JP6058625B2 - オーレオバシジン誘導体および合成方法 - Google Patents
オーレオバシジン誘導体および合成方法 Download PDFInfo
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- JP6058625B2 JP6058625B2 JP2014502638A JP2014502638A JP6058625B2 JP 6058625 B2 JP6058625 B2 JP 6058625B2 JP 2014502638 A JP2014502638 A JP 2014502638A JP 2014502638 A JP2014502638 A JP 2014502638A JP 6058625 B2 JP6058625 B2 JP 6058625B2
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- Prior art keywords
- compound
- formula
- bis
- diboron
- alkyl
- 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.)
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- 238000000034 method Methods 0.000 title claims description 231
- 238000003786 synthesis reaction Methods 0.000 title description 13
- 230000015572 biosynthetic process Effects 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 224
- 239000002904 solvent Substances 0.000 claims description 120
- 125000000217 alkyl group Chemical group 0.000 claims description 116
- 239000003153 chemical reaction reagent Substances 0.000 claims description 107
- -1 copper (II) halide Chemical class 0.000 claims description 107
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- 239000003054 catalyst Substances 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 45
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 30
- 230000002140 halogenating effect Effects 0.000 claims description 28
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 claims description 27
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims description 18
- LWXSPDVXDPRQED-UHFFFAOYSA-N [B+3].[B+3].C12(C(CCC(C1(C)C)C2)(C)[O-])[O-].C21(C(CCC(C2(C)C)C1)(C)[O-])[O-] Chemical compound [B+3].[B+3].C12(C(CCC(C1(C)C)C2)(C)[O-])[O-].C21(C(CCC(C2(C)C)C1)(C)[O-])[O-] LWXSPDVXDPRQED-UHFFFAOYSA-N 0.000 claims description 17
- 238000005885 boration reaction Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 13
- 229910021590 Copper(II) bromide Inorganic materials 0.000 claims description 11
- MDNDJMCSXOXBFZ-UHFFFAOYSA-N 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane Chemical compound O1CC(C)(C)COB1B1OCC(C)(C)CO1 MDNDJMCSXOXBFZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- LJOXKUBPSYCAFX-BJDJZHNGSA-N diethyl (4s,5s)-2-[(4s,5s)-4,5-bis(ethoxycarbonyl)-1,3,2-dioxaborolan-2-yl]-1,3,2-dioxaborolane-4,5-dicarboxylate Chemical compound O1[C@H](C(=O)OCC)[C@@H](C(=O)OCC)OB1B1O[C@H](C(=O)OCC)[C@@H](C(=O)OCC)O1 LJOXKUBPSYCAFX-BJDJZHNGSA-N 0.000 claims description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 9
- GDBJZTBFVNVAPH-VGWMRTNUSA-N dipropan-2-yl (4s,5s)-2-[(4s,5s)-4,5-bis(propan-2-yloxycarbonyl)-1,3,2-dioxaborolan-2-yl]-1,3,2-dioxaborolane-4,5-dicarboxylate Chemical compound O1[C@H](C(=O)OC(C)C)[C@@H](C(=O)OC(C)C)OB1B1O[C@H](C(=O)OC(C)C)[C@@H](C(=O)OC(C)C)O1 GDBJZTBFVNVAPH-VGWMRTNUSA-N 0.000 claims description 8
- 230000026045 iodination Effects 0.000 claims description 8
- 238000006192 iodination reaction Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- WYBQOWXCLDXZNR-UHFFFAOYSA-N 2-(1,3,2-benzodioxaborol-2-yl)-1,3,2-benzodioxaborole Chemical compound O1C2=CC=CC=C2OB1B1OC2=CC=CC=C2O1 WYBQOWXCLDXZNR-UHFFFAOYSA-N 0.000 claims description 7
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical group CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims description 7
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims description 7
- GDBJZTBFVNVAPH-KLHDSHLOSA-N dipropan-2-yl (4r,5r)-2-[(4r,5r)-4,5-bis(propan-2-yloxycarbonyl)-1,3,2-dioxaborolan-2-yl]-1,3,2-dioxaborolane-4,5-dicarboxylate Chemical compound O1[C@@H](C(=O)OC(C)C)[C@H](C(=O)OC(C)C)OB1B1O[C@@H](C(=O)OC(C)C)[C@H](C(=O)OC(C)C)O1 GDBJZTBFVNVAPH-KLHDSHLOSA-N 0.000 claims description 7
- 230000031709 bromination Effects 0.000 claims description 6
- 238000005893 bromination reaction Methods 0.000 claims description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 101150003085 Pdcl gene Proteins 0.000 claims description 4
- 229910001882 dioxygen Inorganic materials 0.000 claims description 4
- LANVQSVBEALBNB-BJDJZHNGSA-N (4s,5s)-2-[(4s,5s)-4,5-bis(dimethylcarbamoyl)-1,3,2-dioxaborolan-2-yl]-4-n,4-n,5-n,5-n-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide Chemical compound O1[C@H](C(=O)N(C)C)[C@@H](C(=O)N(C)C)OB1B1O[C@H](C(=O)N(C)C)[C@@H](C(=O)N(C)C)O1 LANVQSVBEALBNB-BJDJZHNGSA-N 0.000 claims description 3
