DK175087B1 - Alkanoylestere af heparin, farmaceutisk præparat, der indeholder dem og anvendelse deraf - Google Patents

Alkanoylestere af heparin, farmaceutisk præparat, der indeholder dem og anvendelse deraf Download PDF

Info

Publication number: DK175087B1
Authority: DK; Denmark
Prior art keywords: heparin; ester; molecular weight; product; groups
Prior art date: 1986-08-20

Application number

DK198704345A

Other languages

Danish (da)

English (en)

Other versions

DK434587D0 (da

DK434587A (da

Inventor

Kevin Michael Foley

Charles Campbell Griffin

Original Assignee

Univ Miami

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.)

1986-08-20

Filing date

1987-08-20

Publication date

2004-05-24

1986-08-20 Priority claimed from US06/898,127 external-priority patent/US4745108A/en

1986-08-20 Priority claimed from US06/898,436 external-priority patent/US4745106A/en

1986-08-20 Priority claimed from US06/898,130 external-priority patent/US4745105A/en

1986-08-20 Priority claimed from US06/898,124 external-priority patent/US4745107A/en

1986-08-20 Priority claimed from US06/898,431 external-priority patent/US4942156A/en

1987-08-20 Application filed by Univ Miami filed Critical Univ Miami

1987-08-20 Publication of DK434587D0 publication Critical patent/DK434587D0/da

1988-02-21 Publication of DK434587A publication Critical patent/DK434587A/da

2004-05-24 Application granted granted Critical

2004-05-24 Publication of DK175087B1 publication Critical patent/DK175087B1/da

Links

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 title claims abstract description 161
229960002897 heparin Drugs 0.000 title claims abstract description 145
229920000669 heparin Polymers 0.000 title claims abstract description 145
125000001589 carboacyl group Chemical group 0.000 title 1
239000008194 pharmaceutical composition Substances 0.000 title 1
230000001858 anti-Xa Effects 0.000 claims abstract description 51
230000000694 effects Effects 0.000 claims abstract description 40
230000035699 permeability Effects 0.000 claims abstract description 29
150000002148 esters Chemical class 0.000 claims abstract description 28
-1 ester derivatives of heparin Chemical class 0.000 claims abstract description 8
125000004185 ester group Chemical group 0.000 claims description 42
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 38
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 16
238000005192 partition Methods 0.000 claims description 13
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 8
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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
VCOBYGVZILHVOO-UHFFFAOYSA-M 2-butanoyloxyethyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCC(=O)OCC[N+](C)(C)C VCOBYGVZILHVOO-UHFFFAOYSA-M 0.000 description 1
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230000028043 self proteolysis Effects 0.000 description 1
238000004513 sizing Methods 0.000 description 1
JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 1
DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
PNGBYKXZVCIZRN-UHFFFAOYSA-M sodium;hexadecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCCS([O-])(=O)=O PNGBYKXZVCIZRN-UHFFFAOYSA-M 0.000 description 1
WSVLUYNDHYCZGD-UHFFFAOYSA-M sodium;hexyl sulfate Chemical compound [Na+].CCCCCCOS([O-])(=O)=O WSVLUYNDHYCZGD-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
230000009424 thromboembolic effect Effects 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
210000004916 vomit Anatomy 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 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
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Diabetes (AREA)
Hematology (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Materials Engineering (AREA)
Polymers & Plastics (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Materials For Medical Uses (AREA)

DK198704345A 1986-08-20 1987-08-20 Alkanoylestere af heparin, farmaceutisk præparat, der indeholder dem og anvendelse deraf DK175087B1 (da)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date	Title
US89843186		1986-08-20
US89812486		1986-08-20
US06/898,127 US4745108A (en)	1986-08-20	1986-08-20	Heparin derivatives having decreased anti-Xa specificity
US89813086		1986-08-20
US06/898,436 US4745106A (en)	1986-08-20	1986-08-20	Heparin derivatives having improved anti-Xa specificity
US06/898,130 US4745105A (en)	1986-08-20	1986-08-20	Low molecular weight heparin derivatives with improved permeability
US89843686		1986-08-20
US89812786		1986-08-20
US06/898,124 US4745107A (en)	1986-08-20	1986-08-20	Heparin derivatives with improved permeability
US06/898,431 US4942156A (en)	1986-08-20	1986-08-20	Low molecular weight heparin derivatives having improved anti-Xa specificity

Publications (3)

Publication Number	Publication Date
DK434587D0 DK434587D0 (da)	1987-08-20
DK434587A DK434587A (da)	1988-02-21
DK175087B1 true DK175087B1 (da)	2004-05-24

Family

ID=27542290

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198704345A DK175087B1 (da)	1986-08-20	1987-08-20	Alkanoylestere af heparin, farmaceutisk præparat, der indeholder dem og anvendelse deraf

Country Status (8)

Country	Link
EP (1)	EP0256880B1 (fr)
JP (1)	JP2643950B2 (fr)
AT (1)	ATE122059T1 (fr)
CA (1)	CA1312861C (fr)
DE (1)	DE3751275T2 (fr)
DK (1)	DK175087B1 (fr)
ES (1)	ES2071608T3 (fr)
NO (1)	NO172803C (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3821271A1 (de) *	1988-06-23	1989-12-28	Solco Basel Ag	Derivatisiertes heparin, verfahren zu dessen herstellung und arzneimittel, welches dieses enthaelt
US5011919A (en) *	1989-01-30	1991-04-30	Ajorca S.A.	Modified heparins and obtention process
IT1243300B (it) *	1990-12-20	1994-05-26	Fidia Spa	Derivati dell'eparina
IT1286510B1 (it) *	1996-11-29	1998-07-15	Cooperativa Centro Ricerche Po	Esteri butirrici ad attivita' antiproliferativa e composizioni farmaceutiche che li contengono
JP4964577B2 (ja) *	2006-12-15	2012-07-04	有限会社応用糖質化学研究所	親脂質性ヘパリン修飾体、その製造方法及び毛髪成長促進剤
CN102516416A (zh) *	2011-12-28	2012-06-27	蚌埠医学院	一种肝素酯化物的合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1355036A (en) *	1970-04-14	1974-06-05	Ici Ltd	Articles of plastic film
JPS52111983A (en) *	1976-03-18	1977-09-20	Teijin Ltd	Preparation of heparin derivatives
JPS55158055A (en) *	1979-05-25	1980-12-09	Teijin Ltd	Preparation of antithrombus medical material
US4331697A (en) *	1980-09-02	1982-05-25	Teijin Limited	Novel heparin derivative, method for production thereof, and method for rendering biomedical materials antithrombotic by use of the novel heparin derivative
CA1195322A (fr) *	1982-07-19	1985-10-15	Eduardo Amaya	Procede de production d'heparines a faible poids moleculaire par depolarisation de l'heparine normale

1987
- 1987-08-18 AT AT87307292T patent/ATE122059T1/de not_active IP Right Cessation
- 1987-08-18 DE DE3751275T patent/DE3751275T2/de not_active Expired - Lifetime
- 1987-08-18 ES ES87307292T patent/ES2071608T3/es not_active Expired - Lifetime
- 1987-08-18 EP EP87307292A patent/EP0256880B1/fr not_active Expired - Lifetime
- 1987-08-19 NO NO87873501A patent/NO172803C/no not_active IP Right Cessation
- 1987-08-20 JP JP62207359A patent/JP2643950B2/ja not_active Expired - Lifetime
- 1987-08-20 DK DK198704345A patent/DK175087B1/da not_active IP Right Cessation
- 1987-08-21 CA CA000545111A patent/CA1312861C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO873501L (no)	1988-02-22
DE3751275T2 (de)	1995-09-07
EP0256880B1 (fr)	1995-05-03
NO873501D0 (no)	1987-08-19
DK434587D0 (da)	1987-08-20
ATE122059T1 (de)	1995-05-15
EP0256880A2 (fr)	1988-02-24
ES2071608T3 (es)	1995-07-01
DE3751275D1 (de)	1995-06-08
DK434587A (da)	1988-02-21
EP0256880A3 (en)	1988-12-14
NO172803B (no)	1993-06-01
JP2643950B2 (ja)	1997-08-25
NO172803C (no)	1993-09-08
CA1312861C (fr)	1993-01-19
JPS6366202A (ja)	1988-03-24

Legal Events

Date	Code	Title	Description
2007-09-10	PUP	Patent expired

Publication	Publication Date	Title
US5008253A (en)	1991-04-16	Sulfoamino derivatives of chondroitin sulfates of dermatan sulfate and of hyaluronic acid and their pharmacological properties
US4990502A (en)	1991-02-05	Low molecular weight heparins of regular structure, their preparation and their biological uses.
DK173818B1 (da)	2001-11-19	Heparinderivat
US5280016A (en)	1994-01-18	Non-anticoagulant heparin derivatives
JP5351770B2 (ja)	2013-11-27	ビオチンまたはビオチン誘導体との少なくとも１つの共有結合を含む低分子量ヘパリン、これらの作製方法およびそれらの使用。
DK160764B (da)	1991-04-15	Analogifremgangsmaade til fremstilling af terapeutisk aktive heparinfragmenter
JPH11504018A (ja)	1999-04-06	硫酸化オリゴ糖の製造および使用
EP0439555B1 (fr)	1995-03-08	Oligosaccharides actifs contre l'atherosclerose
EP0337327A1 (fr)	1989-10-18	Procédé de préparation de fractions oligosaccharides par une dépolymérisation chimique réglée d'héparine
JPS59133202A (ja)	1984-07-31	解重合及び超硫酸化ヘパリン、その製造方法並びに製薬組成物
AU3544295A (en)	1996-03-22	Method for controlling o-desulfation of heparin and compositions produced thereby
WO1998014481A1 (fr)	1998-04-09	Procedes de preparation d'heparines a faible affinite et a faible masse molaire utiles en tant qu'antithrombotiques
JPH051101A (ja)	1993-01-08	Ｎ，ｏ−硫酸化ヘパロザン、製法および医薬組成物
US7833990B2 (en)	2010-11-16	Use of low-molecular-weight highly sulfated polysaccharide derivatives for modulating angiogenesis
DK175087B1 (da)	2004-05-24	Alkanoylestere af heparin, farmaceutisk præparat, der indeholder dem og anvendelse deraf
DK172798B1 (da)	1999-07-19	Fremgangsmåde til fremstilling af lavmolekylære hepariner ved depolymerisation af normal heparin
US5849721A (en)	1998-12-15	Sulfated polysaccharides obtained from heparin, preparation process, pharmaceutical composition and use thereof
AU671817B2 (en)	1996-09-12	Sulphated polysaccharides, preparation thereof, pharmaceutical composition and use thereof
Merchant et al.	1986	Effect of very low molecular weight henarin-derived oligosaccharides on lipoprotein lipase release in rabbits
US20100075922A1 (en)	2010-03-25	Heparins including at least one covalent bond with biotin or a biotin derivative, method for preparing same and use thereof
JP2714718B2 (ja)	1998-02-16	新規硫酸化多糖及びその薬学的に許容される塩、その製造方法並びにそれを有効成分とする医薬
AU2003242881A1 (en)	2003-12-31	Low molecular weight oversulfated polysaccharide
JPH02124902A (ja)	1990-05-14	血液凝固抑制剤
WO2020163926A1 (fr)	2020-08-20	Héparine bovine sûre, procédé de préparation et application
Jeske et al.	1996	Pharmacology of Synthetic and Biotechnology-Derived Homologues and Analogues of Heparin