DE2722031A1 - 9-(2-o-acyl-beta-d-arabinofuranosyl)- adenin-verbindungen - Google Patents
9-(2-o-acyl-beta-d-arabinofuranosyl)- adenin-verbindungenInfo
- Publication number
- DE2722031A1 DE2722031A1 DE19772722031 DE2722031A DE2722031A1 DE 2722031 A1 DE2722031 A1 DE 2722031A1 DE 19772722031 DE19772722031 DE 19772722031 DE 2722031 A DE2722031 A DE 2722031A DE 2722031 A1 DE2722031 A1 DE 2722031A1
- Authority
- DE
- Germany
- Prior art keywords
- arabinofuranosyl
- adenine
- acyl
- ing
- compounds
- 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.)
- Withdrawn
Links
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical class N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229960000643 adenine Drugs 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 14
- 229930024421 Adenine Natural products 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 244000063299 Bacillus subtilis Species 0.000 description 4
- 235000014469 Bacillus subtilis Nutrition 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 241000187747 Streptomyces Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- -1 propiotyl Chemical group 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000003443 antiviral agent Substances 0.000 description 3
- 230000020176 deacylation Effects 0.000 description 3
- 238000005947 deacylation reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 241001529453 unidentified herpesvirus Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000013553 cell monolayer Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- 241000203716 Actinomycetaceae Species 0.000 description 1
- 241000203809 Actinomycetales Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001619326 Cephalosporium Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000187708 Micromonospora Species 0.000 description 1
- 241001134635 Micromonosporaceae Species 0.000 description 1
- 241000186360 Mycobacteriaceae Species 0.000 description 1
- 241000187481 Mycobacterium phlei Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 241001503636 Pseudonocardia petroleophila Species 0.000 description 1
- 241001134661 Saccharopolyspora rectivirgula Species 0.000 description 1
- 241000063122 Streptacidiphilus griseus Species 0.000 description 1
- 241000187438 Streptomyces fradiae Species 0.000 description 1
- 241001494960 Streptomyces griseoflavus Species 0.000 description 1
- 241000946809 Streptomyces prasinus Species 0.000 description 1
- 241000187177 Streptomyces thermovulgaris Species 0.000 description 1
- 241000187176 Streptomyces violaceoruber Species 0.000 description 1
- 241000187191 Streptomyces viridochromogenes Species 0.000 description 1
- 241000204060 Streptomycetaceae Species 0.000 description 1
- 241000203580 Streptosporangiaceae Species 0.000 description 1
- 241000203587 Streptosporangium roseum Species 0.000 description 1
- 241000203770 Thermoactinomyces vulgaris Species 0.000 description 1
- 241001133165 Thermopolyspora Species 0.000 description 1
- OUQFHKYWNKYTTQ-GCDPNZCJSA-N [(2r,3r,4s,5r)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] acetate Chemical compound CC(=O)O[C@H]1[C@H](OC(=O)C)[C@@H](CO)O[C@H]1N1C2=NC=NC(N)=C2N=C1 OUQFHKYWNKYTTQ-GCDPNZCJSA-N 0.000 description 1
- CFMNHZZTRFLVIC-YGSHXTJESA-N [(2r,3r,4s,5r)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-(2-methylpropanoyloxy)oxolan-3-yl] 2-methylpropanoate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](CO)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CFMNHZZTRFLVIC-YGSHXTJESA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- OIRDTQYFTABQOQ-UHFFFAOYSA-N ara-adenosine Natural products Nc1ncnc2n(cnc12)C1OC(CO)C(O)C1O OIRDTQYFTABQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 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
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940055036 mycobacterium phlei Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/38—Nucleosides
- C12P19/40—Nucleosides having a condensed ring system containing a six-membered ring having two nitrogen atoms in the same ring, e.g. purine nucleosides
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/832—Bacillus
- Y10S435/839—Bacillus subtilis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/687,271 US4055718A (en) | 1976-05-17 | 1976-05-17 | 9-(2-O-Acyl-β-D-arabinofuranosyl)-adenine compounds and method for their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2722031A1 true DE2722031A1 (de) | 1977-12-08 |
Family
ID=24759759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772722031 Withdrawn DE2722031A1 (de) | 1976-05-17 | 1977-05-16 | 9-(2-o-acyl-beta-d-arabinofuranosyl)- adenin-verbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4055718A (OSRAM) |
| JP (1) | JPS535199A (OSRAM) |
| BE (1) | BE854699A (OSRAM) |
| CA (1) | CA1073385A (OSRAM) |
| DE (1) | DE2722031A1 (OSRAM) |
| FR (1) | FR2351995A1 (OSRAM) |
| GB (1) | GB1538009A (OSRAM) |
| NL (1) | NL7705406A (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4371613A (en) * | 1977-08-10 | 1983-02-01 | Ajinomoto Company Incorporated | Method for producing purine arabinosides |