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 claims description 3
- JQJOWILVGOJWJF-UHFFFAOYSA-N 2-[1-[(9h-fluoren-9-ylmethoxycarbonylamino)methyl]cyclohexyl]acetic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)NCC1(CC(=O)O)CCCCC1 JQJOWILVGOJWJF-UHFFFAOYSA-N 0.000 claims description 3
- UWJKMSTUOSZXAI-UHFFFAOYSA-N CC1OBOC1C Chemical compound CC1OBOC1C UWJKMSTUOSZXAI-UHFFFAOYSA-N 0.000 claims description 3
- PDTRBCTYOYMYKK-RFIDALOWSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate;(2r,3r)-2,3-diethyl-2,3-dihydroxybutanedioic acid Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC.CC[C@](O)(C(O)=O)[C@](O)(CC)C(O)=O PDTRBCTYOYMYKK-RFIDALOWSA-N 0.000 claims description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
- 239000000203 mixture Substances 0.000 description 60
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 46
- 125000002723 alicyclic group Chemical group 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 42
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 36
- 229910052723 transition metal Inorganic materials 0.000 description 36
- 150000003624 transition metals Chemical group 0.000 description 36
- 235000019441 ethanol Nutrition 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 125000001424 substituent group Chemical group 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- 239000002798 polar solvent Substances 0.000 description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 19
- 125000003342 alkenyl group Chemical group 0.000 description 19
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 18
- 125000002619 bicyclic group Chemical group 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
- 150000002367 halogens Chemical group 0.000 description 17
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 16
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 16
- 239000003814 drug Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 15
- 239000012454 non-polar solvent Substances 0.000 description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000011261 inert gas Substances 0.000 description 14
- 125000002252 acyl group Chemical group 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 125000003435 aroyl group Chemical group 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 125000004104 aryloxy group Chemical group 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 description 11
- 208000015181 infectious disease Diseases 0.000 description 11
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 10
- 125000004043 oxo group Chemical group O=* 0.000 description 10
- 239000003981 vehicle Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- KVNFSFSYJQTSQI-UHFFFAOYSA-N [Ir+].[Ir+].C1CC=CCCC=C1.C1CC=CCCC=C1 Chemical compound [Ir+].[Ir+].C1CC=CCCC=C1.C1CC=CCCC=C1 KVNFSFSYJQTSQI-UHFFFAOYSA-N 0.000 description 8
- HHDBHSJOAURMII-UHFFFAOYSA-N [Ir].[Ir].C1CC=CCCC=C1 Chemical compound [Ir].[Ir].C1CC=CCCC=C1 HHDBHSJOAURMII-UHFFFAOYSA-N 0.000 description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 8
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 8
- 229910052741 iridium Inorganic materials 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 229910052759 nickel Inorganic materials 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910052702 rhenium Inorganic materials 0.000 description 8
- 229910052703 rhodium Inorganic materials 0.000 description 8
- 229940124597 therapeutic agent Drugs 0.000 description 8
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 7
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000012634 fragment Substances 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- 239000008101 lactose Substances 0.000 description 7
- 229910052724 xenon Inorganic materials 0.000 description 7
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 7
- NWGPLYYBECWONP-UHFFFAOYSA-N (carbamoylamino) hydrogen sulfate Chemical compound NC(=O)NOS(O)(=O)=O NWGPLYYBECWONP-UHFFFAOYSA-N 0.000 description 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 125000002541 furyl group Chemical group 0.000 description 6
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 239000012472 biological sample Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 239000003937 drug carrier Substances 0.000 description 5
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 5
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000006187 pill Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007909 solid dosage form Substances 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- RLMLFADXHJLPSQ-NPPFTVEMSA-N (3s,6s,9s,12s,15s,18s,21s,24r,27s)-3,6-dibenzyl-12,24-bis[(2r)-butan-2-yl]-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo[25.3.0]triacontane-2,5,8,11,14,17,20,23,26-nonon Chemical compound C([C@H]1C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(N(C)[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N(C)[C@H](C(=O)O[C@H](C(=O)N(C)[C@@H](C(C)C)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N1C)[C@H](C)CC)C(C)(C)O)=O)[C@H](C)CC)C1=CC=CC=C1 RLMLFADXHJLPSQ-NPPFTVEMSA-N 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161470750P | 2011-04-01 | 2011-04-01 | |
| US61/470,750 | 2011-04-01 | ||
| US201161535018P | 2011-09-15 | 2011-09-15 | |
| US61/535,018 | 2011-09-15 | ||
| PCT/US2012/030269 WO2012134989A1 (en) | 2011-04-01 | 2012-03-23 | Aureobasidium derivatives and methods of synthesis |
Related Child Applications (1)
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| JP2016122323A Division JP6313369B2 (ja) | 2011-04-01 | 2016-06-21 | オーレオバシジン誘導体および合成方法 |
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| JP2014515741A JP2014515741A (ja) | 2014-07-03 |
| JP2014515741A5 JP2014515741A5 (cg-RX-API-DMAC7.html) | 2015-04-30 |
| JP6058625B2 true JP6058625B2 (ja) | 2017-01-11 |
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| JP2016122323A Expired - Fee Related JP6313369B2 (ja) | 2011-04-01 | 2016-06-21 | オーレオバシジン誘導体および合成方法 |
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| JP2016122323A Expired - Fee Related JP6313369B2 (ja) | 2011-04-01 | 2016-06-21 | オーレオバシジン誘導体および合成方法 |
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|---|---|
| US (1) | US8906848B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2694532B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP6058625B2 (cg-RX-API-DMAC7.html) |
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| PL (1) | PL2694532T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2012134989A1 (cg-RX-API-DMAC7.html) |
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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 |
| TW201735792A (zh) | 2016-03-07 | 2017-10-16 | 農業保鮮股份有限公司 | 使用苯并氧雜硼雜環戊烯化合物和防腐氣體作為作物的抗微生物劑之協同方法 |
| JP2019527709A (ja) * | 2016-08-08 | 2019-10-03 | オーレオジェン バイオサイエンシーズ， インコーポレイテッド | オーレオバシジン誘導体および合成方法 |
| WO2018102345A1 (en) * | 2016-11-30 | 2018-06-07 | Agrobiologics Llc | Use of the antifungal aureobasidin a in agriculture |
| WO2020018888A1 (en) * | 2018-07-20 | 2020-01-23 | The Board Of Regents Of The University Of Oklahoma | Antimicrobial peptides and methods of use |
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| JPH0826071B2 (ja) * | 1989-07-11 | 1996-03-13 | 寶酒造株式会社 | 抗真菌抗生物質ｒ１０６誘導体 |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| JP3480848B2 (ja) * | 1992-06-19 | 2003-12-22 | タカラバイオ株式会社 | 環状ペプチドの合成方法 |
| US5886026A (en) | 1993-07-19 | 1999-03-23 | Angiotech Pharmaceuticals Inc. | Anti-angiogenic compositions and methods of use |
| WO1995018147A1 (en) * | 1993-12-27 | 1995-07-06 | Takara Shuzo Co., Ltd. | Aureobasidins |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
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2012
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- 2012-03-23 WO PCT/US2012/030269 patent/WO2012134989A1/en not_active Ceased
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| ES2866698T3 (es) | 2021-10-19 |
| JP6313369B2 (ja) | 2018-04-18 |
| CA2832041C (en) | 2020-12-01 |
| PL2694532T3 (pl) | 2021-08-23 |
| US8906848B2 (en) | 2014-12-09 |
| WO2012134989A1 (en) | 2012-10-04 |
| EP2694532A1 (en) | 2014-02-12 |
| AU2012237028A1 (en) | 2013-10-31 |
| AU2012237028B2 (en) | 2017-04-06 |
| AU2012237028C1 (en) | 2017-12-07 |
| JP2016196489A (ja) | 2016-11-24 |
| JP2014515741A (ja) | 2014-07-03 |
| EP2694532B1 (en) | 2021-04-21 |
| US20140024578A1 (en) | 2014-01-23 |
| CA2832041A1 (en) | 2012-10-04 |
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