CA2961738A1 - Boron-containing diacylhydrazine compounds - Google Patents
Boron-containing diacylhydrazine compounds Download PDFInfo
- Publication number
- CA2961738A1 CA2961738A1 CA2961738A CA2961738A CA2961738A1 CA 2961738 A1 CA2961738 A1 CA 2961738A1 CA 2961738 A CA2961738 A CA 2961738A CA 2961738 A CA2961738 A CA 2961738A CA 2961738 A1 CA2961738 A1 CA 2961738A1
- Authority
- CA
- Canada
- Prior art keywords
- dimethylbenzoyl
- hydroxy
- carbohydrazide
- tert
- butyl
- 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
Links
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title abstract 3
- 229910052796 boron Inorganic materials 0.000 title abstract 3
- 125000005077 diacylhydrazine group Chemical group 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 61
- 239000012453 solvate Substances 0.000 claims abstract 61
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 13
- 108090000623 proteins and genes Proteins 0.000 claims abstract 9
- 201000010099 disease Diseases 0.000 claims abstract 6
- 230000014509 gene expression Effects 0.000 claims abstract 6
- 108010057988 ecdysone receptor Proteins 0.000 claims abstract 2
- 102000004169 proteins and genes Human genes 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 63
- 150000008064 anhydrides Chemical class 0.000 claims 51
- 229910052739 hydrogen Inorganic materials 0.000 claims 48
- 239000001257 hydrogen Substances 0.000 claims 48
- 150000002431 hydrogen Chemical class 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 125000003107 substituted aryl group Chemical group 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 238000000034 method Methods 0.000 claims 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic 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
- -1 -B(OH)2 Chemical compound 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- 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
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 208000027418 Wounds and injury Diseases 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 230000006378 damage Effects 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 208000014674 injury Diseases 0.000 claims 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000004390 alkyl sulfonyl 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
- 108091033319 polynucleotide Proteins 0.000 claims 4
- 102000040430 polynucleotide Human genes 0.000 claims 4
- 239000002157 polynucleotide Substances 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 108020001756 ligand binding domains Proteins 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000019838 Blood disease Diseases 0.000 claims 2
- 208000020446 Cardiac disease Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 241000238631 Hexapoda Species 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- QXWFXSMAYBJQBF-OAQYLSRUSA-N N-[(3R)-2,2-dimethylpentan-3-yl]-1-hydroxy-N'-(3-methoxy-2-methylbenzoyl)-2,3,1-benzoxazaborinine-7-carbohydrazide Chemical compound CC(C)([C@@H](CC)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(C=NOB2O)C=C1)C QXWFXSMAYBJQBF-OAQYLSRUSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000022873 Ocular disease Diseases 0.000 claims 2
- 208000025747 Rheumatic disease Diseases 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 208000007502 anemia Diseases 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 208000014951 hematologic disease Diseases 0.000 claims 2
- 208000018706 hematopoietic system disease Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 230000002503 metabolic effect Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- ZBHMBIZMNYYTMF-UHFFFAOYSA-N 2-acetyl-N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-1-hydroxy-2,3,1-benzodiazaborinine-6-carbohydrazide Chemical compound C(C)(=O)N1N=CC2=C(B1O)C=CC(=C2)C(=O)NN(C(C1=CC(=CC(=C1)C)C)=O)C(C)(C)C ZBHMBIZMNYYTMF-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
- PTWJOXNRRWDXDI-UHFFFAOYSA-N C(C)(C)(C)N(NC(=O)C1=CC2=C(B(N(N=C2)C2=CC=CC=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(N(N=C2)C2=CC=CC=C2)O)C=C1)C(C1=CC(=CC(=C1)C)C)=O PTWJOXNRRWDXDI-UHFFFAOYSA-N 0.000 claims 1
- SXSQKDZPGSYAQU-UHFFFAOYSA-N C(C)(C)(C)N(NC(=O)C1=CC2=C(B(N(N=C2)S(=O)(=O)C)O)C=C1)C(C1=CC(=CC(=C1)C)C)=O Chemical compound C(C)(C)(C)N(NC(=O)C1=CC2=C(B(N(N=C2)S(=O)(=O)C)O)C=C1)C(C1=CC(=CC(=C1)C)C)=O SXSQKDZPGSYAQU-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
- HUZYCSJBOBIITK-UHFFFAOYSA-N C(C)(C)(C)N(NC(=O)C=1C=CC2=C(B(N(N=C2)S(=O)(=O)C)O)C=1)C(C1=CC(=CC(=C1)C)C)=O Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC2=C(B(N(N=C2)S(=O)(=O)C)O)C=1)C(C1=CC(=CC(=C1)C)C)=O HUZYCSJBOBIITK-UHFFFAOYSA-N 0.000 claims 1
- PHRTUTCERVJXGD-UHFFFAOYSA-N C(C)(C)(C)N(NC(=O)C=1C=CC2=C(B(NC2)O)C=1)C(C1=CC(=CC(=C1)C)C)=O Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC2=C(B(NC2)O)C=1)C(C1=CC(=CC(=C1)C)C)=O PHRTUTCERVJXGD-UHFFFAOYSA-N 0.000 claims 1
- UBWJUSJRNDKGAS-UHFFFAOYSA-N C(C)(C)(C)N(NC(=O)C=1C=CC2=C(B(NCC2)O)C=1)C(C1=CC(=CC(=C1)C)C)=O Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC2=C(B(NCC2)O)C=1)C(C1=CC(=CC(=C1)C)C)=O UBWJUSJRNDKGAS-UHFFFAOYSA-N 0.000 claims 1
- VFJYITRDCWMXET-UHFFFAOYSA-N C(C)(C)(C)N(NC(=O)C=1C=CC2=C(C=NOB2O)C=1)C(C1=CC(=CC(=C1)C)C)=O Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC2=C(C=NOB2O)C=1)C(C1=CC(=CC(=C1)C)C)=O VFJYITRDCWMXET-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
- MEYUPEIDYKLZIP-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(OC(=N2)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(OC(=N2)C)O)C=C1 MEYUPEIDYKLZIP-UHFFFAOYSA-N 0.000 claims 1
- XTOJRNLRAVOYTG-UHFFFAOYSA-N C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C1=CC2=C(B(OC=N2)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(OC=N2)O)C=C1 XTOJRNLRAVOYTG-UHFFFAOYSA-N 0.000 claims 1
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- JZVYEHTVQNCPQU-HMKMWLAXSA-N C(C=1C=C(C(=O)N(NC(=O)C2=C(C3=C(B(OC3)O)C=C2)F)[C@@H](C(C)(C)C)CC)C=C(C=1)C([2H])([2H])[2H])([2H])([2H])[2H] Chemical compound C(C=1C=C(C(=O)N(NC(=O)C2=C(C3=C(B(OC3)O)C=C2)F)[C@@H](C(C)(C)C)CC)C=C(C=1)C([2H])([2H])[2H])([2H])([2H])[2H] JZVYEHTVQNCPQU-HMKMWLAXSA-N 0.000 claims 1
