DE2343702A1 - Verfahren zur herstellung von 4-mercapto-1h-pyrazolo eckige klammer auf 3,4-d eckige klammer zu pyrimidin - Google Patents
Verfahren zur herstellung von 4-mercapto-1h-pyrazolo eckige klammer auf 3,4-d eckige klammer zu pyrimidinInfo
- Publication number
- DE2343702A1 DE2343702A1 DE19732343702 DE2343702A DE2343702A1 DE 2343702 A1 DE2343702 A1 DE 2343702A1 DE 19732343702 DE19732343702 DE 19732343702 DE 2343702 A DE2343702 A DE 2343702A DE 2343702 A1 DE2343702 A1 DE 2343702A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrazolo
- pyrimidine
- chloro
- mercapto
- analogue
- 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.)
- Pending
Links
- 239000003513 alkali Substances 0.000 title claims abstract description 10
- PYAOPMWCFSVFOT-UHFFFAOYSA-N tisopurine Chemical compound SC1=NC=NC2=C1C=NN2 PYAOPMWCFSVFOT-UHFFFAOYSA-N 0.000 title claims description 6
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 title abstract 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 title abstract 2
- 239000003064 xanthine oxidase inhibitor Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 11
- YMXQUFUYCADCFL-UHFFFAOYSA-N 4-chloro-1h-pyrazolo[3,4-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=NN2 YMXQUFUYCADCFL-UHFFFAOYSA-N 0.000 claims description 9
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 5
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FLTNWMFPQFIBDA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2CCCCC2=C1.C1=CC=C2CCCCC2=C1 FLTNWMFPQFIBDA-UHFFFAOYSA-N 0.000 description 1
- XQSJHQXYQAUDFC-UHFFFAOYSA-N 4,6-dichloropyrimidine-5-carbaldehyde Chemical compound ClC1=NC=NC(Cl)=C1C=O XQSJHQXYQAUDFC-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000007280 thionation reaction Methods 0.000 description 1
- 238000010792 warming Methods 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE002055 HU166389B (enrdf_load_stackoverflow) | 1972-09-01 | 1972-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2343702A1 true DE2343702A1 (de) | 1974-04-04 |
Family
ID=10995453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732343702 Pending DE2343702A1 (de) | 1972-09-01 | 1973-08-30 | Verfahren zur herstellung von 4-mercapto-1h-pyrazolo eckige klammer auf 3,4-d eckige klammer zu pyrimidin |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5136278B2 (enrdf_load_stackoverflow) |
| AT (1) | AT328457B (enrdf_load_stackoverflow) |
| CA (1) | CA997343A (enrdf_load_stackoverflow) |
| DE (1) | DE2343702A1 (enrdf_load_stackoverflow) |
| DK (1) | DK138119B (enrdf_load_stackoverflow) |
| HU (1) | HU166389B (enrdf_load_stackoverflow) |
| NL (1) | NL7311748A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999024038A1 (en) | 1997-11-07 | 1999-05-20 | Johns Hopkins University | Methods for treatment of disorders of cardiac contractility |
-
1972
- 1972-09-01 HU HUEE002055 patent/HU166389B/hu unknown
-
1973
- 1973-08-24 DK DK466173A patent/DK138119B/da unknown
- 1973-08-27 NL NL7311748A patent/NL7311748A/xx not_active Application Discontinuation
- 1973-08-28 AT AT748473A patent/AT328457B/de not_active IP Right Cessation
- 1973-08-30 DE DE19732343702 patent/DE2343702A1/de active Pending
- 1973-08-31 JP JP9738773A patent/JPS5136278B2/ja not_active Expired
- 1973-08-31 CA CA180,123A patent/CA997343A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA997343A (en) | 1976-09-21 |
| DK138119B (da) | 1978-07-17 |
| ATA748473A (de) | 1975-06-15 |
| DK138119C (enrdf_load_stackoverflow) | 1978-12-18 |
| HU166389B (enrdf_load_stackoverflow) | 1975-03-28 |
| NL7311748A (enrdf_load_stackoverflow) | 1974-03-05 |
| AT328457B (de) | 1976-03-25 |
| JPS4992093A (enrdf_load_stackoverflow) | 1974-09-03 |
| JPS5136278B2 (enrdf_load_stackoverflow) | 1976-10-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |