EP3322296A1 - Amides substitués d'acide phosphonique et d'acide oxotétrahydrochinolinylphosphique, ou leurs sels et leur utilisation pour accroître la tolérance au stress chez les végétaux - Google Patents

Amides substitués d'acide phosphonique et d'acide oxotétrahydrochinolinylphosphique, ou leurs sels et leur utilisation pour accroître la tolérance au stress chez les végétaux

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Publication number
EP3322296A1
EP3322296A1 EP16738159.9A EP16738159A EP3322296A1 EP 3322296 A1 EP3322296 A1 EP 3322296A1 EP 16738159 A EP16738159 A EP 16738159A EP 3322296 A1 EP3322296 A1 EP 3322296A1
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EP
European Patent Office
Prior art keywords
alkyl
aryl
alkoxy
cycloalkyl
heteroaryl
Prior art date
Legal status (The legal status 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 status listed.)
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Application number
EP16738159.9A
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German (de)
English (en)
Inventor
Hendrik Helmke
Jens Frackenpohl
Jana FRANKE
Guido Bojack
Jan Dittgen
Dirk Schmutzler
Udo Bickers
Fabien Poree
Franziska ROTH
Jean-Pierre Vors
Pierre Genix
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Bayer CropScience AG
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Bayer CropScience AG
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Publication date
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Publication of EP3322296A1 publication Critical patent/EP3322296A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

Definitions

  • the invention relates to substituted oxotetrahydroquinolinyl phosphinic acid and phosphonic acid amides or their salts for increasing the stress tolerance in plants to abiotic stress, and for increasing plant growth and / or increasing the plant yield.
  • Arylsulfonamides having alkylcarboxyl substituents as growth regulators, especially for limiting the growth length of rice and wheat plants with the aim of minimizing the weather-related kinking is described in DE2544859, while the fungicidal action of certain N-Cyanoalkylsulfonamide is described in EP176327. It is also known that substituted N-sulfonylaminoacetonitriles can be used to control parasites in warm-blooded animals (see WO2004 / 000798).
  • WO2013 / 148339 while in WO2014 / 201555 corresponding 1-aryl-N- (2-OXO-1-alkenyl-1,2,3,4-tetrahydroquinoline-6-yl) -nethanesulfonan-1-ene and 1-aryl-N- (2-oxo-1-alkynyl-1,2,3,4-tetrahydroquinoline 6-yl) naphthanesulfonanides.
  • WO2013 / 148339 and WO2014 / 201155 also describe the agonistic action of the substances in question on abscisic acid receptors. It is also known that substituted dihydrooxindolylsulfonamides can be used as active ingredients against abiotic plant stress (see WO2015 / 049351).
  • Tetrahydroquinolinyl moiety and its action to increase the tolerance of plants to abiotic stress are described in WO2015 / 155154. It is further known that certain especially substituted N- (2-oxo-1-alkyl-1,2,3,4-tetrahydroquinolin-6-yl) methanesulphonamides (cf WO2016022910) and especially substituted 6-sulphonylaminoquinolines (see WO2016022915 ) can be used as growth regulators and for germination inhibition.
  • the signal chain genes of the abiotic stress reaction include, among others. Transcription factors of classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106).
  • the response to salt stress involves phosphatases of the ATPK and MP2C types.
  • salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated. Involved here are e.g. sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol. Biol. 57: 463-499).
  • sucrose synthase and proline transporters Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol. Biol. 57: 463-499.
  • Late Embryogenesis Abundant Proteins which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 700: 291-296). These are chaperones, the vesicles, proteins and
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
  • naphthylsulfonamide (4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide) influences the germination of plant seeds in the same manner as abscisic acid (Park et al., Science 2009, 324, 1068-1071).
  • a naphthylsulfamidocarboxylic acid (N - [(4-bromo-1-naphthyl) sulfonyl] -5-methoxynorvaline) exhibits a mode of action in biochemical receptor assays that react with 4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide is comparable (Melcher et al., Nature Structural & Molecular Biology 2010, 17, 1, 102-1 108).
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
  • Xanthines for increasing the abiotic stress tolerance in plants has already been described (Bergmann et al., DD277832, Bergmann et al., DD277835).
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • the object of the present invention was to provide compounds which further increase the tolerance to abiotic stress in plants, cause a strengthening of plant growth and / or contribute to the increase of the plant yield.
  • tolerance to abiotic stress for example, tolerance to cold, heat, Drought stress (stress caused by drought and / or lack of water), salting and flooding understood.
  • Oxotetrahydroquinolinylphosphinic and -phosphonklareamide can be used to increase the stress tolerance in plants to abiotic stress and to increase plant growth and / or increase the plant yield.
