US4223137A
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Carbostyril derivatives and process for preparing the same
Assignee: Otsuka Pharmaceutical Co Ltd
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Filing: 1978-08-10
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Granted: 1980-09-16
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Expires: 1998-08-10
Abstract
Abstract Carbostyril derivative represented by the formula (I): ##STR1## wherein R 1 and R 2 , which may be the same or different, each represents a hydrogen atom, a cycloalkylcarbonyl group, a cycloalkylalkanoyl group, a benzoyl group, an alkanoyl group or a phenylalkylcarbonyl group; R 4 represents a hydrogen atom or an alkyl group, R 5 and R 6 , which may be the same or different, each represents a hydrogen atom, an alkyl group, a cycloalkyl group, or a phenylalkyl group, or R 5 and R 6 may, when taken together with the nitrogen atom to which they are attached, form a 5- or 6-membered substituted or unsubstituted heterocyclic ring containing 1 or 2 nitrogen or oxygen atoms as hetero atoms; and the ring A has a partial structure: ##STR2## wherein R 3 represents a hydrogen atom, a cycloalkylcarbonyl group, a cycloalkylalkanoyl group, a benzoyl group, an alkanoyl group or a phenylalkylcarbonyl group, with the proviso that at least one of R 1 , R 2 and R 3 when R 3 is present, or at least one of R 1 and R 2 when R 3 is absent, represents a cycloalkylcarbonyl group, a cycloalkylalkanoyl group, a benzoyl group, an alkanoyl group or a phenylalkylcarbonyl group; the pharmaceutically acceptable acid addition salts of the above carbostyril compounds represented by the formula (I), and processes for preparing the above carbostyril compounds represented by the formula (I).
Inventors
- 👤 Shiro Yoshizaki
- 👤 Shigeharu Tamada
- 👤 Eiyu Yo
- 👤 Kazuyuki Nakagawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 20:37
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/24; C07D215/26; C07D215/32; A; A61; A61P; A61P11/00; A61P11/08; A61P25/00; A61P25/02
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
281 words
A carbostyril compound represented by the formula (I): ##STR38## and the ring A has a partial structure: ##STR39## wherein R 1 , R 2 and R 3 , which may be the same or different, each represents a hydrogen atom, a cycloalkylcarbonyl group having 4 to 8 carbon atoms, a cycloalkylalkanoyl group having 3 to 7 carbon atoms in the cycloalkyl moiety and 2 to 4 carbon atoms in the alkanoyl moiety, a benzoyl group, an alkanoyl group having 2 to 6 carbon atoms or a phenylalkylcarbonyl group having 1 to 4 carbon atoms in the alkyl moiety; R 4 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 5 and R 6 , which may be the same or different, each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 6 carbon atoms, or a phenylalkyl group having 1 to 4 carbon atoms in the alkyl moiety, or R 5 and R 6 may, when taken together with the nitrogen atom to which they are attached, form a heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, morpholino and piperazino, which heterocyclic ring can be unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms; with the proviso that at least one of R 1 , R 2 and R 3 represents said cycloalkylcarbonyl group, said cycloalkylalkanoyl group, said benzoyl group, said alkanoyl group, or said phenylalkylcarbonyl group and each of R 1 and R 2 is not a hydrogen atom when R 3 is absent; and pharmaceutically acceptable acid addition salts of said carbostyril compounds of the formula (I).
Claim 2
Dependent Claim
281 words
A carbostyril compound represented by the formula (I): ##STR38## and the ring A has a partial structure: ##STR39## wherein R 1 , R 2 and R 3 , which may be the same or different, each represents a hydrogen atom, a cycloalkylcarbonyl group having 4 to 8 carbon atoms, a cycloalkylalkanoyl group having 3 to 7 carbon atoms in the cycloalkyl moiety and 2 to 4 carbon atoms in the alkanoyl moiety, a benzoyl group, an alkanoyl group having 2 to 6 carbon atoms or a phenylalkylcarbonyl group having 1 to 4 carbon atoms in the alkyl moiety; R 4 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 5 and R 6 , which may be the same or different, each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 6 carbon atoms, or a phenylalkyl group having 1 to 4 carbon atoms in the alkyl moiety, or R 5 and R 6 may, when taken together with the nitrogen atom to which they are attached, form a heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, morpholino and piperazino, which heterocyclic ring can be unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms; with the proviso that at least one of R 1 , R 2 and R 3 represents said cycloalkylcarbonyl group, said cycloalkylalkanoyl group, said benzoyl group, said alkanoyl group, or said phenylalkylcarbonyl group and each of R 1 and R 2 is not a hydrogen atom when R 3 is absent; and pharmaceutically acceptable acid addition salts of said carbostyril compounds of the formula (I).
Claim 3
Dependent Claim
42 words
The carbostyril compound according to claim 1 represented by the formula (Ib): ##STR40## wherein R 1 , R 2 , R 4 , R 5 and R 6 are as defined in claim 1, and the pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim
5 words
5-(1-Isobutyryloxy-2-isopropylaminobutyl)-8-isobutyryloxycarbostyril, according to claim 2.
Claim 5
Dependent Claim
5 words
8-Acetoxy-5-(1-acetoxy-2-isopropylaminobutyl)carbostyril, according to claim 2.
Claim 6
Dependent Claim
5 words
5-(1-Cyclohexylcarbonyloxy-2-isopropylaminobutyl)-8-cyclohexylcarbonyloxycarbostyril, according to claim 2.
Claim 7
Dependent Claim
5 words
5-(1-p-Methylbenzoyloxy-2-isopropylaminobutyl)-8-p-methylbenzoyloxycarbostyril, according to claim 2.
Claim 8
Dependent Claim
5 words
5-(1-p-Methylbenzoyloxy-2-isopropylaminobutyl)-8-p-methylbenzoyloxy-3,4-dihydrocarbostyril, according to claim 2.
Claim 9
Dependent Claim
5 words
8-Cyclohexylcarbonyloxy-5-(1-isobutyryloxy-2-isopropylaminobutyl)carbostyril, according to claim 2.
Claim 10
Dependent Claim
5 words
8-Toluyloxy-5-(1-cyclohexylcarbonyloxy-2-isopropylaminobutyl)carbostyril, according to claim 2.
Claim 11
Dependent Claim
5 words
5-[1-Cyclopropylcarbonyloxy-2-(3,4-dimethoxyphenethylamino)ethyl]-8-cyclopropylcarbonyloxycarbostyril, according to claim 2.
Claim 12
Dependent Claim
56 words
The carbostyril compound according to claim 1 represented by the formula (Ia): ##STR41## wherein R 1 represents said cycloalkylcarbonyl group, said cycloakylalkanoyl group, said benzoyl group, said alkanoyl group or said phenylalkylcarbonyl group and R 4 , R 5 and R 6 are as defined in claim 1, and the pharmaceutically acceptable acid addition salts thereof.
Claim 13
Dependent Claim
5 words
5-(1-Hydroxy-2-isopropylaminobutyl)-8-isobutyryloxycarbostyril, according to claim 11.
Claim 14
Dependent Claim
5 words
5-(1-Hydroxy-2-ethylaminobutyl)-8-acetoxycarbostyril, according to claim 11.
Claim 15
Dependent Claim
6 words
5-(1-Hydroxy-2-tert-butylaminopropyl)-8-isobutyryloxy carbostyril, according to claim 11.
Claim 16
Dependent Claim
5 words
5-(1-Hydroxy-2-isopropylaminobutyl)-8-isobutyryloxy-3,4-dihydrocarbosytril, according to claim 11.
Claim 17
Dependent Claim
5 words
5-(1-Hydroxy-2-isopropylaminobutyl)-8-cyclohexylcarbonyloxycarbostyril, according to claim 11.
Claim 18
Dependent Claim
5 words
5-(1-Hydroxy-2-isopropylaminobutyl)-8-p-methylbenzoyloxycarbostyril, according to claim 11.
Claim 19
Dependent Claim
5 words
5-(1-Hydroxy-2-isopropylaminobutyl)-8-p-methylbenzoyloxy-3,4-dihydrocarbostyril, according to claim 11.
Claim 20
Dependent Claim
5 words
5-(1-Hydroxy-2-α,α-dimethylphenethylaminoethyl)-8-cyclohexylcarbonyloxycarbostyril, according to claim 11.
Claim 21
Dependent Claim
5 words
5-(1-Hydroxy-2-isopropylaminobutyl)-8-(3,4-dimethoxyphenylcarbonyloxy)carbostyril, according to claim 11.
Claim 22
Dependent Claim
5 words
5-(1-Hydroxy-2-ethylaminobutyl)-8-(β-cyclohexylpropionyloxy)carbostyril, according to claim 11.
Claim 23
Dependent Claim
5 words
5-(1-Hydroxy-2-isopropylaminobutyl)-8-phenylacetyloxycarbostyril, according to claim 11.
Claim 24
Dependent Claim
5 words
5-(1-Hydroxy-2-benzylaminobutyl)-8-(p-chlorobenzoyloxy)carbostyril, according to claim 11.
Claim 25
Dependent Claim
5 words
5-(1-Hydroxy-2-tert-butylaminopropyl)-8-(3,4-methylenedioxyphenylcarbonyloxy)carbostyril, according to claim 11.
Claim 26
Dependent Claim
5 words
5-(1-Hydroxy-2-isopropylaminobutyl)-8-(3,3-dimethylbutyryloxy)carbostyril, according to claim 11.
Claim 27
Dependent Claim
45 words
The carbostyril compound according to claim 1 represented by the formula (Id) ##STR42## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in claim 1, and the pharmaceutically acceptable acid addition salts thereof.
Claim 28
Dependent Claim
28 words
The carbostyril compound of claim 1 wherein each of R 1 and R 2 , which may be the same or different, do not represent a hydrogen atom.
Claim 29
Dependent Claim
29 words
The carbostyril compound according to claim 2 wherein each of R 1 and R 2 , which may be the same or different, do not represent a hydrogen atom.
Claim 30
Dependent Claim
30 words
The carbostyril compound according to claim 26 wherein R 1 , R 2 and R 3 which may be the same or different, each do not represent a hydrogen atom.
Claim 31
Dependent Claim
33 words
The carbostyril compound according to claim 1 wherein the carbon-to-carbon bonding between the 3 and 4 position of the carbostyril nucleus is a double bond, and the pharmaceutically acceptable acid addition salts thereof.
Claim 32
Dependent Claim
22 words
The carbostyril compound according to claim 26 wherein R 4 represents an alkyl group, and the pharmaceutically acceptable acid addition salts thereof.
Claim 33
Dependent Claim
22 words
The carbostyril compound according to claim 1 wherein R 4 represents a hydrogen atom, and the pharmaceutically acceptable acid addition salts thereof.
Claim 34
Dependent Claim
22 words
The carbostyril compound according to claim 1 wherein R 1 represents a benzoyl group, and the pharmaceutically acceptable acid addition salts thereof.
Claim 35
Dependent Claim
22 words
The carbostyril compound according to claim 1 wherein R 1 represents an alkanoyl group, and the pharmaceutically acceptable acid addition salts thereof.
Claim 36
Dependent Claim
20 words
The carbostyril compound according to claim 1 wherein R 1 represents a phenylalkylcarbonyl group, and the acid addition salts thereof.
Claim 37
Dependent Claim
22 words
The carbostyril compound according to claim 1 wherein R 1 represents a cycloalkylcarbonyl group, and the pharmaceutically acceptable acid addition salts thereof.
Claim 38
Dependent Claim
21 words
The carbostyril compound to claim 1 wherein R 1 represents a cycloalkylalkanoyl group, and the pharmaceutically acceptable acid addition salts thereof.
Claim 39
Dependent Claim
5 words
8-(4-methylbenzoyloxy)-5-(1-hydroxy-2-ethylaminobutyl)-carbostyril, according to claim 1.
References Cited (Backward Citations)
BE823841A
Cited
US3975391A
Cited
US4022776A
Cited
US4022784A
Cited
US4026897A
Cited
US3994901A
Cited
US4072683A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-16 | 1984-03-17 | 1984-09-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-16 | 1988-03-17 | 1988-09-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-16 | 1992-03-17 | 1992-09-16 | $7700.00 | Window Closed / Lapsed |