| DK149026C (da) * | 1980-06-23 | 1986-07-07 | Univ Minnesota | Analogifremgangsmaade til fremstilling af adeninnucleosidderivater |
| US4338310A (en) * | 1981-01-16 | 1982-07-06 | The Regents Of The University Of Minnesota | Alkoxyalkanoate esters of arabinofuranosyladenine |
| US4942165A (en) * | 1986-02-11 | 1990-07-17 | Advanced Biologics, Inc. | Treatment for Alzheimer's disease |
| US4814339A (en) * | 1986-02-11 | 1989-03-21 | Advanced Biologics, Inc. | Treatment for Alzheimer's disease |
| JPS62196238A (ja) * | 1986-02-21 | 1987-08-29 | J M Seisakusho:Kk | ラベル自動給紙装置 |
| GB8712745D0 (en) * | 1987-05-30 | 1987-07-01 | Wellcome Found | Antiviral compounds |
| DE4418474A1 (de) * | 1994-05-20 | 1995-11-23 | Schering Ag | Verfahren zur Herstellung von Arabinonucleosiden |
| CA2244314A1 (en) * | 1997-07-31 | 1999-01-31 | Sumitomo Chemical Co., Ltd. | Process for producing nucleoside derivatives |
| US20070167353A1 (en) * | 2003-10-24 | 2007-07-19 | John Hilfinger | Prodrug composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3309358A (en) * | 1965-09-20 | 1967-03-14 | Upjohn Co | 7-deazaadenine 2', 5'-and 3', 5'-dinucleoside phosphate and process therefor |
-
1976
- 1976-05-17 US US05/687,271 patent/US4055718A/en not_active Expired - Lifetime
-
1977
- 1977-05-16 JP JP5626677A patent/JPS535199A/ja active Granted
- 1977-05-16 CA CA278,464A patent/CA1073385A/en not_active Expired
- 1977-05-16 DE DE19772722031 patent/DE2722031A1/de not_active Withdrawn
- 1977-05-16 FR FR7714903A patent/FR2351995A1/fr active Granted
- 1977-05-16 NL NL7705406A patent/NL7705406A/xx not_active Application Discontinuation
- 1977-05-16 BE BE177628A patent/BE854699A/xx not_active IP Right Cessation
- 1977-05-16 GB GB20571/77A patent/GB1538009A/en not_active Expired
Non-Patent Citations (2)
| Title |
|---|
| J. Med. Chem. 16, 1973, S. 754-757 * |
| J. Pharm. Sci. 64, 1975, S. 392-396 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS618076B2 (OSRAM) | 1986-03-11 |
| BE854699A (fr) | 1977-09-16 |
| GB1538009A (en) | 1979-01-10 |
| FR2351995A1 (fr) | 1977-12-16 |
| US4055718A (en) | 1977-10-25 |
| JPS535199A (en) | 1978-01-18 |
| CA1073385A (en) | 1980-03-11 |
| FR2351995B1 (OSRAM) | 1981-01-09 |
| NL7705406A (nl) | 1977-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE4004558A1 (de) | 2',3'-didesoxypurinnucleoside und verfahren zu ihrer herstellung | |
| EP0135758B1 (de) | Oliglucosidderivate | |
| DE3887820T2 (de) | Antibiotika, Benanomicine A und B und Dexylosylbenanomicin B, ihre Herstellung und Verwendung. | |
| DE2813021C2 (de) | Antibiotika KA-6606 I, II, III und IV, diese Antibiotika enthaltende Mittel und Verfahren zur Herstellung dieser Verbindungen | |
| DE2722031A1 (de) | 9-(2-o-acyl-beta-d-arabinofuranosyl)- adenin-verbindungen | |
| CH647245A5 (de) | Desoxycytidin-verbindungen, deren herstellung und diese enthaltende pharmazeutische zubereitung. | |
| DE2743654B2 (de) | Anthracyclinglycoside der Gruppe MA 144-, Verfahren zu ihrer Herstellung sowie diese Glycoside enthaltende pharmazeutische Zubereitungen | |
| DE2722032A1 (de) | 9-(3,5-di-o-acyl-beta-d-arabinofuranosyl)-adenin-verbindungen | |
| DE68905644T2 (de) | Antibiotische Substanz mit Antitumorwirkung. | |
| EP0131181A2 (de) | Anthracyclin-Derivate, ein mikrobiologisches Verfahren zu ihrer Herstellung und ihre Verwendung als Cytostatika | |
| DE2722095A1 (de) | 9-(3-0-acyl-beta-d-arabinofuranosyl)- adenin- und 9-(2,3-di-o-acyl-beta-d-arabinofuranosyl)-adenin-verbindungen | |
| EP0019302A1 (de) | Neue tetracyclische Verbindungen, Verfahren zu deren Herstellung, deren Verwendung und pharmazeutische Präparate | |
| DE69114252T2 (de) | Reveromycin-a, herstellung und verwendung als antitumormittel sowie als fungizid. | |
| AT396480B (de) | Verfahren zur herstellung von 9alpha-hydroxy-4-androsten-3,17-dion | |
| DE69816621T2 (de) | Macrolide mit antitumoraktivität | |
| DE2014277C3 (de) | Verfahren zur Herstellung von Acylderivaten des Antibiotikums T-2636 C | |
| DE48660T1 (de) | Antibiotika, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen. | |
| EP0652205A2 (de) | Moenomycin-Abbauprodukte mit hydroxylierter oder oxidierter Lipidseitenkette und Moenomycin-Analoga, ein Verfahren zur Herstellung und die Verwendung dieser Verbindungen | |
| DE3041130C2 (OSRAM) | ||
| DE2722096A1 (de) | 9-(5-0-acyl-beta-d-arabinofuranosyl)- adenin-verbindungen | |
| DE3425357A1 (de) | 1-hydroxy-cytorhodine, ein mikrobiologisches verfahren zu ihrer herstellung und ihre verwendung als cytostatika | |
| US4212941A (en) | Method for the production of 9-(2-O-acyl-β-D-arabinofuranosyl)adenine compounds | |
| DE1470393A1 (de) | 7-D-Ribofuransoyl-7H-pyrrolo[2,3-d]pyrimidin-4-ole und -thiole sowie Verfahren zu ihrer Herstellung | |
| WO1995009244A1 (de) | Verfahren zur herstellung von arabinonukleotiden | |
| DE3031334C2 (de) | Mikrobiologisches Verfahren zur Herstellung von Cholansäurederivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |