WO1989003181A1 - Composition a base de derives de phenylpyridazinone pour assurer la croissance tout en diminuant les graisses chez les animaux - Google Patents

Composition a base de derives de phenylpyridazinone pour assurer la croissance tout en diminuant les graisses chez les animaux Download PDF

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Publication number
WO1989003181A1
WO1989003181A1 PCT/EP1988/000905 EP8800905W WO8903181A1 WO 1989003181 A1 WO1989003181 A1 WO 1989003181A1 EP 8800905 W EP8800905 W EP 8800905W WO 8903181 A1 WO8903181 A1 WO 8903181A1
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WIPO (PCT)
Prior art keywords
group
alkyl
substituted
phenyl
hydrogen atom
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PCT/EP1988/000905
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German (de)
English (en)
Inventor
Klaus Euler
Peter Lechtken
Walter Kohler
Peter Paul Hoppe
Franz-Josef Schoener
Karl-Heinz Geiss
Marco Thyes
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Basf Aktiengesellschaft
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Publication of WO1989003181A1 publication Critical patent/WO1989003181A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen

Definitions

  • the invention relates to agents based on phenylpyridazinone derivatives and their use for promoting growth, increasing feed utilization and the amount of protein and for reducing fat in animals, in particular farm and domestic animals.
  • feed additives to achieve higher weight additions, improved feed utilization and reduced fat intake is already widely practiced in animal nutrition, especially when fattening pigs, cattle and poultry.
  • a and B either each represent a hydrogen atom or together form a bond
  • D is oxygen or sulfur
  • E is a phenyl, benzyl, pyridyl, C 1 -C 4 -alkyl group or together with R 1 the group - (CH 2 ) K NH- where K represents the number 2 or 3
  • a C 1 -C 6 alkyl group which is substituted by 1 to 3 fluorine, chlorine or bromine atoms, a hydroxy, a C 1 -C 3 alkoxy, a C 2 -C 4 alkanoyloxy, a C 1 -C 3 alkylsulfonyloxy, an aminocarbonyloxy, a mono- or di (C 1 -C 3 alkyl) aminocarbonyloxy, a mercapto, a C 1 -C 3 alkylmercapto, a phenylmercapto, a pyridylmercapto -, Pyridazinylmercapto, pyrimidinylmercapto, pyrazinylmercapto or a triazinyl mercapto group, a cyano, a carboxy, a (C 1 -C 4 alkoxy) carbonyl group, a phenyl group, which is substituted by 1 to 2 C 1 -C
  • R 6 is a hydrogen atom, a C 1 -C 4 alkyl group which is optionally substituted by a phenyl radical, a C 3 -C 5 cycloalkyl group, a phenyl group which is optionally substituted by 1 or 2 C 1 -C 4 alkyl groups, 1 or 2 C 1 -C 4 alkoxy groups or 1 or 2 halogen atoms and / or can be substituted by a nitrile, nitro or trifluoromethyl group, or
  • R 8 is a group of the formula R 8 R 9 N-, in which R 8 is a hydrogen atom or a phenyl group which is 1 to 2 times halogen atoms, C 1 -C 4 -alkyl radicals, C 1 -C 4 -alkoxy groups and / or a nitrile and / or nitro group can be substituted, R 9 represents a C 1 -C 4 alkanoyl or benzoyl group or R 8 and R 9 together with the nitrogen atom form a benzimidazol-2-one-1-yl group, R 7 can have the same meanings as R 6 ,
  • R 10 is a C 1 -C 3 hydrocarbon radical which can be substituted by a naphthyl radical or a phenyl radical, the phenyl radical optionally having 1 to 2 halogen atoms, 1 to 2 C 1 -C 4 alkyl radicals, 1 to 2 C 1 -C 4 -alkoxy radicals or a trifluoromethyl, nitro, hydroxy, C 1 -C 4 -alkanoyl, (C 1 -C 5 -alkoxy) carbonyl and / or cyano group, a naphthyl radical, a phenyl radical which may contain 1- can be substituted up to 3 times by halogen atoms, C 1 -C 4 alkyl radicals, C 1 -C 4 alkoxy groups and / or a trifluoromethyl or a C 1 -C 4 alkanoyl group, or a 6-membered heteroaryl radical with 1 to 2 denotes nitrogen atoms and p represents the
