DE2754718A1 - Oleandomycin-derivate, verfahren zu ihrer herstellung und diese derivate enthaltende mittel - Google Patents
Oleandomycin-derivate, verfahren zu ihrer herstellung und diese derivate enthaltende mittelInfo
- Publication number
- DE2754718A1 DE2754718A1 DE19772754718 DE2754718A DE2754718A1 DE 2754718 A1 DE2754718 A1 DE 2754718A1 DE 19772754718 DE19772754718 DE 19772754718 DE 2754718 A DE2754718 A DE 2754718A DE 2754718 A1 DE2754718 A1 DE 2754718A1
- Authority
- DE
- Germany
- Prior art keywords
- acetyl
- compound
- yloxy
- oleandomycin
- formula
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 25
- RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical class O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 title description 55
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
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- 239000003085 diluting agent Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
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- 239000004104 Oleandomycin Substances 0.000 description 51
- 229960002351 oleandomycin Drugs 0.000 description 51
- RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 description 48
- 235000019367 oleandomycin Nutrition 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000001589 carboacyl group Chemical group 0.000 description 15
- -1 vinyl compound Chemical class 0.000 description 15
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
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- 238000012360 testing method Methods 0.000 description 6
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- 238000010561 standard procedure Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 230000037396 body weight Effects 0.000 description 3
- QHBMZRLZSGTUGW-UHFFFAOYSA-N butyl-(carboxysulfamoyl)-diethylazanium;hydroxide Chemical compound [OH-].CCCC[N+](CC)(CC)S(=O)(=O)NC(O)=O QHBMZRLZSGTUGW-UHFFFAOYSA-N 0.000 description 3
- USTQSEJKTIDFAG-UHFFFAOYSA-N carboxysulfamoyl-diethyl-propylazanium;hydroxide Chemical compound [OH-].CCC[N+](CC)(CC)S(=O)(=O)NC(O)=O USTQSEJKTIDFAG-UHFFFAOYSA-N 0.000 description 3
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
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- 239000003960 organic solvent Substances 0.000 description 2
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- 239000012264 purified product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000272522 Anas Species 0.000 description 1
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- 101100189378 Caenorhabditis elegans pat-3 gene Proteins 0.000 description 1
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- 108010003272 Hyaluronate lyase Proteins 0.000 description 1
- 102000001974 Hyaluronidases Human genes 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- 229910002651 NO3 Inorganic materials 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- SVXNTKZTPPFFRB-UHFFFAOYSA-N [OH-].CC(C)CC[N+](CC)(CC)S(=O)(=O)NC(O)=O Chemical compound [OH-].CC(C)CC[N+](CC)(CC)S(=O)(=O)NC(O)=O SVXNTKZTPPFFRB-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 239000008365 aqueous carrier Substances 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- XBSNNCXHZVUZBT-UHFFFAOYSA-N carboxysulfamoyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)S(=O)(=O)NC(O)=O XBSNNCXHZVUZBT-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/749,481 US4064143A (en) | 1976-12-10 | 1976-12-10 | Oleandomycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2754718A1 true DE2754718A1 (de) | 1978-06-15 |
Family
ID=25013915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772754718 Pending DE2754718A1 (de) | 1976-12-10 | 1977-12-08 | Oleandomycin-derivate, verfahren zu ihrer herstellung und diese derivate enthaltende mittel |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4064143A (enExample) |
| JP (1) | JPS5373577A (enExample) |
| AR (1) | AR219512A1 (enExample) |
| BE (1) | BE861691A (enExample) |
| DE (1) | DE2754718A1 (enExample) |
| DK (1) | DK148034C (enExample) |
| ES (1) | ES464924A1 (enExample) |
| FR (1) | FR2373559A1 (enExample) |
| GB (1) | GB1541331A (enExample) |
| IE (1) | IE46181B1 (enExample) |
| LU (1) | LU78667A1 (enExample) |
| NL (1) | NL172161C (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009539970A (ja) | 2006-06-12 | 2009-11-19 | ラモット アット テル−アビブ ユニバーシティー リミテッド | 癌の治療方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3144466A (en) * | 1963-03-08 | 1964-08-11 | Pfizer & Co C | Diacyl esters of de-oleandrosehydroxyoleandomycin and process therefor |
-
1976
- 1976-12-10 US US05/749,481 patent/US4064143A/en not_active Expired - Lifetime
-
1977
- 1977-12-08 GB GB51235/77A patent/GB1541331A/en not_active Expired
- 1977-12-08 DE DE19772754718 patent/DE2754718A1/de active Pending
- 1977-12-09 DK DK549777A patent/DK148034C/da not_active IP Right Cessation
- 1977-12-09 BE BE183321A patent/BE861691A/xx not_active IP Right Cessation
- 1977-12-09 IE IE2504/77A patent/IE46181B1/en unknown
- 1977-12-09 ES ES464924A patent/ES464924A1/es not_active Expired
- 1977-12-09 JP JP14803277A patent/JPS5373577A/ja active Granted
- 1977-12-09 FR FR7737182A patent/FR2373559A1/fr active Granted
- 1977-12-09 AR AR270304A patent/AR219512A1/es active
- 1977-12-09 NL NLAANVRAGE7713650,A patent/NL172161C/xx not_active IP Right Cessation
- 1977-12-09 LU LU78667A patent/LU78667A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES464924A1 (es) | 1978-09-01 |
| DK549777A (da) | 1978-06-11 |
| GB1541331A (en) | 1979-02-28 |
| NL7713650A (nl) | 1978-06-13 |
| FR2373559A1 (fr) | 1978-07-07 |
| JPS558519B2 (enExample) | 1980-03-04 |
| DK148034C (da) | 1985-07-08 |
| LU78667A1 (fr) | 1979-06-13 |
| JPS5373577A (en) | 1978-06-30 |
| IE46181B1 (en) | 1983-03-23 |
| NL172161B (nl) | 1983-02-16 |
| AR219512A1 (es) | 1980-08-29 |
| DK148034B (da) | 1985-02-11 |
| NL172161C (nl) | 1983-07-18 |
| FR2373559B1 (enExample) | 1980-08-22 |
| IE46181L (en) | 1978-06-10 |
| US4064143A (en) | 1977-12-20 |
| BE861691A (fr) | 1978-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| OHW | Rejection |