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Method of treating cognitive and related neural behavioral problems
| Details |
Inventors: Tseng, Shin S.; Brabander, Herbert J.; Epstein, Joseph W.;
Assignee: American Cyanamid Company (Stamford, CT)
Primary Examiner: Tsang; Cecilia
Assistant Examiner: Bernhardt; E.
Attorney, Agent or Firm: Jackson; H. G.
Novel compounds of the formula ##STR1## wherein n is an integer from 1 to 4 inclusive; R.sub.1 represents a mono-or disubstituent of hydrogen, lower alkyl(C.sub.1 -C.sub.3), lower alkoxy(C.sub.1 -C.sub.3), halogen, nitro or trifluoromethyl; R.sub.2 is cyano, carboxamido, ethyl carboxylate or halogen; R.sub.3 is hydrogen, straight or branched chain lower alkyl(C.sub.1 -C.sub.3), alkenyl(C.sub.2 -C.sub.3), alkynyl(C.sub.2 -C.sub.3), cycloalkyl(C.sub.3 -C.sub.6), hydroxyalkyl(C.sub.1 -C.sub.3), dimethylaminoalkyl(C.sub.1 -C.sub.3), ethylcarboxylate, alkyl(C.sub.1 -C.sub.13)carbonyl, 1-(methylethyl)acetamide, cyclohexylethyl, phenyl, mono-or disubstituted phenyl (wherein the phenyl substituent is halogen, trifluoromethyl, lower alkyl(C.sub.1 -C.sub.3) or lower alkoxy(C.sub.1 -C.sub.3)), benzyl, mono-or disubstituted benzyl (wherein the benzyl substituent is halogen, lower alkyl(C.sub.1 -C.sub.3), lower alkoxy(C.sub.1 -C.sub.3) or trifluoromethyl), benzoyl, 4-methoxybenzoyl, straight or branched chain alkyl(C.sub.2 -C.sub.3)phenyl, 4-chlorophenylphenylmethyl, 1,3-benzodioxol-5-ylmethyl, 1,3-benzodioxol-5-yl, 2-furanylcarbonyl, 2-pyrimidinyl, 2-pyridinyl, 4-morpholinyl-2-oxoethyl, 1-pyrrolidinyl-2-oxoethyl, bis(4-fluorophenyl)methyl, phenylcarboxamido, mono- and disubstituted phenylcarboximido (wherein the phenyl substituents is halogen, trifluoromethyl or lower alkyl(C.sub.1 -C.sub.3)), adamantanoyl, 3-phenoxypropyl,5-chloro-2-methoxyphenylacetamide, (2-oxo-1-pyrrolidinyl)-2-butynyl, phenylmethylcarboxylate, or (2-phenyl-2H-1,2,3-triazol-4-yl)methyl; R.sub.4 and R.sub.5 are independently hydrogen or lower alkyl(C.sub.1 -C.sub.3); the dotted line between positions 6 and 7 of the pyrimidine ring represents the presence or absence of a double bond; and the pharmacologically acceptable salts thereof: methods of producing them; therapeutic compositions containing them: and methods of using them to treat anxiety, hypertension, depression, senile dementia, cognitive defects and other neural behavior problems in warm-blooded animals. |
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DETAILED DESCRIPTION OF THE INVENTION The novel compounds of the invention are in general obtainable as white, yellow or tan crystalline solids having characteristic melting points and absorption spectra.
They are appreciably soluble in many organic solvents such as lower alkanols, chloroform, dichloromethane, tetrahydrofuran, acetone, N,N-dimethylformamide and the like, but are relatively insoluble in water.
These compounds are organic bases and thus are capable of forming acid-addition salts with a variety of organic and inorganic salt-forming reagents.
Thus, acid-addition salts, formed by admixture of the organic free base with an equivalent of an acid, suitably in a neutral solvent, are formed with such acids as sulfuric, phosphoric, hydrochloric, hydrobromic, sulfamic, citric, maleic, fumaric, tartaric, acetic, benzoic, gluconic, ascorbic, and related acids.
The acid addition salts of the novel compounds of the invention are, in general, crystalline solids relatively soluble in water, methanol and ethanol but relatively insoluble in non-polar organic solvents such as diethyl ether, benzene, toluene and the like.
For purposes of this invention the free bases are equivalent to their non-toxic acid-addition salts.
The novel 4-[(substituted)alkylcarbonyl]-4,5-dihydro- and -4,5,6,7-tetrahydro-7-[(substituted)phenyl]pyrazolo[1,5-a]pyrimidine-3-car bonitrile compounds of the present invention may be readily prepared as set forth in the following reaction scheme: ##STR3## In accordance with Scheme I a piperazine (1) where R.
sub.
3 is as described above is reacted with a halo-alkanoyl-4,5-dihydro- or -4,5,6,7-tetrahydro-7-substituted phenyl pyrazolo[1,5-a]pyrimidine-3-carbonitrile (2) where n, R1' R2, R4 and R5 are as described above, X is a halide such as chloro or iodo, and an alkaline carbonate in toluene at reflux giving the products (3).
The pharmacological activity of the compounds of the invention are demonstrated in the following tests.
A test used to assess antianxiety effects is the non-conditioned passive avoidance procedure described by J
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