CA2570577A1 - Anti-viral uses of borinic acid complexes - Google Patents
Anti-viral uses of borinic acid complexes Download PDFInfo
- Publication number
- CA2570577A1 CA2570577A1 CA002570577A CA2570577A CA2570577A1 CA 2570577 A1 CA2570577 A1 CA 2570577A1 CA 002570577 A CA002570577 A CA 002570577A CA 2570577 A CA2570577 A CA 2570577A CA 2570577 A1 CA2570577 A1 CA 2570577A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- optionally substituted
- aryl
- amino
- substituted
- 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
- 230000000840 anti-viral effect Effects 0.000 title description 32
- UYANAUSDHIFLFQ-UHFFFAOYSA-N borinic acid Chemical class OB UYANAUSDHIFLFQ-UHFFFAOYSA-N 0.000 title description 23
- 238000000034 method Methods 0.000 claims abstract description 78
- 241000700605 Viruses Species 0.000 claims abstract description 30
- 201000010099 disease Diseases 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 156
- -1 carboxy, thioformyl Chemical group 0.000 claims description 138
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000003107 substituted aryl group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000004104 aryloxy group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000005110 aryl thio group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 18
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 12
- 230000003612 virological effect Effects 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000004986 diarylamino group Chemical group 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 11
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 125000004288 oxazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC1([H])* 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 150000004677 hydrates Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- RIFHJAODNHLCBH-UHFFFAOYSA-N methanethione Chemical group S=[CH] RIFHJAODNHLCBH-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 241000710781 Flaviviridae Species 0.000 claims description 4
- 241000711504 Paramyxoviridae Species 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- ZTLSOLUCMQEGEA-UHFFFAOYSA-N bis(3-chloro-4-methylphenyl)boranyl 3-hydroxypyridine-2-carboxylate Chemical compound C1=C(Cl)C(C)=CC=C1B(C=1C=C(Cl)C(C)=CC=1)OC(=O)C1=NC=CC=C1O ZTLSOLUCMQEGEA-UHFFFAOYSA-N 0.000 claims description 4
- AZAHOGJPPSTBBI-UHFFFAOYSA-N bis(3-chlorophenyl)boranyl 6-amino-3-hydroxypyridine-2-carboxylate Chemical compound NC1=CC=C(O)C(C(=O)OB(C=2C=C(Cl)C=CC=2)C=2C=C(Cl)C=CC=2)=N1 AZAHOGJPPSTBBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 241000711573 Coronaviridae Species 0.000 claims description 3
- 241000700739 Hepadnaviridae Species 0.000 claims description 3
- 241000712464 Orthomyxoviridae Species 0.000 claims description 3
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 3
- 241000700586 Herpesviridae Species 0.000 claims description 2
- 241000709664 Picornaviridae Species 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005418 aryl aryl group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- 241000712907 Retroviridae Species 0.000 claims 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract description 13
- 239000003814 drug Substances 0.000 abstract description 12
- 239000003443 antiviral agent Substances 0.000 abstract description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract description 2
- 229940124597 therapeutic agent Drugs 0.000 abstract description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 description 58
- 239000000047 product Substances 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 24
- 239000013078 crystal Substances 0.000 description 23
- 210000004027 cell Anatomy 0.000 description 19
- 239000007787 solid Substances 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 238000003556 assay Methods 0.000 description 13
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 229960003540 oxyquinoline Drugs 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 108060001084 Luciferase Proteins 0.000 description 9
- 239000005089 Luciferase Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- SIRFLBWZSUIYHF-UHFFFAOYSA-N bis(3-chloro-4-methylphenyl)borinic acid Chemical compound C1=C(Cl)C(C)=CC=C1B(O)C1=CC=C(C)C(Cl)=C1 SIRFLBWZSUIYHF-UHFFFAOYSA-N 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 125000003396 thiol group Chemical class [H]S* 0.000 description 8
