Back to results
US 12,559,503 B2Granted
Anthelmintic aza-benzothiophene and aza-benzofuran compounds
OwnerAlan Long, Hannes Fiepko Koolman +1inventors
InventorsAlan Long, Hannes Fiepko Koolman, Hyoung Ik Lee
Life of this patent
Estimating the term…
Abstract
This invention provides for compounds of the formula: wherein the variables are defined herein, or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, compositions comprising these compounds, and method for the treatment, control or prevention of a parasitic infestation or infection in an animal in need thereof by administering an effective amount of these compounds to said animal.
Claims30
A compound of Formula I:
- or salt thereof,
- wherein:
- L is L1 or L2:
- R1 is optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted heterocyclyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —SOp (optionally substituted alkyl) or —SOp (optionally substituted haloalkyl), —SF5, or —NRaRb wherein Ra and Rb are independently H or optionally substituted alkyl;
- or Ra and Rb may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
- R2 is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl;
- R2′ is optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl;
- R3 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —S(O)p (optionally substituted alkyl), —SF5, optionally substituted heterocyclyl, optionally substituted 6- to 10-membered aryl, optionally substituted 5- to 10-membered heteroaryl, a spirocyclic heterocyclyl-carbocyclyl group, a spirocyclic heterocyclyl-heterocyclyl group, a spirocyclic carbocyclyl-carbocyclyl group, a spirocyclic carbocycylyl-heterocyclyl group, or —NRaRb wherein Ra and Rb are independently H or optionally substituted alkyl;
- or Ra and Rb may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
- R4 is independently in each occurrence hydrogen, cyano, halogen, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl;
- optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted heterocyclyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —SOp (optionally substituted alkyl) or —SOp (optionally substituted haloalkyl), —SF5, or —NRaRb wherein Ra and Rb are independently H or optionally substituted alkyl;
- or Ra and Rb may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
- R5 and R5′ are independently in each occurrence, hydrogen, halogen, cyano, nitro, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted aryl, optionally substituted heteroaryl, —SF5, —SOp (optionally substituted alkyl) or —SOp (optionally substituted haloalkyl), or —NRcRd wherein Rc and Rd are independently H or optionally substituted alkyl;
- or Rc and Rd may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
- R10 is hydrogen, halogen, alkyl, haloalkyl, cycloalkyl, alkenyl or alkynyl;
- X is O or S;
- Q is O, S or NR2′;
- Y1 is N;
- Y2 is N or —CR4;
- and Y3 is N or —CR4;
- or
- Y1 is —CR4;
- Y2 is N;
- and Y3 is N or —CR4;
- Y1′ and Y6′ are each independently N, C, or —CR5—;
- Y2′, Y3′, Y4′, Y5′ are each independently N, NR2, S, O, —CR5— or CR5R5′;
- W is CR6R7, O, S, or N—R8,
- Z is CR6R7, O, S, or N—R8,
- wherein
- R6 and R7 are independently in each occurrence hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C3-C8-cycloalkoxy;
- R8 is hydrogen or C1-C4-alkyl;
- and
- wherein at most three of Y1′, Y2′, Y3′, Y4′, Y5′ and Y6′ are heteroatoms;
- a is 0 or 1;
- q is 0 or 1;
- p is independently in each occurrence is 0, 1, or 2;
- and
- the dashed bonds signify a single or double bond.
35 more elements
A compound, or a salt thereof, selected from the group consisting of:
Dependencies are inferred from the claim text.