GB1473733A - Pseudotrisaccharides and methods for their production - Google Patents
Pseudotrisaccharides and methods for their productionInfo
- Publication number
- GB1473733A GB1473733A GB3396874A GB3396874A GB1473733A GB 1473733 A GB1473733 A GB 1473733A GB 3396874 A GB3396874 A GB 3396874A GB 3396874 A GB3396874 A GB 3396874A GB 1473733 A GB1473733 A GB 1473733A
- Authority
- GB
- United Kingdom
- Prior art keywords
- gentamicin
- antibiotic
- mutamicin
- 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
-
- 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
- C07H15/236—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 saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
1473733 Pseudo trisaccharides SCHERICO Ltd 1 Aug 1974 [6 Aug 1973 19 March 1974 (2)] 33968/74 Heading C2C The invention comprises 1-N substituted derivatives of the 4,5-di-(aminoglycosyl)-1,3- diaminocyclitols gentamicin A, gentamicin B, gentamicin B 1 , gentamicin C 1 , gentamicin C 1a , gentamicin C 2 , gentamicin C 2a , gentamicin C 2b , gentamicin X 2 , sisomicin, vendamicin, tobramycin, Antibiotic G-418, Antibiotic 66-40B, Antibiotic 66-40D, Antibiotic J1-20A, Antibiotic J1-20B, Antibiotic G-52, mutamicin 1, mutamicin 2, mutamicin 4, mutamicin 5 and mutamicin 6, where the substituent is -CH 2 X with X being hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, aminohydroxyalkyl, N-alkylaminohydroxyalkyl, phenyl, benzyl or tolyl, said aliphatic radicals having up to seven carbon atoms and, if substituted by amino and hydroxy, bearing the substituents on different C atoms and pharmaceutically acceptable acid addition salts thereof. The compounds of the invention may be prepared by treating one of the above named 4,6-di-(aminoglycosyl)-1,3- diaminocyclitols which may have aminoprotecting groups at any position other than position 1, with an aldehyde of formula X<SP>1</SP>-CHO, with X<SP>1</SP> being a group as defined for X above wherein any amino or hydroxy group present may be protected in the presence of a hydride donor and reducing agent and, if required, removing all protecting groups present in the molecule the last process step being followed by isolating the derivative as such or as a pharmaceutically acceptable acid addition salt.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38575173A | 1973-08-06 | 1973-08-06 | |
| US45260074A | 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 |
|---|---|
| GB1473733A true GB1473733A (en) | 1977-05-18 |
Family
ID=27409729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3396874A Expired GB1473733A (en) | 1973-08-06 | 1974-08-01 | Pseudotrisaccharides and methods for their production |
Country Status (20)
| Country | Link |
|---|---|
| AR (1) | AR215834A1 (en) |
| BE (1) | BE818431A (en) |
| BG (1) | BG25804A3 (en) |
| CH (1) | CH606076A5 (en) |
| CY (1) | CY1018A (en) |
| DD (1) | DD119037A5 (en) |
| DE (2) | DE2462485C2 (en) |
| DK (1) | DK146298C (en) |
| FI (1) | FI62100C (en) |
| FR (1) | FR2240015B1 (en) |
| GB (1) | GB1473733A (en) |
| HK (1) | HK55179A (en) |
| IE (1) | IE40437B1 (en) |
| IL (1) | IL45385A (en) |
| KE (1) | KE2981A (en) |
| LU (1) | LU70661A1 (en) |
| MY (1) | MY8000090A (en) |
| NL (1) | NL171587C (en) |
| NO (1) | NO139483C (en) |
| SE (1) | SE424994B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2293383B (en) * | 1993-04-23 | 1997-02-26 | Jiangsu Inst Microbiology | Method of preparing 1-N-ethylgentamicin derivatives |
| CN101575311B (en) * | 2009-06-19 | 2011-05-04 | 无锡好芳德药业有限公司 | Method for preparing epiphysin |
| 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 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217446A (en) | 1974-10-26 | 1980-08-12 | Pfizer Inc. | ωAmino-2-hydroxyalkyl derivatives of aminoglycoside antibiotics |
| GB1464401A (en) * | 1974-10-26 | 1977-02-16 | Pfizer Ltd | Aminoglycosides |
| FR2405266A1 (en) * | 1975-09-08 | 1979-05-04 | Scherico Ltd | Antibacterial desoxystreptamines - esp 5-epi-4,6-di-(aminoglycosyl)-2-desoxystreptamines and 5-epi-(amino or azido)-5-desoxy derivs |
| US4190722A (en) * | 1977-06-10 | 1980-02-26 | Bayer Aktiengesellschaft | 4,6-Di-O-(aminoglycosyl)-1,3-diaminocyclitols, process for their production and their use |
