Patent US4071478A successfully refreshed from Google Patents.
US4071478A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Controlled partially cross-linked 3,3-ionenes
Assignee: Merck and Co Inc
•
Filing: 1976-06-07
•
Granted: 1978-01-31
•
Expires: 1996-06-07
Abstract
Abstract The invention disclosed herein relates to novel partially cross-linked, fully quaternized poly-[(methylimino)trimethylene] polymers wherein a minor proportion (1% to 20%) of the nitrogen atoms in adjacent poly-[(methylimino)trimethylene] linear chains are, by quaternization, joined through trimethylene or 2-hydroxy-trimethylene bridges, the non-cross-linked nitrogens in the said linear chains being fully quaternized with lower alkyl or trialkylammoniopropyl groupings; and to the novel process for preparing these partially cross-linked, fully quaternized polymers which comprises reacting poly-[(methylimino)trimethylene] with 0.01 to 0.2 equivalents of 1,3-dihalo-propane or 1,3-dihalo-2-hydroxypropane per equivalent of tertiary amine in said poly-[(methylimino)trimethylene], and subsequently reacting the resulting product with excess alkyl halide or 3-halopropyltrialkylammonium halide. These partially cross-linked fully quaternized poly-[(methylimino) trimethylene] polymers are useful as highly-efficient bile acid sequestrants.
Inventors
- 👤 Tsung-Ying Shen
- 👤 Arthur F. Wagner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 23:17
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/02; C08G73/0206; C08G73/0213; C08G73/0226
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
108 words
The process which comprises reacting a poly-[(methylimino)trimethylene] polymer with about 1% to 20% of the stoichiometric equivalent (based on the tertiary amine content of the polymer) of 1,3-dihalopropane or 2-hydroxy-1,3-dihalopropane, thereby forming a partially (1% to 20%) cross-linked, partially-quaternized polymeric mixture, wherein nitrogen atoms in adjacent poly-[(methylimino)trimethylene] linear chains are, by quaternization, joined through trimethylene or 2-hydroxy-trimthylene bridges; and reacting the said partially cross-linked, partially quaternized polymeric mixture with an excess of alkyl halide or trialkylammoniopropyl halide, thereby quaternizing any residual tertiary amine groupings present in the said polymeric mixture to form the corresponding substantially completely quaternized, 1% to 20% (1,3-trimethylene or 2-hydroxy-1,3-trimethylene)-cross-linked, poly-[(alkyl-methyliminio)trimethylene halide] or poly-[{methyl-(3-trialkylammoniopropyl)iminio}trimethylene dihalide].
Claim 2
Dependent Claim
108 words
The process which comprises reacting a poly-[(methylimino)trimethylene] polymer with about 1% to 20% of the stoichiometric equivalent (based on the tertiary amine content of the polymer) of 1,3-dihalopropane or 2-hydroxy-1,3-dihalopropane, thereby forming a partially (1% to 20%) cross-linked, partially-quaternized polymeric mixture, wherein nitrogen atoms in adjacent poly-[(methylimino)trimethylene] linear chains are, by quaternization, joined through trimethylene or 2-hydroxy-trimthylene bridges; and reacting the said partially cross-linked, partially quaternized polymeric mixture with an excess of alkyl halide or trialkylammoniopropyl halide, thereby quaternizing any residual tertiary amine groupings present in the said polymeric mixture to form the corresponding substantially completely quaternized, 1% to 20% (1,3-trimethylene or 2-hydroxy-1,3-trimethylene)-cross-linked, poly-[(alkyl-methyliminio)trimethylene halide] or poly-[{methyl-(3-trialkylammoniopropyl)iminio}trimethylene dihalide].
