GB937726A - New 4-mercapto-pyrazolo[3,4-d]pyrimidines and process for preparing same - Google Patents
New 4-mercapto-pyrazolo[3,4-d]pyrimidines and process for preparing sameInfo
- Publication number
- GB937726A GB937726A GB17107/61A GB1710761A GB937726A GB 937726 A GB937726 A GB 937726A GB 17107/61 A GB17107/61 A GB 17107/61A GB 1710761 A GB1710761 A GB 1710761A GB 937726 A GB937726 A GB 937726A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolo
- mercapto group
- group
- resulting
- pyrimidine
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- PYAOPMWCFSVFOT-UHFFFAOYSA-N tisopurine Chemical class SC1=NC=NC2=C1C=NN2 PYAOPMWCFSVFOT-UHFFFAOYSA-N 0.000 title 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises a pyrazolo [3,4-d] pyrimidine of the formula: <FORM:0937726/IV(a)/1> or a tautomer thereof, in which R1 represents an alkyl, cycloalkyl or cycloalkyl-alkyl group, R3 represents a hydrogen atom or a lower alkyl group, R4 represents a free mercapto group or a mercapto group substituted by lower alkyl or an aminoalkyl group and R6 represents a lower alkyl or aralkyl group with the proviso that in a 1,6-dialkyl-3-R3-4-R4-pyrazolo [3,4,d] pyrimidine at least one of the alkyl groups in the 1 and 6-positions contain more than 2 carbon atoms, quaternary ammonium compounds thereof, salts thereof, pharmaceutical preparations thereof and a process for the preparation thereof wherein a 1-R1-3-R3-6-R6-4-X-pyrazolo [3,4-d] pyrimidine, in which X represents a halogen atom and R1, R3 and R6 are as defined above, is reacted with thiourea, a metal salt of a hydrogen sulphide or of an alkylmercaptan or aminoalkylmercaptan, and if desired, in the resulting compound with a free mercapto group, the latter is converted into a substituted mercapto group R4 by reaction with a reactive ester of an alkanol or aminoalkanol and, if desired, the resulting tertiary amine is quaternated and/or a resulting free compound converted into a salt thereof or a resulting salt into the free compound or alternatively a 1-R1-3-R3-6-R6-4-hydroxy-pyrazolo [3,4,d] pyrimidine is reacted with phosphorus pentasulphide and if desired, in a resulting compound with a free mercapto group the latter is converted into a substituted mercapto group as above. When R6 represents phenyl it may be mono-, di-, or tri-substituted by chlorine methoxy, methylene-dioxy or trifluoromethyl. 4-Halogeno-pyrazolo[3,4-d]-pyrimidines are obtained by treating a corresponding 4-hydroxy compound with a halogenating agent, e.g. POCl3. Said pharmaceutical compositions, having coronary-dilating activity, are administered enterally, parenterally or locally in the form of tablets or dragees or in liquid form as solutions, suspensions or emulsions. Specifications 937,722, 937,723 and 937,724 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH540560A CH390929A (en) | 1960-05-11 | 1960-05-11 | Process for the preparation of 4-mercapto-pyrazolo (3,4-d) pyrimidines |
| CH393361 | 1961-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB937726A true GB937726A (en) | 1963-09-25 |
Family
ID=25694213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17107/61A Expired GB937726A (en) | 1960-05-11 | 1961-05-10 | New 4-mercapto-pyrazolo[3,4-d]pyrimidines and process for preparing same |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1161281B (en) |
| GB (1) | GB937726A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004018474A1 (en) * | 2002-08-23 | 2004-03-04 | Bayer Healthcare Ag | Phenyl-substituted pyrazolopyrimidines |
| US7488733B2 (en) | 2003-06-25 | 2009-02-10 | Boehringer Ingelheim International Gmbh | 6-arylamino-5-cyano-4-pyrimidinones as pde9a inhibitors |
| US7615558B2 (en) | 2003-05-09 | 2009-11-10 | Boehringer Ingelheim International Gmbh | 6-arylmethylprazolo[3,4-d]pyrimidines |
| US7737156B2 (en) | 2002-08-23 | 2010-06-15 | Boehringer Ingelheim International Gmbh | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| EP2298773A1 (en) | 2003-05-09 | 2011-03-23 | Boehringer Ingelheim International GmbH | 6-Cyclomethyl and 6-alkylmethyl substituted pyrazolopyrimidines |
| US8039477B2 (en) | 2002-08-23 | 2011-10-18 | Boehringer Ingelheim International Gmbh | Substituted pyrazolo[3,4-d]pyrimidin-4-one compounds as phosphodiesterase inhibitors |
| US8044060B2 (en) | 2003-05-09 | 2011-10-25 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory |
| US8088769B2 (en) | 2004-01-14 | 2012-01-03 | Boehringer Ingelheim International Gmbh | Cyanopyrimidinones |
| US8623879B2 (en) | 2008-04-02 | 2014-01-07 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivates and their use as PDE9A modulators |
| US8623901B2 (en) | 2009-03-31 | 2014-01-07 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
| US8648085B2 (en) | 2007-11-30 | 2014-02-11 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo (3, 4-D) pyrimidin-4-one derivatives and their use as PDE9A mudulators for the treatment of CNS disorders |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US8912201B2 (en) | 2010-08-12 | 2014-12-16 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US9079905B2 (en) | 2008-09-08 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2073274A1 (en) * | 1969-12-15 | 1971-10-01 | Sapchim Fournier Cimag Sa | 4-mercapto-pyrazolo(3,4-d)-pyrimidines prepn |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1056613B (en) * | 1956-07-16 | 1959-05-06 | Ciba Geigy | Process for the preparation of 1-isopropyl-pyrazolo- [3, 4-d] -pyrimidines |
-
1961
- 1961-04-26 DE DE1961C0023979 patent/DE1161281B/en active Pending
- 1961-05-10 GB GB17107/61A patent/GB937726A/en not_active Expired
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8158633B2 (en) | 2002-08-23 | 2012-04-17 | Boehringer Ingelheim International Gmbh | Phenyl-substituted pyrazolopyrimidines |
| US8741907B2 (en) | 2002-08-23 | 2014-06-03 | Boehringer Ingelheim International Gmbh | Alkyl-substituted pyrazolopyrimidines |
| US9067945B2 (en) | 2002-08-23 | 2015-06-30 | Boehringer Ingehleim International GmbH | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| US7737156B2 (en) | 2002-08-23 | 2010-06-15 | Boehringer Ingelheim International Gmbh | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| WO2004018474A1 (en) * | 2002-08-23 | 2004-03-04 | Bayer Healthcare Ag | Phenyl-substituted pyrazolopyrimidines |
| EP2305262A1 (en) | 2002-08-23 | 2011-04-06 | Boehringer Ingelheim International GmbH | Selective PDE9A inhibitors as medicaments for the improvement of cognitive processes |
| US8039477B2 (en) | 2002-08-23 | 2011-10-18 | Boehringer Ingelheim International Gmbh | Substituted pyrazolo[3,4-d]pyrimidin-4-one compounds as phosphodiesterase inhibitors |
| US8455502B2 (en) | 2002-08-23 | 2013-06-04 | Boehringer Ingelheim International Gmbh | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| EP2298773A1 (en) | 2003-05-09 | 2011-03-23 | Boehringer Ingelheim International GmbH | 6-Cyclomethyl and 6-alkylmethyl substituted pyrazolopyrimidines |
| US8044060B2 (en) | 2003-05-09 | 2011-10-25 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory |
| US8822479B2 (en) | 2003-05-09 | 2014-09-02 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl-and 6-alkylmethyl-substituted pyrazolepyrimidines |
| US7615558B2 (en) | 2003-05-09 | 2009-11-10 | Boehringer Ingelheim International Gmbh | 6-arylmethylprazolo[3,4-d]pyrimidines |
| US8642605B2 (en) | 2003-05-09 | 2014-02-04 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl-and 6-alkylmethyl-substituted pyrazolepyrimidines |
| US8809348B2 (en) | 2003-05-09 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-arylmethyl substituted pyrazolo[3,4-d]pyrimidines |
| US7488733B2 (en) | 2003-06-25 | 2009-02-10 | Boehringer Ingelheim International Gmbh | 6-arylamino-5-cyano-4-pyrimidinones as pde9a inhibitors |
| US8088769B2 (en) | 2004-01-14 | 2012-01-03 | Boehringer Ingelheim International Gmbh | Cyanopyrimidinones |
| US8431573B2 (en) | 2004-01-14 | 2013-04-30 | Boehringer Ingelheim International Gmbh | Cyanopyrimidinones |
| US8648085B2 (en) | 2007-11-30 | 2014-02-11 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo (3, 4-D) pyrimidin-4-one derivatives and their use as PDE9A mudulators for the treatment of CNS disorders |
| US8623879B2 (en) | 2008-04-02 | 2014-01-07 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivates and their use as PDE9A modulators |
| US9096603B2 (en) | 2008-04-02 | 2015-08-04 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivatives and their use as PDE9A modulators |
| US9079905B2 (en) | 2008-09-08 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
| US8623901B2 (en) | 2009-03-31 | 2014-01-07 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
| US9102679B2 (en) | 2009-03-31 | 2015-08-11 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
| US8912201B2 (en) | 2010-08-12 | 2014-12-16 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US9328120B2 (en) | 2010-08-12 | 2016-05-03 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1161281B (en) | 1964-01-16 |
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