JP2015536928A5 - - Google Patents
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- Publication number
- JP2015536928A5 JP2015536928A5 JP2015538485A JP2015538485A JP2015536928A5 JP 2015536928 A5 JP2015536928 A5 JP 2015536928A5 JP 2015538485 A JP2015538485 A JP 2015538485A JP 2015538485 A JP2015538485 A JP 2015538485A JP 2015536928 A5 JP2015536928 A5 JP 2015536928A5
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- compound represented
- hydroxy
- phosphonic acid
- same
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 description 23
- 239000002253 acid Substances 0.000 description 21
- -1 dihydrogen phosphate ester Chemical class 0.000 description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- KDGKTJGPFXIBEB-UHFFFAOYSA-N n-hydroxyformamide Chemical compound ONC=O KDGKTJGPFXIBEB-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- UPFLIPJVCRVVAT-RDCZQUQVSA-N FC(C[C@H]([C@H]([C@H](CN(O)C=O)O)O)O)P(O)(O)=O Chemical compound FC(C[C@H]([C@H]([C@H](CN(O)C=O)O)O)O)P(O)(O)=O UPFLIPJVCRVVAT-RDCZQUQVSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 2
- JVMARMZNJZXJAD-KESADLGGSA-N CCOP(=O)(CC[C@H]([C@H]([C@@H](CN(C=O)OCC1=CC=CC=C1)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)O Chemical compound CCOP(=O)(CC[C@H]([C@H]([C@@H](CN(C=O)OCC1=CC=CC=C1)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)O JVMARMZNJZXJAD-KESADLGGSA-N 0.000 description 2
- JNDAAKGDFVOUBF-NGJCXOISSA-N FC(C[C@H]([C@H]([C@H](CN(O)C=O)O)O)O)(F)P(O)(O)=O Chemical compound FC(C[C@H]([C@H]([C@H](CN(O)C=O)O)O)O)(F)P(O)(O)=O JNDAAKGDFVOUBF-NGJCXOISSA-N 0.000 description 2
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 2
- 102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 description 2
- 101000805864 Homo sapiens Divergent protein kinase domain 2A Proteins 0.000 description 2
- 101000998623 Homo sapiens NADH-cytochrome b5 reductase 3 Proteins 0.000 description 2
- 101000928408 Homo sapiens Protein diaphanous homolog 2 Proteins 0.000 description 2
- 108010028921 Lipopeptides Proteins 0.000 description 2
- 102100033153 NADH-cytochrome b5 reductase 3 Human genes 0.000 description 2
- DHVGLJLJOOYIPK-RDCZQUQVSA-N O[C@H](CC(O)P(O)(O)=O)[C@@H](O)[C@@H](O)CN(O)C=O Chemical compound O[C@H](CC(O)P(O)(O)=O)[C@@H](O)[C@@H](O)CN(O)C=O DHVGLJLJOOYIPK-RDCZQUQVSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 102100036469 Protein diaphanous homolog 2 Human genes 0.000 description 2
- 229930189077 Rifamycin Natural products 0.000 description 2
- 108010034396 Streptogramins Proteins 0.000 description 2
- VNMFURBRXFDBRC-JKUQZMGJSA-N [(2s,3s,4s)-5-[formyl(hydroxy)amino]-2,3,4-trihydroxypentyl]phosphonic acid Chemical compound O=CN(O)C[C@H](O)[C@H](O)[C@H](O)CP(O)(O)=O VNMFURBRXFDBRC-JKUQZMGJSA-N 0.000 description 2
- OMYWYTPGDNNIDC-KTUCCBJNSA-N [(3r,4r,5s)-6-[formyl(hydroxy)amino]-3,4,5,7-tetrahydroxyheptyl]phosphonic acid Chemical compound O=CN(O)C(CO)[C@H](O)[C@H](O)[C@H](O)CCP(O)(O)=O OMYWYTPGDNNIDC-KTUCCBJNSA-N 0.000 description 2
- 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 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000001775 anti-pathogenic effect Effects 0.000 description 2
- 229940000425 combination drug Drugs 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000015788 innate immune response Effects 0.000 description 2
- 239000003120 macrolide antibiotic agent Substances 0.000 description 2
- 229940041033 macrolides Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 description 2
- 229940081192 rifamycins Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229940041030 streptogramins Drugs 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- RRRIGSKPMKHISG-OUYGKKDFSA-N C(C1=CC=CC=C1)O[C@@H](CN(C=O)OCC1=CC=CC=C1)[C@H](OCC1=CC=CC=C1)[C@H](OCC1=CC=CC=C1)CI Chemical compound C(C1=CC=CC=C1)O[C@@H](CN(C=O)OCC1=CC=CC=C1)[C@H](OCC1=CC=CC=C1)[C@H](OCC1=CC=CC=C1)CI RRRIGSKPMKHISG-OUYGKKDFSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- JJDXDJKPBZIXPI-LURJTMIESA-N C[C@@H](COC1)C1=C Chemical compound C[C@@H](COC1)C1=C JJDXDJKPBZIXPI-LURJTMIESA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
- 238000007014 Michaelis-Becker reaction Methods 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000037815 bloodstream infection Diseases 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 210000000172 cytosol Anatomy 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002386 heptoses Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000009848 hypophosphorylation Effects 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 238000005954 phosphonylation reaction Methods 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2015536928A JP2015536928A (ja) | 2015-12-24 |
| JP2015536928A5 true JP2015536928A5 (https=) | 2016-12-22 |
| JP6389463B2 JP6389463B2 (ja) | 2018-09-12 |
Family
ID=47278726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015538485A Expired - Fee Related JP6389463B2 (ja) | 2012-10-29 | 2013-10-28 | 新規の抗菌性化合物およびその生物医学的用途 |
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 |
|---|---|---|---|---|
| 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
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