AU2016380868B2 - Anthelmintic depsipeptide compounds - Google Patents
Anthelmintic depsipeptide compounds Download PDFInfo
- Publication number
- AU2016380868B2 AU2016380868B2 AU2016380868A AU2016380868A AU2016380868B2 AU 2016380868 B2 AU2016380868 B2 AU 2016380868B2 AU 2016380868 A AU2016380868 A AU 2016380868A AU 2016380868 A AU2016380868 A AU 2016380868A AU 2016380868 B2 AU2016380868 B2 AU 2016380868B2
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- Prior art keywords
- independently
- substituted
- alkyl
- halogen
- haloalkyl
- Prior art date
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- 230000000507 anthelmentic effect Effects 0.000 title claims description 66
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical class O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 title abstract description 15
- 108010002156 Depsipeptides Proteins 0.000 claims abstract description 90
- 241001465754 Metazoa Species 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 14
- -1 thioamido Chemical group 0.000 claims description 514
- 229910052736 halogen Inorganic materials 0.000 claims description 313
- 125000001188 haloalkyl group Chemical group 0.000 claims description 288
- 125000000217 alkyl group Chemical group 0.000 claims description 287
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 262
- 125000004414 alkyl thio group Chemical group 0.000 claims description 260
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 260
- 125000003545 alkoxy group Chemical group 0.000 claims description 259
- 125000003282 alkyl amino group Chemical group 0.000 claims description 256
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 255
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 253
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 223
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 222
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 222
- 125000004043 oxo group Chemical group O=* 0.000 claims description 222
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 219
- 125000000623 heterocyclic group Chemical group 0.000 claims description 215
- 125000005843 halogen group Chemical group 0.000 claims description 199
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 191
- 150000002367 halogens Chemical group 0.000 claims description 182
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 173
- 125000001424 substituent group Chemical group 0.000 claims description 156
- 229910052739 hydrogen Inorganic materials 0.000 claims description 143
- 239000001257 hydrogen Substances 0.000 claims description 143
- 125000001072 heteroaryl group Chemical group 0.000 claims description 138
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 135
- 125000003118 aryl group Chemical group 0.000 claims description 126
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 106
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 103
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 74
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 72
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 67
- 125000002837 carbocyclic group Chemical group 0.000 claims description 60
- 125000003342 alkenyl group Chemical group 0.000 claims description 54
- 125000000304 alkynyl group Chemical group 0.000 claims description 51
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 44
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 41
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 41
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 33
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 33
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 31
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 21
- 208000030852 Parasitic disease Diseases 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
- 230000002265 prevention Effects 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 15
- 241000244206 Nematoda Species 0.000 claims description 14
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 14
- 229910052705 radium Inorganic materials 0.000 claims description 13
- 229910052701 rubidium Inorganic materials 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 11
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 11
- 230000003071 parasitic effect Effects 0.000 claims description 11
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
- 125000002971 oxazolyl group Chemical group 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 claims description 9
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 9
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 claims description 9
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 9
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 9
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 9
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000002346 iodo group Chemical group I* 0.000 claims description 7
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003566 oxetanyl group Chemical group 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- 125000006088 2-oxoazepinyl group Chemical group 0.000 claims description 3
- 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 claims description 3
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims description 3
- 125000006087 2-oxopyrrolodinyl group Chemical group 0.000 claims description 3
- 125000005986 4-piperidonyl group Chemical group 0.000 claims description 3
- 125000002785 azepinyl group Chemical group 0.000 claims description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 3
- 125000003971 isoxazolinyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
- 230000000590 parasiticidal effect Effects 0.000 claims description 3
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 3
- 125000006092 tetrahydro-1,1-dioxothienyl group Chemical group 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 claims description 3
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 claims description 3
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000004069 aziridinyl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 244000045947 parasite Species 0.000 abstract description 17
- 241000124008 Mammalia Species 0.000 abstract description 12
- 206010061217 Infestation Diseases 0.000 abstract description 11
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 101
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 64
- 125000003627 8 membered carbocyclic group Chemical group 0.000 description 54
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 52
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 30
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 30
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical group C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 description 28
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 23
- KHEPSBKTSMKGQV-UHFFFAOYSA-N 3-[4-[2-(4-piperidin-4-ylanilino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical group N1CCC(CC1)C1=CC=C(C=C1)NC=1N=C(C2=C(N=1)NC=C2)C=1C=NN(C=1)CCC#N KHEPSBKTSMKGQV-UHFFFAOYSA-N 0.000 description 21
- 241000002163 Mesapamea fractilinea Species 0.000 description 20
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 20
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 20
- 208000015181 infectious disease Diseases 0.000 description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
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- 229910052727 yttrium Inorganic materials 0.000 description 16
- 125000004011 3 membered carbocyclic group Chemical group 0.000 description 12
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- 125000001845 4 membered carbocyclic group Chemical group 0.000 description 12
- 125000001963 4 membered heterocyclic group Chemical group 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 10
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 10
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 10
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 10
- 241000282472 Canis lupus familiaris Species 0.000 description 10
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 10
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000001041 indolyl group Chemical group 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 10
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 10
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 10
- 150000003536 tetrazoles Chemical class 0.000 description 10
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 10
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 9
- 125000004610 3,4-dihydro-4-oxo-quinazolinyl group Chemical group O=C1NC(=NC2=CC=CC=C12)* 0.000 description 8
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 229960002957 praziquantel Drugs 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 229940052423 profender Drugs 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 1
- 229960002245 selamectin Drugs 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/15—Depsipeptides; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2020200854A AU2020200854B2 (en) | 2015-12-28 | 2020-02-06 | Anthelmintic depsipeptide compounds |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562272040P | 2015-12-28 | 2015-12-28 | |
| US62/272,040 | 2015-12-28 | ||
| PCT/US2016/066497 WO2017116702A1 (en) | 2015-12-28 | 2016-12-14 | Anthelmintic depsipeptide compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2020200854A Division AU2020200854B2 (en) | 2015-12-28 | 2020-02-06 | Anthelmintic depsipeptide compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2016380868A1 AU2016380868A1 (en) | 2018-07-19 |
| AU2016380868B2 true AU2016380868B2 (en) | 2019-11-28 |
Family
ID=57868331
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016380868A Ceased AU2016380868B2 (en) | 2015-12-28 | 2016-12-14 | Anthelmintic depsipeptide compounds |
| AU2020200854A Ceased AU2020200854B2 (en) | 2015-12-28 | 2020-02-06 | Anthelmintic depsipeptide compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2020200854A Ceased AU2020200854B2 (en) | 2015-12-28 | 2020-02-06 | Anthelmintic depsipeptide compounds |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US10344056B2 (enExample) |
| EP (1) | EP3397638B1 (enExample) |
| JP (1) | JP6943859B2 (enExample) |
| KR (2) | KR20220003663A (enExample) |
| CN (1) | CN108699052B (enExample) |
| AR (1) | AR107249A1 (enExample) |
| AU (2) | AU2016380868B2 (enExample) |
| BR (1) | BR112018013369A2 (enExample) |
| CA (1) | CA3009867C (enExample) |
| CL (1) | CL2018001744A1 (enExample) |
| CO (1) | CO2018006527A2 (enExample) |
| HK (1) | HK1255391A1 (enExample) |
| HU (1) | HUE065907T2 (enExample) |
| IL (1) | IL260262B2 (enExample) |
| MX (1) | MX2018007948A (enExample) |
| MY (1) | MY194716A (enExample) |
| NZ (1) | NZ743913A (enExample) |
| PH (1) | PH12018501367B1 (enExample) |
| RU (2) | RU2715556C2 (enExample) |
| SG (1) | SG11201805368YA (enExample) |
| TW (1) | TWI787165B (enExample) |
| UY (1) | UY37050A (enExample) |
| WO (1) | WO2017116702A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ737610A (en) * | 2015-05-20 | 2023-07-28 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic depsipeptide compounds |
| CN108699052B (zh) | 2015-12-28 | 2022-04-29 | 勃林格殷格翰动物保健美国公司 | 驱虫缩酚酸肽化合物 |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| AU2017361099A1 (en) | 2016-11-16 | 2019-06-06 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| EP3579696B1 (en) | 2017-02-08 | 2023-06-28 | Boehringer Ingelheim Animal Health USA Inc. | In vivo model for parasitic worm infection and methods for evaluating antiparasitic compounds, including compounds active against canine heartworm |
| EP3480195A1 (en) | 2017-11-07 | 2019-05-08 | Bayer Animal Health GmbH | Method for the synthesis of cyclic depsipeptides |
| MX2020004702A (es) * | 2017-11-07 | 2020-11-06 | Bayer Animal Health Gmbh | Metodo para la sintesis de depsipeptidos ciclicos. |
| BR112020010399A2 (pt) * | 2017-11-29 | 2020-11-24 | Zoetis Services Llc | depsipeptídeos endoparasitários |
| WO2019157241A1 (en) | 2018-02-08 | 2019-08-15 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof |
| EP3908330A1 (en) | 2019-01-10 | 2021-11-17 | Zoetis Services LLC | Anthelmintic laboratory animal model for heartworm |
| CN119285648A (zh) | 2019-03-19 | 2025-01-10 | 勃林格殷格翰动物保健有限公司 | 驱虫的氮杂-苯并噻吩和氮杂-苯并呋喃化合物 |
| WO2021178834A1 (en) * | 2020-03-06 | 2021-09-10 | LifeMax Laboratories, Inc. | Topical pharmaceutical formulations of a cyclic depsipeptide |
| PH12022553222A1 (en) | 2020-05-29 | 2024-02-12 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic heterocyclic compounds |
| CN116897044A (zh) | 2020-12-21 | 2023-10-17 | 勃林格殷格翰动物保健有限公司 | 包含异噁唑啉化合物的杀寄生虫环 |
| JP2025507585A (ja) | 2022-02-17 | 2025-03-21 | ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハー | 流体製品メーラーを提供する方法及びシステム |
| WO2025057117A1 (en) * | 2023-09-15 | 2025-03-20 | Animol Discovery, Inc. | Antiparasitic cyclic depsipeptides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0626375A1 (de) * | 1993-05-26 | 1994-11-30 | Bayer Ag | Octacylodepsideptide mit endoparasitizider Wirkung |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO176766C (no) | 1989-02-07 | 1995-05-24 | Meiji Seika Kaisha | Fremgangsmåte for fremstilling av en forbindelse med anthelmintaktivitet |
| DE69331414T2 (de) | 1992-03-17 | 2002-08-08 | Fujisawa Pharmaceutical Co., Ltd. | Depsipeptide, herstellung und anwendung |
| WO1994019334A1 (fr) | 1993-02-19 | 1994-09-01 | Meiji Seika Kaisha, Ltd. | Derive du pf 1022 utilise comme depsipeptide cyclqiue |
| DE4317432A1 (de) | 1993-05-26 | 1994-12-01 | Bayer Ag | Octacyclodepsipeptide mit endoparasitizider Wirkung |
| ATE214379T1 (de) | 1993-09-06 | 2002-03-15 | Fujisawa Pharmaceutical Co | Cyclodepsipeptide |
| SE9303657D0 (sv) | 1993-11-05 | 1993-11-05 | Astra Ab | Short-acting dihydropyridines |
| DE4400464A1 (de) * | 1994-01-11 | 1995-07-13 | Bayer Ag | Endoparasitizide Mittel |
| DE4437198A1 (de) | 1994-10-18 | 1996-04-25 | Bayer Ag | Verfahren zur Sulfonylierung, Sulfenylierung und Phosphorylierung von cyclischen Depsipeptiden |
| DE19520275A1 (de) | 1995-06-02 | 1996-12-05 | Bayer Ag | Endoparasitizide Mittel |
| CZ295705B6 (cs) | 1995-09-22 | 2005-10-12 | Bayer Aktiengesellschaft | Cyklodepsipeptidové deriváty sloučeniny PF1022 a farmaceutický prostředek s jejich obsahem |
| DE69721055T2 (de) | 1996-10-07 | 2004-02-19 | Fujisawa Pharmaceutical Co., Ltd. | Verfahren zur herstellung von depsipeptiden und zwischenprodukten davon |
| DE19713626A1 (de) | 1997-04-02 | 1998-10-08 | Bayer Ag | Neue Thiodepsipeptide zur Bekämpfung von Endoparasiten und ein einfaches Verfahren zu ihrer Herstellung |
| WO1998055469A1 (de) | 1997-06-04 | 1998-12-10 | Bayer Aktiengesellschaft | Desoxycyclodepsipeptide und ihre verwendung zur bekämpfung von endoparasiten |
| DE19811559A1 (de) | 1998-03-17 | 1999-09-23 | Bayer Ag | Cyclooctadepsipeptide |
| DE19828043A1 (de) | 1998-06-24 | 1999-12-30 | Bayer Ag | Ektoparasitizide Mittel |
| DE19921887A1 (de) * | 1999-05-12 | 2000-11-16 | Bayer Ag | Endoparasitizide Mittel |
| DE19962147A1 (de) | 1999-12-22 | 2001-06-28 | Bayer Ag | Schädlingsbekämpfungsmittel / PF 1022-221 |
| DE19962145A1 (de) | 1999-12-22 | 2001-06-28 | Bayer Ag | Schädlingsbekämpfungsmittel/Depsipeptide |
| DE10008128A1 (de) | 2000-02-22 | 2001-08-23 | Bayer Ag | Endoparasitizide Mittel |
| DE10031044A1 (de) | 2000-06-26 | 2002-01-03 | Bayer Ag | Endoparasitizide Mittel zur freiwilligen oralen Aufnahme durch Tiere |
| DE10104362A1 (de) | 2001-02-01 | 2002-08-08 | Bayer Ag | Kristallmodifikation eines cyclischen Depsipeptids mit besserer Wirksamkeit |
| UY26592A1 (es) | 2001-02-20 | 2001-09-28 | Bayer Ag | Agentes endoparasiticidas |
| US6893652B2 (en) * | 2001-08-27 | 2005-05-17 | Wyeth | Endoparasiticidal gel composition |
| US20040236191A1 (en) | 2003-05-19 | 2004-11-25 | Poliska Steven A. | System and method for identifying and labeling livestock products, and managing data associated with those products |
| DE10358525A1 (de) | 2003-12-13 | 2005-07-07 | Bayer Healthcare Ag | Endoparasitizide Mittel zur topischen Applikation |
| DE602005023371D1 (de) | 2004-02-27 | 2010-10-21 | Ic Services | Verfahren und Satz zum Identifizieren von Tieren |
| DE102004055316A1 (de) | 2004-11-16 | 2006-05-18 | Bayer Healthcare Ag | Verhinderung vertikaler Endoparasiten-Infektionen |
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| KR101002530B1 (ko) | 2009-02-18 | 2010-12-17 | 삼성에스디아이 주식회사 | 알에프아이디 통신 장치 |
| EP2509967B1 (en) | 2009-12-11 | 2016-02-17 | Bayer Intellectual Property GmbH | Novel 24-membered cyclooctadepsipeptides from fungal strains and their use as anthelmintics or endoparasiticides |
| WO2012028556A1 (en) | 2010-08-31 | 2012-03-08 | Bayer Animal Health Gmbh | Macrocyclic lactones and their use and their combinations with other active substances |
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| RU2015100521A (ru) | 2012-06-13 | 2016-08-10 | Мейдзи Сейка Фарма Ко., Лтд. | Новые циклические депсипептидные производные и средства для борьбы с вредными организмами, включающие такие производные |
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| NZ737610A (en) * | 2015-05-20 | 2023-07-28 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic depsipeptide compounds |
| CN108699052B (zh) | 2015-12-28 | 2022-04-29 | 勃林格殷格翰动物保健美国公司 | 驱虫缩酚酸肽化合物 |
| AU2017361099A1 (en) | 2016-11-16 | 2019-06-06 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
-
2016
- 2016-12-14 CN CN201680082548.2A patent/CN108699052B/zh not_active Expired - Fee Related
- 2016-12-14 KR KR1020217043332A patent/KR20220003663A/ko not_active Abandoned
- 2016-12-14 RU RU2018127195A patent/RU2715556C2/ru active
- 2016-12-14 US US15/378,219 patent/US10344056B2/en active Active
- 2016-12-14 HK HK18114530.8A patent/HK1255391A1/zh unknown
- 2016-12-14 RU RU2020107484A patent/RU2020107484A/ru unknown
- 2016-12-14 HU HUE16829348A patent/HUE065907T2/hu unknown
- 2016-12-14 SG SG11201805368YA patent/SG11201805368YA/en unknown
- 2016-12-14 AU AU2016380868A patent/AU2016380868B2/en not_active Ceased
- 2016-12-14 WO PCT/US2016/066497 patent/WO2017116702A1/en not_active Ceased
- 2016-12-14 NZ NZ743913A patent/NZ743913A/en not_active IP Right Cessation
- 2016-12-14 EP EP16829348.8A patent/EP3397638B1/en active Active
- 2016-12-14 PH PH1/2018/501367A patent/PH12018501367B1/en unknown
- 2016-12-14 MX MX2018007948A patent/MX2018007948A/es unknown
- 2016-12-14 MY MYPI2018001112A patent/MY194716A/en unknown
- 2016-12-14 BR BR112018013369-8A patent/BR112018013369A2/pt not_active Application Discontinuation
- 2016-12-14 JP JP2018534122A patent/JP6943859B2/ja not_active Expired - Fee Related
- 2016-12-14 CA CA3009867A patent/CA3009867C/en active Active
- 2016-12-14 KR KR1020187021726A patent/KR102427124B1/ko active Active
- 2016-12-26 UY UY0001037050A patent/UY37050A/es not_active Application Discontinuation
- 2016-12-28 TW TW105143547A patent/TWI787165B/zh not_active IP Right Cessation
- 2016-12-28 AR ARP160104061A patent/AR107249A1/es not_active Application Discontinuation
-
2018
- 2018-06-25 CL CL2018001744A patent/CL2018001744A1/es unknown
- 2018-06-25 CO CONC2018/0006527A patent/CO2018006527A2/es unknown
- 2018-06-25 IL IL260262A patent/IL260262B2/en unknown
-
2019
- 2019-04-23 US US16/392,412 patent/US11230571B2/en active Active
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2020
- 2020-02-06 AU AU2020200854A patent/AU2020200854B2/en not_active Ceased
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2021
- 2021-12-08 US US17/643,251 patent/US12018048B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0626375A1 (de) * | 1993-05-26 | 1994-11-30 | Bayer Ag | Octacylodepsideptide mit endoparasitizider Wirkung |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC. Free format text: FORMER APPLICANT(S): MERIAL, INC. |
|
| FGA | Letters patent sealed or granted (standard patent) |