2-(1-Piperazinyl)-4-phenylcycloalkanopyridine derivatives, processes for the production thereof, and pharmaceutical composition containing the same
First Claim
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1. A compound of the formula (I):
- ##STR83## wherein n is 3, 4, 5, 6 or 7, R1 is a hydrogen atom, C1 -C10 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C3 -C8 cycloalkyl, C3 -C6 cycloalkyl-(C1 -C4) alkyl, hydroxy-(C2 -C6) alkyl, C1 -C3 alkoxy-(C2 -C6) alkyl, C1 -C4 alkanoyloxy (C2 -C6) alkyl, C5 -C6 cycloalkylcarbonyloxy (C2 -C6) alkyl, benzoyloxy (C2 -C6) alkyl which is optionally substituted by halogen, C1 -C3 alkyl or C1 -C3 alkoxy, furoyloxy (C2 -C6) alkyl, thenoyloxy (C2 -C6) alkyl, pyridylcarbonyloxy (C2 -C6)alkyl, pyrimidylcarbonyloxy (C2 -C6) alkyl or isoquinolylcarbonyloxy (C2 -C6) alkyl, a benzoyl or naphthyloyl (C1 -C6) alkyl group which is optionally mono- or disubstituted on the phenyl or naphthyl ring by substituents(s) selected from the group consisting of halogen, C.sub. 1 -C3 alkyl, C1 -C3 alkoxy and trifluoromethyl, a phenyl or napthyl group which is optionally mono- or disubstituted by substituent(s) selected from the group consisting of halogen, C1 -C3 alkyl, C1 -C3 alkoxy and trifluoromethyl, furyl, thienyl, pyridyl, pyrimidyl or isoquinolyl, C1 -C4 alkanoyl, C5 -C6 cycloalkylcarbonyl, a benzoyl group which is optionally substituted by halogen, C1 -C3 alkyl or C1 -C3 alkoxy, furoyl, thenoyl, pyridylcarbonyl, pyrimidylcarbonyl or isoquinolylcarbonyl,R2 and R3 are the same or different and are each a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 alkoxy, trifluoromethyl, or hydroxy,R4, R5 and R6 are the same or different and are each a hydrogen atom, C1 -C6 alkyl, or phenyl, or two of R4, R5 and R6 combine to form a single bond or C1 -C3 alkylene,R7 and R8 are the same or different and are each a hydrogen atom or C1 -C3 alkyl,m is 2 or 3,or an acid addition salt thereof.
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Abstract
Novel 2-(1-piperazinyl)-4-phenyl-cycloalkanopyridine derivatives of the formula (I): ##STR1## wherein n is 3, 4, 5, 6 or 7; R1 is a hydrogen atom, C1 -C10 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C3 -C8 cycloalkyl, C3 -C6 cycloalkyl-(C1 -C4) alkyl, hydroxy-(C2 -C6) alkyl, C1 -C3 alkoxy-(C2 -C6) alkyl, acyloxy-(C2 -C6), alkyl, unsubstituted or substituted aroyl-(C1 -C6) alkyl, unsubstituted or substituted aryl, heteroaryl, or acyl; R2 and R3 are the same or different and are each a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 alkoxy, trifluoromethyl, or hydroxy; R4, R5 and R6 are the same or different and are each a hydrogen atom, C1 -C6 alkyl, or phenyl, or two of R4, R5 and R6 combine to form a single bond or C1 -C3 alkylene; R7 and R8 are the same or different and are each a hydrogen atom or C1 -C3 alkyl; m is 2 or 3, or an acid addition salt thereof, which is useful as a psychotropic drug, and processes for the preparation thereof.
