CA1173385A - Antibiotiques polyethers sous forme de complexes de zinc utilises comme facteurs de croissance des animaux - Google Patents

Antibiotiques polyethers sous forme de complexes de zinc utilises comme facteurs de croissance des animaux

Info

Publication number: CA1173385A
Authority: CA; Canada
Prior art keywords: zinc; antibiotic; polyether; polyether antibiotic; complex
Prior art date: 1979-07-11
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

Application number

CA000356052A

Other languages

English (en)

Inventor

Jerome L. Martin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

International Minerals and Chemical Corp

Original Assignee

International Minerals and Chemical Corp

Priority date (The priority date 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 date listed.)

1979-07-11

Filing date

1980-07-11

Publication date

1984-08-28

1980-04-11 Priority claimed from US06/139,565 external-priority patent/US4378433A/en

1980-04-11 Priority claimed from US06/139,597 external-priority patent/US4356264A/en

1980-07-11 Application filed by International Minerals and Chemical Corp filed Critical International Minerals and Chemical Corp

1984-08-28 Application granted granted Critical

1984-08-28 Publication of CA1173385A publication Critical patent/CA1173385A/fr

Status Expired legal-status Critical Current

Links

239000011701 zinc Substances 0.000 title claims abstract description 93
229910052725 zinc Inorganic materials 0.000 title claims abstract description 92
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 90
229920000570 polyether Polymers 0.000 title claims abstract description 65
239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 57
241001465754 Metazoa Species 0.000 title claims abstract description 24
239000003242 anti bacterial agent Substances 0.000 title abstract description 101
229940088710 antibiotic agent Drugs 0.000 title abstract description 97
230000003115 biocidal effect Effects 0.000 claims abstract description 119
BBMULGJBVDDDNI-OWKLGTHSSA-N lasalocid Chemical compound C([C@@H]1[C@@]2(CC)O[C@@H]([C@H](C2)C)[C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)CCC=2C(=C(O)C(C)=CC=2)C(O)=O)C[C@](O)(CC)[C@H](C)O1 BBMULGJBVDDDNI-OWKLGTHSSA-N 0.000 claims abstract description 68
229960000320 lasalocid Drugs 0.000 claims abstract description 65
150000003751 zinc Chemical class 0.000 claims abstract description 65
229930182504 Lasalocid Natural products 0.000 claims abstract description 64
238000000855 fermentation Methods 0.000 claims abstract description 64
230000004151 fermentation Effects 0.000 claims abstract description 64
GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound 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 claims abstract description 20
-1 pyrrole ethers Chemical class 0.000 claims abstract description 18
229930191564 Monensin Natural products 0.000 claims abstract description 16
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 abstract description 16
DANUORFCFTYTSZ-UHFFFAOYSA-N epinigericin Natural products O1C2(C(CC(C)(O2)C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)C)C(C)C(OC)CC1CC1CCC(C)C(C(C)C(O)=O)O1 DANUORFCFTYTSZ-UHFFFAOYSA-N 0.000 claims abstract description 16
229960005358 monensin Drugs 0.000 claims abstract description 16
DANUORFCFTYTSZ-BIBFWWMMSA-N nigericin Chemical compound C([C@@H]1C[C@H]([C@H]([C@]2([C@@H](C[C@](C)(O2)C2O[C@@](C)(CC2)C2[C@H](CC(O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C)O1)C)OC)[C@H]1CC[C@H](C)C([C@@H](C)C(O)=O)O1 DANUORFCFTYTSZ-BIBFWWMMSA-N 0.000 claims abstract description 16
KTQFYFLZDLTLAH-UHFFFAOYSA-N Lysocellin Natural products CCC(O)C1(CC)CC(C)C(O)(O1)C2(C)CC(C)C(O2)C(CC)C(=O)C(C)C(O)C(C)C3OC(O)(CC(=O)O)C(C)CC3C KTQFYFLZDLTLAH-UHFFFAOYSA-N 0.000 claims abstract description 13
KTQFYFLZDLTLAH-DESDHLEASA-N lysocellin Chemical compound O1[C@]([C@@H](O)CC)(CC)C[C@@H](C)[C@]1(O)[C@@]1(C)O[C@H]([C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CC(O)=O)O2)C)[C@@H](C)C1 KTQFYFLZDLTLAH-DESDHLEASA-N 0.000 claims abstract description 13
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 12
239000002028 Biomass Substances 0.000 claims abstract description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 10
QFHLVPYVNFSTBE-SMAIMEEGSA-N (2r)-2-hydroxy-2-[(2s,3s,4s,5s,6s)-2-hydroxy-6-[[(2r,3r,4r,5s,6r,7r,9s)-2-[(2r,5s)-5-[(2r,5r)-5-[(2s,3s,4s,5r,6s)-6-hydroxy-4-[(2r,5s,6r)-5-methoxy-6-methyloxan-2-yl]oxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]oxolan-2-yl]-3,7-dimethoxy-2,4,6-trimethyl-1,10- Chemical compound O([C@@H]1[C@@H](C)[C@@](C)(O)O[C@@H]([C@H]1C)[C@H]1CC[C@@H](O1)[C@@H]1CC[C@@H](O1)[C@@]1(C)O[C@]2([C@H](C)[C@H]1OC)[C@@H]([C@H](OC)C[C@@H](C[C@H]1[C@]([C@@H](OC)[C@H](C)[C@@](O)([C@@H](O)C(O)=O)O1)(C)OC)O2)C)[C@H]1CC[C@H](OC)[C@@H](C)O1 QFHLVPYVNFSTBE-SMAIMEEGSA-N 0.000 claims abstract description 7
PGHMRUGBZOYCAA-ADZNBVRBSA-N ionomycin Chemical compound O1[C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)/C=C/C[C@@H](C)C[C@@H](C)C(/O)=C/C(=O)[C@@H](C)C[C@@H](C)C[C@@H](CCC(O)=O)C)CC[C@@]1(C)[C@@H]1O[C@](C)([C@@H](C)O)CC1 PGHMRUGBZOYCAA-ADZNBVRBSA-N 0.000 claims abstract description 7
PGHMRUGBZOYCAA-UHFFFAOYSA-N ionomycin Natural products O1C(CC(O)C(C)C(O)C(C)C=CCC(C)CC(C)C(O)=CC(=O)C(C)CC(C)CC(CCC(O)=O)C)CCC1(C)C1OC(C)(C(C)O)CC1 PGHMRUGBZOYCAA-UHFFFAOYSA-N 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 76
239000000203 mixture Substances 0.000 claims description 56
239000002460 polyether antibiotic agent Substances 0.000 claims description 53
244000005700 microbiome Species 0.000 claims description 48
239000003960 organic solvent Substances 0.000 claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
241000187747 Streptomyces Species 0.000 claims description 18
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 15
KQXDHUJYNAXLNZ-XQSDOZFQSA-N Salinomycin Chemical compound O1[C@@H]([C@@H](CC)C(O)=O)CC[C@H](C)[C@@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 KQXDHUJYNAXLNZ-XQSDOZFQSA-N 0.000 claims description 14
239000004189 Salinomycin Substances 0.000 claims description 14
239000003674 animal food additive Substances 0.000 claims description 14
229960001548 salinomycin Drugs 0.000 claims description 14
235000019378 salinomycin Nutrition 0.000 claims description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
ZITSQIZMRMDQLE-SJSJOXFOSA-N (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid Chemical compound CO[C@@H]1C[C@@H](C[C@H]2CC[C@H](C)[C@@H](O2)[C@@H](C)C(O)=O)O[C@]2(O[C@@](C)(C[C@H]2C)[C@H]2CC[C@](C)(O2)[C@@H]2O[C@H](C[C@@H]2C)[C@H]2O[C@](C)(O)[C@H](C)C[C@@H]2C)[C@@H]1C ZITSQIZMRMDQLE-SJSJOXFOSA-N 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
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VHKXXVVRRDYCIK-CWCPJSEDSA-N Narasin Chemical compound C[C@H]1C[C@H](C)[C@H]([C@@H](CC)C(O)=O)O[C@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 VHKXXVVRRDYCIK-CWCPJSEDSA-N 0.000 claims description 10
VHKXXVVRRDYCIK-UHFFFAOYSA-N Narasin Natural products CC1CC(C)C(C(CC)C(O)=O)OC1C(C)C(O)C(C)C(=O)C(CC)C1C(C)CC(C)C2(C=CC(O)C3(OC(C)(CC3)C3OC(C)C(O)(CC)CC3)O2)O1 VHKXXVVRRDYCIK-UHFFFAOYSA-N 0.000 claims description 10
229960001851 narasin Drugs 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
ZNBNBTIDJSKEAM-NISBWGIBSA-N (2s,3r,4r)-4-[(2s,5r,7s,8r,9s)-7-hydroxy-2-[(2r,5s)-5-[(2r,3s,5r)-5-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic a Chemical compound C1[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC(=O)CC)[C@H](C)C(O)=O)O[C@]11O[C@](C)([C@@H]2O[C@@](C)(CC2)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-NISBWGIBSA-N 0.000 claims description 8
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 8
WWDHGOLBPBWCNJ-UHFFFAOYSA-N Alborixin Natural products C1CC(O)(C)C(CC)OC1C1(C)OC(O)(C2(C)OC(CC2)C(O)C2(O)C(CC(C)C(CC3(O)C(CCC(O3)C(C)C(O)CC3C(CC(C)C(C(C)C(O)=O)O3)C)C)O2)C)C(C)C1 WWDHGOLBPBWCNJ-UHFFFAOYSA-N 0.000 claims description 8
RWWSBGHRGAQGJE-UHFFFAOYSA-N Laidlomycin Natural products CC(C(CCC(=O)O)C(C)C(=O)O)C1OC2(CCC(C)(O2)C3CCC(C)(O3)C4OC(CC4C)C5OC(O)(CO)C(C)CC5C)CC(O)C1C RWWSBGHRGAQGJE-UHFFFAOYSA-N 0.000 claims description 8
WWDHGOLBPBWCNJ-GXXSWWTOSA-N alborixin Chemical compound C1C[C@](O)(C)[C@H](CC)O[C@H]1[C@@]1(C)O[C@@](O)([C@@]2(C)O[C@@H](CC2)[C@@H](O)[C@@]2(O)[C@@H](C[C@H](C)[C@@H](C[C@]3(O)[C@H](CC[C@@H](O3)[C@@H](C)[C@H](O)C[C@H]3[C@@H](C[C@H](C)[C@@H]([C@@H](C)C(O)=O)O3)C)C)O2)C)[C@H](C)C1 WWDHGOLBPBWCNJ-GXXSWWTOSA-N 0.000 claims description 8
229960004561 laidlomycin Drugs 0.000 claims description 8
BKZOUCVNTCLNFF-IGXZVFLKSA-N (2s)-2-[(2r,3r,4s,5r,6s)-2-hydroxy-6-[(1s)-1-[(2s,5r,7s,8r,9s)-2-[(2r,5s)-5-[(2r,3s,4r,5r)-5-[(2s,3s,4s,5r,6s)-6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl]-4-methoxy-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,8-dimethyl-1,10-dioxaspiro[4.5]dec Chemical compound O([C@@H]1[C@@H]2O[C@H]([C@@H](C)[C@H]2OC)[C@@]2(C)O[C@H](CC2)[C@@]2(C)O[C@]3(O[C@@H]([C@H](C)[C@@H](OC)C3)[C@@H](C)[C@@H]3[C@@H]([C@H](OC)[C@@H](C)[C@](O)([C@H](C)C(O)=O)O3)C)CC2)[C@](C)(O)[C@H](C)[C@@H](OC)[C@@H]1C BKZOUCVNTCLNFF-IGXZVFLKSA-N 0.000 claims description 7
HENKHDHCZSYXMA-VIGVLEPISA-N CCOC(=O)[C@H]1O[C@H](C[C@H]1O)[C@@]1(C)O[C@]2(O[C@@]3(O[C@H]([C@@H](C)C(=O)[C@@H](C)[C@@H](O)[C@H](C)C[C@H](C)c4ccc(C)c(O)c4C(O)=O)[C@@H](C)C[C@H]3C)C=C[C@H]2O)[C@H](C)[C@H]1OC Chemical compound CCOC(=O)[C@H]1O[C@H](C[C@H]1O)[C@@]1(C)O[C@]2(O[C@@]3(O[C@H]([C@@H](C)C(=O)[C@@H](C)[C@@H](O)[C@H](C)C[C@H](C)c4ccc(C)c(O)c4C(O)=O)[C@@H](C)C[C@H]3C)C=C[C@H]2O)[C@H](C)[C@H]1OC HENKHDHCZSYXMA-VIGVLEPISA-N 0.000 claims description 7
BKZOUCVNTCLNFF-UHFFFAOYSA-N Lonomycin Natural products COC1C(C)C(C2(C)OC(CC2)C2(C)OC3(OC(C(C)C(OC)C3)C(C)C3C(C(OC)C(C)C(O)(C(C)C(O)=O)O3)C)CC2)OC1C1OC(C)(O)C(C)C(OC)C1C BKZOUCVNTCLNFF-UHFFFAOYSA-N 0.000 claims description 7
KRJBAINQJPYZJX-UHFFFAOYSA-N Mutalomycin Natural products COC1C(C)C(CC2OC3(CCC(C)(O3)C4CCC(C)(O4)C5OC(CC5C)C6OC(C)(O)C(C)CC6C)CC(O)C2C)OC(O)(C(C)C(=O)O)C1C KRJBAINQJPYZJX-UHFFFAOYSA-N 0.000 claims description 7
HENKHDHCZSYXMA-UHFFFAOYSA-N Noboritomycin A Natural products C1C(O)C(C(=O)OCC)OC1C1(C)C(OC)C(C)C2(C(C=CC3(C(CC(C)C(C(C)C(=O)C(C)C(O)C(C)CC(C)C=4C(=C(O)C(C)=CC=4)C(O)=O)O3)C)O2)O)O1 HENKHDHCZSYXMA-UHFFFAOYSA-N 0.000 claims description 7
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AFGBEDQMTFPVJS-UHFFFAOYSA-N Noboritomycin B Natural products C1C(O)C(C(=O)OCC)OC1C1(C)C(OC)C(C)C2(C(C=CC3(C(CC(C)C(C(C)C(=O)C(C)C(O)C(C)CC(C)C=4C(=C(O)C(CC)=CC=4)C(O)=O)O3)C)O2)O)O1 AFGBEDQMTFPVJS-UHFFFAOYSA-N 0.000 claims description 6
235000015097 nutrients Nutrition 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
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DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
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FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical group CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
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NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 2
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JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000356052A 1979-07-11 1980-07-11 Antibiotiques polyethers sous forme de complexes de zinc utilises comme facteurs de croissance des animaux Expired CA1173385A (fr)

Applications Claiming Priority (14)

Application Number	Priority Date	Filing Date	Title
US5664379A	1979-07-11	1979-07-11
US56,643		1979-07-11
US13959880A	1980-04-11	1980-04-11
US13956480A	1980-04-11	1980-04-11
US13956780A	1980-04-11	1980-04-11
US13956280A	1980-04-11	1980-04-11
US139,598		1980-04-11
US139,564		1980-04-11
US06/139,565 US4378433A (en)	1980-04-11	1980-04-11	Method for producing zinc etheromycin from fermentation broths
US139,562		1980-04-11
US139,597		1980-04-11
US06/139,597 US4356264A (en)	1980-04-11	1980-04-11	Zinc-containing antibiotic agents
US139,567		1987-12-30
US139,565		1987-12-30

Publications (1)

Publication Number	Publication Date
CA1173385A true CA1173385A (fr)	1984-08-28

Family

ID=27568113

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000356052A Expired CA1173385A (fr)	1979-07-11	1980-07-11	Antibiotiques polyethers sous forme de complexes de zinc utilises comme facteurs de croissance des animaux

Country Status (1)

Country	Link
CA (1)	CA1173385A (fr)

1980
- 1980-07-11 CA CA000356052A patent/CA1173385A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-08-28	MKEX	Expiry

Publication	Publication Date	Title
JP3557212B2 (ja)	2004-08-25	多環式駆虫薬、その製造のための方法及び菌株、並びにその用途
US4278663A (en)	1981-07-14	Antibiotic X-14868A, B, C and D
US3928571A (en)	1975-12-23	Ruminant feed utilization improvement
US4478935A (en)	1984-10-23	Manganese-containing antibiotic agents
CA1041448A (fr)	1978-10-31	Mode de preparation du complexe antibiotique a-28086 par la culture de streptomyces aureofaciens
US4035481A (en)	1977-07-12	Antibiotic A-28086 and process for production thereof
EP0001709B1 (fr)	1982-06-02	Antibiotiques du groupe de la déoxynarasine, leur procédé de préparation et leur utilisation
US4654334A (en)	1987-03-31	Manganese-containing antibiotic agents
US4933364A (en)	1990-06-12	Process for promoting growth and feed efficiency of food producing mammals
EP0252380B1 (fr)	1992-04-15	Antibiotique LL-E19020 alpha et bêta
GB2055094A (en)	1981-02-25	Polyether antibiotic zinc complexes
US4174404A (en)	1979-11-13	Deoxynarasin antibiotics
US4085224A (en)	1978-04-18	Method of increasing feed utilization
CA1173385A (fr)	1984-08-28	Antibiotiques polyethers sous forme de complexes de zinc utilises comme facteurs de croissance des animaux
US4168272A (en)	1979-09-18	Homologs of lasalocid A
US4368265A (en)	1983-01-11	Culturing a strain of nocardia to produce antibiotic X-14868A
US4356264A (en)	1982-10-26	Zinc-containing antibiotic agents
US4670260A (en)	1987-06-02	Antibiotic for animal feeds
US5043333A (en)	1991-08-27	Zinc-lysocelling therapeutic and growth promoting agents
US5089530A (en)	1992-02-18	Novel fermentation product with antiparasitic activity
US4204039A (en)	1980-05-20	Process for producing deoxynarasin antibiotics
CA1207582A (fr)	1986-07-15	Methode pour promouvoir la croissance a l'aide d'agents antibiotiques a teneur de zinc
US4378433A (en)	1983-03-29	Method for producing zinc etheromycin from fermentation broths
DE3511753A1 (de)	1986-10-02	Verwendung von efomycinen als wachstumsfoerderer, efomycine und ihre herstellung