Patent US4510135A successfully refreshed from Google Patents.
US4510135A
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US
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Orally administered heparin
Assignee: Research Corp
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Filing: 1982-04-21
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Granted: 1985-04-09
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Expires: 2002-04-21
Abstract
Abstract An orally administrable heparin comprising: a complex of heparin with (1) a protonated tertiary organic ammonium ion having the formula: ##STR1## wherein R 1 , R 2 and R 3 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 1 and R 3 together with the N atom can form a pyrrolidine, imidazole or morpholine ring; or (2) an ester-containing quaternary ammonium ion having the formula: ##STR2## wherein R 4 , R 5 and R 6 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 4 and R 6 together with the N atom can form a pyrrolidine, imidazole or morpholine ring; R 7 represents an alkyl group of 4 to 16 carbon atoms; and R 8 represents a hydrogen atom or a methyl group.
Inventors
- 👤 Lin-nar L. Teng
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 21:23
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/70; A61K31/715; A61K47/00; A61K47/50; A61K47/51; A61K47/54; A61K47/541; A61K47/542; A61K47/543; A61K47/544; C; C08; C08B; C08B37/00; C08B37/006; C08B37/0063; C08B37/0075
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
83 words
A complex of heparin with a protonated tertiary organic ammonium ion, wherein said ammonium ion has the formula: ##STR15## wherein R 1 , R 2 and R 3 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 1 and R 3 together with the N atom can form a heterocyclic ring of the formula: ##STR16## wherein R 2 has the meaning set forth above.
Claim 2
Dependent Claim
83 words
A complex of heparin with a protonated tertiary organic ammonium ion, wherein said ammonium ion has the formula: ##STR15## wherein R 1 , R 2 and R 3 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 1 and R 3 together with the N atom can form a heterocyclic ring of the formula: ##STR16## wherein R 2 has the meaning set forth above.
Claim 3
Dependent Claim
41 words
The complex according to claim 1, wherein R 1 , R 2 and R 3 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups.
Claim 4
Dependent Claim
30 words
The complex according to claim 1 or 2, wherein said ammonium ion is present in a ratio of 5 moles of ammonium ion to 1 mole of heparin tetrasaccharide unit.
Claim 5
Dependent Claim
28 words
The complex according to claim 1 or 2, wherein said ammonium ion is present in a stoichiometric excess over the amount necessary to form a complex with heparin.
Claim 6
Dependent Claim
105 words
A complex of heparin with an ester-containing quaternary ammonium ion, wherein said ammonium ion has the formula: ##STR17## wherein R 4 , R 5 and R 6 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 4 and R 6 together with the N atoms can form a heterocyclic ring of the formula: ##STR18## wherein R 5 has the meaning set forth above; R 7 represents an alkyl group of 4 to 16 carbon atoms; and R 8 represents a hydrogen atom or a methyl group.
Claim 7
Dependent Claim
105 words
A complex of heparin with an ester-containing quaternary ammonium ion, wherein said ammonium ion has the formula: ##STR17## wherein R 4 , R 5 and R 6 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 4 and R 6 together with the N atoms can form a heterocyclic ring of the formula: ##STR18## wherein R 5 has the meaning set forth above; R 7 represents an alkyl group of 4 to 16 carbon atoms; and R 8 represents a hydrogen atom or a methyl group.
Claim 8
Dependent Claim
41 words
The complex according to claim 5, wherein R 4 , R 5 and R 6 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups.
Claim 9
Dependent Claim
17 words
The complex according to claim 6, wherein said alkyl group is of 1 to 5 carbon atoms.
Claim 10
Dependent Claim
30 words
The complex according to claim 5 or 6, wherein said ammonium ion is present in a ratio of 5 moles of ammonium ion to 1 mole of heparin tetrasaccharide unit.
Claim 11
Dependent Claim
28 words
The complex according to claim 5 or 6, wherein said ammonium ion is present in a stoichiometric excess over the amount necessary to form a complex with heparin.
Claim 12
Dependent Claim
21 words
A blood anticoagulant composition comprising an anticoagulant effective amount of the complex according to claim 1 and a pharmaceutically acceptable excipient.
Claim 13
Dependent Claim
12 words
The composition according to claim 10, in the form of a tablet.
Claim 14
Dependent Claim
13 words
The composition according to claim 10, in the form of an aqueous dispersion.
Claim 15
Dependent Claim
21 words
A blood anticoagulant composition comprising an anticoagulant effective amount of the complex according to claim 5 and a pharmaceutically acceptable excipient.
Claim 16
Dependent Claim
12 words
The composition according to claim 13, in the form of a cream.
Claim 17
Dependent Claim
12 words
The composition according to claim 13, in the form of an ointment.
Claim 18
Dependent Claim
12 words
The composition according to claim 13, in the form of a suppository.
Claim 19
Dependent Claim
104 words
The process of orally administering a blood anticoagulant to a mammal which comprises orally administering in a blood anticoagulant effective amount a complex of heparin with a protonated tertiary organic ammonium ion, wherein said ammonium ion has the formula: ##STR19## wherein R 1 , R 2 and R 3 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 1 and R 3 together with the N atom can form a heterocyclic ring of the formula: ##STR20## wherein R 2 has the meaning set forth above.
Claim 20
Dependent Claim
104 words
The process of orally administering a blood anticoagulant to a mammal which comprises orally administering in a blood anticoagulant effective amount a complex of heparin with a protonated tertiary organic ammonium ion, wherein said ammonium ion has the formula: ##STR19## wherein R 1 , R 2 and R 3 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 1 and R 3 together with the N atom can form a heterocyclic ring of the formula: ##STR20## wherein R 2 has the meaning set forth above.
Claim 21
Dependent Claim
126 words
The process of orally administering a blood anticoagulant to a mammal which comprises orally administering in a blood anticoagulant effective amount a complex of heparin with an ester-containing quaternary ammonium ion, wherein said ammonium ion has the formula: ##STR21## wherein R 4 , R 5 and R 6 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 4 and R 6 together with the N atom can form a heterocyclic ring of the formula: ##STR22## wherein R 5 has the meaning set forth above; R 7 represents an alkyl group of 4 to 16 carbon atoms; and R 8 represents a hydrogen atom or a methyl group.
Claim 22
Dependent Claim
126 words
The process of orally administering a blood anticoagulant to a mammal which comprises orally administering in a blood anticoagulant effective amount a complex of heparin with an ester-containing quaternary ammonium ion, wherein said ammonium ion has the formula: ##STR21## wherein R 4 , R 5 and R 6 each independently represent a branched or unbranched alkyl group of 1 to 12 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 4 and R 6 together with the N atom can form a heterocyclic ring of the formula: ##STR22## wherein R 5 has the meaning set forth above; R 7 represents an alkyl group of 4 to 16 carbon atoms; and R 8 represents a hydrogen atom or a methyl group.
Claim 23
Dependent Claim
83 words
A complex of heparin with a protonated tertiary organic ammonium ion, wherein said ammonium ion has the formula: ##STR23## wherein R 1 , R 2 and R 3 each independently represents a branched or unbranched alkyl group of 1 to 5 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 1 and R 3 together with the N atom can form a heterocyclic ring of the formula: ##STR24## wherein R 2 has the meaning set forth above.
Claim 24
Dependent Claim
83 words
A complex of heparin with a protonated tertiary organic ammonium ion, wherein said ammonium ion has the formula: ##STR23## wherein R 1 , R 2 and R 3 each independently represents a branched or unbranched alkyl group of 1 to 5 carbon atoms, which may be unsubstituted or substituted with hydroxy or alkoxy groups, or R 1 and R 3 together with the N atom can form a heterocyclic ring of the formula: ##STR24## wherein R 2 has the meaning set forth above.
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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) | 1988-04-08 | 1988-10-08 | 1989-04-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-08 | 1992-10-08 | 1993-04-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-08 | 1996-10-08 | 1997-04-09 | $7700.00 | Window Closed / Lapsed |