US4402948A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Steroid glycoside compounds and methods of use
Assignee: Nippon Shinyaku Co Ltd
•
Filing: 1981-01-23
•
Granted: 1983-09-06
•
Expires: 2001-01-23
Abstract
Abstract Oxygenated sterylglycoside derivatives of the formula (I) wherein R 1 , R 2 , R 3 and R 4 are the same or different and each is hydrogen or lower alkanoyl, Y is ##STR1## and R 5 is 4-methylpentyl, 3-ethyl-4-methylpentyl or 3-ethyl-4-methyl-1-pentenyl are useful for their hemostatic and capillary stabilizing effects.
Inventors
- 👤 Shingo Matsumura
- 👤 Hiroshi Enomoto
- 👤 Koji Kitaguchi
- 👤 Masakuni Ozaki
- 👤 Masahiko Kitano
- 👤 Toshihiro Okamura
- 👤 Haruo Tanaka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 22:01
CPC Classifications
C; C07; C07J; C07J17/00; C07J17/005; A; A61; A61P; A61P7/00; A61P7/04; A61P9/00; A61P9/14
Claims Analysis
Total Claims: 76
Claim 1
Independent Claim
44 words
An oxygenated sterylglycoside derivative of the formula (I): ##STR19## wherein R 1 , R 2 , R 3 and R 4 are the same or different and each is hydrogen or lower alkanoyl, Y is ##STR20## and R 5 is 4-methylpentyl, 3-ethyl-4-methylpentyl or 3-ethyl-4-methyl-1-pentenyl.
Claim 2
Dependent Claim
44 words
An oxygenated sterylglycoside derivative of the formula (I): ##STR19## wherein R 1 , R 2 , R 3 and R 4 are the same or different and each is hydrogen or lower alkanoyl, Y is ##STR20## and R 5 is 4-methylpentyl, 3-ethyl-4-methylpentyl or 3-ethyl-4-methyl-1-pentenyl.
Claim 3
Dependent Claim
24 words
A compound according to claim 1 wherein the configuration of the sterol side chain in formula (I) is the same as that of β-sitosterol.
Claim 4
Dependent Claim
24 words
A compound according to claim 1 wherein the configuration of the sterol side chain in formula (I) is the same as that of stigmasterol.
Claim 5
Dependent Claim
24 words
A compound according to claim 1 wherein the configuration of the sterol side chain in formula (I) is the same as that of cholesterol.
Claim 6
Dependent Claim
23 words
A compound according to claim 1 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 7
Dependent Claim
23 words
A compound according to claim 2 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 8
Dependent Claim
25 words
A compound according to claim 3 or 4 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 9
Dependent Claim
9 words
The compound according to claim 1 which is (7-Ketocholesteryl)-2,3,4,6-tetra-0-acetyl-β-D-glucopyranoside.
Claim 10
Dependent Claim
9 words
The compound according to claim 1 which is (7-Ketocholesteryl)-β-D-glucopyranoside.
Claim 11
Dependent Claim
9 words
The compound according to claim 1 which is (7-Hydroxycholesteryl)-2,3,4,6-tetra-0-acetyl-β-D-glucopyranoside.
Claim 12
Dependent Claim
9 words
The compound according to claim 1 which is (7-Hydroxycholesteryl)-β-D-glucopyranoside.
Claim 13
Dependent Claim
73 words
A pharmaceutical composition useful for effecting hemostatic and capillary stabilizing effects which comprises a hemostatically effective amount or a capillary stabilizing effective amount of a compound of the formula (I): ##STR21## wherein R 1 , R 2 , R 3 and R 4 are the same or different and each is hydrogen or lower alkanoyl, Y is ##STR22## and R 5 is 4-methylpentyl, 3-ethyl-4-methylpentyl or 3-ethyl-4-methyl-1-pentenyl, in combination with a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
73 words
A pharmaceutical composition useful for effecting hemostatic and capillary stabilizing effects which comprises a hemostatically effective amount or a capillary stabilizing effective amount of a compound of the formula (I): ##STR21## wherein R 1 , R 2 , R 3 and R 4 are the same or different and each is hydrogen or lower alkanoyl, Y is ##STR22## and R 5 is 4-methylpentyl, 3-ethyl-4-methylpentyl or 3-ethyl-4-methyl-1-pentenyl, in combination with a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
24 words
A composition according to claim 12 wherein the configuration of the sterol side chain in formula (I) is the same as that of β-sitosterol.
Claim 16
Dependent Claim
24 words
A composition according to claim 12 wherein the configuration of the sterol side chain in formula (I) is the same as that of stigmasterol.
Claim 17
Dependent Claim
24 words
A composition according to claim 12 wherein the configuration of the sterol side chain in formula (I) is the same as that of cholesterol.
Claim 18
Dependent Claim
23 words
A composition according to claim 12 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 19
Dependent Claim
23 words
A composition according to claim 13 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 20
Dependent Claim
25 words
A composition according to claim 14 or 15 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 21
Dependent Claim
11 words
A composition according to claim 12 wherein the compound is (7-Ketocholesteryl)-2,3,4,6-tetra-0-acetyl-β-D-glucopyranoside.
Claim 22
Dependent Claim
12 words
A composition according to claim 12 wherein the compound is (7-Ketocholesteryl)-62 -D-glucopyranoside.
Claim 23
Dependent Claim
11 words
A composition according to claim 12 wherein the compound is (7-Hydroxycholesteryl)-2,3,4,6-tetra-0-acetyl-β-D-glucopyranoside.
Claim 24
Dependent Claim
11 words
A composition according to claim 12 wherein the compound is (7-Hydroxycholesteryl)-β-D-glucopyranoside.
Claim 25
Dependent Claim
10 words
A composition according to claim 12 in oral administration form.
Claim 26
Dependent Claim
14 words
A composition according to claim 12 in a form suitable for administration by injection.
Claim 27
Independent Claim
78 words
A method useful for effecting hemostatic or capillary stabilizing effects which comprises administering to one in need thereof, a hemostatically effective amount or a capillary stabilizing effective amount of a compound of the formula (I): ##STR23## wherein R 1 , R 2 , R 3 and R 4 are the same or different and each is hydrogen or lower alkanoyl, Y is ##STR24## and R 5 is 4-methylpentyl, 3-ethyl-4-methylpentyl or 3-ethyl-4-methyl-1-pentenyl, in combination with a pharmaceutically acceptable carrier.
Claim 28
Independent Claim
78 words
A method useful for effecting hemostatic or capillary stabilizing effects which comprises administering to one in need thereof, a hemostatically effective amount or a capillary stabilizing effective amount of a compound of the formula (I): ##STR23## wherein R 1 , R 2 , R 3 and R 4 are the same or different and each is hydrogen or lower alkanoyl, Y is ##STR24## and R 5 is 4-methylpentyl, 3-ethyl-4-methylpentyl or 3-ethyl-4-methyl-1-pentenyl, in combination with a pharmaceutically acceptable carrier.
Claim 29
Dependent Claim
24 words
A method according to claim 25 wherein the configuration of the sterol side chain in formula (I) is the same as that of β-sitosterol.
Claim 30
Dependent Claim
24 words
A method according to claim 25 wherein the configuration of the sterol side chain in formula (I) is the same as that of stigmasterol.
Claim 31
Dependent Claim
24 words
A method according to claim 25 wherein the configuration of the sterol side chain in formula (I) is the same as that of cholesterol.
Claim 32
Dependent Claim
23 words
A method according to claim 25 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 33
Dependent Claim
23 words
A method according to claim 26 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 34
Dependent Claim
25 words
A method according to claim 27 or 28 wherein the configuration of the sugar moiety in formula (I) is the same as that of β-D-glucose.
Claim 35
Dependent Claim
11 words
A method according to claim 25 wherein the compound is (7-Ketocholesteryl)-2,3,4,6-tetra-0-acetyl-β-D-glucopyranoside.
Claim 36
Dependent Claim
11 words
A method according to claim 25 wherein the compound is (7-Ketocholesteryl)-β-D-glucopyranoside.
Claim 37
Dependent Claim
11 words
A method according to claim 25 wherein the compound is (7-Hydroxycholesteryl)-2,3,4,6-tetra-0-acetyl-β-D-glucopyranoside.
Claim 38
Dependent Claim
11 words
A method according to claim 25 wherein the compound is (7-Hydroxycholesteryl)-β-D-glucopyranoside.
Claim 39
Dependent Claim
11 words
A method according to claim 25 wherein the administration is oral.
Claim 40
Dependent Claim
18 words
A method according to claim 25 wherei the compound is in a form suitable for administration by injection.
Claim 41
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 4-methylpentyl.
Claim 42
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 3-ethyl-4-methylpentyl.
Claim 43
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 3-ethyl-4-methyl-1-pentyl.
Claim 44
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 4-methylpentyl.
Claim 45
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 3-ethyl-4-methylpentyl.
Claim 46
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 3-ethyl-4-methyl-1-pentenyl.
Claim 47
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR25## and R 5 is 4-methylpentyl.
Claim 48
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR26## and R 5 is 3-ethyl-4-methylpentyl.
Claim 49
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR27## and R 5 is 3-ethyl-4-methyl-1-pentenyl.
Claim 50
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR28## and R 5 is 4-methylpentyl.
Claim 51
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR29## and R 5 is 3-ethyl-4-methylpentyl.
Claim 52
Dependent Claim
29 words
The compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR30## and R 5 is 3-ethyl-4-methyl-1-pentenyl.
Claim 53
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 4-methylpentyl.
Claim 54
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 3-ethyl-4-methylpentyl.
Claim 55
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 3-ethyl-4-methyl-1-pentyl.
Claim 56
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 4-methylpentyl.
Claim 57
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 3-ethyl-4-methylpentyl.
Claim 58
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 3-ethyl-4-methyl-1-pentenyl.
Claim 59
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR31## and R 5 is 4-methylpentyl.
Claim 60
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR32## and R 5 is 3-ethyl-4-methylpentyl.
Claim 61
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR33## and R 5 is 3-ethyl-4-methyl-1-pentenyl.
Claim 62
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR34## and R 5 is 4-methylpentyl.
Claim 63
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR35## and R 5 is 3-ethyl-4-methylpentyl.
Claim 64
Dependent Claim
29 words
A composition according to claim 12 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR36## and R 5 is 3-ethyl-4-methyl-1-pentenyl.
Claim 65
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 4-methylpentyl.
Claim 66
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 3-ethyl-4-methylpentyl.
Claim 67
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is >═O and R 5 is 3-ethyl-4-methyl-1-pentyl.
Claim 68
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 4-methylpentyl.
Claim 69
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 3-ethyl-4-methylpentyl.
Claim 70
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is >═O and R 5 is 3-ethyl-4-methyl-1-pentenyl.
Claim 71
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR37## and R 5 is 4-methylpentyl.
Claim 72
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR38## and R 5 is 3-ethyl-4-methylpentyl.
Claim 73
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each acetyl, Y is ##STR39## and R 5 is 3-ethyl-4-methyl-1-pentenyl.
Claim 74
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR40## and R 5 is 4-methylpentyl.
Claim 75
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR41## and R 5 is 3-ethyl-4-methylpentyl.
Claim 76
Dependent Claim
29 words
A method according to claim 25 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, Y is ##STR42## and R 5 is 3-ethyl-4-methyl-1-pentenyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-09-05 | 1987-03-07 | 1987-09-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-09-05 | 1991-03-07 | 1991-09-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-09-05 | 1995-03-07 | 1995-09-06 | $7700.00 | Window Closed / Lapsed |