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 7
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 208000003152 Yellow Fever Diseases 0.000 description 7
- 239000006184 cosolvent Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WZSGDLVODNWIMB-UHFFFAOYSA-N CC(C)OC(B)OC(C)C Chemical compound CC(C)OC(B)OC(C)C WZSGDLVODNWIMB-UHFFFAOYSA-N 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 238000004113 cell culture Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 6
- BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical class OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 5
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 5
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 150000002148 esters Chemical group 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 241000701024 Human betaherpesvirus 5 Species 0.000 description 4
- 241000725303 Human immunodeficiency virus Species 0.000 description 4
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 101710144111 Non-structural protein 3 Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- GYRPPHBSPHLAMX-UHFFFAOYSA-N bis(4-chlorophenyl)borinic acid Chemical compound C=1C=C(Cl)C=CC=1B(O)C1=CC=C(Cl)C=C1 GYRPPHBSPHLAMX-UHFFFAOYSA-N 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 229940093499 ethyl acetate Drugs 0.000 description 4
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- 239000012458 free base Substances 0.000 description 4
- 208000005252 hepatitis A Diseases 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 230000010076 replication Effects 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- 239000012730 sustained-release form Substances 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- DTNXXIMLMCENGE-UHFFFAOYSA-N (4-chlorophenyl)-methylborinic acid Chemical compound CB(O)C1=CC=C(Cl)C=C1 DTNXXIMLMCENGE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241000701085 Human alphaherpesvirus 3 Species 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000004480 active ingredient Substances 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 229910000085 borane Inorganic materials 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
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- 239000008101 lactose Substances 0.000 description 3
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- 229910052744 lithium Inorganic materials 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- 231100000419 toxicity Toxicity 0.000 description 3
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- 238000010626 work up procedure Methods 0.000 description 3
- NDRIHDUNFVPNAJ-UHFFFAOYSA-N (3-chloro-4-methoxyphenyl)-methylborinic acid Chemical compound COC1=CC=C(B(C)O)C=C1Cl NDRIHDUNFVPNAJ-UHFFFAOYSA-N 0.000 description 2
- WZHZXLATFFKPIU-UHFFFAOYSA-N (3-chlorophenyl)-ethynylborinic acid Chemical compound C#CB(O)C1=CC=CC(Cl)=C1 WZHZXLATFFKPIU-UHFFFAOYSA-N 0.000 description 2
- JPFXVIMMDNIBHY-UHFFFAOYSA-N (3-chlorophenyl)-thiophen-3-ylborinic acid Chemical compound C=1C=CC(Cl)=CC=1B(O)C=1C=CSC=1 JPFXVIMMDNIBHY-UHFFFAOYSA-N 0.000 description 2
- KGAMNGNZWVTDEU-UHFFFAOYSA-N (3-cyanophenyl)-(2-fluorophenyl)borinic acid Chemical compound C=1C=CC=C(F)C=1B(O)C1=CC=CC(C#N)=C1 KGAMNGNZWVTDEU-UHFFFAOYSA-N 0.000 description 2
- BSSKBGJCYLLUSX-UHFFFAOYSA-N (4-chlorophenyl)-(3-fluorophenyl)-quinolin-8-yloxyborane Chemical compound FC1=CC=CC(B(OC=2C3=NC=CC=C3C=CC=2)C=2C=CC(Cl)=CC=2)=C1 BSSKBGJCYLLUSX-UHFFFAOYSA-N 0.000 description 2
- OMSBCEUBXFDUST-UHFFFAOYSA-N (4-cyanophenyl)-(3-fluorophenyl)borinic acid Chemical compound C=1C=CC(F)=CC=1B(O)C1=CC=C(C#N)C=C1 OMSBCEUBXFDUST-UHFFFAOYSA-N 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 2
- HWRDRUJHPPAADP-UHFFFAOYSA-N 8-bis(3-chlorophenyl)boranyloxyquinoline-5-carbonitrile Chemical compound ClC1=CC=CC(B(OC=2C3=NC=CC=C3C(C#N)=CC=2)C=2C=C(Cl)C=CC=2)=C1 HWRDRUJHPPAADP-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 108010017384 Blood Proteins Proteins 0.000 description 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- 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
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Organic Chemistry (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Pulmonology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57941904P | 2004-06-14 | 2004-06-14 | |