  • R 11 is a hydrogen atom, a C 1 -C 8 alkyl radical, optionally by a phenyl radical, the 1 to 2 C 1 -C 4 alkyl groups, 1 to 2 C 1 -C 4 alkoxy groups and / or 1 or 2 halogen atoms may contain, is substituted, a C 3 -C 12 cycloalkyl group which can be substituted by 1 to 3 methyl groups, a phenyl or benzyl radical, or a C 7 -C 10 bi- or tricyclic alkyl radical which is substituted by 1 to 3 methyl radicals may be substituted, or a benzo-fused C 5 -C 7 cycloalkyl group and R 12 is a hydrogen atom or a
  • n denotes the number 1, 2 or 3 and the aromatic ring can be substituted by 1 to 2 halogen atoms, 1 to 2 C 1 -C 4 alkyl radicals or 1 to 2 C 1 -C 4 alkoxy radicals, or
  • c) denotes a C 2 -C 6 alkenyl group which can be substituted by 1 chlorine atom or a phenyl group, or
  • d) represents a C 3 -C 6 alkynyl group
  • e) represents a C 3 -C 6 cycloalkyl group which can be substituted by 1 to 2 C 1 -C 3 alkyl groups and / or 1 to 2 fluorine, chlorine or bromine atoms and / or by 1 phenyl group
  • - or f) represents a phenyl group which is represented by 1 to 2 C 1 -C 3 alkyl groups, 1 to 2 C 1 -C 3 alkoxy groups, 1 to 2 fluorine, chlorine or bromine atoms, an amino group, a mono- or di- C 1 -C 3 alkylamino group.
  • a C 2 -C 4 alkanoylamino group, a carboxy group or a C 1 -C 4 alkoxycarbonyl group may be substituted, or
  • g) represents a pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl group which is represented by 1 to 3 C 1 -C 3 -alkyl groups and / or a C 1 -C 3 -alkoxy group, a hydroxyl group, an amino group, a Mono or di-C 1 -C 3 alkylamine group may be substituted, or
  • h represents a 5-membered aromatic heterocyclic group which contains 1 oxygen, 1 sulfur and / or 1, 2 or 3 nitrogen atoms as heteroatoms and is optionally substituted by 1 to 3 C 1 -C 3 -alkyl groups, or
  • i) represents a C 1 -C 6 alkoxy group which has a C 3 -C 6 cycloalkyl group, one or two chlorine or bromine atoms, a C 1 -C 3 alkoxy group or a phenyl group - which has 1 to 2 C 1 -C 3 alkyl, 1 to 2 C 1 -C 3 alkoxy, 1 to 2 fluorine, chlorine or bromine atoms, a trifluoromethyl radical or a nitro group may be substituted, or
  • k represents a C 3 -C 6 alkynyloxy group which may be substituted by a phenyl radical, or
  • m represents a phenoxy group which can be substituted by 1 to 2 C 1 -C 3 -alkyl radicals, 1 to 2 C 1 -C 3 -alkoxy groups, 1 to 2 fluorine or chlorine atoms or a nitro group, or
  • n represents a C 1 -C 3 alkyl mercapto group
  • R 13 represents the group R 13 R 1 ⁇ N, where R 13 represents a hydrogen atom, a C 1 -C 3 alkyl, a C 3 -C 4 alkenyl or a C 3 -C 4 alkynyl group or a phenyl group and R 14 represents a hydrogen atom or a C 1 -C 3 alkyl group, or R 1 , if D represents a sulfur atom, denotes a C 1 -C 4 alkylamino group or a di (C 1 -C 4 alkyl) amino group, or
  • R 1 if D represents the group -N-CN, for a hydrogen atom, a C 1 -C 4 alkyl group, a phenyl group, a C 1 -C 4 alkylamino or a di (C 1 -C 4 alkyl) amino group stands, or
  • R 2 represents a hydrogen atom or a C 1-3 alkyl group
  • R 1 and R 2 together form a C 2 -C 4 alkylidene group which can be substituted by 1 to 2 C 1-3 alkyl groups and / or a phenyl group,
  • R 3 represents a hydrogen atom, chlorine atom, bromine atom or a nitrile group or
  • R 1 and R 3 together form a C 1 -C 3 alkylidene group which can be substituted by 1 to 2 C 1 -C 3 alkyl groups,
  • R 4 represents a hydrogen atom, a methyl or a hydroxymethyl group
  • R 5 represents a hydrogen atom or, if A and B represent hydrogen atoms, R 4 and R 5 together represent a C 1 -2 alkylidene group;
  • R 15 is a hydrogen atom, a C 1-4 alkyl radical, a phenyl, a hydroxy, a C 1-4 alkoxy or a phenoxy group, the group R 18 -NH-CH 2 -CH (OH) -CH 2 O-, in which R 18 isopropyl or tert.
