US4567180A
Expired / Lapsed
US
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Carboximide derivative and medicines containing same
Assignee: Eisai Co Ltd
•
Filing: 1983-11-22
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Granted: 1986-01-28
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Expires: 2003-11-22
Abstract
Abstract A carboximide derivative represented by the general formula: ##STR1## wherein X is ##STR2## Z is alkyl, aralkyl, cycloalkyl, cycloalkylalkyl, alkenyl or arylalkenyl, and Y is a substituted or unsubstituted pyridyl, pyrimidyl or phenyl group, and a pharmaceutically acceptable acid addition salt thereof. The carboximide derivative and acid addition salt are useful for treating diabetes and also for depressing the central nervous system. The carboximide derivative may be produced by reacting a sodium alkoxide represented by the general formula: ##STR3## wherein X and Y have the same meanings as defined above, with Z.Hal wherein Hal is a halogen and Z has the same meaning as defined above.
Inventors
- 👤 Noriyasu Hirose
- 👤 Shigeru Souda
- 👤 Kazutoshi Miyake
- 👤 Shizuo Kuriyama
- 👤 Kazuyasu Usuki
- 👤 Yasuhiro Akiyama
- 👤 Naoko Nagaoka
- 👤 Hidetoshi Kawashima
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:51
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A61; A61P; A61P25/00; A61P3/00; A61P3/08; A61P3/10; C07D209/56; C07D209/58; C07D209/72; C07D209/76; C07D401/00; C07D401/02; C07D401/12; C07D403/00; C07D403/02; C07D403/12
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
86 words
A compound selected from the group consisting of a carboximide of the formula ##STR8## wherein X is ##STR9## Z is (1) alkyl of 1-10 carbon atoms, (2) benzyl in which the phenyl moiety is unsubstituted or is substituted by a halogen atom, (3) cyclohexyl, (4) cyclohexylmethyl, (5) allyl or (6) cinnamyl, and Y is pyridyl, pyrimidyl or phenyl, said groups being unsubstituted or substituted by at least one member selected from the group consisting of halogen and methyl, and a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
86 words
A compound selected from the group consisting of a carboximide of the formula ##STR8## wherein X is ##STR9## Z is (1) alkyl of 1-10 carbon atoms, (2) benzyl in which the phenyl moiety is unsubstituted or is substituted by a halogen atom, (3) cyclohexyl, (4) cyclohexylmethyl, (5) allyl or (6) cinnamyl, and Y is pyridyl, pyrimidyl or phenyl, said groups being unsubstituted or substituted by at least one member selected from the group consisting of halogen and methyl, and a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1, wherein X is ##STR10##
Claim 4
Dependent Claim
10 words
A compound according to claim 1, wherein Y is 2-pyridyl.
Claim 5
Dependent Claim
13 words
A compound according to claim 1, wherein Y is 2-chlorophenyl, 3-chlorophenyl or 4-chlorophenyl.
Claim 6
Dependent Claim
10 words
A compound according to claim 1, wherein Y is 2,4-dimethylphenyl.
Claim 7
Dependent Claim
10 words
A compound according to claim 1, wherein Y is α,α,α-trifluoro-3-tolyl.
Claim 8
Dependent Claim
17 words
A compound according to claim 1, wherein Z is a straight-chain alkyl group containing 1-10 carbon atoms.
Claim 9
Dependent Claim
17 words
A compound according to claim 7, wherein the straight-chain alkyl group is ethyl, n-butyl, n-octyl or n-decyl.
Claim 10
Dependent Claim
13 words
A compound according to claim 1, wherein Z is substituted or unsubstituted benzyl.
Claim 11
Dependent Claim
10 words
A compound according to claim 1, wherein Z is allyl.
Claim 12
Dependent Claim
10 words
A compound according to claim 1, wherein Z is cinnamyl.
Claim 13
Dependent Claim
27 words
A pharmaceutically acceptable acid addition salt according to claim 1, wherein the salt is a hydrochloride, hydrobromide, sulfate, maleate, fumarate, succinate, acetate, malonate, citrate, oxalate or benzoate.
Claim 14
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-ethoxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]-hept-5-ene-2,3-dicarboximide or the dimaleate thereof.
Claim 15
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-n-butoxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]-hept-5-ene-2,3-dicarboximide or the dimaleate thereof.
Claim 16
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-cyclohexylmethoxy-3-{4-(2-pyridyl)piperazine-1-yl}propyl]-endo-cis-bicyclo-[2.2.1]hept-5-ene-2,3-dicarboximide or the dimaleate thereof.
Claim 17
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-allyloxy-3-{4-(2,4-dimethylphenyl)piperazin-1-yl}propyl]-phthalimide or the oxalate thereof.
Claim 18
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-ethoxy-3-{4-(3-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]heptane-2,3-dicarboximide or the oxalate thereof.
Claim 19
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-ethoxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]-phthalimide or the dimaleate thereof.
Claim 20
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-benzyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the dimaleate thereof.
Claim 21
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-allyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.2]oct-5-ene-2,3-dicarboximide or the dimaleate thereof.
Claim 22
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-(4-chlorobenzyloxy)-3-{4-(2-pyrimidyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the maleate thereof.
Claim 23
Dependent Claim
14 words
A compound according to claim 1, which is N-[2-(n-octyloxy)-3-{4-(2-pyridyl)piperazin-1-yl}propyl]-cis-cyclohex-4-ene-1,2-dicarboximide or the 1.7 oxalate thereof.
Claim 24
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-n-butoxy-3-{4-(3-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the oxalate thereof.
Claim 25
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-ethoxy-3-{4-(3-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the oxalate thereof.
Claim 26
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-n-decycloxy-3-{4-(3-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the oxalate thereof.
Claim 27
Dependent Claim
14 words
A compound according to claim 1, which is N-[2-n-butoxy-3-{4-(3-chlorophenyl)piperazin-1-yl}propyl]-cis-cyclohex-4-ene-1,2-dicarboximide or the 1.1 oxalate thereof.
Claim 28
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-n-butoxy-3-{4-(4-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the oxalate thereof.
Claim 29
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-n-butoxy-3-{4-(2-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the dioxalate thereof.
Claim 30
Dependent Claim
14 words
A compound according to claim 1, which is N-[2-allyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]phthalimide or the 1.2 oxalate thereof.
Claim 31
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-benzyloxy-3-{4-(3-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the oxalate thereof.
Claim 32
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-cinnamyloxy-3-{4-(α,α,α-trifluoro-3-tolyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or the oxalate thereof.
Claim 33
Dependent Claim
14 words
A compound according to claim 1, which is N-[2-n-octyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]-cyclohexane-1,2-dicarboximide or the 1.7 oxalate thereof.
Claim 34
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-n-butoxy-3-{4-(3-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]heptane-2,3-dicarboximide or the oxalate thereof.
Claim 35
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-n-decyloxy-3-{4-(3-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]heptane-2,3-dicarboximide or the oxalate thereof.
Claim 36
Dependent Claim
13 words
A compound according to claim 1, which is N-[2-n-butoxy-3-{4-(4-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]heptane-2,3-dicarboximide or the oxalate thereof.
Claim 37
Dependent Claim
14 words
A compound according to claim 1, which is N-[2-n-butoxy-3-{4-(2-chlorophenyl)piperazin-1-yl}propyl]-endo-cis-bicyclo[2.2.1]heptane-2,3-dicarboximide or the 1.7 oxalate thereof.
Claim 38
Dependent Claim
106 words
A pharmaceutical composition for treating diabetes, or depressing the central nervous system, which comprises, as an active ingredient, and effective amount of a carboximide of the formula ##STR11## wherein X is ##STR12## Z is (1) alkyl of 1-10 carbon atoms, (2) benzyl in which the phenyl moiety is unsubstituted or is substituted by a halogen atom, (3) cyclohexyl, (4) cyclohexylmethyl, (5) allyl or (6) cinnamyl, and Y is pyridyl, pyrimidyl or phenyl, said groups being unsubstituted or substituted by at least one member selected from the group consisting of halogen and methyl, or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable carrier therefor.
Claim 39
Dependent Claim
106 words
A pharmaceutical composition for treating diabetes, or depressing the central nervous system, which comprises, as an active ingredient, and effective amount of a carboximide of the formula ##STR11## wherein X is ##STR12## Z is (1) alkyl of 1-10 carbon atoms, (2) benzyl in which the phenyl moiety is unsubstituted or is substituted by a halogen atom, (3) cyclohexyl, (4) cyclohexylmethyl, (5) allyl or (6) cinnamyl, and Y is pyridyl, pyrimidyl or phenyl, said groups being unsubstituted or substituted by at least one member selected from the group consisting of halogen and methyl, or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable carrier therefor.
Claim 40
Independent Claim
97 words
A method for treating diabetes which comprises administering to a patient suffering from diabetes a therapeutically effective amount of a carboximide of the formula: ##STR13## wherein X is ##STR14## Z is (1) alkyl of 1-10 carbon atoms, (2) benzyl in which the phenyl moiety is unsubstituted or is substituted by a halogen atom, (3) cyclohexyl, (4) cyclohexylmethyl, (5) allyl or (6) cinnamyl, and Y is pyridyl, pyrimidyl or phenyl, said groups being unsubstituted or substituted by at least one member selected from the group consisting of halogen and methyl, or a pharmaceutically acceptable acid addition salt thereof.
Claim 41
Independent Claim
97 words
A method for treating diabetes which comprises administering to a patient suffering from diabetes a therapeutically effective amount of a carboximide of the formula: ##STR13## wherein X is ##STR14## Z is (1) alkyl of 1-10 carbon atoms, (2) benzyl in which the phenyl moiety is unsubstituted or is substituted by a halogen atom, (3) cyclohexyl, (4) cyclohexylmethyl, (5) allyl or (6) cinnamyl, and Y is pyridyl, pyrimidyl or phenyl, said groups being unsubstituted or substituted by at least one member selected from the group consisting of halogen and methyl, or a pharmaceutically acceptable acid addition salt thereof.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-01-27 | 1989-07-29 | 1990-01-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-27 | 1993-07-29 | 1994-01-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-27 | 1997-07-29 | 1998-01-28 | $7700.00 | Window Closed / Lapsed |