CH391679A - Verfahren zur Herstellung neuer Zuckerderivate - Google Patents

Verfahren zur Herstellung neuer Zuckerderivate

Info

Publication number: CH391679A
Authority: CH; Switzerland
Prior art keywords: radicals; hydroxyl groups; glucofuranoside; acids; compounds
Prior art date: 1959-01-10

Application number

CH6817059A

Other languages

German (de)

English (en)

Inventor

Jean Dr Druey

Georg Dr Huber

Original Assignee

Ciba Geigy

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.)

1959-01-10

Filing date

1959-01-10

Publication date

1965-05-15

1959-01-10 Application filed by Ciba Geigy filed Critical Ciba Geigy

1959-01-10 Priority to CH6817059A priority Critical patent/CH391679A/de

1959-12-21 Priority to DK462859AA priority patent/DK126687B/da

1959-12-30 Priority to US862799A priority patent/US3157634A/en

1959-12-30 Priority to DE19591792718 priority patent/DE1792718A1/de

1959-12-30 Priority to DE19591443591 priority patent/DE1443591A1/de

1959-12-30 Priority to DE19591792716 priority patent/DE1792716A1/de

1959-12-30 Priority to DE19591418126 priority patent/DE1418126A1/de

1959-12-31 Priority to ES0254705A priority patent/ES254705A1/es

1959-12-31 Priority to GB44483/59A priority patent/GB909278A/en

1959-12-31 Priority to GB1962/61A priority patent/GB909279A/en

1960-01-08 Priority to BE586370A priority patent/BE586370A/fr

1960-01-08 Priority to BE586369A priority patent/BE586369A/fr

1960-01-08 Priority to BE586371A priority patent/BE586371A/fr

1960-01-08 Priority to AT12660A priority patent/AT241483B/de

1960-01-09 Priority to SE178/60A priority patent/SE301637B/xx

1960-08-29 Priority to FR836981A priority patent/FR348M/fr

1960-11-03 Priority to DK434960AA priority patent/DK127056B/da

1965-03-30 Priority to SE04079/65A priority patent/SE332974B/xx

1965-05-15 Publication of CH391679A publication Critical patent/CH391679A/de

1966-12-31 Priority to MY196616A priority patent/MY6600016A/xx

Links

238000000034 method Methods 0.000 title claims description 11
150000001875 compounds Chemical class 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 6
-1 heterocyclic carboxylic acids Chemical class 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
150000002989 phenols Chemical class 0.000 claims description 3
238000006266 etherification reaction Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 2
229940100198 alkylating agent Drugs 0.000 claims 1
239000002168 alkylating agent Substances 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000009835 boiling Methods 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
238000003756 stirring Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
BGGCXQKYCBBHAH-OZRXBMAMSA-N (1r)-1-[(3ar,5r,6s,6ar)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol Chemical compound O1[C@H]([C@H](O)CO)[C@H](O)[C@H]2OC(C)(C)O[C@H]21 BGGCXQKYCBBHAH-OZRXBMAMSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
MIPWIPFSFNFSBO-MCIOHCJDSA-N CCOC([C@@H]1O)O[C@H]([C@@](C)(C(C)O)O)[C@]1(C)O Chemical compound CCOC([C@@H]1O)O[C@H]([C@@](C)(C(C)O)O)[C@]1(C)O MIPWIPFSFNFSBO-MCIOHCJDSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000002955 isolation Methods 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
229940124530 sulfonamide Drugs 0.000 description 2
150000003456 sulfonamides Chemical class 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
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 1
206010002199 Anaphylactic shock Diseases 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
LSHXJSOJQYVSPT-FPPQFYMJSA-N CCOC([C@]1(C(C)=O)O)O[C@H]([C@@](C)(C(C)O)O)[C@]1(C)O Chemical group CCOC([C@]1(C(C)=O)O)O[C@H]([C@@](C)(C(C)O)O)[C@]1(C)O LSHXJSOJQYVSPT-FPPQFYMJSA-N 0.000 description 1
OKJLHVWAPXWZOL-FVQVIHIZSA-N CCOC([C@]1(C(C)=O)O)O[C@H]([C@@](CC2=CC=CC=C2)(C(CC2=CC=CC=C2)O)O)[C@]1(CC1=CC=CC=C1)O Chemical compound CCOC([C@]1(C(C)=O)O)O[C@H]([C@@](CC2=CC=CC=C2)(C(CC2=CC=CC=C2)O)O)[C@]1(CC1=CC=CC=C1)O OKJLHVWAPXWZOL-FVQVIHIZSA-N 0.000 description 1
CZXFKJWASIFHJK-FPPQFYMJSA-N CCOC([C@]1(CC(O)=O)O)O[C@H]([C@@](C)(C(C)O)O)[C@]1(C)O Chemical compound CCOC([C@]1(CC(O)=O)O)O[C@H]([C@@](C)(C(C)O)O)[C@]1(C)O CZXFKJWASIFHJK-FPPQFYMJSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
230000001986 anti-endotoxic effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000035876 healing Effects 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229960004738 nicotinyl alcohol Drugs 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical group OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings

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)

CH6817059A 1959-01-10 1959-01-10 Verfahren zur Herstellung neuer Zuckerderivate CH391679A (de)

Priority Applications (19)

Application Number	Priority Date	Filing Date	Title
CH6817059A CH391679A (de)	1959-01-10	1959-01-10	Verfahren zur Herstellung neuer Zuckerderivate
DK462859AA DK126687B (da)	1959-01-10	1959-12-21	Analogifremgangsmåde til fremstilling af glucofuranosider eller 2-0-acylderivater deraf.
US862799A US3157634A (en)	1959-01-10	1959-12-30	Glucofuranosides and process for their preparation
DE19591792718 DE1792718A1 (de)	1959-01-10	1959-12-30	Pharmazeutische Praeparate enthaltende Glucofuranoside
DE19591443591 DE1443591A1 (de)	1959-01-10	1959-12-30	Glucofuranoside und Verfahren zu ihrer Herstellung
DE19591792716 DE1792716A1 (de)	1959-01-10	1959-12-30	Pharmazeutische Praeparate,enthaltend Glucofuranoside
DE19591418126 DE1418126A1 (de)	1959-01-10	1959-12-30	Glucofuranoside und Verfahren zu deren Herstellung
GB1962/61A GB909279A (en)	1959-01-10	1959-12-31	Pharmaceutical preparations containing d-glucofuranosides
GB44483/59A GB909278A (en)	1959-01-10	1959-12-31	New sugar derivatives, a process for their manufacture and pharmaceutical preparations containing them
ES0254705A ES254705A1 (es)	1959-01-10	1959-12-31	Procedimiento para la obtenciën de nuevos derivados del azucar
BE586370A BE586370A (fr)	1959-01-10	1960-01-08	Procédé de préparation de 1-amino (secondaire)-1-désoxy-cétoses
BE586369A BE586369A (fr)	1959-01-10	1960-01-08	Procédé de préparation de nouveaux glucofuranosides 3,5,6-substitués
BE586371A BE586371A (fr)	1959-01-10	1960-01-08	Dérivés asymétriques d'alkylènediamines leur préparation et leur utilisation
AT12660A AT241483B (de)	1959-01-10	1960-01-08	Verfahren zur Herstellung neuer Zuckerderivate
SE178/60A SE301637B (fr)	1959-01-10	1960-01-09
FR836981A FR348M (fr)	1959-01-10	1960-08-29	Nouveau glucofuranoside 3,5,6-substitué utilisable en thérapeutique.
DK434960AA DK127056B (da)	1959-01-10	1960-11-03	Analogifremgangsmåde til fremstilling af glucofuranosider.
SE04079/65A SE332974B (fr)	1959-01-10	1965-03-30
MY196616A MY6600016A (en)	1959-01-10	1966-12-31	New sugar derivatives, a process for their manufacture and pharmaceutical preparations containing them

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6817059A CH391679A (de)	1959-01-10	1959-01-10	Verfahren zur Herstellung neuer Zuckerderivate

Publications (1)

Publication Number	Publication Date
CH391679A true CH391679A (de)	1965-05-15

Family

ID=4528520

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6817059A CH391679A (de)	1959-01-10	1959-01-10	Verfahren zur Herstellung neuer Zuckerderivate

Country Status (2)

Country	Link
BE (2)	BE586371A (fr)
CH (1)	CH391679A (fr)

1959
- 1959-01-10 CH CH6817059A patent/CH391679A/de unknown
1960
- 1960-01-08 BE BE586371A patent/BE586371A/fr unknown
- 1960-01-08 BE BE586370A patent/BE586370A/fr unknown

Also Published As

Publication number	Publication date
BE586371A (fr)	1960-07-08
BE586370A (fr)	1960-07-08

Publication	Publication Date	Title
DE1418126A1 (de)	1969-12-04	Glucofuranoside und Verfahren zu deren Herstellung
CH416600A (de)	1966-07-15	Verfahren zur Herstellung von Farnesylessigsäureestern
DE1244777B (de)	1967-07-20	Verfahren zur Herstellung von 7alpha-Methyl-16alpha-hydroxy-oestron bzw. -3, 16-diacetat
CH499507A (de)	1970-11-30	Verfahren zur Herstellung von Aldehyden der Pregnanreihe und ihrer Derivate
CH505815A (de)	1971-04-15	Verfahren zur Herstellung von Furanverbindungen
CH391679A (de)	1965-05-15	Verfahren zur Herstellung neuer Zuckerderivate
DE953077C (de)	1956-11-29	Verfahren zur Herstellung von 5-Pregnen-17ª, 21-diol-3, 11, 20-trion-3, 20-dialkylen-ketalen
CH544752A (de)	1974-01-15	Verfahren zur Herstellung neuer Glucoside
DE1793462B2 (de)	1979-06-07	N-Aryl-anthranilsäureester monosubstituierter gem-Diole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate
DE1418126C (de)	1972-04-27	Glucofuranoside, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE2319873C2 (de)	1982-06-16	16-O-Alkylderivate von Gitoxigenin-digitoxosiden, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE1443591C (de)	1972-05-31	Glucofuranoside, Verfahren zu ihrer Herstellung und diese enthaltende pharma zeutische Präparate
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AT217645B (de)	1961-10-10	Verfahren zur Herstellung von neuen Derivaten des Aldosterons
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CH540892A (de)	1973-08-31	Verfahren zur Herstellung von Aldehyden der Pregnanreihe und ihrer Derivate
AT224116B (de)	1962-11-12	Verfahren zur Herstellung von neuen, 4-substituierten 1,2-Diaryl-3,5-dioxo-pyrazolidinen
CH553770A (de)	1974-09-13	Verfahren zur herstellung von aldehyden der pregnanreihe und ihrer derivate.
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CH598156A5 (en)	1978-04-28	2-chloro-pregnane-21-aldehyde derivs
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