GB1111009A - Pleuromutilin derivatives useful in animal feed stuffs - Google Patents
Pleuromutilin derivatives useful in animal feed stuffsInfo
- Publication number
- GB1111009A GB1111009A GB16059/65A GB1605965A GB1111009A GB 1111009 A GB1111009 A GB 1111009A GB 16059/65 A GB16059/65 A GB 16059/65A GB 1605965 A GB1605965 A GB 1605965A GB 1111009 A GB1111009 A GB 1111009A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pleuromutilin
- acid
- ester
- hydrogenation product
- salt
- 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
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical class C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 title 1
- ZRZNJUXESFHSIO-BKUNHTPHSA-N 3de4a80mz1 Chemical compound C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-BKUNHTPHSA-N 0.000 abstract 9
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 abstract 8
- 150000002148 esters Chemical class 0.000 abstract 7
- 238000005984 hydrogenation reaction Methods 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000006052 feed supplement Substances 0.000 abstract 2
- YMBIICKZNSTXJA-UHFFFAOYSA-N 2-(carboxyamino)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NC(O)=O YMBIICKZNSTXJA-UHFFFAOYSA-N 0.000 abstract 1
- QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 abstract 1
- OURSFPZPOXNNKX-UHFFFAOYSA-N 3-sulfopropanoic acid Chemical compound OC(=O)CCS(O)(=O)=O OURSFPZPOXNNKX-UHFFFAOYSA-N 0.000 abstract 1
- 241001572230 Clitopilus passeckerianus Species 0.000 abstract 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 241000228143 Penicillium Species 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- -1 aliphatic monocarboxylic acid Chemical class 0.000 abstract 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Fodder In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Feed For Specific Animals (AREA)
Abstract
Esters of the antibiotic pleuromutilin or its hydrogenation product are obtained by reacting pleuromutilin or its hydrogenation product with an ester-forming derivative of an acid selected from isocyanic acid, an aliphatic monocarboxylic acid having from 3 to 19 carbon atoms, a haloformic acid or monohaloacetic acid, an aliphatic dicarboxylic acid having from 3 to 14 carbon atoms, or a sulphonic acid. The acid may contain an additional group capable of reacting with a base to form a salt; in which case, the first-formed ester is reacted with a base to form the salt. The ester of the hydrogenation product of pleuromutilin may be produced by forming the ester of pleuromutilin and hydrogenating the ester before or after treatment with the base to form the salt. Pleuromutilin has the formula <FORM:1111009/C2/1> On hydrogenation the vinyl group of pleuromutilin is hydrogenated to an ethyl group. Pleuromutilin, originally named antibiotic BC 757, was produced by the cultivation of Clitopilus passeckerianus (Pil.) Sing. NRRL 3100 in accordance with Specification 1,111,010. Typical esters are the succinate, monopalmitate, a - carboxyethylcarbamate, 1,3 - dicarboxypropylcarbamate, beta - sulphopropionate and m-sulphobenzoate. An animal feed or feed supplement comprises one or more esters of pleuromutilin or its hydrogenation product. Conventional feed supplements containing penicillium mycelia may be used.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT340364A AT250770B (en) | 1964-04-17 | 1964-04-17 | Feed |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111009A true GB1111009A (en) | 1968-04-24 |
Family
ID=3549996
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16059/65A Expired GB1111009A (en) | 1964-04-17 | 1965-04-14 | Pleuromutilin derivatives useful in animal feed stuffs |
| GB56203/67A Expired GB1111010A (en) | 1964-04-17 | 1965-04-14 | Process for the production of the antibiotic pleuromutilin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB56203/67A Expired GB1111010A (en) | 1964-04-17 | 1965-04-14 | Process for the production of the antibiotic pleuromutilin |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS4916631B1 (en) |
| AT (1) | AT250770B (en) |
| DE (1) | DE1249657B (en) |
| DK (2) | DK135973B (en) |
| ES (1) | ES311866A1 (en) |
| GB (2) | GB1111009A (en) |
| IL (2) | IL23314A (en) |
| NL (3) | NL6504695A (en) |
| SE (3) | SE362417B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002589A1 (en) * | 1977-12-08 | 1979-06-27 | Eli Lilly And Company | A-40104 antibiotics, their preparation, and formulations containing them |
| US11168049B1 (en) * | 2020-12-19 | 2021-11-09 | Xi'an Taikomed Pharmaceutical Technology Co., Ltd. | Pleuromulin tretinoin ester with antibacterial activity and a method of preparing the same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3949079A (en) * | 1964-04-17 | 1976-04-06 | Biochemie Ges.M.B.H. | Antibiotic derivatives |
| US4041175A (en) | 1974-05-13 | 1977-08-09 | E. R. Squibb & Sons, Inc. | Use of pleuromutilin for the treatment of swine dysentery |
| JPS55113645U (en) * | 1979-01-31 | 1980-08-11 | ||
| BG64840B1 (en) * | 2001-04-09 | 2006-06-30 | "Балканфарма-Разград" АД | Method for pleuromutiline preparation |
-
0
- DE DENDAT1249657D patent/DE1249657B/de active Pending
-
1964
- 1964-04-17 AT AT340364A patent/AT250770B/en active
-
1965
- 1965-04-07 IL IL23314A patent/IL23314A/en unknown
- 1965-04-07 IL IL31374A patent/IL31374A/en unknown
- 1965-04-09 SE SE10225/69A patent/SE362417B/xx unknown
- 1965-04-09 SE SE4674/65A patent/SE322405B/xx unknown
- 1965-04-09 SE SE10224/69A patent/SE354482B/xx unknown
- 1965-04-12 DK DK184965AA patent/DK135973B/en unknown
- 1965-04-13 NL NL6504695A patent/NL6504695A/xx unknown
- 1965-04-14 GB GB16059/65A patent/GB1111009A/en not_active Expired
- 1965-04-14 ES ES0311866A patent/ES311866A1/en not_active Expired
- 1965-04-14 GB GB56203/67A patent/GB1111010A/en not_active Expired
-
1967
- 1967-10-31 JP JP42070208A patent/JPS4916631B1/ja active Pending
-
1969
- 1969-07-18 NL NL6911083A patent/NL6911083A/xx unknown
- 1969-07-18 NL NL6911082A patent/NL6911082A/xx unknown
-
1971
- 1971-08-13 DK DK396671AA patent/DK127192B/en unknown
- 1971-12-03 JP JP46098209A patent/JPS5026540B1/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002589A1 (en) * | 1977-12-08 | 1979-06-27 | Eli Lilly And Company | A-40104 antibiotics, their preparation, and formulations containing them |
| FR2411204A1 (en) * | 1977-12-08 | 1979-07-06 | Lilly Co Eli | NEW ANTIBIOTICS AND THEIR PRODUCTION PROCESS |
| US11168049B1 (en) * | 2020-12-19 | 2021-11-09 | Xi'an Taikomed Pharmaceutical Technology Co., Ltd. | Pleuromulin tretinoin ester with antibacterial activity and a method of preparing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DK135973B (en) | 1977-07-25 |
| IL23314A (en) | 1969-04-30 |
| JPS4916631B1 (en) | 1974-04-23 |
| SE322405B (en) | 1970-04-06 |
| DK127192B (en) | 1973-10-01 |
| AT250770B (en) | 1966-11-25 |
| GB1111010A (en) | 1968-04-24 |
| NL6504695A (en) | 1965-10-18 |
| ES311866A1 (en) | 1965-07-16 |
| NL6911082A (en) | 1969-10-27 |
| SE354482B (en) | 1973-03-12 |
| DK135973C (en) | 1977-12-27 |
| JPS5026540B1 (en) | 1975-09-01 |
| DE1249657B (en) | |
| IL31374A (en) | 1969-05-28 |
| NL6911083A (en) | 1969-10-27 |
| SE362417B (en) | 1973-12-10 |
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