DE69308414T2 - Monensinderivate - Google Patents
MonensinderivateInfo
- Publication number
- DE69308414T2 DE69308414T2 DE69308414T DE69308414T DE69308414T2 DE 69308414 T2 DE69308414 T2 DE 69308414T2 DE 69308414 T DE69308414 T DE 69308414T DE 69308414 T DE69308414 T DE 69308414T DE 69308414 T2 DE69308414 T2 DE 69308414T2
- Authority
- DE
- Germany
- Prior art keywords
- groups
- monensin
- carbon atoms
- compound
- production
- 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 - Fee Related
Links
- GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical class C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 title claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 44
- GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 claims description 36
- 229930191564 Monensin Natural products 0.000 claims description 34
- 229960005358 monensin Drugs 0.000 claims description 34
- 241001465754 Metazoa Species 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 210000004767 rumen Anatomy 0.000 claims description 12
- 241000282849 Ruminantia Species 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 235000013336 milk Nutrition 0.000 claims description 8
- 239000008267 milk Substances 0.000 claims description 8
- 210000004080 milk Anatomy 0.000 claims description 8
- -1 1,1,2,2-tetrafluoroethyl groups Chemical group 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 3
- 229920001774 Perfluoroether Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 238000012360 testing method Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 235000005911 diet Nutrition 0.000 description 11
- 230000037213 diet Effects 0.000 description 11
- 241000283690 Bos taurus Species 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012530 fluid Substances 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- 238000004949 mass spectrometry Methods 0.000 description 8
- 239000000872 buffer Substances 0.000 description 7
- 238000000855 fermentation Methods 0.000 description 7
- 230000004151 fermentation Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003977 dairy farming Methods 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical class NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000013365 dairy product Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 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 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- RGGOWBBBHWTTRE-UHFFFAOYSA-N (4-bromophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Br)C=C1 RGGOWBBBHWTTRE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 206010016717 Fistula Diseases 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 102000014171 Milk Proteins Human genes 0.000 description 1
- 108010011756 Milk Proteins Proteins 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DBNLGTYGKCMLLR-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1 DBNLGTYGKCMLLR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000004140 ketosis Effects 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000021243 milk fat Nutrition 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- XOIQMTLWECTKJL-HXPDMXKUSA-M sodium;(3r,4s)-4-[(2s,5r,7s,8r,9s)-2-[(2r,5s)-5-ethyl-5-[(2r,3s,5r)-5-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]oxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methylpentanoate Chemical compound [Na+].C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)C(C)C([O-])=O)O2 XOIQMTLWECTKJL-HXPDMXKUSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Fodder In General (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Feed For Specific Animals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (4)
1. Verbindung der Formel
worin
R -CH&sub2;OH oder
bedeutet;
jeder Rest R¹ unabhangig
Halogen,
Nitrogruppen,
Niedrigalkylgruppen mit 1 bis 3 Kohlenstoffatomen,
Perfluoralkylgruppen mit 1 bis 3 Kohlenstoffatomen,
1,1,2,2-Tetrafluorethylgruppen,
Niedrigalkoxygruppen mit 1 bis 3 Kohlenstoffätomen,
Pertluoralkoxygruppen mit 1 bis 3 Kohlenstoffatomen,
1,1,2,2-Tetrafluorethoxygruppen oder
Cyanogruppen
bedeutet,
und jeder Index m unabhangig eine ganze Zahl von 0 bis 5 bedeutet, mit der Einschränkung, daß dann, wenn einer
der Reste R¹ etwas anderes als Halogen ist, m an diesem Ring nur eine ganze Zahl von 1 bis 3 ist; oder ein
physiologisch annehmbares Salz davon.
2. Verbindung nach Anspruch 1, die ein Monensin-C-25-Phenylhydrazinderivat oder ein physiologisch
annehmbares Salz davon ist.
3. Verfahren zur Erhöhung der Produktion an Propionat in dem Pansen eines Wiederkäuers oder zur
Erhöhung der Produkuon von Milch bei einem milchgebenden Wiederkäuer, das die nicht-therapeutische orale
Verabreichung einer wirksamen Menge einer Verbindung nach Anspruch 1 oder Anspruch 2 an das Tier umfaßt.
