Abstract: The present invention relates to novel 5-acyl, 23-acyl and 5,23-diacyl derivtaives of the LL-F28249 compounds. These LL-F28249 compounds (collectively) are isolates from the fermentation broth of Streptomyces cyaneogriseus subspecies noncyanogenus having deposit accession number NRRL 15773. The present 5-acyl and 5,23-diacyl compounds are prepared by selective acylation using acid chlorides or anhydrides in the presence of 4-dimethylaminopyridine. The 23-acyl compounds are prepared by selective acylation of the 5-O-silylated LL-F28249 compounds. These novel compounds have potent anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these derivatives of LL-F28249 also are described herein.

Abstract: The present invention relates to novel derivatives of LL-F28249 compounds wherein the 23-hydroxy group is eliminated to introduce a double bond at the 23,24 position. These resulting derivatives are .DELTA..sup.23 -LL-F28249 compounds. These LL-F28249 precursor compounds preferably are derived via a controlled microbiological fermentation of Streptomyces cyaneogriseus subsp. noncyanogenus having deposit accession number NRRL 15773. The novel derivatives of the present invention possess activity as anthelmintic, ectoparasitic, insecticidal, acaricidal and nematicidal agents. They also are useful in areas of human and animal health and in agricultural crops.

Abstract: The present invention relates to novel derivatives of LL-F28249 compounds. These LL-F28249 compounds preferably are derived via a controlled microbiological fermentation of Streptomyces cyaneogriseus subspecies noncyanogenus having deposit accession number NRRL 15773. The 23-deoxy-27-halo(chloro) derivatives have the 23-hydroxy group of the LL-F28249 compounds replaced by hydrogen and a halogen such as chlorine in the 27-position with the double bond shifted to the 26,26'-position. The novel derivatives of the present invention possess activity as anthelmintic, ectoparasitic, insecticidal, acaricidal and nematicidal agents and are useful in areas of human and animal health and in agricultural crops. Compositions containing the present compounds also are presented herein.

Abstract: The present invention relates to novel 23-imino derivatives of LL-F28249.alpha., .beta., .gamma., .delta., .epsilon., .zeta., .theta., .iota., and .lambda. compounds. These LL-F28249 compounds (collectively) are isolates from the fermentation broth of Streptomyces cyaneogrisesu subspecies noncyanogenus having deposit accession number NRRL 15773. The precursor 23-oxo compounds are prepared by selectively oxidizing suitably protected 23-hydroxy compounds of LL-F28249 components using oxidizing agents. Subsequently, the 23-oxo compounds are converted to the 23-imino compounds. These novel compounds have potent anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these 23-oxo and 23-imino derivatives of LL-F28249 also are described herein.

Abstract: The present invention relates to novel derivatives of LL-F28249 compounds. These LL-F28249 compounds preferably are derived via a controlled microbiological fermentation of Streptomyces cyaneogriseus subsp. non-cyanogenus having deposit accession numer NRRL 15773. The derivatives of the present invention have the 23-hydroxy group react to form a double bond in the 22,23 position. The novel derivatives of the present invention possess activity as anthelmintic, ectoparasitic, insecticidal, acaricidal and nematicidal agents. They also are useful in areas of human and animal health and in agricultural crops.

Abstract: The present invention relates to novel derivatives of LL-F28249 compounds wherein the 23-hydroxyl group is replaced with hydrogen and the double bond at the C(26,27)-position is epoxidized concomitant with or without epoxidation of the double bond at the C(14,15)-position. The LL-F28249 compounds (collectively) are isolates from the fermentation broth of Streptomyces cyaneogriseus subspecies noncyanogenus having deposit accession number NRRL 15773. The compounds of the present invention are derived by regioselective epoxidation of 5,23-O,O-bissilylated LL-F28249 compounds at low temperature, desilylation, re-silylation of the 5-hydroxyl group, thiocarbonylation of the 23-hydroxyl group, disilyation followed by tributyltin hydride reduction. The novel deoxy compounds of the present invention have anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these described derivatives as active ingredients thereof are described herein.

Abstract: The present invention relates to novel 23-oxo (keto) and 23-imino derivatives of certain C(26,27)-epoxy- and C(14,15;26,27)-diepoxy-LL-F28249 compounds. The LL-F28249 compounds (collectively) are isolates from the fermentation broth of Streptomyces cyaneogriseus subspecies noncyanogenus having deposit accession no. NRRL-15773. The derivatives are obtained by oxidation of the 23-hydroxy group of 5-O-silylated-C(26,27)-epoxy and C(14,15;26,27)diepoxy-LL-F28249 compounds, followed by desilylation and derivatization with amino compounds. The novel compounds have anthelmintic, ectoparasiticidal, nematicidal, insecticidal and acaricidal activity and are, therefore, useful in the treatment of infections in warm-blooded animals and infestations in agricultural crops. Compositions containing the present compounds as active ingredients thereof also are presented.

Abstract: The present invention relates to novel 23-imino derivatives of the compounds collectively referred to as 23-keto C-076 compounds. The C-076 compounds (collectively) are isolates from the fermentation broth of Streptomyces avermitilis. These novel compounds have potent anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these 23-imino derivatives of 23-keto C-076 also are described herein.

Abstract: The present invention relates to novel 23-imino derivatives of C-076 wherein the C-076 compounds are not substituted at the 13-position. The C-076 compounds (collectively) are isolates from the fermentation broth of Streptomyces avermitilis. The precursor 23-oxo compounds are prepared by selectively oxidizing suitably protected 13-deoxy C-076 aglycone compounds by using oxidizing agents. Subsequently, the 23-oxo compounds are converted to the 23-imino compounds. These novel compounds have potent anthelmintic, insecticidal, ectoparasticidal, nematicidal and acaricidal activity. Compositions containing these 23-oxo and 23-imino derivatives of 13-deoxy C-076 aglycones also are described herein.

Abstract: The present invention relates to novel mono- C(26,27) and diepoxide C(14,15;26,27) derivatives of LL-F28249.alpha., .beta., .epsilon., .zeta., .theta. and .iota. compounds. The LL-F28249 compounds (collectively) are isolates from the fermentation broth of Streptomyces cyaneogriseus subspecies noncyanogenus having deposit accession number NRRL-15773. The compounds of this present invention are derived by regioselective epoxidation of 5,23-0,0-bis-silylated LL-F28249 compounds at low temperature, followed by desilylation. These novel compounds have anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity and also are useful intermediates for the preparation of further biologically active compounds. Compositions containing these described derivatives as active ingredients thereof are described.

Abstract: There are provided novel anthranilonitrile derivatives and related compounds which are useful for promoting growth, improving feed efficiency and for increasing the lean meat to fat ratio of warm-blooded animals.

Abstract: The present invention relates to novel derivatives of LL-F28249 compounds wherein the pendent C(26,27) olefinic group at C(25) is converted into a 27-bromo or 27-chloro-26-methylene group. The 27-bromo compounds are derived by reacting the LL-F28249 compounds or 5-0-trisubstituted silyl LL-F28249 compounds with N-bromoacetamide or N-bromosuccinimide in aqueous acetone, followed by desilylation for silylated LL-F28249 intermediates. The 27-chloro compounds are prepared by reacting LL-F28249 compounds with N-chlorosuccinimide in methanol. These novel halo compounds have anthelmintic, ectoparasitic, insecticidal, nematicidal and acaricidal activity and are also useful intermediates for the preparation of other novel biologically active compounds. Compositions containing the present compounds as active ingredients thereof are presented.

Abstract: The present invention relates to novel derivatives of LL-F28249 compounds wherein the 23-hydroxyl group is eliminated to form a double bond at the C(22,23)-position (.DELTA..sup.22), and the double bond at the C(26,27)-position is epoxidized concomitant with or without epoxidation of the double bond at the C(14,15)-position. These LL-F28249 compounds (collectively) are isolates from the fermentation broth of Streptomyces cyaneogriseus subspecies noncyanogenus having deposit accession number NRRL 15773. The compounds of the present invention are derived by regioselective epoxidation of 5,23-O,O-bissilylated LL-F28249 compounds at low temperature, desilylation, re-silylation of the 5-hydroxyl group, thiocarbonylation of the 23-hydroxyl group, desilylation and thermalization. The novel compounds of the invention have anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these described derivatives as active ingredients thereof are described herein.

Abstract: The present invention relates to novel 23-imino derivatives of the compounds collectively referred to as 23-keto C-076 compounds. The C-076 compounds (collectively) are isolates from the fermentation broth of Streptomyces avermitilis. These novel compounds have potent anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these 23-imino derivatives of 23-keto C-076 also are described herein.

Abstract: Novel acid addition salts of 1-(aminodihalophenyl)-2-aminoethanols and method of preparation thereof. The invention describes certain non-dusting, antilipogenic compositions used as animal feed supplements and/or concentrates and a method for increasing weight gain and improving the lean meat to fat ratio of warm-blooded animals.

Abstract: A method for increasing the growth rate and/or improving the lean meat to fat ratio in farm and domestic animals. An effective amount of a 3-amino-4-hydroxy(or alkoxy)phenethanolamine derivative, pharmacologically-acceptable acid addition or metal salt thereof is administered either orally or parenterally to animals. Novel 3-amino-4-hydroxy(or alkoxy)phenethanolamine derivatives are also described.

Abstract: There are provided novel 5-fluorobenzonitrile derivatives which exhibit low .beta..sub.1 heart stimulant activity and are useful for increasing the lean meat to fat ratio and/or enhancing the growth rate of warm-blooded animals by, orally or parenterally, administering to said animals an amount of a 5-fluorobenzonitrile derivative or a pharmacologically acceptable salt thereof effective for achieving one or more of the above-identified metabolic improvements in said warm-blooded animals.

Abstract: Novel acid addition salts of 1-(aminodihalophenyl)-2-aminoethanols and method of preparation thereof. The invention describes certain non-dusting, antilipogenic compositions used as animal feed supplements and/or concentrates and a method for increasing weight gain and improving the lean meat to fat ratio of warm-blooded animals.

Abstract: A method for increasing the growth rate and/or improving the lean meat to fat ratio in farm and domestic animals. An effective amount of a 3-amino-4-hydroxy(or alkoxy)phenethanolamine derivative, pharmacologically-acceptable acid addition or metal salt thereof is administered either orally or parenterally to animals. Novel 3-amino-4-hydroxy(or alkoxy)phenethanolamine derivatives are also described.

Abstract: A method for increasing the growth rate and/or improving the lean meat to fat ratio in farm and domestic animals. An effective amount of an alkanesulfonanilide derivative, pharmaceutically acceptable acid addition or metal salt thereof is administered either orally or parenterally to animals. Novel 2'hydroxy-5'-[1-alkoxy-2-(alkyl-, dialkyl- or aralkylamino)ethyl]-alkanesulfonanilides are described.