Patent US5527624A successfully refreshed from Google Patents.
EP0165569A2
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Heparin derivatives
Assignee: B Braun Surgical AG
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Filing: 1985-06-14
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Granted: —
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Expires: 2005-06-14
Abstract
Abstract The invention comprises heparin derivative compounds which possess a low density lipoprotein lowering action without a significant anticoagulent effect, and are therefore useful in the treatment of disturbances of fat metabolism, especially hyperlipidemia. The heparin derivatives of the invention are derived from natural heparin, and are prepared by the hydrolysis of heparin and optionally, subsequent acylation at free amine groups of the hydrolyzed heparin.
Inventors
- 👤 Wolfgang Dr. Feller
- 👤 Rainer Störmer
- 👤 Annemarie Müller
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-29 16:10
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/70; A61K31/715; A61P; A61P3/00; A61P3/06; C; C08; C08B; C08B37/00; C08B37/006; C08B37/0063; C08B37/0075
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
23 words
A heparin derivative compound characterized by a low density lipoprotein lowering action while minimizing or eliminating an anticoagulent effect normally associated with heparin.
Claim 2
Dependent Claim
23 words
A heparin derivative compound characterized by a low density lipoprotein lowering action while minimizing or eliminating an anticoagulent effect normally associated with heparin.
Claim 3
Dependent Claim
26 words
The heparin derivative compound according to claim 1 which is selected from the group consisting of hydrolyzed heparin and hydrolyzed heparin acylated at free amine groups.
Claim 4
Dependent Claim
30 words
The heparin derivative compound according to claim 1, characterized by a coagulation activity of less than about 20 IU/mg and low binding affinity to antithrombin III as compared to heparin.
Claim 5
Dependent Claim
44 words
The heparin derivative according to claim 2, wherein the hydrolyzed heparin has a content of free amine groups of 50 to 400 µmol/g and the hydrolyzed heparin acylated at free amine groups has a content of free amine groups of 2 to 10 pmol/g.
Claim 6
Dependent Claim
47 words
The heparin derivative compound claims 1 to 4 wherein said acylated hydrolyzed hepar is prepared by reacting a heparin hydrolyzate with anhydrides or acid halides selected from the group consising of oxalic acid, malonic acid, succinic acid, haloacetic acid, halopropionic acid, haloacylic acid and substituted phthalic acid.
Claim 7
Dependent Claim
107 words
A process for the preparation of low density lipoprotein-precipitating heparin derivatives from natural heparin which comprises the steps of: a) subjecting heparin and any desired salts thereof to a mild, controlled, acid hydrolysis reaction at a predetermined acid pH for a predetermined period of time; b) cooling the reaction and adjusting the pH to a level higher than the predetermined acid pH of step (a) by the addition of an alkali to create a reaction product; c) dialyzing the reaction; d) drying the reaction product by known methods; said reaction product comprising a heparin derivative capable of precipitating low density lipoproteins with little or no anticoagulent effect.
Claim 8
Dependent Claim
107 words
A process for the preparation of low density lipoprotein-precipitating heparin derivatives from natural heparin which comprises the steps of: a) subjecting heparin and any desired salts thereof to a mild, controlled, acid hydrolysis reaction at a predetermined acid pH for a predetermined period of time; b) cooling the reaction and adjusting the pH to a level higher than the predetermined acid pH of step (a) by the addition of an alkali to create a reaction product; c) dialyzing the reaction; d) drying the reaction product by known methods; said reaction product comprising a heparin derivative capable of precipitating low density lipoproteins with little or no anticoagulent effect.
Claim 9
Dependent Claim
39 words
7 . The process according to claim 6 which further comprises acylating the reaction product at free amine groups thereof to form a hydrolyzed, acylated heparin derivative capable of precipitating low density lipoproteins with little or no anticoagulent effect.
Claim 10
Dependent Claim
69 words
The process according to any one of claims 6 and 7 wherein said predetermined pH is between 1.0 and 5.0, said predetermined period of time is between 90 minutes and 30 hours, said acid hyrolysis is performed with aqueous 0.2 to 0.33 M acid at 45 to 70°C, said cooling is conducted between 0°C and 30°C and in step b), the pH is adjusted to between 6.0 and 8.0.
Claim 11
Dependent Claim
14 words
The process according to claim 8 , wherein said acid is a mineral acid.
Claim 12
Dependent Claim
21 words
The process according to claim 6, wherein an acid buffer is added during the acid hydrolysis treatment reaction of step (a).
Claim 13
Dependent Claim
28 words
The process according to claim 8, wherein the hydrolysis treatment is carried out a pH of 1.0, a temperature of 70°C and for a period of 80 minutes.
Claim 14
Dependent Claim
45 words
12 . The process according to claim 7, wherein the reaction product is acylated at free amine groups by reaction with mono-or dicarboxylic acids of 1 to 8 carbon atoms or their anhydrides, acid halides or derivatives substituted with halogens at the hydrocarbon portion thereof.
Claim 15
Dependent Claim
25 words
A pharmaceutical preparation for the treatment of hyperlipidemia and the prevention of angionesis of tumors comprising a heparin derivative according to claims 1 to 5.
References Cited (Backward Citations)
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