Patent US5498775A successfully refreshed from Google Patents.
US5498775A
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Polyanionic benzylglycosides as inhibitors of smooth muscle cell proliferation
Assignee: Wyeth LLC
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Filing: 1994-11-07
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Granted: 1996-03-12
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Expires: 2014-11-07
Abstract
Abstract This invention relates to the use of polyanionic benzylglycosides as smooth muscle cell proliferation inhibitors and as therapeutic compositions for treating diseases and conditions which are characterized by excessive smooth muscle proliferation, such as restenosis. The compounds of this invention are those of formula I ##STR1## wherein each of R 1 , R 2 , R 3 , and R 4 are, independently, H, SO 3 M, or ##STR2## and each oligosaccharide group contains 1 to 3 sugar groups; M is lithium, sodium, potassium, or ammonium; n is 1 or 2; X is a halogen, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; Y is carbonyl or sulfonyl; Z is alkyl from 1 to 12 carbon atoms, ##STR3## and X is as defined above; or a pharmaceutically acceptable salt thereof.
Inventors
- 👤 Sarah T. A. Novak
- 👤 Richard M. Soll
- 👤 John W. Ellingboe
- 👤 Thomas T. Nguyen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 10:13
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/22; A; A61; A61P; A61P43/00; A61P9/00
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
112 words
A compound of formula I ##STR11## wherein each of R 1 , R 2 , R 3 , and R 4 are, independently, H, SO 3 M, or a sugar group having the structure: ##STR12## and each oligosaccharide group of the structure ##STR13## contains from 1 to 3 sugar groups; M is lithium, sodium, potassium, or ammonium; n is 1 or 2; X is a hydrogen, halogen, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; Y is carbonyl or sulfonyl; Z is alkyl having from 1 to 12 carbon atoms, ##STR14## and X is as defined above; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
112 words
A compound of formula I ##STR11## wherein each of R 1 , R 2 , R 3 , and R 4 are, independently, H, SO 3 M, or a sugar group having the structure: ##STR12## and each oligosaccharide group of the structure ##STR13## contains from 1 to 3 sugar groups; M is lithium, sodium, potassium, or ammonium; n is 1 or 2; X is a hydrogen, halogen, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; Y is carbonyl or sulfonyl; Z is alkyl having from 1 to 12 carbon atoms, ##STR14## and X is as defined above; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
102 words
A compound according to claim 1 of formula I ##STR15## wherein each of R 1 , R 2 , R 3 , and R 4 are, independently, H, SO 3 M, or ##STR16## and each oligosaccharide group of the structure ##STR17## contains 1 or 2 sugar groups; M is lithium, sodium, potassium, or ammonium; n is 1 or 2; X is a hydrogen, halogen, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having to 6 carbon atoms; Y is carbonyl or sulfonyl; Z is alkyl having from 1 to 12 carbon atoms, ##STR18## or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
18 words
A compound according to claim 2 which is dodecanedioic acid bis{[2-methyl-5-(hepta-O-sulfato-β-D-cellobiosyloxymethyl)phenyl]amide}tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
18 words
A compound according to claim 2 which is 2 N,N'-bis[5-(hepta-O-sulfato-β-D-cellobiosyloxymethyl)-2-methylphenyl]-terephthalamide tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
18 words
A compound according to claim 2 which is biphenyl-4,4'-dicarboxylic acid bis{[5-(hepta-O-sulfato-β-D-cellobiosyloxymethyl)-2-methylphenyl]amide}tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
17 words
A compound according to claim 2 which is N,N'-bis[5-(hepta-O-sulfato-β-D-cellobiosyloxymethyl)-2-methylphenyl]isophthalamide tetradecasodium salt; or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
19 words
A compound according to claim 2 which is decanedioic acid bis{[3,5-bis(hepta-0-sulfato-β-D-cellobiosyloxymethyl)phenyl]amide octacosasodium salt or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
18 words
A compound according to claim 2 which is biphenyl-4,4'-dicarboxylic acid bis{[3,5-bis(hepta-O-sulfato-β-D-cellobiosyloxymethyl)phenyl]amide}octacosa-sodium salt or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
18 words
A compound according to claim 2 which is biphenyl-4,4'-dicarboxylic acid bis{[3,5-bis-(hepta-O-sulfato-β-D-lactosyloxymethyl)phenyl]amide}octacosasodium salt or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
18 words
A compound according to claim 2 which is biphenyl-4,4'-dicarboxylic acid bis{[3,5-(bis-(hepta-O-sulfato-β-D-maltosyloxymethyl)phenyl]amide}octacosasodium salt or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
18 words
A compound according to claim 2 which is biphenyl-4,4'-dicarboxylic acid bis{[3,5-bis-(tetra-O-sulfato-β-D-glucosyloxymethyl)phenyl]amide}hexadecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
18 words
