EP0015909A1 - A method of producing thrombosis-resistant surfaces - Google Patents

A method of producing thrombosis-resistant surfaces

Info

Publication number: EP0015909A1
Authority: EP; European Patent Office
Prior art keywords: heparin; hirudin; salt; metal; palladium
Prior art date: 1978-02-17
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP19790900219

Other languages

German (de)

English (en)

French (fr)

Inventor

Axel Emil BERGSTRÖM

Billy Valter SÖDERVALL

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

THIN CONDUCTIVE COATING OSTERMALM

Original Assignee

THIN CONDUCTIVE COATING OSTERMALM

Priority date (The priority date 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 date listed.)

1978-02-17

Filing date

1979-09-11

Publication date

1980-10-01

1979-09-11 Application filed by THIN CONDUCTIVE COATING OSTERMALM filed Critical THIN CONDUCTIVE COATING OSTERMALM

1980-10-01 Publication of EP0015909A1 publication Critical patent/EP0015909A1/en

Status Withdrawn legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
208000007536 Thrombosis Diseases 0.000 title description 7
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims abstract description 21
229960002897 heparin Drugs 0.000 claims abstract description 21
229920000669 heparin Polymers 0.000 claims abstract description 21
229910052751 metal Inorganic materials 0.000 claims abstract description 19
239000002184 metal Substances 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 14
102000007625 Hirudins Human genes 0.000 claims abstract description 10
108010007267 Hirudins Proteins 0.000 claims abstract description 10
229940006607 hirudin Drugs 0.000 claims abstract description 10
WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 claims abstract description 10
210000004369 blood Anatomy 0.000 claims abstract description 8
239000008280 blood Substances 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 6
239000002506 anticoagulant protein Substances 0.000 claims abstract description 5
150000002940 palladium Chemical class 0.000 claims abstract description 4
238000009736 wetting Methods 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
239000000243 solution Substances 0.000 claims description 10
229910052763 palladium Inorganic materials 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 4
229910052703 rhodium Inorganic materials 0.000 claims description 4
239000010948 rhodium Substances 0.000 claims description 4
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
239000008103 glucose Substances 0.000 claims description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
239000003146 anticoagulant agent Substances 0.000 claims description 2
229940127219 anticoagulant drug Drugs 0.000 claims description 2
230000001427 coherent effect Effects 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 4
210000002381 plasma Anatomy 0.000 abstract description 2
102000004169 proteins and genes Human genes 0.000 abstract description 2
108090000623 proteins and genes Proteins 0.000 abstract description 2
150000003283 rhodium Chemical class 0.000 abstract description 2
230000001112 coagulating effect Effects 0.000 abstract 1
239000004033 plastic Substances 0.000 description 7
229920003023 plastic Polymers 0.000 description 7
238000011282 treatment Methods 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
210000001772 blood platelet Anatomy 0.000 description 3
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
LCTORNIWLGOBPB-GASJEMHNSA-N (3r,4s,5s,6r)-2-amino-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical group NC1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LCTORNIWLGOBPB-GASJEMHNSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 1
LCTORNIWLGOBPB-DVKNGEFBSA-N (2s,3r,4s,5s,6r)-2-amino-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound N[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LCTORNIWLGOBPB-DVKNGEFBSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
229920002683 Glycosaminoglycan Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241001474977 Palla Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
102000002262 Thromboplastin Human genes 0.000 description 1
108010000499 Thromboplastin Proteins 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
-1 acryl Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
229920005549 butyl rubber Polymers 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000005530 etching Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229940097043 glucuronic acid Drugs 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0005—Use of materials characterised by their function or physical properties
- A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
- A61L33/0017—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate using a surface active agent

