FR2319373A1 - Nouveau procede d'esterification selective des fonctions alcool primaire de diholosides et produits ainsi obtenus - Google Patents
Nouveau procede d'esterification selective des fonctions alcool primaire de diholosides et produits ainsi obtenusInfo
- Publication number
- FR2319373A1 FR2319373A1 FR7523578A FR7523578A FR2319373A1 FR 2319373 A1 FR2319373 A1 FR 2319373A1 FR 7523578 A FR7523578 A FR 7523578A FR 7523578 A FR7523578 A FR 7523578A FR 2319373 A1 FR2319373 A1 FR 2319373A1
- Authority
- FR
- France
- Prior art keywords
- silylated
- fatty acid
- diholosides
- diesterified
- prodn
- 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.)
- Granted
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title abstract 2
- 229930195729 fatty acid Natural products 0.000 title abstract 2
- 239000000194 fatty acid Substances 0.000 title abstract 2
- 150000004665 fatty acids Chemical class 0.000 title abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 abstract 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000001024 immunotherapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
-
- 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
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7523578A FR2319373A1 (fr) | 1975-07-29 | 1975-07-29 | Nouveau procede d'esterification selective des fonctions alcool primaire de diholosides et produits ainsi obtenus |
| BE1007514A BE844272A (fr) | 1975-07-29 | 1976-07-19 | Nouveau procede d'esterification selective des fonctions alcool primaire de diholosides et produits ainsi ontenus |
| DE19762633690 DE2633690A1 (de) | 1975-07-29 | 1976-07-27 | Verfahren zur selektiven veresterung der primaeren alkoholfunktionen von diholosiden, die dabei erhaltenen produkte und ihre therapeutische verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7523578A FR2319373A1 (fr) | 1975-07-29 | 1975-07-29 | Nouveau procede d'esterification selective des fonctions alcool primaire de diholosides et produits ainsi obtenus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2319373A1 true FR2319373A1 (fr) | 1977-02-25 |
| FR2319373B1 FR2319373B1 (enExample) | 1978-12-01 |
Family
ID=9158463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7523578A Granted FR2319373A1 (fr) | 1975-07-29 | 1975-07-29 | Nouveau procede d'esterification selective des fonctions alcool primaire de diholosides et produits ainsi obtenus |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE844272A (enExample) |
| DE (1) | DE2633690A1 (enExample) |
| FR (1) | FR2319373A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2355506A1 (fr) * | 1976-06-25 | 1978-01-20 | Azuma Ichiro | Adjuvant d'immunotherapie contenant un glycolipide comme ingredient actif et son procede de preparation |
| EP0005682A1 (de) * | 1978-05-18 | 1979-11-28 | Ciba-Geigy Ag | Silyl-glucosaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| FR2477551A1 (fr) * | 1980-03-10 | 1981-09-11 | Anvar | Nouveaux derives de l'a, a'-trehalose et medicaments les contenant |
| FR2479000A1 (fr) * | 1980-03-28 | 1981-10-02 | Research Corp | Vaccin contre la brucellose, maladie du betail |
| FR2534259A1 (fr) * | 1982-10-08 | 1984-04-13 | Ss Pharmaceutical Co | Diester d'acide aliphatique a chaine moyenne en positions 6, 6' d'a,a-trehalose et son application en therapeutique |
| US4574058A (en) * | 1978-02-24 | 1986-03-04 | Ciba-Geigy Corporation | Antigen derivatives and processes for their preparation |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3315264A1 (de) * | 1982-04-29 | 1983-12-01 | Ribi Immunochem Research, Inc.,, 59840 Hamilton, Mont. | Verfahren zur reinigung von rohen trehalosedimycolaten |
| US5049664A (en) * | 1988-08-26 | 1991-09-17 | Sawai Pharmaceutical Co., Ltd. | Trehalose derivatives |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH63A (de) * | 1889-01-08 | Oesterr Alpine Montan | Hydraulische Presse zur Herstellung von Bleiumhüllungen an Kabeln und von Bleiröhren | |
| CH77A (de) * | 1889-01-09 | Christian Herren | Wurzelschneidmaschine | |
| CH76A (fr) * | 1888-11-14 | 1889-01-09 | Carnal Paul E | Nouveau système de boîte de montre pouvant servir à volonté comme savonnette ou comme boîte à glace |
| CH79A (de) * | 1889-01-09 | Adam Sautter Johann | Uhrwerk für Taschenuhren mit offenem Federhaus, neuem Gangrücker-System und vereinfachter Werkbefestigung |
-
1975
- 1975-07-29 FR FR7523578A patent/FR2319373A1/fr active Granted
-
1976
- 1976-07-19 BE BE1007514A patent/BE844272A/xx unknown
- 1976-07-27 DE DE19762633690 patent/DE2633690A1/de not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH63A (de) * | 1889-01-08 | Oesterr Alpine Montan | Hydraulische Presse zur Herstellung von Bleiumhüllungen an Kabeln und von Bleiröhren | |
| CH77A (de) * | 1889-01-09 | Christian Herren | Wurzelschneidmaschine | |
| CH79A (de) * | 1889-01-09 | Adam Sautter Johann | Uhrwerk für Taschenuhren mit offenem Federhaus, neuem Gangrücker-System und vereinfachter Werkbefestigung | |
| CH76A (fr) * | 1888-11-14 | 1889-01-09 | Carnal Paul E | Nouveau système de boîte de montre pouvant servir à volonté comme savonnette ou comme boîte à glace |
Non-Patent Citations (5)
| Title |
|---|
| 11 DOCUMENT CITE DANS LA DEMANDE EXAMINEE * |
| 1965 7093G, CITE CAN J. CHEM. 43 7 2004 * |
| 1972 28 833N CITE NIPPON SAIKINGAKU ZASSHI 1971, 26 11 533-6) * |
| 1972 81.777C CITE SCIENCE 1971, 174 4015 1240-2 * |
| 1973 155.815T CITE BIOCHEMIE 1973 55 5 575-578 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2355506A1 (fr) * | 1976-06-25 | 1978-01-20 | Azuma Ichiro | Adjuvant d'immunotherapie contenant un glycolipide comme ingredient actif et son procede de preparation |
| US4574058A (en) * | 1978-02-24 | 1986-03-04 | Ciba-Geigy Corporation | Antigen derivatives and processes for their preparation |
| EP0005682A1 (de) * | 1978-05-18 | 1979-11-28 | Ciba-Geigy Ag | Silyl-glucosaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| WO1979001088A1 (fr) * | 1978-05-18 | 1979-12-13 | Ciba Geigy Ag | Nouveaux derives de la glucosamine silylee et leur procede de preparation |
| FR2477551A1 (fr) * | 1980-03-10 | 1981-09-11 | Anvar | Nouveaux derives de l'a, a'-trehalose et medicaments les contenant |
| WO1981002576A1 (fr) * | 1980-03-10 | 1981-09-17 | Anvar | Nouveaux derives de l'(alpha), (alpha)'-trehalose et medicaments les contenant |
| FR2479000A1 (fr) * | 1980-03-28 | 1981-10-02 | Research Corp | Vaccin contre la brucellose, maladie du betail |
| FR2534259A1 (fr) * | 1982-10-08 | 1984-04-13 | Ss Pharmaceutical Co | Diester d'acide aliphatique a chaine moyenne en positions 6, 6' d'a,a-trehalose et son application en therapeutique |
Also Published As
| Publication number | Publication date |
|---|---|
| BE844272A (fr) | 1977-01-19 |
| FR2319373B1 (enExample) | 1978-12-01 |
| DE2633690A1 (de) | 1977-02-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |