US4479954A
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Piperazine substituted carboxamide derivatives, compositions and method of use
Assignee: Eisai Co Ltd
•
Filing: 1982-05-27
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Granted: 1984-10-30
•
Expires: 2002-05-27
Abstract
Abstract The carboximide derivatives of the formula: ##STR1## and pharmaceutically acceptable salts thereof; wherein X represents a group of the formula: ##STR2## Z represents a hydrogen atom or a group of the formula: ##STR3## wherein R represents an alkyl group, an aralkyl group, an aryl group, a cycloalkyl group, an alkenyl group, an arylalkenyl group, a pyridyl group or a substituted amino group; Y represents an alkyl group, an aralkyl group, an aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group or a benzothiazolyl group; and m represents an integer of 2 or 3 and processes for the production thereof. The derivatives and their salts possess hypoglycemic activity and are useful for treating diabetes.
Inventors
- 👤 Noriyasu Hirose
- 👤 Shigeru Souda
- 👤 Kazutoshi Miyake
- 👤 Shizuo Kuriyama
- 👤 Kazuyasu Usuki
- 👤 Yasuhiro Akiyama
- 👤 Naoko Sakabe
- 👤 Hidetoshi Kawashima
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:42
CPC Classifications
C; C07; C07D; C07D403/00; C07D403/02; C07D403/12; C07D401/00; A; A61; A61P; A61P3/00; A61P3/08; A61P3/10; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D209/56; C07D209/58; C07D209/72; C07D209/76; C07D401/02; C07D401/12; C07D401/14; C07D403/06; C07D403/14; C07D407/00; C07D407/02; C07D407/06; C07D417/00; C07D417/02; C07D417/12; C07D491/00; C07D491/02; C07D491/08
Claims Analysis
Total Claims: 59
Claim 1
Independent Claim
145 words
A carboximide derivative of the formula ##STR12## wherein X represents a group of the formula: ##STR13## Z represents a hydrogen atom or a group of the formula: ##STR14## wherein R represents (1) alkyl of 1 to 16 carbon atoms, (2) ##STR15## wherein n is an integer of 0-2 and A is H, methyl, methoxy or chlorine, (3) cyclopentyl, (4) cyclohexyl, (5) alkenyl of up to 16 carbon atoms, (6) cinnamoyl, (7) pyridyl or (8) ##STR16## wherein R 1 is alkyl of up to 10 carbon atoms or cyclohexyl, and Y represents (1) alkyl of 1-6 carbon atoms, (2) phenyl, (3) phenyl substituted by methyl, methoxy, chlorine or trifluoromethyl, (4) pyridyl, (5) pyridyl substituted by methyl, methoxy or chlorine, (6) pyrimidyl, (7) pyrimidyl substituted by methyl or methoxy or (8) benzothiazolyl; and m represents an integer of 2 or 3, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
145 words
A carboximide derivative of the formula ##STR12## wherein X represents a group of the formula: ##STR13## Z represents a hydrogen atom or a group of the formula: ##STR14## wherein R represents (1) alkyl of 1 to 16 carbon atoms, (2) ##STR15## wherein n is an integer of 0-2 and A is H, methyl, methoxy or chlorine, (3) cyclopentyl, (4) cyclohexyl, (5) alkenyl of up to 16 carbon atoms, (6) cinnamoyl, (7) pyridyl or (8) ##STR16## wherein R 1 is alkyl of up to 10 carbon atoms or cyclohexyl, and Y represents (1) alkyl of 1-6 carbon atoms, (2) phenyl, (3) phenyl substituted by methyl, methoxy, chlorine or trifluoromethyl, (4) pyridyl, (5) pyridyl substituted by methyl, methoxy or chlorine, (6) pyrimidyl, (7) pyrimidyl substituted by methyl or methoxy or (8) benzothiazolyl; and m represents an integer of 2 or 3, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
24 words
A carboximide derivative according to claim 1, wherein Y represents a substituted or unsubstituted pyridyl group as defined or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
24 words
A carboximide derivative according to claim 1, wherein Y represents a substituted or unsubstituted pyrimidyl group as defined or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
17 words
A carboximide derivative according to claim 1, wherein Y is 2-pyridyl or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
17 words
A carboximide derivative according to claim 1, wherein Y is 2-pyridimyl or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
17 words
A carboximide derivative according to claim 1, wherein X is ##STR17## or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
17 words
A carboximide derivative according to claim 1, wherein X is ##STR18## or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
17 words
A carboximide derivative according to claim 1, wherein X is ##STR19## or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
17 words
A carboximide derivative according to claim 1, wherein X is ##STR20## or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
17 words
A carboximide derivative according to claim 1, wherein X is ##STR21## or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR22## and Y is 2-pyridyl, or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR23## and Y is 2-pyrimidyl, or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR24## and Y is 2-pyridyl, or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR25## and Y is 2-pyrimidyl, or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR26## and Y is 2-pyridyl, or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR27## and Y is 2-pyrimidyl, or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR28## and Y is 2-pyridyl, or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR29## and Y is 2-pyrimidyl, or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR30## and Y is 2-pyridyl, or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
21 words
A carboximide derivative according to claim 1, wherein X is ##STR31## and Y is 2-pyrimidyl, or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
19 words
A carboximide derivative according to claim 1, wherein Z represents a hydrogen atom, or a pharmaceutically acceptable salt thereof.
