GB982079A - Process for the production of xanthine derivatives - Google Patents
Process for the production of xanthine derivativesInfo
- Publication number
- GB982079A GB982079A GB1669862A GB1669862A GB982079A GB 982079 A GB982079 A GB 982079A GB 1669862 A GB1669862 A GB 1669862A GB 1669862 A GB1669862 A GB 1669862A GB 982079 A GB982079 A GB 982079A
- Authority
- GB
- United Kingdom
- Prior art keywords
- uracil
- general formula
- amino
- heating
- dehydration
- 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
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title abstract 4
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title abstract 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 abstract 8
- 238000010438 heat treatment Methods 0.000 abstract 4
- 229940035893 uracil Drugs 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- -1 carbalkoxy Chemical group 0.000 abstract 3
- 230000018044 dehydration Effects 0.000 abstract 3
- 238000006297 dehydration reaction Methods 0.000 abstract 3
- 230000009935 nitrosation Effects 0.000 abstract 3
- 238000007034 nitrosation reaction Methods 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- KTQDGYGLGKJZPZ-UHFFFAOYSA-N 5-nitroso-1h-pyrimidine-2,4-dione Chemical compound O=NC1=CNC(=O)NC1=O KTQDGYGLGKJZPZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 abstract 1
- 238000005891 transamination reaction Methods 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 150000003738 xylenes Chemical class 0.000 abstract 1
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
- C07D473/04—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
- C07D473/02—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
- C07D473/08—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 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Xanthine derivatives of the general formula <FORM:0982079/C2/1> wherein R1 and R2 represent hydrogen atoms or alkyl radicals and R3 represents a hydrogen atom or an alkyl, aryl, aralkyl, carbalkoxy, hydroxyalkyl or di-alkylaminoalkyl radical, are prepared by dehydrating 4-amino-5-nitrosouracils of the general formula <FORM:0982079/C2/2> The dehydration may be performed by dry heating, usually at 50 DEG to 200 DEG C., the uracil or by heating a solution thereof in an organic solvent, e.g. dimethylformamide, benzene, toluene, xylenes and alcohols. The uracil starting materials may be prepared by: (1) reacting the corresponding 4-chloro-uracils with amine of the general formula H2NCH2R3 and nitrosating the product; or (2) transamination of the corresponding 4-amino-uracils with amine hydrochlorides of the general formula H2NCH2R3.HCl and subsequent nitrosation. When the methylene group a to the 4-amino group in the uracil intermediate of (1) above is activated by the presence of another group in the substituent R3, partial or complete dehydration to xanthines of formula I may occur during the nitrosation step. If the ring closure is incomplete the dehydration may be completed by heating the nitrosation mixture or by isolating the nitrosouracil thereform and heating said uracil alone or in solution. In another embodiment 1-R1-3-R2-4-amino-5-nitroso-uracil are simultaneously transaminated with amine hydrochlorides of the formula given in (2) above and dehydrated to the corresponding xanthine derivatives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1669862A GB982079A (en) | 1962-05-01 | 1962-05-01 | Process for the production of xanthine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1669862A GB982079A (en) | 1962-05-01 | 1962-05-01 | Process for the production of xanthine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB982079A true GB982079A (en) | 1965-02-03 |
Family
ID=10082033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1669862A Expired GB982079A (en) | 1962-05-01 | 1962-05-01 | Process for the production of xanthine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB982079A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039780A1 (en) * | 1980-05-02 | 1981-11-18 | Societe Des Produits Nestle S.A. | Di- or trisubstituted xanthines with neuroleptic activity, process for their preparation and pharmaceutical preparations containing them |
| US4452788A (en) * | 1982-04-21 | 1984-06-05 | Warner-Lambert Company | Substituted 8-phenylxanthines |
| FR2541281A1 (en) * | 1983-02-18 | 1984-08-24 | Univ Johns Hopkins | SUBSTITUTED 8-PHENYLXANTHINES AND COMPOSITIONS THEREOF FOR BLOCKING ADENOSINE RECEPTORS |
| 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 |
| WO1987004435A2 (en) * | 1986-01-21 | 1987-07-30 | Beecham Group P.L.C. | Xanthine compounds |
| US4769377A (en) * | 1983-02-18 | 1988-09-06 | The Johns Hopkins University | Adenosine receptor antagonists |
-
1962
- 1962-05-01 GB GB1669862A patent/GB982079A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP0039780A1 (en) * | 1980-05-02 | 1981-11-18 | Societe Des Produits Nestle S.A. | Di- or trisubstituted xanthines with neuroleptic activity, process for their preparation and pharmaceutical preparations containing them |
| US4452788A (en) * | 1982-04-21 | 1984-06-05 | Warner-Lambert Company | Substituted 8-phenylxanthines |
| FR2541281A1 (en) * | 1983-02-18 | 1984-08-24 | Univ Johns Hopkins | SUBSTITUTED 8-PHENYLXANTHINES AND COMPOSITIONS THEREOF FOR BLOCKING ADENOSINE RECEPTORS |
| GB2135311A (en) * | 1983-02-18 | 1984-08-30 | Univ Johns Hopkins | Novel xanthine-type adenosine receptor antagonists |
| DE3406275A1 (en) * | 1983-02-18 | 1984-09-27 | The Johns Hopkins University, Baltimore, Md. | NEW ADENOSINE RECEPTOR ANTAGONISTS |
| US4593095A (en) * | 1983-02-18 | 1986-06-03 | The Johns Hopkins University | Xanthine derivatives |
| US4769377A (en) * | 1983-02-18 | 1988-09-06 | The Johns Hopkins University | Adenosine receptor antagonists |
| WO1987004435A2 (en) * | 1986-01-21 | 1987-07-30 | Beecham Group P.L.C. | Xanthine compounds |
| WO1987004435A3 (en) * | 1986-01-21 | 1988-03-24 | Beecham Group Plc | Xanthine compounds |
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