Cyclopropylamide compounds against parasites in fish
Inventors
Hunter, James Edward • Lawler, Lori Kay • Trullinger, Tony Kent • Walsh, Martin Joseph • Schmitt, Harald • Heckeroth, Anja Regina • Lutz, Jürgen • Fähsing, Maria Daniela • Zoller, Hartmut
Assignees
Intervet International BV • Intervet Inc • Corteva Agriscience LLC
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Publication Number
US-12655090-B2
Publication Date
2026-06-16
Expiration Date
Abstract
The present invention relates to cyclopropylamide compounds that are useful in the treatment of parasitic infestations of fish. The compounds have the formula (I).
Core Innovation
The invention relates to a method to control parasite infestations in fish by administering to a fish a compound of Formula (I) and N-oxides, veterinary acceptable acid addition salts, solvates, isotopes, stereoisomers, tautomers, salt derivatives, ester derivatives, and crystal polymorphs. The compounds are defined through multiple substituent variables R1 through R16 and Q1 and Q2, and Formula variants, including Formula (II), Formula (III), Formula (V), Formula (VI), and Formula (VII), are also described.
The target parasites are sea lice, including Lepeophtheirus salmonis and Caligus spp., and the method addresses infestations affecting juvenile and adult sea lice stages. The disclosed approach administers a compound of Formula (I) to a fish to control the parasite infestation, with preferred embodiments narrowing the substituent variables and structural definitions for the administered agent.
The disclosure also describes composition formats for providing the compound to the fish, including medicated fish feed, medicated water or stock solutions, nutrient premixes, and kits. A key stereochemical finding is described for administering pure or substantially pure RR-cyclopropyl amide isomers with an optical purity of at least 98% or at least 80% RR optical purity, which is stated to improve efficacy while avoiding side effects.
Claims Coverage
The independent claim coverage is directed to administering a Formula (I) compound to control parasite infestations in fish. The inventive features center on the compound-form scope and the method of controlling infestations, with dependent claims narrowing the target to sea lice, constraining infestation conditions, and specifying administration routes and formulations.
Method to control parasite infestations in fish with Formula (I) compound forms
A method to control parasite infestations in fish comprising administering to a fish a compound of Formula (I) and N-oxides, veterinary acceptable acid addition salts, solvates, isotopes, stereoisomers, and tautomers.
Formula (I) substituent-variable definition
R1 through R16 are selected from specified groups, Q1 and Q2 are each independently selected from O and S, and the scope includes broad options for halogenated and other functional groups, including additional optional substitution rules for heterocycle and cycloalkyl groups.
Sea lice infestation targeting
The method controls parasite infestations in fish where the parasite infestation is specifically a sea lice infestation.
Specified sea-lice genus/species targeting
The method controls parasite infestations in fish where the parasite is one or more specified Caligus species or Lepeophtheirus salmonis.
Infestation-rate constrained treatment window
The method controls parasite infestations in fish with an infestation rate of between 0.5 and 3 parasites per fish on average in a fish facility.
Multiple administration routes for Formula (I) compounds
A method for controlling parasite infestations in fish by administering the compound of Formula (I) via oral administration, topical bath treatment, intraperitoneal injection, or intramuscular injection.
Nutrient premix formulation containing Formula (I) compound
A method in which the treatment uses a premix that includes a compound of Formula (I) and additionally contains nutrients.
The claim coverage is grounded in administering a Formula (I) compound and specified acceptable forms to control parasite infestations in fish. Dependent claims further refine the infestation target to sea lice, apply an infestation-rate criterion, limit administration routes, and include formulation features such as nutrient premix.
Stated Advantages
Maintain efficacy in sea-lice infestations in view of resistance to existing sea-lice chemotherapeutics.
Improved efficacy.
Avoiding side effects.
Low toxicity to fish.
Favorable resistance-breaking properties.
Effective against juvenile and adult sea lice stages.
Documented Applications
Controlling parasite infestations in fish, specifically sea lice infestations, including Lepeophtheirus salmonis and Caligus spp., with specified life stages.
Use in fish facilities where sea-lice monitoring thresholds and infestation-rate conditions are applied.
Providing the compound in veterinary/commercial treatment formats including medicated fish feed, medicated water or stock solutions, nutrient premixes, and kits for administering the compound to fish.
Therapeutic and prophylactic treatment via oral administration, topical bath treatment/immersion, and injection routes.
Combination therapy using other antiparasitic, antibiotic, or vaccine components as part of the treatment approach.
Treatment and prevention of sea lice infestations in fish under specified infestation conditions.
Use with administration routes including oral administration, bath immersion or topical bath treatment, and intraperitoneal or intramuscular injection.
Formulation as a nutrient premix and use in medicated fish feed, including coated pellets and kit-type embodiments.
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