GB683523A - The manufacture of purine derivatives - Google Patents
The manufacture of purine derivativesInfo
- Publication number
- GB683523A GB683523A GB2183448A GB2183448A GB683523A GB 683523 A GB683523 A GB 683523A GB 2183448 A GB2183448 A GB 2183448A GB 2183448 A GB2183448 A GB 2183448A GB 683523 A GB683523 A GB 683523A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbethoxy
- yields
- naoh
- amino
- hydrochloride
- 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
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Purine compounds of formula (I) or (II) <FORM:0683523/IV (b)/1> <FORM:0683523/IV (b)/2> are made by reacting compounds of formula (III) or (IV) <FORM:0683523/IV (b)/3> <FORM:0683523/IV (b)/4> with an organic or inorganic basic medium preferably pyridine or an alkali hydroxide. When inorganic bases e.g. alkali hydroxides are used, subsequent acidification is necessary. Compounds (III) and (IV) are made by reacting compounds of formula (V) or (VI) <FORM:0683523/IV (b)/5> <FORM:0683523/IV (b)/6> with an isocyanate, an isothiocyanate, a urea, a thiourea or N-substituted derivative thereof, using, for example, a basic medium such as pyridine. Compounds (V) or (VI) are made by condensing compounds of formula <FORM:0683523/IV (b)/7> <FORM:0683523/IV (b)/8> with an iminoether, a thioiminoether or an amidine such as compounds of formula <FORM:0683523/IV (b)/9> <FORM:0683523/IV (b)/100> <FORM:0683523/IV (b)/111> <FORM:0683523/IV (b)/122> <FORM:0683523/IV (b)/133> In the above formul R1, R2, R3 and R4 may be the same or different and represent H, alkyl, aryl or aralkyl groups which may contain inert substituents, X may be O or S and R is H or preferably hydrocarbon such as ethyl. When R3 is H (i) and (ii) are tautomers and when R1 and R4 are H further tautomers of (i) and (ii) may be obtained. In examples: (1) ethyl aminocyanacetate is refluxed in alcoholic-chloroform solution with formamidine hydrochloride to yield 4-amino-5-carbethoxy-iminazole which is refluxed in pyridine with methyl isothiocyanate to give 4-N1-methylthioureido-5-carbethoxy-iminazole which on dissolving in 2N NaOH and acidifying with acetic acid gives 2-thio-1-methylxanthine which may also be made without isolation of the intermediates; (2) ethyl aminocyanacetate refluxed in CHCl3 with thioacetiminobenzyl ether hydrochloride yields 4-amino-5-carbethoxy-2-methyliminazole hydrochloride which is converted by the method of (i) to 4-N1-methyl-thiomido-5-carbethoxy-2-methyliminazole and to 2-thio-1 : 8-dimethylxanthine; (3) 4-amino-5-carbethoxy-2-methyliminazole is refluxed in pyridine with methyl isocyanate, dissolved in hot 10 per cent NaOH after removal of the pyridine, and acidified with acetic acid to give 1 : 8-dimethylxanthine; (4) ethyl aminocyanacetate and thiobenziminobenzyl ether hydrochloride yield 4-amino-5-carbethoxy - 2 - phenyliminazole hydrochloride which with methyl isothiocyanate gives 4-N1-methylthioureido-5-carbethoxy-2-phenyliminazole converted by dissolution in 2N NaOH and acidification to 2 - thio - 8 - phenyl - 1 - methylxanthine; (5) 4-amino-5-carbethoxy-2-phenyliminazole with methylisocyanate yields the corresponding methylureido derivative which on warming with 2N NaOH and acidification yields 1-methyl-8-phenylxanthine; (6) the iminazole of (5) with urea forms 4-ureido-5-carbethoxy-2-phenyliminazole which on treatment with 5 per cent NaOH at 80 DEG C. and subsequent acidification yields 2 : 6-dihydroxy-8-phenylpurine; (7) 4 - amino - 5 - carbethoxy-1-methyl-2-phenyliminazole is refluxed with urea in pyridine and the solid obtained on pouring into water dissolved in 2N NaOH at 80 DEG C. when on acidification 2 : 4-dihydroxy-9-methyl-8-phenylpurine is obtained; (8) the iminazole of (5) and acetylisothiocyanate yields an acetythioureido compound which is hydrolysed with 2N HCl in ethanol to the thioureidoiminazole which on warming in 2N NaOH and acidifying yields 2 - thio - 8 - phenylxanthine; (9) ethyl aminocyanacetate with phenylacetiminoethylthioether hydrochloride yields 4-amino-5-carbethoxy-2-benzyliminazole hydrochloride which with phenylisocyanate gives 4 - N1 - phenylureido - 5 - carbethoxy - 2 - benzyliminazole converted to 8-benzyl-1-phenyl-xanthine on boiling in 2N NaOH and acidifying; (10) 4-amino-5-carbethoxy-2-benzyliminazole with phenylisothiocyanate yields a phenylthioureido compound which with 2N NaOH at 90 DEG C. and acidification yields 2-thio-1-phenyl-8-benzylxanthine; (11) the same benzyliminazole is methylated either with diazomethane in methanol or dimethyl sulphate and refluxed with pyridine and methyl isothiocyanate to give a methylthioureido compound which is converted to 2-thio-1 : 7-dimethyl-8-benzylxanthine; (12) the iminazole of (5) is methylated with ethanol diazomethane to the 2-phenyl-1-methyliminazole which is converted to 4-N1-methylthioureido-5-carbethoxy-2-phenyl-1-methyl-imina zole and then to 2-thio-8-phenyl-1 : 7-dimethylxanthine as in (1); (13) ethyl aminocyanacetate with p - nitrophenylacetiminobenzylthioether hydrochloride gives 4-amino-5-carbethoxy-2-(p1-nitrobenzyl)-iminazole hydrochloride which with methylisocyanate yields 4-N1-methylureido-5-carbethoxy-2-(p1-nitrobenzyl) -iminazole converted to 8-(p1-nitrobenzyl)-1-methylxantine on boiling with 5 per cent NaOH and acidifying. Specifications 683,593 and 683,594 are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2183448A GB683523A (en) | 1948-08-18 | 1948-08-18 | The manufacture of purine derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2183448A GB683523A (en) | 1948-08-18 | 1948-08-18 | The manufacture of purine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB683523A true GB683523A (en) | 1952-12-03 |
Family
ID=10169590
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2183448A Expired GB683523A (en) | 1948-08-18 | 1948-08-18 | The manufacture of purine derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB683523A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4325956A (en) | 1978-10-20 | 1982-04-20 | Aktiebolaget Draco | Method and pharmaceutical preparation for treating chronic obstructive airway disease and cardiac disease, and intermediates for the preparation of therapeutically active xanthine derivatives |
US4338319A (en) | 1979-11-27 | 1982-07-06 | Aktiebolaget Draco | Method for the treatment of chronic obstructive airway or cardiac diseases |
US4548818A (en) * | 1978-10-20 | 1985-10-22 | Kjellin Per G | Composition and methods for the treatment of chronic obstructive airway disease and cardiac disease using 3-alkylxanthines |
WO2010103547A3 (en) * | 2009-03-13 | 2010-12-02 | Advinus Therapeutics Private Limited | Substituted fused pyrimidine compounds |
-
1948
- 1948-08-18 GB GB2183448A patent/GB683523A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4325956A (en) | 1978-10-20 | 1982-04-20 | Aktiebolaget Draco | Method and pharmaceutical preparation for treating chronic obstructive airway disease and cardiac disease, and intermediates for the preparation of therapeutically active xanthine derivatives |
US4548818A (en) * | 1978-10-20 | 1985-10-22 | Kjellin Per G | Composition and methods for the treatment of chronic obstructive airway disease and cardiac disease using 3-alkylxanthines |
US4644001A (en) * | 1978-10-20 | 1987-02-17 | Aktiebolaget Draco | 3-Alkylxanthines, composition and methods for the treatment of chronic obstructive-airway disease and cardiac disease |
US4338319A (en) | 1979-11-27 | 1982-07-06 | Aktiebolaget Draco | Method for the treatment of chronic obstructive airway or cardiac diseases |
WO2010103547A3 (en) * | 2009-03-13 | 2010-12-02 | Advinus Therapeutics Private Limited | Substituted fused pyrimidine compounds |
AU2010222289B2 (en) * | 2009-03-13 | 2013-07-11 | Advinus Therapeutics Private Limited | Substituted fused pyrimidine compounds |
US8859566B2 (en) | 2009-03-13 | 2014-10-14 | Advinus Therapeutics Private Limited | Substituted fused pyrimidine compounds |
US9284316B2 (en) | 2009-03-13 | 2016-03-15 | Advinus Therapeutics Private Limited | Substituted fused pyrimidine compounds |
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