GB603571A - Compounds having a retarding action on the coagulation of blood and processes of preparing the same - Google Patents
Compounds having a retarding action on the coagulation of blood and processes of preparing the sameInfo
- Publication number
- GB603571A GB603571A GB20952/44A GB2095244A GB603571A GB 603571 A GB603571 A GB 603571A GB 20952/44 A GB20952/44 A GB 20952/44A GB 2095244 A GB2095244 A GB 2095244A GB 603571 A GB603571 A GB 603571A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dextrane
- ester
- sulphuric acid
- partially hydrolysed
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000008280 blood Substances 0.000 title abstract 3
- 210000004369 blood Anatomy 0.000 title abstract 3
- 230000015271 coagulation Effects 0.000 title abstract 2
- 238000005345 coagulation Methods 0.000 title abstract 2
- 230000000979 retarding effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- 150000002148 esters Chemical class 0.000 abstract 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 239000000243 solution Substances 0.000 abstract 5
- 239000001117 sulphuric acid Substances 0.000 abstract 5
- 235000011149 sulphuric acid Nutrition 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 230000032050 esterification Effects 0.000 abstract 4
- 238000005886 esterification reaction Methods 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 3
- -1 oleum Chemical compound 0.000 abstract 3
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 3
- 159000000000 sodium salts Chemical class 0.000 abstract 3
- 239000005864 Sulphur Substances 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000006386 neutralization reaction Methods 0.000 abstract 2
- 238000001556 precipitation Methods 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 2
- 230000001225 therapeutic effect Effects 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 229910001422 barium ion Inorganic materials 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- 229910001424 calcium ion Inorganic materials 0.000 abstract 1
- 238000000502 dialysis Methods 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 238000010253 intravenous injection Methods 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Sulphuric acid esters of dextrane are prepared by subjecting dextrane, which may be partially hydrolysed, to the action of a sulphating agent, for example sulphur trioxide, concentrated sulphuric acid, oleum, sulphuryl chloride, N-pyridinium sulphonic or, preferably, chlorsulphonic acid. The esterification may vary from less than one esterified OH-group per glucose unit up to complete esterification. The acid esters may be partially or completely neutralized by means of a basic compound, preferably by alkali or alkaline earth bases. The salt or ester may be freed of sulphuric acid by dialysis, by precipitation of the salt or ester from aqueous solution with alcohol or by precipitating the sulphuric acid by means of Ca or Ba ions. The salts or esters may be used as anti-coagulating agents in the treatment of blood (see Group VI). In an example, a partially hydrolysed dextrane, prepared by boiling a 4 per cent aqueous dextrane solution with hydrochloric acid for 3 minutes followed by neutralization with caustic soda and precipitation as the sodium salt by addition of alcohol, was reacted with chlorsulphonic acid in anhydrous pyridine and the resulting sulphuric acid ester of dextrane precipitated by addition of alcohol. The ester was then dissolved in water, neutralized with caustic soda, the solution dialysed until free of sulphuric acid after which the sodium salt of the ester was precipitated by addition of alcohol. A suitable partially hydrolysed dextrane may also be of the kind disclosed in Specification 583,378.ALSO:In an example, a partially hydrolysed dextrane is prepared by boiling an aqueous solution of dextrane with concentrated hydrochloric acid for 3 minutes, the solution then being cooled and neutralised with caustic soda; the partially hydrolysed dextrane obtained is precipitated by addition of alcohol. Reference is made to the preparation of such dextrane disclosed in Specification 583,378, [Group