CH647790A5 - Makrolidantibiotika. - Google Patents
Makrolidantibiotika. Download PDFInfo
- Publication number
- CH647790A5 CH647790A5 CH8128/80A CH812880A CH647790A5 CH 647790 A5 CH647790 A5 CH 647790A5 CH 8128/80 A CH8128/80 A CH 8128/80A CH 812880 A CH812880 A CH 812880A CH 647790 A5 CH647790 A5 CH 647790A5
- Authority
- CH
- Switzerland
- Prior art keywords
- mycoplanecin
- formula
- compound
- group
- compounds
- Prior art date
Links
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 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 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000004809 thin layer chromatography Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 244000005700 microbiome Species 0.000 claims 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 230000007062 hydrolysis Effects 0.000 claims 5
- 238000006460 hydrolysis reaction Methods 0.000 claims 5
- 238000000862 absorption spectrum Methods 0.000 claims 4
- 239000003638 chemical reducing agent Substances 0.000 claims 4
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 3
- 241000186359 Mycobacterium Species 0.000 claims 3
- 238000010521 absorption reaction Methods 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 241000187480 Mycobacterium smegmatis Species 0.000 claims 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 2
- -1 N-methylvalyl group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims 2
- 238000000921 elemental analysis Methods 0.000 claims 2
- 150000004678 hydrides Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 244000026610 Cynodon dactylon var. affinis Species 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 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 claims 1
- 241000186364 Mycobacterium intracellulare Species 0.000 claims 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 claims 1
- 230000002745 absorbent Effects 0.000 claims 1
- 239000002250 absorbent Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000000973 chemotherapeutic effect Effects 0.000 claims 1
- 238000005553 drilling Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002458 infectious effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 231100000053 low toxicity Toxicity 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 201000008827 tuberculosis Diseases 0.000 claims 1
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000010633 broth Nutrition 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 241000187844 Actinoplanes Species 0.000 description 1
- 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 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 108010057443 mycoplanecin A Proteins 0.000 description 1
- ICFLLAYTOVAMGO-UHFFFAOYSA-N mycoplanecin a Chemical compound CCC(=O)C(=O)N(C)C(C(C)C)C(=O)N1CC(CC)CC1C(=O)N(C)C1C(=O)NC(CC(C)C)C(=O)N2CC(C)CC2C(=O)NC(CCC(C)C)C(=O)N(C)C(C(C)C)C(=O)N2CCCC2C(=O)N(C)C(CC(C)C)C(=O)NCC(=O)OC1C ICFLLAYTOVAMGO-UHFFFAOYSA-N 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000013587 production medium Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- 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
-
- 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
- A61P31/06—Antibacterial agents for tuberculosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/045—Actinoplanes
-
- 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
- Y10S930/17—Vasoactive intestinal peptides; related peptides
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- General Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14165079A JPS5665853A (en) | 1979-11-01 | 1979-11-01 | Mycoplanesin derivative and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH647790A5 true CH647790A5 (de) | 1985-02-15 |
Family
ID=15296975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH8128/80A CH647790A5 (de) | 1979-11-01 | 1980-10-31 | Makrolidantibiotika. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4374764A (en:Method) |
| JP (1) | JPS5665853A (en:Method) |
| AT (1) | AT373868B (en:Method) |
| CH (1) | CH647790A5 (en:Method) |
| DE (1) | DE3041130A1 (en:Method) |
| ES (2) | ES496489A0 (en:Method) |
| FR (1) | FR2468582A1 (en:Method) |
| GB (1) | GB2061946B (en:Method) |
| IT (1) | IT1141632B (en:Method) |
| NL (1) | NL8006011A (en:Method) |
| PH (3) | PH16866A (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58194848A (ja) * | 1982-05-11 | 1983-11-12 | Sankyo Co Ltd | 抗生物質マイコプラネシンｄの製造法 |
| JPS6042399A (ja) * | 1983-08-19 | 1985-03-06 | Sankyo Co Ltd | マイコプラネシン誘導体 |
| ES2056954T3 (es) * | 1987-06-19 | 1994-10-16 | Sandoz Ag | Peptolidos ciclicos. |
| JP4185497B2 (ja) * | 2003-01-17 | 2008-11-26 | 社団法人北里研究所 | 新規ｋ０１−ｂ０１７１物質およびその製造法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1393208A (fr) * | 1961-06-08 | 1965-03-26 | Rhone Poulenc Sa | Nouvel antibiotique et son procédé de préparation par culture d'une nouvelle souche de streptomyces |
| BE741588A (en:Method) * | 1967-10-25 | 1970-05-12 | ||
| JPS495359A (en:Method) * | 1972-05-02 | 1974-01-18 | ||
| CH614931A5 (en:Method) * | 1975-11-04 | 1979-12-28 | Sandoz Ag | |
| JPS6024717B2 (ja) * | 1978-05-24 | 1985-06-14 | 三共株式会社 | 抗生物質マイコプラネシン |
-
1979
- 1979-11-01 JP JP14165079A patent/JPS5665853A/ja active Granted
-
1980
- 1980-10-21 US US06/199,238 patent/US4374764A/en not_active Expired - Lifetime
- 1980-10-31 ES ES496489A patent/ES496489A0/es active Granted
- 1980-10-31 FR FR8023314A patent/FR2468582A1/fr active Granted
- 1980-10-31 CH CH8128/80A patent/CH647790A5/de not_active IP Right Cessation
- 1980-10-31 DE DE19803041130 patent/DE3041130A1/de active Granted
- 1980-10-31 GB GB8035131A patent/GB2061946B/en not_active Expired
- 1980-10-31 IT IT8068680A patent/IT1141632B/it active
- 1980-11-03 AT AT0540780A patent/AT373868B/de not_active IP Right Cessation
- 1980-11-03 NL NL8006011A patent/NL8006011A/xx not_active Application Discontinuation
- 1980-11-03 PH PH24797A patent/PH16866A/en unknown
-
1981
- 1981-09-22 PH PH26237A patent/PH17550A/en unknown
- 1981-09-22 PH PH26238A patent/PH16761A/en unknown
- 1981-11-25 ES ES507441A patent/ES507441A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT8068680A0 (it) | 1980-10-31 |
| FR2468582B1 (en:Method) | 1984-04-20 |
| PH16866A (en) | 1984-03-26 |
| DE3041130C2 (en:Method) | 1990-06-13 |
| NL8006011A (nl) | 1981-06-01 |
| GB2061946B (en) | 1983-07-27 |
| JPS6361959B2 (en:Method) | 1988-11-30 |
| PH17550A (en) | 1984-09-19 |
| ES8207218A1 (es) | 1982-09-01 |
| ES8203417A1 (es) | 1982-04-01 |
| IT1141632B (it) | 1986-10-01 |
| JPS5665853A (en) | 1981-06-03 |
| ES496489A0 (es) | 1982-04-01 |
| PH16761A (en) | 1984-02-15 |
| FR2468582A1 (fr) | 1981-05-08 |
| ES507441A0 (es) | 1982-09-01 |
| AT373868B (de) | 1984-02-27 |
| ATA540780A (de) | 1983-07-15 |
| GB2061946A (en) | 1981-05-20 |
| DE3041130A1 (de) | 1981-05-14 |
| US4374764A (en) | 1983-02-22 |
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