ES267249A1 - New pyrazolo-pyrimidines and process for the preparation thereof - Google Patents
New pyrazolo-pyrimidines and process for the preparation thereofInfo
- Publication number
- ES267249A1 ES267249A1 ES0267249A ES267249A ES267249A1 ES 267249 A1 ES267249 A1 ES 267249A1 ES 0267249 A ES0267249 A ES 0267249A ES 267249 A ES267249 A ES 267249A ES 267249 A1 ES267249 A1 ES 267249A1
- Authority
- ES
- Spain
- 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
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 |
|---|---|
| ES267249A1 true ES267249A1 (en) | 1961-11-01 |
Family
ID=25694208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0267249A Expired ES267249A1 (en) | 1960-05-11 | 1961-05-09 | New pyrazolo-pyrimidines and process for the preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES267249A1 (en) |
| GB (1) | GB937724A (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10238722A1 (en) | 2002-08-23 | 2004-03-11 | Bayer Ag | Improving attention, concentration, cognition, learning and/or memory performance, using selective phosphodiesterase 9A inhibitors, preferably 4H-pyrazolo-(3,4-d)-pyrimidin-4-one derivatives |
| DE10238723A1 (en) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl substituted pyrazolyprimidines |
| DE10238724A1 (en) | 2002-08-23 | 2004-03-04 | Bayer Ag | New 6-alkyl-1,5-dihydro-4H-pyrazolo-(3,4-d)-pyrimidin-4-ones useful as selective phosphodiesterase 9A inhibitors for improving attention, concentration, learning and/or memory performance |
| 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 |
| DE10320785A1 (en) | 2003-05-09 | 2004-11-25 | Bayer Healthcare Ag | 6-arylmethyl substituted pyrazolopyrimidines |
| DE102004001873A1 (en) | 2004-01-14 | 2005-09-29 | Bayer Healthcare Ag | Cyanopyrimidinone |
| JP5498392B2 (en) | 2007-11-30 | 2014-05-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 1,5-Dihydro-pyrazolo [3,4-D] pyrimidin-4-one derivatives and their use as PDE9A modulators for the treatment of CNS disorders |
| UA105362C2 (en) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| NZ590788A (en) | 2008-09-08 | 2012-11-30 | Boehringer Ingelheim Int | Pyrazolopyrimidines and their use for the treatment of cns disorders |
| MX2011010184A (en) | 2009-03-31 | 2011-10-28 | Boehringer Ingelheim Int | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators. |
| CN105541849B (en) | 2010-08-12 | 2018-03-23 | 勃林格殷格翰国际有限公司 | The ketone derivatives of the dihydro-pyrazolo of 6 cycloalkyl 1,5 [3,4 d] pyrimidine 4 and its purposes as PDE9A inhibitor |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones 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
Also Published As
| Publication number | Publication date |
|---|---|
| GB937724A (en) | 1963-09-25 |
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