| US60/579,419 | 2004-06-14 | ||
| PCT/US2005/020978 WO2006085932A2 (en) | 2004-06-14 | 2005-06-14 | Anti-viral uses of borinic acid complexes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2570577A1 true CA2570577A1 (en) | 2006-08-17 |
Family
ID=36623539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002570577A Abandoned CA2570577A1 (en) | 2004-06-14 | 2005-06-14 | Anti-viral uses of borinic acid complexes |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7393856B2 (https=) |
| EP (1) | EP1765360B1 (https=) |
| JP (1) | JP2008502694A (https=) |
| AT (1) | ATE447960T1 (https=) |
| BR (1) | BRPI0512049A (https=) |
| CA (1) | CA2570577A1 (https=) |
| DE (1) | DE602005017626D1 (https=) |
| ES (1) | ES2333244T3 (https=) |
| MX (1) | MXPA06014417A (https=) |
| PT (1) | PT1765360E (https=) |
| TW (1) | TW200612967A (https=) |
| WO (1) | WO2006085932A2 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070179296A1 (en) * | 2005-12-28 | 2007-08-02 | Anacor Pharmaceuticals, Inc. | Process for manufacturing picolinate borinic esters |
| ME02188B (me) | 2006-02-16 | 2016-02-20 | Anacor Pharmaceuticals Inc | Mali molekuli koji sadrže boron kao antiinflamatorni agensi |
| WO2010018836A2 (ja) * | 2008-08-11 | 2010-02-18 | 独立行政法人科学技術振興機構 | ポリグルタミン凝集阻害剤 |
| US8980544B2 (en) | 2012-11-27 | 2015-03-17 | The Penn State Research Foundation | Boronic and borinic acid compounds as inhibitors of sulfenic acid-containing proteins |
| US9585396B2 (en) | 2013-01-30 | 2017-03-07 | Agrofresh Inc. | Volatile applications against pathogens |
| US9138001B2 (en) | 2013-01-30 | 2015-09-22 | Agrofresh Inc. | Use of benzoxaboroles as volatile antimicrobial agents on meats, plants, or plant parts |
| US8669207B1 (en) | 2013-01-30 | 2014-03-11 | Dow Agrosciences, Llc. | Compounds and compositions |
| 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 |
| KR101756785B1 (ko) * | 2015-03-10 | 2017-07-12 | 한국화학연구원 | 4배위 유기 붕소 화합물의 제조방법 |
| WO2017155879A1 (en) | 2016-03-07 | 2017-09-14 | Agrofresh Inc. | Synergistic methods of using benzoxaborole compounds and preservative gases as an antimicrobial for crops |
| US10961261B2 (en) | 2017-03-01 | 2021-03-30 | Anacor Pharmaceuticals, Inc. | Oxaborole analogs and uses thereof |
| TWI794742B (zh) * | 2020-02-18 | 2023-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| EP4204012A1 (en) | 2020-08-31 | 2023-07-05 | Pfizer Inc. | Methods of protecting rna |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001002424A2 (en) | 1999-07-07 | 2001-01-11 | Du Pont Pharmaceuticals Company | Peptide boronic acid inhibitors of hepatitis c virus protease |
| JP2006511613A (ja) * | 2002-12-18 | 2006-04-06 | アナコア ファーマシューティカルズ インコーポレイテッド | ボロン酸複合体を含む抗生物質および使用法 |
-
2005
- 2005-06-14 DE DE602005017626T patent/DE602005017626D1/de not_active Expired - Lifetime
- 2005-06-14 JP JP2007516648A patent/JP2008502694A/ja not_active Withdrawn
- 2005-06-14 MX MXPA06014417A patent/MXPA06014417A/es active IP Right Grant
- 2005-06-14 EP EP05856817A patent/EP1765360B1/en not_active Expired - Lifetime
- 2005-06-14 AT AT05856817T patent/ATE447960T1/de not_active IP Right Cessation
- 2005-06-14 TW TW094119708A patent/TW200612967A/zh unknown
- 2005-06-14 US US11/152,959 patent/US7393856B2/en not_active Expired - Fee Related
- 2005-06-14 BR BRPI0512049-7A patent/BRPI0512049A/pt not_active IP Right Cessation
- 2005-06-14 CA CA002570577A patent/CA2570577A1/en not_active Abandoned
- 2005-06-14 ES ES05856817T patent/ES2333244T3/es not_active Expired - Lifetime
- 2005-06-14 PT PT05856817T patent/PT1765360E/pt unknown
- 2005-06-14 WO PCT/US2005/020978 patent/WO2006085932A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE602005017626D1 (de) | 2009-12-24 |
| ATE447960T1 (de) | 2009-11-15 |
| PT1765360E (pt) | 2009-12-24 |
| EP1765360A2 (en) | 2007-03-28 |
| JP2008502694A (ja) | 2008-01-31 |
| WO2006085932A3 (en) | 2006-10-05 |
| US20060019927A1 (en) | 2006-01-26 |
| EP1765360B1 (en) | 2009-11-11 |
| TW200612967A (en) | 2006-05-01 |
| MXPA06014417A (es) | 2007-03-08 |
| WO2006085932A2 (en) | 2006-08-17 |
| HK1102702A1 (en) | 2007-11-30 |
| ES2333244T3 (es) | 2010-02-18 |
| BRPI0512049A (pt) | 2008-02-06 |
| US7393856B2 (en) | 2008-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |