NZ785162B2 - Antiparasitic isoxazoline compounds, long-acting injectable formulations comprising them, methods and uses thereof - Google Patents
Antiparasitic isoxazoline compounds, long-acting injectable formulations comprising them, methods and uses thereof Download PDFInfo
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- NZ785162B2 NZ785162B2 NZ785162A NZ78516217A NZ785162B2 NZ 785162 B2 NZ785162 B2 NZ 785162B2 NZ 785162 A NZ785162 A NZ 785162A NZ 78516217 A NZ78516217 A NZ 78516217A NZ 785162 B2 NZ785162 B2 NZ 785162B2
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- New Zealand
- Prior art keywords
- long
- composition according
- acting
- solvents
- glycerol
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- 239000007972 injectable composition Substances 0.000 title claims abstract 4
- 238000000034 method Methods 0.000 title claims 4
- 150000002547 isoxazolines Chemical class 0.000 title abstract 2
- 230000002141 anti-parasite Effects 0.000 title 1
- 239000003096 antiparasitic agent Substances 0.000 title 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000005676 cyclic carbonates Chemical class 0.000 claims abstract 6
- 229940074076 glycerol formal Drugs 0.000 claims abstract 6
- 239000007788 liquid Substances 0.000 claims abstract 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract 6
- 206010061217 Infestation Diseases 0.000 claims abstract 5
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims abstract 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims abstract 4
- 230000002265 prevention Effects 0.000 claims abstract 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract 4
- -1 glycerol ester Chemical class 0.000 claims abstract 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract 2
- 208000030852 Parasitic disease Diseases 0.000 claims abstract 2
- 229960002903 benzyl benzoate Drugs 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract 2
- 229940116333 ethyl lactate Drugs 0.000 claims abstract 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims 23
- 239000002904 solvent Substances 0.000 claims 8
- 229920001223 polyethylene glycol Polymers 0.000 claims 5
- 239000003937 drug carrier Substances 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 230000003071 parasitic effect Effects 0.000 claims 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 241000238876 Acari Species 0.000 claims 1
- 241000283690 Bos taurus Species 0.000 claims 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims 1
- 241000282326 Felis catus Species 0.000 claims 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 claims 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 claims 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940093499 ethyl acetate Drugs 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 244000045947 parasite Species 0.000 claims 1
- KISFEBPWFCGRGN-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)ethyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl KISFEBPWFCGRGN-UHFFFAOYSA-M 0.000 claims 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 2
- 230000000590 parasiticidal effect Effects 0.000 abstract 1
Abstract
This invention relates to a long-acting injectable composition for the treatment or prevention of a parasitic infection or infestation comprising a compound of formula (Ie) and a carrier selected from one or more of ethanol, 1-propanol, isopropanol, a glycol ether, liquid PEG, a triglyceride, propylene glycol, glycerol, a glycerol ester, benzyl benzoate, ethyl acetate, a cyclic carbonate, 2-pyrrolidone, N-methylpyrrolidone, dimethyl isosorbide (DMI), dimethylacetamide (DMA), dimethyl formamide (DMF), caprolactam, glycerol formal, acetone, dimethylsulfoxide (DMSO) and ethyl lactate. Also disclosed are further parasiticidal long-acting injectable compositions and new isoxazoline compounds.
Claims (18)
1. A long-acting injectable composition for the treatment or prevention of a parasitic infection or infestation, said composition comprising an effective amount of an isoxazoline compound of formula (Ie): or a pharmaceutically or agriculturally acceptable salt thereof; and a pharmaceutically acceptable carrier, wherein the ceutically acceptable carrier is a single or blend of solvents ed from the group consisting of ethanol, 1-propanol, isopropanol, a glycol ether, liquid PEG, a triglyceride, propylene glycol, glycerol, a glycerol ester, a cyclic carbonate, 2-pyrrolidone, N-methylpyrrolidone, dimethyl isosorbide (DMI), dimethylacetamide (DMA), dimethyl formamide (DMF), actam, glycerol formal, acetone, dimethylsulfoxide (DMSO), ethyl acetate, ethyl lactate, and benzyl benzoate, or a e thereof.
2. The long-acting composition according to claim 1, wherein the pharmaceutically acceptable carrier ses one or more solvents selected from the group consisting of liquid PEG, a ceride, a cyclic carbonate, glycerol formal, and propylene glycol, or a mixture thereof.
3. The long-acting ition according to claim 1 or claim 2, wherein the liquid PEG is selected from the group ting of PEG 200, PEG 300, and PEG 400, or a mixture thereof.
4. The long-acting composition according to any one of claims 1 to 3, wherein the triglyceride is a triglyceride of onated plant fatty acids with chain lengths of C8 to
5. The long-acting composition according to any one of claims 1 to 4, n the cyclic carbonate is selected from the group consisting of ethylene carbonate and propylene carbonate, or a mixture thereof.
6. The long-acting composition according to any one of claims 1 to 5, wherein the isoxazoline active agent is ed in an enantiomer.
7. The cting composition according to any one of claims 1 to 6, wherein isoxazoline active agent is a compound of formula (S)-Ie: (S)-Ie or a pharmaceutically or agriculturally acceptable salt f.
8. The long-acting composition according to any one of claims 1 to 7, wherein the pharmaceutically able carrier ses a blend of solvents.
9. The long-acting composition according to claim 8, wherein the blend of solvents comprises glycerol formal.
10. The long-acting composition according to claim 9, wherein the blend of solvents comprises glycerol formal and one or more solvents selected from the group consisting of liquid PEG, propylene glycol, and glycerol.
11. The long-acting composition according to claim 10, n the blend of solvents ses glycerol formal and one or more solvents selected from the group consisting of a liquid PEG and propylene glycol.
12. The long-acting composition according to any one of claims 1 to 7, wherein the pharmaceutically acceptable carrier comprises a cyclic carbonate.
13. The long-acting composition according to claim 12, wherein the cyclic carbonate is propylene carbonate.
14. A method for the treatment and/or tion of a parasitic infestation or infection on or in a non-human animal comprising administering to the non-human animal a longacting composition according to any one of claims 1 to 13.
15. Use of a long-acting composition according to any one of claims 1 to 13 for the treatment and/or prevention of a parasitic infestation or infection on or in a non-human animal.
16. The method or use ing to claim 14 or claim 15, wherein the non-human animal is a dog, a cat, an ovine or a bovine.
17. The method or use according to any one of claims 14 to 16, wherein the parasites are fleas or ticks.
18. Use of a cting composition according to any one of claims 1 to 13, in the manufacture of a medicament for the treatment and/or prevention of a tic infestation or infection.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662299333P | 2016-02-24 | 2016-02-24 | |
| US201662379348P | 2016-08-25 | 2016-08-25 | |
| NZ755538A NZ755538B2 (en) | 2017-02-24 | Antiparasitic isoxazoline compounds, long-acting injectable formulations comprising them, methods and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ785162A NZ785162A (en) | 2024-08-30 |
| NZ785162B2 true NZ785162B2 (en) | 2024-12-03 |
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