  • -Butyl group means a nitro, trifluoromethyl, carboxy, C 1 -C 4 alkoxycarbonyl, aminocarbonyl or cyano group, a fluorine, chlorine or bromine atom, an amino, C 1-4 alkylamino or di (C 1 -C 4 alkyl) amino group, a pyrrolidine, piperidine or morpholine residue, or the group -NH-CH2-J, where J denotes a pyridyl, furyl, thienyl or phenyl residue, the phenyl residue being through 1 to 3 radicals from the group halogen, hydroxy, C 1 -C 4 alkoxy, nitro, amino, di (C 1 -C 4 alkyl) amino, (C 1 -C 4 alkoxy) carbonyl or C 1 -C 4 alkyl may be substituted, or a group -NHL, in which L is a 5- or 6-membered heterocyclic group, the 1 N, 0
  • heterocyclic group by a radical from the group cyano, hydroxy.
  • R 19 R 20 N Hydroxy group or the radical R 19 R 20 N can be substituted, where R 19 and R 20 independently of one another are hydrogen atoms, C 1 -C 4 -alkyl radicals, benzyl or phenethyl groups or the group R 19 R 20 N for a pyrrolidine, piperidine - or morpholine residue, can be substituted,
  • R 16 and R 17 independently of one another represent a hydrogen atom, a C 1 -C 4 alkyl, C 1 -C 4 alkoxy group, a nitrile group, a fluorine, chlorine or bromine atom or
  • R 16 and R17 together represent a methylenedioxy or ethylidendioxy group
  • X and Y independently of one another represent an N atom or a carbon atom which is substituted by a hydrogen atom or one of the radicals R 21 , R 22 or R 23 ,
  • R 21 is a hydrogen atom, a C 1 -C 4 -alkyl group, a C 1 -C 4 -hydroxyalkyl group, a C 1 -C 4 -alkanoyl-, a hydroxycarbonyl, a (C 1 -C 4 -alkoxy) carbonyl -, an aminocarbonyl, a cyano group or a group of the formula purple
  • R 24 is a C 1 -C 6 alkyl, a phenyl (C 1 -C 3 alkyl), a C 1 -C 4 alkanoyl, a benzoyl, a pyridinecarbonyl or a C 1 -C 4 -Alkylsulfonyl distr means
  • R 25 represents a hydrogen atom or a C 1 -C 6 alkyl group, or
  • R 24 and R 25 together with the N atom to which they are attached represent a pyrrolidine, piperidine or piperazine residue which can be substituted by a phenyl group and / or a hydroxy group,
  • R 26 represents a C 1 -C 4 alkylidene group
  • R 22 and R 23 independently of one another denote hydrogen atoms or C 1 -C 4 alkyl groups
  • R 4 , R 5 , A and B have the meanings given in formula I and the pyridazinone radical is fixed at the 5- or 6-position of the aromatic ring,
  • M represents oxygen, sulfur or the group NR 28 , where R 28 represents a hydrogen atom, a C 1 -C 4 alkyl group, a C 3 -C 6 cycloalkyl group or a phenyl (C 1 -C 3 alkyl) group , and
  • R 27 is a hydrogen atom, a trifluoromethyl, C 1 -C 11 alkyl, C 3 -C 7 cycloalkyl, hydroxy, mercapto, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio group, a Group of the formula -NHR 29 , in which R 29 denotes a hydrogen atom, a C 1 -C 4 alkyl, phenyl (C 1 -C 3 alkyl), styryl or phenyl group,
  • phenyl group by 1 to 3 radicals from the group fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, hydroxy, mercapto, C 1 -C 4 -Alkylmercapto and / or 1 to 3 di (C 1 -C 4 alkyl) amino may be substituted, or a 5- to 6-membered heterocyclic aromatic group with 1N, 0 or S atom and optionally 1 to
  • heterocyclic group being represented by 1 to
  • Preferred compounds for the agent according to the invention and the use according to the invention are phenylpyridazinone derivatives of the general formula I,
  • a and B either represent hydrogen atoms or together form a bond
  • R 1 a is a hydrogen atom
  • R 6 is a hydrogen atom, a methyl group, a phenyl group which may optionally be substituted by 1 or 2 methyl groups, methoxy groups or chlorine atoms, or a group of the formula R 8 R 9 N - in which R 8 represents a hydrogen atom or a phenyl group is R 9 is a propionyl or benzoyl group or in which R 8 and
  • R 9 together with the nitrogen atom form a benzimidazol-2-one-1-yl group
  • R 7 represents a hydrogen atom, a methyl, a hydroxy, an acetyl, an ethoxycarbonyl or a cyano group
  • n stands for 1, or a group of the formula Ib,
  • R 10 represents a benzyl, a naphthyl or a phenyl radical which can be substituted 1 to 3 times by chlorine atoms, methyl and / or methoxy groups, or a pyridyl radical, and
  • p represents the number 2
  • R 11 is a C 1 -C 3 alkyl radical, which may be replaced by a
  • Phenylrest is substituted, and R 12 represents a hydrogen atom or a methyl radical, or
  • n is the number 2
  • a C 3 -C 6 cycloalkyl group which may be substituted by 1 to 2 methyl groups and / or 1 to 2 chlorine atoms and / or a phenyl group
  • a phenyl group which can be substituted by 1 to 2 methyl groups, 1 to 2 methoxy groups, 1 to 2 chlorine atoms, a carboxy group or an ethoxycarbonyl group, or
  • a pyridyl group which can be substituted by 1 to 3 methyl groups, or
  • R 13 is R 14 N, where R 13 is a hydrogen atom, a methyl, an allyl or a propynyl group and R 14 is a hydrogen atom or a methyl group,
  • R 2 represents a hydrogen atom
  • R 1 and R2 together form a C 2 -C 4 alkylidene group which can be substituted by 1 to 2 methyl groups,
  • R 3 represents a hydrogen atom, bromine atom or nitrile group
  • R 1 and R 3 together form a C 1 -C 3 alkylidene group which can be substituted by 1 to 2 methyl groups,
  • R 4 represents a hydrogen atom or, if A and B represent hydrogen atoms, a methyl group, and
  • R 5 represents a hydrogen atom or, if A and B represent hydrogen atoms, R 4 and R 5 together represent a methylidene radical and / or a phenylpyridazinone of the general formula II,
  • a and B represent hydrogen atoms or together form a bond
  • R 4 represents a hydrogen atom or, if A and B represent hydrogen atoms, a methyl group
  • R 5 represents a hydrogen atom or, if A and B are hydrogen atoms
  • R 4 and R 5 together represent a methylidene radical
  • R 15 is a hydroxyl, a methoxy, a carboxy, a C 1 -C 4 alkoxycarbonyl or a cyano group, a chlorine atom, an amino, a C 1 -C 4 -
  • Alkylamino or a di (C 1 -C 4 alkyl) amino group the group -NH-CH 2 -J, where J represents a pyridyl, furyl, thienyl or phenyl radical, or the group -NHL, in which L represents a pyridyl or a thiazolyl radical, where the pyridyl and the thiazolyl radical can be substituted by 1 to 2 methyl groups, and
  • R 16 and R 17 each independently represent a hydrogen atom, a methoxy group, a nitrile group, a chlorine atom or a bromine atom,
  • a and B represent hydrogen atoms or together form a bond
  • R 4 represents a hydrogen atom or, if A and B represent hydrogen atoms, a methyl group
  • R 5 represents a hydrogen atom or, if A and B represent hydrogen atoms, together with R 4 represents a methylidene group, and the rest
  • a 1,2,4-triazol-l-yl radical a pyrazol-1-yl radical or a pyrrol-1-yl radical which is represented by a hydroxymethyl group, a formyl group, an acetyl group, a group of the formula purple,
  • R 24 represents a C 1 -C 3 alkyl, a benzyl, a C 1 -C 4 alkanoyl or a benzoyl group
  • R 25 represents a hydrogen atom or a C 1-6 alkyl group
  • A, 8 and R 5 are hydrogen atoms, R 4 is a methyl group, the pyridazinone radical is fixed at the 5- or 6-position of the phenyl ring news,
  • M represents the group NR 28 , wherein R 28 represents a hydrogen atom, a methyl or a benzyl group, and
  • R 27 represents a phenyl group which can be substituted by 1 to 2 methoxy groups
  • Phenylpyridazinones of the general formulas I, II, III and IV, in which A, B and R 5 represent a hydrogen atom and R 4 represents a methyl group are particularly preferred.
  • Particularly preferred radicals R 1 in general formula I are the radicals mentioned in sections a), b), f), g), h), i) and o).
  • R 1 and R 3 together form a C 2 -C 3 alkylidene radical which can be substituted by 1 to 2 methyl groups.
  • R 1 in formula I is an optionally substituted C 1 -C 3 alkyl group
  • a particularly suitable substituent is a chlorine atom, a hydroxy group, a methoxy group, a cyano group or a group of the formula Ia, Ib or Id.
  • EP-A-84 250 o) EP-A-85 985 p) JA-A-57 046 966 r) EP-A-145 019 s) AU-A-86 54 286 t) EP-A-197 664 u) BE-A-830 030
  • the active ingredients can be used in all areas of animal breeding as a means of promoting and accelerating growth, improving feed conversion, reducing the amount of fat and increasing the amount of protein in healthy and sick animals.
  • the effectiveness of the active ingredients is largely independent of the type and gender of the animals.
  • the active ingredients are particularly valuable in the rearing and keeping of young and fattening animals.
  • Examples of animals in which the active ingredients can be used to promote and accelerate growth and to improve feed conversion include the following useful and ornamental animals:
  • Warm-blooded animals such as cattle, pigs, horses, sheep, goats, cats, dogs, rabbits, fur animals, e.g. Mink and chinchilla, poultry e.g. Chickens, geese. Ducks, turkeys, pigeons, parrots and canaries and cold-blooded animals such as fish, e.g. Carp, trout and reptiles, e.g. Snakes.
  • the dose of active substance which is administered to the animals in order to achieve the desired effect can be varied largely because of the favorable properties of the active substances. It is preferably about 0.01 to 100, in particular 0.1 to 10 mg / kg of feed.
  • the duration of administration can range from a few hours or days to several years. The appropriate amount of the active ingredient and the appropriate duration of administration depend in particular on the type, age, gender, state of health and the type of keeping and feeding the animals and are easy to determine by any person skilled in the art.
  • the active substances are administered to the animals according to the usual methods.
  • the method of administration depends in particular on the type, behavior and state of health of the animals. So the administration can be administered orally once or several times a day at regular or irregular intervals or parenterally.
  • oral administration is preferred in most cases, particularly in the rhythm of the animals' food and / or drink intake.
  • the active ingredients can be used as a pure mixture or in formulated form, i.e. in a mixture with non-toxic inert carriers of any kind, e.g. with carriers and in formulations as are customary in nutritional preparations.
  • the active ingredients are optionally administered in a formulated form together with pharmaceutical active ingredients, mineral salts, trace elements, vitamins, protein substances, fats, colorings and / or flavorings in a suitable form.
  • Oral administration together with the feed and / or drinking water is recommended, the active ingredient being added to the total amount or only parts of the feed and / or drinking water as required.
  • the active substances are added to the feed and / or drinking water by simple mixing as a pure substance mixture, preferably in finely divided form or in formulated form in a mixture with edible non-toxic carrier substances, optionally in the form of a premix or a feed concentrate.
  • the feed and / or drinking water can, for example, contain the active substances in a weight concentration of approximately 0.01 to 100, in particular 0.1 to 10 ppm.
  • the optimum level of the concentration of the active substances in the feed and / or drinking water depends in particular on the amount of feed and / or drinking water intake by the animals and can be easily determined by any person skilled in the art.
  • feed and its composition are irrelevant. All common or special feed compositions can be used, which preferably contain the usual balance of energy and building materials including vitamins and minerals necessary for a balanced diet.
  • the feed can be composed, for example, of vegetable substances, for example hay, beets, cereals, grain by-products, animal substances, for example meat, fats, bone meal, fish products, vitamins, for example vitamin A, D complex and B complex, proteins, amino acids, for example DL-methionine and inorganic substances such as lime and table salt.
  • Feed concentrates contain the active ingredients in addition to edible substances, such as rye flour, corn flour, soybean meal or lime, optionally with other nutrients and builders as well as proteins, mineral salts and vitamins. They can be produced using the usual mixing methods.
  • the active ingredients can optionally also be covered by suitable agents covering their surface, e.g. protected from air, light and / or moisture with non-toxic waxes or gelatin.
  • Cefkaphos 1.76 1.76 carbon. Feed lime 1.2 1.20 Livestock salt 0.25 0.25
  • the specified feed mixtures are preferably matched for rearing and fattening chicks or pigs, but they can also be used in the same or a similar composition for rearing and fattening other animals, such as sheep and cattle.
  • test compounds as growth promoters and body fat reducing substances in animal nutrition - rat tests
  • the subsequent test period is 21 days.
  • the animals are fed ad libitum and / or rationed (1st week 90 g; 2nd week 110 g; 3rd week 130 g).
  • the animals are kept individually and weighed at weekly intervals.
  • the rats are killed with CO 2 .
  • the animals in a test group are autoclaved and then homogenized with a cutter.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Des compositions utiles pour assurer la croissance tout en diminuant les graisses chez les animaux, et pour améliorer l'assimilation du fourrage et la teneur en de protéines chez ces derniers, contiennent au moins un dérivé de phénylpyridazinone ou un de ses sels physiologiquement compatibles.
PCT/EP1988/000905 1987-10-17 1988-10-10 Composition a base de derives de phenylpyridazinone pour assurer la croissance tout en diminuant les graisses chez les animaux WO1989003181A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3735207.5 1987-10-17
DE19873735207 DE3735207A1 (de) 1987-10-17 1987-10-17 Mittel auf der basis von phenylpyridazinon-derivaten zur wachstumsfoerderung und fettreduktion bei tieren

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Publication Number Publication Date
WO1989003181A1 true WO1989003181A1 (fr) 1989-04-20

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PCT/EP1988/000905 WO1989003181A1 (fr) 1987-10-17 1988-10-10 Composition a base de derives de phenylpyridazinone pour assurer la croissance tout en diminuant les graisses chez les animaux

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EP (1) EP0401219A1 (fr)
DE (1) DE3735207A1 (fr)
WO (1) WO1989003181A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104478809A (zh) * 2014-11-14 2015-04-01 成都新恒创药业有限公司 一种左西孟旦杂质及其制备和检测方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0059688A1 (fr) * 1981-03-04 1982-09-08 Ciba-Geigy Ag Pyridazinones, leur procédé de préparation, compositions pharmaceutiques contenant ces composés et leur utilisation
EP0065192A1 (fr) * 1981-05-15 1982-11-24 BASF Aktiengesellschaft Fourrage ou liquide d'abreuvoir favorisant la croissance
EP0117403A1 (fr) * 1983-01-22 1984-09-05 BASF Aktiengesellschaft Dérivés de 6-(Acylaminoaryl)-3(2H)-pyridazinones, leur préparation et utilisation
US4545810A (en) * 1980-08-07 1985-10-08 Sds Biotech Corporation Herbicidal and plant growth regulant diphenylpyridazinones
EP0167995A2 (fr) * 1984-07-12 1986-01-15 BASF Aktiengesellschaft (Pyrrol-1-yl)-phényl-dihydropyridazinones, leur préparation et utilisation
EP0196005A1 (fr) * 1985-03-27 1986-10-01 Dr. Karl Thomae GmbH Pyridazinones, leur préparation et compositions les contenant
EP0199465A2 (fr) * 1985-03-27 1986-10-29 Smith Kline & French Laboratories Limited Composés dérivés de cyanoalcanimide amide

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4545810A (en) * 1980-08-07 1985-10-08 Sds Biotech Corporation Herbicidal and plant growth regulant diphenylpyridazinones
EP0059688A1 (fr) * 1981-03-04 1982-09-08 Ciba-Geigy Ag Pyridazinones, leur procédé de préparation, compositions pharmaceutiques contenant ces composés et leur utilisation
EP0065192A1 (fr) * 1981-05-15 1982-11-24 BASF Aktiengesellschaft Fourrage ou liquide d'abreuvoir favorisant la croissance
EP0117403A1 (fr) * 1983-01-22 1984-09-05 BASF Aktiengesellschaft Dérivés de 6-(Acylaminoaryl)-3(2H)-pyridazinones, leur préparation et utilisation
EP0167995A2 (fr) * 1984-07-12 1986-01-15 BASF Aktiengesellschaft (Pyrrol-1-yl)-phényl-dihydropyridazinones, leur préparation et utilisation
EP0196005A1 (fr) * 1985-03-27 1986-10-01 Dr. Karl Thomae GmbH Pyridazinones, leur préparation et compositions les contenant
EP0199465A2 (fr) * 1985-03-27 1986-10-29 Smith Kline & French Laboratories Limited Composés dérivés de cyanoalcanimide amide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104478809A (zh) * 2014-11-14 2015-04-01 成都新恒创药业有限公司 一种左西孟旦杂质及其制备和检测方法

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DE3735207A1 (de) 1989-04-27

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