KR880009122A - B아베르멕틴의 제조방법 및 이를 위한 배양물 - Google Patents
B아베르멕틴의 제조방법 및 이를 위한 배양물 Download PDFInfo
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- KR880009122A KR880009122A KR1019880000470A KR880000470A KR880009122A KR 880009122 A KR880009122 A KR 880009122A KR 1019880000470 A KR1019880000470 A KR 1019880000470A KR 880000470 A KR880000470 A KR 880000470A KR 880009122 A KR880009122 A KR 880009122A
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- 238000000034 method Methods 0.000 title claims 10
- 239000005660 Abamectin Substances 0.000 title claims 6
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 title claims 5
- -1 2-methylcyclopropyl Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 15
- 241001468227 Streptomyces avermitilis Species 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 230000000694 effects Effects 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 238000000855 fermentation Methods 0.000 claims 5
- 230000004151 fermentation Effects 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 101710088194 Dehydrogenase Proteins 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000004716 alpha keto acids Chemical class 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 230000001580 bacterial effect Effects 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 230000002950 deficient Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 235000015097 nutrients Nutrition 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 101710116650 FAD-dependent monooxygenase Proteins 0.000 claims 1
- 101710128228 O-methyltransferase Proteins 0.000 claims 1
- 241000187747 Streptomyces Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229950008167 abamectin Drugs 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000011081 inoculation Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000035699 permeability Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 229960005322 streptomycin Drugs 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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- 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
- C12P19/60—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
- C12P19/623—Avermectin; Milbemycin; Ivermectin; C-076
-
- 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
- C12R2001/465—Streptomyces
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Microbiology (AREA)
- Public Health (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Pest Control & Pesticides (AREA)
- Virology (AREA)
- Agronomy & Crop Science (AREA)
- Biomedical Technology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Fodder In General (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (16)
- 측쇄 2-옥소 산 탈수소효소 활성 및 아베르멕틴 B 0-메틸 전이효소 활성이 결핍된 스트렙토마이세스 아베르미틸리스(Streptomyces avermitilis).
- 이의 투과성 세포가, 첨가된[14C-1]-2-옥소이소카프로산으로부터14CO2를 생성할 수 없음을 특징으로 하는, 측쇄 2-옥소 산 탈수소효소 활성 및 아베르멕틴 B0-메틸 전이효소 활성이 결핍된 스트렙토마이세스 아베르미틸리스.
- ATCC 53692[한국기탁번호 : KFCC-10497, 기탁기관 : 한국종균협회, 기탁일 : 1988. 1. 9]와 동일한 특성을 갖는 스트렙토마이세스 아베르미틸리스.
- 스트렙토마이세스 아베르미틸리스 ATCC 53692[한국기탁번호 : KFCC-10497, 기탁기관 : 한국종균협회, 기탁일 : 1988. 1. 9].
- 측쇄 2-옥소 산 탈수소효소 활성 및 아베르멕틴 B0-메틸 전이효소 활성이 결정된 스트렙토마이세스 아베르미틸리스 균주를 질소, 탄소 및 무기염의 동화, 가능한 공급원과 아베르멕틴 생합성에 이용가능한 화합물을 함유하는 수성 영양배지에서 호기성 발효시킴을 특징으로 하여, B아베르멕틴을 제조하는 방법.
- 제5항에 있어서, 에스. 아베르미틸리스가 ATCC 53692[한국기탁번호 : KFCC-10497, 기탁기관 : 한국 종균협회, 기탁일 : 1988. 1. 9]와 동일한 특성을 갖는 방법.
- 제5항에 있어서, 화합물이 일반식(II-A)의 화합물 또는 발효공정 중에 일반식(II-A)의 화합물로 전환 가능한 화합물인 방법.R-COOH (II-A)상기식에서, R은 알파-측쇄그룹이고, -COOH그룹에 부착된 이의 탄소원자가 또한 수소 이외의 2개 이상의 다른 원자 또는 그룹에도 부착된다.
- 제7항에 있어서, R이 알파-측쇄 C3-C8알킬, 알케닐, 알키닐, 알콕시알킬 또는 알킬티오알킬그룹 : 알킬그룹이 알파-측쇄 C2-C5알킬그룹인 C5-C8사이클로 알킬알킬그룹; 메틸렌 또는 하나 이상의 C1-C4알킬그룹 또는 할로원자에 의해 임의 치환될 수 있는 C3-C8사이클로알킬 또는 C5-C8사이클로알케닐그룹 : 또는 포화 또는, 완전 또는 부분적 불포화되고 하나 이상의 C1-C4알킬그룹 또는 할로원자에 의해 임의 치환될 수 있는 3 내지 6원 산소 또는 황-함유 헤테로사이클릭 환인 화합물 또는 발효공정 중에 일반식(II-A)의 화합물로 전환가능한 화합물을 사용하는 방법.
