JPS59205392A - アクタプラニン抗生物質 - Google Patents
アクタプラニン抗生物質Info
- Publication number
- JPS59205392A JPS59205392A JP59086015A JP8601584A JPS59205392A JP S59205392 A JPS59205392 A JP S59205392A JP 59086015 A JP59086015 A JP 59086015A JP 8601584 A JP8601584 A JP 8601584A JP S59205392 A JPS59205392 A JP S59205392A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- mannose
- actaplanin
- hydrolysis
- actaplanins
- 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
- 108010020588 actaplanin Proteins 0.000 title claims description 41
- BDNDRNLSLGGULA-UHFFFAOYSA-N actaplanin Chemical compound C=1C2=CC=C(O)C=1C1=C(OC3C(C(O)C(O)C(CO)O3)O)C=C(O)C=C1C(C(=O)OC)NC(=O)C1NC(=O)C2NC(=O)C2NC(=O)C(C=3C=C(C(=C(O)C=3)C)OC=3C(O)=CC=C(C=3)C(N)C(=O)N3)NC(=O)C3CC(C=C3)=CC=C3OC(C=3OC4C(C(O)C(O)C(CO)O4)O)=CC2=CC=3OC(C(=C2)Cl)=CC=C2C1OC1CC(N)C(O)C(C)O1 BDNDRNLSLGGULA-UHFFFAOYSA-N 0.000 title claims description 33
- 229950002379 actaplanin Drugs 0.000 title claims description 32
- 230000003115 biocidal effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 16
- 239000008103 glucose Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- QMDPAEWMWMZYOS-RCBBXDANSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxy-1-[(3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]hexan-1-one Chemical compound C[C@@H]1OC(C(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)[C@H](O)[C@H](O)[C@H]1O QMDPAEWMWMZYOS-RCBBXDANSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000600 disaccharide group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 description 41
- 238000006460 hydrolysis reaction Methods 0.000 description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 235000000346 sugar Nutrition 0.000 description 9
- 238000005903 acid hydrolysis reaction Methods 0.000 description 6
- 150000002016 disaccharides Chemical class 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000004043 trisaccharides Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000282849 Ruminantia Species 0.000 description 3
- BDNDRNLSLGGULA-DYXFHWNWSA-N actaplanin g Chemical compound C=1C2=CC=C(O)C=1C1=C(OC3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=C(O)C=C1C(C(=O)OC)NC(=O)C1NC(=O)C2NC(=O)C2NC(=O)C(C=3C=C(C(=C(O)C=3)C)OC=3C(O)=CC=C(C=3)C(N)C(=O)N3)NC(=O)C3CC(C=C3)=CC=C3OC(C=3OC4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=CC2=CC=3OC(C(=C2)Cl)=CC=C2C1OC1C[C@@H](N)[C@H](O)[C@@H](C)O1 BDNDRNLSLGGULA-DYXFHWNWSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- BCXWYYWMAHVAHK-VNYVUCJKSA-N e41y23b9dj Chemical compound C=1C2=CC=C(O)C=1C1=C(OC3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=C(O)C=C1C(C(=O)OC)NC(=O)C1NC(=O)C2NC(=O)C2NC(=O)C(C=3C=C(C(=C(OC4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C=3)C)OC=3C(O)=CC=C(C=3)C(N)C(=O)N3)NC(=O)C3CC(C=C3)=CC=C3OC(C=3OC4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)OC4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=CC2=CC=3OC(C(=C2)Cl)=CC=C2C1OC1C[C@@H](N)[C@H](O)[C@@H](C)O1 BCXWYYWMAHVAHK-VNYVUCJKSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000002303 glucose derivatives Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- -1 mannose sugars Chemical class 0.000 description 2
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YRMCBQLZVBXOSJ-PCFSSPOYSA-N (e)-3-[(6r,6as)-4-hydroxy-6-methoxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]prop-2-enamide Chemical compound CO[C@H]1NC2=C(O)C(C)=CC=C2C(=O)N2C=C(\C=C\C(N)=O)C[C@@H]12 YRMCBQLZVBXOSJ-PCFSSPOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Chemical group CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical group C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Chemical group CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- KAKQAAZRQJPUOS-DNGYIYSOSA-N actaplanin b1 Chemical compound C=1C2=CC=C(O)C=1C1=C(OC3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=C(O)C=C1C(C(=O)OC)NC(=O)C1NC(=O)C2NC(=O)C2NC(=O)C(C=3C=C(C(=C(OC4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C=3)C)OC=3C(O)=CC=C(C=3)C(N)C(=O)N3)NC(=O)C3CC(C=C3)=CC=C3OC(C=3OC4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)OC4[C@H]([C@@H](O)[C@H](O)[C@@H](C)O4)O)=CC2=CC=3OC(C(=C2)Cl)=CC=C2C1OC1C[C@@H](N)[C@H](O)[C@@H](C)O1 KAKQAAZRQJPUOS-DNGYIYSOSA-N 0.000 description 1
- BZRNMBZEZQLBTO-ZFLTWHPGSA-N actaplanin b2 Chemical compound C=1C2=CC=C(O)C=1C1=C(OC3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=C(O)C=C1C(C(=O)OC)NC(=O)C1NC(=O)C2NC(=O)C2NC(=O)C(C=3C=C(C(=C(OC4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C=3)C)OC=3C(O)=CC=C(C=3)C(N)C(=O)N3)NC(=O)C3CC(C=C3)=CC=C3OC(C=3OC4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=CC2=CC=3OC(C(=C2)Cl)=CC=C2C1OC1C[C@@H](N)[C@H](O)[C@@H](C)O1 BZRNMBZEZQLBTO-ZFLTWHPGSA-N 0.000 description 1
- INTBFGWQZKLILS-IZFAQJFJSA-N actaplanin b3 Chemical compound C=1C2=CC=C(O)C=1C1=C(OC3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=C(O)C=C1C(C(=O)OC)NC(=O)C1NC(=O)C2NC(=O)C2NC(=O)C(C=3C=C(C(=C(O)C=3)C)OC=3C(O)=CC=C(C=3)C(N)C(=O)N3)NC(=O)C3CC(C=C3)=CC=C3OC(C=3OC4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)OC4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=CC2=CC=3OC(C(=C2)Cl)=CC=C2C1OC1C[C@@H](N)[C@H](O)[C@@H](C)O1 INTBFGWQZKLILS-IZFAQJFJSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- UNXNGGMLCSMSLH-UHFFFAOYSA-N dihydrogen phosphate;triethylazanium Chemical compound OP(O)(O)=O.CCN(CC)CC UNXNGGMLCSMSLH-UHFFFAOYSA-N 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002704 mannoses Chemical class 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- FLZWAAFMRTZQGV-ULZIYQADSA-N n-[(2r,3r,4r,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2r,3s,4s,5r)-4,5,6-trihydroxy-1-oxo-2-[(2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexan-3-yl]oxyoxan-3-yl]acetamide Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H](C=O)[C@H]([C@@H](O)[C@H](O)CO)O[C@@H]1[C@H](NC(C)=O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 FLZWAAFMRTZQGV-ULZIYQADSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/19—Antibiotic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US488967 | 1983-04-27 | ||
| US06/488,967 US4479897A (en) | 1983-04-27 | 1983-04-27 | Actaplanin antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS59205392A true JPS59205392A (ja) | 1984-11-20 |
Family
ID=23941856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59086015A Pending JPS59205392A (ja) | 1983-04-27 | 1984-04-26 | アクタプラニン抗生物質 |
Country Status (9)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8307847D0 (en) * | 1983-03-22 | 1983-04-27 | Lepetit Spa | Antibiotics l 17054 and l 17046 |
| US4558036A (en) * | 1984-02-17 | 1985-12-10 | Eli Lilly And Company | Actaplanin antibiotics |
| US4547488A (en) * | 1984-04-16 | 1985-10-15 | Eli Lilly And Company | Antibiotic M43D, pharmaceutical compositions and method of use |
| EP0368949A1 (en) * | 1988-02-10 | 1990-05-23 | Beecham Group Plc | Novel antibiotic compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3952095A (en) * | 1972-06-02 | 1976-04-20 | Eli Lilly And Company | Novel antibiotic and a process for the production thereof |
| US3928571A (en) * | 1972-12-15 | 1975-12-23 | Lilly Co Eli | Ruminant feed utilization improvement |
| US4064233A (en) * | 1974-12-17 | 1977-12-20 | Eli Lilly And Company | Antibiotic A-4696 |
| US4115552A (en) * | 1976-04-19 | 1978-09-19 | Eli Lilly And Company | Factor A and B of antibiotic A-4696 |
| US4322406A (en) * | 1980-12-18 | 1982-03-30 | Eli Lilly And Company | Antibiotic A-4696 factors B1, B2, B3, C1a, C3 and E1 |
| US4322343A (en) * | 1980-12-18 | 1982-03-30 | Eli Lilly And Company | Pseudo-aglycone of actaplanin |
| NZ199196A (en) * | 1980-12-18 | 1985-01-31 | Lilly Co Eli | Antibiotic a-4696 factor g and growth-promoting compositions;actinoplanes missouriensis atcc 31681 |
-
1983
- 1983-04-27 US US06/488,967 patent/US4479897A/en not_active Expired - Fee Related
-
1984
- 1984-04-25 IL IL71625A patent/IL71625A0/xx unknown
- 1984-04-25 GB GB08410585A patent/GB2138822B/en not_active Expired
- 1984-04-25 EP EP84302779A patent/EP0124343A1/en not_active Withdrawn
- 1984-04-26 HU HU841620A patent/HU189869B/hu unknown
- 1984-04-26 KR KR1019840002239A patent/KR880000133B1/ko not_active Expired
- 1984-04-26 JP JP59086015A patent/JPS59205392A/ja active Pending
- 1984-04-26 GR GR74510A patent/GR79574B/el unknown
- 1984-04-26 DK DK210284A patent/DK210284A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2138822A (en) | 1984-10-31 |
| KR840008367A (ko) | 1984-12-14 |
| US4479897A (en) | 1984-10-30 |
| GB8410585D0 (en) | 1984-05-31 |
| HUT34043A (en) | 1985-01-28 |
| EP0124343A1 (en) | 1984-11-07 |
| DK210284A (da) | 1984-10-28 |
| IL71625A0 (en) | 1984-07-31 |
| HU189869B (en) | 1986-08-28 |
| KR880000133B1 (ko) | 1988-03-12 |
| DK210284D0 (da) | 1984-04-26 |
| GR79574B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-10-30 |
| GB2138822B (en) | 1986-08-28 |
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