| 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 |
| JPS5492951A (en) * | 1977-12-29 | 1979-07-23 | Shionogi & Co Ltd | Novel aminoglycoside derivative |
| JPS5538345A (en) * | 1978-09-11 | 1980-03-17 | Shionogi & Co Ltd | Novel aminoglycoside derivative |
| DE2840907A1 (en) * | 1978-09-20 | 1980-04-03 | Bayer Ag | SELECTIVELY PROTECTED 4,6-DI-O- (AMINOGLYKOSYL) -1,3-DIAMINOCYCLITOLE |
| DE2928183A1 (en) * | 1979-07-12 | 1981-01-29 | Bayer Ag | 1-N-ALKYLSISOMICIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235311B (en) | 1963-03-25 | 1967-03-02 | Roussel Uclaf | Process for the production of N-monophenylaethylneomycin B or its therapeutically acceptable salts |
-
1974
- 1974-07-31 CH CH1060274A patent/CH606076A5/xx not_active IP Right Cessation
- 1974-08-01 AR AR255007A patent/AR215834A1/en active
- 1974-08-01 GB GB3396874A patent/GB1473733A/en not_active Expired
- 1974-08-01 NL NLAANVRAGE7410363,A patent/NL171587C/en not_active IP Right Cessation
- 1974-08-01 DE DE2462485A patent/DE2462485C2/en not_active Expired
- 1974-08-01 SE SE7409946A patent/SE424994B/en not_active IP Right Cessation
- 1974-08-01 DE DE2437160A patent/DE2437160C3/en not_active Expired
- 1974-08-01 FR FR7426815A patent/FR2240015B1/fr not_active Expired
- 1974-08-01 NO NO742787A patent/NO139483C/en unknown
- 1974-08-01 IE IE1638/74A patent/IE40437B1/en not_active IP Right Cessation
- 1974-08-01 CY CY1018A patent/CY1018A/en unknown
- 1974-08-01 DK DK412474A patent/DK146298C/en not_active IP Right Cessation
- 1974-08-01 FI FI2304/74A patent/FI62100C/en active
- 1974-08-02 BE BE147234A patent/BE818431A/en not_active IP Right Cessation
- 1974-08-02 IL IL45385A patent/IL45385A/en unknown
- 1974-08-02 LU LU70661A patent/LU70661A1/xx unknown
- 1974-08-05 DD DD180344A patent/DD119037A5/xx unknown
- 1974-08-06 BG BG7400027440A patent/BG25804A3/en unknown
-
1979
- 1979-07-09 KE KE2981A patent/KE2981A/en unknown
- 1979-08-09 HK HK551/79A patent/HK55179A/en unknown
-
1980
- 1980-12-30 MY MY90/80A patent/MY8000090A/en unknown
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2293383B (en) * | 1993-04-23 | 1997-02-26 | Jiangsu Inst Microbiology | Method of preparing 1-N-ethylgentamicin derivatives |
| US8822424B2 (en) | 2007-11-21 | 2014-09-02 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US11117915B2 (en) | 2007-11-21 | 2021-09-14 | Cipla USA, Inc. | Antibacterial aminoglycoside analogs |
| US8383596B2 (en) | 2007-11-21 | 2013-02-26 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US9688711B2 (en) | 2007-11-21 | 2017-06-27 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US9266919B2 (en) | 2007-11-21 | 2016-02-23 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| US8492354B2 (en) | 2009-05-15 | 2013-07-23 | 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 |
| US8524689B2 (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 |
| CN101575311B (en) * | 2009-06-19 | 2011-05-04 | 无锡好芳德药业有限公司 | Method for preparing epiphysin |
Also Published As
| Publication number | Publication date |
|---|---|
| IE40437L (en) | 1975-02-06 |
| LU70661A1 (en) | 1975-05-21 |
| NO139483B (en) | 1978-12-11 |
| DE2437160B2 (en) | 1979-01-04 |
| IL45385A (en) | 1978-10-31 |
| SE7409946L (en) | 1975-02-07 |
| CY1018A (en) | 1979-11-23 |
| IL45385A0 (en) | 1974-11-29 |
| DE2437160C3 (en) | 1979-08-30 |
| DE2462485C2 (en) | 1987-04-09 |
| NL171587B (en) | 1982-11-16 |
| FI62100B (en) | 1982-07-30 |
| NO139483C (en) | 1979-03-21 |
| FR2240015A1 (en) | 1975-03-07 |
| BG25804A3 (en) | 1978-12-12 |
| BE818431A (en) | 1975-02-03 |
| DE2462485A1 (en) | 1977-04-21 |
| FI230474A (en) | 1975-02-07 |
| SE424994B (en) | 1982-08-23 |
| AU7194274A (en) | 1976-02-05 |
| NL171587C (en) | 1983-04-18 |
| HK55179A (en) | 1979-08-17 |
| DD119037A5 (en) | 1976-04-05 |
| DK146298C (en) | 1984-02-06 |
| NO742787L (en) | 1975-03-03 |
| FR2240015B1 (en) | 1978-08-18 |
| AR215834A1 (en) | 1979-11-15 |
| MY8000090A (en) | 1980-12-31 |
| FI62100C (en) | 1982-11-10 |
| DK146298B (en) | 1983-08-29 |
| DK412474A (en) | 1975-04-01 |
| IE40437B1 (en) | 1979-06-06 |
| CH606076A5 (en) | 1978-10-13 |
| DE2437160A1 (en) | 1975-02-20 |
| NL7410363A (en) | 1975-02-10 |
| KE2981A (en) | 1979-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19940731 |