A compound according to claim 2 which is biphenyl-4,4'-dicarboxylic acid bis{[2-chloro-5-(hepta-O-sulfato-β-D-cellobiosyloxymethyl)phenyl]amide}tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
19 words
A compound according to claim 2 which is biphenyl-4,4'-dicarboxylic acid bis{[4-chloro- 2-(hepta-O-sulfato-β-D-cellobiosyloxymethyl)phenyl]amide}tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
17 words
A compound according to claim 2 which is N,N'-bis[3,5-bis(hepta-O-sulfato-β-D-cellobiosyloxymethyl)phenyl]succinamide octacosasodium salt or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
17 words
A compound according to claim 2 which is N,N'-bis[3,5-bis(hepta-O-sulfato-β-D-cellobiosyloxymethyl)phenyl]terephthalamide octacosasodium salt or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
18 words
A compound according to claim 2 which is biphenyl-4,4'-disulfonic acid bis{[2-methyl-5-(hepta-O-sulfato-β-D-cellobiosyloxymethyl)phenyl]amide}tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
17 words
A compound according to claim 2 which is N,N'-bis[2-methyl-5(2,3,4,6-tetra-O-sulfato-β-D-glucopyranosyloxymethyl)phenyl]succinamide octasodium salt or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
17 words
A compound according to claim 2 which is 3,3'-[1,3-ureido]-bis{N-[2-methyl-5-(hepta-O-sulfato-β-D-maltosyloxymethyl)phenyl]}benzamide tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
17 words
A compound according to claim 2 which is 3,3'-(N,N'-ureido)bis-({N-2-chloro-5-(hepta-O-sulfato-β-D-cellobiosyloxymethyl)phenyl]}benzamide) tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
16 words
A compound according to claim.2 which is N,N'-bis{3-[2-methyl-5-(hepta-O-sulfato-β-D-maltosyloxymethyl)phenylcarbamoyl]phenyl}isophthalamide tetradecasodium salt or a pharmaceutically acceptable salt thereof.
Claim 22
Independent Claim
140 words
A method of treating a human suffering from a condition which is characterized by excessive smooth muscle proliferation, the method comprising administering to the human an effective amount of the compound formula I ##STR19## wherein each of R 1 , R 2 , R 3 , and R 4 are, independently, H, SO 3 M, or a sugar group having the structure: ##STR20## and each oligosaccharide group of the structure ##STR21## contains from 1 to 3 sugar groups; M is lithium, sodium, potassium, or ammonium; n is 1 or 2; X is a hydrogen, halogen, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; Y is carbonyl or sulfonyl; Z is alkyl having from 1 to 12 carbon atoms, ##STR22## and X is as defined above; or a pharmaceutically acceptable salt thereof.
Claim 23
Independent Claim
140 words
A method of treating a human suffering from a condition which is characterized by excessive smooth muscle proliferation, the method comprising administering to the human an effective amount of the compound formula I ##STR19## wherein each of R 1 , R 2 , R 3 , and R 4 are, independently, H, SO 3 M, or a sugar group having the structure: ##STR20## and each oligosaccharide group of the structure ##STR21## contains from 1 to 3 sugar groups; M is lithium, sodium, potassium, or ammonium; n is 1 or 2; X is a hydrogen, halogen, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; Y is carbonyl or sulfonyl; Z is alkyl having from 1 to 12 carbon atoms, ##STR22## and X is as defined above; or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim
20 words
The method of claim 21 wherein the disease or condition which is characterized by excessive smooth muscle proliferation is restenosis.
Claim 25
Dependent Claim
120 words
A pharmaceutical composition comprising an effective amount of a compound of formula I ##STR23## wherein each of R 1 , R 2 , R 3 , and R 4 are, independently, H, SO 3 M, or a sugar group having the structure: ##STR24## and each oligosaccharide group of the structure ##STR25## contains from 1 to 3 sugar groups; M is lithium, sodium, potassium, or ammonium; n is 1 or 2; X is a hydrogen, halogen, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; Y is carbonyl or sulfonyl; Z is alkyl having from 1 to 12 carbon atoms, ##STR26## and X is as defined above; or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
120 words
A pharmaceutical composition comprising an effective amount of a compound of formula I ##STR23## wherein each of R 1 , R 2 , R 3 , and R 4 are, independently, H, SO 3 M, or a sugar group having the structure: ##STR24## and each oligosaccharide group of the structure ##STR25## contains from 1 to 3 sugar groups; M is lithium, sodium, potassium, or ammonium; n is 1 or 2; X is a hydrogen, halogen, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; Y is carbonyl or sulfonyl; Z is alkyl having from 1 to 12 carbon atoms, ##STR26## and X is as defined above; or a pharmaceutically acceptable salt thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1999-03-12 | 1999-09-11 | 2000-03-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-03-12 | 2003-09-11 | 2004-03-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-03-12 | 2007-09-11 | 2008-03-12 | $7700.00 | Window Closed / Lapsed |