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- IFULGRSCCDESIS-OAQYLSRUSA-N [3-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylpentan-3-yl]amino]carbamoyl]-6-(ethoxymethyl)-2-fluorophenyl]boronic acid Chemical compound FC1=C(B(O)O)C(COCC)=CC=C1C(=O)NN([C@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 IFULGRSCCDESIS-OAQYLSRUSA-N 0.000 claims 1
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- DIOJQFNOVKNJQV-UHFFFAOYSA-N [3-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-fluorophenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(B(O)O)C=CC=2)F)C(C)(C)C)=C1 DIOJQFNOVKNJQV-UHFFFAOYSA-N 0.000 claims 1
- HVNUAOPRYLSIHD-UHFFFAOYSA-N [3-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-methylphenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(B(O)O)C=CC=2)C)C(C)(C)C)=C1 HVNUAOPRYLSIHD-UHFFFAOYSA-N 0.000 claims 1
- ZNRNNTFHHMFCEF-OAQYLSRUSA-N [3-chloro-4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylhexan-3-yl]amino]carbamoyl]phenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C=C1Cl ZNRNNTFHHMFCEF-OAQYLSRUSA-N 0.000 claims 1
- QMUYEVFHBOOQOY-OAQYLSRUSA-N [4-[[(3,5-dimethylbenzoyl)-[(3R)-2,2-dimethylpentan-3-yl]amino]carbamoyl]-2-formylphenyl]boronic acid Chemical compound CC=1C=C(C(=O)N(NC(=O)C2=CC(=C(C=C2)B(O)O)C=O)[C@@H](C(C)(C)C)CC)C=C(C=1)C QMUYEVFHBOOQOY-OAQYLSRUSA-N 0.000 claims 1
- CJTNYMYSWGLRQT-OAQYLSRUSA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylhexan-3-yl]amino]carbamoyl]-2-fluorophenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C(F)=C1 CJTNYMYSWGLRQT-OAQYLSRUSA-N 0.000 claims 1
- CLQLCJMMPYZWNI-HXUWFJFHSA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylhexan-3-yl]amino]carbamoyl]-3,5-difluorophenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C1=C(F)C=C(B(O)O)C=C1F CLQLCJMMPYZWNI-HXUWFJFHSA-N 0.000 claims 1
- LDLDRVMOPUIQJL-OAQYLSRUSA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylhexan-3-yl]amino]carbamoyl]-3-fluorophenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C=C1F LDLDRVMOPUIQJL-OAQYLSRUSA-N 0.000 claims 1
- LPVWRYRWCQFKBS-XMMPIXPASA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylhexan-3-yl]amino]carbamoyl]-3-propan-2-ylphenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C=C1C(C)C LPVWRYRWCQFKBS-XMMPIXPASA-N 0.000 claims 1
- RBPFPADMSVTPRI-OAQYLSRUSA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylhexan-3-yl]amino]carbamoyl]phenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CCC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C=C1 RBPFPADMSVTPRI-OAQYLSRUSA-N 0.000 claims 1
- DSEWJCWXXUFUMX-HSZRJFAPSA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylpentan-3-yl]amino]carbamoyl]-2-(2-methoxyethoxy)-3-methylphenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C(OCCOC)=C1C DSEWJCWXXUFUMX-HSZRJFAPSA-N 0.000 claims 1
- LGBXGSXOOFCCQA-HXUWFJFHSA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylpentan-3-yl]amino]carbamoyl]-2-hydroxy-3-methylphenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C(O)=C1C LGBXGSXOOFCCQA-HXUWFJFHSA-N 0.000 claims 1
- DHFWUILSJZRHHW-HXUWFJFHSA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-2,2-dimethylpentan-3-yl]amino]carbamoyl]-3-fluorophenyl]boronic acid Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C=C1F DHFWUILSJZRHHW-HXUWFJFHSA-N 0.000 claims 1
