WO2021204930A1 - Substituted condensed azines as anthelmintic compounds - Google Patents

Substituted condensed azines as anthelmintic compounds Download PDF

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Publication number
WO2021204930A1
WO2021204930A1 PCT/EP2021/059144 EP2021059144W WO2021204930A1 WO 2021204930 A1 WO2021204930 A1 WO 2021204930A1 EP 2021059144 W EP2021059144 W EP 2021059144W WO 2021204930 A1 WO2021204930 A1 WO 2021204930A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
halogen atoms
halogenoalkyl
group
alkoxy
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.)
Ceased
Application number
PCT/EP2021/059144
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English (en)
French (fr)
Inventor
Nils Griebenow
Daniel Kulke
Iring Heisler
Wei Zhuang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Elanco Animal Health GmbH
Original Assignee
Bayer Animal Health GmbH
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 Bayer Animal Health GmbH filed Critical Bayer Animal Health GmbH
Priority to US17/995,750 priority Critical patent/US20230174492A1/en
Priority to MX2022012652A priority patent/MX2022012652A/es
Priority to EP21717431.7A priority patent/EP4132911A1/en
Priority to BR112022020315A priority patent/BR112022020315A2/pt
Priority to JP2022561054A priority patent/JP2023521342A/ja
Priority to AU2021253168A priority patent/AU2021253168A1/en
Priority to CN202180041481.9A priority patent/CN115667221A/zh
Priority to CA3179528A priority patent/CA3179528A1/en
Publication of WO2021204930A1 publication Critical patent/WO2021204930A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Definitions

  • the compounds of the present invention have surprisingly been found to effectively interact with Slo-1 of nematodes.
  • This interaction is characterized by achieving paralysis/inhibition in particular of gastro-intestinal nematodes, of free-living nematodes, and of filariae, for which data are given in the biological experimental section. Therefore the compounds of the present invention may be used as anthelmintics for the control, treatment and/or prevention of gastro-intestinal and extra-intestinal helminth infections, in particular gastro-intestinal and extra-intestinal infections with nematodes, including filariae.
  • R 15 is selected from the group consisting of
  • halogen atoms 1 to 5 halogen atoms, -S(0)-Ci-C 4 -halogenoalkyl having 1 to 5 halogen atoms and -S0 2 -Ci-C 4 - halogenoalkyl having 1 to 5 halogen atoms; phenyl, which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, Ci-C 4 -alkyl, Ci-C 4 -halogenoalkyl having 1 to 5 halogen atoms, Ci-C 4 -alkoxy, Ci-C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C3-C6- cycloalkyl, -NH 2 , -NH(Ci-C 4 -alkyl), -N(Ci-C 4 -alkyl) 2 , -S-Ci-C t -alkyl,
  • an oxo substituent represents an oxygen atom, which is bound to a carbon atom or to a sulfur atom via a double bond.
  • ring substituent means a substituent attached to an aromatic or nonaromatic ring which replaces an available hydrogen atom on the ring.
  • Ci-C t -hydroxyalkyl means a linear or branched, saturated, monovalent hydrocarbon group in which the term “Ci-Cralkyl” is defined supra, and in which 1 or 2 hydrogen atoms are replaced with a hydroxy group, e.g.
  • heterocycloalkyr means a monocyclic or bicyclic, saturated or partially saturated heterocycle with 4, 5, 6, 7, 8, 9 or 10 ring atoms in total (a “4- to 10-membered heterocycloalkyr’ group), particularly 4, 5 or 6 ring atoms (a “4- to 6-membered heterocycloalkyl” group), which contains one or two identical or different ring heteroatoms from the series N, O and S, it being possible for said heterocycloalkyl group to be attached to the rest of the molecule via any one of the carbon atoms or, if present, a nitrogen atom.
  • Said heteroaryl group can be a 5-membered heteroaryl group, such as, for example, thienyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl or tetrazolyl; or a 6-membered heteroaryl group, such as, for example, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl ortriazinyl.
  • a 5-membered heteroaryl group such as, for example, thienyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl
  • deuterium-containing compound of general formula (I) is defined as a compound of general formula (I), in which one or more hydrogen atom(s) is/are replaced by one or more deuterium atom(s) and in which the abundance of deuterium at each deuterated position of the compound of general formula (I) is higher than the natural abundance of deuterium, which is about 0.015%.
  • the abundance of deuterium at each deuterated position of the compound of general formula (I) is higher than 10%, 20%, 30%, 40%, 50%, 60%, 70% or 80%, preferably higher than 90%, 95%, 96% or 97%, even more preferably higher than 98% or 99% at said position(s). It is understood that the abundance of deuterium at each deuterated position is independent of the abundance of deuterium at other deuterated position(s).
  • the present invention includes all possible stereoisomers of the compounds of the present invention as single stereoisomers, or as any mixture of said stereoisomers, e.g. (R)- or (S)- isomers, in any ratio.
  • Isolation of a single stereoisomer, e.g. a single enantiomer or a single diastereomer, of a compound of the present invention is achieved by any suitable state of the art method, such as chromatography, especially chiral chromatography, for example.
  • an alkali metal salt for example a sodium or potassium salt
  • an alkaline earth metal salt for example a calcium, magnesium or strontium salt, or an aluminium or a zinc salt
  • the present invention covers compounds of general formula (I), as defined supra, wherein the subsituent Q may have one of the following preferred meanings:
  • R 6 is selected from the group consisting of hydrogen, fluorine, chlorine, -OH, cyano, methyl and methoxy,
  • # 1 indicates the binding position between the groups T and L
  • R 4 is selected from the group consisting of hydrogen, fluorine, chlorine, -OH, cyano, methyl, methoxy, trifluoromethyl, trifluoromethoxy, and N3 ⁇ 4; preferably from the group consisting of hydrogen, fluorine, chlorine, methyl and trifluoromethyl; more preferably from the group consisting of hydrogen, fluorine and chlorine; and stereoisomers, tautomers, N-oxides, hydrates, solvates, and salts thereof, and mixtures of same.
  • R 6 is selected from the group consisting of hydrogen, fluorine, chlorine, -OH, cyano, methyl and methoxy, preferably from the group consisting of hydrogen, fluorine, chlorine and methyl; and stereoisomers, tautomers, N-oxides, hydrates, solvates, and salts thereof, and mixtures of same.
  • a “fixed combination” in the present invention is used as known to persons skilled in the art and is defined as a combination wherein, for example, a first active ingredient, such as one or more compounds of general formula (I) of the present invention, and a further active ingredient are present together in one unit dosage or in one single entity.
  • a “fixed combination” is a pharmaceutical composition wherein a first active ingredient and a further active ingredient are present in admixture for simultaneous administration, such as in a formulation.
  • Another example of a “fixed combination” is a pharmaceutical combination wherein a first active ingredient and a further active ingredient are present in one unit without being in admixture.
  • Ryanodine receptor modulators such as, for example, diamides, e.g. chlorantraniliprole, cyantraniliprole and flubendiamide, further active ingredients such as, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxamet
  • Step 4 /V 4 V 4 -dimethyl-8-(2,3,5-trifluorophenyl)quinoline-3, 4-diamine
  • Step 1 Ethyl 4-ethyl-8-(2,3,5-trifluorophenyl)quinoline-3-carboxylate
  • Step 5 A-(4-cthyl-8-(2.3.5-tnfluorophcnyl)quinolin-3-yl)chromanc-4-carboxamidc
  • Step 1 Ethyl 7-fluoro-4-(4-(mcthoxycarbonyl)-tctrahydro-2//-pyran-4-yl)-8-(2.3.5- trifluorophenyl)quinoline -3 -carboxylate
  • Step 4 A-(7-Fluoro-4-(tctrahydro-2//-pyran-4-yl)-8-(2.3.5-trifluorophcnyl)quinolin-3-yl)chroman-4- carboxamide
  • Step 5 7-fluoro-/V(/V # -dimethyl-8-(2, 3, 5-trifluorophenyl)quinoline-3 ,4-diamine
  • Step 4 /V-(4-ethyl-7-fluoro-8-(2,3,5-trifluorophenyl)quinolin-3-yl)chromane-4-carboxamide
  • the transfection medium was exchanged for the selection medium which contains additional G418 (2 mg/ml, Invitrogen, Nr.: 10131) and the cells were seeded into 384 well plates (300 cells/well). After a few weeks, the remaining surviving cells were tested with a voltage sensitive dye (Membrane Potential Assay Kit, Molecular Devices Nr.: R8034) for K+ channel expression. Positive cell clones were purified by the limited dilution technique. For this the clone with the highest and most robust signal in the voltage sensitive dye assay was further subcloned (incubated) in 384 well plates (0.7 cells/well) in order to obtain clonal purity. This generated a final stable CHO cell line expressing the D. immitis b ⁇ o- ⁇ . Cell culture conditions
  • activity reduction of AChE compared to negative control
  • activity was higher than 80% at 0.1 pg/ml: 5, 9, 10, 11, 13, 14, 16, 17
  • Formulation Example Exemplary formulations consisted of the active substance in 10% Transcutol, 10% Cremophor EL and 80% isotonic saline solution. First the active substance is dissolved in Transcutol. After solution in Transcutol, Cremophor and isotonic saline solution are added. These formulations re used as service formulations in the following in vivo assay.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
PCT/EP2021/059144 2020-04-09 2021-04-08 Substituted condensed azines as anthelmintic compounds Ceased WO2021204930A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US17/995,750 US20230174492A1 (en) 2020-04-09 2021-04-08 Substituted condensed azines as anthelmintic compounds
MX2022012652A MX2022012652A (es) 2020-04-09 2021-04-08 Nuevos compuestos antihelminticos.
EP21717431.7A EP4132911A1 (en) 2020-04-09 2021-04-08 Substituted condensed azines as anthelmintic compounds
BR112022020315A BR112022020315A2 (pt) 2020-04-09 2021-04-08 Novos compostos anti-helmínticos
JP2022561054A JP2023521342A (ja) 2020-04-09 2021-04-08 駆虫性化合物としての置換縮合アジン類
AU2021253168A AU2021253168A1 (en) 2020-04-09 2021-04-08 Substituted condensed azines as anthelmintic compounds
CN202180041481.9A CN115667221A (zh) 2020-04-09 2021-04-08 作为驱虫化合物的取代的稠合嗪类
CA3179528A CA3179528A1 (en) 2020-04-09 2021-04-08 Substituted condensed azines as anthelmintic compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20168978.3 2020-04-09
EP20168978 2020-04-09

