C)(C)(C)N(NC(=O)C1=CC2=C(B(N(C(N2)=S)C2=CC=CC=C2)O)C=C1)C(C1=CC(=CC(=C1)C)C)=O CFTHIOJJOOLQOX-UHFFFAOYSA-N 0.000 claims 1
- INBVLPKXBCPBGU-UHFFFAOYSA-N N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-1-hydroxy-2H-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC2=C(B(NN=C2)O)C=1)C(C1=CC(=CC(=C1)C)C)=O INBVLPKXBCPBGU-UHFFFAOYSA-N 0.000 claims 1
- BWZQWZQWQQFVMC-OAQYLSRUSA-N N-[(3R)-2,2-dimethylpentan-3-yl]-1-hydroxy-N'-(3-methoxy-2-methylbenzoyl)-2H-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound CC(C)([C@@H](CC)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(NN=C2)O)C=1)C BWZQWZQWQQFVMC-OAQYLSRUSA-N 0.000 claims 1
- SOGNLSHKZXDKKF-UHFFFAOYSA-N N-tert-butyl-1-hydroxy-N'-(3-methoxy-2-methylbenzoyl)-2-(4-methylphenyl)sulfonyl-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(N(N=C2)S(=O)(=O)C2=CC=C(C)C=C2)O)C=1 SOGNLSHKZXDKKF-UHFFFAOYSA-N 0.000 claims 1
- FYXZORJRBWFDGM-UHFFFAOYSA-N N-tert-butyl-1-hydroxy-N'-(3-methoxy-2-methylbenzoyl)-2-methyl-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(N(N=C2)C)O)C=1 FYXZORJRBWFDGM-UHFFFAOYSA-N 0.000 claims 1
- FCMYNTKEDPRXJK-UHFFFAOYSA-N N-tert-butyl-1-hydroxy-N'-(3-methoxy-2-methylbenzoyl)-2-methylsulfonyl-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(N(N=C2)S(=O)(=O)C)O)C=1 FCMYNTKEDPRXJK-UHFFFAOYSA-N 0.000 claims 1
- ZQQBANTUPIVZPM-UHFFFAOYSA-N N-tert-butyl-1-hydroxy-N'-(3-methoxy-2-methylbenzoyl)-2-phenyl-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(N(N=C2)C2=CC=CC=C2)O)C=1 ZQQBANTUPIVZPM-UHFFFAOYSA-N 0.000 claims 1
- XLRRTXCVWZAQII-UHFFFAOYSA-N N-tert-butyl-1-hydroxy-N'-(3-methoxy-2-methylbenzoyl)-2-propan-2-yl-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(N(N=C2)C(C)C)O)C=1 XLRRTXCVWZAQII-UHFFFAOYSA-N 0.000 claims 1
- UKOADNHPLJYVEH-UHFFFAOYSA-N N-tert-butyl-1-hydroxy-N'-(3-methoxy-2-methylbenzoyl)-2H-2,3,1-benzodiazaborinine-7-carbohydrazide Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC2=C(B(NN=C2)O)C=1 UKOADNHPLJYVEH-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 208000025747 Rheumatic disease Diseases 0.000 claims 1
- VFLLXNQWXADRMT-UHFFFAOYSA-N [2-(benzenesulfonamido)-4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]phenyl]boronic acid Chemical compound C(C)(C)(C)N(NC(=O)C1=CC(=C(C=C1)B(O)O)NS(=O)(=O)C1=CC=CC=C1)C(C1=CC(=CC(=C1)C)C)=O VFLLXNQWXADRMT-UHFFFAOYSA-N 0.000 claims 1
- RUXPXPFJSJNWCI-UHFFFAOYSA-N [2-[2,2-dimethylpentan-3-yl-[(3-methoxy-2-methylbenzoyl)amino]carbamoyl]phenyl]boronic acid Chemical compound C=1C=CC=C(B(O)O)C=1C(=O)N(C(CC)C(C)(C)C)NC(=O)C1=CC=CC(OC)=C1C RUXPXPFJSJNWCI-UHFFFAOYSA-N 0.000 claims 1
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- HSUZDILYFZMGMC-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(1-fluorobutan-2-yl)-2-methyl-3-[2-(oxan-2-yloxy)ethoxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(CF)CC)NC(=O)C(C(=C1OCCOC2OCCCC2)C)=CC=C1B1OC(C)(C)C(C)(C)O1 HSUZDILYFZMGMC-UHFFFAOYSA-N 0.000 claims 1
- OAFPNUPIACWEII-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(2,2-dimethylhexan-3-yl)-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(CCC)C(C)(C)C)NC(=O)C(C=1C)=CC=CC=1B1OC(C)(C)C(C)(C)O1 OAFPNUPIACWEII-UHFFFAOYSA-N 0.000 claims 1
- GMTIHIWPJCTTGO-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(2,2-dimethylpropyl)-1-hydroxy-6-methyl-3,4-dihydro-2,5,1-benzodioxaborepine-7-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(CC(C)(C)C)NC(=O)C=2C(=C3OCCOB(O)C3=CC=2)C)=C1 GMTIHIWPJCTTGO-UHFFFAOYSA-N 0.000 claims 1
- UWVMILXCAWDJBC-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(2,3-dimethylbutan-2-yl)-1-hydroxy-6-methyl-3,4-dihydro-2,5,1-benzodioxaborepine-7-carbohydrazide Chemical compound C=1C=C2B(O)OCCOC2=C(C)C=1C(=O)NN(C(C)(C)C(C)C)C(=O)C1=CC(C)=CC(C)=C1 UWVMILXCAWDJBC-UHFFFAOYSA-N 0.000 claims 1
- GASDPCROELWUKR-XMMPIXPASA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylhexan-3-yl]-2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C(C(=C1)F)=C(F)C=C1B1OC(C)(C)C(C)(C)O1 GASDPCROELWUKR-XMMPIXPASA-N 0.000 claims 1
- UOVPYGNOCHLJNO-RUZDIDTESA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylhexan-3-yl]-2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C(C(=C1)F)=CC=C1B1OC(C)(C)C(C)(C)O1 UOVPYGNOCHLJNO-RUZDIDTESA-N 0.000 claims 1
- OAFPNUPIACWEII-AREMUKBSSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylhexan-3-yl]-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C(C=1C)=CC=CC=1B1OC(C)(C)C(C)(C)O1 OAFPNUPIACWEII-AREMUKBSSA-N 0.000 claims 1
- CVTBLAFXLIRSMS-RUZDIDTESA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylhexan-3-yl]-3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C(C=C1F)=CC=C1B1OC(C)(C)C(C)(C)O1 CVTBLAFXLIRSMS-RUZDIDTESA-N 0.000 claims 1
- OETYRZDYZCUXTF-MUUNZHRXSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylhexan-3-yl]-3-hydroxy-2-methyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C(C(=C1O)C)=CC=C1CCCB1OC(C)(C)C(C)(C)O1 OETYRZDYZCUXTF-MUUNZHRXSA-N 0.000 claims 1
- LWWVLFLHIJQIML-GDLZYMKVSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylhexan-3-yl]-3-methoxy-2-methyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C(C(=C1OC)C)=CC=C1CCCB1OC(C)(C)C(C)(C)O1 LWWVLFLHIJQIML-GDLZYMKVSA-N 0.000 claims 1
- OEKNIVNJAALPDL-JOCHJYFZSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-1-hydroxy-6-methyl-3,4-dihydro-2,5,1-benzodioxaborepine-7-carbohydrazide Chemical compound C=1C=C2B(O)OCCOC2=C(C)C=1C(=O)NN([C@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 OEKNIVNJAALPDL-JOCHJYFZSA-N 0.000 claims 1
- GSFBEDCKFTZESK-XMMPIXPASA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C(C(=C1)F)=CC=C1B1OC(C)(C)C(C)(C)O1 GSFBEDCKFTZESK-XMMPIXPASA-N 0.000 claims 1
- XHZJSCMYPKUFJD-XMMPIXPASA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-2-fluoro-4-(methoxymethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C(C=1F)=CC=C(COC)C=1B1OC(C)(C)C(C)(C)O1 XHZJSCMYPKUFJD-XMMPIXPASA-N 0.000 claims 1
- FSEVKKDPJNIYCE-PBBFAOSKSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-2-methyl-3-[2-(oxan-2-yloxy)ethoxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C(C(=C1OCCOC2OCCCC2)C)=CC=C1B1OC(C)(C)C(C)(C)O1 FSEVKKDPJNIYCE-PBBFAOSKSA-N 0.000 claims 1
- OEKNIVNJAALPDL-QFIPXVFZSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3s)-2,2-dimethylpentan-3-yl]-1-hydroxy-6-methyl-3,4-dihydro-2,5,1-benzodioxaborepine-7-carbohydrazide Chemical compound C=1C=C2B(O)OCCOC2=C(C)C=1C(=O)NN([C@@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 OEKNIVNJAALPDL-QFIPXVFZSA-N 0.000 claims 1
