GB1494129A - Derivatives of diaminocyclitols and methods for their preparation - Google Patents
Derivatives of diaminocyclitols and methods for their preparationInfo
- Publication number
- GB1494129A GB1494129A GB2653/75A GB265375A GB1494129A GB 1494129 A GB1494129 A GB 1494129A GB 2653/75 A GB2653/75 A GB 2653/75A GB 265375 A GB265375 A GB 265375A GB 1494129 A GB1494129 A GB 1494129A
- Authority
- GB
- United Kingdom
- Prior art keywords
- gentamicin
- antibiotic
- amino
- diaminocyclitols
- aminoglycosyl
- 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
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
The 1-N-X-substituted 4,6-di(aminoglycosyl)-1,3-diaminocyclitols gentamicin A, gentamicin B, gentamicin B1, gentamicin C1, gentamicin C1a, gentamicin C2, gentamicin C2a, gentamicin X2, sisomicin, verdamicin, antibiotic G-418, antibiotic 66-40B, antibiotic 66-40D, antibiotic JI-20A, antibiotic JI-20B and antibiotic G-52, in which X is the S-3-amino-2-hydroxypropionyl or S-4-amino-2-hydroxybutyl group, are prepared. (In the case of gentamicins C1, C1a and C2, X is restricted to S-3-amino-2-hydroxypropionyl.) Owing to the presence of the 1-N-substituent, these compounds have greater activity. The process comprises reacting a 1-N-unsubstituted 4,6-di(aminoglycosyl)-1,3-diaminocyclitol, which may be in the form of a partially neutralised acid addition salt, with an appropriate acid in the presence of a carbodiimide or with a functional derivative of this acid. During the process it is possible for amino groups and/or the hydroxyl group, with the exception of the 1-amino group, in the starting materials to undergo intermediate protection.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45257174A | 1974-03-19 | 1974-03-19 | |
US05/452,586 US4029882A (en) | 1974-03-19 | 1974-03-19 | Selective acylation of the C-1 amino group of aminoglycoside antibiotics |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1494129A true GB1494129A (en) | 1977-12-07 |
Family
ID=27036813
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2653/75A Expired GB1494129A (en) | 1974-03-19 | 1975-01-21 | Derivatives of diaminocyclitols and methods for their preparation |
Country Status (10)
Country | Link |
---|---|
AR (1) | AR207582A1 (en) |
BG (1) | BG26400A3 (en) |
CH (1) | CH612946A5 (en) |
DE (1) | DE2502296C2 (en) |
FR (1) | FR2264553B1 (en) |
GB (1) | GB1494129A (en) |
HK (1) | HK7681A (en) |
IE (1) | IE40796B1 (en) |
IL (1) | IL46467A (en) |
MY (1) | MY8100350A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010132770A1 (en) * | 2009-05-14 | 2010-11-18 | Achaogen, Inc. | Treatment of klebsiella pneumoniae infections with antibacterial aminoglycoside compounds |
US8383596B2 (en) | 2007-11-21 | 2013-02-26 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8492354B2 (en) | 2009-05-15 | 2013-07-23 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8524689B2 (en) | 2009-05-15 | 2013-09-03 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8524675B2 (en) | 2009-05-15 | 2013-09-03 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8653042B2 (en) | 2009-05-15 | 2014-02-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8658606B2 (en) | 2009-05-15 | 2014-02-25 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US9073958B2 (en) | 2006-04-03 | 2015-07-07 | Technion Research & Development Foundation Limited | Aminoglycosides and uses thereof in the treatment of genetic disorders |
Families Citing this family (4)
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 |
DE2753769A1 (en) * | 1977-12-02 | 1979-06-13 | Bayer Ag | 1-N-4,6-DI-O- (AMINOGLYCOSYL) -1,3-DIAMINO-CYCLITOL DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND USE |
DE2921973A1 (en) * | 1979-05-30 | 1980-12-11 | Bayer Ag | SISOMICIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
DE3101376A1 (en) * | 1981-01-17 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | SISOMICIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
-
1975
- 1975-01-01 AR AR257371A patent/AR207582A1/en active
- 1975-01-21 IL IL46467A patent/IL46467A/en unknown
- 1975-01-21 GB GB2653/75A patent/GB1494129A/en not_active Expired
- 1975-01-21 FR FR7501799A patent/FR2264553B1/fr not_active Expired
- 1975-01-21 DE DE2502296A patent/DE2502296C2/en not_active Expired
- 1975-01-21 IE IE115/75A patent/IE40796B1/en unknown
- 1975-01-22 CH CH77275A patent/CH612946A5/en not_active IP Right Cessation
- 1975-01-24 BG BG7528804A patent/BG26400A3/xx unknown
-
1981
- 1981-03-12 HK HK76/81A patent/HK7681A/en unknown
- 1981-12-30 MY MY350/81A patent/MY8100350A/en unknown
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10159689B2 (en) | 2006-04-03 | 2018-12-25 | Technion Research & Development Foundation Limited | Aminoglycosides and uses thereof in the treatment of genetic disorders |
US9821001B2 (en) | 2006-04-03 | 2017-11-21 | Technion Research & Development Foundation Limited | Aminoglycosides and uses thereof in the treatment of genetic disorders |
US9073958B2 (en) | 2006-04-03 | 2015-07-07 | Technion Research & Development Foundation Limited | Aminoglycosides and uses thereof in the treatment of genetic disorders |
US9266919B2 (en) | 2007-11-21 | 2016-02-23 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8383596B2 (en) | 2007-11-21 | 2013-02-26 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US11117915B2 (en) | 2007-11-21 | 2021-09-14 | Cipla USA, Inc. | Antibacterial aminoglycoside analogs |
US9688711B2 (en) | 2007-11-21 | 2017-06-27 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8822424B2 (en) | 2007-11-21 | 2014-09-02 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
WO2010132770A1 (en) * | 2009-05-14 | 2010-11-18 | Achaogen, Inc. | Treatment of klebsiella pneumoniae infections with antibacterial aminoglycoside compounds |
US8524689B2 (en) | 2009-05-15 | 2013-09-03 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8658606B2 (en) | 2009-05-15 | 2014-02-25 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8653042B2 (en) | 2009-05-15 | 2014-02-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8524675B2 (en) | 2009-05-15 | 2013-09-03 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
USRE47741E1 (en) | 2009-05-15 | 2019-11-26 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
US8492354B2 (en) | 2009-05-15 | 2013-07-23 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
Also Published As
Publication number | Publication date |
---|---|
MY8100350A (en) | 1981-12-31 |
IE40796L (en) | 1975-09-19 |
FR2264553B1 (en) | 1978-12-01 |
DE2502296C2 (en) | 1983-09-22 |
CH612946A5 (en) | 1979-08-31 |
HK7681A (en) | 1981-03-20 |
AR207582A1 (en) | 1976-10-15 |
AU7747775A (en) | 1976-07-22 |
FR2264553A1 (en) | 1975-10-17 |
IL46467A (en) | 1978-10-31 |
BG26400A3 (en) | 1979-03-15 |
DE2502296A1 (en) | 1975-09-25 |
IE40796B1 (en) | 1979-08-15 |
IL46467A0 (en) | 1975-04-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee | ||
704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19950120 |