Claim 23
Dependent Claim
30 words
A carboximide derivative according to claim 1, wherein Z represents a group of the formula ##STR32## wherein R is as defined in claim 48 or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim
6 words
N-[2-Cyclohexylcarbonyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]endo-cis-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide or its pharmaceutically acceptable salt.
Claim 25
Dependent Claim
6 words
N-[2-Cyclohexylcarbonyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]endo-cis-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide or its pharmaceutically acceptable salt.
Claim 26
Dependent Claim
6 words
N-[2-n-Caproyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 27
Dependent Claim
6 words
N-[2-n-Caproyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 28
Dependent Claim
6 words
N-[2-Propionyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]phthalimide or its pharmaceutically acceptable salt.
Claim 29
Dependent Claim
6 words
N-[2-Propionyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]phthalimide or its pharmaceutically acceptable salt.
Claim 30
Dependent Claim
6 words
N-[2-Nicotinyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]phthalimide or its pharmaceutically acceptable salt.
Claim 31
Dependent Claim
6 words
N-[2-Nicotinyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]phthalimide or its pharmaceutically acceptable salt.
Claim 32
Dependent Claim
6 words
N-[2-(trans-2-Nonenoyloxy)-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 33
Dependent Claim
6 words
N-[2-(trans-2-Nonenoyloxy)-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 34
Dependent Claim
6 words
N-[2-Palmitoyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 35
Dependent Claim
6 words
N-[2-Palmitoyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 36
Dependent Claim
6 words
N-[2-Cyclohexylcarbonyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 37
Dependent Claim
6 words
N-[2-Cyclohexylcarbonyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 38
Dependent Claim
6 words
N-[2-n-Caproyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]phthalimide or its pharmaceutically acceptable salt.
Claim 39
Dependent Claim
6 words
N-[2-n-Caproyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]phthalimide or its pharmaceutically acceptable salt.
Claim 40
Dependent Claim
6 words
N-[2-n-Octanoyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]succinimide or its pharmaceutically acceptable salt.
Claim 41
Dependent Claim
6 words
N-[2-n-Octanoyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]succinimide or its pharmaceutically acceptable salt.
Claim 42
Dependent Claim
6 words
N-[2-Cyclohexylcarbonyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]succinimide or its pharmaceutically acceptable salt.
Claim 43
Dependent Claim
6 words
N-[2-Cyclohexylcarbonyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]succinimide or its pharmaceutically acceptable salt.
Claim 44
Dependent Claim
6 words
N-[2-n-Decanoyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 45
Dependent Claim
6 words
N-[2-n-Decanoyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 46
Dependent Claim
6 words
N-[2-Nicotinyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 47
Dependent Claim
6 words
N-[2-Nicotinyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 48
Dependent Claim
6 words
N-[2-Isobutyryloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 49
Dependent Claim
6 words
N-[2-Isobutyryloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 50
Dependent Claim
6 words
N-[2-n-Octanoyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 51
Dependent Claim
6 words
N-[2-n-Octanoyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohex-4-ene-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 52
Dependent Claim
6 words
N-[2-Cyclohexylcarbonyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohexane-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 53
Dependent Claim
6 words
N-[2-Cyclohexylcarbonyloxy-3-{4-(2-pyridyl)piperazin-1-yl}propyl]cis-cyclohexane-1,2-dicarboximide or its pharmaceutically acceptable salt.
Claim 54
Dependent Claim
32 words
A pharmaceutical composition for treating diabetes which comprises an effective amount of a carboximide derivative as defined in claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier therefor.
Claim 55
Dependent Claim
22 words
A pharmaceutical composition for treating diabetes as claimed in claim 38, wherein Y represents a substituted or unsubstituted pyridyl group as defined.
Claim 56
Dependent Claim
15 words
A pharmaceutical composition for treating diabetes as claimed in claim 38 wherein Y is 2-pyridyl.
Claim 57
Dependent Claim
19 words
A pharmaceutical composition for treating diabetes as claimed in claim 38 wherein X is ##STR33## and Y is 2-pyridyl.
Claim 58
Dependent Claim
22 words
A pharmaceutical composition for treating diabetes as claimed in claim 38 wherein Z is a group of the formula ##STR34## as defined.
Claim 59
Dependent Claim
31 words
A method for treating diabetes which comprises administering to a patient suffering from diabetes an effective amount of a carboximide derivative or a pharmaceutically acceptable salt thereof according to claim 1.
References Cited (Backward Citations)
US3126395A
Cited
US3126396A
Cited
US3198798A
Cited
US3563986A
Cited
US3579524A
Cited
US3850922A
Cited
US3936449A
Cited
US3980667A
Cited
US4018767A
Cited
US4070465A
Cited
US4139533A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-30 | 1988-04-30 | 1988-10-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-30 | 1992-04-30 | 1992-10-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-30 | 1996-04-30 | 1996-10-30 | $7700.00 | Window Closed / Lapsed |