JPS5540612A - 3"-acetyl-4"-isovaleryltylosin - Google Patents
3"-acetyl-4"-isovaleryltylosinInfo
- Publication number
- JPS5540612A JPS5540612A JP11302378A JP11302378A JPS5540612A JP S5540612 A JPS5540612 A JP S5540612A JP 11302378 A JP11302378 A JP 11302378A JP 11302378 A JP11302378 A JP 11302378A JP S5540612 A JPS5540612 A JP S5540612A
- Authority
- JP
- Japan
- Prior art keywords
- acetyl
- formula
- tylosin
- methanol
- isovaleryltylosin
- 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.)
- Granted
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 229930194936 Tylosin Natural products 0.000 abstract 2
- 239000004182 Tylosin Substances 0.000 abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 2
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 abstract 2
- 229960004059 tylosin Drugs 0.000 abstract 2
- 235000019375 tylosin Nutrition 0.000 abstract 2
- FREZLSIGWNCSOQ-UHFFFAOYSA-N 3-methylbutanoyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(=O)CC(C)C FREZLSIGWNCSOQ-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 235000019658 bitter taste Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- -1 isovaleryl Chemical group 0.000 abstract 1
- 239000003120 macrolide antibiotic agent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000007669 thermal treatment Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
NEW MATERIAL:3"-Acetyl-4"-isovaleryltylosin of formula I (Ac=acetyl; Iva= isovaleryl) or its pharmaceutically permissible salts.
USE: Antibiotics. Pharmaceuticals for veterinary use, additives of feed. Same antibacterial activity as the antibiotic, tylosin, and strong antibacterial property against A, B and C types of macrolide-resistant bacteria. Free from bitter taste, and preferable as syrup for infants.
PROCESS: Tylosin is made to react with acetic anhydride in the presence of an inorganic base to give a compound of formula II, which is then heated to be acylated with isovaleric anhydride in an inert organic solvent in the presence of a tertiary organic amine. The product obtained is treated with NH3 in methanol or thanol, and then subjected to thermal treatment in methanol which may contain water to remove the acetyl of 2' position, giving the objective compound of formula I.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11302378A JPS5540612A (en) | 1978-09-14 | 1978-09-14 | 3"-acetyl-4"-isovaleryltylosin |
| SE7907547A SE445739B (en) | 1978-09-14 | 1979-09-11 | 3 ", 4" DIACYLTYLOSINE DERIVATIVE |
| IT25677/79A IT1123137B (en) | 1978-09-14 | 1979-09-12 | "3", 4 "-DIACYLTYLOSINE AND PROCEDURE FOR ITS PRODUCTION |
| FR7922759A FR2436150A1 (en) | 1978-09-14 | 1979-09-12 | 3 '', 4 '' DERIVATIVES - DIACYLTYLOSINE USEFUL AS MEDICINES |
| DK382979A DK153492C (en) | 1978-09-14 | 1979-09-13 | PROCEDURE FOR PREPARING 3AE, 4AE-DIACYLTYLOSIN DERIVATIVES |
| GB7931717A GB2031418B (en) | 1978-09-14 | 1979-09-13 | 3'',4''-diacyl derivatives of tylosin |
| HU79TO1116A HU181976B (en) | 1978-09-14 | 1979-09-13 | Process for preparing 3",4"-diacyl-tylosin derivatives |
| CH830879A CH642381A5 (en) | 1978-09-14 | 1979-09-13 | DIALKANOYLTYLOSIN DERIVATIVES. |
| CA335,557A CA1133899A (en) | 1978-09-14 | 1979-09-13 | 3", 4"-diacyltylosin derivatives |
| DE19792937267 DE2937267A1 (en) | 1978-09-14 | 1979-09-14 | 3 '', 4 '' DIACYLTYLOSIN DERIVATIVES |
| AT0607479A AT366699B (en) | 1978-09-14 | 1979-09-14 | METHOD FOR PRODUCING 3 '', 4 '' DIACYLTYLOSIN DERIVATIVES |
| US06/075,661 US4268665A (en) | 1978-09-14 | 1979-09-14 | Derivatives of antibiotic tylosin |
| NL7906894A NL7906894A (en) | 1978-09-14 | 1979-09-14 | 3 ", 4" DIACYLTYLOSINE DERIVATIVES. |
| AT0518080A AT367432B (en) | 1978-09-14 | 1980-10-20 | METHOD FOR PRODUCING NEW 3 ", 4" DIACYLTYLOSIN DERIVATIVES |
| DK446985A DK156071C (en) | 1978-09-14 | 1985-10-02 | PROCEDURE FOR PREPARING 3,3 '', 4 '' - TRIACYLTYLOSIN DERIVATIVES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11302378A JPS5540612A (en) | 1978-09-14 | 1978-09-14 | 3"-acetyl-4"-isovaleryltylosin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5540612A true JPS5540612A (en) | 1980-03-22 |
| JPS6155517B2 JPS6155517B2 (en) | 1986-11-28 |
Family
ID=14601497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11302378A Granted JPS5540612A (en) | 1978-09-14 | 1978-09-14 | 3"-acetyl-4"-isovaleryltylosin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5540612A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0375315U (en) * | 1989-11-28 | 1991-07-29 |
-
1978
- 1978-09-14 JP JP11302378A patent/JPS5540612A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6155517B2 (en) | 1986-11-28 |
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