AU2013339557A1 - New antibacterial compounds and biological applications thereof - Google Patents
New antibacterial compounds and biological applications thereof Download PDFInfo
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- AU2013339557A1 AU2013339557A1 AU2013339557A AU2013339557A AU2013339557A1 AU 2013339557 A1 AU2013339557 A1 AU 2013339557A1 AU 2013339557 A AU2013339557 A AU 2013339557A AU 2013339557 A AU2013339557 A AU 2013339557A AU 2013339557 A1 AU2013339557 A1 AU 2013339557A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 267
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 126
- 229910052739 hydrogen Inorganic materials 0.000 claims description 122
- 239000000203 mixture Substances 0.000 claims description 96
- -1 (3R,4S,5R)-3,4,5-trihydroxy-6-(N-hydroxyformamido) hexyl Chemical group 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 30
- 230000015572 biosynthetic process Effects 0.000 claims description 28
- 230000009466 transformation Effects 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 21
- 150000007513 acids Chemical class 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 150000002923 oximes Chemical class 0.000 claims description 19
- 229910003827 NRaRb Inorganic materials 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 229940079593 drug Drugs 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 241000894006 Bacteria Species 0.000 claims description 14
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 14
- HWTGSIHSDQGXAV-DSYKOEDSSA-N [(3r,4r,5s)-6-[formyl(hydroxy)amino]-3,4,5-trihydroxyhexyl]phosphonic acid Chemical compound OP(=O)(O)CC[C@@H](O)[C@@H](O)[C@@H](O)CN(O)C=O HWTGSIHSDQGXAV-DSYKOEDSSA-N 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
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- 125000000217 alkyl group Chemical group 0.000 claims description 8
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- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 6
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
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- LBJFEFHCTYMJFD-JKUQZMGJSA-N [(2r,3s,4s)-5-[formyl(hydroxy)amino]-2,3,4-trihydroxypentyl] dihydrogen phosphate Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN(O)C=O LBJFEFHCTYMJFD-JKUQZMGJSA-N 0.000 claims description 4
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- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001976 hemiacetal group Chemical group 0.000 claims 1
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical compound C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 claims 1
- 229960003292 rifamycin Drugs 0.000 claims 1
- YVOFSHPIJOYKSH-NLYBMVFSSA-M sodium rifomycin sv Chemical compound [Na+].OC1=C(C(O)=C2C)C3=C([O-])C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O YVOFSHPIJOYKSH-NLYBMVFSSA-M 0.000 claims 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- PFGVNLZDWRZPJW-OPAMFIHVSA-N otamixaban Chemical compound C([C@@H](C(=O)OC)[C@@H](C)NC(=O)C=1C=CC(=CC=1)C=1C=C[N+]([O-])=CC=1)C1=CC=CC(C(N)=N)=C1 PFGVNLZDWRZPJW-OPAMFIHVSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 239000012898 sample dilution Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- OGNAOIGAPPSUMG-UHFFFAOYSA-N spiro[2.2]pentane Chemical compound C1CC11CC1 OGNAOIGAPPSUMG-UHFFFAOYSA-N 0.000 description 1
- FYGUBWKMMCWIKB-UHFFFAOYSA-N spiro[2.3]hexane Chemical compound C1CC11CCC1 FYGUBWKMMCWIKB-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000005991 sulfenylation reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003569 thioglycosides Chemical class 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Emergency Medicine (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12306350.5A EP2725029A1 (en) | 2012-10-29 | 2012-10-29 | New antibacterial compounds and biological applications thereof |
| EP12306350.5 | 2012-10-29 | ||
| PCT/EP2013/072526 WO2014067904A1 (en) | 2012-10-29 | 2013-10-28 | New antibacterial compounds and biological applications thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2013339557A1 true AU2013339557A1 (en) | 2015-04-30 |
Family
ID=47278726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013339557A Abandoned AU2013339557A1 (en) | 2012-10-29 | 2013-10-28 | New antibacterial compounds and biological applications thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9975911B2 (https=) |
| EP (2) | EP2725029A1 (https=) |
| JP (1) | JP6389463B2 (https=) |
| KR (1) | KR20150105300A (https=) |
| CN (1) | CN104936966A (https=) |
| AU (1) | AU2013339557A1 (https=) |
| BR (1) | BR112015009546A2 (https=) |
| CA (1) | CA2889503A1 (https=) |
| CL (1) | CL2015000985A1 (https=) |
| HK (1) | HK1211034A1 (https=) |
| MX (1) | MX2015005498A (https=) |
| RU (1) | RU2015120376A (https=) |
| WO (1) | WO2014067904A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102282155B (zh) | 2008-12-02 | 2017-06-09 | 日本波涛生命科学公司 | 磷原子修饰的核酸的合成方法 |
| RU2612521C2 (ru) | 2009-07-06 | 2017-03-09 | Онтории, Инк. | Новые пролекарства нуклеиновых кислот и способы их применения |
| JP5868324B2 (ja) | 2010-09-24 | 2016-02-24 | 株式会社Wave Life Sciences Japan | 不斉補助基 |
| CN103796657B (zh) | 2011-07-19 | 2017-07-11 | 波涛生命科学有限公司 | 合成官能化核酸的方法 |
| PL2872485T3 (pl) | 2012-07-13 | 2021-05-31 | Wave Life Sciences Ltd. | Asymetryczna grupa pomocnicza |
| BR112016016400A2 (pt) | 2014-01-16 | 2017-10-03 | Wave Life Sciences Ltd | Composições de oligonucleotídeos quiralmente controlados, seu uso, sua composição farmacêutica, e métodos |
| CN108484619A (zh) * | 2018-04-26 | 2018-09-04 | 福建师范大学泉港石化研究院 | 一种罗丹明基Fe3+荧光探针及其制备方法 |
| CN108484620A (zh) * | 2018-04-26 | 2018-09-04 | 福建师范大学泉港石化研究院 | 一种水溶性罗丹明基Cu2+荧光探针及其合成方法 |
| US11905286B2 (en) | 2018-08-09 | 2024-02-20 | Antabio Sas | Diazabicyclooctanones as inhibitors of serine beta-lactamases |
| SG11202101255UA (en) | 2018-08-09 | 2021-03-30 | Antabio Sas | Diazabicyclooctanones as inhibitors of serine beta-lactamases |
| RU2770537C1 (ru) * | 2021-09-15 | 2022-04-18 | федеральное государственное автономное образовательное учреждение высшего образования «Казанский (Приволжский) федеральный университет» (ФГАОУ ВО КФУ) | Фосфорилсодержащие четвертичные соли аммония с высшими алкильными заместителями, обладающие бактерицидной и фунгицидной активностью |
| CN116905145B (zh) * | 2023-08-07 | 2026-03-06 | 安徽恒益智能科技股份有限公司 | 一种抗菌包芯纱线及其制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4206156A (en) * | 1976-07-27 | 1980-06-03 | Fujisawa Pharmaceutical Company, Limited | Hydroxyaminohydrocarbonphosphonic acids |
| GB1580899A (en) | 1976-07-27 | 1980-12-10 | Fujisawa Pharmaceutical Co | Hydroxyaminohydrocarbonphosphonic acid derivatives and production and use thereof |
| JPS5463024A (en) * | 1977-10-27 | 1979-05-21 | Fujisawa Pharmaceut Co Ltd | 3-(n-formyl-n-hydroxyamino)-2(r)-hydroxypropyl-phosphonic acid, its preparation, and its use |
| JPS5562019A (en) * | 1978-09-14 | 1980-05-10 | Fujisawa Pharmaceut Co Ltd | Antibacterial |
| US4693742A (en) | 1983-12-20 | 1987-09-15 | Rohm And Hass Company | Herbicidal hydroxyamino phosphonic acids and derivatives |
| CA1340588C (en) | 1988-06-13 | 1999-06-08 | Balraj Krishan Handa | Amino acid derivatives |
| US6949528B1 (en) | 1998-03-18 | 2005-09-27 | Goddard John G | Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof |
| BR9912062A (pt) * | 1998-07-15 | 2001-04-03 | Hassan Jomaa | Compostos orgânicos fosforosos e seu uso |
| US6911450B1 (en) | 2001-01-29 | 2005-06-28 | Universite De Geneve | Pyrimidine acyclonucleoside derivatives, preparation method and use thereof |
| FR2872158B1 (fr) | 2004-06-28 | 2006-11-03 | Merck Sante Soc Par Actions Si | Nouveaux composes diazeniumdiolates, leur procede de preparation et leur utilisation therapeutique |
| EP1669365A1 (en) | 2004-12-03 | 2006-06-14 | Mutabilis SA | Method for preparing enzymatic substrate analogs as inhibitors of bacterial heptosyl-transferases |
| WO2008033747A2 (en) | 2006-09-11 | 2008-03-20 | Curis, Inc. | Multi-functional small molecules as anti-proliferative agents |
| AU2007301607A1 (en) | 2006-09-25 | 2008-04-03 | Mutabilis Sa | Substituted heterocyclylcarbonylamino-acetic-acid-derivatives as inhibitors of bacterial heptose synthesis, methods for their preparation and biological applications of said inhibitors |
| EP2141164A1 (en) | 2008-07-01 | 2010-01-06 | Mutabilis | New 1,2,4-triazine derivatives and biological applications thereof |
| HRP20150778T1 (hr) * | 2009-01-23 | 2015-08-28 | Euro-Celtique S.A. | Derivati hidroksamske kiseline |
| WO2011045703A2 (en) | 2009-10-13 | 2011-04-21 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| EP2377853A1 (en) | 2010-04-09 | 2011-10-19 | Universite de Rouen | 7,11-Methanocycloocta[b]quinoline derivative as highly functionalizable acetylcholinesterase inhibitors |
| EP2646451A2 (en) | 2010-12-01 | 2013-10-09 | Laboratoire Biodim | Heptose derivatives for use in the treatment of bacterial infections |
| US9593136B2 (en) * | 2011-07-01 | 2017-03-14 | The George Washington University | Compounds for inhibiting 1-deoxy-D-xylulose-5-phosphate reductoisomerase |
-
2012
- 2012-10-29 EP EP12306350.5A patent/EP2725029A1/en not_active Withdrawn
-
2013
- 2013-04-28 BR BR112015009546A patent/BR112015009546A2/pt not_active IP Right Cessation
- 2013-10-28 CA CA2889503A patent/CA2889503A1/en not_active Abandoned
- 2013-10-28 JP JP2015538485A patent/JP6389463B2/ja not_active Expired - Fee Related
- 2013-10-28 AU AU2013339557A patent/AU2013339557A1/en not_active Abandoned
- 2013-10-28 CN CN201380064824.9A patent/CN104936966A/zh active Pending
- 2013-10-28 HK HK15111841.1A patent/HK1211034A1/xx unknown
- 2013-10-28 US US14/438,929 patent/US9975911B2/en active Active - Reinstated
- 2013-10-28 MX MX2015005498A patent/MX2015005498A/es unknown
- 2013-10-28 WO PCT/EP2013/072526 patent/WO2014067904A1/en not_active Ceased
- 2013-10-28 KR KR1020157014444A patent/KR20150105300A/ko not_active Withdrawn
- 2013-10-28 EP EP13783572.4A patent/EP2912043B1/en not_active Not-in-force
- 2013-10-28 RU RU2015120376A patent/RU2015120376A/ru unknown
-
2015
- 2015-04-17 CL CL2015000985A patent/CL2015000985A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014067904A1 (en) | 2014-05-08 |
| EP2912043B1 (en) | 2016-11-30 |
| KR20150105300A (ko) | 2015-09-16 |
| MX2015005498A (es) | 2016-01-08 |
| EP2912043A1 (en) | 2015-09-02 |
| US20150291636A1 (en) | 2015-10-15 |
| HK1211034A1 (en) | 2016-05-13 |
| US9975911B2 (en) | 2018-05-22 |
| JP2015536928A (ja) | 2015-12-24 |
| BR112015009546A2 (pt) | 2017-07-04 |
| RU2015120376A (ru) | 2016-12-20 |
| JP6389463B2 (ja) | 2018-09-12 |
| EP2725029A1 (en) | 2014-04-30 |
| CA2889503A1 (en) | 2014-05-08 |
| CN104936966A (zh) | 2015-09-23 |
| CL2015000985A1 (es) | 2016-05-13 |
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| PC1 | Assignment before grant (sect. 113) |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |