US 2026/0215420 A1Published application

Insect neuropeptide analogues

AssigneeSolasta Bio Limited

InventorsJulian A.T. Dow, Shireen A. Davies, Yousef Abul-Haija, Lewis Archibald

Life of this patent

Estimating the term…

Abstract

The present invention relates to analogues of insect neuropeptides having activity against insects, such as insects of the order diptera, hemiptera, blattodea and/or lepidoptera, and their use as insect control agents (e.g. insecticides) and plant protection agents.

Claims28

Dependent claims

An insecticidal compound having the formula (XX) below, or a salt or solvate thereof:

wherein:
R1 is hydrogen (which may be designated “H-” or “Hy-”), C1-4alkyl (e.g. methyl, ethyl, propyl, butyl), formyl, —N(R1a)—C(═N+(R1b)(R1c))NR1dR1e, —C(═N+(R1b)(R1c))NR1dR1e, acyl, fatty acyl, benzyl, benzoyl, heteroaryl or trifluoroacetyl, —NHC1-18alkyl, —NHC6-16Aryl, —NH—C1-6alkyl-C6-10aryl, biotin, a sugar moiety or (poly)alkyleneglycol, phosphate or sulphate;
wherein each of R1a, R1b, R1c, R1d and R1e is independently selected from hydrogen or C1-4 alkyl (e.g. methyl, ethyl, propyl, butyl);
and any alkyl, formyl, acyl, fatty acyl, benzyl, benzoyl, heteroaryl or trifluoroacetyl, —NHC1-18alkyl, —NHC6-16Aryl, —NH—C1-6alkyl-C6-10aryl or (poly)alkyleneglycol may optionally be substituted with one or more groups selected from halogen, C1-6alkyl, C1-6haloalkyl, a sugar moiety, phosphate or sulphate;
L1 is absent or is:
*—(C═O)C1-6-alkylene-NH— where * denotes the point of attachment to Y1, Y or Z;
(C1-20)alkylene,
(C2-20)alkenylene,
(poly)alkyleneglycol;
wherein L1 is optionally substituted with one or more groups selected from oxo (═O), halogen, ═N and ═S;
Y1 is absent or is a peptide comprising from 1 to 2 amino acids;
Y is absent or is a peptide comprising from 1 to 16 amino acids;
wherein Y optionally comprises a (poly)alkyleneglycol linker in the peptide sequence;
Y2 is absent or is a peptide comprising from 1 to 2 amino acids;
Z is a peptide of the formula:
wherein:
X2 is selected from S#, Y#, K#, N# or Hm;
X3 is selected from S#, A#, P#, V# or T#
X5 is selected from G#, A#;
wherein “#” indicates that the listed residue is independently the unmodified amino acid, a modified amino acid or a non-natural amino acid analogue;
R2 is NH2, NR2aH, NR2aR2b, OH or OR2a;
wherein each of R2a and R2b if present are independently C1-6-alkyl (e.g. methyl, ethyl, propyl, butyl, pentyl or hexyl), C3-6-alkenyl, C6-16-aryl, C6-16-aryl-C1-6-alkyl, C1-6-alkylene-C6-16-aryl, or C1-6 haloalkyl, each of which may optionally be substituted with one or more groups selected from halogen, C1-6-alkyl, or C1-6-haloalkyl.

19 more elements

An insecticidal compound having the formula (I) below, or a salt or solvate thereof:

wherein:
R1 is hydrogen (which may be designated “H-” or “Hy-”), C1-4alkyl (e.g. methyl, ethyl, propyl, butyl), formyl, —N(R1a)—C(═N+(R1b)(R1c))NR1dR1e, —C(═N+(R1b)(R1c))NR1dR1e, acyl, fatty acyl, benzyl, benzoyl, heteroaryl or trifluoroacetyl, —NHC1-18alkyl, —NHC6-16Aryl, —NH—C1-6alkyl-C6-10aryl, biotin, a sugar moiety or (poly)alkyleneglycol;
wherein each of R1a, R1b, R1c, R1d and R1e is independently selected from hydrogen or C1-4 alkyl (e.g. methyl, ethyl, propyl, butyl);
and any alkyl, formyl, acyl, fatty acyl, benzyl, benzoyl, heteroaryl or trifluoroacetyl, —NHC1-18alkyl, —NHC6-16Aryl, —NH—C1-6alkyl-C6-10aryl or (poly)alkyleneglycol may optionally be substituted with one or more groups selected from halogen, C1-6alkyl, C1-6haloalkyl or a sugar moiety;
L1 is absent or is:
*—(C═O)C1-16-alkylene-NH— where * denotes the point of attachment to Y or Z;
(C1-20)alkylene,
(C2-20)alkenylene,
(poly)alkyleneglycol;
wherein L1 is optionally substituted with one or more groups selected from oxo (═O), halogen, ═N and ═S;
Y is absent or is a peptide comprising from 1 to 16 amino acids;
wherein Y optionally comprises a (poly)alkyleneglycol linker in the peptide sequence;
Z is a peptide of the formula:
wherein:
X2 is selected from S#, Y#, K#, N# or H# (preferably X2 is selected from S#, Yn, N# or H#)
X3 is selected from S#, A#, P#, V# or T#,
X5 is selected from G#, A#;
wherein “#” indicates that the listed residue is independently the unmodified amino acid, a modified amino acid or a non-natural amino acid analogue;
and
R2 is NH2, NR2aH, NR2aR2b, OH or OR2a (preferably R2 is NH2, NR2aH, NR2aR2b, or OR2a);
wherein each of R2a and R2b if present are independently C1-6-alkyl (e.g. methyl, ethyl, propyl, butyl, pentyl or hexyl), C3-6-alkenyl, C6-16-aryl, C6-16-aryl-C1-6-alkyl, C1-6-alkylene-C6-16-aryl, or C1-6-haloalkyl, each of which may optionally be substituted with one or more groups selected from halogen, C1-6-alkyl, or C1-6-haloalkyl.

18 more elements

An insecticidal compound selected from:

(SEQ ID NO:
59)
Hy-DPKYKFSSWG-[NH2];
(SEQ ID NO:
60)
Hy-AKFSSWG-[NH2];
(SEQ ID NO:
61)
Hy-ARFSSWA-[NH2];
(SEQ ID NO:
62)
Hy-SKFNSWA-[NH2];
(SEQ ID NO:
63)
Hy-AKFSSWA-[NH2];
(SEQ ID NO:
64)
Hy-ARFNSWA-[NH2];
(SEQ ID NO:
65)
Hy-VPFNSWA-[NH2];
(SEQ ID NO:
66)
Hy-PIFSSWG-[NH2];
(SEQ ID NO:
67)
Hy-GPDFYAWG-[NH2];
(SEQ ID NO:
18)
Ac-KQrFH[Aib]WG-[NH2];
(SEQ ID NO:
19)
Ac-NSVVLGKKQrFH[Aib]WG-[NH2];
(SEQ ID NO:
20)
Ac-FH[Aib]WG-[NH2];
(SEQ ID NO:
21)
Ac-KQrFHsWG-[NH2];
(SEQ ID NO:
22)
Ac-FHsWG-[NH2];
(SEQ ID NO:
23)
NSVVLGKKQ[n-me-R]FH[n-me-S]WG-[NH2];
(SEQ ID NO:
68)
Ac-SKFN-Aib-WA-[NH2];
(SEQ ID NO:
69)
Ac-SK-[n-me-F]-N-(α-Me) Ser-WA-[NH2];
(SEQ ID NO:
70)
Ac-PA-[n-me-F]-SsWG-[NH2];
(SEQ ID NO:
71)
Hy-RQKTVFSSWG-[NH2];
(SEQ ID NO:
72)
Hy-PAFSSWG-[NH2];
(SEQ ID NO:
73)
Hy-ASDKHGRPKQTFSSWG-[NH2];
(SEQ ID NO:
107)
Hy-VRFSPWG-[NH2];
(SEQ ID NO:
108)
Hy-NFSPWG-[NH2];
(SEQ ID NO:
109)
Hy-KVKFSAWG-[NH2];
(SEQ ID NO:
110)
Hy-SFSPWG-[NH2];
(SEQ ID NO:
111)
Hy-FSPWG-[NH2];
(SEQ ID NO:
112)
Hy-YFSPWG-[NH2];
(SEQ ID NO:
113)
Hy-KVKFSVWG-[NH2];
(SEQ ID NO:
114)
Hy-KVKFSTWG-[NH2];
(SEQ ID NO:
74)
Ac-PA-[n-me-F]-S-βa-WG-[NH2];
(SEQ ID NO:
75)
Ac-PA-[n-me-F]-S-(α-Me)S-WG-[NH2];
(SEQ ID NO:
116)
Ava-FS-BA-WG-[NH2];
(SEQ ID NO:
117)
Ava-FS-Thz-WG-[NH2];
(SEQ ID NO:
92)
Hy-GPAFSSWG-[NH2];
(SEQ ID NO:
93)
Hy-AAAFNSWG-[NH2];
(SEQ ID NO:
94)
Hy-NAAFSSWG-[nh2];
(SEQ ID NO:
95)
Hy-NAAFNSWG-[NH2];
(SEQ ID NO:
96)
Hy-VPAFNSWG-[NH2];
(SEQ ID NO:
97)
Hy-TNTAFSSWG-[NH2];
(SEQ ID NO:
98)
Hy-PRFYSWG-[NH2];
(SEQ ID NO:
99)
Hy-GADFYAWG-[NH2];
(SEQ ID NO:
76)
Hy-DPAFNSWG-[NH2];
(SEQ ID NO:
77)
Hy-SSAFNSWG-[NH2];
(SEQ ID NO:
78)
Hy-RAFTSTGSSRSPAFSSWG-[NH2];
(SEQ ID NO:
79)
Hy-PASFSSWG-[NH2];
(SEQ ID NO:
80)
Hy-DAGFSSWG-[NH2];
(SEQ ID NO:
81)
Hy-SSGFSSWG-[NH2];
(SEQ ID NO:
82)
Hy-DPVFKSWG-[NH2];
(SEQ ID NO:
83)
Hy-DAAFSSWG-[NH2];
(SEQ ID NO:
84)
Hy-GSGFSSWG-[NH2];
(SEQ ID NO:
85)
Hy-DDDSDVSESGSKFSSWG-[NH2];
(SEQ ID NO:
86)
Hy-SFSSWG-[NH2];
(SEQ ID NO:
87)
Hy-GFSSWG-[NH2];
(SEQ ID NO:
88)
Hy-LDRSEGRVSKALFSSWG-[NH2];
(SEQ ID NO:
89)
Hy-WGQSSVGAVFSSWG-[NH2];
(SEQ ID NO:
90)
Hy-GAEFYSWG-[NH2];
(SEQ ID NO:
91)
Hy-FSSWG-[NH2];
or
(SEQ ID NO:
100)
[Ac]-SK[n-me-F]N[βAla]WA-[NH2];
or a salt or solvate thereof.

173 more elements

Dependencies are inferred from the claim text.

Facts

Application: 19/121,653Filed 23 Oct 2023
Priority: GB 2215797.825 Oct 2022
Published: 30 Jul 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07K 7/06
Linear peptides containing only normal peptide links: having 5 to 11 amino acids
A01N 25/02
Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by…
A01N 37/46
Containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton…
A01N 47/44
Containing —N=CX2 groups, e.g. isothiourea: guanidine; Derivatives thereof

Family

No related US applications are recorded in the indexed filing history.

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Abstract

An insecticidal compound having the formula (XX) below, or a salt or solvate thereof:

wherein:
R1 is hydrogen (which may be designated “H-” or “Hy-”), C1-4alkyl (e.g. methyl, ethyl, propyl, butyl), formyl, —N(R1a)—C(═N+(R1b)(R1c))NR1dR1e, —C(═N+(R1b)(R1c))NR1dR1e, acyl, fatty acyl, benzyl, benzoyl, heteroaryl or trifluoroacetyl, —NHC1-18alkyl, —NHC6-16Aryl, —NH—C1-6alkyl-C6-10aryl, biotin, a sugar moiety or (poly)alkyleneglycol, phosphate or sulphate;
wherein each of R1a, R1b, R1c, R1d and R1e is independently selected from hydrogen or C1-4 alkyl (e.g. methyl, ethyl, propyl, butyl);
and any alkyl, formyl, acyl, fatty acyl, benzyl, benzoyl, heteroaryl or trifluoroacetyl, —NHC1-18alkyl, —NHC6-16Aryl, —NH—C1-6alkyl-C6-10aryl or (poly)alkyleneglycol may optionally be substituted with one or more groups selected from halogen, C1-6alkyl, C1-6haloalkyl, a sugar moiety, phosphate or sulphate;
L1 is absent or is:
*—(C═O)C1-6-alkylene-NH— where * denotes the point of attachment to Y1, Y or Z;
(C1-20)alkylene,
(C2-20)alkenylene,
(poly)alkyleneglycol;
wherein L1 is optionally substituted with one or more groups selected from oxo (═O), halogen, ═N and ═S;
Y1 is absent or is a peptide comprising from 1 to 2 amino acids;
Y is absent or is a peptide comprising from 1 to 16 amino acids;
wherein Y optionally comprises a (poly)alkyleneglycol linker in the peptide sequence;
Y2 is absent or is a peptide comprising from 1 to 2 amino acids;
Z is a peptide of the formula:
wherein:
X2 is selected from S#, Y#, K#, N# or Hm;
X3 is selected from S#, A#, P#, V# or T#
X5 is selected from G#, A#;
wherein “#” indicates that the listed residue is independently the unmodified amino acid, a modified amino acid or a non-natural amino acid analogue;
R2 is NH2, NR2aH, NR2aR2b, OH or OR2a;
wherein each of R2a and R2b if present are independently C1-6-alkyl (e.g. methyl, ethyl, propyl, butyl, pentyl or hexyl), C3-6-alkenyl, C6-16-aryl, C6-16-aryl-C1-6-alkyl, C1-6-alkylene-C6-16-aryl, or C1-6 haloalkyl, each of which may optionally be substituted with one or more groups selected from halogen, C1-6-alkyl, or C1-6-haloalkyl.

19 more elements

Facts

Application

19/121,653Filed 23 Oct 2023

Priority

GB 2215797.825 Oct 2022

Published

30 Jul 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07K 7/06
Linear peptides containing only normal peptide links: having 5 to 11 amino acids
A01N 25/02
Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by…
A01N 37/46
Containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton…
A01N 47/44
Containing —N=CX2 groups, e.g. isothiourea: guanidine; Derivatives thereof