CA1200777A - A-21978c cyclic peptide derivatives and their production - Google Patents

A-21978c cyclic peptide derivatives and their production

Info

Publication number: CA1200777A
Authority: CA; Canada
Prior art keywords: hydrogen; formula; amino; process according; compound
Prior art date: 1982-05-21
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

CA000428102A

Other languages

English (en)

French (fr)

Inventor

Bernard J. Abbott

Manuel Debono

David S. Fukuda

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.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

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.)

1982-05-21

Filing date

1983-05-13

Publication date

1986-02-18

1983-05-13 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1986-02-18 Application granted granted Critical

1986-02-18 Publication of CA1200777A publication Critical patent/CA1200777A/en

Status Expired legal-status Critical Current

Links

108010069514 Cyclic Peptides Proteins 0.000 title claims abstract description 30
102000001189 Cyclic Peptides Human genes 0.000 title claims abstract description 30
238000004519 manufacturing process Methods 0.000 title claims description 5
-1 8-methyldecanoyl Chemical group 0.000 claims abstract description 59
239000001257 hydrogen Substances 0.000 claims abstract description 48
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
238000005947 deacylation reaction Methods 0.000 claims abstract description 36
230000020176 deacylation Effects 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
108090000790 Enzymes Proteins 0.000 claims abstract description 24
102000004190 Enzymes Human genes 0.000 claims abstract description 24
241000187840 Actinoplanes utahensis Species 0.000 claims abstract description 20
150000002431 hydrogen Chemical group 0.000 claims abstract description 13
241001134635 Micromonosporaceae Species 0.000 claims abstract description 12
230000002255 enzymatic effect Effects 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 75
238000000034 method Methods 0.000 claims description 65
244000005700 microbiome Species 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 23
230000008569 process Effects 0.000 claims description 21
125000006239 protecting group Chemical group 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 9
241000187844 Actinoplanes Species 0.000 claims description 7
241000187843 Actinoplanes missouriensis Species 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
241000187712 Actinoplanes sp. Species 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
241000203587 Streptosporangium roseum Species 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 2
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
108020005497 Nuclear hormone receptor Proteins 0.000 claims 1
101150009274 nhr-1 gene Proteins 0.000 claims 1
230000003115 biocidal effect Effects 0.000 abstract description 21
239000003242 anti bacterial agent Substances 0.000 abstract description 14
229940088710 antibiotic agent Drugs 0.000 abstract description 8
239000000543 intermediate Substances 0.000 abstract description 6
125000004122 cyclic group Chemical group 0.000 abstract description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 61
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
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239000002609 medium Substances 0.000 description 33
239000002904 solvent Substances 0.000 description 31
239000000758 substrate Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 24
238000002360 preparation method Methods 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 20
239000000460 chlorine Substances 0.000 description 18
239000002253 acid Substances 0.000 description 17
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229960001866 silicon dioxide Drugs 0.000 description 17
125000000217 alkyl group Chemical group 0.000 description 16
238000012360 testing method Methods 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000000855 fermentation Methods 0.000 description 14
230000004151 fermentation Effects 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000004128 high performance liquid chromatography Methods 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
238000001914 filtration Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
108090000765 processed proteins & peptides Proteins 0.000 description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000012071 phase Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
241000191938 Micrococcus luteus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
150000001413 amino acids Chemical class 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
238000010828 elution Methods 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000013587 production medium Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
239000007787 solid Substances 0.000 description 6
CDAZRCDEDLQYTI-UHFFFAOYSA-N (2,4,5-trichlorophenyl) decanoate Chemical compound CCCCCCCCCC(=O)OC1=CC(Cl)=C(Cl)C=C1Cl CDAZRCDEDLQYTI-UHFFFAOYSA-N 0.000 description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 5
238000000862 absorption spectrum Methods 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000000266 alpha-aminoacyl group Chemical group 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 5
125000001589 carboacyl group Chemical group 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
239000007858 starting material Substances 0.000 description 5
LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 4
239000001888 Peptone Substances 0.000 description 4
108010080698 Peptones Proteins 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 4
229910000396 dipotassium phosphate Inorganic materials 0.000 description 4
235000019797 dipotassium phosphate Nutrition 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
235000019319 peptone Nutrition 0.000 description 4
102000004196 processed proteins & peptides Human genes 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
241000894007 species Species 0.000 description 4
239000007921 spray Substances 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
239000003643 water by type Substances 0.000 description 4
YGPSJZOEDVAXAB-UHFFFAOYSA-N (R)-Kynurenine Natural products OC(=O)C(N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
108010093096 Immobilized Enzymes Proteins 0.000 description 3
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 3
240000004808 Saccharomyces cerevisiae Species 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
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 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
239000008272 agar Substances 0.000 description 3
238000002814 agar dilution Methods 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
238000012474 bioautography Methods 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
239000000306 component Substances 0.000 description 3
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 3
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238000001727 in vivo Methods 0.000 description 3
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UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
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239000003910 polypeptide antibiotic agent Substances 0.000 description 3
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238000003860 storage Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 2
HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
108010083546 A 21978C1 Proteins 0.000 description 2
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ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
230000005526 G1 to G0 transition Effects 0.000 description 2
229910004373 HOAc Inorganic materials 0.000 description 2
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
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GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
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GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 1
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BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
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WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Biotechnology (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CA000428102A 1982-05-21 1983-05-13 A-21978c cyclic peptide derivatives and their production Expired CA1200777A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US38049782A	1982-05-21	1982-05-21
US380,497		1982-05-21

Publications (1)

Publication Number	Publication Date
CA1200777A true CA1200777A (en)	1986-02-18

Family

ID=23501396

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000428102A Expired CA1200777A (en)	1982-05-21	1983-05-13	A-21978c cyclic peptide derivatives and their production

Country Status (16)

Country	Link
KR (1)	KR860001285B1 (de)
AR (1)	AR241943A1 (de)
AT (1)	AT381103B (de)
CA (1)	CA1200777A (de)
DD (1)	DD210285A5 (de)
DK (1)	DK221083A (de)
EG (1)	EG16043A (de)
ES (2)	ES522560A0 (de)
FI (1)	FI79545C (de)
GR (1)	GR78567B (de)
HU (1)	HU195839B (de)
PH (1)	PH22066A (de)
PL (1)	PL242099A1 (de)
PT (1)	PT76700B (de)
RO (1)	RO86724B (de)
ZA (1)	ZA833451B (de)

1983
- 1983-05-13 CA CA000428102A patent/CA1200777A/en not_active Expired
- 1983-05-13 ZA ZA833451A patent/ZA833451B/xx unknown
- 1983-05-16 RO RO110960A patent/RO86724B/ro unknown
- 1983-05-16 PH PH28906A patent/PH22066A/en unknown
- 1983-05-16 AT AT0178283A patent/AT381103B/de not_active IP Right Cessation
- 1983-05-16 PT PT76700A patent/PT76700B/pt unknown
- 1983-05-16 AR AR83293026A patent/AR241943A1/es active
- 1983-05-18 DK DK221083A patent/DK221083A/da not_active Application Discontinuation
- 1983-05-18 EG EG297/83A patent/EG16043A/xx active
- 1983-05-18 FI FI831748A patent/FI79545C/fi not_active IP Right Cessation
- 1983-05-19 KR KR1019830002221A patent/KR860001285B1/ko not_active Expired
- 1983-05-19 ES ES522560A patent/ES522560A0/es active Granted
- 1983-05-19 GR GR71398A patent/GR78567B/el unknown
- 1983-05-20 PL PL24209983A patent/PL242099A1/xx unknown
- 1983-05-20 DD DD83251129A patent/DD210285A5/de unknown
- 1983-05-20 HU HU831795A patent/HU195839B/hu unknown
1984
- 1984-09-14 ES ES535958A patent/ES8506097A1/es not_active Expired

Also Published As

Publication number	Publication date
ES8502731A1 (es)	1985-01-16
RO86724B (ro)	1985-05-01
DD210285A5 (de)	1984-06-06
KR860001285B1 (ko)	1986-09-05
DK221083D0 (da)	1983-05-18
ZA833451B (en)	1984-12-24
PT76700B (en)	1986-03-27
AR241943A1 (es)	1993-01-29
ES522560A0 (es)	1985-01-16
PL242099A1 (en)	1984-07-30
HU195839B (en)	1988-07-28
FI79545B (fi)	1989-09-29
AT381103B (de)	1986-08-25
KR840005075A (ko)	1984-11-03
ES535958A0 (es)	1985-06-16
DK221083A (da)	1983-11-22
FI831748A0 (fi)	1983-05-18
PT76700A (en)	1983-06-01
GR78567B (de)	1984-09-27
ATA178283A (de)	1986-01-15
FI831748L (fi)	1983-11-22
EG16043A (en)	1987-05-30
ES8506097A1 (es)	1985-06-16
FI79545C (fi)	1990-01-10
RO86724A (ro)	1985-04-17
PH22066A (en)	1988-05-20

Legal Events

Date	Code	Title	Description
2003-05-13	MKEX	Expiry

Publication	Publication Date	Title
US4537717A (en)	1985-08-27	Derivatives of A-21978C cyclic peptides
US4482487A (en)	1984-11-13	A-21978C cyclic peptides
US4524135A (en)	1985-06-18	A-21978C cyclic peptides
US4293482A (en)	1981-10-06	A-30912A Nucleus
US5039789A (en)	1991-08-13	A54145 cyclic peptides
USRE32311E (en)	1986-12-16	Derivatives of A-21978C cyclic peptides
USRE32310E (en)	1986-12-16	Derivatives of A-21978C cyclic peptides
US4304716A (en)	1981-12-08	S 31794/F-1 Nucleus
EP0095295B1 (de)	1987-01-14	Cyclische Peptid-Derivate
US4399067A (en)	1983-08-16	Derivatives of A-21978C cyclic peptides
US4299763A (en)	1981-11-10	A-30912B Nucleus
EP0031221B1 (de)	1983-03-02	Cyclische Peptidkerne
US5028590A (en)	1991-07-02	Derivatives of A54145 cyclic peptides
US4293490A (en)	1981-10-06	A-30912H Nuclei
US4293488A (en)	1981-10-06	Derivatives of A-30912B nucleus
CA1216580A (en)	1987-01-13	Derivatives of a-21978c cyclic peptides and their production
US4299762A (en)	1981-11-10	A-30912D Nucleus
EP0337731B1 (de)	1996-01-31	Peptid-Antibiotika
Fukuda et al.	1990	A54145, a new lipopeptide antibiotic complex: microbial and chemical modification
US4558009A (en)	1985-12-10	Process for producing antibiotic A-51568 by fermentation and microorganism
CA1216579A (en)	1987-01-13	Derivatives of a-21978c cyclic peptides
FI79545C (fi)	1990-01-10	Nya cykliska a-21978c-kaernpeptider och foerfarande foer deras framstaellning.
JPH05168466A (ja)	1993-07-02	抗生物質ａ５１５６８因子ａおよびｂを産生する微生物
JPH0238600B2 (de)	1990-08-31
IE50615B1 (en)	1986-05-28	Cyclic peptide nuclei and method of obtaining them by enzymatic deacylation of cyclic peptide antibiotics