DE1230794B - Verfahren zur Herstellung von niederen N-Alkylderivaten von Neomycinen, deren Additionssalzen bzw. quaternaeren Ammoniumverbindungen - Google Patents
Verfahren zur Herstellung von niederen N-Alkylderivaten von Neomycinen, deren Additionssalzen bzw. quaternaeren AmmoniumverbindungenInfo
- Publication number
- DE1230794B DE1230794B DER34844A DER0034844A DE1230794B DE 1230794 B DE1230794 B DE 1230794B DE R34844 A DER34844 A DE R34844A DE R0034844 A DER0034844 A DE R0034844A DE 1230794 B DE1230794 B DE 1230794B
- Authority
- DE
- Germany
- Prior art keywords
- groups
- carbon atoms
- alkyl
- neomycin
- quaternary ammonium
- 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.)
- Pending
Links
- 229930193140 Neomycin Natural products 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 17
- 150000003856 quaternary ammonium compounds Chemical class 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 13
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 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 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- 235000012000 cholesterol Nutrition 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 18
- 229960004927 neomycin Drugs 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- SYJXFKPQNSDJLI-HKEUSBCWSA-N neamine Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](N)C[C@@H]1N SYJXFKPQNSDJLI-HKEUSBCWSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000003115 biocidal effect Effects 0.000 description 15
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical class N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 14
- 210000004185 liver Anatomy 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 235000013305 food Nutrition 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241000588724 Escherichia coli Species 0.000 description 9
- 241000191967 Staphylococcus aureus Species 0.000 description 9
- PGBHMTALBVVCIT-VZXHOKRSSA-N neomycin C Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VZXHOKRSSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000008098 formaldehyde solution Substances 0.000 description 7
- 229940053050 neomycin sulfate Drugs 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- LXWYVWLCMYCGDA-UHFFFAOYSA-N acetic acid;propan-1-ol;pyridine;hydrate Chemical compound O.CCCO.CC(O)=O.C1=CC=NC=C1 LXWYVWLCMYCGDA-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000001174 ascending effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 6
- 238000004816 paper chromatography Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 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 5
- 150000001450 anions Chemical class 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 229960001767 dextrothyroxine Drugs 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 229960003704 framycetin Drugs 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- -1 20" / Chemical compound 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 238000005932 reductive alkylation reaction Methods 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000003613 bile acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229940034208 thyroxine Drugs 0.000 description 1
- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
-
- 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
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
- C07H15/232—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with at least three saccharide radicals in the molecule, e.g. lividomycin, neomycin, paromomycin
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1279062A GB1033394A (en) | 1962-04-03 | 1962-04-03 | New therapeutic agents |
| GB3895362 | 1962-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1230794B true DE1230794B (de) | 1966-12-22 |
Family
ID=26249267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER34844A Pending DE1230794B (de) | 1962-04-03 | 1963-04-02 | Verfahren zur Herstellung von niederen N-Alkylderivaten von Neomycinen, deren Additionssalzen bzw. quaternaeren Ammoniumverbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US3282783A (en, 2012) |
| BE (1) | BE630462A (en, 2012) |
| CH (1) | CH411240A (en, 2012) |
| DE (1) | DE1230794B (en, 2012) |
| ES (1) | ES286383A1 (en, 2012) |
| FI (1) | FI41016B (en, 2012) |
| FR (1) | FR2676M (en, 2012) |
| NL (1) | NL291070A (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3852264A (en) * | 1969-08-25 | 1974-12-03 | Schering Corp | Gentamicin c oxazolidine derivatives |
| US3860574A (en) * | 1972-12-06 | 1975-01-14 | Bristol Myers Co | Derivatives of neomycin b and neomycin c |
| JPS553358B2 (en, 2012) * | 1973-03-13 | 1980-01-24 | ||
| US4024332A (en) * | 1973-06-05 | 1977-05-17 | Pfizer Inc. | Aminoglycoside antibiotics and intermediates therefor |
| FR2263747B1 (en, 2012) * | 1974-03-12 | 1977-12-02 | Roussel Uclaf | |
| FR2274628A1 (fr) * | 1974-04-11 | 1976-01-09 | Farmaceutici Italia | Derives de la paromomycine et procede pour les preparer |
| US3960838A (en) * | 1974-10-29 | 1976-06-01 | Smithkline Corporation | Mercaptopseudodisaccharides |
| US4048431A (en) * | 1975-09-12 | 1977-09-13 | American Cyanamid Company | Alkylated derivatives of antibiotic BM123γ |
| US4002608A (en) * | 1975-11-04 | 1977-01-11 | Schering Corporation | 1-N-alkyl-aminoglycoside-XK-88 derivatives and methods for their manufacture |
| JPS6011718B2 (ja) * | 1976-09-23 | 1985-03-27 | 協和醗酵工業株式会社 | 新規なホ−テイマイシンｂの誘導体およびその製法 |
| US4124756A (en) * | 1976-12-27 | 1978-11-07 | Abbott Laboratories | 3-DE-O-Methylfortimicins |
| JPS53141244A (en) * | 1977-05-11 | 1978-12-08 | Kyowa Hakko Kogyo Co Ltd | Novel hortemycin derivatives |
| DK308878A (da) * | 1977-08-18 | 1979-02-19 | Pfizer | Aminoglyosidderivater og fremgangsmaader til deres fremstilling |
| JPS5492951A (en) * | 1977-12-29 | 1979-07-23 | Shionogi & Co Ltd | Novel aminoglycoside derivative |
| US4214077A (en) * | 1978-02-21 | 1980-07-22 | Abbott Laboratories | 1-N-Substituted derivatives of seldomycin factor 5 |
| US4877775A (en) * | 1986-06-16 | 1989-10-31 | E. I. Du Pont De Nemours And Company | Polymeric aminosaccharides as antihypercholesterolemic agents |
| US5268168A (en) * | 1990-02-19 | 1993-12-07 | Sakai Engineering Co., Ltd. | Antibacterial and deodorant processing agent and processing method using same |
| FR2967068A1 (fr) * | 2010-11-09 | 2012-05-11 | Univ Joseph Fourier | Derives de 6-amino-desoxyglucosamine et leur utilisation comme agents antibacteriens |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1044806B (de) * | 1956-10-03 | 1958-11-27 | Hoechst Ag | Verfahren zur Herstellung von wasserloeslichen Derivaten der Tetracycline |
| DE1088481B (de) * | 1958-01-29 | 1960-09-08 | American Cyanamid Co | Verfahren zur Herstellung neuer Verbindungen der Tetracyclinreihe |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA671439A (en) * | 1963-10-01 | J. Gottstein William | (n'-tetracyclylmethyl)-kanamycin | |
| US2631143A (en) * | 1947-07-19 | 1953-03-10 | Olin Mathieson | Purification of antibiotics with water soluble salts of water insoluble carboxylic acids |
| US2937117A (en) * | 1953-06-19 | 1960-05-17 | Chimie Atomistique | Process for lowering high blood cholesterol levels |
| US2736725A (en) * | 1954-03-11 | 1956-02-28 | American Cyanamid Co | Complexes of tetracycline antibiotics and preparation of same |
| GB839023A (en) * | 1956-07-27 | 1960-06-29 | Upjohn Co | Improvements in or relating to neomycin derivatives and the manufacture thereof |
| US3057777A (en) * | 1957-10-28 | 1962-10-09 | Lilly Co Eli | Method of reducing cholesterol level of the blood |
| FR1272911A (fr) * | 1958-07-23 | 1961-10-06 | Soc Ind Fab Antibiotiques Sifa | Procédé de préparation de nouveaux dérivés d'antibiotiques basiques |
| US3277078A (en) * | 1963-03-23 | 1966-10-04 | Takeda Chemical Industries Ltd | Zygomycin a1 and zygomycin a2 and their isolation |
-
0
- NL NL291070D patent/NL291070A/xx unknown
- BE BE630462D patent/BE630462A/xx unknown
-
1963
- 1963-03-25 US US267835A patent/US3282783A/en not_active Expired - Lifetime
- 1963-03-25 ES ES286383A patent/ES286383A1/es not_active Expired
- 1963-03-29 FR FR929765A patent/FR2676M/fr not_active Expired
- 1963-04-02 FI FI0610/63A patent/FI41016B/fi active
- 1963-04-02 DE DER34844A patent/DE1230794B/de active Pending
- 1963-04-03 CH CH422363A patent/CH411240A/fr unknown
-
1966
- 1966-07-12 US US564537A patent/US3350387A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1044806B (de) * | 1956-10-03 | 1958-11-27 | Hoechst Ag | Verfahren zur Herstellung von wasserloeslichen Derivaten der Tetracycline |
| DE1088481B (de) * | 1958-01-29 | 1960-09-08 | American Cyanamid Co | Verfahren zur Herstellung neuer Verbindungen der Tetracyclinreihe |
Also Published As
| Publication number | Publication date |
|---|---|
| BE630462A (en, 2012) | |
| FR2676M (fr) | 1964-07-20 |
| NL291070A (en, 2012) | |
| US3282783A (en) | 1966-11-01 |
| FI41016B (en, 2012) | 1969-04-30 |
| CH411240A (fr) | 1966-04-15 |
| ES286383A1 (es) | 1963-12-01 |
| US3350387A (en) | 1967-10-31 |
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