DE69723926T2 - Verfahren zur synthese von gm2 - Google Patents
Verfahren zur synthese von gm2 Download PDFInfo
- Publication number
- DE69723926T2 DE69723926T2 DE69723926T DE69723926T DE69723926T2 DE 69723926 T2 DE69723926 T2 DE 69723926T2 DE 69723926 T DE69723926 T DE 69723926T DE 69723926 T DE69723926 T DE 69723926T DE 69723926 T2 DE69723926 T2 DE 69723926T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- group
- benzyl
- pivaloyl
- vib
- 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
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- 238000003786 synthesis reaction Methods 0.000 title description 8
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- 239000000348 glycosyl donor Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 14
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- 239000000460 chlorine Substances 0.000 claims description 10
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 6
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- 239000002245 particle Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 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 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000004044 tetrasaccharides Chemical class 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Lock And Its Accessories (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Catalysts (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/602,580 US5756695A (en) | 1996-02-16 | 1996-02-16 | Methods of synthesizing GM2 |
| US602580 | 1996-02-16 | ||
| PCT/US1997/001944 WO1997030061A1 (en) | 1996-02-16 | 1997-02-05 | Methods of synthesizing gm2 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69723926D1 DE69723926D1 (de) | 2003-09-11 |
| DE69723926T2 true DE69723926T2 (de) | 2004-07-15 |
Family
ID=24411928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69723926T Expired - Fee Related DE69723926T2 (de) | 1996-02-16 | 1997-02-05 | Verfahren zur synthese von gm2 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5756695A (enExample) |
| EP (1) | EP0821691B1 (enExample) |
| JP (2) | JP3220704B2 (enExample) |
| AT (1) | ATE246697T1 (enExample) |
| AU (1) | AU712149B2 (enExample) |
| CA (1) | CA2217708A1 (enExample) |
| DE (1) | DE69723926T2 (enExample) |
| WO (1) | WO1997030061A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5977329A (en) * | 1996-02-16 | 1999-11-02 | Ludwig Institute For Cancer Research | Methods of synthesizing GM3 |
| US5951317A (en) * | 1998-04-13 | 1999-09-14 | Motorola, Inc. | Accessory connector assembly |
| CN1300158C (zh) * | 2005-03-22 | 2007-02-14 | 重庆邮电学院 | 一类非天然活性寡糖类化合物及其制备方法和应用 |
| WO2011053614A1 (en) * | 2009-10-30 | 2011-05-05 | Merck Sharp & Dohme Corp. | Crystalline cdm-nag and methods for producing same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0508493A1 (en) * | 1986-08-06 | 1992-10-14 | Mect Corporation | Ganglioside related compounds and method of producing the same |
| US5371202A (en) * | 1991-02-28 | 1994-12-06 | The Nisshin Oil Mills, Ltd. | Processes of preparing sialoglycosyl compounds |
-
1996
- 1996-02-16 US US08/602,580 patent/US5756695A/en not_active Expired - Fee Related
-
1997
- 1997-02-05 EP EP97904258A patent/EP0821691B1/en not_active Expired - Lifetime
- 1997-02-05 CA CA002217708A patent/CA2217708A1/en not_active Abandoned
- 1997-02-05 JP JP52939897A patent/JP3220704B2/ja not_active Expired - Fee Related
- 1997-02-05 DE DE69723926T patent/DE69723926T2/de not_active Expired - Fee Related
- 1997-02-05 AU AU18586/97A patent/AU712149B2/en not_active Ceased
- 1997-02-05 WO PCT/US1997/001944 patent/WO1997030061A1/en not_active Ceased
- 1997-02-05 AT AT97904258T patent/ATE246697T1/de not_active IP Right Cessation
-
2001
- 2001-05-16 JP JP2001145749A patent/JP2001316397A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0821691B1 (en) | 2003-08-06 |
| JPH11504348A (ja) | 1999-04-20 |
| US5756695A (en) | 1998-05-26 |
| EP0821691A4 (en) | 2001-10-04 |
| JP3220704B2 (ja) | 2001-10-22 |
| AU1858697A (en) | 1997-09-02 |
| DE69723926D1 (de) | 2003-09-11 |
| AU712149B2 (en) | 1999-10-28 |
| WO1997030061A1 (en) | 1997-08-21 |
| JP2001316397A (ja) | 2001-11-13 |
| CA2217708A1 (en) | 1997-08-21 |
| ATE246697T1 (de) | 2003-08-15 |
| EP0821691A1 (en) | 1998-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |