JP2008502696A - ホウ素含有化合物およびその使用方法 - Google Patents
ホウ素含有化合物およびその使用方法 Download PDFInfo
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- JP2008502696A JP2008502696A JP2007516688A JP2007516688A JP2008502696A JP 2008502696 A JP2008502696 A JP 2008502696A JP 2007516688 A JP2007516688 A JP 2007516688A JP 2007516688 A JP2007516688 A JP 2007516688A JP 2008502696 A JP2008502696 A JP 2008502696A
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- JP
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- Prior art keywords
- alkyl
- substituted
- aryl
- optionally substituted
- acid
- 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 abstract description 94
- 150000001875 compounds Chemical class 0.000 title claims description 151
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title description 9
- 229910052796 boron Inorganic materials 0.000 title description 9
- 208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 19
- 206010000496 acne Diseases 0.000 claims abstract description 19
- 241001465754 Metazoa Species 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 174
- -1 2- (morpholino) ethoxy Chemical group 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000003107 substituted aryl group Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000004104 aryloxy group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 102000004127 Cytokines Human genes 0.000 claims description 13
- 108090000695 Cytokines Proteins 0.000 claims description 13
- 230000002401 inhibitory effect Effects 0.000 claims description 13
- 125000004288 oxazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC1([H])* 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 201000004700 rosacea Diseases 0.000 claims description 11
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 230000000770 proinflammatory effect Effects 0.000 claims description 8
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 201000008937 atopic dermatitis Diseases 0.000 claims description 7
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims description 6
- 241001303601 Rosacea Species 0.000 claims description 6
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 201000004624 Dermatitis Diseases 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
- 208000028169 periodontal disease Diseases 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- UYANAUSDHIFLFQ-UHFFFAOYSA-N borinic acid Chemical class OB UYANAUSDHIFLFQ-UHFFFAOYSA-N 0.000 abstract description 19
- 239000000203 mixture Substances 0.000 abstract description 13
- 238000011282 treatment Methods 0.000 abstract description 10
- 239000003242 anti bacterial agent Substances 0.000 abstract description 8
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- 229940088710 antibiotic agent Drugs 0.000 abstract description 6
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract description 4
- 241000282412 Homo Species 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 44
- 239000000047 product Substances 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- 239000007787 solid Substances 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical compound OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 22
- 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 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 230000004054 inflammatory process Effects 0.000 description 18
- 206010061218 Inflammation Diseases 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 125000005110 aryl thio group Chemical group 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 239000008194 pharmaceutical composition Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 102000004889 Interleukin-6 Human genes 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 229940100601 interleukin-6 Drugs 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 210000003491 skin Anatomy 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 239000006184 cosolvent Substances 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 230000002757 inflammatory effect Effects 0.000 description 7
- 125000004001 thioalkyl group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 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 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- BHOFOFKBMGVFSG-UHFFFAOYSA-N methyl-di(propan-2-yloxy)borane Chemical compound CC(C)OB(C)OC(C)C BHOFOFKBMGVFSG-UHFFFAOYSA-N 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
- 230000003000 nontoxic effect Effects 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000005017 substituted alkenyl group Chemical group 0.000 description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
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- 125000005842 heteroatom Chemical group 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 5
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 125000004429 atom Chemical group 0.000 description 4
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- HEMGPARMYBRMGB-UHFFFAOYSA-N bis(3-chlorophenyl)borinic acid Chemical compound C=1C=CC(Cl)=CC=1B(O)C1=CC=CC(Cl)=C1 HEMGPARMYBRMGB-UHFFFAOYSA-N 0.000 description 4
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- GYTWDSRNSHGDKP-UHFFFAOYSA-N B(C1=CC=CC(=C1)Cl)O Chemical compound B(C1=CC=CC(=C1)Cl)O GYTWDSRNSHGDKP-UHFFFAOYSA-N 0.000 description 2
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- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
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- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- 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
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Landscapes
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- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57942104P | 2004-06-14 | 2004-06-14 | |
| PCT/US2005/021165 WO2005123094A2 (en) | 2004-06-14 | 2005-06-14 | Treatment or prevention of skin conditions or tissue conditions in animals using boryloxypyridylmethanones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008502696A true JP2008502696A (ja) | 2008-01-31 |
| JP2008502696A5 JP2008502696A5 (enExample) | 2008-07-31 |
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| JP2007516688A Withdrawn JP2008502696A (ja) | 2004-06-14 | 2005-06-14 | ホウ素含有化合物およびその使用方法 |
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| EP (1) | EP1765358B1 (enExample) |
| JP (1) | JP2008502696A (enExample) |
| KR (1) | KR20070043776A (enExample) |
| CN (1) | CN1972695A (enExample) |
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| AT (1) | ATE499105T1 (enExample) |
| AU (1) | AU2005254095B2 (enExample) |
| BR (1) | BRPI0512054A (enExample) |
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| DE (1) | DE602005026524D1 (enExample) |
| IL (1) | IL179616A0 (enExample) |
| MX (1) | MXPA06014416A (enExample) |
| NZ (1) | NZ551726A (enExample) |
| RU (1) | RU2007101309A (enExample) |
| TW (1) | TW200612966A (enExample) |
| WO (1) | WO2005123094A2 (enExample) |
| ZA (1) | ZA200610353B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010018837A3 (ja) * | 2008-08-11 | 2010-04-15 | 独立行政法人科学技術振興機構 | 蛋白質架橋阻害剤 |
| JP2018511584A (ja) * | 2015-03-10 | 2018-04-26 | コリア リサーチ インスティテュート オブ ケミカル テクノロジー | ４配位有機ホウ素化合物の製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7767657B2 (en) | 2005-02-16 | 2010-08-03 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| ES2872962T3 (es) | 2005-02-16 | 2021-11-03 | Anacor Pharmaceuticals Inc | Boronoftalidas para uso terapéutico |
| MX2007011486A (es) * | 2005-03-24 | 2007-11-20 | Anacor Pharmaceuticals Inc | Formulaciones topicas de antibioticos de acido borinico y sus metodos de uso. |
| EP1965647A2 (en) * | 2005-12-28 | 2008-09-10 | Anacor Pharmaceuticals, Inc. | Process for manufacturing picolinate borinic esters |
| RU2642628C2 (ru) | 2006-02-16 | 2018-01-25 | Анакор Фармасьютикалз, Инк. | Бор-содержащие малые молекулы в качестве противовоспалительных средств |
| BRPI0713010A2 (pt) * | 2006-06-12 | 2012-10-09 | Anacor Pharmaceuticals Inc | compostos para o tratamento de doença periodontal |
| EP3246034A1 (en) | 2008-03-06 | 2017-11-22 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-inflammatory agents |
| WO2010027975A1 (en) | 2008-09-04 | 2010-03-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US8461336B2 (en) | 2008-09-04 | 2013-06-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US9493489B2 (en) * | 2008-10-15 | 2016-11-15 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-protozoal agents |
| TW201110996A (en) | 2009-06-03 | 2011-04-01 | Colgate Palmolive Co | Borinic compositions |
| AP4039A (en) * | 2009-08-14 | 2017-02-28 | Daitao Chen | Boron-containing small molecules as antiprotozoal agents |
| WO2011049971A1 (en) | 2009-10-20 | 2011-04-28 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antiprotozoal agents |
| US8461134B2 (en) | 2009-11-11 | 2013-06-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US8716478B2 (en) | 2010-01-27 | 2014-05-06 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| WO2011116348A1 (en) | 2010-03-19 | 2011-09-22 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-protozoal agent |
