CS264455B1 - 5,6-dihydro-5-azauridine and process for preparing thereof - Google Patents
5,6-dihydro-5-azauridine and process for preparing thereof Download PDFInfo
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- CS264455B1 CS264455B1 CS876305A CS630587A CS264455B1 CS 264455 B1 CS264455 B1 CS 264455B1 CS 876305 A CS876305 A CS 876305A CS 630587 A CS630587 A CS 630587A CS 264455 B1 CS264455 B1 CS 264455B1
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- azauridine
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- QNFUDJQAVSWKDP-KVTDHHQDSA-N 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazinane-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)NC1 QNFUDJQAVSWKDP-KVTDHHQDSA-N 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- KYEKLQMDNZPEFU-KVTDHHQDSA-N 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazine-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)N=C1 KYEKLQMDNZPEFU-KVTDHHQDSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006136 alcoholysis reaction Methods 0.000 claims description 4
- -1 alkali metal alkoxide Chemical class 0.000 claims description 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000005915 ammonolysis reaction Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- 239000004744 fabric Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YTFXKURWTLWPKK-UHFFFAOYSA-N 1,3,5-triazinane-2,4-dione Chemical compound O=C1NCNC(=O)N1 YTFXKURWTLWPKK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical group C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- RFYOMFHIKWGPEC-RRKCRQDMSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(=O)N(C)CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 RFYOMFHIKWGPEC-RRKCRQDMSA-N 0.000 description 1
- RFYOMFHIKWGPEC-UHFFFAOYSA-N 5,6-Dihydro-5-azathymidine Natural products O=C1NC(=O)N(C)CN1C1OC(CO)C(O)C1 RFYOMFHIKWGPEC-UHFFFAOYSA-N 0.000 description 1
- 240000002900 Arthrospira platensis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- 241000237537 Ensis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OXKSKIDXPKMVTI-MOUTVQLLSA-N [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(2,4-dioxo-1,3,5-triazin-1-yl)oxolan-2-yl]methyl benzoate Chemical compound O=C(OC[C@H]1O[C@H]([C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1)n1cnc(=O)[nH]c1=O)c1ccccc1 OXKSKIDXPKMVTI-MOUTVQLLSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002507 anti-phytoviral effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Řešení se týká nového 5,6-dihydro- -5-azauridinu a způsobu jeho výroby. Látku lze využít ve farmaceutickém průmyslu.The solution concerns the new 5,6-dihydro- -5-azauridine and a method for its production. Fabric can be used in the pharmaceutical industry.
Description
(57) Řešení se týká nového 5,6-dihydro-5-azauridinu a způsobu jeho výroby. Látku lze využít ve farmaceutickém průmyslu.(57) The present invention relates to a novel 5,6-dihydro-5-azauridine and to a process for its preparation. The substance can be used in the pharmaceutical industry.
Vynález se týká 5,6-dihydro-5-azauridinu vzorce IThe invention relates to a 5,6-dihydro-5-azauridine of formula I
OO
HO OH předmětem předloženého vynálezu je také způsob přípravy 5,6-dihydro-5-azauridinu vzorce I, který je novým analogem uridinu.The object of the present invention is also a process for the preparation of 5,6-dihydro-5-azauridine of formula I, which is a new analog of uridine.
5.6- dihydro-5-azauridin vzorce I je novým analogem uridinu, od něhož se dá formálně odvodit záměnou skupiny CH v poloze 5-pyrimidinového jádra isoelektronickým atomem dusíku a následnou adicí vodíku na dvojnou vazbu v poloze 5,6-triazinového kruhu. Dihydronukleosid vzorce I se řadí do skupiny nukleosidů 5,6-dihydro-5-azaur-acilu. Nejvýznamnější látkou z této skupiny je nukleosidové antibiotikum 5,6-dihydro-5-azathymidin (DHAdT), které bylo isolováno z filtrátů kultury S. platensis var. cla. ensis (DeBoer, Bannisters USA pat.The 5,6-dihydro-5-azauridine of formula I is a novel uridine analog from which it can be formally derived by substituting the CH group at the 5-pyrimidine nucleus position with an isoelectronic nitrogen atom and then adding hydrogen to the double bond at the 5,6-triazine ring position. The dihydronucleoside of formula I belongs to the group of nucleosides of 5,6-dihydro-5-azauracil. The most prominent of this group is the nucleoside antibiotic 5,6-dihydro-5-azathymidine (DHAdT), which was isolated from culture filtrates of S. platensis var. customs duties. ensis (DeBoer, Bannisters US Pat.
907 643 (1975)) . a vykazuje účinnost proti DNA virům a gram-negativním bakteriím. Předpokládaným meziproduktem biosyntézy DHAdT je 5'-fosfát-5,6-dihydro-5-azauridinu. Samotný907,643 (1975)). and shows activity against DNA viruses and gram-negative bacteria. A putative intermediate of DHAdT biosynthesis is 5'-phosphate-5,6-dihydro-5-azauridine. Alone
5,6-dihydro-5-azauracil je také známým selektivně působícím antifytovirálním činidlem a jeho předpokládaným aktivním metabolitem je také uvedený 5'-fosfát-5,6-dihydro-5-azauridinu.5,6-Dihydro-5-azauracil is also a known selectively acting antiphytoviral agent and its predicted active metabolite is also said 5'-phosphate-5,6-dihydro-5-azauridine.
Z těchto důvodů lze antivirální, případně antibakteriální účinnost očekávat také u 5,6-dihydro-5-azauridinu vzorce I.For this reason, 5,6-dihydro-5-azauridine of formula I can also be expected to have antiviral or antibacterial activity.
5.6- dihydro-5-azaurid.in vzorce I je na rozdíl od 5-azauridinu stálý ve vodných roztocích v širokém rozmezí pH a je také podstatně lépe rozpustný ve vodě.Unlike 5-azauridine, the 5,6-dihydro-5-azuridine of formula I is stable in aqueous solutions over a wide pH range and is also substantially better soluble in water.
Způsob výroby 5,6-dihydro-5-azauridinu vzorce I spočívá v tom, že se volný nebo blokovaný 5-azauridin obecného vzorce IIA process for the preparation of 5,6-dihydro-5-azauridine of formula I is characterized in that the free or blocked 5-azauridine of formula II
(II) , kde R je vodík nebo acyl, případně kovalentní alkoholát sloučeniny obecného vzorce II, kde R je acyl, redukuje práškovým zinkem v bezvodé karboxylové kyselině s 1 až 4 atomy uhlíku a v případě použití sloučeniny obecného vzorce II, kde R je acyl, se vzniklý 2',3',5'-tri-0-acyl-5,6-dihydro-5-azauridin obecného vzorce III(II) wherein R is hydrogen or acyl, optionally a covalent alcoholate of a compound of formula (II) wherein R is acyl, is reduced by zinc powder in anhydrous C 1 -C 4 carboxylic acid, and when a compound of formula (II) wherein R is acyl , the resulting 2 ', 3', 5'-tri-O-acyl-5,6-dihydro-5-azauridine of formula III
(III),(III),
RO OR kde R je acyl, podrobí alkoholýze nebo amonolýze.RO OR where R is acyl, undergoes alcoholysis or ammonolysis.
Redukce probíhá velmi dobře již při teplotě místnosti za použití pěti až desetinásobku teoretického množství práškového zniku. Jako karboxylové kyselina se osvědčila komerčně dobře dostupná kyselina octová. Redukci méně stabilního blokovaného 5-azauridinu je vhodné provádět ve směsi karboxylové kyseliny a 2,2-dimethoxypropanu, který zaručuje bezvodost reakčního prostředí. Alkoholýza 2',3',5'-tri-O-acyl-5,6-dihydro-5-azauridinu vzorce III se provádí roztokem alkoxidu alkalického kovu v alkanolu s 1 až 4 atomy uhlíku, s výhodou methoxidem sodným v methanolu. Amonolýza sloučenin vzorce III( se provádí roztokem amoniaku v alkanolu s 1 až 4 atomy uhlíku, s výhodou v methanolu.The reduction proceeds very well already at room temperature using five to ten times the theoretical amount of powder recovery. Commercially available acetic acid has proved to be a carboxylic acid. The reduction of the less stable blocked 5-azauridine is preferably carried out in a mixture of carboxylic acid and 2,2-dimethoxypropane, which guarantees the anhydrous nature of the reaction medium. The alcoholysis of the 2 ', 3', 5'-tri-O-acyl-5,6-dihydro-5-azauridine of formula III is carried out with a solution of an alkali metal alkoxide in C 1 -C 4 alkanol, preferably sodium methoxide in methanol. Ammonolysis of compounds of formula III ( is carried out with a solution of ammonia in C 1 -C 4 alkanol, preferably in methanol.
V dalším je vynález blíže objasněn v příkladech provedení, aniž se na tyto jakkoliv omezuje.The invention is further illustrated by the following non-limiting examples.
PřikladlHe did
Příprava 2',3',5'-tri-0-benzoyl-5,6-dihydro-5-azauridinuPreparation of 2 ', 3', 5'-tri-O-benzoyl-5,6-dihydro-5-azauridine
Směs kyseliny octové (5 ml) a 2,2-dimethoxypropanu (2 ml) se ponechá 24 hodiny stát při teplotě místnosti v uzavřené baňce. Pak se přidá postupně práškový zinek (0,65 g) a kovalentní adukt 2', 3', 5'-tri-0-benzoyl-5-azaurid.inu s methanolem (0,590 g; 1 mmol) . Směs se 7 hodin intensivně magneticky míchá při teplotě místnosti a nerozpustný materiál se odsaje přes fritu. Materiál na fritě se promyje postupně kyselinou octovou, methanolem a bohatě směsí chloroform-methanol (9:1). Spojené filtráty se vytřepou vodou a 5% roztokem kyselého uhličitanu sodného. Organická vrstva se po vysušení (MgSO^) odpaří ve vakuu. Krysta žací zbytku ze směsi chlorform-methanol-petrolether se po zpracování matečných louhů a vysušení získaného produktu při 100 °C ve vakuu vodní vývěvy získá celkem 0,515 g (92%)A mixture of acetic acid (5 ml) and 2,2-dimethoxypropane (2 ml) was allowed to stand at room temperature in a sealed flask for 24 hours. Zinc powder (0.65 g) and the covalent adduct of 2 ', 3', 5'-tri-O-benzoyl-5-azauridine with methanol (0.590 g; 1 mmol) were then added sequentially. The mixture was stirred vigorously magnetically at room temperature for 7 hours and the insoluble material was filtered off with suction through a frit. The frit material was washed sequentially with acetic acid, methanol and richly chloroform-methanol (9: 1). The combined filtrates were shaken with water and 5% sodium bicarbonate solution. After drying (MgSO4), the organic layer was evaporated in vacuo. Crystallization residue from chloroform-methanol-petroleum ether yielded a total of 0.515 g (92%) after treatment of the mother liquors and drying of the product obtained at 100 ° C under water pump vacuum.
2',3',5'-tri-0-benzoyl-5,6-dihydro-5-azauridinu; t.t. 219 až 221 °C (rozklad).2 ', 3', 5'-tri-O-benzoyl-5,6-dihydro-5-azauridine; m.p. Mp 219-221 ° C (dec.).
Příklad 2Example 2
Příprava 5,6-dihydro-5-azauridinuPreparation of 5,6-dihydro-5-azauridine
Směs 5-azauridinu (0,245 g; 1 mmol), kyseliny octové (5 ml) a práškového zinku (0,65-g) se 24 hodin magneticky míchá při teplotě místnosti. Nerozpustný podíl se odsaje a promyje postupně kyselinou octovou a bohatě methanolem. Spojené filtráty se odpaří ve vakuu, zbytek se rozpustí ve vodě a roztok nanese na sloupec slabě kyselého katexu (50 ml) v H+ formě, který byl připraven ve vodě. Produkt se vymyje vodou a eluát odpaří ve vakuu. Krystalizací zbytku ze směsi methanol-voda (9:1) se pro zpracování matečných louhů získá celkem 0,210 g (85%) 5,6-dihydro-5-azauridinu; t.t. 189 až 190 °C (rozklad).A mixture of 5-azauridine (0.245 g; 1 mmol), acetic acid (5 mL), and zinc powder (0.65 g) was magnetically stirred at room temperature for 24 hours. The insoluble material is filtered off with suction and washed successively with acetic acid and rich methanol. The combined filtrates were evaporated in vacuo, the residue was dissolved in water and applied to a weakly acidic cation exchange column (50 mL) in H + form, which was prepared in water. The product was washed with water and the eluate evaporated in vacuo. Crystallization of the residue from methanol-water (9: 1) afforded a total of 0.210 g (85%) of 5,6-dihydro-5-azauridine for the mother liquors; mp 189-190 ° C (dec.).
Příklad 3Example 3
Příprava 5,6-dihydro-5-azauridinuPreparation of 5,6-dihydro-5-azauridine
Směs 2',3',5'-fri-0-benzoyl-5,6-dihydro-5-azauridinu (0,560; 1 mmol), methanolu (5 ml) a methanolického lM-NaOCH3 (2 ml) se míchá magneticky v uzavřené baňce po dobu 24 hodin. Výchozí látka zpočátku přechází do roztoku a vzápětí se vytvoří gelovitá sraženina. Po okyselení směsi kyselinou octovou (0,2 ml) se gelovitá sraženina rozpustí a vzápětí se začne vylučovat produkt, který se po 6 hodinách stání při teplotě místnosti odsaje a promyje methanolem. Získá se 0,223 g (90%) 5,6-dihydro-5-azauridinu; t.t. 189 až 190 °C (rozklad).A mixture of 2 ', 3', 5'-trans-O-benzoyl-5,6-dihydro-5-azauridine (0.560; 1 mmol), methanol (5 mL) and methanolic 1M-NaOCH 3 (2 mL) was stirred magnetically. in a sealed flask for 24 hours. The starting material initially goes into solution and then a gel-like precipitate is formed. After acidification of the mixture with acetic acid (0.2 ml), the gel-like precipitate was dissolved and the product immediately began to precipitate. 0.223 g (90%) of 5,6-dihydro-5-azauridine is obtained; mp 189-190 ° C (dec.).
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS876305A CS264455B1 (en) | 1987-08-28 | 1987-08-28 | 5,6-dihydro-5-azauridine and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS876305A CS264455B1 (en) | 1987-08-28 | 1987-08-28 | 5,6-dihydro-5-azauridine and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS630587A1 CS630587A1 (en) | 1988-10-14 |
| CS264455B1 true CS264455B1 (en) | 1989-08-14 |
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ID=5409792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS876305A CS264455B1 (en) | 1987-08-28 | 1987-08-28 | 5,6-dihydro-5-azauridine and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS264455B1 (en) |
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1987
- 1987-08-28 CS CS876305A patent/CS264455B1/en unknown
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| Publication number | Publication date |
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| CS630587A1 (en) | 1988-10-14 |
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