CA1075234A - Antibiotic substances derived from antibiotic 67-694 and processes for their preparation - Google Patents
Antibiotic substances derived from antibiotic 67-694 and processes for their preparationInfo
- Publication number
- CA1075234A CA1075234A CA246,429A CA246429A CA1075234A CA 1075234 A CA1075234 A CA 1075234A CA 246429 A CA246429 A CA 246429A CA 1075234 A CA1075234 A CA 1075234A
- Authority
- CA
- Canada
- Prior art keywords
- rosamicin
- chromous
- antibiotic
- mineral acid
- dehydrorosamicin
- 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
- IUPCWCLVECYZRV-JZMZINANSA-N rosaramicin Chemical compound O([C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H]([C@@H]2O[C@@]2(C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O IUPCWCLVECYZRV-JZMZINANSA-N 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000003115 biocidal effect Effects 0.000 title abstract description 3
- 239000000126 substance Substances 0.000 title 1
- ZUHRLTIPDRLJHR-UHFFFAOYSA-N Rosamicin Natural products CCC1OC(=O)CC(O)C(C)C(OC2OC(C)CC(C2O)N(C)C)C(CC=O)CC(C)C(=O)C=CC3OC3C1C ZUHRLTIPDRLJHR-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 6
- 239000011707 mineral Substances 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910021554 Chromium(II) chloride Inorganic materials 0.000 claims description 7
- XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 claims description 7
- 229940109126 chromous chloride Drugs 0.000 claims description 7
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims 1
- 241000218940 Micromonospora rosaria Species 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 229940032330 sulfuric acid Drugs 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 235000011449 Rosa Nutrition 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960000359 chromic chloride Drugs 0.000 description 1
- UZEDIBTVIIJELN-UHFFFAOYSA-N chromium(2+) Chemical compound [Cr+2] UZEDIBTVIIJELN-UHFFFAOYSA-N 0.000 description 1
- RYPRIXSYXLDSOA-UHFFFAOYSA-L chromium(2+);sulfate Chemical compound [Cr+2].[O-]S([O-])(=O)=O RYPRIXSYXLDSOA-UHFFFAOYSA-L 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- LJAOOBNHPFKCDR-UHFFFAOYSA-K chromium(3+) trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Cr+3] LJAOOBNHPFKCDR-UHFFFAOYSA-K 0.000 description 1
- 229910000334 chromium(II) sulfate Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- BMSDTRMGXCBBBH-UHFFFAOYSA-L diiodochromium Chemical compound [Cr+2].[I-].[I-] BMSDTRMGXCBBBH-UHFFFAOYSA-L 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55425075A | 1975-02-28 | 1975-02-28 | |
| US05/554,266 US3975372A (en) | 1975-02-28 | 1975-02-28 | Preparation of 12,13-desepoxy-12,13-dehydrorosamicin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1075234A true CA1075234A (en) | 1980-04-08 |
Family
ID=27070531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA246,429A Expired CA1075234A (en) | 1975-02-28 | 1976-02-24 | Antibiotic substances derived from antibiotic 67-694 and processes for their preparation |
Country Status (20)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4279896A (en) * | 1980-06-23 | 1981-07-21 | Schering Corporation | Novel 20-imino macrolide antibacterial agents |
| JPS58219197A (ja) * | 1982-06-15 | 1983-12-20 | Sanraku Inc | マクロライド系抗生物質の誘導体 |
| US4436729A (en) * | 1982-06-30 | 1984-03-13 | Schering Corporation | 23-Demycinosyltylosin compounds, pharmaceutical compositions and method of use |
