DE1620089A1 - Verfahren zur Herstellung von 4-substituierten 1-Alkyl-6-(5-nitro-2-furyl)-1H-pyrazolo[3,4-d]pyrmidinen - Google Patents
Verfahren zur Herstellung von 4-substituierten 1-Alkyl-6-(5-nitro-2-furyl)-1H-pyrazolo[3,4-d]pyrmidinenInfo
- Publication number
- DE1620089A1 DE1620089A1 DE19661620089 DE1620089A DE1620089A1 DE 1620089 A1 DE1620089 A1 DE 1620089A1 DE 19661620089 DE19661620089 DE 19661620089 DE 1620089 A DE1620089 A DE 1620089A DE 1620089 A1 DE1620089 A1 DE 1620089A1
- Authority
- DE
- Germany
- Prior art keywords
- furyl
- nitro
- pyrazolo
- group
- alkyl
- 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
- -1 5-nitro-2-furyl Chemical group 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009885 systemic effect Effects 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US473914A US3350397A (en) | 1965-07-20 | 1965-07-20 | 4-amino-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo [3, 4-d] pyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620089A1 true DE1620089A1 (de) | 1970-03-12 |
Family
ID=23881527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620089 Pending DE1620089A1 (de) | 1965-07-20 | 1966-04-30 | Verfahren zur Herstellung von 4-substituierten 1-Alkyl-6-(5-nitro-2-furyl)-1H-pyrazolo[3,4-d]pyrmidinen |
Country Status (12)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758050A (fr) * | 1969-10-28 | 1971-04-27 | Geigy Ag J R | Derives 5-nitro-furyliques et medicaments contenant de tels composes |
| US3948913A (en) * | 1971-04-27 | 1976-04-06 | Ciba-Geigy Corporation | New 5-nitrofuryl derivatives |
| US4044130A (en) * | 1974-07-03 | 1977-08-23 | Ciba-Geigy Corporation | Compositions for the control of microorganisms |
| US5294612A (en) * | 1992-03-30 | 1994-03-15 | Sterling Winthrop Inc. | 6-heterocyclyl pyrazolo [3,4-d]pyrimidin-4-ones and compositions and method of use thereof |
| US5656629A (en) * | 1995-03-10 | 1997-08-12 | Sanofi Winthrop, Inc. | 6-substituted pyrazolo (3,4-d)pyrimidin-4-ones and compositions and methods of use thereof |
| WO2009097446A1 (en) * | 2008-01-30 | 2009-08-06 | Genentech, Inc. | Pyrazolopyrimidine pi3k inhibitor compounds and methods of use |
| EP4559520A1 (en) * | 2023-11-21 | 2025-05-28 | Origenis GmbH | Novel aqp4 inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB937725A (en) * | 1960-05-11 | 1963-09-25 | Ciba Ltd | Pyrazolo[3:4-d]pyrimidines |
-
0
- FR FR206D patent/FR206F/fr active Active
-
1965
- 1965-07-20 US US473914A patent/US3350397A/en not_active Expired - Lifetime
-
1966
- 1966-04-30 DE DE19661620089 patent/DE1620089A1/de active Pending
- 1966-05-04 ES ES0326323A patent/ES326323A2/es not_active Expired
- 1966-05-18 AT AT474466A patent/AT262987B/de active
- 1966-06-16 SE SE08235/66A patent/SE326965B/xx unknown
- 1966-06-20 CH CH887966A patent/CH481134A/de not_active IP Right Cessation
- 1966-06-21 BE BE682871D patent/BE682871A/xx unknown
- 1966-06-30 NL NL6609134A patent/NL6609134A/xx unknown
- 1966-07-18 GB GB32253/66A patent/GB1108288A/en not_active Expired
- 1966-07-19 NO NO163992A patent/NO118494B/no unknown
- 1966-07-20 BR BR181430/66A patent/BR6681430D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1108288A (en) | 1968-04-03 |
| AT262987B (de) | 1968-07-10 |
| NL6609134A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-01-23 |
| NO118494B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-01-05 |
| ES326323A2 (es) | 1967-03-01 |
| BR6681430D0 (pt) | 1973-12-26 |
| BE682871A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-21 |
| SE326965B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-08-10 |
| CH481134A (de) | 1969-11-15 |
| US3350397A (en) | 1967-10-31 |
| FR206F (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
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