- MTZLODGGTSSLFN-UHFFFAOYSA-N n'-(3-chloro-5-methylbenzoyl)-n'-(2,2-dimethylhexan-3-yl)-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound C=1C(C)=CC(Cl)=CC=1C(=O)N(C(CCC)C(C)(C)C)NC(=O)C(C=1C)=CC=CC=1B1OC(C)(C)C(C)(C)O1 MTZLODGGTSSLFN-UHFFFAOYSA-N 0.000 claims 1
- WPPYNPGZMDFMIV-UHFFFAOYSA-N n'-(3-chloro-5-methylbenzoyl)-n'-(2,2-dimethylpropyl)-1-hydroxy-6-methyl-3,4-dihydro-2,5,1-benzodioxaborepine-7-carbohydrazide Chemical compound CC1=CC(Cl)=CC(C(=O)N(CC(C)(C)C)NC(=O)C=2C(=C3OCCOB(O)C3=CC=2)C)=C1 WPPYNPGZMDFMIV-UHFFFAOYSA-N 0.000 claims 1
- UIZILZDYAHUOCE-RUZDIDTESA-N n'-[(3r)-2,2-dimethylpentan-3-yl]-3-methoxy-2-methyl-n'-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]benzohydrazide Chemical compound C=1C(C)=CC(B2OC(C)(C)C(C)(C)O2)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C1=CC=CC(OC)=C1C UIZILZDYAHUOCE-RUZDIDTESA-N 0.000 claims 1
- XJKCLEWYNBAXCI-XERRXZQWSA-N n'-[3,5-bis(trideuteriomethyl)benzoyl]-1-hydroxy-6-methyl-n'-(2-methylbutan-2-yl)-3,4-dihydro-2,5,1-benzodioxaborepine-7-carbohydrazide Chemical compound [2H]C([2H])([2H])C1=CC(C([2H])([2H])[2H])=CC(C(=O)N(NC(=O)C=2C(=C3OCCOB(O)C3=CC=2)C)C(C)(C)CC)=C1 XJKCLEWYNBAXCI-XERRXZQWSA-N 0.000 claims 1
- OEKNIVNJAALPDL-RJMZWKRVSA-N n'-[3,5-bis(trideuteriomethyl)benzoyl]-n'-[(3s)-2,2-dimethylpentan-3-yl]-1-hydroxy-6-methyl-3,4-dihydro-2,5,1-benzodioxaborepine-7-carbohydrazide Chemical compound [2H]C([2H])([2H])C1=CC(C([2H])([2H])[2H])=CC(C(=O)N(NC(=O)C=2C(=C3OCCOB(O)C3=CC=2)C)[C@@H](CC)C(C)(C)C)=C1 OEKNIVNJAALPDL-RJMZWKRVSA-N 0.000 claims 1
- YIUJPCXJPWTPPU-UHFFFAOYSA-N n'-tert-butyl-3-(cyanomethoxy)-n'-(3,5-dimethylbenzoyl)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(OCC#N)C(B3OC(C)(C)C(C)(C)O3)=CC=2)C)C(C)(C)C)=C1 YIUJPCXJPWTPPU-UHFFFAOYSA-N 0.000 claims 1
- AZVDCLBYATVIMX-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-1-hydroxy-6-methyl-3,4-dihydro-2,5,1-benzodioxaborepine-7-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3OCCOB(O)C3=CC=2)C)C(C)(C)C)=C1 AZVDCLBYATVIMX-UHFFFAOYSA-N 0.000 claims 1
- ABUOQMUCWRJISQ-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=CC(=CC=2F)B2OC(C)(C)C(C)(C)O2)F)C(C)(C)C)=C1 ABUOQMUCWRJISQ-UHFFFAOYSA-N 0.000 claims 1
- JYCHDVRWYJDFKF-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-2-fluoro-4-(methoxymethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound FC1=C(B2OC(C)(C)C(C)(C)O2)C(COC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 JYCHDVRWYJDFKF-UHFFFAOYSA-N 0.000 claims 1
- QEENMCMVNSBJHG-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(B3OC(C)(C)C(C)(C)O3)C=CC=2)C)C(C)(C)C)=C1 QEENMCMVNSBJHG-UHFFFAOYSA-N 0.000 claims 1
- DVOKGGIZMRROPI-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-2-methyl-3-[2-(oxan-2-yloxy)ethoxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(OCCOC3OCCCC3)C(B3OC(C)(C)C(C)(C)O3)=CC=2)C)C(C)(C)C)=C1 DVOKGGIZMRROPI-UHFFFAOYSA-N 0.000 claims 1
- XDTPGPOZXQRHMX-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C=C(F)C(B3OC(C)(C)C(C)(C)O3)=CC=2)C(C)(C)C)=C1 XDTPGPOZXQRHMX-UHFFFAOYSA-N 0.000 claims 1
- YLTQLGXSXUVBNA-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-3-hydroxy-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(O)C(B3OC(C)(C)C(C)(C)O3)=CC=2)C)C(C)(C)C)=C1 YLTQLGXSXUVBNA-UHFFFAOYSA-N 0.000 claims 1
- MUSXAQYFHGWLNH-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-3-hydroxy-2-methyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]benzohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(O)C(CCCB3OC(C)(C)C(C)(C)O3)=CC=2)C)C(C)(C)C)=C1 MUSXAQYFHGWLNH-UHFFFAOYSA-N 0.000 claims 1
- DSZTXHUPHSUQPS-UHFFFAOYSA-N n-(2,2-dimethylhexan-3-yl)-n'-[2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]-2-oxo-1h-pyridine-3-carbohydrazide Chemical compound C=1C=CNC(=O)C=1C(=O)N(C(CCC)C(C)(C)C)NC(=O)C(C=1C)=CC=CC=1B1OC(C)(C)C(C)(C)O1 DSZTXHUPHSUQPS-UHFFFAOYSA-N 0.000 claims 1
- NZVOAZRENDZQAF-UHFFFAOYSA-N n-(2,2-dimethylpentan-3-yl)-3,5-dimethoxy-4-methyl-n'-[2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]benzohydrazide Chemical compound C=1C(OC)=C(C)C(OC)=CC=1C(=O)N(C(CC)C(C)(C)C)NC(=O)C(C=1C)=CC=CC=1B1OC(C)(C)C(C)(C)O1 NZVOAZRENDZQAF-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 claims 1
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| US10070649B2 (en) | 2013-01-30 | 2018-09-11 | Agrofresh Inc. | Volatile applications against pathogens |
| NZ712167A (en) | 2013-03-15 | 2018-05-25 | Intrexon Corp | Boron-containing diacylhydrazines |
| EP3134418A4 (en) * | 2014-04-23 | 2018-01-03 | The Research Foundation for The State University of New York | A rapid and efficient bioorthogonal ligation reaction and boron-containing heterocycles useful in conjuction therewith |
| WO2017155879A1 (en) | 2016-03-07 | 2017-09-14 | Agrofresh Inc. | Synergistic methods of using benzoxaborole compounds and preservative gases as an antimicrobial for crops |
| FR3093641B1 (fr) * | 2019-03-15 | 2023-11-03 | Biophytis | Phytoecdysones et leurs dérivés pour leur utilisation dans le traitement de l’altération de la fonction respiratoire |
| KR102803900B1 (ko) | 2019-09-30 | 2025-05-12 | 삼성디스플레이 주식회사 | 발광 소자 및 발광 소자용 다환 화합물 |
| CN113336781A (zh) * | 2021-06-15 | 2021-09-03 | 江西同和药业股份有限公司 | 一种克立硼罗的制备方法 |
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-
2015
- 2015-09-16 US US14/855,646 patent/US9944659B2/en not_active Expired - Fee Related
- 2015-09-16 WO PCT/US2015/050375 patent/WO2016044390A1/en not_active Ceased
- 2015-09-16 MX MX2017003403A patent/MX2017003403A/es unknown
- 2015-09-16 TW TW104130627A patent/TW201625650A/zh unknown
- 2015-09-16 EP EP15842247.7A patent/EP3194359B1/en active Active
- 2015-09-16 SG SG11201701944WA patent/SG11201701944WA/en unknown
- 2015-09-16 CN CN201580062177.7A patent/CN107406373B/zh not_active Expired - Fee Related
- 2015-09-16 CA CA2961738A patent/CA2961738A1/en not_active Abandoned
- 2015-09-16 AU AU2015317862A patent/AU2015317862A1/en not_active Abandoned
- 2015-09-16 JP JP2017514880A patent/JP6567657B2/ja not_active Expired - Fee Related
-
2017
- 2017-03-09 IL IL251073A patent/IL251073A0/en unknown
-
2018
- 2018-03-08 US US15/915,415 patent/US10570158B2/en not_active Expired - Fee Related
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