- 제7항에 있어서, 기질 RCOOH로 전환가능한 화합물이 일반식(II-B)의 화합물인 방법.R-(CH2)n-Z (II-B)상기식에서, R은 상기 정의한 바와 같고; n은 0,2,4 또는 6이며; Z은 -CH2OH, -CHO, -COOR4, -CH2NH2또는 -CONHR5[여기서, R4는 H 또는(C1-6)알킬이고; R5는 수소, (C1-4)알킬, -CH(COOH)CH2COOH, -CH(COOH)(CH2)2COOH 또는 -CH(COOH)(CH2)2SCH3이다]이다.
- 제8항에 있어서, R이 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 2-메틸사이클로프로필, 3-사이클로헥세닐, 1-사이클로펜테닐, 1-사이클로헥세닐, 3-메틸사이클로헥실(시스/트랜스), 4-메틸렌사이클로헥실, 3-메틸사이클로부틸, 3-메틸렌사이클로부틸, 3-사이클로펜테닐, 1-사이클로프로필에틸, 3-플루오로사이클로부틸, 4,4-디플루오로사이클로헥실, 이소프로필, 2급-부틸, 2-펜틸, 2,3-디메틸프로필, 2-헥실, 2-펜트-4-에닐, 2-메틸티오에틸, S-2-펜틸, R-2-펜틸, 2-티에닐, 3-티에닐, 4-테트라히드로피라닐, 3-푸릴, 2-클로로티에닐, 3-테트라히드로티에닐, 4-메틸티오-2-부틸, 4-테트라히드로티오피라닐, 4-메톡시-2-부틸 또는 4-메틸티오-2-부틸인 방법.
- 제10항에 있어서, R이 일반식(II-A)의 카복실산으로부터 유도되는 방법.R-COOH (II-A)
- 제11항에 있어서, R이 사이클로펜틸, 사이클로헥실 또는 티에닐인 방법.
- 제10항에 있어서, R이 발효중에 R-COOH로 전환가능한 일반식(II-B)의 화합물로부터 유도되는 방법.R-(CH2)n-Z (II-B)상기식에서 R은 상기 정의한 바와 같고; n은 0,2,4 또는 6이며; Z은-CH2OH, -CHO, -COOR4, -CH2NH2또는 -CONHR5[여기서, R4는 (C1-6)알킬이고, R5는 수소, (C1-4)알킬, -CH(COOH)CH2COOH, -CH(C00H)(CH2)2COOH 또는 -CH(COOH)(CH2)2SCH3이다]이다.
- 제8항에 있어서, R이 알파-측쇄 C3-C8알킬그룹일 경우, 이소프로필 또는 (S)-2급-부틸이 아닌 방법.
- 제8항에 있어서, 에스.아베르미틸리스 균주가 에스.아베르미틸리스 ATCC 53692[한국기탁번호 : KFCC-10497, 기탁기관 : 한국종균협회, 기탁일 : 1988. 1. 9]인 방법.
