DE69122936T2 - Verfahren zur Herstellung von Sialsäure - Google Patents
Verfahren zur Herstellung von SialsäureInfo
- Publication number
- DE69122936T2 DE69122936T2 DE69122936T DE69122936T DE69122936T2 DE 69122936 T2 DE69122936 T2 DE 69122936T2 DE 69122936 T DE69122936 T DE 69122936T DE 69122936 T DE69122936 T DE 69122936T DE 69122936 T2 DE69122936 T2 DE 69122936T2
- Authority
- DE
- Germany
- Prior art keywords
- sialic acid
- egg yolk
- acid
- exchange resin
- hydrolysis
- 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 - Fee Related
Links
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 title claims description 98
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 title claims description 87
- 238000000034 method Methods 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title description 8
- 108010000912 Egg Proteins Proteins 0.000 claims description 54
- 102000002322 Egg Proteins Human genes 0.000 claims description 54
- 235000013345 egg yolk Nutrition 0.000 claims description 53
- 210000002969 egg yolk Anatomy 0.000 claims description 52
- 150000002632 lipids Chemical class 0.000 claims description 21
- 230000007062 hydrolysis Effects 0.000 claims description 17
- 238000006460 hydrolysis reaction Methods 0.000 claims description 17
- 238000011033 desalting Methods 0.000 claims description 14
- 239000003957 anion exchange resin Substances 0.000 claims description 12
- 238000000909 electrodialysis Methods 0.000 claims description 12
- 239000012528 membrane Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000010612 desalination reaction Methods 0.000 claims description 7
- 238000001223 reverse osmosis Methods 0.000 claims description 7
- 239000003456 ion exchange resin Substances 0.000 claims description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 5
- 239000003729 cation exchange resin Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000000126 substance Substances 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 10
- 239000000413 hydrolysate Substances 0.000 description 9
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005903 acid hydrolysis reaction Methods 0.000 description 6
- 238000004945 emulsification Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 108091005804 Peptidases Proteins 0.000 description 4
- 239000004365 Protease Substances 0.000 description 4
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910001863 barium hydroxide Inorganic materials 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 125000005629 sialic acid group Chemical group 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 102000005348 Neuraminidase Human genes 0.000 description 3
- 108010006232 Neuraminidase Proteins 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 210000000991 chicken egg Anatomy 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229920001542 oligosaccharide Polymers 0.000 description 3
- 150000002482 oligosaccharides Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 210000001006 meconium Anatomy 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- HLLSOEKIMZEGFV-UHFFFAOYSA-N 4-(dibutylsulfamoyl)benzoic acid Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 HLLSOEKIMZEGFV-UHFFFAOYSA-N 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- 101000767534 Arabidopsis thaliana Chorismate mutase 2 Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 241000219173 Carica Species 0.000 description 1
- 235000009467 Carica papaya Nutrition 0.000 description 1
- 102000009016 Cholera Toxin Human genes 0.000 description 1
- 108010049048 Cholera Toxin Proteins 0.000 description 1
- 206010061126 Escherichia infection Diseases 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 1
- 108010064983 Ovomucin Proteins 0.000 description 1
- 102000018265 Virus Receptors Human genes 0.000 description 1
- 108010066342 Virus Receptors Proteins 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- YQZKMBQLQRZWPA-UHFFFAOYSA-N benzene-1,3-diol;periodic acid Chemical compound OI(=O)(=O)=O.OC1=CC=CC(O)=C1 YQZKMBQLQRZWPA-UHFFFAOYSA-N 0.000 description 1
- 235000015155 buttermilk Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 230000005859 cell recognition Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000020247 cow milk Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000015961 delipidation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 208000020612 escherichia coli infection Diseases 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical class OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 238000011034 membrane dialysis Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 210000001534 vitelline membrane Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/027—Keto-aldonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2235434A JPH06102672B2 (ja) | 1990-09-04 | 1990-09-04 | シアル酸の製造法 |
| JP19242791A JPH0737474B2 (ja) | 1991-07-05 | 1991-07-05 | 高純度シアル酸の精製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69122936D1 DE69122936D1 (de) | 1996-12-05 |
| DE69122936T2 true DE69122936T2 (de) | 1997-03-06 |
Family
ID=26507313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69122936T Expired - Fee Related DE69122936T2 (de) | 1990-09-04 | 1991-08-22 | Verfahren zur Herstellung von Sialsäure |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5233033A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0474410B1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2050125A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE69122936T2 (cg-RX-API-DMAC10.html) |
| IL (1) | IL99245A0 (cg-RX-API-DMAC10.html) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2747967B2 (ja) * | 1993-07-23 | 1998-05-06 | 雪印乳業株式会社 | シアル酸粉末 |
| EP0718304A1 (en) * | 1994-12-14 | 1996-06-26 | Snow Brand Milk Products Co., Ltd. | Sialic acid powder and process for the preparation thereof |
| JP2001502005A (ja) | 1996-10-10 | 2001-02-13 | サイテル コーポレイション | 限外濾過、逆浸透及びナノ濾過を利用する炭水化物の精製 |
| US6126731A (en) * | 1998-08-21 | 2000-10-03 | Idea Development Company | Polymerizable ink composition |
| KR100386424B1 (ko) * | 2000-01-10 | 2003-06-02 | 주식회사 두산 | 시알산 함유 올리고당의 제조방법 |
| EP1367048B1 (en) * | 2000-05-25 | 2009-07-22 | Sekisui Chemical Co., Ltd. | Photo-setting compositions and photoreactive adhesive compositions |
| US7054851B2 (en) * | 2001-06-25 | 2006-05-30 | Siemens Medical Solutions Health Services Corporation | Communication data format for use in data storage and retrieval |
| CN101466829B (zh) | 2006-02-09 | 2012-03-14 | 麦迪卡格公司 | 唾液酸在植物中的合成 |
| CN101139624B (zh) * | 2006-09-06 | 2012-08-22 | 北京德青源农业科技股份有限公司 | 一种制备涎酸寡糖肽的方法 |
| CA2687639A1 (en) * | 2007-06-25 | 2008-12-31 | Dsm Ip Assets B.V. | Novel prebiotics |
| NL2001377C2 (nl) * | 2008-03-14 | 2009-09-15 | Friesland Brands Bv | Werkwijze voor het isoleren van siaalzuur bevattende oligosachariden, alsmede de hiermee verkrijgbare siaalzuur bevattende oligosachariden bevatttende samenstellingen. |
| CA2722179A1 (en) * | 2008-04-25 | 2009-10-29 | Incorporated Administrative Agency, National Agriculture And Food Resear Ch Organization | Method for extracting sialic acid-containing compound from plant |
| JP4682377B2 (ja) * | 2009-10-06 | 2011-05-11 | 独立行政法人農業・食品産業技術総合研究機構 | 植物からのシアル酸含有化合物の抽出法 |
| EP2454946B1 (en) * | 2010-11-23 | 2017-01-04 | Darling Ingredients International Holding B.V. | Method for desalting animal tissue |
| CN103060403A (zh) * | 2011-10-18 | 2013-04-24 | 邹如 | 一种从蛋黄粉提取燕窝酸的方法 |
| US20160106799A1 (en) * | 2013-05-29 | 2016-04-21 | Siamab Therapeutics, Inc. | Carbohydrate Compounds for Nutritional and Therapeutic Use |
| EP3486326A1 (en) | 2017-11-21 | 2019-05-22 | Jennewein Biotechnologie GmbH | Method for the purification of n-acetylneuraminic acid from a fermentation broth |
| CN109776626B (zh) * | 2018-12-29 | 2020-06-23 | 中国科学院合肥物质科学研究院 | 一种预防唾液酸水溶液变色的方法 |
| CN114539333B (zh) * | 2022-03-01 | 2023-12-22 | 德元堂(上海)健康科技发展有限公司 | 一种唾液酸的循环生产工艺 |
| CN114507262B (zh) * | 2022-03-01 | 2023-12-19 | 德元堂(上海)健康科技发展有限公司 | 一种聚唾液酸的水解工艺 |
| CN114891051A (zh) * | 2022-06-21 | 2022-08-12 | 小仙炖霸州食品有限公司 | 一种超声波联合球磨粉碎法水提燕窝酸的方法 |
| CN117137090B (zh) * | 2023-08-25 | 2024-07-12 | 广州菲勒生物科技有限公司 | 一种水解蛋黄粉复合物及其制备方法 |
| CN119285684A (zh) * | 2024-10-14 | 2025-01-10 | 常州凯幸生物技术有限公司 | 一种从发酵液中分离提取唾液酸的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4888324A (en) * | 1985-10-01 | 1989-12-19 | Angio-Medical Corporation | Method for enhancing angiogenesis with lipid containing molecules |
| JPH0269492A (ja) * | 1988-09-02 | 1990-03-08 | Taiyo Kagaku Co Ltd | シアル酸の製造方法 |
-
1991
- 1991-08-20 IL IL99245A patent/IL99245A0/xx unknown
- 1991-08-22 DE DE69122936T patent/DE69122936T2/de not_active Expired - Fee Related
- 1991-08-22 EP EP91307753A patent/EP0474410B1/en not_active Expired - Lifetime
- 1991-08-22 US US07/748,560 patent/US5233033A/en not_active Expired - Lifetime
- 1991-08-29 CA CA002050125A patent/CA2050125A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0474410A2 (en) | 1992-03-11 |
| EP0474410A3 (cg-RX-API-DMAC10.html) | 1994-04-20 |
| EP0474410B1 (en) | 1996-10-30 |
| US5233033A (en) | 1993-08-03 |
| IL99245A0 (en) | 1992-07-15 |
| CA2050125A1 (en) | 1992-03-05 |
| DE69122936D1 (de) | 1996-12-05 |
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