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Citations
19 Claims
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1. A compound of the formula (I):
- ##STR83## wherein n is 3, 4, 5, 6 or 7, R1 is a hydrogen atom, C1 -C10 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C3 -C8 cycloalkyl, C3 -C6 cycloalkyl-(C1 -C4) alkyl, hydroxy-(C2 -C6) alkyl, C1 -C3 alkoxy-(C2 -C6) alkyl, C1 -C4 alkanoyloxy (C2 -C6) alkyl, C5 -C6 cycloalkylcarbonyloxy (C2 -C6) alkyl, benzoyloxy (C2 -C6) alkyl which is optionally substituted by halogen, C1 -C3 alkyl or C1 -C3 alkoxy, furoyloxy (C2 -C6) alkyl, thenoyloxy (C2 -C6) alkyl, pyridylcarbonyloxy (C2 -C6)alkyl, pyrimidylcarbonyloxy (C2 -C6) alkyl or isoquinolylcarbonyloxy (C2 -C6) alkyl, a benzoyl or naphthyloyl (C1 -C6) alkyl group which is optionally mono- or disubstituted on the phenyl or naphthyl ring by substituents(s) selected from the group consisting of halogen, C.sub. 1 -C3 alkyl, C1 -C3 alkoxy and trifluoromethyl, a phenyl or napthyl group which is optionally mono- or disubstituted by substituent(s) selected from the group consisting of halogen, C1 -C3 alkyl, C1 -C3 alkoxy and trifluoromethyl, furyl, thienyl, pyridyl, pyrimidyl or isoquinolyl, C1 -C4 alkanoyl, C5 -C6 cycloalkylcarbonyl, a benzoyl group which is optionally substituted by halogen, C1 -C3 alkyl or C1 -C3 alkoxy, furoyl, thenoyl, pyridylcarbonyl, pyrimidylcarbonyl or isoquinolylcarbonyl,
R2 and R3 are the same or different and are each a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 alkoxy, trifluoromethyl, or hydroxy, R4, R5 and R6 are the same or different and are each a hydrogen atom, C1 -C6 alkyl, or phenyl, or two of R4, R5 and R6 combine to form a single bond or C1 -C3 alkylene, R7 and R8 are the same or different and are each a hydrogen atom or C1 -C3 alkyl, m is 2 or 3, or an acid addition salt thereof. - View Dependent Claims (2, 3, 4, 6, 8, 15, 16, 17, 18, 19)
- ##STR83## wherein n is 3, 4, 5, 6 or 7, R1 is a hydrogen atom, C1 -C10 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C3 -C8 cycloalkyl, C3 -C6 cycloalkyl-(C1 -C4) alkyl, hydroxy-(C2 -C6) alkyl, C1 -C3 alkoxy-(C2 -C6) alkyl, C1 -C4 alkanoyloxy (C2 -C6) alkyl, C5 -C6 cycloalkylcarbonyloxy (C2 -C6) alkyl, benzoyloxy (C2 -C6) alkyl which is optionally substituted by halogen, C1 -C3 alkyl or C1 -C3 alkoxy, furoyloxy (C2 -C6) alkyl, thenoyloxy (C2 -C6) alkyl, pyridylcarbonyloxy (C2 -C6)alkyl, pyrimidylcarbonyloxy (C2 -C6) alkyl or isoquinolylcarbonyloxy (C2 -C6) alkyl, a benzoyl or naphthyloyl (C1 -C6) alkyl group which is optionally mono- or disubstituted on the phenyl or naphthyl ring by substituents(s) selected from the group consisting of halogen, C.sub. 1 -C3 alkyl, C1 -C3 alkoxy and trifluoromethyl, a phenyl or napthyl group which is optionally mono- or disubstituted by substituent(s) selected from the group consisting of halogen, C1 -C3 alkyl, C1 -C3 alkoxy and trifluoromethyl, furyl, thienyl, pyridyl, pyrimidyl or isoquinolyl, C1 -C4 alkanoyl, C5 -C6 cycloalkylcarbonyl, a benzoyl group which is optionally substituted by halogen, C1 -C3 alkyl or C1 -C3 alkoxy, furoyl, thenoyl, pyridylcarbonyl, pyrimidylcarbonyl or isoquinolylcarbonyl,
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5. A compound of the formula:
- ##STR84## wherein n1 is 3, 6 or 7, R11 is a hydrogen atom, C1 -C8 alkyl, C3 -C6 cycloalkyl, hydroxy-(C2 -C4) alkyl, C1 -C2 alkoxy-(C2 -C3) alkyl or C3 alkenyl,
R21 and R31 are the same or different and are each a hydrogen atom or fluorine atom, R71 and R81 are the same or different and are each a hydrogen atom or C1 -C3 alkyl, or an acid addition salt thereof. - View Dependent Claims (7, 9)
- ##STR84## wherein n1 is 3, 6 or 7, R11 is a hydrogen atom, C1 -C8 alkyl, C3 -C6 cycloalkyl, hydroxy-(C2 -C4) alkyl, C1 -C2 alkoxy-(C2 -C3) alkyl or C3 alkenyl,
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10. 2-(4-Ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine, or an acid addition salt thereof.
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11. 2-(4-Ethyl-1-piperazinyl)-4-(2,4-difluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine, or an acid addition salt thereof.
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12. 2-(4-n-Propyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine, or an acid addition salt thereof.
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13. 2-(4-Methyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine, or an acid addition salt thereof.
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14. 2-(4-Methyl-1-piperazinyl)-4-(2,4-difluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine, or an acid addition salt thereof.
Specification
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Current AssigneeDainippon Sumitomo Pharma Company Limited (Sumitomo Chemical Company Limited)
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Original AssigneeDainippon Pharmaceutical Co., Ltd. (Sumitomo Chemical Company Limited)
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InventorsSakamoto, Masato, Oka, Makoto, Kai, Naoki, Hino, Katsuhiko, Ochi, Yoshiaki, Furukawa, Kiyoshi, Kon, Tatsuya
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Primary Examiner(s)Shen, Cecilia
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Application NumberUS07/481,183Time in Patent Office469 DaysField of Search540/575, 544/361, 544/362, 544/363, 544/295, 514/218, 514/254US Class Current514/253.04CPC Class CodesC07D 215/38 Nitrogen atoms nitro radica...C07D 221/04 Ortho- or peri-condensed ri...C07D 221/22 Bridged ring systemsC07D 401/04 directly linked by a ring-m...C07D 401/12 linked by a chain containin...