Claim 3
Dependent Claim
48 words
The process as defined in claim 1 wherein poly-[(methylimino)trimethylene] is reacted with 1% to 20% of the stoichiometric equivalent of 1,3-dihalopropane, and the resulting 1,3-trimethylene-partially quaternized, partially cross-linked, poly-[(methylimino)trimethylene] is reacted with excess alkyl halide to form the corresponding substantially completely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly-[(alkylmethyliminio)trimethylene halide].
Claim 4
Dependent Claim
43 words
The process as defined in claim 1 wherein poly-[(methylimino)trimethylene] is reacted with approximately 20% of the stoichiometric equivalent of 1,3-dibromoprpane, and the resulting 20% quaternized, 20% 1,3-trimethylene-cross-linked, poly-[(methylimino(trimethylene] is reacted with excess methyl bromide to form substantially completely quaternized, 20% 1,3-trimethylene-cross-linked, poly-[(dimethyliminio)trimethylene bromide].
Claim 5
Dependent Claim
51 words
The process as defined in claim 1 wherein poly-[(methylimino)trimethylene] is reacted with about 1% to 20% of the stoichiometric equivalent of 2-hydroxy-1,3-dihalopropane, and the resulting partially quaternized, partially 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(methylimino)trimethylene] is reacted with an excess of alkyl halide to form the corresponding substantially completely quaternized, 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(alkyl-methyliminio)trimethylene halide].
Claim 6
Dependent Claim
45 words
The process as defined in claim 1 wherein poly-[(methylimino)trimethylene] is reacted with approximately 7% of the stoichiometric equivalent of 2-hydroxy-1,3-dichloropropane, and the resulting 7% quaternized, 7% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(methylimino)trimethylene] is reacted with excess methyl chloride to form the corresponding substantially completely quaternized, 7% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(dimethyliminio)trimethylene chloride].
Claim 7
Dependent Claim
49 words
The process as defined in claim 1 wherein poly-[(methylimino)trimethylene] is reacted with about 1% to 20% of the stoichiometric equivalent of 1,3-dihalopropane, and the resulting partially quaternized, partially 1,3-trimethylene-cross-linked, poly-[(methylimino)trimethylene] is reacted with excess trialkylammoniopropyl halide to form the corresponding substantially completely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly-[{methyl-(3-trialkylammoniopropyl)iminio}trimethylene dihalide].
Claim 8
Dependent Claim
46 words
The process as defined in claim 1 wherein poly-[(methylimino)trimethylene] is reacted with approximately 20% of the stoichiometric equivalent of 1,3-dibromopropane, and the resulting 20% quaternized, 20% 1,3-trimethylene-cross-linked, poly-[(methylimino(trimethylene] is reacted with an excess of trimethylammoniopropyl bromide to form the substantially completely quaternized, 20% 1,3-trimethylene-cross-linked, poly-[{methyl-(3-trimethylammoniopropyl)iminio}trimethylene dibromide].
Claim 9
Dependent Claim
49 words
The process as defined in claim 1 wherein poly-[(methylimino(trimethylene] is reacted with about 1% to 20% of the stoichiometric equivalent of 2-hydroxy-1,3-dihalopropane, and the resulting partially quaternized, partially 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(methylimino)trimethylene] is reacted with excess trialkylammoniopropyl halide to form the corresponding substantially completely quaternized, 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[{methyl-(3-trialkylammoniopropyl)iminio}trimethylene dihalide].
Claim 10
Dependent Claim
45 words
The process as defined in cllaim 1 wherein poly-[(methylimino)trimethylene] is reacted with about 7% of the stoichiometric equivalent of 2-hydroxy-1,3-dichloropropane, and the resulting 7% quaternized, 7% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(methylimino)trimethylene] is reacted with an excess of trimethylammoniopropyl chloride to form substantially completely quaternized, 7% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[{methyl-(3-trimethylammoniopropyl)iminio}trimethylene dichloride].
Claim 11
Dependent Claim
45 words
The process as defined in cllaim 1 wherein poly-[(methylimino)trimethylene] is reacted with about 7% of the stoichiometric equivalent of 2-hydroxy-1,3-dichloropropane, and the resulting 7% quaternized, 7% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(methylimino)trimethylene] is reacted with an excess of trimethylammoniopropyl chloride to form substantially completely quaternized, 7% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[{methyl-(3-trimethylammoniopropyl)iminio}trimethylene dichloride].
Claim 12
Dependent Claim
27 words
The substantially completely quaternized, 1% to 20% (1,3-trimethylene or 2-hydroxy-1,3-trimethylene)-cross-linked, poly-[{methyl-(alkyl or 3-trialkylammoniopropyl)iminio}trimethylene(halide, dihalide or other pharmacologically acceptable anion)], characterized as being active as bile acid sequestrant.
Claim 13
Dependent Claim
27 words
The substantially completely quaternized, 1% to 20% (1,3-trimethylene or 2-hydroxy-1,3-trimethylene)-cross-linked, poly-[{methyl-(alkyl or 3-trialkylammoniopropyl)iminio}trimethylene(halide, dihalide or other pharmacologically acceptable anion)], characterized as being active as bile acid sequestrant.
Claim 14
Dependent Claim
66 words
A partially cross-linked, quaternary polymer, having bile acid sequestrant activity, selected from the group consisting of completely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly-[(alkylmmethyliminio)trimethylene halide]; completely quaternized, 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(alkyl-methyliminio)trimethylene halide]; commpletely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly-[{methyl-(3-trialkylammoniopropyl)iminio}trimethylene dihalide]; and completely quaternized 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[{methyl-(3-trialkylammoniopropyl)iminio}trimethylene dihalide}, and pharmacologically acceptable salts thereof in which the halide counteranions are replaced by other pharmacologically acceptable counteranions.
Claim 15
Dependent Claim
66 words
A partially cross-linked, quaternary polymer, having bile acid sequestrant activity, selected from the group consisting of completely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly-[(alkylmmethyliminio)trimethylene halide]; completely quaternized, 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(alkyl-methyliminio)trimethylene halide]; commpletely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly-[{methyl-(3-trialkylammoniopropyl)iminio}trimethylene dihalide]; and completely quaternized 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[{methyl-(3-trialkylammoniopropyl)iminio}trimethylene dihalide}, and pharmacologically acceptable salts thereof in which the halide counteranions are replaced by other pharmacologically acceptable counteranions.
Claim 16
Dependent Claim
10 words
The substantially completely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly[(dimethyliminio)trimethylene chloride].
Claim 17
Dependent Claim
10 words
The substantially completely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly[(dimethyliminio)trimethylene chloride].
Claim 18
Dependent Claim
10 words
The substantially completely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly-[{methyl-(3-trimethylammoniopropyl)iminio}trimethylene dichloride].
Claim 19
Dependent Claim
10 words
The substantially completely quaternized, 1% to 20% 1,3-trimethylene-cross-linked, poly-[{methyl-(3-trimethylammoniopropyl)iminio}trimethylene dichloride].
Claim 20
Dependent Claim
10 words
The substantially completely quaternized, 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(dimethyliminio)trimethylene chloride].
Claim 21
Dependent Claim
10 words
The substantially completely quaternized, 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[(dimethyliminio)trimethylene chloride].
Claim 22
Dependent Claim
10 words
The substantially completely quaternized, 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[{methyl-(3-trimethylammoniopropyl)iminio}trimethylene dichloride].
Claim 23
Dependent Claim
10 words
The substantially completely quaternized, 1% to 20% 2-hydroxy-1,3-trimethylene-cross-linked, poly-[{methyl-(3-trimethylammoniopropyl)iminio}trimethylene dichloride].
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) | 1981-01-30 | 1981-08-01 | 1982-01-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-30 | 1985-08-01 | 1986-01-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-30 | 1989-08-01 | 1990-01-31 | $7700.00 | Window Closed / Lapsed |