GB1467401A - Kanamycin derivatives - Google Patents
Kanamycin derivativesInfo
- Publication number
- GB1467401A GB1467401A GB819374A GB819374A GB1467401A GB 1467401 A GB1467401 A GB 1467401A GB 819374 A GB819374 A GB 819374A GB 819374 A GB819374 A GB 819374A GB 1467401 A GB1467401 A GB 1467401A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- reacting
- amino
- kanamycin
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1467401 Acylated kanamycins BRISTOLMYERS CO 22 Feb 1974 [23 Feb 1973 (2)] 8193/74 Addition to 1401221 Heading C2C Novel acylated kanamycins of the general formula wherein R<SP>3</SP> is OH or NH 2 and R<SP>2</SP> is L-(-)-#- amino - α - hydroxypropionyl or L - (-) - 8- amino-α-hydroxyvaleryl, and pharmaceutically acceptable acid addition salts thereof, are prepared by reacting kanamycin A or B (1 mole) with a compound having one of the following general formulµ wherein each of R<SP>4</SP> and R<SP>5</SP> is H, F, Cl, Br, NO 2 , OH, alkyl or alkoxy and X is Cl, Br or I (up to 1 mole) at below 50‹ C., acylating the resulting N-substituted kanamycin of the general formula wherein Y is a group having one of the following general formulµ with a compound of the general formula WNH(CH 2 ) n CH(OH)COM, wherein n is 1 or 3, W is as Y and M is a group having one of the following formulµ (molar ratio 1 : at least 0À5) and removing the blocking groups W and Y from the resulting di-N-substituted kanamycin of the general formula followed optionally by salification of the product. The N-hydroxysuccinimide esters of L-#- benzyloxycarbonylamino - α - hydroxypropionic and L - # - benzyloxycarbonylamino - α - hydroxyvaleric acid are prepared by reacting L-#-amino- α-hydroxypropionic acid or L-#-amino-α-hydroxyvaleric acid with carbobenzoxy chloride in the presence of NaOH and reacting the resulting benzyloxycarbonylamino derivative with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide. N-Bemyloxycarbonyloxy-succinimide is prepared by reacting N-hydroxysuccinimide with carbobenzoxy chloride in the presence of NaOH. Pharmaceutical compositions having antibacterial activity comprise, as active ingredient, an acylated kanamycin of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US335210A US3886139A (en) | 1973-02-23 | 1973-02-23 | Derivatives of kanamycin |
US335211A US3904597A (en) | 1973-02-23 | 1973-02-23 | Antibiotic derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1467401A true GB1467401A (en) | 1977-03-16 |
Family
ID=26989599
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB819374A Expired GB1467401A (en) | 1973-02-23 | 1974-02-22 | Kanamycin derivatives |
Country Status (9)
Country | Link |
---|---|
JP (1) | JPS553360B2 (en) |
CA (1) | CA1046513A (en) |
CH (1) | CH599243A5 (en) |
DE (1) | DE2408666C3 (en) |
DK (1) | DK140259B (en) |
FR (1) | FR2218879B2 (en) |
GB (1) | GB1467401A (en) |
NL (1) | NL7402456A (en) |
SE (1) | SE417972B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5512038B2 (en) * | 1973-05-15 | 1980-03-29 | ||
EP0000473B1 (en) * | 1977-06-24 | 1981-03-11 | Scherico Ltd. | Process for preparing aminoglycoside derivatives, novel derivatives obtained and pharmaceutical compositions containing such derivatives |
US9981896B2 (en) | 2016-07-01 | 2018-05-29 | Res Usa, Llc | Conversion of methane to dimethyl ether |
US10189763B2 (en) | 2016-07-01 | 2019-01-29 | Res Usa, Llc | Reduction of greenhouse gas emission |
US9938217B2 (en) | 2016-07-01 | 2018-04-10 | Res Usa, Llc | Fluidized bed membrane reactor |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR205516A1 (en) * | 1972-03-08 | 1976-05-14 | Bristol Myers Co | PROCESS FOR THE PREPARATION OF TOBRAMYCIN DERIVATIVES |
-
1974
- 1974-02-21 SE SE7402334A patent/SE417972B/en not_active IP Right Cessation
- 1974-02-21 CA CA193,107A patent/CA1046513A/en not_active Expired
- 1974-02-22 DK DK98674AA patent/DK140259B/en not_active IP Right Cessation
- 1974-02-22 CH CH256474A patent/CH599243A5/xx not_active IP Right Cessation
- 1974-02-22 DE DE2408666A patent/DE2408666C3/en not_active Expired
- 1974-02-22 FR FR7406232A patent/FR2218879B2/fr not_active Expired
- 1974-02-22 GB GB819374A patent/GB1467401A/en not_active Expired
- 1974-02-22 JP JP2042674A patent/JPS553360B2/ja not_active Expired
- 1974-02-22 NL NL7402456A patent/NL7402456A/xx not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
DE2408666B2 (en) | 1978-02-16 |
AU6587574A (en) | 1975-08-21 |
CA1046513A (en) | 1979-01-16 |
FR2218879B2 (en) | 1978-05-26 |
DE2408666A1 (en) | 1974-09-12 |
DE2408666C3 (en) | 1978-10-19 |
JPS504043A (en) | 1975-01-16 |
DK140259C (en) | 1979-12-10 |
SE417972B (en) | 1981-04-27 |
CH599243A5 (en) | 1978-05-31 |
DK140259B (en) | 1979-07-16 |
FR2218879A2 (en) | 1974-09-20 |
JPS553360B2 (en) | 1980-01-24 |
NL7402456A (en) | 1974-08-27 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed |