Claims
- 1. A compound of the formula: ##STR4## 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, ethoxycarbonyl or halogen; R.sub.3 is hydrogen, straight or branched chain lower alkyl(C.sub.1 -C.sub.3), alkyl(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), ethoxycarbonyl, alkyl(C.sub.1 -C.sub.13)carbonyl, 1-[2-(methylethyl)amino-2-oxoethyl], 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)), benzoyl, 4-methoxybenzoyl, straight or branched chain alkyl(C.sub.2 -C.sub.3)phenyl, (4-chlorophenyl)phenylmethyl, 1,3-benzodioxol-5-ylmethyl, 1,3-benzodioxol-5yl, 2-furanyl-carbonyl, 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, (2-oxo-1-pyrrolidinyl)-2-butynyl, phenylmethoxycarbonyl, or (2-phenyl-2H-1,2,3-triazol-4yl)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.
- 2. A compound according to claim 1, 7-(2,5-Dichlorophenyl)-4-[[4-(2,5-dimethylphenyl)-1-piperazinyl]-acetyl]-4,5-dihydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile.
- 3. A compound according to claim 1, 4-[(4-Benzoyl-1-piperazinyl)acetyl]-4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile.
- 4. A compound according to claim 1, 7-(2,5-Dichlorophenyl)-4,5-dihydro-4-[4-phenyl-1-piperazinyl) acetyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile.
- 5. A compound according to claim 1, 4-[(4-Cyclobutyl-1-piperazinyl]-acetyl]-4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile, dihydrochloride.
- 6. A compound according to claim 1, 4,5-Dihydro-4-[[4-[(2-phenyl-2H-1,2,3-triazol-4-yl)methyl]-1-piperazinyl]acetyl]7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile
- 7. A compound according to claim 1, 4-[2-[3-Cyano-70[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-4(5H)-yl]-2-oxoethyl]-1-piperazinecarboxylic acid, phenylmethylester.
- 8. A compound 4,5-Dihydro-4-[[4-(2-phenylethyl)-1-piperazinyl]actyl]-7-[3-trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile.
- 9. A therapeutic composition of matter in dosage unit form comprising from about 10 mg to about 500 mg per dosage unit of a compound of claim 1, in association with a pharmaceutically acceptable carrier. 4
- 10. A method of treating depression in a warm-blooded animal which comprises administering internally to said animal an antidepressant amount of a compound of claim 1.
Parent Case Info
This is a divisional of co-pending U.S. application Ser. No. 07/238,005, filed on Aug. 29, 1988, (now U.S. Pat. No. 4,963,553 (1990)), which in turn is a Continuation-in-part of U.S. Ser. No. 919,731 filed Oct. 16, 1986, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4448962 |
Irikura et al. |
May 1984 |
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4963553 |
Tseng et al. |
Oct 1990 |
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Foreign Referenced Citations (1)
Number |
Date |
Country |
264773 |
Apr 1988 |
EPX |
Divisions (1)
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Number |
Date |
Country |
Parent |
238005 |
Aug 1988 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
919731 |
Oct 1986 |
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