CS207397B2 - Method of preparation of the new anthelmintic compounds - Google Patents

Method of preparation of the new anthelmintic compounds Download PDF

Info

Publication number: CS207397B2
Authority: CS; Czechoslovakia
Prior art keywords: compounds; fractions; liters; medium; mixture
Prior art date: 1976-04-19

Application number

CS772465A

Other languages

Czech (cs)

English (en)

Inventor

Georg Albers-Schonberg

Richard W Burg

Thomas W Miller

Robert E Ormond

Hyman S Wallick

Original Assignee

Merck & Co Inc

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.)

1976-04-19

Filing date

1977-04-14

Publication date

1981-07-31

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24722350&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CS207397(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1977-04-14 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1981-07-31 Publication of CS207397B2 publication Critical patent/CS207397B2/cs

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 124
238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 5
230000000507 anthelmentic effect Effects 0.000 title description 3
238000000855 fermentation Methods 0.000 claims abstract description 26
230000004151 fermentation Effects 0.000 claims abstract description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
235000015097 nutrients Nutrition 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
239000002904 solvent Substances 0.000 claims description 19
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239000003960 organic solvent Substances 0.000 claims description 8
238000000605 extraction Methods 0.000 claims description 7
238000001914 filtration Methods 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
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 description 2
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230000003115 biocidal effect Effects 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
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239000008280 blood Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
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238000002425 crystallisation Methods 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
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239000003480 eluent Substances 0.000 description 1
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239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
239000012526 feed medium Substances 0.000 description 1
210000002196 fr. b Anatomy 0.000 description 1
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239000000499 gel Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
238000004896 high resolution mass spectrometry Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
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239000002917 insecticide Substances 0.000 description 1
235000001705 insufficient nutrition Nutrition 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
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230000000366 juvenile effect Effects 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000004571 lime Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
210000003563 lymphoid tissue Anatomy 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000401 methanolic extract Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
230000001617 migratory effect Effects 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
239000013642 negative control Substances 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000006916 nutrient agar Substances 0.000 description 1
239000006877 oatmeal agar Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
230000000590 parasiticidal effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
244000000003 plant pathogen Species 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
229910001380 potassium hypophosphite Inorganic materials 0.000 description 1
244000144977 poultry Species 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
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239000013587 production medium Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000033458 reproduction Effects 0.000 description 1
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
230000028070 sporulation Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
210000004304 subcutaneous tissue Anatomy 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000003826 tablet Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 0.000 description 1

Classifications

- 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
- 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
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- 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
- 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
- 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
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biochemistry (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Tropical Medicine & Parasitology (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
General Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Microbiology (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Saccharide Compounds (AREA)

CS772465A 1976-04-19 1977-04-14 Method of preparation of the new anthelmintic compounds CS207397B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US67832876A	1976-04-19	1976-04-19

Publications (1)

Publication Number	Publication Date
CS207397B2 true CS207397B2 (en)	1981-07-31

Family

ID=24722350

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS772465A CS207397B2 (en)	1976-04-19	1977-04-14	Method of preparation of the new anthelmintic compounds

Country Status (40)

Country	Link
US (1)	US4310519A (fr)
JP (1)	JPS52151197A (fr)
AR (1)	AR215000A1 (fr)
AT (1)	AT357503B (fr)
AU (1)	AU513641B2 (fr)
BE (1)	BE853702A (fr)
BG (1)	BG35900A3 (fr)
CA (1)	CA1098063A (fr)
CH (1)	CH639422A5 (fr)
CS (1)	CS207397B2 (fr)
CY (1)	CY1114A (fr)
DD (1)	DD137727A5 (fr)
DE (1)	DE2717040C2 (fr)
DK (1)	DK146514C (fr)
ES (1)	ES457932A1 (fr)
FI (1)	FI57781C (fr)
FR (1)	FR2348970A1 (fr)
GB (1)	GB1573955A (fr)
GR (1)	GR63128B (fr)
GT (1)	GT197746150A (fr)
HK (1)	HK38481A (fr)
HU (1)	HU179041B (fr)
IE (1)	IE44822B1 (fr)
IL (1)	IL51854A (fr)
IT (1)	IT1106424B (fr)
KE (1)	KE3141A (fr)
LU (1)	LU77152A1 (fr)
MY (1)	MY8200087A (fr)
NL (3)	NL188859C (fr)
NO (1)	NO148856C (fr)
NZ (1)	NZ183847A (fr)
OA (1)	OA05638A (fr)
PL (1)	PL108004B1 (fr)
PT (1)	PT66445B (fr)
RO (1)	RO71785A (fr)
SE (1)	SE434277B (fr)
SU (1)	SU716524A3 (fr)
YU (1)	YU40814B (fr)
ZA (1)	ZA772345B (fr)
ZM (1)	ZM3677A1 (fr)

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1977
- 1977-03-29 SE SE7703592A patent/SE434277B/xx not_active IP Right Cessation
- 1977-04-04 DK DK149077A patent/DK146514C/da active Protection Beyond IP Right Term
- 1977-04-05 NO NO771211A patent/NO148856C/no unknown
- 1977-04-06 NL NLAANVRAGE7703810,A patent/NL188859C/xx active Protection Beyond IP Right Term
- 1977-04-07 FI FI771124A patent/FI57781C/fi not_active IP Right Cessation
- 1977-04-11 IL IL51854A patent/IL51854A/xx unknown
- 1977-04-13 AU AU24220/77A patent/AU513641B2/en not_active Expired
- 1977-04-13 NZ NZ183847A patent/NZ183847A/xx unknown
- 1977-04-13 CA CA276,126A patent/CA1098063A/fr not_active Expired
- 1977-04-13 GB GB15402/77A patent/GB1573955A/en not_active Expired
- 1977-04-13 CY CY1114A patent/CY1114A/xx unknown
- 1977-04-14 RO RO7790023A patent/RO71785A/fr unknown
- 1977-04-14 CS CS772465A patent/CS207397B2/cs unknown
- 1977-04-15 DD DD77198421A patent/DD137727A5/xx unknown
- 1977-04-15 IE IE785/77A patent/IE44822B1/en not_active IP Right Cessation
- 1977-04-15 FR FR7711432A patent/FR2348970A1/fr active Granted
- 1977-04-15 PT PT66445A patent/PT66445B/pt unknown
- 1977-04-15 YU YU1001/77A patent/YU40814B/xx unknown
- 1977-04-15 AT AT266277A patent/AT357503B/de not_active IP Right Cessation
- 1977-04-15 IT IT48991/77A patent/IT1106424B/it active
- 1977-04-15 AR AR267229A patent/AR215000A1/es active
- 1977-04-15 GR GR53219A patent/GR63128B/el unknown
- 1977-04-16 PL PL1977197448A patent/PL108004B1/pl unknown
- 1977-04-18 SU SU772474802A patent/SU716524A3/ru active
- 1977-04-18 HU HU77ME2059A patent/HU179041B/hu unknown
- 1977-04-18 LU LU77152A patent/LU77152A1/xx unknown
- 1977-04-18 BG BG036028A patent/BG35900A3/xx unknown
- 1977-04-18 GT GT197746150A patent/GT197746150A/es unknown
- 1977-04-18 ZM ZM7736A patent/ZM3677A1/xx unknown
- 1977-04-18 DE DE2717040A patent/DE2717040C2/de not_active Expired
- 1977-04-18 ES ES457932A patent/ES457932A1/es not_active Expired
- 1977-04-18 OA OA56144A patent/OA05638A/fr unknown
- 1977-04-18 BE BE176805A patent/BE853702A/fr not_active IP Right Cessation
- 1977-04-18 CH CH477177A patent/CH639422A5/de not_active IP Right Cessation
- 1977-04-18 ZA ZA00772345A patent/ZA772345B/xx unknown
- 1977-04-19 JP JP4416977A patent/JPS52151197A/ja active Granted
1978
- 1978-09-08 US US05/940,682 patent/US4310519A/en not_active Expired - Lifetime
1981
- 1981-07-09 KE KE3141A patent/KE3141A/xx unknown
- 1981-07-30 HK HK384/81A patent/HK38481A/en unknown
1982
- 1982-12-30 MY MY87/82A patent/MY8200087A/xx unknown
1995
- 1995-04-21 NL NL950005C patent/NL950005I2/nl unknown
1997
- 1997-03-03 NL NL971001C patent/NL971001I2/nl unknown

Also Published As

Publication number	Publication date
FI57781C (fi)	1980-10-10
NZ183847A (en)	1980-05-08
DK149077A (da)	1977-10-20
CA1098063A (fr)	1981-03-24
NL950005I1 (nl)	1995-06-16
GT197746150A (es)	1978-10-10
HK38481A (en)	1981-08-07
PT66445A (en)	1977-05-01
ATA266277A (de)	1979-12-15
NL950005I2 (nl)	1997-02-03
BE853702A (fr)	1977-10-18
KE3141A (en)	1981-07-24
NO771211L (no)	1977-10-20
AU513641B2 (en)	1980-12-11
NL971001I1 (nl)	1997-06-02
SU716524A3 (ru)	1980-02-15
DE2717040A1 (de)	1977-11-10
CY1114A (en)	1981-12-04
ZA772345B (en)	1978-12-27
NL7703810A (nl)	1977-10-21
LU77152A1 (fr)	1977-11-17
PL108004B1 (pl)	1980-03-31
OA05638A (fr)	1981-04-30
JPH0217558B2 (fr)	1990-04-20
GB1573955A (en)	1980-08-28
NO148856C (no)	1983-12-28
DE2717040C2 (de)	1986-09-18
PT66445B (en)	1979-03-09
AR215000A1 (es)	1979-08-31
DK146514B (da)	1983-10-24
DK146514C (da)	1984-04-09
FR2348970B1 (fr)	1980-04-25
NL188859C (nl)	1992-10-16
HU179041B (en)	1982-08-28
FI771124A7 (fr)	1977-10-20
IE44822B1 (en)	1982-04-07
IL51854A (en)	1980-03-31
DD137727A5 (de)	1979-09-19
IT1106424B (it)	1985-11-11
NL188859B (nl)	1992-05-18
US4310519A (en)	1982-01-12
JPS52151197A (en)	1977-12-15
YU100177A (en)	1983-02-28
ES457932A1 (es)	1978-06-01
FI57781B (fi)	1980-06-30
CH639422A5 (en)	1983-11-15
BG35900A3 (bg)	1984-07-16
NL971001I2 (nl)	1997-08-01
RO71785A (fr)	1982-10-26
IL51854A0 (en)	1977-06-30
GR63128B (en)	1979-09-17
ZM3677A1 (en)	1978-08-21
YU40814B (en)	1986-06-30
AT357503B (de)	1980-07-10
AU2422077A (en)	1978-10-19
SE434277B (sv)	1984-07-16
SE7703592L (sv)	1977-10-20
MY8200087A (en)	1982-12-31
NO148856B (no)	1983-09-19
IE44822L (en)	1977-10-19
FR2348970A1 (fr)	1977-11-18

Publication	Publication Date	Title
CS207397B2 (en)	1981-07-31	Method of preparation of the new anthelmintic compounds
EP0170006B1 (fr)	1992-07-08	Agents et leurs méthodes de production, méthodes et compositions contenant ces agents pour lutter contre les infections dûes aux helminthes, aux arthropodes, aux ectoparasites et aux acariens
US4429042A (en)	1984-01-31	Strain of Streptomyces for producing antiparasitic compounds
US5510372A (en)	1996-04-23	Antiparasitic macrolide antiobiotics
CA2021894C (fr)	1996-09-17	Agent antiparasite
AU615921B2 (en)	1991-10-17	Antibiotic ksb-1939 compounds and production process thereof as well as pesticidal agents containing same
US5317030A (en)	1994-05-31	Method and compositions for helmintic, arthropod ectoparasitic and acaridal infections with novel agents
US4869901A (en)	1989-09-26	Method and compositions for helmintic, arthropod ectoparasitic and acaridal infections with novel agents
NZ227005A (en)	1991-08-27	Polycyclic compounds, derivatives of paraherquamide, from fermentation of penicillium charlesii mf 5123; pesticidal compositions
AU632508B2 (en)	1993-01-07	Anthelmintic bioconversion products
CA2013412A1 (fr)	1990-09-30	Produits de bioconversion anthelmintiques
JPH06102675B2 (ja)	1994-12-14	アベルメクチン化合物のグリコシル化方法
US5198464A (en)	1993-03-30	Method and compositions for helmintic, arthropod ectoparasitic and acaridal infections with novel agents
AU642295B2 (en)	1993-10-14	28-hydroxy ivermectin aglycone
JPH07505280A (ja)	1995-06-15	ストレプトマイセス　アベルミチリス株によりグリコシル化されたアベルメクチン化合物
JPS61257989A (ja)	1986-11-15	微生物の新規な駆虫性発酵生産物
EP0050964B1 (fr)	1987-03-04	Lactones macrocycliques, leur production et leur utilisation comme parasiticides, leurs compositions, et une culture biologique propre à leur obtention
EP0469843A1 (fr)	1992-02-05	Nouveau produit de fermentation avec activité antiparasitaire
NZ230948A (en)	1992-05-26	Avermectin derivatives, preparation by fermentation, pharmaceutical and insecticidal compositions thereof
JPH0586065A (ja)	1993-04-06	既知の微生物から生産される新規アベルメクチン
JPH0665279A (ja)	1994-03-08	５β−及び１３−βイベルメクチンモノグルコピラノシド
JPH04304895A (ja)	1992-10-28	新規なイベルメクチン化合物の製造方法