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US4487772A Expired / Lapsed US ⏱️ 0.0 years remaining

Carbostyril derivatives and their salts

Assignee: Otsuka Pharmaceutical Co Ltd
•
Filing: 1982-02-16
•
Granted: 1984-12-11
•
Expires: 2002-02-16
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Abstract

Abstract Carbostyril derivatives of the general formula ##STR1## wherein R 1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a phenyl-lower alkyl group and R 2 and R 3 may be the same or different and each is a substituted or unsubstituted lower alkyl group, or R 2 and R 3 may form, together with the adjacent nitrogen atom, a 5- or 6-membered saturated heterocyclic ring which may be substituted or unsubstituted. The derivatives are useful as the active ingredient in cardiotonic compositions.

Inventors

  • 👤 Michiaki Tominaga
  • 👤 Yung-hsiung Yang
  • 👤 Hidenori Ogawa
  • 👤 Kazuyuki Nakagawa

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 22:06
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/48; A; A61; A61P; A61P9/00; A61P9/04; C07C; C07C205/00; C07C205/49; C07C205/57; C07D413/00; C07D413/02; C07D413/12

Claims Analysis

Total Claims: 44
Claim 1
Independent Claim 509 words
A arbostyril derivative or a pharmaceutically acceptable salt thereof said derivative being represented by the formula (1), ##STR30## wherein R 1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a phenyl-lower lower alkyl group; R 2 and R 3 may form, together with the adjacent nitrogen atom and further with an additional nitrogen atom, a 6-membered saturated heterocyclic ring which may have a lower alkyl group or a phenyl-lower alkyl group as the substituent; when said heterocyclic ring is a piperazinyl group, said piperazinyl ring may have a lower alkyl group or a phenyl-lower alkyl group as the substituent at 4-position in the piperazinyl ring, further said piperazinyl group may have, as the substituent at 4-position, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a cycloalkyl-lower alkyl group, a lower alkanoyl group, a lower alkanoyl-lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyl-lower alkyl group, a furoyl group, a lower alkylsulfonyl group, a substituted lower alkyl group (having one substituent selected from the group consisting of a cyano group, a benzoyloxy group (which may have 1 to 3 lower alkoxy groups on the phenyl ring), a hydroxy group, a lower alkanoyloxy group, a halogen atom and a carbamoyl group), a phenoxy-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkoxy group and a lower alkyl group, or said phenoxy-lower alkyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), a phenyl-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, a lower alkanoylamino group and a lower alkylthio group, or said phenyl-lower alkyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), a benzoyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group and a cyano group, or said benzoyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), a phenyl-sulfonyl group (which may have, on the phenyl ring, 1 to 3 lower alkyl groups as the substituents), a benzoyl-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom, a hydroxy group, a lower alkyl group, a lower alkoxy group and a lower alkanoylamino group), a phenyl-lower alkenyl-carbonyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom and a lower alkoxy group), or a phenyl-lower alkanoyl group (which may have, on the phenyl ring, 1 to 3 lower alkoxy groups as the substitutents); the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton being a single or double bond.
Claim 2
Dependent Claim 509 words
A arbostyril derivative or a pharmaceutically acceptable salt thereof said derivative being represented by the formula (1), ##STR30## wherein R 1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a phenyl-lower lower alkyl group; R 2 and R 3 may form, together with the adjacent nitrogen atom and further with an additional nitrogen atom, a 6-membered saturated heterocyclic ring which may have a lower alkyl group or a phenyl-lower alkyl group as the substituent; when said heterocyclic ring is a piperazinyl group, said piperazinyl ring may have a lower alkyl group or a phenyl-lower alkyl group as the substituent at 4-position in the piperazinyl ring, further said piperazinyl group may have, as the substituent at 4-position, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a cycloalkyl-lower alkyl group, a lower alkanoyl group, a lower alkanoyl-lower alkyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyl-lower alkyl group, a furoyl group, a lower alkylsulfonyl group, a substituted lower alkyl group (having one substituent selected from the group consisting of a cyano group, a benzoyloxy group (which may have 1 to 3 lower alkoxy groups on the phenyl ring), a hydroxy group, a lower alkanoyloxy group, a halogen atom and a carbamoyl group), a phenoxy-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkoxy group and a lower alkyl group, or said phenoxy-lower alkyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), a phenyl-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, a lower alkanoylamino group and a lower alkylthio group, or said phenyl-lower alkyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), a benzoyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group and a cyano group, or said benzoyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), a phenyl-sulfonyl group (which may have, on the phenyl ring, 1 to 3 lower alkyl groups as the substituents), a benzoyl-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom, a hydroxy group, a lower alkyl group, a lower alkoxy group and a lower alkanoylamino group), a phenyl-lower alkenyl-carbonyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom and a lower alkoxy group), or a phenyl-lower alkanoyl group (which may have, on the phenyl ring, 1 to 3 lower alkoxy groups as the substitutents); the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton being a single or double bond.
Claim 3
Dependent Claim 15 words
Carbostyril derivative according to claim 1, wherein the heterocyclic ring formed is a 1-piperazinyl group.
Claim 4
Dependent Claim 39 words
Carbostyril derivative according to claim 2, wherein the piperazinyl group is substituted, at 4-position, with a lower alkylsulfonyl group or a phenyl-sulfonyl group (which may have, on the phenyl ring, 1 to 3 lower alkyl groups as the substituents).
Claim 5
Dependent Claim 131 words
Carbostyril derivative according to claim 2, wherein the piperazinyl group is substituted, at 4-position, with a lower alkanoyl group, a lower alkoxy-carbonyl group, a furoyl group, a benzoyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group and a cyano group, or said benzoyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), a phenyl-lower alkenylcarbonyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom and a lower alkoxy group), or a phenyl-lower alkanoyl group (which may have, on the phenyl ring, 1 to 3 lower alkoxy groups as the substituents).
Claim 6
Dependent Claim 248 words
Carbostyril derivative according to claim 2, wherein the piperazinyl group is substituted, at 4-position, with a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a cycloalkyl-lower alkyl group, a lower alkanoyl-lower alkyl group, a lower alkoxy-carbonyl-lower alkyl group, a substituted lower alkyl group (having one substituent selected from the group consisting of a cyano group, a hydroxy group, a carbamoyl group, a lower alkanoyloxy group, a halogen atom and a benzoyloxy group (which may have 1 to 3 lower alkoxy groups on the phenyl ring), a phenoxy-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkoxy group and a lower alkyl group, or said phenoxy-lower alkyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), a phenyl-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, a lower alkanoylamino group and a lower alkylthio group, or said phenyl-lower alkyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), or a benzoyl-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxy group and a lower alkanoylamino group).
Claim 7
Dependent Claim 13 words
Carbostyril derivative according to claim 4, wherein R 1 is a hydrogen atom.
Claim 8
Dependent Claim 19 words
Carbostyril derivative according to claim 5, wherein the piperazinyl group is substituted, at 4-position, with a lower alkyl group.
Claim 9
Dependent Claim 61 words
Carbostyril derivative according to claim 5, wherein the piperazinyl group is substituted, at 4-position, with a substituted lower alkyl group (having one substituent selected from the group consisting of a cyano group, a halogen atom, a hydroxy group, a lower alkanoyloxy group, carbamoyl group and a benzoyloxy group (which may have 1 to 3 lower alkoxy groups on the phenyl ring)).
Claim 10
Dependent Claim 107 words
Carbostyril derivative according to claim 5, wherein the piperazinyl ring is substituted, at 4-position, with a phenoxy-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkoxy group and a lower alkyl group, or said phenoxy-lower alkyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent), or a benzoyl-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a halogen atom, a hydroxy group, a lower alkyl group, a lower alkoxy group and a lower alkanoylamino group).
Claim 11
Dependent Claim 80 words
Carbostyril derivative according to claim 5, wherein the piperazinyl group is substituted, at 4-position, with a phenyl-lower alkyl group (which may have, on the phenyl ring, 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, a lower alkanoylamino group and a lower alkylthio group, or said phenyl-lower alkyl group may have, on the phenyl ring, a lower alkylenedioxy group as the substituent).
Claim 12
Dependent Claim 41 words
Carbostyril derivative according to claim 5, wherein the piperazinyl group is substituted, at 4-position, with a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a lower alkoxycarbonyl-lower alkyl group, a cycloalkyl-lower alkyl group or a lower alkanoyl-lower alkyl group.
Claim 13
Dependent Claim 22 words
Carbostyril derivatives according to claim 7, wherein the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton is a single bond.
Claim 14
Dependent Claim 22 words
Carbostyril derivative according to claim 7, wherein the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton is a double bond.
Claim 15
Dependent Claim 13 words
Carbostyril derivative according to claim 8, wherein R 1 is a hydrogen atom.
Claim 16
Dependent Claim 22 words
Carbostyril derivative according to claim 9, wherein the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton is a single bond.
Claim 17
Dependent Claim 22 words
Carbostyril derivative according to claim 9, wherein the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton is a double bond.
Claim 18
Dependent Claim 13 words
Carbostyril derivative according to claim 10, wherein R 1 is a hydrogen atom.
Claim 19
Dependent Claim 13 words
Carbostyril derivative according to claim 11, wherein R 1 is a hydrogen atom.
Claim 20
Dependent Claim 15 words
Carbostyril derivative according to claim 11 or 13 wherein R 1 is a hydrogen atom.
Claim 21
Dependent Claim 15 words
Carbostyril derivative according to claim 15 or 16 wherein R 1 is a hydrogen atom.
Claim 22
Dependent Claim 23 words
Carbostyril derivative according to claim 19, wherein the substituted position of a group of the formula, ##STR31## is 6-position in the carbostyril skeleton.
Claim 23
Dependent Claim 26 words
Carbostyril derivative according to claim 19, wherein the substituted position of a group of the formula, ##STR32## is 5-, 7- or 8-position in the carbostyril skeleton.
Claim 24
Dependent Claim 23 words
Carbostyril derivative according to claim 20, wherein the substituted position of a group of the formula, ##STR33## is 6-position in the carbostyril skeleton.
Claim 25
Dependent Claim 26 words
Carbostyril derivative according to claim 20, wherein the substituted position of a group of the formula, ##STR34## is 5-, 7- or 8-position in the carbostyril skeleton.
Claim 26
Dependent Claim 1 words
6-(4-Isobutyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril.
Claim 27
Dependent Claim 1 words
6-(4-Isobutyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril.
Claim 28
Dependent Claim 1 words
6-[4-(2-Phenylethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.
Claim 29
Dependent Claim 1 words
6-[4-(2-Phenylethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.
Claim 30
Dependent Claim 1 words
6-[4-(2-Phenoxyethyl)-1-piperazinylcarbonyl]-carbostyril.
Claim 31
Dependent Claim 1 words
6-[4-(2-Phenoxyethyl)-1-piperazinylcarbonyl]-carbostyril.
Claim 32
Dependent Claim 1 words
6-[4-(3-Phenylpropyl)-1-piperazinylcarbonyl]carbostyril.
Claim 33
Dependent Claim 1 words
6-[4-(3-Phenylpropyl)-1-piperazinylcarbonyl]carbostyril.
Claim 34
Dependent Claim 1 words
6-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril.
Claim 35
Dependent Claim 1 words
6-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril.
Claim 36
Dependent Claim 1 words
6-[4-(4-Methoxybenzyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.
Claim 37
Dependent Claim 1 words
6-[4-(4-Methoxybenzyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.
Claim 38
Dependent Claim 1 words
6-[4-(2-Phenoxyethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.
Claim 39
Dependent Claim 1 words
6-[4-(2-Phenoxyethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.
Claim 40
Dependent Claim 1 words
6-(4-Isobutyl-1-piperazinylcarbonyl)carbostyril.
Claim 41
Dependent Claim 1 words
6-(4-Isobutyl-1-piperazinylcarbonyl)carbostyril.
Claim 42
Dependent Claim 1 words
6-[4-(2-Benzoylethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.
Claim 43
Dependent Claim 1 words
6-[4-(2-Benzoylethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril.
Claim 44
Dependent Claim 24 words
A cardiotonic composition containing an effective amount a carbostyril derivative of claim 1 or one of its pharmaceutically acceptable salts as the active ingredient.

References Cited (Backward Citations)

US2997474A Cited
US4115569A Cited
US4145542A Cited
JPS51118771A Cited
JPS5416478A Cited
DE2928583A1 Cited
GB2071094A Cited

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