4. Tierfutter geeignet zur Verabreichung an Wiederkäuer, um das Wachstum zu erhöhen und die
Futterverwertung zu verbessern oder um die Milchproduktion zu erhöhen, oder eine Vormischung für ein solches Tierfutter,
das eine wirksame Konzentration eines aktiven Inhaltsstoffs umfaßt, der eine Verbindung nach Anspruch 1 oder
Anspruch 2 ist.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/916,653 US5217993A (en) | 1992-07-20 | 1992-07-20 | Monensin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69308414D1 DE69308414D1 (de) | 1997-04-10 |
| DE69308414T2 true DE69308414T2 (de) | 1997-07-17 |
Family
ID=25437628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69308414T Expired - Fee Related DE69308414T2 (de) | 1992-07-20 | 1993-07-16 | Monensinderivate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5217993A (de) |
| EP (1) | EP0580371B1 (de) |
| JP (1) | JPH06184159A (de) |
| AU (1) | AU669901B2 (de) |
| CA (1) | CA2100610A1 (de) |
| DE (1) | DE69308414T2 (de) |
| ES (1) | ES2098666T3 (de) |
| ZA (1) | ZA935128B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328929A (en) * | 1993-07-02 | 1994-07-12 | Arizona Board Of Regents | Isolation and structure of spongistatin 2, spongistatin 3, spongistatin 4 and spongistatin 6 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU531276B2 (en) * | 1978-11-29 | 1983-08-18 | F. Hoffmann-La Roche & Co. | Antibacterial urethane derivatives |
| US4542027A (en) * | 1984-02-23 | 1985-09-17 | Syntex (U.S.A.) Inc. | Laidlomycin phenylcarbamate |
| SU1531861A3 (ru) * | 1984-10-09 | 1989-12-23 | Эли Лилли Энд Компани (Фирма) | Способ получени полиэфирного антибиотика А 80190 |
| RU1825377C (ru) * | 1988-05-02 | 1993-06-30 | Эли Лилли Энд Компани | Способ получени антибиотика А 82810 или его производных, и штамм АстINомаDURа FIвRоSа - продуцент антибиотика А 82810 |
-
1992
- 1992-07-20 US US07/916,653 patent/US5217993A/en not_active Expired - Fee Related
-
1993
- 1993-07-15 CA CA002100610A patent/CA2100610A1/en not_active Abandoned
- 1993-07-15 ZA ZA935128A patent/ZA935128B/xx unknown
- 1993-07-16 DE DE69308414T patent/DE69308414T2/de not_active Expired - Fee Related
- 1993-07-16 EP EP93305612A patent/EP0580371B1/de not_active Expired - Lifetime
- 1993-07-16 ES ES93305612T patent/ES2098666T3/es not_active Expired - Lifetime
- 1993-07-16 AU AU42033/93A patent/AU669901B2/en not_active Ceased
- 1993-07-19 JP JP5177852A patent/JPH06184159A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0580371B1 (de) | 1997-03-05 |
| ZA935128B (en) | 1995-01-16 |
| EP0580371A1 (de) | 1994-01-26 |
| AU4203393A (en) | 1994-01-27 |
| CA2100610A1 (en) | 1994-01-21 |
| US5217993A (en) | 1993-06-08 |
| ES2098666T3 (es) | 1997-05-01 |
| AU669901B2 (en) | 1996-06-27 |
| JPH06184159A (ja) | 1994-07-05 |
| DE69308414D1 (de) | 1997-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1620114C3 (de) | Schiffsche Basen von 2 Formyl chinoxalin 1,4 dioxiden | |
| DE69101595T2 (de) | Verfahren zum aufzüchten von fleisch produzierenden tieren zur erhöhung der entwicklung von magerem fleisch. | |
| DE2953334C1 (de) | 3-(2,2,2-Trimethylhydrazinium)propionat,Verfahren zu dessen Herstellung und Futtermittel,welche dieses enthalten | |
| DE3206911A1 (de) | Biochemischer wirkstoff, dessen herstellung und diesen wirkstoff enthaltendes mittel | |
| DE2125245A1 (de) | Metabolisches Arzneimittel bzw. Futtermittelz usatz | |
| DE69006046T2 (de) | Verwendung von Sialinsäure enthaltenden oder bindenden Stoffen zur Neutralisierung von bakteriellen Toxinen. | |
| EP0017309B1 (de) | Zyklisches Hexapeptid und Dipeptid und sie enthaltende Zusammensetzungen | |
| DE69308414T2 (de) | Monensinderivate | |
| EP0119446A2 (de) | Wachstumsfördernde Aminophenylethylamin-Derivate | |
| DE2835936A1 (de) | Verfahren zur foerderung des wachstums von haustieren | |
| EP0422011A1 (de) | Mittel auf der basis von uracil-derivaten zur wachstumsförderung und fettreduktion bei tieren | |
| EP0112517B1 (de) | Polyätherverbindungen | |
| DE2834343A1 (de) | Antibiotikum 35 665 rp, seine herstellung und die dieses enthaltenden zusammensetzungen | |
| EP0057900A1 (de) | Neuer Futterzusatz zur Verbesserung des Wachstums | |
| AT391699B (de) | Verfahren zur herstellung neuer 4-chloro substituierter furo-(3,4-c)-pyridinderivate | |
| DE2143570B2 (de) | Arzneimittel zur Bekämpfung von Leberegelinfektionen bei Säugern | |
| US4421751A (en) | Bipyridine substituted imidazoylidene, copper complex, and its use in food-producing animals | |
| EP0154923A2 (de) | Monosilylierte Aminophenylethylamin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Wachstumsförderung | |
| Mraz | Calcium and strontium uptake by rat liver and kidney mitochondria. | |
| DE69630136T2 (de) | Trockene zusammensetzungen von ionophoren antibiotika | |
| EP0225600A2 (de) | Verfahren zur Leistungsförderung bei Nutztieren, neue Aminophenylethylamin-Derivate und ihre Herstellung | |
| DE2009222C3 (de) | Neue Nitrofurfuryliden-methylchinolyl-harnstoff-Derivate | |
| EP0142093B1 (de) | Staubfreie Chinoxalin-1,4-di-N-oxid enthaltende Zubereitung | |
| DE1140059B (de) | Wachstumfoerderndes Futtermittel | |
| EP0091090B1 (de) | Bipyridin-substituierter Imidazoyliden-Kupfer-Komplex und dessen Anwendung bei für menschlichen Verzehr gehaltenen Tieren und Bipyridin,2,2'-(imidazolidinyliden)-di-Kupfer-Komplex und Anwendung bei Tieren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |