CA2108569A1 - Polysaccharides sulfates utilises comme inhibiteurs de la proliferation des cellules musculaires lisses - Google Patents

Polysaccharides sulfates utilises comme inhibiteurs de la proliferation des cellules musculaires lisses

Info

Publication number: CA2108569A1
Authority: CA; Canada
Prior art keywords: so3r; mixture; smooth muscle; heparin; independently
Prior art date: 1991-04-17
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.): Abandoned

Application number

CA002108569A

Other languages

English (en)

Inventor

H. Edward Conrad

Brian K. Brandley

Lun H. Lam

Roger A. Laine

Peter Fugedi

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.)

Glycomed Inc

Original Assignee

Individual

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.)

1991-04-17

Filing date

1992-04-15

Publication date

1992-10-18

1992-04-15 Application filed by Individual filed Critical Individual

1992-10-18 Publication of CA2108569A1 publication Critical patent/CA2108569A1/fr

Status Abandoned legal-status Critical Current

Links

210000000329 smooth muscle myocyte Anatomy 0.000 title claims abstract description 32
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239000005017 polysaccharide Substances 0.000 title description 13
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229920001282 polysaccharide Polymers 0.000 title description 12
239000003112 inhibitor Substances 0.000 title description 3
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230000035755 proliferation Effects 0.000 claims abstract description 21
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IQSXIEUOGAEXMC-DDHJBXDOSA-N benzyl (2r,3r,4s,5r)-2-carbamoyl-3,4,5,6-tetrahydroxyhexanoate Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C(=O)N)C(=O)OCC1=CC=CC=C1 IQSXIEUOGAEXMC-DDHJBXDOSA-N 0.000 description 1
238000005574 benzylation reaction Methods 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 description 1
230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000309466 calf Species 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
229940107200 chondroitin sulfates Drugs 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
230000006196 deacetylation Effects 0.000 description 1
238000000432 density-gradient centrifugation Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
210000002889 endothelial cell Anatomy 0.000 description 1
239000003925 fat Substances 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
210000003754 fetus Anatomy 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
238000001215 fluorescent labelling Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
238000001641 gel filtration chromatography Methods 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
230000001279 glycosylating effect Effects 0.000 description 1
230000013595 glycosylation Effects 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
239000002634 heparin fragment Substances 0.000 description 1
108010038082 heparin proteoglycan Proteins 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
125000003103 iduronosyl group Chemical group 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
210000004347 intestinal mucosa Anatomy 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000007917 intracranial administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
KXCLCNHUUKTANI-RBIYJLQWSA-N keratan Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H]([C@@H](COS(O)(=O)=O)O[C@@H](O)[C@@H]3O)O)[C@H](NC(C)=O)[C@H]2O)COS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@@H]1O KXCLCNHUUKTANI-RBIYJLQWSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000012139 lysis buffer Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000002297 mitogenic effect Effects 0.000 description 1
210000000663 muscle cell Anatomy 0.000 description 1
230000003387 muscular Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
210000003668 pericyte Anatomy 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000012545 processing Methods 0.000 description 1
210000001147 pulmonary artery Anatomy 0.000 description 1
239000012063 pure reaction product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000000163 radioactive labelling Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000004921 regulation of smooth muscle cell proliferation Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
230000008439 repair process Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
150000003569 thioglycosides Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
230000008736 traumatic injury Effects 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
230000003966 vascular damage Effects 0.000 description 1
238000012795 verification Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
- 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
- C08B37/0078—Degradation products

Landscapes

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

CA002108569A 1991-04-17 1992-04-15 Polysaccharides sulfates utilises comme inhibiteurs de la proliferation des cellules musculaires lisses Abandoned CA2108569A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US68654091A	1991-04-17	1991-04-17
US686,540		1991-04-17

Publications (1)

Publication Number	Publication Date
CA2108569A1 true CA2108569A1 (fr)	1992-10-18

Family

ID=24756732

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002108569A Abandoned CA2108569A1 (fr)	1991-04-17	1992-04-15	Polysaccharides sulfates utilises comme inhibiteurs de la proliferation des cellules musculaires lisses

Country Status (6)

Country	Link
EP (1)	EP0582665A1 (fr)
JP (1)	JPH06506973A (fr)
AU (1)	AU1902592A (fr)
CA (1)	CA2108569A1 (fr)
NO (1)	NO933699L (fr)
WO (1)	WO1992018546A1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5811447A (en) *	1993-01-28	1998-09-22	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
US6395494B1 (en)	1993-05-13	2002-05-28	Neorx Corporation	Method to determine TGF-β
WO1994026303A1 (fr) *	1993-05-13	1994-11-24	Neorx Corporation	Prevention et traitement de pathologies associees a la proliferation anormale des cellules des muscles lisses
US5888984A (en) *	1994-05-12	1999-03-30	Dermal Research Laboratories, Inc.	Pharmaceutical composition of complex carbohydrates and essential oils and methods of using the same
AUPN261895A0 (en) *	1995-04-28	1995-05-18	Australian National University, The	Preparation and use of sulfated oligosaccharides
AUPO556297A0 (en)	1997-03-11	1997-04-10	Australian National University, The	Sulfated oligosaccharides having anticoagulant/ antithrombotic activity
AUPO888497A0 (en) *	1997-09-01	1997-09-25	Australian National University, The	Use of sulfated oligosaccharides as inhibitors of cardiovascular disease
AUPO976897A0 (en) *	1997-10-14	1997-11-06	Australian National University, The	Use of sulfated oligosaccharides in lowering blood triglyceride levels
AU2745700A (en)	1999-02-01	2000-08-18	Dermal Research Laboratories, Inc.	A pharmaceutical composition of complex carbohydrates and essential oils and methods of using the same
US7879824B2 (en)	2001-07-31	2011-02-01	Dermal Research Laboratories, Inc.	Methods of preventing or treating diseases and conditions using complex carbohydrates
US6613083B2 (en)	2001-05-02	2003-09-02	Eckhard Alt	Stent device and method
JPWO2005092348A1 (ja) *	2004-03-29	2008-02-07	敏一中村	ヘパリン様オリゴ糖含有ｈｇｆ産生促進薬剤
FR2949115B1 (fr) *	2009-08-14	2012-11-02	Sanofi Aventis	OLIGOSACCHARIDES N-SULFATES ACTIVATEURS DES RECEPTEURS DES FGFs, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
FR2949114B1 (fr) *	2009-08-14	2011-08-26	Sanofi Aventis	OCTASACCHARIDES N-ACYLES ACTIVATEURS DES RECEPTEURS DES FGFs, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL61201A (en) *	1979-10-05	1984-09-30	Choay Sa	Oligosaccharides having no more than 8 saccharide moieties,their obtention from heparin and pharmaceutical compositions containing them

1992
- 1992-04-15 EP EP92911854A patent/EP0582665A1/fr not_active Withdrawn
- 1992-04-15 AU AU19025/92A patent/AU1902592A/en not_active Abandoned
- 1992-04-15 JP JP4510890A patent/JPH06506973A/ja active Pending
- 1992-04-15 CA CA002108569A patent/CA2108569A1/fr not_active Abandoned
- 1992-04-15 WO PCT/US1992/003092 patent/WO1992018546A1/fr not_active Ceased
1993
- 1993-10-14 NO NO933699A patent/NO933699L/no unknown

Also Published As

Publication number	Publication date
WO1992018546A1 (fr)	1992-10-29
AU1902592A (en)	1992-11-17
JPH06506973A (ja)	1994-08-04
NO933699L (no)	1993-12-07
NO933699D0 (no)	1993-10-14
EP0582665A1 (fr)	1994-02-16

Legal Events

Date	Code	Title	Description
1994-10-17	FZDE	Dead

Publication	Publication Date	Title
US5380716A (en)	1995-01-10	Sulfated polysaccharides as inhibitors of smooth muscle cell proliferation
US5032679A (en)	1991-07-16	Heparin fragments as inhibitors of smooth muscle cell proliferation
US5250519A (en)	1993-10-05	Non-anticoagulant heparin derivatives
US5013724A (en)	1991-05-07	Process for the sulfation of glycosaminoglycans, the sulfated glycosaminoglycans and their biological applications
US5280016A (en)	1994-01-18	Non-anticoagulant heparin derivatives
EA001199B1 (ru)	2000-12-25	Сульфатированный олигосахарид, его применение для лечения теплокровных животных и фармацевтическая композиция на его основе
KR20040048404A (ko)	2004-06-09	혈관형성 억제 활성을 가지며 응고억제 효과는 없는,헤파라나제 억제제로서 부분적으로 탈황산화된글리코스아미노글리칸의 유도체
AU2435795A (en)	1995-11-29	O-desulfated heparin derivatives, methods of making and uses thereof
EP0582665A1 (fr)	1994-02-16	Polysaccharides sulfates en tant qu'inhibiteurs de la proliferation cellulaire dans les muscles lisses
EP1095657B1 (fr)	2007-01-10	Compositions pour la régulation de l'activité des cytokines
Garg et al.	1999	Effect of fully sulfated glycosaminoglycans on pulmonary artery smooth muscle cell proliferation
AU2003240190B2 (en)	2009-07-09	Epimerized derivatives of K5 polysaccharide with a very high degree of sulfation
US7618652B2 (en)	2009-11-17	Glycosaminoglycan anticoagulants derived from fish
JP4462826B2 (ja)	2010-05-12	骨疾患治療剤
WO1992017506A1 (fr)	1992-10-15	Modulation de l'activite de l'activateur du plasminogene tissulaire a l'aide de fragments d'heparine
RU2333222C2 (ru)	2008-09-10	Эпимеризованные производные полисахарида к5 с высокой степенью сульфатирования
Szabó et al.	1999	Thioglycoside antithrombotic agents
JP5051999B2 (ja)	2012-10-17	炎症性骨・軟骨疾患の処置剤
Garg et al.	2005	Influence of Heparin Chemical Modifications on its Antiproliferative Properties
ZA200410359B (en)	2005-07-21	Epimerized derivatives of K5 polysaccharide with a very high degree of sulfation.
MXPA97008289A (en)	1998-10-30	Preparation and use of oligosacaridos sulfata