IV].ALSO:Sulphuric acid esters of dextrane in the neutralised or unneutralised state (see Group IV) may be employed as agents for retarding the coagulation of blood. Preferably the esters are derived from partially hydrolysed dextrane of the kind disclosed in Specification 583,378 (as open to inspection under Sect. 91) [Group IV]. Salts of these esters, particularly of alkali or alkaline earth metals in water, saline solutions or other therapeutic fluids yield alone or in admixture with other physiologically suitable salts and therapeutic substances, solutions well adapted for intravenous injection. The degree of esterification of the dextrane may vary from a sulphur content below that of the mono-ester up to complete esterification while p the neutralisation may be partial or complete. An example describes the preparation of the sodium salt of the sulphur ester of a partially hydrolysed dextrane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE603571X | 1943-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB603571A true GB603571A (en) | 1948-06-18 |
Family
ID=20312868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20952/44A Expired GB603571A (en) | 1943-11-13 | 1944-10-27 | Compounds having a retarding action on the coagulation of blood and processes of preparing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB603571A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2638469A (en) * | 1950-05-19 | 1953-05-12 | American Home Prod | Process for alginic acid sulfate production |
| US2638470A (en) * | 1950-05-19 | 1953-05-12 | American Home Prod | Process for the production of alginic acid sulfate |
| US2689848A (en) * | 1951-02-06 | 1954-09-21 | Wander Ag Dr A | Salts of sulfuric acid esters of xylan |
| US2715091A (en) * | 1949-11-28 | 1955-08-09 | Nat Res Dev | Dextran sulfate as anticoagulant, process of preparing same, and sterile solution thereof |
| US2729633A (en) * | 1952-05-13 | 1956-01-03 | American Home Prod | Sulfated pectic acid blood anticoagulant |
| US2786833A (en) * | 1953-11-24 | 1957-03-26 | Nat Starch Products Inc | Sulfation of amylaceous materials |
| US2897193A (en) * | 1954-05-28 | 1959-07-28 | Ohio Commw Eng Co | Sulfuric acid esters of dextranic acid |
| US2914444A (en) * | 1950-12-12 | 1959-11-24 | David F Smith | Cellulosic hemostatic composition |
| WO1988007060A1 (en) * | 1987-03-19 | 1988-09-22 | Arthropharm Pty. Limited | Anti-inflammatory compounds and compositions |
| US5668116A (en) * | 1987-03-19 | 1997-09-16 | Anthropharm Pty. Limited | Anti-inflammatory compounds and compositions |
-
1944
- 1944-10-27 GB GB20952/44A patent/GB603571A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2715091A (en) * | 1949-11-28 | 1955-08-09 | Nat Res Dev | Dextran sulfate as anticoagulant, process of preparing same, and sterile solution thereof |
| US2638469A (en) * | 1950-05-19 | 1953-05-12 | American Home Prod | Process for alginic acid sulfate production |
| US2638470A (en) * | 1950-05-19 | 1953-05-12 | American Home Prod | Process for the production of alginic acid sulfate |
| US2914444A (en) * | 1950-12-12 | 1959-11-24 | David F Smith | Cellulosic hemostatic composition |
| US2689848A (en) * | 1951-02-06 | 1954-09-21 | Wander Ag Dr A | Salts of sulfuric acid esters of xylan |
| US2729633A (en) * | 1952-05-13 | 1956-01-03 | American Home Prod | Sulfated pectic acid blood anticoagulant |
| US2786833A (en) * | 1953-11-24 | 1957-03-26 | Nat Starch Products Inc | Sulfation of amylaceous materials |
| US2897193A (en) * | 1954-05-28 | 1959-07-28 | Ohio Commw Eng Co | Sulfuric acid esters of dextranic acid |
| WO1988007060A1 (en) * | 1987-03-19 | 1988-09-22 | Arthropharm Pty. Limited | Anti-inflammatory compounds and compositions |
| US5145841A (en) * | 1987-03-19 | 1992-09-08 | Arthropharm Pty. Limited | Anti-inflammatory compounds and compositions |
| US5470840A (en) * | 1987-03-19 | 1995-11-28 | Arthropharm Pty Limited | Anti-inflammatory compounds and compositions |
| US5668116A (en) * | 1987-03-19 | 1997-09-16 | Anthropharm Pty. Limited | Anti-inflammatory compounds and compositions |
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