IE45030L - Aminoglycoside antibiotics and their intermediates - Google Patents
Aminoglycoside antibiotics and their intermediatesInfo
- Publication number
- IE45030L IE45030L IE770761A IE76177A IE45030L IE 45030 L IE45030 L IE 45030L IE 770761 A IE770761 A IE 770761A IE 76177 A IE76177 A IE 76177A IE 45030 L IE45030 L IE 45030L
- Authority
- IE
- Ireland
- Prior art keywords
- group
- groups
- formula
- amino
- hydroxyl
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title abstract 2
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 229960000318 kanamycin Drugs 0.000 abstract 1
- 229930182823 kanamycin A Natural products 0.000 abstract 1
- 229930182824 kanamycin B Natural products 0.000 abstract 1
- SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SKKLOUVUUNMCJE-FQSMHNGLSA-N 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 238000013508 migration Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The kanamycin derivatives of formula I, in which R is an amino or hydroxyl group and R<1> is an alkyl group optionally substituted by hydroxyl and/or amino groups, are obtained by alkylation of the compounds of formula II, in which R<2> is H or a benzyl group, R<3> is an acyl-protecting group and R<4> is a hydroxyl group or an NHR<3> group, followed by the removal of the R<3> groups and the benzyl group R<2>, where appropriate. The compounds of formula II are new intermediates which are obtained by acylation of a kanamycin A, B or a 3-N-benzylkanamycin A, protected on all its amino functional groups, followed by the removal of the protecting groups and the intramolecular migration of the acyl group from oxygen to nitrogen. <IMAGE>
[GB1530201A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15421/76A GB1530201A (en) | 1976-04-14 | 1976-04-14 | Process for the preparation of aminoglycoside antibiotics and intermediates therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE45030L true IE45030L (en) | 1977-10-14 |
| IE45030B1 IE45030B1 (en) | 1982-06-02 |
Family
ID=10058845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE761/77A IE45030B1 (en) | 1976-04-14 | 1977-04-13 | Process for the preparation of aminoglycoside antibiotics and novel intermediates therefor |
Country Status (28)
| Country | Link |
|---|---|
| JP (2) | JPS52139044A (en) |
| AR (1) | AR219074A1 (en) |
| AT (1) | AT356267B (en) |
| AU (1) | AU497416B2 (en) |
| BE (1) | BE853564A (en) |
| BG (2) | BG27759A3 (en) |
| CA (1) | CA1083568A (en) |
| CH (1) | CH622528A5 (en) |
| CS (1) | CS202570B2 (en) |
| DD (2) | DD135496A5 (en) |
| DE (1) | DE2716533C3 (en) |
| DK (1) | DK164277A (en) |
| EG (1) | EG12909A (en) |
| ES (1) | ES457793A1 (en) |
| FI (1) | FI771144A7 (en) |
| FR (1) | FR2348223A1 (en) |
| GB (1) | GB1530201A (en) |
| GR (1) | GR68936B (en) |
| IE (1) | IE45030B1 (en) |
| IL (1) | IL51775A (en) |
| LU (1) | LU77108A1 (en) |
| NL (1) | NL7703567A (en) |
| NZ (1) | NZ183733A (en) |
| PH (1) | PH14029A (en) |
| PL (2) | PL197372A1 (en) |
| PT (1) | PT66422B (en) |
| RO (2) | RO74431A (en) |
| ZA (1) | ZA771944B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2924659A1 (en) * | 1979-06-19 | 1981-01-22 | Bayer Ag | PSEUDOTRISACCHARIDE, THEIR PRODUCTION AND USE AS A MEDICINAL PRODUCT |
| JPS61191642U (en) * | 1985-05-20 | 1986-11-28 | ||
| IT1225484B (en) * | 1987-11-27 | 1990-11-14 | Pierrel Spa | SYNTHESIS PROCEDURE OF AMIKACINA |
| CN101481397B (en) * | 2009-01-23 | 2012-10-31 | 北京大学 | Novel kanamycin A derivative, and preparation and use thereof |
| ES2687027T3 (en) | 2010-11-04 | 2018-10-23 | Albireo Ab | Ibat inhibitors for the treatment of liver diseases |
| CN106659726A (en) | 2014-06-25 | 2017-05-10 | Ea制药株式会社 | Solid preparation and method for preventing or reducing coloration thereof |
| CA2952405A1 (en) | 2014-06-25 | 2015-12-30 | Ea Pharma Co., Ltd. | Solid formulation and method for stabilizing the same |
| EP3012252A1 (en) | 2014-10-24 | 2016-04-27 | Ferring BV | Crystal modifications of elobixibat |
| WO2017138878A1 (en) | 2016-02-09 | 2017-08-17 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| ES2874669T3 (en) | 2016-02-09 | 2021-11-05 | Albireo Ab | Oral formulation of cholestyramine and its use |
| CN108601739B (en) | 2016-02-09 | 2022-01-04 | 阿尔比里奥公司 | Cholestyramine pill and preparation method thereof |
| US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
-
1976
- 1976-04-14 GB GB15421/76A patent/GB1530201A/en not_active Expired
-
1977
- 1977-03-29 AU AU23721/77A patent/AU497416B2/en not_active Expired
- 1977-03-29 IL IL51775A patent/IL51775A/en unknown
- 1977-03-30 ZA ZA00771944A patent/ZA771944B/en unknown
- 1977-03-30 NZ NZ183733A patent/NZ183733A/en unknown
- 1977-04-01 NL NL7703567A patent/NL7703567A/en not_active Application Discontinuation
- 1977-04-12 GR GR53193A patent/GR68936B/el unknown
- 1977-04-12 RO RO7790001A patent/RO74431A/en unknown
- 1977-04-12 FI FI771144A patent/FI771144A7/fi not_active Application Discontinuation
- 1977-04-12 PH PH19649A patent/PH14029A/en unknown
- 1977-04-12 RO RO77101733A patent/RO79969A/en unknown
- 1977-04-12 PT PT66422A patent/PT66422B/en unknown
- 1977-04-12 LU LU77108A patent/LU77108A1/xx unknown
- 1977-04-13 CH CH457377A patent/CH622528A5/en not_active IP Right Cessation
- 1977-04-13 PL PL19737277A patent/PL197372A1/en unknown
- 1977-04-13 FR FR7711108A patent/FR2348223A1/en not_active Withdrawn
- 1977-04-13 PL PL1977215139A patent/PL112867B1/en unknown
- 1977-04-13 DK DK164277A patent/DK164277A/en not_active IP Right Cessation
- 1977-04-13 EG EG217/77A patent/EG12909A/en active
- 1977-04-13 BE BE176696A patent/BE853564A/en unknown
- 1977-04-13 AR AR267190A patent/AR219074A1/en active
- 1977-04-13 CA CA276,055A patent/CA1083568A/en not_active Expired
- 1977-04-13 JP JP4246577A patent/JPS52139044A/en active Granted
- 1977-04-13 IE IE761/77A patent/IE45030B1/en unknown
- 1977-04-14 DE DE2716533A patent/DE2716533C3/en not_active Expired
- 1977-04-14 CS CS772453A patent/CS202570B2/en unknown
- 1977-04-14 DD DD77204695A patent/DD135496A5/en unknown
- 1977-04-14 AT AT261477A patent/AT356267B/en not_active IP Right Cessation
- 1977-04-14 DD DD7700198399A patent/DD130661A5/en unknown
- 1977-04-14 ES ES457793A patent/ES457793A1/en not_active Expired
- 1977-04-14 BG BG036000A patent/BG27759A3/en unknown
- 1977-04-14 BG BG037121A patent/BG28072A4/en unknown
- 1977-06-23 JP JP7490277A patent/JPS535141A/en active Granted
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