GB783306A - Trihalo-1-d-ribofuranosyl-benzimidazole compounds - Google Patents
Trihalo-1-d-ribofuranosyl-benzimidazole compoundsInfo
- Publication number
- GB783306A GB783306A GB9983/55A GB998355A GB783306A GB 783306 A GB783306 A GB 783306A GB 9983/55 A GB9983/55 A GB 9983/55A GB 998355 A GB998355 A GB 998355A GB 783306 A GB783306 A GB 783306A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- acid
- trihalo
- product
- phosphates
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- C07H19/052—Imidazole radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention comprises: (a) 4 : 5 : 6-(5 : 6 : 7)-trihalo - 1 - D - ribofuranosylbenzimidazoles of the general formula: <FORM:0783306/IV (a)/1> wherein each X represents a halogen atom and the halogen atoms may be the same or different (the position (4 or 7) of the third halogen atom has not been ascertained, and the numbering "4 : 5 : 6 - (5 : 6 : 7)" is used to indicate this and to identify the compounds with those obtainable by the process set out in (e) below); (b) triacyl derivatives of the compounds of (a); (c) acid addition salts of the compounds of (a) and (b); (d) phosphate esters (probably 51-phosphates but possibly including (b) triacyl derivatives of the compounds of (a); (c) acid addition salts of the compounds of (a) and (b); (c) acid addition salts of the compounds of (a) and (b); (d) phosphate esters (probably 5-phosphates but possibly including also 21- and 31-phosphates) of the compounds of (a), as obtainable by treating them with a phosphorylating agent (e.g. pyrophosphoric acid or phosphorus oxychloride pretreated with one molar equivalent of water); (e) the preparation of the compounds of (a) and (b) by the following series of steps, or by any part thereof including (iv) or (v) : (i) treating a 1 : 2 : 3 - trihalo - 4 : 5 - dinitrobenzene with a reducing agent to form a 1 : 2 : 3-trihalo-4 : 5-diaminobenzene; (ii) reacting the product of (i) with formic acid and a mineral acid to form a 4 : 5 : 6-trihalobenzimidazole; (iii) converting the product of (ii) to a 1-halomercuri derivative thereof by reaction with a mercuric halide (advantageously in the presence of NaOH, KOH, Ca(OH)2, Na2CO3 or KHCO3 and in solution in water or a lower alkanol); (iv) reacting the product of (iii) with a 1-halo-2 : 3 : 5-triacyl - D - ribofuranose to produce a compound (b); and (v) subjecting this to hydrolysis or alcoholysis (in alkaline or acid medium) to produce a compound (a). An example describes the complete process, starting with 1 : 2 : 3-trichloro-4 : 5-dinitrobenzene and using mossy tin and hydrochloric acid as the reducing agent in (i), hydrochloric acid as the mineral acid in (ii), mercuric chloride (in ethanol in the presence of dilute caustic soda) in (iii), 1-chloro-2 : 3 : 5-triacetyl - D - ribofuranose in dry xylene) in (iv), and methanol saturated with dry NH3 as alcoholysing agent in (v). The final product, 4 : 5 : 6 - (5 : 6 : 7) - trichloro - 1 - D - ribofuranosylbenzimidazole, is converted to its hydrochloride by saturating an ethanolic solution of the base with dry HCl. Lists are given of additional starting materials, intermediates and final products, including tribromo, dichloromonobromo, dibromo-monochloro, triiodo and dichloromonoiodo compounds, and acyl derivatives in which the acyl groups are propionyl, butyryl and benzoyl.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US783306XA | 1954-04-12 | 1954-04-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB783306A true GB783306A (en) | 1957-09-18 |
Family
ID=22143338
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9983/55A Expired GB783306A (en) | 1954-04-12 | 1955-04-05 | Trihalo-1-d-ribofuranosyl-benzimidazole compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB783306A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4296231A (en) | 1979-05-08 | 1981-10-20 | Ciba-Geigy Corporation | Curable epoxide resin mixtures |
EP0556334A1 (en) * | 1990-11-01 | 1993-08-25 | The Regents Of The University Of Michigan | Polysubstituted benzimidazoles as antiviral agents |
-
1955
- 1955-04-05 GB GB9983/55A patent/GB783306A/en not_active Expired
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4296231A (en) | 1979-05-08 | 1981-10-20 | Ciba-Geigy Corporation | Curable epoxide resin mixtures |
EP0556334A1 (en) * | 1990-11-01 | 1993-08-25 | The Regents Of The University Of Michigan | Polysubstituted benzimidazoles as antiviral agents |
EP0556334A4 (en) * | 1990-11-01 | 1995-03-29 | Univ Michigan | Polysubstituted benzimidazoles as antiviral agents |
US5574058A (en) * | 1990-11-01 | 1996-11-12 | The Regents Of The University Of Michigan | Polysubstituted benzimidazoles as antiviral agents |
US5646125A (en) * | 1990-11-01 | 1997-07-08 | The Regents Of The University Of Michigan | Polysubstituted benzimidazoles as antiviral agents |
US5654283A (en) * | 1990-11-01 | 1997-08-05 | The Regents Of The University Of Michigan | Polysubstituted benzimidazoles as antiviral agents |
US5665709A (en) * | 1990-11-01 | 1997-09-09 | The Regents Of The University Of Michigan | Polysubstituted benzimidazole nucleosides as antiviral agents |
US5705490A (en) * | 1990-11-01 | 1998-01-06 | The Regents Of The University Of Michigan | Polysubstituted benzimidazoles as antiviral agents |
US5712255A (en) * | 1990-11-01 | 1998-01-27 | The Regents Of The University Of Michigan | Treatment of herpes infections with polysubstituted benzimidazoles |
US6093698A (en) * | 1990-11-01 | 2000-07-25 | The Regents Of The University Of Michigan | Polysubstituted benzimidazoles as antiviral agents |
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