  • R 1 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, halogen, cyano, (C 3 -C 10) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C -Cio) -cycloalkenyl, (C -Cio) -halocycloalkenyl, (C 1 -C 10) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 1 -C 8 ) -alkoxy-
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkylthio, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl (Ci -C 8) -alkyl, (C 3 -C 8) -cycloalkyl, nitro, amino, hydroxy, (C 1 -C 8) -alkylamino, bis - [(C 1 -C 8) -alkyl] -amino,
  • R 5 is (Ci-Cs) alkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) cycloalkyl (Ci-C8) alkyl, (Ci-C 8) - haloalkyl, ( C 3 -C 8) halocycloalkyl, (C 4 -C 8) -alkenyl -Cycloal, aryl, heteroaryl heterocyclyl, aryl- (Ci-C 8) alkyl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (C 1 -C 8 ) -alkyl.
  • R 6 represents hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, cyano (Ci-C 8) alkyl, (C 3 -C 8) - cycloalkyl, (Ci-C 8 ) alkyl, (Ci-C8) alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 8) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl (Ci-C8) alkylsulfonyl, (Ci-C 8) alkylcarbonyl, arylcarbonyl , heteroarylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, heterocyclylcarbonyl, (Ci-C8) alkoxycarbonyl, aryl (Ci-C8) - alkoxycarbonyl, (Ci
  • R 7 , R 8 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, cyano, nitro, hydroxyl, amino, hydrothio, (C 1 -C 8) -alkylamino, bis [(C 1 -C 8) -alkyl] -amino, (C 3 -C 8 ) -cycloalkylamino, aryl- (C 1 -C 8 ) -alkylamino, heteroaryl- (C 1 -C 8 ) -alkylamino, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci -C 8) -haloalkyl, hydroxy (Ci-C 8) alkyl, cyano (Ci-C 8) alkyl, nitro, (Ci-C 8) alkyl, aryl, heteroaryl, (C 3 -C 8)
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, cyano, (C 1 -C 8 ) -haloalkyl, cyano- (C 1 -C 8 ) -alkyl, aryl, heteroaryl, (C 3 - C 8) cycloalkyl, (C-C8) cycloalkenyl, heterocyclyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) -
  • R 9 and R 10 with the carbon atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
  • R 1 , R 9 and R 10 with the carbon atom to which they are attached, a fully saturated, optionally interrupted by heteroatoms and
  • R 1 1 is (Ci-Cs) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) - cycloalkyl, (Ci-C 8) alkyl, hydroxy, ( C 3 -C 8 ) -cycloalkyloxy, (C 1 -C 8 ) -alkoxy,
  • V, W independently of one another represent oxygen or sulfur
  • X, Y are each independently hydrogen, (Ci-C 8) alkyl, halogen, (C2-C8) - alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) haloalkyl, hydroxy- ( Ci-C 8) alkyl, cyano (Ci-C 8) alkyl, aryl, heteroaryl, (C 3 -C 8) cycloalkyl, (C-C8) cycloalkenyl,
  • the compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4 , H 8 PO 4 or HNO 3 , or organic acids, e.g.
  • a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4 , H 8 PO 4 or HNO 3 , or organic acids, e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Sulfonic acids certain sulfonic acid amides or carboxylic acids are present, internal salts can in turn form protonatable groups, such as amino groups.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and Potassium bicarbonate.
  • organic amines such as trialkylamines, morpholine, piperidine and pyridine
  • ammonium alkali or alkaline earth metal hydroxides
  • carbonates and bicarbonates in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and Potassium bicarbonate.
  • These salts are compounds in which the acidic
  • Hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • alkylsulfonium and Alkylsulfoxoniumsalze such as (Ci-C4) - trialkylsulfonium and (Ci-C 4) -Trialkylsulfoxoniumsalze.
  • R 1 is hydrogen, (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, halogen, cyano, (C 3 -C 10) -cycloalkyl, (C 3 -Cio) halocycloalkyl, (C -Cio) cycloalkenyl, (C -Cio) - Halocycloalkenyl, (Ci-Cio) -haloalkyl, (C 2 -C 7) haloalkenyl, (Ci-C7) alkoxy ( Ci-C7) haloalkyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C 7) alkyl, (C 2 -C 7) haloal
  • Heterocyclyl (C 1 -C 7) -alkylaminocarbonyl, (C 1 -C 7) -alkylsulfonyl, (C 3 -C 7) -cycloalkylsulfonyl, arylsulfonyl, aryl- (C 1 -C 7) -alkylsulfonyl, heteroarylsulfonyl, heterocyclylsulfonyl, cyano- (C 1 -C 7) - alkyl, (C 4 -C 7) -cycloalkenyl- (C 1 -C 7 ) -alkyl, nitro (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (Ci -C 7) -Haloalkylthio- (Ci-C7) alkyl, - bis [
  • R 2, R 3, R 4 are independently hydrogen, halogen, (Ci-C7) alkoxy, (Ci-C7) - Al kyl, (Ci-C7) haloalkyl, (Ci-C7) - Haloalkoxy, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 7 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, nitro, amino, hydroxy, (C 1 -C 7 ) -alkylamino, bis - [(C 1 -C 7 ) -alkyl] -amino, hydrothio, ( C 1 -C 4 ) -al
  • R 9 and R 10 with the carbon atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
  • R 9 and R 10 with the carbon atom to which they are attached, a fully saturated, optionally interrupted by heteroatoms and
  • R 7 and R 8 with the carbon atom to which they are attached form an oxo group or R 7 and R 8 with the carbon atom to which they are attached form a
  • R 1 1 is (Ci-C7) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7) cycloalkyl, (C 3 -C 7) - cycloalkyl- (Ci-C7) alkyl, hydroxy, (C 3 -C 7 ) -cycloalkyloxy, (C 1 -C 7 ) -alkoxy,
  • V, W independently of one another represent oxygen or sulfur
  • X, Y are each independently hydrogen, (Ci-C7) alkyl, halogen, (C2-C7) - alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, hydroxy- ( Ci-C7) alkyl, cyano (Ci-C7) alkyl, aryl, heteroaryl, (C 3 -C 7) cycloalkyl, (C-C7) cycloalkenyl,
  • Heteroaryloxycarbonylamino- (Ci-C7) -alkyl Heterocyclyloxycarbonylamino- (Ci-C7) -alkyl, or
  • R 1 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, fluorine, chlorine, bromine, iodine, cyano, (C 3 -C 10) -cycloalkyl, (C3-Cio) halocycloalkyl, (C 4 -Cio) - cycloalkenyl, (C 4 -Cio) -Halocycloalkenyl, (Ci-Cio) -haloalkyl, (C2-C6) - haloalkenyl, (Ci-C6) alkoxy (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl,
  • heteroaryl heteroaryl (Ci-C 6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 2 -C 6) - haloalkynyl, heterocyclyl, heterocyclyl (Ci-C6) - alkyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylcarbonyl- (C 1 -C 6) -alkyl, hydroxycarbonyl- (C 1 -C 6) -alkyl,
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (Ci -C 6) -alkyl, (C 3 -C 6) -cycloalkyl, nitro, amino, hydroxy, (C 1 -C 6) -alkylamino, bis - [(C 1 -C 6) -alkyl] -amino
  • Alkylaminocarbonyl (C3-C6) -cycloalkylaminocarbonyl, aryl- (Ci-Ce) - alkylaminocarbonyl, heteroarylaminocarbonyl, or
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 6 ) -haloalkyl, cyano- (C 1 -C 6 ) -alkyl, aryl, Heteroaryl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, heterocyclyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alcyl,
  • R 1 , R 9 and R 10 with the carbon atom to which they are attached, a fully saturated, optionally interrupted by heteroatoms and
  • R 7 and R 8 with the carbon atom to which they are attached form an oxo group, or R 7 and R 8 with the carbon atom to which they are attached form a
  • R 11 is (Ci-C 6) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C6) -cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, hydroxy , (C 3 -C 6 ) -cycloalkyloxy, (C 1 -C 6 ) -alkoxy,
  • V, W independently of one another represent oxygen or sulfur, preferably oxygen,
  • X, Y are each independently hydrogen, (Ci-C6) alkyl, fluoro, chloro, (C2-C6) - alkenyl, (Ci-C 6) -haloalkyl, (C3-C6) -cycloalkyl, (C -C 6 ) cycloalkenyl,
  • R 1 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, fluorine, chlorine, bromine, iodine, cyano, (C 3 -C 10) - Cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, (C 1 -C 10) -haloalkyl, (C 6 -C 6 ) -haloalkenyl, (C 1 -C 6 ) - Alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl,
  • heteroaryl heteroaryl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, (C 2 -C 6) - haloalkynyl, heterocyclyl, heterocyclyl (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6 ) -alkyl, hydroxycarbonyl- (C 1 -C 6) -alkyl,
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 6 ) -haloalkyl, cyano- (C 1 -C 6 ) -alkyl, aryl, Heteroaryl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, heterocyclyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, R 1 and R 9 with the carbon atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
  • R 1 , R 9 and R 10 with the carbon atom to which they are attached, a fully saturated, optionally interrupted by heteroatoms and
  • R 11 is (Ci-C 6) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C6) -cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, hydroxy, (C3 -C 6 ) -cycloalkyloxy, (Ci-Ce) -alkoxy,
  • W is oxygen or sulfur, preferably oxygen.
  • R 1 is hydrogen, fluorine, chlorine, bromine, iodine, preferably fluorine and chlorine, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2- Trimethylpropyl, 1,2,
  • Methoxy-n-pentyl 2-methoxy-2-methylpropyl, 2-methoxy-1-methylpropyl, ethoxymethyl, ethoxyethyl, ethoxy-n-propyl, ethoxy-iso-propyl, ethoxy-n-butyl, ethoxy-n-pentyl, 2-ethoxy-2-methylpropyl, 2-ethoxy-1-methylpropyl, n-propyloxymethyl, n-propyloxyethyl, n-propyloxy-n-propyl, n-propyloxy-isopropyl, n-propyloxy-n-butyl, 2- n-propyloxy-2-methylpropyl, 2-n-propyloxy-1-methylpropyl, iso -propyloxymethyl, iso -propyloxyethyl, iso-propyloxy-n-propyl, iso-propyloxy-iso
  • Heterocyclyl (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkylsulfonyl, (C 3 -C 6) -cycloalkylsulfonyl, arylsulfonyl, aryl- (C 1 -C 6) -alkylsulfonyl, heteroarylsulfonyl, heterocyclylsulfonyl, dimethylamino, diethylamino, methyl (ethyl) amino,
  • Triisopropylsilylethynyl 2-pyridylethynyl, 3-pyridylethynyl, 4-chloro-3-pyridylethynyl,
  • R 5 is methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,
  • Pentafluoroethyl 1,1,2,2-difluoroethyl, 2,2-difluoroethyl, 3,3,3-trifluoroethyl,
  • R 11 represents methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,
  • W is oxygen or sulfur, preferably oxygen.
  • R 1 is hydrogen, fluorine, methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -
  • Trifluoromethyl difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, pentafluoroethyl, chlorodifluoromethyl, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-n-butyl, cyano-iso propyl, methoxymethyl,
  • Methoxyethyl methoxy-n-propyl, methoxy-iso-propyl, methoxy-n-butyl,
  • Methoxy-n-pentyl 2-methoxy-2-methylpropyl, 2-methoxy-1-methylpropyl, ethoxymethyl, ethoxyethyl, ethoxy-n-propyl, n-propyloxymethyl, n-propyloxyethyl, methoxymethoxymethyl, methoxymethoxy, ethoxymethoxy, methoxyethoxy, methoxy n-propyloxy, ethoxy-n-propyloxy, n-propyloxymethoxy, methoxymethoxyethyl, ethoxymethoxymethyl,
  • Ethoxyethoxymethyl methoxyethoxymethyl, methoxyethoxyethyl, Trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl,
  • Pentafluoroethoxymethyl pentafluoroethoxyethyl, 2,2,2-trifluoroethoxynethyl, 2,2,2-trifluoroethoxyethyl, trifluoromethylthionethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, pentafluoroethylthiomethyl, pentafluoroethylthioethyl, hydroxycarbonylmethyl, 1-hydroxycarbonyleth-1-yl, 1-hydroxycarbonyleth-2 yl, hydroxycarbonyl-n-propyl, methoxycarbonylmethyl, 1-methoxycarbonyleth-1-yl, 1-methoxycarbonyleth-2-yl, methoxycarbonyl-n-propyl, ethoxycarbonylmethyl, 1-ethoxycarbonyleth-1-yl, 1-ethoxycarbonyleth-2-yl, Ethoxycarbonyl-n-
  • R 4 independently of one another represent hydrogen, fluorine, chlorine, methoxy, ethoxy, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl,
  • Trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio is methyl, ethyl, propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, n-hexyl, cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, optionally substituted phenyl, heteroaryl, heterocyclyl, aryl (Ci-C 5 ) -alkyl, heteroaryl (Ci-C 5 ) -alkyl, heterocyclyl (Ci-C 5 ) -alkyl, aryloxy- (Ci-C5 ) -alkyl, optionally substituted phenyloxy, is hydrogen, methyl, ethyl, isopropyl, n-butyl, methylcarbonyl,
  • Ethylcarbonyl iso -propylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, p-chlorophenylcarbonyl, methoxycarbonyl, tert -butyloxycarbonyl, methylsulfonyl, phenylsulfonyl, 4-cyanophenylsulfonyl, 4-fluorophenylsulfonyl, 4-chlorophenylsulfonyl, 4-bromophenylsulfonyl, naphth-1-ylsulfonyl, naphth-2 - ylsulfonyl, 4-iodophenylsulfonyl, 4-methoxyphenylsulfonyl, 4-fluoromethylphenylsulfonyl, 4-thfluoromethoxyphenylsulfonyl, 3-cyanophenylsulfonyl, (4-cyanoph
  • R 1 , R 9 and R 10 with the carbon atom to which they are attached, a fully saturated, optionally interrupted by heteroatoms and
  • R 11 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl,
  • W is oxygen or sulfur, preferably oxygen.
  • Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting material or preparation required in each case for the preparation Intermediates. These remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
  • Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • AI kylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl AI, preferably with 1 to 8, or with 1 to 6 carbon atoms, e.g.
  • alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1, 1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethyl-propylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methyl
  • heteroarylsulfonyl is optionally substituted
  • Alkylcarbonylamino, dialkylamino or alkoxy groups Alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4 ) -alkylthio, for example (but not limited to) (C 1 -C 4 ) -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethyl thio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethyl
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio means an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom
  • alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2 Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethyl-propylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl
  • alkenylsulfonyl and alkynylsulfonyl are defined according to the invention as alkenyl or alkynyl radicals which are linked to the skeleton via -S (OO) 2, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -) C) -alkenylsulfonyl or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C) -alkynylsulfonyl.
  • -S (OO) 2 such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -) C) -alkenylsulfonyl or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C) -alkynylsulfonyl.
  • Alkoxy means an alkyl radical attached via an oxygen atom, for example (but not limited to) (C 1 -C 6) -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy , 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-
  • Oxygen-bonded alkenyl radical, alkynyloxy means one over one
  • Oxygen-bonded alkynyl such as (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10) -, (Cs-Ce) - or (C 3 -C) -alkynoxy
  • Cycloalkyloxy means a cycloalkyl radical bonded through an oxygen atom
  • cycloalkenyloxy represents a cycloalkenyl radical attached via an oxygen atom.
  • -C (OO) - such as (C 1 -C 10) -, (C 1 -C 6 ) - or (C 1 -C 4) -alkylcarbonyl
  • the number of C atoms here refers to the alkyl radical in the alkylcarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • alkenyloxycarbonyl and “alkynyloxycarbonyl” are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -O-C (OO) -, such as (C 2 -C 10) - , (C 2 -C 6) - or (C 2 -C 4 ) -alkenyloxycarbonyl or (C 3 -C 10) -, (C 3 -C 6) - or (C 3 -C 4 ) -alkynyloxycarbonyl.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or
  • alkynyloxycarbonyl Alkynyloxycarbonyl.
  • the number of C atoms here refers to the alkyl radical in the alkylcarbonyloxy group.
  • alkenylcarbonyloxy and “alkynylcarbonyloxy” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via (-C (OO) -O-), such as (C 2 -C 10) -, (C 2 -C 4) -C 6) - or (C 2 -C 4 ) -alkenylcarbonyloxy or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkynylcarbonyloxy.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or
  • polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the binding site is on the aromatic system
  • Rule also includes the term "optionally substituted phenyl”.
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
  • Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
  • heteroatom from the group N, O and S 1 - or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3-yl, 2, 3-dihydro-1 H-pyrrole 1 - or 2 - or
  • 2- or 3-tetrahydrothiophenyl 2,3-dihydrothiophene-2 or 3 or 4 or 5-yl; 2,5-dihydrothiophene-2 or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 4H-thiopyran-2- or 3- or 4-yl.
  • Preferred 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl. Further examples of
  • Heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 - or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 - or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-Dioxazepan-2 or 3 or 5 or
  • Heterocycles listed above are at one or more positions, preferably one position, for example in the case of several substituents by the same or various radicals selected from the group consisting of hydrogen, halogen, alkyl,
  • Haloalkyl hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example at N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also short SO2) in the heterocyclic ring.
  • N (O), S (O) (also SO for short) and S (O) 2 (also short SO2) in the heterocyclic ring.
  • -N (O) and -S (O) groups both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie completely unsaturated aromatic heterocyclic compounds
  • Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl
  • heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
  • quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
  • pyridopyrimidines Pyridopyridazine; pteridines; Pyrimidopyrimidine.
  • Heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1 H-indol-1-yl, 1 H-indol-2-yl, 1 H-indol-3-yl, 1 H-indol-4-yl, 1 H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl , 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1 - Benzothiophen-4-yl, 1-benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazol-1-yl, 1H-
  • Benzisoxazol-7-yl 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1, 2 benzisothiazol-7-yl.
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred
  • bis also includes the combination of different alkyl radicals, for example, methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means the same or different
  • Polyhaloalkyl such as CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated
  • Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
  • Hydrocarbon chain can be located, such as. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
  • Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (C 1 -C 4 ) -alkyl given here by way of example means a
  • Carbon atoms corresponding to the range for C atoms, d. H. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl
  • General alkyl radicals having a larger specified range of carbon atoms eg. As "(Ci-C6) alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
  • Alkyl radicals including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1, 3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the Meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained.
  • alkenyl also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulative double bonds, such as For example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not
  • (C 2 -C 6) alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl , 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 -
  • Methyl 3-butenyl 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl
  • alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1 -yl.
  • (C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-yl propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl- 3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentyn
  • Haloalkyl amino, alkylamino, bisalkylamino, alkocycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl.
  • substituents having a double bond on
  • Cycloalkyl, z As an alkylidene group such as methylidene, are included.
  • polycyclic aliphatic systems are also included, such as bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1.0] pentane 1 -yl, bicyclo [1 .1 .1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl,
  • (C 3 -C 7) -cycloalkyl means a
  • substituted cycloalkyl are also spirocyclic aliphatic
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1 - Cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl radical, e.g. Legs
  • Alkylidene group such as methylidene, are included. In case of if necessary
  • Cycloalkylidene means a carbocyclic radical which is bonded via a double bond.
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • Oxotetrahydroquinolinylphosphinic and phosphonic acid amides of general formula (I) can be prepared by known methods.
