ES301738A1 - A procedure for the obtaining of 1-glicosil-5-azacitosinas. (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for the obtaining of 1-glicosil-5-azacitosinas. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES301738A1 ES301738A1 ES0301738A ES301738A ES301738A1 ES 301738 A1 ES301738 A1 ES 301738A1 ES 0301738 A ES0301738 A ES 0301738A ES 301738 A ES301738 A ES 301738A ES 301738 A1 ES301738 A1 ES 301738A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- general formula
- glycosyl
- same
- carbon atoms
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 238000005915 ammonolysis reaction Methods 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003147 glycosyl group Chemical group 0.000 abstract 1
- -1 glycosyl isocyanates Chemical class 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- 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
- C07H19/12—Triazine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
A process for the preparation of 1-glycosyl-5-azacytosines of the general formula I: ** (See formula) ** wherein R 1 represents a glycosyl or peracyl-glycosyl residue and R 2 represents a hydrogen atom or an alkyl group containing 1-4 carbon atoms; in the same formula R3 and R4 (R3 may be the same as or different from R4) represents hydrogen atoms or alkyl groups containing 1-4 carbon atoms, or aralkyl groups, for example, a benzyl group optionally substituted on the benzene ring, The process comprises acting on the esters of the glycosyl isocyanates of the general formula: R1 - N = C = O (II) where R1 is a peracylglycosyl, with O-alkylisoureas of the general formula V, ** (See formula) ** where R 5 represents an alkyl group containing 1-4 carbon atoms, thus forming 1-acylglycosyl-4-alkylisobiurets of the general formula III, ** (See formula) ** where R1 represents a peracylglycosyl residue and R5 represents the same as in formula V; condensing the latter derivatives with orthoesters of aliphatic acids of the general formula VI, R2 - C (OR6) 3 (VI) wherein R2 represents the same as in formula I and R6 represents a methyl or ethyl group, thus forming 1-acylglycosyl-4-alkoxy-2-oxo-1,2-dihydro-1,3,5-triazines of general formula IV , ** (See formula) ** R3 - NH - R4 (VII) where R3 and R4 represent the same as in formula I, thus forming 1-acyl glycosyl 5-azacytosine derivatives; and, finally, subjecting the latter derivatives to an alcoholysis, preferably by the action of methanol in the presence of sodium methoxide or an ammonolysis, preferably with ammonia in ethanol. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS591663 | 1963-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES301738A1 true ES301738A1 (en) | 1965-01-01 |
Family
ID=5405032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0301738A Expired ES301738A1 (en) | 1963-10-29 | 1964-07-06 | A procedure for the obtaining of 1-glicosil-5-azacitosinas. (Machine-translation by Google Translate, not legally binding) |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT251197B (en) |
| BE (1) | BE653741A (en) |
| CH (1) | CH448111A (en) |
| DE (1) | DE1244790B (en) |
| DK (1) | DK125594B (en) |
| ES (1) | ES301738A1 (en) |
| FI (1) | FI46388C (en) |
| FR (1) | FR1430153A (en) |
| GB (1) | GB1046181A (en) |
| IT (1) | IT1051651B (en) |
| NL (1) | NL6403587A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2012888C3 (en) * | 1970-03-14 | 1981-04-02 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Process for the preparation of 5-azapyrimidine nucleosides |
-
1964
- 1964-01-15 DE DEC31878A patent/DE1244790B/en active Pending
- 1964-01-16 FI FI640083A patent/FI46388C/en active
- 1964-01-16 AT AT30064A patent/AT251197B/en active
- 1964-01-22 DK DK31464AA patent/DK125594B/en unknown
- 1964-02-10 CH CH153164A patent/CH448111A/en unknown
- 1964-03-05 GB GB9440/64A patent/GB1046181A/en not_active Expired
- 1964-04-03 NL NL6403587A patent/NL6403587A/xx unknown
- 1964-07-06 ES ES0301738A patent/ES301738A1/en not_active Expired
- 1964-09-30 BE BE653741A patent/BE653741A/xx unknown
- 1964-10-15 FR FR991567A patent/FR1430153A/en not_active Expired
- 1964-10-28 IT IT23138/64A patent/IT1051651B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CH448111A (en) | 1967-12-15 |
| AT251197B (en) | 1966-12-27 |
| GB1046181A (en) | 1966-10-19 |
| BE653741A (en) | 1965-01-18 |
| FI46388B (en) | 1972-11-30 |
| FI46388C (en) | 1973-03-12 |
| IT1051651B (en) | 1981-05-20 |
| DK125594B (en) | 1973-03-12 |
| FR1430153A (en) | 1966-03-04 |
| NL6403587A (en) | 1965-05-03 |
| DE1244790B (en) | 1967-07-20 |
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