GB1239449A - - Google Patents
Info
- Publication number
- GB1239449A GB1239449A GB1239449DA GB1239449A GB 1239449 A GB1239449 A GB 1239449A GB 1239449D A GB1239449D A GB 1239449DA GB 1239449 A GB1239449 A GB 1239449A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sugar
- polyphosphoric acid
- sugars
- base
- nucleosides
- 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
- 235000000346 sugar Nutrition 0.000 abstract 6
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 4
- 239000002777 nucleoside Substances 0.000 abstract 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 125000003835 nucleoside group Chemical group 0.000 abstract 2
- -1 phenyl ester Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000008163 sugars Chemical class 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical compound N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930024421 Adenine Natural products 0.000 abstract 1
- 208000007976 Ketosis Diseases 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229960000643 adenine Drugs 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 150000002337 glycosamines Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002386 heptoses Chemical class 0.000 abstract 1
- 150000002402 hexoses Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002584 ketoses Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003833 nucleoside derivatives Chemical class 0.000 abstract 1
- 125000001477 organic nitrogen group Chemical group 0.000 abstract 1
- 150000002972 pentoses Chemical class 0.000 abstract 1
- 230000026731 phosphorylation Effects 0.000 abstract 1
- 238000006366 phosphorylation reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003538 tetroses Chemical class 0.000 abstract 1
- 150000003641 trioses Chemical class 0.000 abstract 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07H19/16—Purine radicals
-
- 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
- C07F9/098—Esters of polyphosphoric acids or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
Abstract
1,239,449. Nucleosides; polyphosphoric acid phenyl esters. FARBWERKE HOECHST A.G. 24 June, 1968 [24 June, 1967], No. 30044/68. Heading C2C. Nucleosides and derivatives thereof are prepared by reacting a sugar, or sugar derivative having a free carbonyl function, with an organic nitrogen base which contains in a ring at least one nitrogen atom carrying a hydrogen atom, in an inert solvent and in the presence of a polyphosphoric acid phenyl ester in which the phenyl group may be substituted by halogen or C 1-3 alkyl groups. Preferred bases are those derived from pyrimidine, purine and 8-aza-purine. Specified sugars include trioses, tetroses, pentoses, hexoses and heptoses and the corresponding ketoses and, as derivatives, desoxy-sugars, acylated amino sugars, monocarboxylic sugar acid esters, etherified sugars and apurinic acids. The reaction is preferably effected under anhydrous conditions at 50-100 C. and a pH of 0À5-3À0 using an excess of the base. The reaction proceeds through phosphorylation of the sugar or base and the product may be isolated by evaporating the inert solvent, dissolving the residue in water, neutralizing the solution, removing the polyphosphoric acid ester by filtration and recovering the nucleoside from solution, e.g. by chromatography or concentration. Examples describe the preparation of α- . and #-9-D-ribofuranosyl-adenine and α- and # - 9 - D - desoxyribofuranosyl - adenine. Polyphosphoric acid phenyl ester is obtained as a complex mixture by :heating P 2 O 5 and triphenyl phosphate at 300 C.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0052795 | 1967-06-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1239449A true GB1239449A (en) | 1971-07-14 |
Family
ID=7105744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1239449D Expired GB1239449A (en) | 1967-06-24 | 1968-06-24 |
Country Status (7)
Country | Link |
---|---|
US (1) | US3541079A (en) |
AT (1) | AT285829B (en) |
BE (1) | BE717054A (en) |
CH (1) | CH491118A (en) |
DE (1) | DE1670884A1 (en) |
FR (1) | FR1569465A (en) |
GB (1) | GB1239449A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3755295A (en) * | 1969-10-24 | 1973-08-28 | Syntex Corp | 1-(2-amino-2-deoxy-{62 -d-ribofuranosyl) pyrimidines and derivatives thereof |
USRE29835E (en) * | 1971-06-01 | 1978-11-14 | Icn Pharmaceuticals | 1,2,4-Triazole nucleosides |
FI60877C (en) * | 1971-08-13 | 1982-04-13 | Politechnika Gdanska | PROTECTION OF THERAPEUTIC ACTIVITIES OF THERAPEUTIC ACTIVITIES WITH A DISPENSABLE POLYENMACROLIDANTIBIOTICS-N-GLYCOSYL DERIVATIVES |
US5602246A (en) * | 1992-11-25 | 1997-02-11 | Schering Aktiengesellschaft | Process for the preparation of fludarabine or fludarabine phosphate from guanosine |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1206907B (en) * | 1961-05-24 | 1965-12-16 | Hoechst Ag | Process for the production of N-glycosides |
-
1967
- 1967-06-24 DE DE19671670884 patent/DE1670884A1/en active Pending
-
1968
- 1968-06-21 AT AT597868A patent/AT285829B/en not_active IP Right Cessation
- 1968-06-21 US US738858A patent/US3541079A/en not_active Expired - Lifetime
- 1968-06-21 CH CH931868A patent/CH491118A/en not_active IP Right Cessation
- 1968-06-24 BE BE717054D patent/BE717054A/xx unknown
- 1968-06-24 GB GB1239449D patent/GB1239449A/en not_active Expired
- 1968-06-24 FR FR1569465D patent/FR1569465A/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH491118A (en) | 1970-05-31 |
FR1569465A (en) | 1969-05-30 |
BE717054A (en) | 1968-12-24 |
US3541079A (en) | 1970-11-17 |
DE1670884A1 (en) | 1971-02-18 |
AT285829B (en) | 1970-11-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PLNP | Patent lapsed through nonpayment of renewal fees |