SE7601810L - AMINOCYCLITOLANTIBIOTICS AND PROCEDURES FOR THE PREPARATION - Google Patents
AMINOCYCLITOLANTIBIOTICS AND PROCEDURES FOR THE PREPARATIONInfo
- Publication number
- SE7601810L SE7601810L SE7601810A SE7601810A SE7601810L SE 7601810 L SE7601810 L SE 7601810L SE 7601810 A SE7601810 A SE 7601810A SE 7601810 A SE7601810 A SE 7601810A SE 7601810 L SE7601810 L SE 7601810L
- Authority
- SE
- Sweden
- Prior art keywords
- hydrogen
- resulting
- prepared
- dideoxy
- deoxy
- Prior art date
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
1529376 Aminocyclitol antibiotics STERLING DRUG Inc 9 Feb 1976 [18 Feb 1975 22 Sept 1975] 04973/76 Heading C2C Novel aminocyclitol antibiotics of the general Formula I wherein R 1 , R 3 and R 8 are hydrogen, or one of R 1 , R 3 and R 8 is H 2 NCH 2 (CH 2 ) n CHOHCO-, wherein n is 0 or 1, and the others are hydrogen; R 2 is H or OH; R 5 is hydrogen, hydroxy or halogen, except that when R 2 is hydrogen, R 5 is not hydroxy cis to the amino groups at the 1- and 3- positions; and R 6 and R 7 are each hydrogen or methyl, and acid addition salts thereof are prepared (a) when R 1 ,R 4 and R 8 are each hydrogen, by culturing a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and a corresponding aminocyclitol of the general formula wherein R 1 , R 2 , R 3 and R 5 are as defined above, except that R 1 and R 3 may also form a single bond between the nitrogen atoms to which they are attached, in the presence of Micromonospora purpurea ATCC 31,119, and isolating the desired product from the medium; (b) when R 1 , R 3 and R 8 are each hydrogen and R 5 is as defined above with the exception of halogen, by culturing a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and a cyclitol of the general formula wherein R is hydrogen or acetyl, R<SP>1</SP> 3 is oxo or hydroxy and R<SP>1</SP> 2 and R<SP>1</SP> 5 are each hydrogen or OR, in the presence of Micromonospora purpurea ATCC 31,164; (c) when R 1 , R 3 and R 8 are each hydrogen and R 5 is as defined above with the exception of halogen, by culturing a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and an aminoclitol of the general formula wherein R<SP>1</SP> 2 and R<SP>1</SP> 5 correspond to R 2 and R 5 and R<SP>1</SP> 1 is amino or hydroxy, in the presence of Micromonospora purpurea 31,164; and (d) when one of R 1 , R 3 and R 8 is by reacting the product of (a), (b) or (c) with an N-hydroxysuccinimide ester of the general formula followed by hydrogenolysis of the resulting N- benzylorycarbonyl derivative with hydrogen and a catalyst; followed optionally by salification of the product. dl-Deoxyinosose is prepared by microbiological oxidation of dl-viboquercitol with Acetobacter suboxydans. dl - 2,3,4,6 - Tetrahydroxy - cyclohexanone- (2,4,6-cis) is prepared by reducing dl-epiinosose with hydrogen and PtO 2 and oxidizing the resulting di-epi-quercitol with Acetobacter suboxydans, 2,4,5-Tri-hydroxycyclohexanone(2,4-cis) is prepared by treating 4-cyclohexene-1α,2#-diol with 3-chloroperbenzoic acid and heating the resulting 4,5-epoxycyclohexane-1α,2#-diol with BF 3 etherate. 2,5-Dideoxy-5-iodostreptamine is prepared by treating 2-deoxy-1,6 : 3,4-dicarbonylstreptamine with methanesulphonyl chloride, treating the resulting 5-O-methanesulphonyl derivative with Na1, refluxing the resulting 5-deoxy- 5-iodo derivative with HCl, treating the resulting 2,5-dideoxy-5-iodostreptamine dihydrochloride with acetic anhydride and sodium acetate and hydrolysing the resulting N,N<SP>1</SP>-diacetyl-2,5- dideoxy-5-iodo-streptamine with aqueous HCl. 2,5-Dideoxy-5-fluorostreptamine is prepared by heating 2-deoxy-5-O-methanesulphonyl-1,6 : 3,4-dicarbonylstreptamine with HCl, reacting the resulting 2-deoxy-5-O-methanesulphonylstreptamine dihydrochloride with aqueous NaOH and then benzyl chloroformate, treating the resulting N,N<SP>1</SP>- di - carbobenzoxy - 2 -deoxy - 5-O- methanesulphonylstreptamine with KF and hydrolysing the resulting N,N<SP>1</SP>-dicarbobenzoxy- 2,5-dideoxy-5-fluorostreptamine with aqueous mineral acid. Pharmaceutical compositions having antibacterial activity comprise, as active ingredient, an aminocyclitol antibiotic (I) or an acid addition salt thereof, together with a pharmaceutical carrier.
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 |
---|---|
SE7601810L true SE7601810L (en) | 1976-08-19 |
Family
ID=27069389
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7601810A SE7601810L (en) | 1975-02-18 | 1976-02-17 | AMINOCYCLITOLANTIBIOTICS AND PROCEDURES FOR THE PREPARATION |
SE8007540A SE8007540L (en) | 1975-02-18 | 1980-10-27 | aminocyclitols |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE8007540A SE8007540L (en) | 1975-02-18 | 1980-10-27 | aminocyclitols |
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 |
---|---|---|---|---|
BE476970A (en) * | 1946-10-24 | |||
RU2458931C2 (en) | 2006-06-02 | 2012-08-20 | Мейдзи Сейка Фарма Ко., Лтд. | New aminoglycoside antibiotics |
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 AU AU11177/76A patent/AU503105B2/en not_active Ceased
- 1976-02-17 CA CA245,916A patent/CA1061731A/en not_active Expired
- 1976-02-17 GR GR50077A patent/GR60050B/en unknown
- 1976-02-17 CH CH193476A patent/CH617964A5/en not_active IP Right Cessation
- 1976-02-17 FI FI760387A patent/FI56026C/en not_active IP Right Cessation
- 1976-02-17 IL IL49053A patent/IL49053A/en unknown
- 1976-02-17 DK DK63176A patent/DK143111C/en not_active IP Right Cessation
- 1976-02-17 FR FR7604291A patent/FR2301265A1/en active Granted
- 1976-02-17 NZ NZ180036A patent/NZ180036A/en unknown
- 1976-02-17 IE IE311/76A patent/IE42807B1/en unknown
- 1976-02-17 SE SE7601810A patent/SE7601810L/en not_active Application Discontinuation
- 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 PT PT64816A patent/PT64816B/en unknown
- 1976-02-18 JP JP51016876A patent/JPS51108041A/ja active Pending
- 1976-02-18 AR AR262294A patent/AR221027A1/en active
- 1976-02-18 EG EG100/76A patent/EG12994A/en active
- 1976-02-18 ES ES445274A patent/ES445274A1/en not_active Expired
-
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
Also Published As
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