DE2607459A1 - Neue antibiotische verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Neue antibiotische verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2607459A1 DE2607459A1 DE19762607459 DE2607459A DE2607459A1 DE 2607459 A1 DE2607459 A1 DE 2607459A1 DE 19762607459 DE19762607459 DE 19762607459 DE 2607459 A DE2607459 A DE 2607459A DE 2607459 A1 DE2607459 A1 DE 2607459A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- positions
- compounds
- carbon atoms
- stands
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 221
- 238000000034 method Methods 0.000 title claims description 65
- 230000003115 biocidal effect Effects 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229940126601 medicinal product Drugs 0.000 title 1
- 239000001257 hydrogen Substances 0.000 claims description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims description 128
- 125000004432 carbon atom Chemical group C* 0.000 claims description 102
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 72
- -1 alkyl radical Chemical class 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 46
- 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 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 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 description 33
- 150000003254 radicals Chemical class 0.000 claims description 33
- 150000002431 hydrogen Chemical class 0.000 claims description 32
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
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- 239000007858 starting material Substances 0.000 claims description 24
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- 125000004185 ester group Chemical group 0.000 claims description 13
- 231100000252 nontoxic Toxicity 0.000 claims description 12
- 230000003000 nontoxic effect Effects 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 9
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
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- 229910052721 tungsten Inorganic materials 0.000 claims description 8
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
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- 229910052786 argon Inorganic materials 0.000 claims description 4
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- 210000003608 fece Anatomy 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- 239000003814 drug Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
- 229910001513 alkali metal bromide Inorganic materials 0.000 claims description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
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- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical class [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 claims description 2
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 78
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- 239000000047 product Substances 0.000 description 40
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- 239000000203 mixture Substances 0.000 description 33
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 26
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
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- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 238000005406 washing Methods 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 |
|---|---|
| DE2607459A1 true DE2607459A1 (de) | 1976-09-09 |
Family
ID=27070531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762607459 Withdrawn DE2607459A1 (de) | 1975-02-28 | 1976-02-24 | Neue antibiotische verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2355790A1 (de) * | 1972-11-15 | 1974-05-16 | Scherico Ltd | Neue monoester von rosamicin |
-
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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2355790A1 (de) * | 1972-11-15 | 1974-05-16 | Scherico Ltd | Neue monoester von rosamicin |
Non-Patent Citations (1)
| Title |
|---|
| J. Antibiotics 25, 1972, S. 641-46 * |
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 |
| 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 |
| CA1075234A (en) | 1980-04-08 |
| 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 |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8136 | Disposal/non-payment of the fee for publication/grant |