  • the synthetic routes used and investigated are based on commercially available or easily prepared Oxotetrahydrochinolinylaminen and the corresponding
  • Oxotetrahydroquinolinylamines (A) can be prepared starting from appropriately substituted anilines (Scheme 1). In this case, an optionally further substituted aniline with a corresponding Halogenpropionklarehalogenid using a suitable base in a suitable polar aprotic
  • Oxotetrahydrochinolinen be implemented in which in further reaction steps, first the radical CR 1 R 9 R 10 , wherein R 1 , R 9 and R 10 have the above-mentioned meaning, with the aid of a suitable base (eg., Sodium hydride, potassium carbonate or cesium carbonate ) in a suitable polar aprotic solvent (eg
  • Tin (II) chloride dihydrate, iron in acetic acid or hydrogen over palladium on carbon) is converted to the corresponding amino group. So you get the
  • Oxotetrahydroquinoline is obtained via a tandem reaction of an optionally further substituted alkyl acrylate with an optionally further substituted o-haloaniline by tributyltin hydride and azo-bis (isobutyronitrile) (corresponding to the abbreviation AIBN) (see Tetrahedron 2009, 65, 1982, B. Giese et Org React 1996, 48).
  • This type of cyclization can also be carried out electrocatalytically or photochemically (compare J. Org. Chem., 1991, 56, 3246, J. Am. Chem. Soc., 2009, 131, 5036, Photochem., & Photobiol., 2009, 8 , 751).
  • Another alternative to the preparation of nitro-substituted oxotetrahydroquinolines is the
  • Alkylation can be introduced, can be prepared via alternative synthetic routes. By way of example, but not limitation, some of these approaches are described below.
  • 'dba' stands for dibenzylideneacetone
  • BINAP stands for 2,2'-bis (diphenylphosphino) -1, 1'-binaphthyl
  • t-BuXPhos for 2-di-tert-butylphosphino-3,4,5,6 tetramethyl 2 ', 4', 6'-triisopropyl-1, 1'-biphenyl.
  • a suitable Lewis acid eg., Aluminum trichloride or titanium tetrachloride
  • a suitable reducing agent eg stannous chloride hydrate, iron in acetic acid or hydrogen with palladium on carbon
  • R 1 haloalkyl
  • the synthesis of the relevant N-haloalkylmethyl-substituted, optionally further substituted oxotetrahydroquinolinylamines proceeds by way of example but not limitation via an alkylation using a suitable haloalkyl trifluoromethanesulfonate and a suitable base (eg
  • a suitable polar aprotic solvent e.g., N, N-
  • N-haloalkylmethyl-substituted nitro-oxotetrahydroquinoline may be substituted into the desired N-haloalkylmethyl-substituted by reduction with a suitable reducing agent (e.g., stannous chloride hydrate, iron in acetic acid or hydrogen with palladium on carbon) and optionally further substituted oxotetrahydroquinolinylamine (C) is converted.
  • a suitable reducing agent e.g., stannous chloride hydrate, iron in acetic acid or hydrogen with palladium on carbon
  • a suitable amine base eg triethylamine or
  • Diisopropylethylamine in a suitable polar aprotic solvent (e.g., N, N-dimethylformamide, dioxane) at elevated temperature.
  • a suitable polar aprotic solvent e.g., N, N-dimethylformamide, dioxane
  • a suitable transition metal catalyst for example, (P i3P) 3RhCl, in a suitable ploar-protic solvent (eg, methanol, ethanol) is converted to the corresponding substituted 3- [2- (cycloalkylamino) -5-nitrophenyl] propanoate.
  • the resulting substituted 3- [2- (cycloalkylamino) -5-nitrophenyl] propanoate is then treated with a suitable base (e.g., sodium hydride) in a suitable polar aprotic solvent (e.g., diethyl ether, tetrahydrofuran) in the appropriate substituted 1-cycloalkyl-2-oxotetrahydroquinoline converted.
  • a suitable reducing agent eg, tin (II) chloride hydrate, iron in
  • Acetic acid or hydrogen with palladium on carbon for example, the optionally further substituted 6-amino-1 - (spiro [3.3] hept-2-yl) -3,4-dihydroquinoline-2 (1 H) -one (D) or, correspondingly, the optionally further substituted 6-amino-1 - ( bicyclo [1 .1 .1] pent-1-yl) -3,4-dihydroquinoline-2 (1 H) -one (E) (Scheme 4).
  • R 2 , R 3 , R 4 are exemplified but not limited to H and W are exemplified but not limited to O.
  • 6-amino-1 - [1, 1 '-bi (cyclopropyl) -2-yl] - 3,4-dihydroquinoline-2 (1 H) -one (F) or according to the optionally further substituted 6-Amino-1 - [1,1 '-bi (cyclopropyl) -1-yl] -3,4-dihydroquinoline-2 (1H) -one (G) can be prepared (Scheme 5).
  • R 2 , R 3 , R 4 are exemplified but not limited to H and W are exemplified but not limited to O.
  • Phosphorus compound e.g. Sodium diethyl phosphite, triethyl phosphite, or a correspondingly substituted Arbuzov Diethylalkylphosphonit be prepared in a suitable polar aprotic solvent (eg, ⁇ , ⁇ -dimethylformamide or diethyl ether).
  • a suitable polar aprotic solvent eg, ⁇ , ⁇ -dimethylformamide or diethyl ether
  • the phosphonic and phosphinic esters may be converted to the corresponding acid intermediates (I) with an appropriate base (e.g., sodium hydroxide) at elevated temperature (second reaction in Scheme 6).
  • an appropriate base e.g., sodium hydroxide
  • Phosphinyl chloride precursors (K) (Scheme 6) (see Org. Lett 2005, 7, 4919, US2008 / 0008682, DE102061 17, JP63218684, DE3400509, J. Org. Chem. 1992, 57, 4292).
  • the coupling of the corresponding substituted phosphonyl chloride and phosphinyl chloride precursors with the corresponding optionally further substituted oxotetrahydroquinolinylamines with the aid of a suitable base (eg triethylamine, pyridine) in a suitable solvent (eg tetrahydrofuran, Acetonitrile, DMSO or dichloromethane) (see J. Med. Chem.
  • R 1 , R 2 , R 3 , R 4 , R 9 , R 10 and R 11 have in the following Scheme 6 the meanings defined above.
  • R 7 , R 8 , X and Y are exemplified by H, but not by way of limitation.
  • R 5 is exemplified by, but not limited to, p-chlorobenzyl and p-methylbenzyl.
  • R 11 in the second reaction in Scheme 6 is exemplified by, but not limited to, methyl.
  • Example numbers correspond to the numbers given in Tables A1 to E4 below.
  • 6-nitro-3,4-dihydroquinoline-2 (1 H) -one (20.0 g, 76% of theory) was isolated as a colorless solid.
  • 6-Nitro-3,4-dihydroquinoline-2 (1 H) -one (8.52 g, 44.38 mmol) was dissolved under argon in abs.
  • Dissolved N, N-dimethylformamide (150 ml), cooled to 0 ° C and treated with finely powdered potassium carbonate (7.40 g, 52.26 mmol). After stirring for 15 minutes at a
  • Triethyl phosphite (2.00 g, 12.04 mmol) and 4-methylbenzyl bromide (15.65 mmol) were placed in a baked microwave vessel and then stirred together under nitrogen for 1 h at a temperature of 140 ° C in the microwave. After completion of the reaction, the resulting crude product was purified by column chromatography (gradient heptane / ethyl acetate) and then a portion of the resulting, purified intermediate (4.43 mmol) with distilled POCl3 (4.43 mmol) and under argon for 1.5 h at a temperature of 60 ° C. touched.
  • Triethyl phosphite (2.00 g, 12.04 mmol) and 2,4-dimethylbenzyl bromide (3.12 g, 15.65 mmol) were placed in a baked microwave vessel and then stirred together under nitrogen for 1 h at a temperature of 140 ° C in the microwave. After complete reaction, the resulting crude product
  • 6-nitro-3,4-dihydroquinoline-2 (1 H) -one (20.0 g, 76% of theory) was isolated as a colorless solid.
  • 6-Nitro-3,4-dihydroquinoline-2 (1 H) -one (8.52 g, 44.38 mmol) was dissolved under argon in abs.
  • Dissolved N, N-dimethylformamide (150 ml), cooled to 0 ° C and treated with finely powdered potassium carbonate (7.40 g, 52.26 mmol). After stirring for 15 minutes at a
  • 6-nitro-3,4-dihydroquinoline-2 (1H) -one (500 mg, 68% of theory) was isolated as a colorless solid. 6-nitro-3,4-dihydroquinoline-2 (1H) -one (500 mg, 2.60 mmol) was dissolved under argon in abs. Dissolved ⁇ , ⁇ -dimethylformamide and mixed with finely powdered potassium carbonate (1.08 g, 7.81 mmol). After stirring at room temperature for 5 min, chloromethylcyclopropane (306 mg, 3.38 mmol) and
  • Trimethyl phosphite (1 equiv, 8.07 mmol) and 4-methylbenzylbromide (1 equiv, 8.07 mmol) were placed in a heated multi-necked flask and then stirred together under continuous nitrogen flow for 10 hours at a temperature of 100 ° C. After completion of the reaction, the resulting crude product without further purification with distilled POCl3 (1 equiv) and stirred under argon for 1.5 for a long time at a temperature of 60 ° C. After complete conversion, the methyl (4-methylbenzyl) phosphonochloridate obtained was reacted directly in the next step without further purification.
  • 6-Amino-1-cyclopropylmethyl-3,4-dihydroquinoline-2 (1H) -one (960 mg, 4.57 mmol) was dissolved in abs. H 2 O in a heated round bottom flask under argon. Tetra hydrofu ran (2 ml) and slowly added dropwise to a cooled to -20 ° C solution of methyl (4-methylbenzyl) phosphonochloridate (1000 mg, 4.57 mmol) in abs.
