DK171025B1 - Makrolidforbindelser, farmaceutiske, veterinære og ikke-farmaceutiske pesticide præparater indeholdende forbindelserne, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige mider og fremgangsmåde til fremstilling af forbindelserne samt forbindelser til anvendelse ved fremstilling af makrolidforbindelserne - Google Patents

Makrolidforbindelser, farmaceutiske, veterinære og ikke-farmaceutiske pesticide præparater indeholdende forbindelserne, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige mider og fremgangsmåde til fremstilling af forbindelserne samt forbindelser til anvendelse ved fremstilling af makrolidforbindelserne Download PDF

Info

Publication number: DK171025B1
Authority: DK; Denmark
Prior art keywords: group; compounds; formula; compound; hydrogen atom
Prior art date: 1988-05-10

Application number

DK227389A

Other languages

Danish (da)

English (en)

Other versions

DK227389A (da

DK227389D0 (da

Inventor

Michael V J Ramsay

Edward P Tiley

Richard Bell

Derek R Sutherland

Peter D Howes

Original Assignee

American Cyanamid 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.)

1988-05-10

Filing date

1989-05-09

Publication date

1996-04-22

1989-05-09 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1989-05-09 Publication of DK227389D0 publication Critical patent/DK227389D0/da

1989-11-11 Publication of DK227389A publication Critical patent/DK227389A/da

1996-04-22 Application granted granted Critical

1996-04-22 Publication of DK171025B1 publication Critical patent/DK171025B1/da

Links

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DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
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238000005903 acid hydrolysis reaction Methods 0.000 description 1
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239000011149 active material Substances 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
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239000012874 anionic emulsifier Substances 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
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BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
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229910052801 chlorine Inorganic materials 0.000 description 1
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239000008119 colloidal silica Substances 0.000 description 1
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238000001816 cooling Methods 0.000 description 1
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239000012043 crude product Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
PWEOPMBMTXREGV-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O PWEOPMBMTXREGV-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
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IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
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239000000428 dust Substances 0.000 description 1
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150000004820 halides Chemical class 0.000 description 1
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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238000002513 implantation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
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235000019341 magnesium sulphate Nutrition 0.000 description 1
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238000004519 manufacturing process Methods 0.000 description 1
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238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
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239000010703 silicon Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
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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
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02M—SUPPLYING COMBUSTION ENGINES IN GENERAL WITH COMBUSTIBLE MIXTURES OR CONSTITUENTS THEREOF
- F02M7/00—Carburettors with means for influencing, e.g. enriching or keeping constant, fuel/air ratio of charge under varying conditions

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Dentistry (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Tropical Medicine & Parasitology (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Mechanical Engineering (AREA)
General Engineering & Computer Science (AREA)
Combustion & Propulsion (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyrane Compounds (AREA)
Furan Compounds (AREA)
Devices For Conveying Motion By Means Of Endless Flexible Members (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DK227389A 1988-05-10 1989-05-09 Makrolidforbindelser, farmaceutiske, veterinære og ikke-farmaceutiske pesticide præparater indeholdende forbindelserne, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige mider og fremgangsmåde til fremstilling af forbindelserne samt forbindelser til anvendelse ved fremstilling af makrolidforbindelserne DK171025B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB888811037A GB8811037D0 (en)	1988-05-10	1988-05-10	Chemical compounds
GB8811037		1988-05-10

Publications (3)

Publication Number	Publication Date
DK227389D0 DK227389D0 (da)	1989-05-09
DK227389A DK227389A (da)	1989-11-11
DK171025B1 true DK171025B1 (da)	1996-04-22

Family

ID=10636654

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK227389A DK171025B1 (da)	1988-05-10	1989-05-09	Makrolidforbindelser, farmaceutiske, veterinære og ikke-farmaceutiske pesticide præparater indeholdende forbindelserne, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige mider og fremgangsmåde til fremstilling af forbindelserne samt forbindelser til anvendelse ved fremstilling af makrolidforbindelserne

Country Status (18)

Country	Link
US (1)	US5112854A (fr)
EP (1)	EP0341972B1 (fr)
JP (1)	JP2506189B2 (fr)
KR (1)	KR960013441B1 (fr)
AT (1)	ATE142211T1 (fr)
AU (1)	AU631792B2 (fr)
BR (1)	BR8902169A (fr)
CA (1)	CA1333599C (fr)
DD (1)	DD289531A5 (fr)
DE (1)	DE68927070T2 (fr)
DK (1)	DK171025B1 (fr)
ES (1)	ES2091761T3 (fr)
GB (1)	GB8811037D0 (fr)
GR (1)	GR3021375T3 (fr)
HU (1)	HU204833B (fr)
NZ (1)	NZ229051A (fr)
PT (1)	PT90508B (fr)
ZA (1)	ZA893428B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE72215B1 (en) *	1988-05-10	1997-04-09	American Cyanamid Co	Macrolide compounds
NZ233680A (en) *	1989-05-17	1995-02-24	Beecham Group Plc	Avermectins and milbemycins and compositions thereof
US5614470A (en) *	1994-04-01	1997-03-25	Sankyo Company, Limited	13-substituted milbemycin derivatives, their preparation and their use
GB0229804D0 (en) *	2002-12-20	2003-01-29	Syngenta Participations Ag	Avermection b1 and avermectin b1 monosaccharide derivatives having an alkoxymethyl substituent in the 4"- or 4'-position

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4579864A (en) *	1984-06-11	1986-04-01	Merck & Co., Inc.	Avermectin and milbemycin 13-keto, 13-imino and 13-amino derivatives
HUT39739A (en) *	1984-12-04	1986-10-29	Ciba Geigy Ag	Process for production of derivatives of 13,3-milbemycin and medical preparatives containing thereof
US4587247A (en) *	1985-02-25	1986-05-06	Merck & Co., Inc.	Substituted and unsubstituted 13-(alkoxy)methoxy derivatives of the avermectin aglycones, compositions and use
ES8802229A1 (es) *	1985-04-30	1988-04-16	Glaxo Group Ltd	Un procedimiento para preparar nuevos derivados lactonicos macrociclicos.
BR8701119A (pt) *	1986-03-12	1988-01-05	Glaxo Group Ltd	Processo para a preparacao de compostos,composicao para o controle de pragas e processo para combater pragas na agricultura
ATE109783T1 (de) *	1986-09-12	1994-08-15	American Cyanamid Co	23-oxo(keto) und 23-imino-derivate von ll-f28249- verbindungen.
US4806527A (en) *	1987-03-16	1989-02-21	Merck & Co., Inc.	Avermectin derivatives

1988
- 1988-05-10 GB GB888811037A patent/GB8811037D0/en active Pending
1989
- 1989-05-09 AT AT89304671T patent/ATE142211T1/de not_active IP Right Cessation
- 1989-05-09 JP JP1114338A patent/JP2506189B2/ja not_active Expired - Fee Related
- 1989-05-09 DK DK227389A patent/DK171025B1/da not_active IP Right Cessation
- 1989-05-09 HU HU892275A patent/HU204833B/hu not_active IP Right Cessation
- 1989-05-09 CA CA000599085A patent/CA1333599C/fr not_active Expired - Fee Related
- 1989-05-09 PT PT90508A patent/PT90508B/pt not_active IP Right Cessation
- 1989-05-09 BR BR898902169A patent/BR8902169A/pt not_active IP Right Cessation
- 1989-05-09 EP EP89304671A patent/EP0341972B1/fr not_active Expired - Lifetime
- 1989-05-09 DD DD89328420A patent/DD289531A5/de unknown
- 1989-05-09 AU AU34572/89A patent/AU631792B2/en not_active Ceased
- 1989-05-09 DE DE68927070T patent/DE68927070T2/de not_active Expired - Fee Related
- 1989-05-09 KR KR1019890006182A patent/KR960013441B1/ko not_active Expired - Fee Related
- 1989-05-09 NZ NZ229051A patent/NZ229051A/en unknown
- 1989-05-09 ZA ZA893428A patent/ZA893428B/xx unknown
- 1989-05-09 ES ES89304671T patent/ES2091761T3/es not_active Expired - Lifetime
1991
- 1991-04-30 US US07/693,029 patent/US5112854A/en not_active Expired - Lifetime
1996
- 1996-10-16 GR GR960402748T patent/GR3021375T3/el unknown

