ES445274A1 - Aminocyclitol antibiotics and processes therefor - Google Patents
Aminocyclitol antibiotics and processes thereforInfo
- Publication number
- ES445274A1 ES445274A1 ES445274A ES445274A ES445274A1 ES 445274 A1 ES445274 A1 ES 445274A1 ES 445274 A ES445274 A ES 445274A ES 445274 A ES445274 A ES 445274A ES 445274 A1 ES445274 A1 ES 445274A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- hydrogen
- hydroxy
- compound
- aminocyclitol
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/487—Saturated compounds containing a keto group being part of a ring containing hydroxy groups
- C07C49/497—Saturated compounds containing a keto group being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for preparing a compound having formula I (herein) wherein it represents hydrogen or lower alkyl; R3 and R8 represent hydrogen or one of R1 R3 and R8 represents an omega-aminoalpha-hydroxy-lower alkanoyl group having the formula H2NCH2 (CH2) nCHOHCO- where n is zero or one, the other of R1, R3 and R8 is hydrogen R2 represents hydrogen or hydroxy; R5 represents hydrogen, hydroxy or halogen except that when R2 is hydrogen, R5 is not hydroxy in the cis position with respect to the amino groups in positions 1 and 3; and R6 and R7 each represent hydrogen or methyl, an acid addition salt thereof, characterized by cultivating a nutrient medium containing carbohydrates, a source or source of assimilable nitrogen, essential salts and a corresponding added aminocyclitol or a corresponding cyclitol thereby defined below in the presence of an appropriate mutant microorganism as defined below, and isolating the product from the culture medium where it is used: a) an aminocyclitol of Formula XI (herein) wherein R1 and R3 represent hydrogens or together represent a single bond linking the two amino nitrogen atoms together and R2 and R5 have the above meanings in the presence of an incapable mimic microorganism to sinter the aminocyclitol itself but being able to incorporate the aminocyclitol or the compound of Formula I under the above conditions where a compound of Formula I is produced where R1, R3 and R8 each represent hydrogen and R2, R5, R6 and R7 have the indicated meanings; b) a cyclitol having Formula IIIa or IIIb (herein) wherein in any case R is hydrogen or acetyl; R3'is oxo or hydroxy; and R2'and R5' each is hydrogen, hydroxide, or OR, in the presence of a strain of a microorganism that is capable of biosynthesizing the cyclitol unit but is capable of incorporating cyclitol into the antibiotic molecule as an aminocyclitol unit in where a compound of Formula I is produced wherein R1, R3 and R8 each represent hydrogen and R2, R5, R6 and R7 have the indicated meanings; except that R5 does not include halogen; or c) an aminocyclitol having Formula IIa or IIb (herein) wherein in either case R2'and R5' are each hydrogen or hydroxy in formula IIa and hydroxy or benzylideneimino in formula IIb, and R1'is amino, lower alkylamino or hydroxy in the presence of Micromonospora purpurea CCTA 31, 164 where a compound of Formula I is produced where R3 and R8 each represent hydrogen; R2, R5, R6 and R7 have the indicated meanings and R3 represents hydrogen or lower alkyl, except that R5 does not include halogen; and if it is desired to produce a compound wherein one of R1, R3 and R8 represents an omega-amino-alpha-hydroxy-lower alkanoyl group, react the compound of Formula I obtained according to (a), (b) or (c) with an N-hydroxy-succinimide ester having Formula IV (herein) where n is zero or one and subject the benzyloxycarbonyl group in the resulting product to hydrogenolysis with hydrogen through a catalyst, and if it is desired to convert the free base obtained into an acid addition salt thereof. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/550,273 US3972930A (en) | 1975-02-18 | 1975-02-18 | Aminocyclitol antibiotics |
| US05/615,593 US3982996A (en) | 1975-09-22 | 1975-09-22 | Process for preparing aminocyclitol antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES445274A1 true ES445274A1 (en) | 1977-06-16 |
Family
ID=27069389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES445274A Expired ES445274A1 (en) | 1975-02-18 | 1976-02-18 | Aminocyclitol antibiotics and processes therefor |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS51108041A (en) |
| AR (3) | AR221027A1 (en) |
| AU (1) | AU503105B2 (en) |
| CA (1) | CA1061731A (en) |
| CH (3) | CH617964A5 (en) |
| DE (1) | DE2606517A1 (en) |
| DK (1) | DK143111C (en) |
| EG (1) | EG12994A (en) |
| ES (1) | ES445274A1 (en) |
| FI (1) | FI56026C (en) |
| FR (1) | FR2301265A1 (en) |
| GB (1) | GB1529376A (en) |
| GR (1) | GR60050B (en) |
| IE (1) | IE42807B1 (en) |
| IL (1) | IL49053A (en) |
| IN (2) | IN147046B (en) |
| NL (1) | NL7601655A (en) |
| NO (3) | NO147308C (en) |
| NZ (1) | NZ180036A (en) |
| PT (1) | PT64816B (en) |
| SE (2) | SE7601810L (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR955564A (en) * | 1946-10-24 | 1950-01-17 | ||
| AU2007255856B2 (en) | 2006-06-02 | 2012-08-16 | Meiji Seika Pharma Co., Ltd. | Novel aminoglycoside antibiotic |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH606434A5 (en) * | 1973-08-06 | 1978-10-31 | Scherico Ltd |
-
1976
- 1976-02-09 GB GB4973/76A patent/GB1529376A/en not_active Expired
- 1976-02-13 NO NO760472A patent/NO147308C/en unknown
- 1976-02-17 GR GR50077A patent/GR60050B/en unknown
- 1976-02-17 CA CA245,916A patent/CA1061731A/en not_active Expired
- 1976-02-17 IE IE311/76A patent/IE42807B1/en unknown
- 1976-02-17 NZ NZ180036A patent/NZ180036A/en unknown
- 1976-02-17 FR FR7604291A patent/FR2301265A1/en active Granted
- 1976-02-17 AU AU11177/76A patent/AU503105B2/en not_active Ceased
- 1976-02-17 FI FI760387A patent/FI56026C/en not_active IP Right Cessation
- 1976-02-17 DK DK63176A patent/DK143111C/en not_active IP Right Cessation
- 1976-02-17 SE SE7601810A patent/SE7601810L/en not_active Application Discontinuation
- 1976-02-17 CH CH193476A patent/CH617964A5/en not_active IP Right Cessation
- 1976-02-17 IL IL49053A patent/IL49053A/en unknown
- 1976-02-18 EG EG100/76A patent/EG12994A/en active
- 1976-02-18 JP JP51016876A patent/JPS51108041A/ja active Pending
- 1976-02-18 ES ES445274A patent/ES445274A1/en not_active Expired
- 1976-02-18 PT PT64816A patent/PT64816B/en unknown
- 1976-02-18 NL NL7601655A patent/NL7601655A/en not_active Application Discontinuation
- 1976-02-18 DE DE19762606517 patent/DE2606517A1/en not_active Ceased
- 1976-02-18 AR AR262294A patent/AR221027A1/en active
-
1977
- 1977-02-10 AR AR266507A patent/AR227266A1/en active
- 1977-02-10 AR AR266506A patent/AR217417A1/en active
- 1977-09-20 IN IN1416/CAL/77A patent/IN147046B/en unknown
-
1978
- 1978-11-01 CH CH1126678A patent/CH618214A5/en not_active IP Right Cessation
- 1978-11-01 CH CH1126778A patent/CH618215A5/en not_active IP Right Cessation
-
1979
- 1979-07-20 IN IN525/DEL/79A patent/IN149240B/en unknown
-
1980
- 1980-10-24 NO NO803185A patent/NO146811C/en unknown
- 1980-10-27 SE SE8007540A patent/SE8007540L/en not_active Application Discontinuation
-
1982
- 1982-02-24 NO NO820574A patent/NO148298C/en unknown
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