GB1499041A - Derivatives of kanamycin - Google Patents
Derivatives of kanamycinInfo
- Publication number
- GB1499041A GB1499041A GB10349/75A GB1034975A GB1499041A GB 1499041 A GB1499041 A GB 1499041A GB 10349/75 A GB10349/75 A GB 10349/75A GB 1034975 A GB1034975 A GB 1034975A GB 1499041 A GB1499041 A GB 1499041A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- kanamycin
- hydroxybutyryl
- alkyl
- pharmaceutically acceptable
- 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
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1499041 1 - N - (L - 4 - Amino - 2 - hydroxybutyryl) - 6<SP>1</SP> - N - alkyl - kanamycins A ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI 12 March 1975 [22 March 1974] 10349/75 Heading C2C Novel 1 - N - (L - 4 - amino - 2 - hydroxybutyryl)-6<SP>1</SP>-N-alkyl kanamycins A of the general formula wherein R is a C 1-4 alkyl group, and pharmaceutically acceptable acid addition salt thereof are prepared by acylating the 1-amino group of kanamycin A with L-4-amino-2-hydroxybutyric acid or a functional equivalent thereof and alkylating the 61-amino group (amino and hydroxyl groups not involved in the reactions are optionally protected, the protecting group(s) being subsequently removed), followed optionally by salification of the product. Examples of intermediates obtained in the above process are 6<SP>1</SP>-N-t-butoxycarbonylkanamycin A (prepared by reacting kanamycin A with t-butoxycarbonyl azide) and 3,3<SP>1</SP>-di-N- benzyloxycarbonyl - 1 - mono - N - (L - 4 - benzyloxycarbonylamino - 2 - hydroxybutyryl)kanamycin A (prepared by treating 6<SP>1</SP>-N-t-butoxycarbonylkanamycin A with the N-hydroxysuccinimide ester of L-4-benzyloxycarbonylamino-2-hydroxybutyric acid, followed by benzyloxycarbonyl chloride and then 90% trifluoroacetic acid). Pharmaceutical compositons having antibacterial activity comprise, as active ingredient, a 1 - N - (L - 4 - amino - 2 - hydroxybutyryl) - 6<SP>1</SP>- N-alkyl-kanamycin A of the general formula above or a pharmaceutically acceptable acid addition salt thereof, in combination with a pharmaceutically acceptable carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3154874A JPS5512039B2 (en) | 1974-03-22 | 1974-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1499041A true GB1499041A (en) | 1978-01-25 |
Family
ID=12334229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10349/75A Expired GB1499041A (en) | 1974-03-22 | 1975-03-12 | Derivatives of kanamycin |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5512039B2 (en) |
| DE (1) | DE2512587C3 (en) |
| FR (1) | FR2264556B1 (en) |
| GB (1) | GB1499041A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4136254A (en) * | 1976-06-17 | 1979-01-23 | Schering Corporation | Process of selectively blocking amino functions in aminoglycosides using transition metal salts and intermediates used thereby |
| DE2861947D1 (en) * | 1977-06-10 | 1982-09-02 | Bayer Ag | Selectively protected 4,6-di-o-(aminoglycosyl)-1,3-diamino-cyclitols |
| US4282350A (en) * | 1977-08-05 | 1981-08-04 | Schering Corporation | Selective 3"-N-acylation of 1,3"-di-N-unprotected-poly-N-protected-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols |
-
1974
- 1974-03-22 JP JP3154874A patent/JPS5512039B2/ja not_active Expired
-
1975
- 1975-03-12 GB GB10349/75A patent/GB1499041A/en not_active Expired
- 1975-03-21 DE DE2512587A patent/DE2512587C3/en not_active Expired
- 1975-03-21 FR FR7509559A patent/FR2264556B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2264556B1 (en) | 1978-08-04 |
| JPS5512039B2 (en) | 1980-03-29 |
| DE2512587A1 (en) | 1975-09-25 |
| DE2512587B2 (en) | 1979-11-08 |
| JPS50140420A (en) | 1975-11-11 |
| FR2264556A1 (en) | 1975-10-17 |
| DE2512587C3 (en) | 1980-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |