NO803356L - Fremgangsmaate ved fremstilling av macrolidantibiotika - Google Patents

Fremgangsmaate ved fremstilling av macrolidantibiotika

Info

Publication number: NO803356L
Authority: NO; Norway
Prior art keywords: antibiotic; compounds; formula; carbon atoms; compound
Prior art date: 1979-11-09

Application number

NO803356A

Other languages

English (en)

Norwegian (no)

Inventor

Jay Allan Waitz

Walter Joseph Reiblein

Imbi Truumees

Ashit Kumar Ganguly

Yi-Tsung Liu

Olga Sarre

Robert Jaret

Doris Schumacher

Original Assignee

Schering 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.)

1979-11-09

Filing date

1980-11-07

Publication date

1981-05-11

1979-11-09 Priority claimed from US06/093,080 external-priority patent/US4307085A/en

1980-11-07 Application filed by Schering Corp filed Critical Schering Corp

1981-05-11 Publication of NO803356L publication Critical patent/NO803356L/no

Links

238000000034 method Methods 0.000 title claims description 84
238000004519 manufacturing process Methods 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims description 214
WWIDEZOUVSJVHS-ZPQCYHEESA-N (1s,2e,5r,7s,8s,9s,10e,14r,15s,16r)-8-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-15-hydroxy-15-[[(2r,3r,4r,5r,6r)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,7,9-trimethyl-13,17-dioxabicyclo[14.1.0]heptadeca-2,10- Chemical compound O([C@@H]1[C@@H](C)/C=C/C(=O)O[C@@H]([C@@]([C@@H]2O[C@H]2/C=C/C(=O)[C@H](C)C[C@@H]1C)(O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O WWIDEZOUVSJVHS-ZPQCYHEESA-N 0.000 claims description 123
125000004432 carbon atom Chemical group C* 0.000 claims description 100
150000002148 esters Chemical class 0.000 claims description 100
QABCJBNUVVMWAL-HXRJSAKRSA-N (2e,5r,7s,8s,9s,10e,14r,15r)-8-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-15-[[(2r,3r,4r,5r,6r)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,7,9-trimethyl-13,17-dioxabicyclo[14.1.0]heptadeca-2,10-diene-4,12-dione Chemical compound O([C@@H]1[C@@H](C)/C=C/C(=O)O[C@@H]([C@H](C2OC2/C=C/C(=O)[C@H](C)C[C@@H]1C)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O QABCJBNUVVMWAL-HXRJSAKRSA-N 0.000 claims description 82
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 72
229910052739 hydrogen Inorganic materials 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 54
238000002360 preparation method Methods 0.000 claims description 49
239000000203 mixture Substances 0.000 claims description 48
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
-1 mesyloxy, tosyloxy Chemical group 0.000 claims description 41
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
229910052757 nitrogen Inorganic materials 0.000 claims description 36
230000008569 process Effects 0.000 claims description 34
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
239000002904 solvent Substances 0.000 claims description 28
239000003242 anti bacterial agent Substances 0.000 claims description 27
239000002609 medium Substances 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
125000000539 amino acid group Chemical group 0.000 claims description 25
229940088710 antibiotic agent Drugs 0.000 claims description 25
125000000466 oxiranyl group Chemical group 0.000 claims description 24
125000005842 heteroatom Chemical group 0.000 claims description 23
239000011593 sulfur Substances 0.000 claims description 23
229910052717 sulfur Inorganic materials 0.000 claims description 23
239000007858 starting material Substances 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 20
230000007062 hydrolysis Effects 0.000 claims description 20
238000006460 hydrolysis reaction Methods 0.000 claims description 20
241000187708 Micromonospora Species 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
235000015097 nutrients Nutrition 0.000 claims description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 14
244000005700 microbiome Species 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
230000003647 oxidation Effects 0.000 claims description 11
238000007254 oxidation reaction Methods 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 11
239000005864 Sulphur Substances 0.000 claims description 10
239000003638 chemical reducing agent Substances 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
239000003120 macrolide antibiotic agent Substances 0.000 claims description 8
230000002829 reductive effect Effects 0.000 claims description 8
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 8
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 7
229930182566 Gentamicin Natural products 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 7
229960002518 gentamicin Drugs 0.000 claims description 7
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
125000005905 mesyloxy group Chemical group 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
239000012279 sodium borohydride Substances 0.000 claims description 6
229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 6
235000000346 sugar Nutrition 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
238000002955 isolation Methods 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 3
238000011534 incubation Methods 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
150000002540 isothiocyanates Chemical class 0.000 claims description 3
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 3
125000005505 thiomorpholino group Chemical group 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 2
229910001508 alkali metal halide Inorganic materials 0.000 claims description 2
150000008045 alkali metal halides Chemical class 0.000 claims description 2
239000001569 carbon dioxide Substances 0.000 claims description 2
229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
239000004312 hexamethylene tetramine Substances 0.000 claims description 2
235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
150000002429 hydrazines Chemical class 0.000 claims description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
150000002763 monocarboxylic acids Chemical class 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 8
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
230000009466 transformation Effects 0.000 claims 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims 1
235000019256 formaldehyde Nutrition 0.000 claims 1
150000002366 halogen compounds Chemical class 0.000 claims 1
239000001632 sodium acetate Substances 0.000 claims 1
235000017281 sodium acetate Nutrition 0.000 claims 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
230000003115 biocidal effect Effects 0.000 description 49
125000004043 oxo group Chemical group O=* 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 31
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
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 18
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239000003795 chemical substances by application Substances 0.000 description 11
235000019441 ethanol Nutrition 0.000 description 11
229940041514 candida albicans extract Drugs 0.000 description 10
239000008121 dextrose Substances 0.000 description 10
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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IUPCWCLVECYZRV-JZMZINANSA-N rosaramicin Chemical compound O([C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H]([C@@H]2O[C@@]2(C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O IUPCWCLVECYZRV-JZMZINANSA-N 0.000 description 9
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VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical group C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 description 3
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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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
- C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
- 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
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/46—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin
- C12P19/48—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin the cyclohexyl radical being substituted by two or more nitrogen atoms, e.g. destomycin, neamin
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
- 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
- C12R2001/29—Micromonospora

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Microbiology (AREA)
General Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Tropical Medicine & Parasitology (AREA)
Virology (AREA)
Biomedical Technology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO803356A 1979-11-09 1980-11-07 Fremgangsmaate ved fremstilling av macrolidantibiotika NO803356L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US06/093,080 US4307085A (en)	1979-11-09	1979-11-09	Antibiotic AR-5 complex, antibiotics coproduced therewith and derivatives thereof
US10618479A	1979-12-21	1979-12-21
US13033080A	1980-03-14	1980-03-14

Publications (1)

Publication Number	Publication Date
NO803356L true NO803356L (no)	1981-05-11

Family

ID=27377401

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO803356A NO803356L (no)	1979-11-09	1980-11-07	Fremgangsmaate ved fremstilling av macrolidantibiotika

Country Status (10)

Country	Link
EP (1)	EP0033433A1 (fi)
KR (1)	KR830004333A (fi)
AR (1)	AR230648A1 (fi)
DK (1)	DK477280A (fi)
FI (1)	FI803483L (fi)
GR (1)	GR72125B (fi)
IL (1)	IL61437A0 (fi)
NO (1)	NO803356L (fi)
NZ (1)	NZ195507A (fi)
PT (1)	PT72039B (fi)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4487923A (en) *	1981-12-14	1984-12-11	Eli Lilly And Company	Method of preparing 23-monoesters of OMT and DMT
US4528369A (en) *	1982-07-02	1985-07-09	Eli Lilly And Company	20-Dihydro-20-deoxy-23-de(mycinosyloxy)tylosin
US4629786A (en) *	1983-02-28	1986-12-16	Eli Lilly And Company	C-20- and C-23 modified macrolide derivatives
US4468511A (en) *	1983-02-28	1984-08-28	Eli Lilly And Company	C-20- And C-23-Modified macrolide derivatives
GB8405087D0 (en) *	1984-02-27	1984-04-04	Omura S	Antibiotic
US4920103A (en) *	1986-09-29	1990-04-24	Eli Lilly And Company	Modifications of mycinose and 3-O-demethylmycinose in tylosin-type macrolides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1125203A (en) *	1978-05-10	1982-06-08	Toyo Jozo Company, Ltd.	Macrolide antibiotics from micromonospora

1980
- 1980-11-07 NO NO803356A patent/NO803356L/no unknown
- 1980-11-07 FI FI803483A patent/FI803483L/fi not_active Application Discontinuation
- 1980-11-07 PT PT72039A patent/PT72039B/pt unknown
- 1980-11-08 GR GR63318A patent/GR72125B/el unknown
- 1980-11-08 KR KR1019800004295A patent/KR830004333A/ko unknown
- 1980-11-09 IL IL61437A patent/IL61437A0/xx unknown
- 1980-11-10 NZ NZ195507A patent/NZ195507A/en unknown
- 1980-11-10 AR AR283172A patent/AR230648A1/es active
- 1980-11-10 EP EP80810346A patent/EP0033433A1/en not_active Ceased
- 1980-11-10 DK DK477280A patent/DK477280A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
FI803483L (fi)	1981-05-10
GR72125B (fi)	1983-09-16
IL61437A0 (en)	1980-12-31
DK477280A (da)	1981-05-10
PT72039B (pt)	1982-06-20
NZ195507A (en)	1985-05-31
AR230648A1 (es)	1984-05-31
KR830004333A (ko)	1983-07-09
PT72039A (en)	1980-12-01
EP0033433A1 (en)	1981-08-12

Publication	Publication Date	Title
EP0042250B1 (en)	1984-03-07	Macrolide antiobiotics
JPH082907B2 (ja)	1996-01-17	新規免疫抑制剤
US4559301A (en)	1985-12-17	Process for preparing macrocin derivatives
DK172545B1 (da)	1998-12-14	Antibiotiske glycopeptider og fremgangsmåde til deres fremstilling
NO160011B (no)	1988-11-21	Mikrobiologisk fremgangsmaate for fremstilling av antracyklin-derivater.
NO803356L (no)	1981-05-11	Fremgangsmaate ved fremstilling av macrolidantibiotika
US4705688A (en)	1987-11-10	Antibiotic LL-E19020 α and β
US4234690A (en)	1980-11-18	Method for producing rosaramicin (rosamicin)
CA1158579A (en)	1983-12-13	Antibiotic ar-5 complex, derivatives thereof and methods for production thereof
US4183920A (en)	1980-01-15	4-N-Acyl, 2'-N-acyl and 4,2'-N,N'-diacylfortimicin E derivatives
US4152424A (en)	1979-05-01	Antibiotic 1745A/X and methods for the production thereof
EP0121328B1 (en)	1988-01-20	Macrolide derivatives
EP0245012A1 (en)	1987-11-11	Method for the preparation of 14-hydroxy-6-0-methyl-erythromycin A
KR860001997B1 (ko)	1986-11-12	데(미시노실옥시)틸로신 유도체의 제조방법
EP0002589B1 (en)	1982-06-30	A-40104 antibiotics, their preparation, and formulations containing them
NZ197360A (en)	1984-03-30	23-(demycinosyloxy) tylosins and veterinary formulations; preparation of domt and dihydrodomt
US3207750A (en)	1965-09-21	Derivatives of decoyinine
US4656258A (en)	1987-04-07	Macrocin derivatives
EP0056290A2 (en)	1982-07-21	Novel macrolidic antibiotics having antibiotic activity, process and microorganism for their preparation, and related pharmaceutical compositions
EP0531638B1 (en)	1998-01-07	Antibiotic LL-E19020 alpha 1
EP0045157B1 (en)	1984-04-18	Macrolide antibiotics, their preparation and veterinary compositions containing them
JPS6363554B2 (fi)	1988-12-07
US4367287A (en)	1983-01-04	Process of producing antibiotic AR-5 complex
US4205164A (en)	1980-05-27	Antibiotic A201C, A201D and A201E
US4904644A (en)	1990-02-27	Antimicrobial compound isolated from Actinomadura fulva subsp indica