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WO2021204930A1 true WO2021204930A1 (en) 2021-10-14

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EP (1) EP4132911A1 (https=)
JP (1) JP2023521342A (https=)
CN (1) CN115667221A (https=)
AU (1) AU2021253168A1 (https=)
BR (1) BR112022020315A2 (https=)
CA (1) CA3179528A1 (https=)
MX (1) MX2022012652A (https=)
WO (1) WO2021204930A1 (https=)

Cited By (7)

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US11560388B2 (en) 2019-03-19 2023-01-24 Boehringer Ingelheim Vetmedica Gmbh Anthelmintic aza-benzothiophene and aza-benzofuran compounds
WO2023073641A1 (en) 2021-11-01 2023-05-04 Boehringer Ingelheim Vetmedica Gmbh Anthelmintic pyrrolopyridazine compounds
US11964977B2 (en) 2020-05-29 2024-04-23 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic heterocyclic compounds
WO2024213752A1 (en) 2023-04-14 2024-10-17 Elanco Animal Health Gmbh Long-term prevention and/or treatment of a disease by slo-1 inhibitors
WO2025027117A1 (en) 2023-08-02 2025-02-06 Intervet International B.V. Carboxamide-4-quinoline compounds with anthelmintic activity
US12269822B2 (en) 2018-07-09 2025-04-08 Boehringer Ingelheim Animal Health USA Inc. Anthelminthic heterocyclic compounds
WO2026078157A2 (en) 2024-10-10 2026-04-16 Elanco Animal Health Gmbh Slo-1 modulators for prevention and/or treatment of a disease

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