Definitions

the present invention relates to a novel method of effect ⁇ ively treating surfaces with heparin, hirudin and other anticoagulant proteins for the purpose of rendering said surfaces resistant to thrombosis.
the method comprises the treatment of said surface with a palladium salt or a rhodium salt prior to heparising said surface.
Heparin which is a mucopolysaccharide from D-glucoseamine and glucuronic acid with a molecular weight of about 17000, has the ability of preventing the aforementioned formation of a thrombus. It is essential that a heparinized surface is stable and that the heparin is firmly bound to the surface of the object.
-stage method of heparinizing a surface which method, in addition to washing stages, comprises treating the surface with hexadecyl amine hydrochloride heparin, an aminesoluti t glutaraldehyde and cooking salt.
the product is considerab better than one whose surfaces have not been treated.
the layers produced when applying this method tend to be uneve and are also liable to be washed-off by the blood flowing thereagainst, consequently, there is a need of improving the method.
Heparin shares this property with hirudin and other anticoagulant proteins.
Hirudin is a protein having a molecular weight of 16000 - 1000.
the surface to be treated may be of practically any materi whatsoever, although preferably the surface is of metal, such as a stainless steel, a plastics material, such as polyvinyl chloride, polyolefins, acryl resins and co-poly ⁇ mers thereof, silicon plastics, rubber, particularly butyl rubber, and fluorocarbon plastics.
metal such as a stainless steel
plastics material such as polyvinyl chloride, polyolefins, acryl resins and co-poly ⁇ mers thereof, silicon plastics, rubber, particularly butyl rubber, and fluorocarbon plastics.
the treatment metal may be one of a number of different metals. Those metals tested in particular included palladium, rhodium, nickel, cobalt and copper. Among these metals palladium and rhodium take a particular position, owing to the fact that peptide hydrogen ionisation takes place at an optimal pH range of 3-4. The pH range in the case of nickel is 4-6, in the case of cobalt 6-8 and in the case of copper 8-10. With regard to these properties see E.W. Wilson and R.B. Martin, Inorg. Chem 9, page 528 (1970).
the well-cleaned, and optionally etched surface is treated with a solution of a metal salt of the metal soluble in the solvent used, with a preferably pharmaceutically acceptable acid.
a suitable solvent there can be mentioned primarily water, and water in mix ⁇ tures with a polar solvent m-iscible therewith.
Polar organic solvents can also be used. Among those polar solvents which can be used are alkanols, such as methanol and ethanol.
Suitable salts are primarily chlorides, sul ⁇ phates, nitrates, acetates, citrates, although it lies within the expertise of one skilled in this art to select other suitable soluble salts of the metal used.
Rhodium can be used in the same manner.
the treatment with the metal salt takes only some seccnds up to some minutes, depending upon the temperature of the solution and its pH, and takes place at an ion strength o 0.3-3 mmol metal salt per litre, which in the case of the mentioned palladium salts corresponds to 0.1-0.5 grams of salt per litre.
the temperature may be room temperature, although a temperature of 50-80 c C is preferred.
the surface is treated with a heparin solution containing 1000-10000 IE heparin per litre.
the solution contains mainly water and other suitable substances such as sodium chloride and glucose.
the treatment time also varies here, although normally requires a treatment time 15-45 minutes. Glucose can be added to stabilise the solu tion.
the treatment method proposed in accordance with the in ⁇ vention results in the formation of a heparin layer which, has been judged, on the tests carried out, to be some ten times better than a heparin layer produced in accordance with the present standpoint of technics. It is assumed th palladium binds to the amine group in the glucose amine part of the heparin molecule, possibly in combination with van den Waals bonds to oxygen atoms in the heparin chain and in the sulphone group which is bound to the amine gro in the glucose amine part of the molecule.

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Hematology (AREA)
Surgery (AREA)
Epidemiology (AREA)
Materials Engineering (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Materials For Medical Uses (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
External Artificial Organs (AREA)

EP19790900219 1978-02-17 1979-09-11 A method of producing thrombosis-resistant surfaces Withdrawn EP0015909A1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE7801853		1978-02-17
SE7801853		1978-02-17

Publications (1)

Publication Number	Publication Date
EP0015909A1 true EP0015909A1 (en)	1980-10-01

Family

ID=20334023

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP19790900219 Withdrawn EP0015909A1 (en)	1978-02-17	1979-09-11	A method of producing thrombosis-resistant surfaces

Country Status (4)

Country	Link
EP (1)	EP0015909A1 (da)
JP (1)	JPS55500091A (da)
DK (1)	DK427079A (da)
WO (1)	WO1979000638A1 (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU625215B2 (en) *	1988-06-04	1992-07-02	Sanofi-Aventis Deutschland Gmbh	Hirudin derivatives with delayed action

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5112615A (en) *	1988-08-03	1992-05-12	New England Deaconess Hospital Corporation	Soluble hirudin conjugates
US5281662A (en) *	1988-08-03	1994-01-25	New England Deaconess Hospital Corporation	Anthraquinone dye treated materials
US5167960A (en) *	1988-08-03	1992-12-01	New England Deaconess Hospital Corporation	Hirudin-coated biocompatible substance
CA2000887A1 (en) *	1988-11-01	1990-05-01	Cecilia S.L. Ku	Thromboresistant materials and methods for making same
US5196404B1 (en) *	1989-08-18	1996-09-10	Biogen Inc	Inhibitors of thrombin
US5135516A (en) *	1989-12-15	1992-08-04	Boston Scientific Corporation	Lubricious antithrombogenic catheters, guidewires and coatings
US5843089A (en)	1990-12-28	1998-12-01	Boston Scientific Corporation	Stent lining
ATE170982T1 (de) *	1990-02-14	1998-09-15	Pentapharm Ag	Inhibitoren zur antikoagulierenden vorbehandung von blutproben
AU8492991A (en) *	1990-10-04	1992-04-28	New England Deaconess Hospital Corporation	Soluble thrombogenesis inhibitor conjugates
DK194091D0 (da) *	1991-11-29	1991-11-29	Metra Aps	Hydrofil og biokompatibel coatede overflader
CN112043877B (zh) *	2020-08-06	2022-10-14	苏州大学	一种蚕丝抗凝血管支架覆膜及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2702253A (en) *	1950-11-01	1955-02-15	Gasaccumulator Svenska Ab	Surface metallizing method
US3549409A (en) *	1969-04-28	1970-12-22	Cordis Corp	Production of nonthrombogenic plastics

1979
- 1979-02-16 WO PCT/SE1979/000035 patent/WO1979000638A1/en not_active Ceased
- 1979-02-16 JP JP50042479A patent/JPS55500091A/ja active Pending
- 1979-09-11 EP EP19790900219 patent/EP0015909A1/en not_active Withdrawn
- 1979-10-10 DK DK427079A patent/DK427079A/da not_active Application Discontinuation

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* Cited by examiner, † Cited by third party
Title
See references of WO7900638A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU625215B2 (en) *	1988-06-04	1992-07-02	Sanofi-Aventis Deutschland Gmbh	Hirudin derivatives with delayed action

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Publication number	Publication date
JPS55500091A (da)	1980-02-14
DK427079A (da)	1979-10-10
WO1979000638A1 (en)	1979-09-06

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Date	Code	Title	Description
1980-08-05	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1980-10-01	AK	Designated contracting states	Designated state(s): FR
1981-02-03	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN
1981-04-08	18D	Application deemed to be withdrawn	Effective date: 19801227
2007-08-08	RIN1	Information on inventor provided before grant (corrected)	Inventor name: SOEDERVALL, BILLY, VALTER Inventor name: BERGSTROEM, AXEL, EMIL

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CA2503490C (en)	2012-04-03	Medical device surface coating comprising bioactive compound
US6146771A (en)	2000-11-14	Process for modifying surfaces using the reaction product of a water-insoluble polymer and a polyalkylene imine
EP0015909A1 (en)	1980-10-01	A method of producing thrombosis-resistant surfaces
JPH05500314A (ja)	1993-01-28	改良されたイオン性ヘパリンコーティング
JPH0145373B2 (da)	1989-10-03
AU6502590A (en)	1991-05-16	Process for the preparation of surface modified solid substrates
US5001062A (en)	1991-03-19	Antithrombogenic article containing lysozyme and heparin adsorbed on a substrate
EP0231573B1 (en)	1991-11-06	Improved ionic heparin coating
CA1340800C (en)	1999-10-26	Articles exhibiting a blood-compatible surface layer and process for providing articles with such a surface layer
JP2001204809A (ja)	2001-07-31	血液適合性組成物およびそれを被覆した医療用具
WO2023225749A1 (en)	2023-11-30	Multifunctional surface modification of biomaterials with agents to reduce thrombosis
EP0484057A2 (en)	1992-05-06	Antithrombogenic surfaces, their preparation, and materials therefore
US20060159650A1 (en)	2006-07-20	Composition and method for covalently coupling an antithrombotic substance and a hydrophilic polymer
JPH04146766A (ja)	1992-05-20	抗血栓性医用材料および医用器具
JPH053916A (ja)	1993-01-14	血液中電解質センサ用被覆材料
JP2003048840A (ja)	2003-02-21	抗菌性付与抗血栓性組成物およびそれをコートした医療用具
JP2004008628A (ja)	2004-01-15	医療用具の製造方法
AU2317888A (en)	1989-03-31	Articles exhibiting a blood-compatible surface layer and process for providing articles with such a surface layer
JPH04312467A (ja)	1992-11-04	抗血栓性医用材料、医用器具および抗血栓性医用材料の製造方法
NO321372B1 (no)	2006-05-02	Anvendelse av en sammensetning som omfatter heparin for fremstilling av en ikke-trombogen overflate.

EP0015909A1 - A method of producing thrombosis-resistant surfaces - Google Patents

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