  • Triethyl phosphite (1 equiv, 8.07 mmol) and 4-methylbenzyl bromide (1 equiv, 8.07 mmol) were placed in a heated multi-necked flask and then stirred together under continuous nitrogen flow for 10 hours at a temperature of 100 ° C. After completion of the reaction, the resulting crude product without further purification with distilled POCl3 (1 equiv) and stirred under argon for 1.5 for a long time at a temperature of 60 ° C. After complete conversion, the ethyl (4-methylbenzyl) phosphonochloridate obtained was reacted directly in the next step without further purification.
  • 6-nitro-3,4-dihydroquinoline-2 (1 H) -one (500 mg, 68% of theory) was isolated as a colorless solid.
  • 6-nitro-3,4-dihydroquinoline-2 (1H) -one (500 mg, 2.60 mmol) was dissolved under argon in abs.
  • Triethyl phosphite (1 equiv, 8.07 mmol) and 2,4-dichlorobenzyl bromide (1 equiv, 8.07 mmol) were placed in a heated multi-necked flask and then combined under
  • Tetrahydrofuran (5 ml) was added under argon. The resulting reaction mixture was stirred for 1 h at 0 ° C and then cautiously treated with water and after stirring for 5 min with ethyl acetate. The aqueous phase was then extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • Tin (II) chloride dihydrate (298 mg, 1 .32 mmol) in abs. Ethanol (5 ml) and stirred for 5 h under argon at a temperature of 80 ° C. After cooling to room temperature, the reaction mixture was poured onto ice water and then adjusted to pH 12 with aqueous NaOH. The aqueous phase was then extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • 6-Amino-1 - [1,1 '-bi (cyclopropyl) -1-yl] -3,4-dihydroquinoline-2 (1H) -one (1 108 mg, 4.57 mmol) was dissolved in a heated round bottom flask under argon in abs.
  • Triethyl phosphite (1 equiv, 8.07 mmol) and 4-methylbenzyl bromide (1 equiv, 8.07 mmol) were placed in a heated multi-necked flask and then stirred together under continuous nitrogen flow for 10 hours at a temperature of 100 ° C. After completion of the reaction, the resulting crude product without further purification with distilled POCl3 (1 equiv) and stirred under argon for 1.5 for a long time at a temperature of 60 ° C. After complete conversion, the ethyl (4-methylbenzyl) phosphonochloridate obtained was reacted directly in the next step without further purification.
  • 6-Amino-1 - [1,1 '-bi (cyclopropyl) -1-yl] -3,4-dihydroquinoline-2 (1 H) -one (1042 mg, 4.29 mmol) was dissolved in a heated round bottom flask under argon Section. Dissolved tetrahydrofuran (2 ml) and slowly added dropwise to a cooled to -20 ° C solution of ethyl (4-methylbenzyl) phosphonochloridat (1000 mg, 4.29 mmol) in abs. Add tetrahydrofuran (10 ml) in a previously heated round bottom flask under argon.
  • Tetra hydrofu ran (8 ml) and dropwise cooled to 0 ° C Suspension of sodium hydride (88 mg, 2.21 mmol, 60% suspension in oil) in abs. Tetrahydrofuran (5 ml) was added under argon. The resulting reaction mixture was stirred for 1 h at 0 ° C and then cautiously treated with water and after stirring for 5 min with ethyl acetate. The aqueous phase was then extracted several times with ethyl acetate. The combined organic phases were over
  • reaction mixture was poured onto ice water and then adjusted to pH 12 with aqueous NaOH.
  • aqueous phase was then extracted several times with ethyl acetate.
  • the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • Trimethyl phosphite (1 equiv, 8.07 mmol) and 4-methylbenzylbromide (1 equiv, 8.07 mmol) were placed in a heated multi-necked flask and then stirred together under continuous nitrogen flow for 10 hours at a temperature of 100 ° C. After completion of the reaction, a portion of the resulting crude product (170 mg) was taken up in aqueous NaOH (10%, 5 ml) without further purification and stirred for 2 hours under reflux conditions. After cooling to room temperature, careful addition of dilute hydrochloric acid followed by thorough extraction with dichloromethane and water. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.

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Abstract

L'invention concerne des amides substitués d'acide phosphonique et d'acide oxotétrahydrochinolinylphosphinique de formule générale (I) ou leurs sels, les restes de la formule (I) répondant aux définitions mentionnées dans la description, pour augmenter la tolérance des plantes au stress abiotique et pour renforcer la croissance des plantes et/ou pour augmenter le rendement des plantes.
EP16738159.9A 2015-07-15 2016-07-12 Amides substitués d'acide phosphonique et d'acide oxotétrahydrochinolinylphosphique, ou leurs sels et leur utilisation pour accroître la tolérance au stress chez les végétaux Withdrawn EP3322296A1 (fr)

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EP3788054B1 (fr) 2018-04-30 2022-07-20 Unity Biotechnology, Inc. Phospholidines à titre d'antagonistes de la famille bcl destinées à être utilisées dans la gestion clinique d'états pathologiques provoqués ou induits par des cellules sénescentes ainsi que dans le traitement du cancer
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