3,4-diaminoquinoline and 3,4-diamino-5,6,7,8-tetrahydroquinoline compounds useful for improving psychoneural function
First Claim
1. A 4-aminoquinoline or 4-amino-5,6,7,8-tetrahydroquinoline compound represented by the formula:
- ##STR155## wherein R1 is a hydrogen atom, a hydroxyl group, a linear or branched chain lower alkyl group or a cycloalkyl group which may be substituted by a hydroxyl group, a lower alkoxy group, a lower alkyl group or a cycloalkyl group which contains a carbonyl group, or a group --NH--B where B is a lower alkyl group, a cycloalkyl group, or a phenyl group;
R2 and R3, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, a lower alkyl carbonyl group, or when taken together, form a pyrrolidino group, a piperidino group, a morpholino group, or an N-methylpiperazinyl group, together with the nitrogen atom;
or an acid addition salt of said quinoline or 5,6,7,8-tetrahydroquinoline compound; and
when R1 is a hydrogen atom, R2 and R3 are neither a hydrogen atom nor an ethyl group at the same time.
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Accused Products
Abstract
4-aminopyridine derivatives represented by the general formula: ##STR1## [wherein R1 is a hydrogen atom, a hydroxyl group, a linear or branched lower alkyl group or a cycloalkyl group which may be substituted by a hydroxyl group, a lower alkoxy group, a lower alkyl or a cycloalkyl group which contains a carbonyl group, a morpholino group or a group --NH--B (where B is a lower alkyl group, a cycloalkyl group or a phenyl group); R2 and R3 which may be the same or different each represents a hydrogen atom, a lower alkyl group or a loweralkylcarbonyl group, or when taken together, form an azacycloalkyl group, a morpholino group or an N-methylpiperazinyl group together with the nitrogen atom; R4 and R5 each represents a hydrogen atom, or when taken together with the ring A, form a quinoline ring or a 5,6,7,8-tetrahydroquinoline ring, provided that when each of R1, R4 and R5 is a hydrogen atom, R2 and R3 are neither a hydrogen atom nor a methyl group at the same time, and when R1 is a hydrogen atom and R4 and R5 taken together with the ring A form a quinoline ring, R2 and R3 are neither a hydrogen atom nor an ethyl group at the same time], and an acid addition salts of said 4-aminopyridine derivatives. These compounds are useful as active ingredients in pharmaceutical compositions for improving psychoneural function, especially in the treatment of Alzheimer type dementia and promotion of mnemonic and learning performance.
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Citations
11 Claims
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1. A 4-aminoquinoline or 4-amino-5,6,7,8-tetrahydroquinoline compound represented by the formula:
- ##STR155## wherein R1 is a hydrogen atom, a hydroxyl group, a linear or branched chain lower alkyl group or a cycloalkyl group which may be substituted by a hydroxyl group, a lower alkoxy group, a lower alkyl group or a cycloalkyl group which contains a carbonyl group, or a group --NH--B where B is a lower alkyl group, a cycloalkyl group, or a phenyl group;
R2 and R3, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, a lower alkyl carbonyl group, or when taken together, form a pyrrolidino group, a piperidino group, a morpholino group, or an N-methylpiperazinyl group, together with the nitrogen atom;
or an acid addition salt of said quinoline or 5,6,7,8-tetrahydroquinoline compound; and
when R1 is a hydrogen atom, R2 and R3 are neither a hydrogen atom nor an ethyl group at the same time. - View Dependent Claims (2, 3, 4, 5, 6)
- ##STR155## wherein R1 is a hydrogen atom, a hydroxyl group, a linear or branched chain lower alkyl group or a cycloalkyl group which may be substituted by a hydroxyl group, a lower alkoxy group, a lower alkyl group or a cycloalkyl group which contains a carbonyl group, or a group --NH--B where B is a lower alkyl group, a cycloalkyl group, or a phenyl group;
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7. A pharmaceutical composition for improving psychoneural function which contains a pharmaceutically acceptable vehicle and an active ingredient which is a 4-aminoquinoline or 4-amino-5,6,7,8-tetrahydroquinoline compound represented by the formula:
- ##STR156## wherein R1 is a hydrogen atom, a hydroxyl group, a linear or branched chain lower alkyl group or a cycloalkyl group which may be substituted by a hydroxyl group, a lower alkoxy group, a lower alkyl group or a cycloalkyl group which contains a carbonyl group, or a group --NH--B where B is a lower alkyl group, a cycloalkyl group, or a phenyl group;
R2 and R3, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, a lower alkyl carbonyl group, or when taken together, form a pyrrolidino group, a piperidino group, a morpholino group, or an N-methylpiperazinyl group, together with the nitrogen atom;
or an acid addition salt of said quinoline or 5,6,7,8-tetrahydroquinoline compound; and
when R1 is a hydrogen atom, R2 and R3 are neither a hydrogen atom nor an ethyl group at the same time. - View Dependent Claims (8, 9, 10, 11)
- ##STR156## wherein R1 is a hydrogen atom, a hydroxyl group, a linear or branched chain lower alkyl group or a cycloalkyl group which may be substituted by a hydroxyl group, a lower alkoxy group, a lower alkyl group or a cycloalkyl group which contains a carbonyl group, or a group --NH--B where B is a lower alkyl group, a cycloalkyl group, or a phenyl group;
Specification
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- Resources
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Current AssigneeChugai Seiyaku Kabushiki Kaisha (Roche Holding AG)
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Original AssigneeChugai Seiyaku Kabushiki Kaisha (Roche Holding AG)
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InventorsFujimura, Yasuo, Takaku, Sakae, Noda, Yukifumi, Miura, Yutaka, Yoshida, Mitsutaka
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Primary Examiner(s)Lee, Mary C.
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Assistant Examiner(s)AMBROSE, MICHAEL GEORGE
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Application NumberUS07/414,170Time in Patent Office607 DaysField of Search544/128, 544/363, 546/157, 546/159, 546/160, 514/312, 514/313, 514/235.2, 514/254US Class Current514/235.2CPC Class CodesC07D 213/73 Unsubstituted amino or imin...C07D 213/74 Amino or imino radicals sub...C07D 215/42 attached in position 4
