CA2832041C - Aureobasidin derivatives and methods of synthesis - Google Patents
Aureobasidin derivatives and methods of synthesis Download PDFInfo
- Publication number
- CA2832041C CA2832041C CA2832041A CA2832041A CA2832041C CA 2832041 C CA2832041 C CA 2832041C CA 2832041 A CA2832041 A CA 2832041A CA 2832041 A CA2832041 A CA 2832041A CA 2832041 C CA2832041 C CA 2832041C
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- CA
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- Prior art keywords
- compound
- formula
- bis
- diboron
- alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 132
- 238000003786 synthesis reaction Methods 0.000 title description 9
- 230000015572 biosynthetic process Effects 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 191
- 239000002904 solvent Substances 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- 239000003153 chemical reaction reagent Substances 0.000 claims description 80
- 125000001072 heteroaryl group Chemical group 0.000 claims description 75
- 239000003054 catalyst Substances 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 59
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
- 229910052723 transition metal Inorganic materials 0.000 claims description 26
- 150000003624 transition metals Chemical group 0.000 claims description 26
- 125000002619 bicyclic group Chemical group 0.000 claims description 24
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical group [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims description 24
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 22
- 230000002140 halogenating effect Effects 0.000 claims description 22
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 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 14
- 229910021590 Copper(II) bromide Inorganic materials 0.000 claims description 12
- 230000002083 iodinating effect Effects 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000003981 vehicle Substances 0.000 claims description 10
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical group I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 9
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 claims description 9
- 208000031888 Mycoses Diseases 0.000 claims description 8
- VNEZFUGEQURPEN-VGDIZKAKSA-N bis[(+)-pinanediolato]diboron Chemical compound C([C@H]1OB(O[C@]11C)B2O[C@@]3(C)[C@@H]4C[C@H](C[C@H]3O2)C4(C)C)[C@@H]2C(C)(C)[C@H]1C2 VNEZFUGEQURPEN-VGDIZKAKSA-N 0.000 claims description 8
- 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 7
- 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 7
- 239000002671 adjuvant Substances 0.000 claims description 7
- 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 7
- 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 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 206010017533 Fungal infection Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 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 5
- UEBSWKNVDRJVHN-UHFFFAOYSA-N 4,4,6-trimethyl-2-(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)-1,3,2-dioxaborinane Chemical compound O1C(C)CC(C)(C)OB1B1OC(C)(C)CC(C)O1 UEBSWKNVDRJVHN-UHFFFAOYSA-N 0.000 claims description 5
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 5
- 239000012472 biological sample Substances 0.000 claims description 5
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- LANVQSVBEALBNB-DDHJBXDOSA-N (4r,5r)-2-[(4r,5r)-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-DDHJBXDOSA-N 0.000 claims description 4
- 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 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
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000000523 sample Substances 0.000 claims description 3
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 claims description 2
- 108010029890 phosphatidylinositol-ceramide phosphoinositol transferase Proteins 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 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 1
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims 1
- UWJKMSTUOSZXAI-UHFFFAOYSA-N CC1OBOC1C Chemical compound CC1OBOC1C UWJKMSTUOSZXAI-UHFFFAOYSA-N 0.000 claims 1
- 229910002666 PdCl2 Inorganic materials 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 abstract description 13
- 239000000126 substance Substances 0.000 abstract description 13
- 230000008569 process Effects 0.000 abstract description 5
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- -1 e.g. Chemical class 0.000 description 123
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 101
- 125000003118 aryl group Chemical group 0.000 description 64
- 125000001931 aliphatic group Chemical group 0.000 description 61
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 39
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 37
- 125000001424 substituent group Chemical group 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 125000000753 cycloalkyl group Chemical group 0.000 description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 125000003342 alkenyl group Chemical group 0.000 description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 17
- 125000003368 amide group Chemical group 0.000 description 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 15
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 14
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- 239000004912 1,5-cyclooctadiene Substances 0.000 description 13
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- 125000002252 acyl group Chemical group 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
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- 241001225321 Aspergillus fumigatus Species 0.000 description 12
- 241000222122 Candida albicans Species 0.000 description 12
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- 125000003435 aroyl group Chemical group 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
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- 239000000243 solution Substances 0.000 description 12
- 125000004104 aryloxy group Chemical group 0.000 description 11
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- 125000005553 heteroaryloxy group Chemical group 0.000 description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 11
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 125000004043 oxo group Chemical group O=* 0.000 description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 10
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- 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 9
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
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- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
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- 239000000047 product Substances 0.000 description 8
- NWGPLYYBECWONP-UHFFFAOYSA-N (carbamoylamino) hydrogen sulfate Chemical compound NC(=O)NOS(O)(=O)=O NWGPLYYBECWONP-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 229940095731 candida albicans Drugs 0.000 description 7
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
-
- 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
- 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
-
- 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)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2832041A1 CA2832041A1 (en) | 2012-10-04 |
| CA2832041C true CA2832041C (en) | 2020-12-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2832041A Active CA2832041C (en) | 2011-04-01 | 2012-03-23 | Aureobasidin derivatives and methods of synthesis |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8906848B2 (enExample) |
| EP (1) | EP2694532B1 (enExample) |
| JP (2) | JP6058625B2 (enExample) |
| AU (1) | AU2012237028C1 (enExample) |
| CA (1) | CA2832041C (enExample) |
| ES (1) | ES2866698T3 (enExample) |
| PL (1) | PL2694532T3 (enExample) |
| WO (1) | WO2012134989A1 (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 |
| NZ745681A (en) | 2016-03-07 | 2022-05-27 | Agrofresh Inc | Synergistic methods of using benzoxaborole compounds and preservative gases as an antimicrobial for crops |
| EP3497113A1 (en) * | 2016-08-08 | 2019-06-19 | Aureogen Biosciences, Inc. | Aureobasidium derivatives and methods of synthesis |
| 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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| 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 |
| US5994341A (en) | 1993-07-19 | 1999-11-30 | Angiogenesis Technologies, Inc. | Anti-angiogenic Compositions and methods for the treatment of arthritis |
| EP0687686B1 (en) * | 1993-12-27 | 2000-08-30 | 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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| PL2694532T3 (pl) | 2021-08-23 |
| ES2866698T3 (es) | 2021-10-19 |
| US20140024578A1 (en) | 2014-01-23 |
| AU2012237028A1 (en) | 2013-10-31 |
| AU2012237028C1 (en) | 2017-12-07 |
| JP6058625B2 (ja) | 2017-01-11 |
| JP2016196489A (ja) | 2016-11-24 |
| EP2694532A1 (en) | 2014-02-12 |
| EP2694532B1 (en) | 2021-04-21 |
| US8906848B2 (en) | 2014-12-09 |
| CA2832041A1 (en) | 2012-10-04 |
| AU2012237028B2 (en) | 2017-04-06 |
| JP6313369B2 (ja) | 2018-04-18 |
| JP2014515741A (ja) | 2014-07-03 |
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