CH654009A5 - Verfahren zur herstellung von allopurinol. - Google Patents
Verfahren zur herstellung von allopurinol. Download PDFInfo
- Publication number
- CH654009A5 CH654009A5 CH151883A CH151883A CH654009A5 CH 654009 A5 CH654009 A5 CH 654009A5 CH 151883 A CH151883 A CH 151883A CH 151883 A CH151883 A CH 151883A CH 654009 A5 CH654009 A5 CH 654009A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrazole
- allopurinol
- formula
- formamide
- ammonia
- Prior art date
Links
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 title claims description 13
- 229960003459 allopurinol Drugs 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 34
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 15
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 238000007363 ring formation reaction Methods 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 2
- 150000003217 pyrazoles Chemical class 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 241000287433 Turdus Species 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000003868 ammonium compounds Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- FGCLOJOLJQDQOG-UHFFFAOYSA-N ethoxymethanediol Chemical compound CCOC(O)O FGCLOJOLJQDQOG-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- YPXGHKWOJXQLQU-UHFFFAOYSA-N ethyl 5-amino-1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1N YPXGHKWOJXQLQU-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH151883A CH654009A5 (de) | 1983-03-21 | 1983-03-21 | Verfahren zur herstellung von allopurinol. |
| DE19833325853 DE3325853A1 (de) | 1983-03-21 | 1983-07-18 | Verfahren zur herstellung von allopurinol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH151883A CH654009A5 (de) | 1983-03-21 | 1983-03-21 | Verfahren zur herstellung von allopurinol. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH654009A5 true CH654009A5 (de) | 1986-01-31 |
Family
ID=4212313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH151883A CH654009A5 (de) | 1983-03-21 | 1983-03-21 | Verfahren zur herstellung von allopurinol. |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH654009A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3325853A1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102219787B (zh) * | 2011-05-17 | 2013-06-05 | 重庆万利康制药有限公司 | 一种4-羟基吡唑并[3,4-d]嘧啶的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2868803A (en) * | 1956-02-10 | 1959-01-13 | Ciba Pharm Prod Inc | New pyrazoles and method of preparing same |
| GB854632A (en) * | 1956-02-10 | 1960-11-23 | Ciba Ltd | Manufacture of pyrazoles |
| GB1252435A (enrdf_load_stackoverflow) * | 1968-02-02 | 1971-11-03 |
-
1983
- 1983-03-21 CH CH151883A patent/CH654009A5/de not_active IP Right Cessation
- 1983-07-18 DE DE19833325853 patent/DE3325853A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3325853C2 (enrdf_load_stackoverflow) | 1989-06-01 |
| DE3325853A1 (de) | 1984-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |