GB839023A - Improvements in or relating to neomycin derivatives and the manufacture thereof - Google Patents
Improvements in or relating to neomycin derivatives and the manufacture thereofInfo
- Publication number
- GB839023A GB839023A GB21742/57A GB2174257A GB839023A GB 839023 A GB839023 A GB 839023A GB 21742/57 A GB21742/57 A GB 21742/57A GB 2174257 A GB2174257 A GB 2174257A GB 839023 A GB839023 A GB 839023A
- Authority
- GB
- United Kingdom
- Prior art keywords
- neomycin
- hexa
- base
- schiff
- nitrobenzylidene
- 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
Links
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
- C07H15/20—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)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A neomycin Schiff's base having similar biological properties to the parent neomycin and being water-insoluble, is obtained from an aldehyde of formula <FORM:0839023/IV (b)/1> wherein R and R1 are the same or different and each represent hydrogen or an alkyl, 1 to 8 carbon, alkoxy, hydroxy, halogen or nitro group and neomycin B, neomycin C, or mixtures thereof. The reaction takes place in an inert solvent, e.g. water, alkanol or aqueous alkanol, at pH 8.5 to 12, between 5 and 10 molar equivalents of the aromatic aldehyde being used for each mol. of the neomycin compound. The Schiff's base may be used as such for the treatment of humans and animals, or may be converted to the corresponding mineral acid salt of neomycin by dissolving in an inert solvent such as acetone or alcohol, and adding a mineral acid such as hydrochloric, sulphuric, hydrobromic or phosphoric acids. The base may be used in the purification and isolation of neomycin from a clarified fermentation broth by adjusting to pH 8.5 to 12, adding the aromatic aldehyde and filtering off the precipitated Schiff's base. Examples describe the preparation of (a) hexasalicylidene neomycin B; (b) hexabenzylidene neomycin B and its catalytic hydrogenation to hexa-N-benzylneomycin B; (c) tetra-m-nitrobenzylidene neomycin B; (d) hexa-3,4-diethoxybenzylidene neomycin B; (e) hexa-p-methoxybenzylidene neomycin B; (f) hexa-p-nitrobenzylidene neomycin B; (g) hexa-1-naphthylidene neomycin B; (h) hexa-o-methoxybenzylidene neomycin B; and (i) hexa-2,4-dichlorobenzylidene neomycin B.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US839023XA | 1956-07-27 | 1956-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB839023A true GB839023A (en) | 1960-06-29 |
Family
ID=22181384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21742/57A Expired GB839023A (en) | 1956-07-27 | 1957-07-09 | Improvements in or relating to neomycin derivatives and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB839023A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3154537A (en) * | 1962-04-02 | 1964-10-27 | Olin Mathieson | Neomycin purification |
| US3282783A (en) * | 1962-04-03 | 1966-11-01 | Rit Rech Ind Therapeut | Method for causing hypocholesterolemic activity in animals with poly-n-lower alkyl derivatives of polyamino antibiotics |
-
1957
- 1957-07-09 GB GB21742/57A patent/GB839023A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3154537A (en) * | 1962-04-02 | 1964-10-27 | Olin Mathieson | Neomycin purification |
| US3282783A (en) * | 1962-04-03 | 1966-11-01 | Rit Rech Ind Therapeut | Method for causing hypocholesterolemic activity in animals with poly-n-lower alkyl derivatives of polyamino antibiotics |
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