WO2020133021A1 - Forme cristalline d d'un sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation - Google Patents

Forme cristalline d d'un sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation Download PDF

Info

Publication number
WO2020133021A1
WO2020133021A1 PCT/CN2018/124129 CN2018124129W WO2020133021A1 WO 2020133021 A1 WO2020133021 A1 WO 2020133021A1 CN 2018124129 W CN2018124129 W CN 2018124129W WO 2020133021 A1 WO2020133021 A1 WO 2020133021A1
Authority
WO
WIPO (PCT)
Prior art keywords
ciprofloxacin
dimethylamine salt
methyl
salt
ether
Prior art date
Application number
PCT/CN2018/124129
Other languages
English (en)
Chinese (zh)
Inventor
连磊
赵德
彭学岗
金涛
Original Assignee
青岛清原化合物有限公司
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.)
Filing date
Publication date
Application filed by 青岛清原化合物有限公司 filed Critical 青岛清原化合物有限公司
Publication of WO2020133021A1 publication Critical patent/WO2020133021A1/fr

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C07C211/04—Mono-, di- or tri-methylamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the invention belongs to the technical field of herbicide crystallization technology, and particularly relates to a crystalline form D of ciprofloxacin dimethylamine salt and a preparation method and application thereof.
  • Ciprofloxacin (structural formula: ) Is a newly developed HPPD inhibitor herbicide for post-emergence stem and leaf treatment of wheat fields, which has excellent biological activity and can effectively control a variety of malignant grass weeds in wheat fields.
  • the compound patent has been authorized, authorization announcement number: CN 105218449 B.
  • Polymorphism refers to the phenomenon in which solid substances form solid states with different physical and chemical properties in two or more different spatial arrangements. Different crystal forms have different colors, melting points, dissolution, dissolution properties, chemical stability, reactivity, mechanical stability, etc. These physical and chemical properties or processability sometimes directly affect the safety and effective performance of drugs. Therefore, crystal form research and control has become an important research content in the process of drug development.
  • the present invention provides a new herbicide ciprofloxacin dimethylamine salt D crystal form and its preparation method and use.
  • the crystal form has good physical and chemical stability, high solubility and high biological activity, and can be used for controlling common weeds in crop fields.
  • the corresponding I/I 0 are 1.9, 4.5, 95.6, 4.8, 2.4, 10.3, 5.7, 5.4, 100.0, 6.7, 13.2, 11.2, 7.9, 4.5, 0.9, 25.8, 11.1, 12.3, 2.4, 2.8 , 1.2, 4.9, 5.3, 4.2, 5.5, 1.8, 1.6, 6.6, 1.0, 1.7, 1.1, 1.5, 1.1, 2.0.
  • its X-ray powder diffraction pattern is substantially as shown in FIG. 1.
  • the preparation method of the crystalline form D of ciprofloxacin dimethylamine salt includes the following steps:
  • ciprofloxacin dimethylamine salt is suspended in the following solvents: isopropanol, n-butanol, isobutanol, tert-butanol, sec-butanol, ethyl acetate, butyl acetate, isopropyl acetate , N-heptane, n-hexane, cyclohexane, acetone, methyl ethyl ketone, 4-methyl-2-pentanone, anhydrous ether, isopropyl ether, methyl tert-butyl ether, anisole, phenethyl ether, ethyl ether Glycol dimethyl ether, toluene, p-xylene, chlorobenzene, 1,4-dioxane, tetrahydrofuran or acetonitrile, shake in a shaker and centrifuge and filter, the resulting solid is dried at 80-100
  • a herbicidal compound composition comprising (i) the crystalline form of ciprofloxacin dimethylamine salt; preferably, it also includes (ii) one or more other active ingredients and/or safeners; Preferably, (iii) agrochemically acceptable formulation aids are also included.
  • the auxiliary agent is selected from one or more of solvents, solid diluents, emulsifiers, wetting agents, dispersants, antifreeze agents, defoamers and thickeners.
  • Selected solvents include but are not limited to polar solvents: water, N,N-dimethylamide, dimethyl sulfoxide, N-alkylpyrrolidone, methanol, ethanol, ethylene glycol, isopropanol, ethylene glycol Butyl ether, propylene glycol methyl ether, etc.; aromatic hydrocarbon solvent oil series: toluene, xylene, No. 100 solvent oil, No. 150 solvent oil, No. 180 solvent oil, No.
  • the selected solid diluent may be water-soluble or water-insoluble.
  • Water-soluble solid diluents include, but are not limited to: salts, such as alkali metal phosphates (sodium dihydrogen phosphate), alkaline earth metal phosphates, sodium, potassium, magnesium and zinc sulfates, sodium chloride and potassium chloride, sodium acetate , Sodium carbonate and sodium benzoate, as well as sugar and sugar derivatives, such as sorbitol, lactose, sucrose and mannitol, corn starch and the like.
  • non-water soluble solid diluents include, but are not limited to: clay, calcium carbonate, diatomaceous earth, white carbon, calcium silicate, bentonite, magnesium aluminum silicate, kaolin and the like.
  • Wetting agents include, but are not limited to: alkyl sulfosuccinates, laurates, alkyl sulfates, phosphates, ethoxylated fluorinated alcohols, ethoxylated silicones, alkylphenol ethoxylates , Benzene sulfonate, alkyl substituted benzene sulfonate, alkyl ⁇ -olefin sulfonate, naphthalene sulfonate, alkyl substituted naphthalene sulfonate alkali metal salt, naphthalene sulfonate alkali metal salt and alkyl substitution Condensate of naphthalene sulfonate and formaldehyde, alcohol ethoxylate.
  • Dispersants include, but are not limited to: sodium, calcium and ammonium salts of lignin sulfonic acid; sodium and ammonium salts of maleic anhydride copolymer; sodium salts of condensed phenolsulfonic acid; naphthalenesulfonate-formaldehyde condensate ; Phosphate ester dispersant, polycarboxylate dispersant, etc.
  • Thickeners include, but are not limited to: guar gum, pectin, xanthan gum, alginate, methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, magnesium aluminum silicate, and the like.
  • Synthetic thickeners include derivatives of the foregoing types, and also include polyvinyl alcohol, polyacrylamide, polyvinylpyrrolidone, various polyethers and their copolymers, and polyacrylic acid and their salts.
  • formulation ingredients such as dyes, defoamers, desiccants, etc. can be used in the present invention. These ingredients are well known to those skilled in the art.
  • Suitable effective ingredients that can be mixed with the crystalline form D of ciprofloxacin dimethylamine salt of the present invention are, for example, "World Pesticide New Variety Technology Encyclopedia", China Agricultural Science and Technology Press, 2010.9 and the documents cited here Known substances.
  • acetochlor butachlor, alachlor Amine, propachlor, metolachlor, mesochlor, alachlor, alachlor, alachlor, naproxen, R-levonapropion, dipropanil, benzene Alafenamide, difenacetamide, flufenacetamide, chlorfenapyr, flufenacetamide, bromobutyramide, dimethoxamide, high-efficiency dimethoxamide, ethoxybenzamide Amine, flufenazone, alafenamide, metazachlor, clomazone, high-efficiency dicofol, high-efficiency propylpropanil, dipropoxyfen, dimethoprim, butachlor, cyprofen Glufosinate, fluoxanilam, h
  • the other active ingredients include, but are not limited to: pyrachlor (CAS No.: 83164-33-4), isoxaflutole (CAS No.: 141112-29-0), cypromethrin (CAS No.: 105512-06-9), oxazolin (CAS No.: 243973-20-8), isoproturon (CAS No.: 34123-59-6), chlormeron (CAS No.: 15545-48-9 ), octanoyl bromoxynil (CAS number: 1689-99-2), azoxystrobin (CAS number: 21087-64-9), dapyridine (CAS number: 55512-33-9), azaprofen (CAS number: 129909-90-6), 2 methyl 4 chlorine (CAS number: 94-74-6), chlorofluoropyroxyacetic acid (CAS number: 69377-81-7), fluorochloropyridine ester (CAS number: 943831-98-9), dicamba (CAS number: 1918-00
  • salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group.
  • 2M 4 Chlorine derivatives include but are not limited to: 2M 4 Chlorine sodium salt, potassium salt, dimethyl ammonium salt, isopropylamine salt, etc., as well as 2M 4 Chlorine methyl ester, ethyl ester, isooctyl ester, ethyl sulfide Ester etc.
  • the salt of the compound is preferably in the form of a respective alkali metal salt, alkaline earth metal salt or ammonium salt, preferably in the form of a respective alkali metal salt, more preferably in the form of a respective sodium or potassium salt, Most preferred is the form of the respective sodium salt.
  • the total mass percentage of active ingredients in the composition accounts for 1-95% of the total.
  • the safener is preferably bisoxazolic acid (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), pyrazolinate (CAS: 135590-91-9), detoxified quinoline (CAS : 99607-70-2), gibberellic acid (CAS: 7-06-5), furilazole (CAS: 121776-33-8), one or more of metcamifen (CAS: 129531-12-0).
  • the dosage form of the composition is water suspension (SC), dispersible oil suspension (OD), emulsifiable concentrate (EC), microemulsion (ME), granule (GR), suspension emulsion (SE) or water dispersible granule (WDG).
  • SC water suspension
  • OD dispersible oil suspension
  • EC emulsifiable concentrate
  • ME microemulsion
  • GR granule
  • SE suspension emulsion
  • WDG water dispersible granule
  • the present invention also provides a method for controlling weeds in crops, which includes using a herbicidally effective amount of the crystalline form D of ciprofloxacin dimethylamine salt or the herbicidal compound composition on crops or Weed area.
  • the present invention also provides the use of the crystalline form D of ciprofloxacin dimethylamine salt or the herbicidal compound composition for controlling weeds; preferably, it is used to control impurities in useful crops Grass, the useful crops are genetically modified crops or crops processed by genome editing technology.
  • the crop is wheat
  • the weeds are gramineous weeds, such as maidenhair, Japanese maidenhair, etc.
  • the crystalline form D of ciprofloxacin dimethylamine salt of the present invention has been tested and has good physical and chemical stability, good water solubility, and the solubility in water is increased by nearly forty times compared to ciprofloxacin, compared to ciprofloxacin
  • the sodium salt of oxalone has increased nearly twenty times, and the crystalline form D or the compound composition with other active ingredients has a good control effect on wheat field grasses weeds, and the effect is significantly better than ciprofloxacin. And its sodium salt.
  • FIG. 1 is an XRPD pattern of the crystalline form D of flufenazone dimethylamine salt in Example 2 of the present invention.
  • Instrument model Bruker D8 advance, target: Cu K ⁇ (40kV, 40mA), sample to detector distance: 30cm, scanning range: 3°-45° (2 ⁇ value), scanning step: 0.05s.
  • Example 2 1 kg of cyclofluxon obtained in Example 1 was reacted with 0.25 kg of 40% aqueous solution of dimethylamine to obtain a large amount of solid crystals. The solid was filtered and dried at 45°C to obtain powder of ciprofenone dimethylamine salt.
  • the three powders of ciprofloxanone and its sodium salt obtained in Example 1 and the crystalline form of ciprofloxacin dimethylamine D obtained in Example 2 were measured by HPLC.
  • the content of ciprofloxan was 97.2%.
  • the content of fluroxypyr sodium salt is 98.0%, and the content of crystalline form of ciprofloxacin dimethylamine is 98.0%.
  • the three original drug powders are placed at 25 °C, 40 °C, 55 °C and 70 Place in the oven at °C for 2 months to conduct the heat storage experiment, and then test the purity.
  • Ciprofloxacin Ciprofloxan sodium salt Ciprofloxacin dimethylamine salt D crystal form 25°C 97.2% 98.0% 98.0% 40°C 96.6% 97.8% 97.9% 55°C 96.1% 97.3% 97.5% 70°C 95.5% 96.5% 97.2%
  • Example 2 The three powders of ciprofloxanone and its sodium salt obtained in Example 1 and the crystalline form D of ciprofloxacin dimethylamine salt obtained in Example 2 were dissolved in pure water and shaken at 25°C for 24 h , To make it fully dissolved, then centrifuged and filtered, the filtrate was passed through a 0.22 ⁇ m filter membrane, and the solubility in water was determined by HPLC. The results are shown in Table 2 below:
  • the ciprofloxone and its sodium salt obtained in Example 1 and the crystalline form D of ciprofloxone dimethylamine salt obtained in Example 2 were processed into the following formulations according to the same formula.
  • the specific formula is as follows, which is effective Component A represents the crystalline form D of ciprofloxan, ciprofloxacin sodium salt and ciprofloxacin dimethylamine salt.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une forme cristalline D d'un sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation. Le spectre de diffraction de rayons X sur poudre de la forme cristalline D du sel de cypyrafluone diméthylamine a des pics caractéristiques à un angle de diffraction 2θ de 6,5º, 8,7º, 9,2º, 10,3º, 12,6º, 13,1º, 14,7º, 15,4º, 16,4º, 17,0º, 18,3º, 18,6º, 19,9º, 20,4º, 21,2º, 22,3º, 22,8º, 23,2º, 24,9º, 25,4º, 26,1º, 27,0º, 28,5º, 29,5º, 30,6º, 31,8º, 32,7º, 33,2º, 34,6º, 35,0º, 36,4º, 37,3º, 38,3º et 41,0º, avec une plage d'erreurs 2θ de ± 0,2º. La forme cristalline D du sel de cypyrafluone diméthylamine a une bonne stabilité physico-chimique, une solubilité élevée et une bonne activité biologique, et peut être utilisée pour la prévention et l'élimination de mauvaises herbes.
PCT/CN2018/124129 2018-12-25 2018-12-27 Forme cristalline d d'un sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation WO2020133021A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201811594964.8 2018-12-25
CN201811594964.8A CN111362919B (zh) 2018-12-25 2018-12-25 环吡氟草酮二甲胺盐d晶型及其制备方法和用途