| DK2613788T3 (en) | 2010-09-07 | 2017-08-07 | Anacor Pharmaceuticals Inc | BENZOXABOROLD DERIVATIVES FOR TREATMENT OF BACTERIA INFECTIONS |
| US9585396B2 (en) | 2013-01-30 | 2017-03-07 | Agrofresh Inc. | Volatile applications against pathogens |
| US10070649B2 (en) | 2013-01-30 | 2018-09-11 | Agrofresh Inc. | Volatile applications against pathogens |
| US8669207B1 (en) | 2013-01-30 | 2014-03-11 | Dow Agrosciences, Llc. | Compounds and compositions |
| AR094666A1 (es) | 2013-01-30 | 2015-08-19 | Dow Agrosciences Llc | Uso de benzoxaborolas como agentes antimicrobianos volátiles en carnes, plantas o partes de plantas |
| 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 |
| IES86830B2 (en) * | 2015-06-24 | 2017-10-04 | Oriel Seasalt Company Ltd | A super-concentrated seawater mineral extract and uses thereof |
| 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 |
| WO2022043936A1 (en) | 2020-08-31 | 2022-03-03 | Pfizer Inc. | Methods of protecting rna |
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|---|---|---|---|---|
| BE790627A (fr) * | 1971-10-27 | 1973-04-27 | Lilly Co Eli | L'antibiotique a477 et son procede de preparation |
| US5348947A (en) * | 1993-05-07 | 1994-09-20 | American Cyanamid Company | Diarylboron ester and thioester fungicidal agents |
| US6123925A (en) * | 1998-07-27 | 2000-09-26 | Healthshield Technologies L.L.C. | Antibiotic toothpaste |
| US6350786B1 (en) * | 1998-09-22 | 2002-02-26 | Hoffmann-La Roche Inc. | Stable complexes of poorly soluble compounds in ionic polymers |
| EP1233772A4 (en) | 1999-11-19 | 2004-06-16 | Topgene Inc | Boron compounds and complexes as anti-inflammatories |
| MXPA05006685A (es) * | 2002-12-18 | 2005-12-14 | Anacor Pharmaceuticals Inc | Antibioticos que contienen complejos de acido borinico y metodos de uso. |
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2005
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- 2005-06-14 CA CA002570477A patent/CA2570477A1/en not_active Abandoned
- 2005-06-14 CN CNA2005800196020A patent/CN1972695A/zh active Pending
- 2005-06-14 ZA ZA200610353A patent/ZA200610353B/xx unknown
- 2005-06-14 NZ NZ551726A patent/NZ551726A/en unknown
- 2005-06-14 RU RU2007101309/04A patent/RU2007101309A/ru not_active Application Discontinuation
- 2005-06-14 MX MXPA06014416A patent/MXPA06014416A/es active IP Right Grant
- 2005-06-14 KR KR1020077000568A patent/KR20070043776A/ko not_active Ceased
- 2005-06-14 DE DE602005026524T patent/DE602005026524D1/de not_active Expired - Lifetime
- 2005-06-14 BR BRPI0512054-3A patent/BRPI0512054A/pt not_active IP Right Cessation
- 2005-06-14 EP EP05786265A patent/EP1765358B1/en not_active Expired - Lifetime
- 2005-06-14 WO PCT/US2005/021165 patent/WO2005123094A2/en not_active Ceased
- 2005-06-14 AU AU2005254095A patent/AU2005254095B2/en not_active Ceased
- 2005-06-14 JP JP2007516688A patent/JP2008502696A/ja not_active Withdrawn
- 2005-06-14 US US11/153,765 patent/US7652000B2/en not_active Expired - Fee Related
- 2005-06-14 AT AT05786265T patent/ATE499105T1/de not_active IP Right Cessation
- 2005-06-14 TW TW094119690A patent/TW200612966A/zh unknown
-
2006
- 2006-11-27 IL IL179616A patent/IL179616A0/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010018837A3 (ja) * | 2008-08-11 | 2010-04-15 | 独立行政法人科学技術振興機構 | 蛋白質架橋阻害剤 |
| WO2010018836A3 (ja) * | 2008-08-11 | 2010-04-15 | 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 |
| JP5606913B2 (ja) * | 2008-08-11 | 2014-10-15 | 独立行政法人科学技術振興機構 | 蛋白質架橋阻害剤 |
| JP2018511584A (ja) * | 2015-03-10 | 2018-04-26 | コリア リサーチ インスティテュート オブ ケミカル テクノロジー | ４配位有機ホウ素化合物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1765358A2 (en) | 2007-03-28 |
| BRPI0512054A (pt) | 2008-02-06 |
| EP1765358B1 (en) | 2011-02-23 |
| NZ551726A (en) | 2010-09-30 |
| IL179616A0 (en) | 2007-05-15 |
| AR049915A1 (es) | 2006-09-13 |
| US20060009422A1 (en) | 2006-01-12 |
| AU2005254095B2 (en) | 2010-06-03 |
| RU2007101309A (ru) | 2008-07-20 |
| TW200612966A (en) | 2006-05-01 |
| DE602005026524D1 (de) | 2011-04-07 |
| MXPA06014416A (es) | 2007-03-08 |
| WO2005123094A3 (en) | 2006-02-23 |
| CA2570477A1 (en) | 2005-12-29 |
| US7652000B2 (en) | 2010-01-26 |
| ATE499105T1 (de) | 2011-03-15 |
| WO2005123094A2 (en) | 2005-12-29 |
| ZA200610353B (en) | 2010-07-28 |
| AU2005254095A1 (en) | 2005-12-29 |
| KR20070043776A (ko) | 2007-04-25 |
| CN1972695A (zh) | 2007-05-30 |
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