US4533668A
Expired / Lapsed
US
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Antihyperglycemic moranoline derivatives
Assignee: Nippon Shinyaku Co Ltd
•
Filing: 1979-04-27
•
Granted: 1985-08-06
•
Expires: 1999-04-27
Abstract
Abstract N-aralkylmoranoline and N-aralkenylmoranoline, and their pharmaceutical acceptable non-toxic acid addition salts thereof, pharmaceutical compositions containing the same and methods of inhibiting the increase in blood sugar level by administration of the same.
Inventors
- 👤 Shingo Matsumura
- 👤 Hiroshi Enomoto
- 👤 Yoshiaki Aoyagi
- 👤 Yoshiaki Yoshikuni
- 👤 Kohei Kura
- 👤 Masahiro Yagi
- 👤 Ichiro Shirahase
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 05:18
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
85 words
An N-substituted moranoline of the formula ##STR86## wherein X is divalent alkyl or alkenyl of 3 to 6 carbon atoms, Y is hydrogen, methyl or ##STR87## and Z is ##STR88## or thienyl, wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, halogen, lower alkyl, lower alkoxy, hydroxyl, trihalomethyl, phenoxy, diloweralkylamino, cyano, carboxyl, carbamoyl or carboloweralkoxy, R 5 is hydrogen or hydroxymethyl and R 6 is hydrogen, methyl, ethyl or methoxyethyl, or a pharmaceutically acceptable nontoxic acid addition salt thereof.
Claim 2
Dependent Claim
85 words
An N-substituted moranoline of the formula ##STR86## wherein X is divalent alkyl or alkenyl of 3 to 6 carbon atoms, Y is hydrogen, methyl or ##STR87## and Z is ##STR88## or thienyl, wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, halogen, lower alkyl, lower alkoxy, hydroxyl, trihalomethyl, phenoxy, diloweralkylamino, cyano, carboxyl, carbamoyl or carboloweralkoxy, R 5 is hydrogen or hydroxymethyl and R 6 is hydrogen, methyl, ethyl or methoxyethyl, or a pharmaceutically acceptable nontoxic acid addition salt thereof.
Claim 3
Dependent Claim
22 words
The moranoline derivative according to claim 1 of the formula: ##STR89## wherein X is divalent C 3 alkyl or C 3 alkenyl.
Claim 4
Dependent Claim
49 words
The moranoline derivative according to claim of the formula ##STR90## wherein R is hydrogen or phenyl and X is divalent alkyl or alkenyl of 4 or 5 carbon atoms when R is hydrogen or X is divalent alkenyl of 3, 4 or 5 carbon atoms when R is phenyl.
Claim 5
Dependent Claim
65 words
The moranoline derivative according to claim 1 of the formula ##STR91## wherein X is divalent alkyl or alkenyl of 3 to 6 carbon atoms, Y is hydrogen, methyl or ##STR92## and Z is ##STR93## or thienyl, wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, halogen, lower alkyl, lower alkoxy, hydroxyl, trihalomethyl, phenoxy, diloweralkylamino, cyano, carboxyl, carbamoyl or carboloweralkoxy.
Claim 6
Dependent Claim
32 words
The moranoline derivative according to claim 1, of the formula: ##STR94## wherein Y is hydrogen or methyl, R 5 is hydrogen or hydroxymethyl and R 6 is hydrogen, methyl, ethyl or methoxyethyl.
Claim 7
Dependent Claim
10 words
The moranoline derivative according to claim 2, which is ##STR95##
Claim 8
Dependent Claim
10 words
The moranoline derivative according to claim 2, which is ##STR96##
Claim 9
Dependent Claim
9 words
The moranoline derivative according to claim 3, wherein ##STR97##
Claim 10
Dependent Claim
9 words
The moranoline derivative according to claim 3, wherein ##STR98##
Claim 11
Dependent Claim
9 words
The moranoline derivative according to claim 3, wherein ##STR99##
Claim 12
Dependent Claim
9 words
The moranoline derivative according to claim 3, wherein ##STR100##
Claim 13
Dependent Claim
9 words
The moranoline derivative according to claim 3, wherein ##STR101##
Claim 14
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR102##
Claim 15
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR103##
Claim 16
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR104##
Claim 17
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR105##
Claim 18
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR106##
Claim 19
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR107##
Claim 20
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR108##
Claim 21
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR109##
Claim 22
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR110##
Claim 23
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR111##
Claim 24
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR112##
Claim 25
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR113##
Claim 26
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR114##
Claim 27
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR115##
Claim 28
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR116##
Claim 29
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR117##
Claim 30
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR118##
Claim 31
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR119##
Claim 32
Dependent Claim
9 words
The moranoline derivative according to claim 4, wherein ##STR120##
Claim 33
Dependent Claim
10 words
The moranoline derivative according to claim 5, which is ##STR121##
Claim 34
Dependent Claim
10 words
The moranoline derivative according to claim 5, which is ##STR122##
Claim 35
Dependent Claim
10 words
The moranoline derivative according to claim 5, which is ##STR123##
Claim 36
Dependent Claim
10 words
The moranoline derivative according to claim 5, which is ##STR124##
Claim 37
Dependent Claim
10 words
The moranoline derivative according to claim 5, which is ##STR125##
Claim 38
Dependent Claim
10 words
The moranoline derivative according to claim 5, which is ##STR126##
Claim 39
Dependent Claim
10 words
The moranoline derivative according to claim 5, which is ##STR127##
Claim 40
Dependent Claim
34 words
A composition for prophylaxis and treatment of hyperglycemic symptoms, comprising an amount of a compound of claim 1 effective to inhibit the increase of blood sugar and a pharmaceutically acceptable inert diluent carrier therefor.
Claim 41
Dependent Claim
37 words
A method for the prophylaxis or treatment of hyperglycemic symptoms, which comprises administering to a human or animal in need thereof an amount of a compound of claim 1 effective to inhibit the increase of blood sugar.
Claim 42
Dependent Claim
56 words
A compound of the formula ##STR128## wherein X is divalent alkyl of 3 to 6 carbon atoms, Y is hydrogen or methyl and Z is ##STR129## wherein R 3 and R 4 are independently hydrogen, halogen, lower alkyl, lower alkoxy, hydroxyl, trihalomethyl, diloweralkylamino, cyano, carboxyl or carboloweralkoxy, or a pharmaceutically acceptable non-toxic acid addition salt thereof.
Claim 43
Dependent Claim
56 words
A compound of the formula ##STR128## wherein X is divalent alkyl of 3 to 6 carbon atoms, Y is hydrogen or methyl and Z is ##STR129## wherein R 3 and R 4 are independently hydrogen, halogen, lower alkyl, lower alkoxy, hydroxyl, trihalomethyl, diloweralkylamino, cyano, carboxyl or carboloweralkoxy, or a pharmaceutically acceptable non-toxic acid addition salt thereof.
References Cited (Backward Citations)
US4137231A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-08-05 | 1989-02-04 | 1989-08-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-05 | 1993-02-04 | 1993-08-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-05 | 1997-02-04 | 1997-08-06 | $7700.00 | Window Closed / Lapsed |