KR940021582A - 2 위치가 수정된 α-L- 이두로닉 -2- 0- 설페이트산을 지닌 헤파린 또는 헤파란 구조를 갖는 반-합성 글리코스아미노글리칸의 합성방법 - Google Patents
2 위치가 수정된 α-L- 이두로닉 -2- 0- 설페이트산을 지닌 헤파린 또는 헤파란 구조를 갖는 반-합성 글리코스아미노글리칸의 합성방법 Download PDFInfo
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- KR940021582A KR940021582A KR1019940006018A KR19940006018A KR940021582A KR 940021582 A KR940021582 A KR 940021582A KR 1019940006018 A KR1019940006018 A KR 1019940006018A KR 19940006018 A KR19940006018 A KR 19940006018A KR 940021582 A KR940021582 A KR 940021582A
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- Prior art keywords
- radical
- acid
- heparin
- general formula
- aminoethanol
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- 229920002683 Glycosaminoglycan Polymers 0.000 title claims abstract 8
- 238000000034 method Methods 0.000 title claims abstract 7
- 229920002971 Heparan sulfate Chemical group 0.000 title claims abstract 6
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical group 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 6
- 229920000669 heparin Polymers 0.000 title claims abstract 6
- 229960002897 heparin Drugs 0.000 title claims abstract 6
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000012434 nucleophilic reagent Substances 0.000 claims abstract 5
- 230000000269 nucleophilic effect Effects 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract 2
- 230000002194 synthesizing effect Effects 0.000 claims abstract 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical class [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- -1 heterocyclic amine Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 239000000539 dimer Substances 0.000 claims 2
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims 2
- CHJFZKBUNXDBEL-UHFFFAOYSA-N 2-[(2-aminoacetyl)amino]ethanesulfonic acid Chemical compound NCC(=O)NCCS(O)(=O)=O CHJFZKBUNXDBEL-UHFFFAOYSA-N 0.000 claims 1
- AFLBTVGQCQLOFJ-UHFFFAOYSA-N 2-[[1-(2,6-diaminohexanoyl)pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NCCCCC(N)C(=O)N1CCCC1C(=O)NC(CCCN=C(N)N)C(O)=O AFLBTVGQCQLOFJ-UHFFFAOYSA-N 0.000 claims 1
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims 1
- YJSMIMJDRSWLQQ-UHFFFAOYSA-N 4-(3-aminopropyl)-2-hydroxybenzoic acid Chemical compound NCCCC1=CC=C(C(O)=O)C(O)=C1 YJSMIMJDRSWLQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- XBGGUPMXALFZOT-VIFPVBQESA-N Gly-Tyr Chemical compound NCC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 XBGGUPMXALFZOT-VIFPVBQESA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 108010008488 Glycylglycine Proteins 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims 1
- 239000004158 L-cystine Substances 0.000 claims 1
- 235000019393 L-cystine Nutrition 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
- QCZYYEFXOBKCNQ-STQMWFEESA-N Lys-Phe Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 QCZYYEFXOBKCNQ-STQMWFEESA-N 0.000 claims 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- HMNSRTLZAJHSIK-YUMQZZPRSA-N Pro-Arg Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1 HMNSRTLZAJHSIK-YUMQZZPRSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001413 amino acids Chemical group 0.000 claims 1
- 150000001414 amino alcohols Chemical group 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims 1
- 229960003067 cystine Drugs 0.000 claims 1
- 150000004662 dithiols Chemical class 0.000 claims 1
- WSYUEVRAMDSJKL-UHFFFAOYSA-N ethanolamine-o-sulfate Chemical compound NCCOS(O)(=O)=O WSYUEVRAMDSJKL-UHFFFAOYSA-N 0.000 claims 1
- 150000002169 ethanolamines Chemical class 0.000 claims 1
- YVKSGVDJQXLXDV-BYPYZUCNSA-N ethyl (2r)-2-amino-3-sulfanylpropanoate Chemical compound CCOC(=O)[C@@H](N)CS YVKSGVDJQXLXDV-BYPYZUCNSA-N 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 1
- 150000002332 glycine derivatives Chemical class 0.000 claims 1
- KZNQNBZMBZJQJO-YFKPBYRVSA-N glyclproline Chemical compound NCC(=O)N1CCC[C@H]1C(O)=O KZNQNBZMBZJQJO-YFKPBYRVSA-N 0.000 claims 1
- XBGGUPMXALFZOT-UHFFFAOYSA-N glycyl-L-tyrosine hemihydrate Natural products NCC(=O)NC(C(O)=O)CC1=CC=C(O)C=C1 XBGGUPMXALFZOT-UHFFFAOYSA-N 0.000 claims 1
- 229940043257 glycylglycine Drugs 0.000 claims 1
- 108010077515 glycylproline Proteins 0.000 claims 1
- 108010087823 glycyltyrosine Proteins 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims 1
- 150000002429 hydrazines Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 108010038320 lysylphenylalanine Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960003151 mercaptamine Drugs 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 108010004914 prolylarginine Proteins 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229960003080 taurine Drugs 0.000 claims 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical group SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001239 threonyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 claims 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
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
본 발명은, 설페이트기가 전부 또는 부분적으로 친핵성 래디칼로 치환되어 있는 α-L-이두로닉-2-0-설페이트산의 2 위치가 수정된 헤파린 또는 헤파란 구조를 갖는 다음 일반식 Ⅲ의 반-합성 글리코스아미노글리칸의 합성방법에 관한 것이다.
상기 제조방법은 헤파린 또는 헤파란 구조를 갖는 글리코스아미노글리칸을 알칼리성 매개물내의 친핵성시약으로 처리하여 수행되어진다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 다음 일반식(Ⅲ),(위 식에서 p+q=m이며, p는 0 이외의 수이고, m 및 n은 1-100 사이의 값인 모든 수이며, R은 수소 또는 설페이트(SO3-)잔기이고, -Z(R2)R1은 친핵성 래디칼을 나타낸다)의 헤파린 또는 헤파란 구조를 반-합성 글리코스아미노글리칸을 합성하는 방법으로서, 이 방법은 다음 일반식(Ⅰ),의 헤파린 또는 헤파란 구조를 갖는 글리코스아미노글리칸과, 래디칼이 다음 일반식(Ⅱ)로 나타내어지는 친핵성 시약 1-200몰당량(상기 일반식(Ⅱ)의 헤파린 또는 헤파란 구조를 갖는 글리코스아미노글리칸의 이합체 단위에 대하여)을 0℃-50℃의 온도에서 2-120시간 동안 교반하에, 경우에 따라서는 불활성 기체의 분위기하에서, 친핵성 시약 내에 존재하는 임의의 산(acid)기를 염화시키거나 또는 산성 물질을 가질 수 있는 임의의 염으로부터 동일한 친핵성 시약을 방출시키기에 충분한, 그리고 사용된 염기에 대하여 반응 혼합물이 0.01N-1N이 되도록 과량의 알칼리성을 방출해내기에 충분한 다량의 무기 또는 유기 염기의 존재하에 수용액 중에서 반응시키는 공정과, 냉각시킨 수용액의 pH를 염산수용액으로 중화시키고, 경우에 따라서는, 과량의 친핵성 시약을 제거하기 위해 물과 혼합되지 않는 용매로 추출하거나 또는 여과한 다음 이 수용액을 동결 건조시키거나 적당한 용매를 가하여 침전시킴에 의해서 생성물을 분리시키는 공정을 포함하는 것을 특징으로 하는 반-합성 글리코스아미노글리칸의 제조방법.
- 제 1 항에 있어서, 친핵성 시약의 량을 일반식(Ⅰ)로 글리코스아미노글리칸의 이합체 단위에 대하여 10-100몰당량이며, 상기 글리코스아미노글리칸의 수용액중 농도는 1-5%인 것을 특징으로 하는 제조방법.
- 제 1 항에 있어서, 사용된 염기는 수산화 나트륨, 수산화칼륨 및 트리에틸아민 중에서 선택되며, 과량의 알칼리성은 반응 혼합물이 사용된 염기에 대하여 0.5-1N이 되게 하는 것을 특징으로 하는 제조방법.
- 제1 내지 3항중 어느 한 항에 있어서, Z는 산소, 황 또는 질소를 나타내고, R1은 치환되거나 치환되지 않은, 직쇄 또는 측쇄(C1-C12) 알킬 래디칼, 아민 래디칼, 방향족 래디칼, 디아조 래디칼 또는 히드록실 래디칼을 나타내며, R2는 생략되거나, 수소원자, 직쇄 또는 측쇄(C1-C6) 알킬 래디칼, 또는 R1과 함께 헤테로시클릭 고리를 형성하는 것을 특징으로 하는 제조방법.
- 제 4 항에 있어서, -Z(R2)R1래디칼은 1차 또는 2차 아민, 2차 헤테로시클릭 아민, 아미노 알코올, 아미노티올, 아미노산, 아미노에스테르, 펩티드, 알코올, 페놀, 머캅탄, 디티올, 티오페놀, 히드록실아민, 히드라진, 히드라자이드 및 소디움 아자이드로부터 유도되는 것을 특징으로 하는 제조방법.
- 제 5 항에 있어서, -Z(R2)R1래디칼은 글리신, 글리실글리신, L-시스테인, 아세틸-L-시스테인, L-시스테인 에틸 에스테르, 2-아미노티오페놀, 1,3-프로판디티올, 시스테아민, 소디움 아자이드, 2-아미노에틸 비설페이트, 타우린, 티오글리콜산, β-알라닌 에틸 에스테르, L-시스틴, 히드록실아민, 글리실타우린, 시스테닐타우린, 글리실시스테인, 글리실페닐알라닌, 글리실티로신, 2-아미노에탄올, 2-아미노에탄올을 갖는 글리신 에스테르, 2-아미노에탄올을 갖는 글리신 아미드, 아르기닐리신, 아르기닌, 리신, 아세트산을 갖는 2-아미노에탄올 에스테르, 살리실산, 메티오닌, 글리실프롤린, r-아미노부티르산, 리실 프롤릴아르기닌, 트레오닐리실프롤린, 트레오닐리신, 프롤릴 아르기닌, 리신 프롤린, 콜린 4-(3-아미노프로필)-2-히드록시벤조산 및 4-(2-아미노 에틸)-2-히드록시벤조산으로부터 유도되는 것을 특징으로 하는 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITB093A000125 | 1993-03-29 | ||
| IT93BO000125A IT1264101B1 (it) | 1993-03-29 | 1993-03-29 | Processo per la sintesi di glicosaminoglicani semisintetici a struttura eparinica od eparanica modificati nella posizione 2 |
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| Publication Number | Publication Date |
|---|---|
| KR940021582A true KR940021582A (ko) | 1994-10-19 |
| KR100194122B1 KR100194122B1 (ko) | 1999-06-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1019940006018A KR100194122B1 (ko) | 1993-03-29 | 1994-03-25 | 2위치가 변형된 α-L-이두로닉-2-0-셀페이트산을 가진 헤파린 또는 헤파란 구조를 갖는 글리코스아미노글리칸의 제조방법 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5405949A (ko) |
| EP (1) | EP0618234B1 (ko) |
| JP (1) | JP2731721B2 (ko) |
| KR (1) | KR100194122B1 (ko) |
| AT (1) | ATE154039T1 (ko) |
| AU (1) | AU664939B2 (ko) |
| CA (1) | CA2114862C (ko) |
| DE (1) | DE69403537T2 (ko) |
| DK (1) | DK0618234T3 (ko) |
| ES (1) | ES2102087T3 (ko) |
| FI (1) | FI105101B (ko) |
| GR (1) | GR3024416T3 (ko) |
| IL (1) | IL108689A (ko) |
| IT (1) | IT1264101B1 (ko) |
| NO (1) | NO305994B1 (ko) |
| NZ (1) | NZ250815A (ko) |
| TW (1) | TW266215B (ko) |
| ZA (1) | ZA94970B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255295B1 (en) | 1996-12-23 | 2001-07-03 | Nutramax Laboratories, Inc. | Aminosugar, glycosaminoglycan or glycosaminoglycan-like compounds, and s-adenosylmethionine composition for the protection, treatment, repair, and reduction of inflammation of connective tissue |
| US7259152B2 (en) | 2000-06-07 | 2007-08-21 | Alfa Wasserman, Inc. | Methods and compositions using sulodexide for the treatment of diabetic nephropathy |
| EP1353556A4 (en) | 2001-01-23 | 2009-09-09 | Massachusetts Inst Technology | SYNTHESIS OF HEPARIN AND OTHER GLYCOSAMINOGLYCANS IN SOLID PHASE AND SOLUTION PHASE |
| SK288335B6 (sk) | 2001-09-12 | 2016-02-02 | Sigma-Tau Research Switzerland S.A. | Čiastočne alebo úplne N-desulfatovaný, N-reacetylovaný heparín, spôsob jeho prípravy, jeho použitie na prípravu liečiva s inhibičným účinkom na heparanázu, s antiangiogénnym a protizápalovým účinkom a farmaceutický prostriedok s jeho obsahom |
| GB0216861D0 (en) * | 2002-07-19 | 2002-08-28 | Univ Birmingham | Saccharide libraries |
| KR102468224B1 (ko) * | 2016-03-09 | 2022-11-17 | 가부시키가이샤 도우사 고가쿠 겐큐쇼 | 설페이트기 및/또는 포스페이트기를 갖는 당의 제조방법 |
| CN114901702B (zh) * | 2019-12-27 | 2024-01-09 | 深圳市海普瑞药业集团股份有限公司 | 一种糖胺聚糖衍生物及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4987223A (en) * | 1981-12-23 | 1991-01-22 | Choay S.A. | Derivatives of the uronic acid |
| US6174999B1 (en) * | 1987-09-18 | 2001-01-16 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| IT1234508B (it) * | 1988-06-10 | 1992-05-19 | Alfa Wassermann Spa | Derivati eparinici e procedimento per la loro preparazione |
| IT1234826B (it) * | 1989-01-30 | 1992-05-29 | Alfa Wassermann Spa | Derivati eparinici e procedimento per la loro preparazione |
| US5011919A (en) * | 1989-01-30 | 1991-04-30 | Ajorca S.A. | Modified heparins and obtention process |
| IT1242604B (it) * | 1990-11-13 | 1994-05-16 | Alfa Wassermann Spa | Sali di glicosaminoglicani con esteri di aminoacidi, loro preparazione e formulazioni farmaceutiche che li contengono. |
| IT1260137B (it) * | 1992-04-17 | 1996-03-28 | Alfa Wassermann Spa | Glicosaminoglicani semisintetici a struttura eparinica od eparanica modificati nella posizione 2 dell'acido alfa-l-iduronico-2-0-solfato |
| IT1260136B (it) * | 1992-04-17 | 1996-03-28 | Alfa Wassermann Spa | Glicosaminoglicani semisintetici contenenti acido alfa-l-galatturonicosostituito con radicali nucleofili in posizione 3 |
| BE1006134A6 (fr) * | 1992-08-25 | 1994-05-24 | Syntex Sa | Procede de preparation de derives 2-desoxy-2-amino hexuronyles d'heparine, derives tels qu'ainsi obtenus et leur utilisation. |
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1993
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- 1994-02-10 AU AU55085/94A patent/AU664939B2/en not_active Ceased
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- 1994-02-17 IL IL108689A patent/IL108689A/en not_active IP Right Cessation
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- 1994-03-25 KR KR1019940006018A patent/KR100194122B1/ko not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| AU5508594A (en) | 1994-10-06 |
| IT1264101B1 (it) | 1996-09-10 |
| ITBO930125A0 (it) | 1993-03-29 |
| CA2114862C (en) | 1999-05-25 |
| TW266215B (ko) | 1995-12-21 |
| JPH06298805A (ja) | 1994-10-25 |
| NO941128D0 (no) | 1994-03-28 |
| DK0618234T3 (da) | 1997-08-25 |
| JP2731721B2 (ja) | 1998-03-25 |
| NZ250815A (en) | 1996-02-27 |
| GR3024416T3 (en) | 1997-11-28 |
| ZA94970B (en) | 1994-08-24 |
| DE69403537D1 (de) | 1997-07-10 |
| FI105101B (fi) | 2000-06-15 |
| IL108689A0 (en) | 1994-05-30 |
| US5405949A (en) | 1995-04-11 |
| DE69403537T2 (de) | 1997-09-18 |
| AU664939B2 (en) | 1995-12-07 |
| EP0618234A1 (en) | 1994-10-05 |
| IL108689A (en) | 1998-03-10 |
| FI941431A0 (fi) | 1994-03-28 |
| ITBO930125A1 (it) | 1994-09-29 |
| NO305994B1 (no) | 1999-08-30 |
| ES2102087T3 (es) | 1997-07-16 |
| FI941431A (fi) | 1994-09-30 |
| ATE154039T1 (de) | 1997-06-15 |
| KR100194122B1 (ko) | 1999-06-15 |
| NO941128L (no) | 1994-09-30 |
| CA2114862A1 (en) | 1994-09-30 |
| EP0618234B1 (en) | 1997-06-04 |
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