Publications (1)

Publication Number Publication Date
WO2020133021A1 true WO2020133021A1 (fr) 2020-07-02

Family

ID=71125805

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2018/124129 WO2020133021A1 (fr) 2018-12-25 2018-12-27 Forme cristalline d d'un sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation

Country Status (2)

Country Link
CN (1) CN111362919B (fr)
WO (1) WO2020133021A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109819988A (zh) * 2019-01-28 2019-05-31 南京农业大学 一种环吡氟草酮与绿麦隆治理抗性日本看麦娘组合物及其应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046530A1 (fr) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
CN105218449A (zh) * 2015-11-06 2016-01-06 青岛清原化合物有限公司 吡唑酮类化合物或其盐、制备方法、除草剂组合物及用途
CN107286095A (zh) * 2017-07-13 2017-10-24 青岛清原化合物有限公司 双唑草酮d晶型及其制备方法和用途
CN107629035A (zh) * 2017-10-24 2018-01-26 青岛清原化合物有限公司 一种吡唑酮类化合物或其盐、除草剂组合物及用途

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2688406T3 (pl) * 2011-03-25 2015-10-30 Bayer Ip Gmbh Zastosowanie N-(tetrazol-4-ilo)- lub N-(triazol-3-ilo)arylokarboksamidów lub ich soli do zwalczania niepożądanych roślin w obszarach transgenicznych roślin uprawnych tolerancyjnych na środki chwastobójcze będące inhibitorem HPPD
CN106070226A (zh) * 2016-06-07 2016-11-09 泰安市农业科学研究院 一种环吡氟草酮组合物及其用途
CN106472517B (zh) * 2016-09-30 2018-11-02 江苏清原农冠杂草防治有限公司 增效除草组合物及其应用
CN107810963A (zh) * 2017-11-09 2018-03-20 青岛清原化合物有限公司 一种含环吡氟草酮的除草组合物及其应用
CN113142217B (zh) * 2018-07-21 2022-04-22 青岛清原化合物有限公司 包含hppd抑制剂类除草剂的三元除草组合物及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046530A1 (fr) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
CN105218449A (zh) * 2015-11-06 2016-01-06 青岛清原化合物有限公司 吡唑酮类化合物或其盐、制备方法、除草剂组合物及用途
CN107286095A (zh) * 2017-07-13 2017-10-24 青岛清原化合物有限公司 双唑草酮d晶型及其制备方法和用途
CN107629035A (zh) * 2017-10-24 2018-01-26 青岛清原化合物有限公司 一种吡唑酮类化合物或其盐、除草剂组合物及用途

Also Published As

Publication number Publication date
CN111362919A (zh) 2020-07-03
CN111362919B (zh) 2021-03-12

Similar Documents

Publication Publication Date Title
WO2018192047A1 (fr) Triazolesulcotrione amorphe, son procédé de préparation, et son utilisation
WO2018192043A1 (fr) Forme cristalline b de triazolesulcotrione, procédé pour sa préparation et utilisation correspondante
WO2018201523A1 (fr) Oxacilline fluridone amorphe, son procédé de préparation et son utilisation
WO2018192046A1 (fr) Forme cristalline c de triazolesulcotrione, son procédé de préparation et son utilisation
WO2019080224A1 (fr) Composé de pyrazolone ou sel de celui-ci, composition herbicide et utilisation
WO2020108518A1 (fr) Formamides de n-(1,3,4-oxadiazole-2-yl)aryle ou leur sel, procédé de préparation correspondant, composition herbicide et utilisation associée
WO2018201524A1 (fr) Biscarfentrazone amorphe, son procédé de préparation et son utilisation
WO2019010718A1 (fr) Forme cristalline b de dicarfentrazone-éthyle, son procédé de préparation et son utilisation
WO2019010716A1 (fr) Forme cristalline d de dicarfentrazone-éthyl, procédé de préparation associé et utilisation correspondante
WO2021078174A1 (fr) Composé de formamide aryl contenant de l'oxyde de soufre chiral et sel de celui-ci, son procédé de préparation, composition herbicide et utilisation
WO2020133011A1 (fr) Sel du cypyrafluone monoisopropylamine amorphe, son procédé de préparation et son utilisation
WO2021083245A1 (fr) Composition herbicide comprenant un composé de n-(1,3,4-oxadiazole-2-yl)arylformamide et son utilisation
WO2020133021A1 (fr) Forme cristalline d d'un sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation
WO2019196731A1 (fr) Composé de pyrazolyl pyrazole de sulfonylurée substitué ou sel ou composition pesticide acceptable de celui-ci et utilisation associée
WO2020133019A1 (fr) Forme cristalline b d'un sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation
WO2020133022A1 (fr) Sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation
WO2020133020A1 (fr) Forme cristalline c d'un sel de cypyrafluone diméthylamine, son procédé de préparation et son utilisation
WO2020133012A1 (fr) Sel de cypyrafluone monoisopropylamine, son procédé de préparation et son utilisation
WO2020133018A1 (fr) Sel de ciclopirox fluridone diméthylamine amorphe, son procédé de préparation et son utilisation
WO2020133015A1 (fr) Forme cristalline d d'un sel de cypyrafluone monoisopropylamine, procédé de préparation correspondant et utilisation associée
WO2020133017A1 (fr) Forme cristalline f d'un sel de cypyrafluone monoisopropylamine, son procédé de préparation et son utilisation
WO2020133014A1 (fr) Forme cristalline c d'un sel de cypyrafluone monoisopropylamine, son procédé de préparation et son utilisation
WO2020133016A1 (fr) Forme cristalline e d'un sel de cypyrafluone monoisopropylamine, son procédé de préparation et son utilisation
WO2020133024A1 (fr) Sel de cypyrafluone triéthanolamine, son procédé de préparation et son utilisation
WO2020133023A1 (fr) Sel de triéthanolamine de cypyrafluone amorphe, son procédé de préparation et son utilisation

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18944531

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18944531

Country of ref document: EP

Kind code of ref document: A1