Also Published As

Publication number	Publication date
DE68927070D1 (de)	1996-10-10
JPH0262882A (ja)	1990-03-02
EP0341972A3 (fr)	1991-01-30
EP0341972A2 (fr)	1989-11-15
ATE142211T1 (de)	1996-09-15
HUT54373A (en)	1991-02-28
JP2506189B2 (ja)	1996-06-12
ES2091761T3 (es)	1996-11-16
BR8902169A (pt)	1990-01-02
DK227389A (da)	1989-11-11
DD289531A5 (de)	1991-05-02
DE68927070T2 (de)	1997-03-06
GB8811037D0 (en)	1988-06-15
GR3021375T3 (en)	1997-01-31
CA1333599C (fr)	1994-12-20
DK227389D0 (da)	1989-05-09
AU3457289A (en)	1989-11-16
KR960013441B1 (ko)	1996-10-05
KR890017251A (ko)	1989-12-15
NZ229051A (en)	1991-07-26
ZA893428B (en)	1990-03-28
PT90508A (pt)	1989-11-30
HU204833B (en)	1992-02-28
PT90508B (pt)	1994-08-31
US5112854A (en)	1992-05-12
AU631792B2 (en)	1992-12-10
EP0341972B1 (fr)	1996-09-04

Legal Events

Date	Code	Title	Description
1996-04-22	B1	Patent granted (law 1993)
2004-02-02	PBP	Patent lapsed	Country of ref document: DK

Publication	Publication Date	Title
DE3787548T2 (de)	1994-03-31	Makrolid-Verbindungen.
PT85018B (pt)	1990-03-08	Processo para a preparacao de compostos macrolidos e de composicoes farmaceuticas que os contem
US4916153A (en)	1990-04-10	Macrolid compounds
EP0238258B1 (fr)	1994-01-26	Composés de macrolides
EP0241146B1 (fr)	1993-02-03	Composés de macrolides
DK170344B1 (da)	1995-08-07	Makrolidforbindelser, farmaceutiske, veterinære og ikke-terapeutisk pesticide præparater indeholdende forbindelser, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
DK170859B1 (da)	1996-02-12	Makrolidforbindelser, præparater indeholdende forbindelserne til anvendelse i human medicin og veterinær medicin og til bekæmpelse af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
DK171025B1 (da)	1996-04-22	Makrolidforbindelser, farmaceutiske, veterinære og ikke-farmaceutiske pesticide præparater indeholdende forbindelserne, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige mider og fremgangsmåde til fremstilling af forbindelserne samt forbindelser til anvendelse ved fremstilling af makrolidforbindelserne
US4918096A (en)	1990-04-17	Antibiotic compounds and method of use
US4996228A (en)	1991-02-26	Macrolide antibiotics
DK171063B1 (da)	1996-05-13	Makrolidforbindelser, præparater indeholdende makrolidforbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr, fremgangsmåde til fremstilling af forbindelserne samt fremgangsmåde til fremstilling af mellemprodukter
AU621061B2 (en)	1992-03-05	Macrolide compounds
US5336789A (en)	1994-08-09	Macrolide compounds
DK171255B1 (da)	1996-08-12	Makrolidforbindelser, præparater indeholdende forbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
US5192777A (en)	1993-03-09	Macrolide compounds
US5185456A (en)	1993-02-09	Macrolide compounds
RU2099334C1 (ru)	1997-12-20	Макролидные соединения, композиция, обладающая антибиотической активностью, ветеринарная композиция, инсектоакарицидонематоцидная композиция и способ уничтожения насекомых и/или клещей, нематод
DE3781563T2 (de)	1993-01-07	Makrolid-antibiotika und verfahren zu ihrer herstellung.