- 탄소, 질소 및 무기염의 동화가능한 공급원을 함유하고, 일반식(II-A)의 산, 또는 에스.아베르미틸리스에 의해 상기 산으로 전환될 수 있는 화합물이 거의 없는 수성 영양배지 중에서 호기성 조건하에 발효시킬 경우에는, 거의 C-076 아베르멕틴을 생성하지 않지만, 일반식(II-A)의 산 또는, 에스.아베르미틸리스에 의해 상기 산으로 전환될 수 있는 화합물을 함유하는 배지 중에서 발효시킬 경우에는, 실질적으로 B아베르멕틴만을 생성할 수 있으며, 스트렙토마이TP스 아베르미틸리스 ATCC 53567[한국기탁번호 : KFCC-10493, 기탁기관 : 한국종균협회, 기탁번호 : 1988. 1. 9]을 돌연변이시킴을 특징으로 하는 방법으로 수득되는 스트렙토마이세스 속의 신규한 균주.R-COOH (II-A)상기식에서, R은 이소프로필 또는 (S)-2급-부틸이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| KR1019880000506A Expired KR910002225B1 (ko) | 1987-01-23 | 1988-01-23 | 비-천연 데메틸아베르멕틴 및 이의 제조방법 |
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| KR100415395B1 (ko) * | 2000-08-02 | 2004-01-16 | 한국생명공학연구원 | 에버멕틴 ｂｃ-5-ｏ-메칠트랜스퍼라제의 유전자가 파괴된 스트렙토마이세스 에버미티리스 변이균주 및 그의 제조 방법 |
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| GB8811036D0 (en) * | 1988-05-10 | 1988-06-15 | Glaxo Group Ltd | Chemical compounds |
| GB8813760D0 (en) * | 1988-06-10 | 1988-07-13 | American Cyanamid Co | Chemical process |
| GB8815967D0 (en) * | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
| NZ231772A (en) * | 1988-12-23 | 1992-11-25 | Merck & Co Inc | Avermectin derivatives, preparation and parasiticidal compositions thereof |
| NZ231773A (en) * | 1988-12-23 | 1992-09-25 | Merck & Co Inc | Avermectin derivatives, preparation and parasiticidal pharmaceutical compositions thereof |
| US5015630A (en) * | 1989-01-19 | 1991-05-14 | Merck & Co., Inc. | 5-oxime avermectin derivatives |
| US4897383A (en) * | 1989-02-13 | 1990-01-30 | Merck & Co., Inc. | Avermectin derivatives |
| US5252474A (en) * | 1989-03-31 | 1993-10-12 | Merck & Co., Inc. | Cloning genes from Streptomyces avermitilis for avermectin biosynthesis and the methods for their use |
| US5057499A (en) * | 1989-06-02 | 1991-10-15 | Merck & Co. Inc. | Avermectin derivatives |
| US5030622A (en) * | 1989-06-02 | 1991-07-09 | Merck & Co., Inc. | Avermectin derivatives |
| US5023241A (en) * | 1989-07-31 | 1991-06-11 | Merck & Co., Inc. | Avermectin derivatives |
| US5830875A (en) * | 1989-10-30 | 1998-11-03 | Merck & Co., Inc. | 24-and 25-substituted avermectin and milbemycin derivatives |
| JP2888586B2 (ja) * | 1990-03-05 | 1999-05-10 | 社団法人北里研究所 | エバーメクチンの特定成分を選択生産するための微生物およびその選択的製造法 |
| US5169839A (en) * | 1990-05-11 | 1992-12-08 | Merck & Co., Inc. | Derivatives of 3'- and 3"-o-desmethyl avermectin compounds, compositions and methods of treating melmintic and parasitic infections |
| US5208222A (en) * | 1991-03-28 | 1993-05-04 | Merck & Co., Inc. | 4"-and 4'-alkylthio avermectin derivatives |
| US5240915A (en) * | 1991-10-15 | 1993-08-31 | Merck & Co., Inc. | Avermectin derivatives |
| US6103504A (en) * | 1992-03-25 | 2000-08-15 | Pfizer Inc. | Process for production of avermectins and cultures therefor |
| US5292647A (en) * | 1992-11-30 | 1994-03-08 | Eli Lilly And Company | Strain of streptomyces for producing avermectins and processes therewith |
| CN1038330C (zh) * | 1993-07-05 | 1998-05-13 | 塞泰克斯公司 | 阿弗麦菌素的生产与分离 |
| PL181916B1 (en) * | 1993-07-30 | 2001-10-31 | Pfizer | Method of obtaining natural avermectin |
| AU680039B2 (en) * | 1993-10-05 | 1997-07-17 | Pfizer Inc. | Process and antiparasitic intermediates for doramectin |
| FI942725A7 (fi) * | 1993-12-16 | 1995-06-17 | Pfizer | Haaraketjuista alfaketohappodenydrogenaasikompleksia koodaavia geenejä Streptomyces avermitiliksesta |
| US5701591A (en) * | 1995-04-07 | 1997-12-23 | Telecommunications Equipment Corporation | Multi-function interactive communications system with circularly/elliptically polarized signal transmission and reception |
| CN1521180A (zh) * | 1998-02-13 | 2004-08-18 | �Ʒ� | 介导除虫菌素b2：b1比例的除虫链霉菌基因 |
| OA11998A (en) * | 1999-08-12 | 2006-04-18 | Pfizer Prod Inc | Streptomyces avermitilis gene directing the ratio of b2:b1 avermectins. |
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| WO2023203038A1 (en) | 2022-04-19 | 2023-10-26 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
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| KR100415395B1 (ko) * | 2000-08-02 | 2004-01-16 | 한국생명공학연구원 | 에버멕틴 ｂｃ-5-ｏ-메칠트랜스퍼라제의 유전자가 파괴된 스트렙토마이세스 에버미티리스 변이균주 및 그의 제조 방법 |
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