GB937724A - New pyrazolo-pyrimidines and process for the preparation thereof - Google Patents
New pyrazolo-pyrimidines and process for the preparation thereofInfo
- Publication number
- GB937724A GB937724A GB1710561A GB1710561A GB937724A GB 937724 A GB937724 A GB 937724A GB 1710561 A GB1710561 A GB 1710561A GB 1710561 A GB1710561 A GB 1710561A GB 937724 A GB937724 A GB 937724A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazole
- amino
- isopropyl
- carboxylic acid
- formula
- 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
- 238000000034 method Methods 0.000 title abstract 3
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- -1 oxaalkyl Chemical group 0.000 abstract 5
- 150000001408 amides Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 150000002825 nitriles Chemical class 0.000 abstract 3
- UMQUIRYNOVNYPA-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1 UMQUIRYNOVNYPA-UHFFFAOYSA-N 0.000 abstract 2
- VLLNEKJPGZMQGQ-UHFFFAOYSA-N 5-(N-acetyl-4-chloroanilino)-1-propan-2-ylpyrazole-4-carboxylic acid Chemical compound C(C)(C)N1N=CC(=C1N(C(C)=O)C1=CC=C(C=C1)Cl)C(=O)O VLLNEKJPGZMQGQ-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 abstract 1
- HWLUYAARRNLXJL-UHFFFAOYSA-N 5-amino-1-propan-2-ylpyrazole-4-carbonitrile Chemical compound CC(C)N1N=CC(C#N)=C1N HWLUYAARRNLXJL-UHFFFAOYSA-N 0.000 abstract 1
- IAJRTGABDFKUSX-UHFFFAOYSA-N 5-amino-1-propan-2-ylpyrazole-4-carboxylic acid Chemical compound CC(C)N1N=CC(C(O)=O)=C1N IAJRTGABDFKUSX-UHFFFAOYSA-N 0.000 abstract 1
- QIXAOKYUEUFSLT-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-1-propan-2-yl-2H-pyrazolo[3,4-d]oxazin-4-one Chemical compound C(C)(C)N1NC=C2C1=CN(OC2=O)CC1=CC=C(C=C1)Cl QIXAOKYUEUFSLT-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 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
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- TWLDZIZAUAEFBE-UHFFFAOYSA-N n-(ethylamino)hydroxylamine Chemical compound CCNNO TWLDZIZAUAEFBE-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- OSDZHDOKXGSWOD-UHFFFAOYSA-N nitroxyl;hydrochloride Chemical compound Cl.O=N OSDZHDOKXGSWOD-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- 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:0937724/IV(a)/1> or a tautomer thereof, in which R1 represents a hydrogen atom or an alkyl, hydroxyalkyl, oxaalkyl, cycloalkyl, cycloalkylalkyl or aralkyl group or at most binuclear aryl or heterocyclic group, R3 represents a hydrogen atom or a lower alkyl group, and R6 represents an aralkyl group, salts thereof, pharmaceutical compositions thereof, and a process for the manufacture of compounds of the above formula wherein a 2-R1-3-amino-5-R3-pyrazole-4-carboxylic acid ester is reacted with a carboxylic acid of the formula R6-COOH in the form of its amide or nitrile or a 2-R1-3-amino-5-R3-pyrazole-4-carboxylic acid amide is reacted with a carboxylic acid of the formula R6-COOH in the form of its anhydride, or amide, or with a corresponding halide or nitrile. When R6 represents aralkyl, the phenyl nucleus may be mono-, di-, or tri-substituted by chlorine, methoxy, methylenedioxy, methyl, trifluoromethyl, amino or nitro groups. In a similar manner R1 may represent substituted phenyl. In a modification of the above process 2-R1-3-amino- 5-R3- pyrazole- 4-carboxylic acid amide is replaced by the nitrile, reacted with the derivative of the acid R6,COOH, converted into the amide followed by ring closure. Intermediate compounds having the formula: <FORM:0937724/IV(a)/2> are obtained by eliminating water from 2-R1-3-(R6-CONH)-4-carboxy-pyrazoles, e.g. with acetic anhydride. These compounds may be reacted with ammonia to obtain the acid amide. 2-(b -Hydroxyethyl)- 3-amino-4-carbethoxypyrazole is obtained by heating ethoxymethylene cyanoacetic ester with b -hydroxyethyl hydrazine. 2-[11-Ethoxy-butyl-(31)] -3-amino-4-carbethoxy pyrazole is obtained by heating ethoxymethylene cyanoacetic ester with 1-ethoxy-butyl-(3)-hydrazine. 2-a -Pyridyl-3-amino- 4-carbethoxy-pyrazole is obtained by heating ethoxy-methylene-cyanoacetic ester with 2-hydrazino-pyridine. 2-Isopropyl-3-[a -ethoxyb -(p-chlorophenyl) -ethylidene-amino]-pyrazole-4-carboxylic acid amide is obtained by forming the imino ether hydrochloride from p-chlorobenzyl cyanide and dry HC1 and boiling this with 2-isopropyl-3-amino-4-carbonamido pyrazole. 2-Isopropyl-3-(p-chloro-phenyl-acetylamino)-4-pyrazole-carboxylic acid nitrile is obtained by reacting 2-isopropyl-3-amino-4-cyano-pyrazole with p-chloro-phenylacetic acid chloride. 2-Isopropyl-3- (p-chlorophenyl-acetylamino)-4-carboxy-pyrazole is obtained by reacting p-chlorophenylacetic acid chloride with 2-isopropyl-3-amino-4-carboxy pyrazole. 1-Isopropyl-4-oxo- 6-(p-chlorobenzyl)-pyrazolo-[3,4-d] oxazine is obtained by heating 2-isopropyl-3-(parachlorophenyl-acetylamino)-4-carboxy-pyrazole with acetic anhydride. p Said compositions containing compounds of the first mentioned formula and having coronary-dilating action are administered as tablets or dragees or in liquid form as solutions, suspensions or emulsions. Specifications 937,725 and 937,726 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH540360A CH398626A (en) | 1960-05-11 | 1960-05-11 | Process for the preparation of new pyrazolopyrimidines |
| CH393161 | 1961-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB937724A true GB937724A (en) | 1963-09-25 |
Family
ID=25694208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1710561A Expired GB937724A (en) | 1960-05-11 | 1961-05-10 | New pyrazolo-pyrimidines and process for the preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES267249A1 (en) |
| GB (1) | GB937724A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006525963A (en) * | 2003-05-09 | 2006-11-16 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | 6-Arylmethyl-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 |
| US8158633B2 (en) | 2002-08-23 | 2012-04-17 | Boehringer Ingelheim International Gmbh | Phenyl-substituted pyrazolopyrimidines |
| US8455502B2 (en) | 2002-08-23 | 2013-06-04 | Boehringer Ingelheim International Gmbh | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| 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 |
-
1961
- 1961-05-09 ES ES0267249A patent/ES267249A1/en not_active Expired
- 1961-05-10 GB GB1710561A patent/GB937724A/en not_active Expired
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8158633B2 (en) | 2002-08-23 | 2012-04-17 | Boehringer Ingelheim International Gmbh | Phenyl-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 |
| US9067945B2 (en) | 2002-08-23 | 2015-06-30 | Boehringer Ingehleim International GmbH | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| US8741907B2 (en) | 2002-08-23 | 2014-06-03 | Boehringer Ingelheim International Gmbh | Alkyl-substituted pyrazolopyrimidines |
| US8455502B2 (en) | 2002-08-23 | 2013-06-04 | Boehringer Ingelheim International Gmbh | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| 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 |
| JP4889480B2 (en) * | 2003-05-09 | 2012-03-07 | ベーリンガー・インゲルハイム・インテルナツィオナール・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 6-Arylmethyl-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 |
| JP2006525963A (en) * | 2003-05-09 | 2006-11-16 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | 6-Arylmethyl-substituted pyrazolopyrimidines |
| 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 |
|---|---|
| ES267249A1 (en) | 1961-11-01 |
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