- JPAZLADGEVSXIQ-OAQYLSRUSA-N [4-[[(3,5-dimethylbenzoyl)-[(3r)-6-fluoro-2,2-dimethylhexan-3-yl]amino]carbamoyl]-3-fluorophenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=CC(=CC=2)B(O)O)F)[C@H](CCCF)C(C)(C)C)=C1 JPAZLADGEVSXIQ-OAQYLSRUSA-N 0.000 claims 1
- GMZNGBLASOTVKV-LJQANCHMSA-N [4-[[[(3r)-2,2-dimethylpentan-3-yl]-(2,6-dimethylpyridine-4-carbonyl)amino]carbamoyl]-3-fluorophenyl]boronic acid Chemical compound C=1C(C)=NC(C)=CC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C=C1F GMZNGBLASOTVKV-LJQANCHMSA-N 0.000 claims 1
- HBBFBSQAXSTEKW-QGZVFWFLSA-N [4-[[[(3r)-2,2-dimethylpentan-3-yl]-(4,6-dimethylpyrimidine-2-carbonyl)amino]carbamoyl]-3-fluorophenyl]boronic acid Chemical compound N=1C(C)=CC(C)=NC=1C(=O)N([C@H](CC)C(C)(C)C)NC(=O)C1=CC=C(B(O)O)C=C1F HBBFBSQAXSTEKW-QGZVFWFLSA-N 0.000 claims 1
- DHFWUILSJZRHHW-HMKMWLAXSA-N [4-[[[3,5-bis(trideuteriomethyl)benzoyl]-[(3r)-2,2-dimethylpentan-3-yl]amino]carbamoyl]-3-fluorophenyl]boronic acid Chemical compound [2H]C([2H])([2H])C1=CC(C([2H])([2H])[2H])=CC(C(=O)N(NC(=O)C=2C(=CC(=CC=2)B(O)O)F)[C@H](CC)C(C)(C)C)=C1 DHFWUILSJZRHHW-HMKMWLAXSA-N 0.000 claims 1
- OZLLKUWRTIADPJ-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-(cyanomethylamino)phenyl]boronic acid Chemical compound C(C)(C)(C)N(NC(=O)C1=CC(=C(C=C1)B(O)O)NCC#N)C(C1=CC(=CC(=C1)C)C)=O OZLLKUWRTIADPJ-UHFFFAOYSA-N 0.000 claims 1
- PNMKEWIROOCVJX-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-fluorophenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C=C(F)C(B(O)O)=CC=2)C(C)(C)C)=C1 PNMKEWIROOCVJX-UHFFFAOYSA-N 0.000 claims 1
- DNZVXSZJLLSZIL-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-formylphenyl]boronic acid Chemical compound C(C)(C)(C)N(NC(=O)C1=CC(=C(C=C1)B(O)O)C=O)C(C1=CC(=CC(=C1)C)C)=O DNZVXSZJLLSZIL-UHFFFAOYSA-N 0.000 claims 1
- VGYLRDATBHIVLM-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-3,5-difluorophenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=CC(=CC=2F)B(O)O)F)C(C)(C)C)=C1 VGYLRDATBHIVLM-UHFFFAOYSA-N 0.000 claims 1
- BPRILSKLUGLDLT-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-3-chlorophenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=CC(=CC=2)B(O)O)Cl)C(C)(C)C)=C1 BPRILSKLUGLDLT-UHFFFAOYSA-N 0.000 claims 1
- ZKSPBDOGDSRTDM-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-3-fluorophenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=CC(=CC=2)B(O)O)F)C(C)(C)C)=C1 ZKSPBDOGDSRTDM-UHFFFAOYSA-N 0.000 claims 1
- MCIIDSDBERDWCO-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-3-methylphenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=CC(=CC=2)B(O)O)C)C(C)(C)C)=C1 MCIIDSDBERDWCO-UHFFFAOYSA-N 0.000 claims 1
- LIZRIFQNUMOYPR-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-3-propan-2-ylphenyl]boronic acid Chemical compound CC(C)C1=CC(B(O)O)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 LIZRIFQNUMOYPR-UHFFFAOYSA-N 0.000 claims 1
- UCMQVJFYJNVNFM-UHFFFAOYSA-N [4-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]phenyl]boronic acid Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C=CC(=CC=2)B(O)O)C(C)(C)C)=C1 UCMQVJFYJNVNFM-UHFFFAOYSA-N 0.000 claims 1
- DGSSHUHHZSGTHX-UHFFFAOYSA-N [4-[tert-butyl-[(2-ethyl-3-methoxybenzoyl)amino]carbamoyl]phenyl]boronic acid Chemical compound CCC1=C(OC)C=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC=C(B(O)O)C=C1 DGSSHUHHZSGTHX-UHFFFAOYSA-N 0.000 claims 1
- HCYHGMJULZRBQJ-UHFFFAOYSA-N [5-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-(cyanomethyl)phenyl]boronic acid Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC(=C(C=1)B(O)O)CC#N)C(C1=CC(=CC(=C1)C)C)=O HCYHGMJULZRBQJ-UHFFFAOYSA-N 0.000 claims 1
- AKCUUZJDMDWMNS-UHFFFAOYSA-N [5-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-(methylaminomethyl)phenyl]boronic acid Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC(=C(C=1)B(O)O)CNC)C(C1=CC(=CC(=C1)C)C)=O AKCUUZJDMDWMNS-UHFFFAOYSA-N 0.000 claims 1
- KYEBJQBCQJTQLF-UHFFFAOYSA-N [5-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-[(dimethylamino)methyl]phenyl]boronic acid Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC(=C(C=1)B(O)O)CN(C)C)C(C1=CC(=CC(=C1)C)C)=O KYEBJQBCQJTQLF-UHFFFAOYSA-N 0.000 claims 1
- PPIUUYUPVSSZFH-UHFFFAOYSA-N [5-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-formylphenyl]boronic acid Chemical compound C(C)(C)(C)N(NC(=O)C=1C=CC(=C(C=1)B(O)O)C=O)C(C1=CC(=CC(=C1)C)C)=O PPIUUYUPVSSZFH-UHFFFAOYSA-N 0.000 claims 1
- VBICCGDKHSTCTL-UHFFFAOYSA-N [5-[tert-butyl-[(3-methoxy-2-methylbenzoyl)amino]carbamoyl]-2-formylphenyl]boronic acid Chemical compound C(C)(C)(C)N(NC(C1=C(C(=CC=C1)OC)C)=O)C(=O)C=1C=CC(=C(C=1)B(O)O)C=O VBICCGDKHSTCTL-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RROVGJINZFSKIM-UHFFFAOYSA-N n'-(2,5-dimethoxybenzoyl)-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(OC)=CC=C(OC)C=1C(=O)N(C(CCC)C(C)(C)C)NC(=O)C(C=1C)=CC=CC=1B1OC(C)(C)C(C)(C)O1 RROVGJINZFSKIM-UHFFFAOYSA-N 0.000 claims 1
- XJKCLEWYNBAXCI-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-1-hydroxy-6-methyl-n'-(2-methylbutan-2-yl)-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)CC)C(=O)C1=CC(C)=CC(C)=C1 XJKCLEWYNBAXCI-UHFFFAOYSA-N 0.000 claims 1
- VBXXKTDJTUGOKX-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-1-hydroxy-6-methyl-n'-propan-2-yl-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(=O)C1=CC(C)=CC(C)=C1 VBXXKTDJTUGOKX-UHFFFAOYSA-N 0.000 claims 1
- LPCQIPGHLIQTFL-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(1-fluorobutan-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(CF)CC)C(=O)C1=CC(C)=CC(C)=C1 LPCQIPGHLIQTFL-UHFFFAOYSA-N 0.000 claims 1
- 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
- YCAUJFUTNKNJRC-UHFFFAOYSA-N n'-(3,5-dimethylbenzoyl)-n'-(2,2-dimethylpentan-3-yl)-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound C=1C=C2COB(O)C2=CC=1C(=O)NN(C(CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 YCAUJFUTNKNJRC-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
- YCAUJFUTNKNJRC-OAQYLSRUSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound C=1C=C2COB(O)C2=CC=1C(=O)NN([C@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 YCAUJFUTNKNJRC-OAQYLSRUSA-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
- HHVUIQGIDPPLQW-JOCHJYFZSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-1-hydroxy-6-methyl-3,4-dihydro-2h-5,2,1-benzoxazaborepine-7-carbohydrazide Chemical compound C=1C=C2B(O)NCCOC2=C(C)C=1C(=O)NN([C@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 HHVUIQGIDPPLQW-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
- QPRWTTPHPHSPBH-HHHXNRCGSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-3-(2-methoxyethoxy)-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(=C1OCCOC)C)=CC=C1B1OC(C)(C)C(C)(C)O1 QPRWTTPHPHSPBH-HHHXNRCGSA-N 0.000 claims 1
- JZVYEHTVQNCPQU-HXUWFJFHSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-4-fluoro-1-hydroxy-3h-2,1-benzoxaborole-5-carbohydrazide Chemical compound C=1C=C2B(O)OCC2=C(F)C=1C(=O)NN([C@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 JZVYEHTVQNCPQU-HXUWFJFHSA-N 0.000 claims 1
- NROQTUOIJUPJMV-LJQANCHMSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3r)-2,2-dimethylpentan-3-yl]-7-fluoro-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound C=1C=C2COB(O)C2=C(F)C=1C(=O)NN([C@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 NROQTUOIJUPJMV-LJQANCHMSA-N 0.000 claims 1
- YCAUJFUTNKNJRC-NRFANRHFSA-N n'-(3,5-dimethylbenzoyl)-n'-[(3s)-2,2-dimethylpentan-3-yl]-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound C=1C=C2COB(O)C2=CC=1C(=O)NN([C@@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 YCAUJFUTNKNJRC-NRFANRHFSA-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
- NROQTUOIJUPJMV-IBGZPJMESA-N n'-(3,5-dimethylbenzoyl)-n'-[(3s)-2,2-dimethylpentan-3-yl]-7-fluoro-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound C=1C=C2COB(O)C2=C(F)C=1C(=O)NN([C@@H](CC)C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 NROQTUOIJUPJMV-IBGZPJMESA-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
- NROQTUOIJUPJMV-KGYOEJBGSA-N n'-[3,5-bis(trideuteriomethyl)benzoyl]-n'-[(3s)-2,2-dimethylpentan-3-yl]-7-fluoro-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound [2H]C([2H])([2H])C1=CC(C([2H])([2H])[2H])=CC(C(=O)N(NC(=O)C=2C(=C3B(O)OCC3=CC=2)F)[C@@H](CC)C(C)(C)C)=C1 NROQTUOIJUPJMV-KGYOEJBGSA-N 0.000 claims 1
- SPJKYVIRCJOWOR-WFGJKAKNSA-N n'-[3,5-bis(trideuteriomethyl)benzoyl]-n'-tert-butyl-4-fluoro-1-hydroxy-3h-2,1-benzoxaborole-5-carbohydrazide Chemical compound [2H]C([2H])([2H])C1=CC(C([2H])([2H])[2H])=CC(C(=O)N(NC(=O)C=2C(=C3COB(O)C3=CC=2)F)C(C)(C)C)=C1 SPJKYVIRCJOWOR-WFGJKAKNSA-N 0.000 claims 1
- DPCFZONBWDGAMF-QGZVFWFLSA-N n'-benzoyl-n'-[(3r)-2,2-dimethylpentan-3-yl]-7-fluoro-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound C=1C=C2COB(O)C2=C(F)C=1C(=O)NN([C@H](CC)C(C)(C)C)C(=O)C1=CC=CC=C1 DPCFZONBWDGAMF-QGZVFWFLSA-N 0.000 claims 1
- VODJABHTIISTQJ-IBGZPJMESA-N n'-benzoyl-n'-[(3s)-2,2-dimethylpentan-3-yl]-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound C=1C=C2COB(O)C2=CC=1C(=O)NN([C@@H](CC)C(C)(C)C)C(=O)C1=CC=CC=C1 VODJABHTIISTQJ-IBGZPJMESA-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
- ZFRQFDRGCUOLQC-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C=C3B(O)OCC3=CC=2)C(C)(C)C)=C1 ZFRQFDRGCUOLQC-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
- PBZPINXQPRPPJD-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-1-hydroxy-6-methyl-3,4-dihydro-2h-5,2,1-benzoxazaborepine-7-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3OCCNB(O)C3=CC=2)C)C(C)(C)C)=C1 PBZPINXQPRPPJD-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
- XDXHKGNPZTYVHW-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-2-hydroxy-9-methyl-4,5-dihydro-3h-1,2-benzoxaborepine-8-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3OB(O)CCCC3=CC=2)C)C(C)(C)C)=C1 XDXHKGNPZTYVHW-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
- SPJKYVIRCJOWOR-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-4-fluoro-1-hydroxy-3h-2,1-benzoxaborole-5-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3COB(O)C3=CC=2)F)C(C)(C)C)=C1 SPJKYVIRCJOWOR-UHFFFAOYSA-N 0.000 claims 1
- WLVPPRLTNAOGSQ-UHFFFAOYSA-N n'-tert-butyl-n'-(3,5-dimethylbenzoyl)-7-fluoro-1-hydroxy-3h-2,1-benzoxaborole-6-carbohydrazide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3B(O)OCC3=CC=2)F)C(C)(C)C)=C1 WLVPPRLTNAOGSQ-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
- KTFQMTRNDZGVGN-GOSISDBHSA-N n-[(3r)-2,2-dimethylpentan-3-yl]-n'-(1-hydroxy-3h-2,1-benzoxaborole-6-carbonyl)-4,6-dimethylpyrimidine-2-carbohydrazide Chemical compound C=1C=C2COB(O)C2=CC=1C(=O)NN([C@H](CC)C(C)(C)C)C(=O)C1=NC(C)=CC(C)=N1 KTFQMTRNDZGVGN-GOSISDBHSA-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
- LUEGWYFDTLXXPI-UHFFFAOYSA-N n-tert-butyl-n'-(1-hydroxy-3h-2,1-benzoxaborole-6-carbonyl)-2,6-dimethylpyridine-4-carbohydrazide Chemical compound CC1=NC(C)=CC(C(=O)N(NC(=O)C=2C=C3B(O)OCC3=CC=2)C(C)(C)C)=C1 LUEGWYFDTLXXPI-UHFFFAOYSA-N 0.000 claims 1
- WRVQSFAOTVSMRR-UHFFFAOYSA-N n-tert-butyl-n'-(7-fluoro-1-hydroxy-3h-2,1-benzoxaborole-6-carbonyl)-2,6-dimethylpyridine-4-carbohydrazide Chemical compound CC1=NC(C)=CC(C(=O)N(NC(=O)C=2C(=C3B(O)OCC3=CC=2)F)C(C)(C)C)=C1 WRVQSFAOTVSMRR-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- QOWGBQAQGVMUFP-UHFFFAOYSA-N tert-butyl n-[2-[3-[[tert-butyl-(3,5-dimethylbenzoyl)amino]carbamoyl]-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl]carbamate Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C(OCCNC(=O)OC(C)(C)C)C(B3OC(C)(C)C(C)(C)O3)=CC=2)C)C(C)(C)C)=C1 QOWGBQAQGVMUFP-UHFFFAOYSA-N 0.000 claims 1
- 150000008037 diacylhydrazines Chemical class 0.000 abstract 2
- 238000001415 gene therapy Methods 0.000 abstract 1
- 230000001939 inductive effect Effects 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000002705 metabolomic analysis Methods 0.000 abstract 1
- 230000001431 metabolomic effect Effects 0.000 abstract 1
- 238000007423 screening assay Methods 0.000 abstract 1
- 230000009261 transgenic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/08—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/69—Boron compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
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| US201462051649P | 2014-09-17 | 2014-09-17 | |
| US62/051,649 | 2014-09-17 | ||
| PCT/US2015/050375 WO2016044390A1 (en) | 2014-09-17 | 2015-09-16 | Boron-containing diacylhydrazine compounds |
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| CA2961738A1 true CA2961738A1 (en) | 2016-03-24 |
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| TW (1) | TW201625650A (enExample) |
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| US11039617B2 (en) | 2013-01-30 | 2021-06-22 | Agrofresh Inc. | Large scale methods of uniformly coating packaging surfaces with a volatile antimicrobial to preserve food freshness |
| 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 |
| CN115197261B (zh) * | 2022-07-06 | 2024-05-03 | 重庆医科大学 | 噁二氮杂硼衍生物的合成方法 |
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| JP4955905B2 (ja) | 2001-02-20 | 2012-06-20 | イントレキソン コーポレーション | キメラレチノイドｘ受容体および新規エクジソン受容体−ベースの誘導性遺伝子発現システムにおけるそれらの使用 |
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| CN1161325C (zh) | 2001-03-26 | 2004-08-11 | 江苏省农药研究所 | 作为杀虫剂的二酰基肼类化合物及制备此种化合物的中间体以及它们的制备方法 |
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| EP1436394A4 (en) | 2001-09-26 | 2004-12-29 | Rheo Gene Holdings Inc | CICADA ECDYSON RECEPTOR NUCLEIC ACIDS, POLYPEPTIDES AND THEIR USE |
| US20050228016A1 (en) | 2002-06-13 | 2005-10-13 | Enrique Michelotti | Tetrahydroquinolines for modulating the expression of exogenous genes via an ecdysone receptor complex |
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| US7304161B2 (en) * | 2003-02-10 | 2007-12-04 | Intrexon Corporation | Diaclhydrazine ligands for modulating the expression of exogenous genes in mammalian systems via an ecdysone receptor complex |
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| US7935510B2 (en) | 2004-04-30 | 2011-05-03 | Intrexon Corporation | Mutant receptors and their use in a nuclear receptor-based inducible gene expression system |
| US9034650B2 (en) | 2005-02-02 | 2015-05-19 | Intrexon Corporation | Site-specific serine recombinases and methods of their use |
| RU2490253C2 (ru) | 2007-05-29 | 2013-08-20 | Интрексон Корпорейшн | Хиральные диацилгидразиновые лиганды для модуляции экспрессии экзогенных генов с помощью экдизон-рецепторного комплекса |
| NZ712167A (en) * | 2013-03-15 | 2018-05-25 | Intrexon Corp | Boron-containing diacylhydrazines |
-
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
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2017
- 2017-03-09 IL IL251073A patent/IL251073A0/en unknown
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2018
- 2018-03-08 US US15/915,415 patent/US10570158B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SG11201701944WA (en) | 2017-04-27 |
| CN107406373A (zh) | 2017-11-28 |
| US20180201628A1 (en) | 2018-07-19 |
| US10570158B2 (en) | 2020-02-25 |
| MX2017003403A (es) | 2017-06-19 |
| WO2016044390A1 (en) | 2016-03-24 |
| CN107406373B (zh) | 2020-04-28 |
| IL251073A0 (en) | 2017-04-30 |
| US9944659B2 (en) | 2018-04-17 |
| US20160083403A1 (en) | 2016-03-24 |
| JP6567657B2 (ja) | 2019-08-28 |
| TW201625650A (zh) | 2016-07-16 |
| AU2015317862A1 (en) | 2017-04-06 |
| EP3194359A1 (en) | 2017-07-26 |
| EP3194359B1 (en) | 2020-04-08 |
| EP3194359A4 (en) | 2018-03-21 |
| JP2017535515A (ja) | 2017-11-30 |
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