| US4454314A (en) * | 1982-08-02 | 1984-06-12 | Pfizer Inc. | Antibacterial mycaminosyl tylonolide and related macrolide derivatives |
| SI8710674B (sl) * | 1987-04-14 | 1998-06-30 | Pliva | Postopek za pripravo 10,11,12,13-tetrahidro derivatov tilozina |
| PT87417B (pt) * | 1987-05-06 | 1992-08-31 | Adir | Processo para a preparacao de novos compostos macrolidos |
| FR2626576B1 (fr) * | 1987-05-06 | 1991-07-12 | Adir | Nouveaux derives de la carbomycine b, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5195268A (en) * | 1991-11-21 | 1993-03-23 | Ellis Gregory T | Weedless hook for lures |
| US5218778A (en) * | 1992-05-28 | 1993-06-15 | Szantor Alfons J | Fishing lure |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR205976A1 (es) * | 1972-11-15 | 1976-06-23 | Scherico Ltd | Procedimiento para la preparacion de derivados de 3-monoesteres de rosamicina que tienen actividad antibacteriana |
-
1976
- 1976-02-18 CH CH206676A patent/CH630391A5/de not_active IP Right Cessation
- 1976-02-24 DE DE19762607459 patent/DE2607459A1/de not_active Withdrawn
- 1976-02-24 NO NO760606A patent/NO141718C/no unknown
- 1976-02-24 LU LU74420A patent/LU74420A1/xx unknown
- 1976-02-24 ES ES445489A patent/ES445489A1/es not_active Expired
- 1976-02-24 GB GB7260/76A patent/GB1544819A/en not_active Expired
- 1976-02-24 FR FR7605091A patent/FR2302102A1/fr active Granted
- 1976-02-24 CA CA246,429A patent/CA1075234A/en not_active Expired
- 1976-02-24 AR AR262356A patent/AR215851A1/es active
- 1976-02-24 PT PT64836A patent/PT64836B/pt unknown
- 1976-02-24 AT AT133376A patent/AT344321B/de not_active IP Right Cessation
- 1976-02-24 NL NL7601863A patent/NL7601863A/xx not_active Application Discontinuation
- 1976-02-24 FI FI760473A patent/FI63421C/sv not_active IP Right Cessation
- 1976-02-25 JP JP51019830A patent/JPS51110585A/ja active Pending
- 1976-02-25 DK DK79876*#A patent/DK79876A/da not_active Application Discontinuation
- 1976-02-25 AU AU11419/76A patent/AU499566B2/en not_active Expired
- 1976-02-25 IL IL49104A patent/IL49104A/en unknown
- 1976-02-25 IE IE375/76A patent/IE42957B1/en unknown
- 1976-02-26 DD DD191537A patent/DD125959A5/xx unknown
- 1976-02-26 HU HU76SCHE556A patent/HU176333B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK79876A (da) | 1976-08-29 |
| FI63421B (fi) | 1983-02-28 |
| NO141718C (no) | 1980-04-30 |
| PT64836A (en) | 1976-03-01 |
| IL49104A (en) | 1979-12-30 |
| NL7601863A (nl) | 1976-08-31 |
| AT344321B (de) | 1978-07-10 |
| DE2607459A1 (de) | 1976-09-09 |
| IE42957L (en) | 1976-08-28 |
| PT64836B (en) | 1977-06-07 |
| IE42957B1 (en) | 1980-11-19 |
| GB1544819A (en) | 1979-04-25 |
| FR2302102A1 (fr) | 1976-09-24 |
| HU176333B (en) | 1981-01-28 |
| DD125959A5 (enrdf_load_stackoverflow) | 1977-06-08 |
| NO141718B (no) | 1980-01-21 |
| ATA133376A (de) | 1977-11-15 |
| CH630391A5 (en) | 1982-06-15 |
| ES445489A1 (es) | 1977-11-16 |
| FR2302102B1 (enrdf_load_stackoverflow) | 1978-12-01 |
| NO760606L (enrdf_load_stackoverflow) | 1976-08-31 |
| AU1141976A (en) | 1977-09-01 |
| AR215851A1 (es) | 1979-11-15 |
| LU74420A1 (enrdf_load_stackoverflow) | 1977-01-07 |
| FI63421C (fi) | 1983-06-10 |
| AU499566B2 (en) | 1979-04-26 |
| IL49104A0 (en) | 1976-04-30 |
| FI760473A7 (enrdf_load_stackoverflow) | 1976-08-29 |
| JPS51110585A (enrdf_load_stackoverflow) | 1976-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |