GB1418399A - Antibiotic derivatives - Google Patents
Antibiotic derivativesInfo
- Publication number
- GB1418399A GB1418399A GB1129673A GB1129673A GB1418399A GB 1418399 A GB1418399 A GB 1418399A GB 1129673 A GB1129673 A GB 1129673A GB 1129673 A GB1129673 A GB 1129673A GB 1418399 A GB1418399 A GB 1418399A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- acylating
- tobramycin
- amino
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
-
- 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1418399 Tobramycin derivatives BRISTOL-MYERS CO 8 March 1973 [8 March 1972] 11296/73 Heading C2C Novel antibiotic tobramycin derivatives having the general Formula (IV): and acid addition salts thereof, wherein R<SP>2</SP> is L - (-) - γ - amino - α - hydroxybutyryl, L - (-)- # - amino - α - hydroxypropionyl or L - (-) - #- amino-a-hydroxyvaleryl, are prepared by the consecutive steps of (a) treating tobramycin with an acylating agent selected from compounds having the following formulae: wherein R<SP>4</SP> and R<SP>5</SP> are alike or different and each is H, F, Cl, Br, NO 2 , OH, C 1-6 alkyl or C 1-6 alkoxy, and X is Cl, Br or I, or with a functional N-acylating equivalent of such a compound, in a proportion of up to 1 mole of said agent per mole of tobramycin, to produce an intermediate compound of Formula (II): wherein Y is a group of formula: and R<SP>4</SP> and R<SP>5</SP> are as defined above; (b) acylating the compound (II) with an acylating agent of Formula (VII) in which n is 1, 2 or 3, W is a group of one of the formulae ascribed to Y above, and M is a group of formula or with an N-acylating functional equivalent of such a compound, in a proportion of at least 0À5 mole of said agent per mole of compound (II), to produce a compound of Formula (III): wherein n, y and w are as defined above; and (c) removing the blocking groups y and w, and if desired converting the product (IV) into an acid addition salt, (e.g. the sulphate and disulphate). The inventive compounds (IV) and their non- toxic acid addition salts have antibiotic activity, and may be admixed with pharmaceutically acceptable diluents or carriers to provide antibiotic pharmaceutical compositions.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23297872A | 1972-03-08 | 1972-03-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1418399A true GB1418399A (en) | 1975-12-17 |
Family
ID=22875369
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1129673A Expired GB1418399A (en) | 1972-03-08 | 1973-03-08 | Antibiotic derivatives |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPS5133551B2 (en) |
AR (1) | AR205516A1 (en) |
BE (1) | BE796491A (en) |
FR (1) | FR2181797B1 (en) |
GB (1) | GB1418399A (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1046513A (en) * | 1973-02-23 | 1979-01-16 | Bristol-Myers Squibb Company | Antibiotic derivatives |
JPS5818635B2 (en) * | 1977-01-12 | 1983-04-14 | セイコーエプソン株式会社 | Electronic watch with hygrometer |
CA1105455A (en) * | 1977-09-19 | 1981-07-21 | Junji Irisawa | Aminoglycoside derivatives |
JPS5461151A (en) * | 1977-10-25 | 1979-05-17 | Shionogi & Co Ltd | Novel aminoglycoside derivative |
US4656160A (en) * | 1984-11-29 | 1987-04-07 | Fujisawa Pharmaceutical Co., Ltd. | Aminoglycoside derivatives |
JP2716458B2 (en) * | 1988-06-03 | 1998-02-18 | シチズン時計株式会社 | Clearance adjustment structure of sliding bearing |
JPH02145054U (en) * | 1989-05-13 | 1990-12-10 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT288594B (en) * | 1968-03-25 | 1971-03-10 | Parke Davis & Co | Process for the production of new antibiotic compounds |
-
1973
- 1973-01-01 AR AR24695973A patent/AR205516A1/en active
- 1973-03-07 FR FR7308174A patent/FR2181797B1/fr not_active Expired
- 1973-03-08 BE BE128558A patent/BE796491A/en not_active IP Right Cessation
- 1973-03-08 GB GB1129673A patent/GB1418399A/en not_active Expired
- 1973-03-08 JP JP2663573A patent/JPS5133551B2/ja not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AR205516A1 (en) | 1976-05-14 |
FR2181797B1 (en) | 1976-10-22 |
BE796491A (en) | 1973-09-10 |
FR2181797A1 (en) | 1973-12-07 |
JPS4918850A (en) | 1974-02-19 |
DE2311524B2 (en) | 1975-07-10 |
DE2311524A1 (en) | 1973-09-20 |
JPS5133551B2 (en) | 1976-09-20 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |