RU2715556C2 - Противогельминтные депсипептидные соединения - Google Patents
Противогельминтные депсипептидные соединения Download PDFInfo
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- RU2715556C2 RU2715556C2 RU2018127195A RU2018127195A RU2715556C2 RU 2715556 C2 RU2715556 C2 RU 2715556C2 RU 2018127195 A RU2018127195 A RU 2018127195A RU 2018127195 A RU2018127195 A RU 2018127195A RU 2715556 C2 RU2715556 C2 RU 2715556C2
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- 230000000507 anthelmentic effect Effects 0.000 title claims description 34
- 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 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 108010002156 Depsipeptides Proteins 0.000 claims abstract description 61
- 241001465754 Metazoa Species 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 12
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 506
- 125000005843 halogen group Chemical group 0.000 claims description 468
- 229910052736 halogen Inorganic materials 0.000 claims description 372
- 125000000623 heterocyclic group Chemical group 0.000 claims description 278
- 125000000217 alkyl group Chemical group 0.000 claims description 205
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 161
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 155
- 125000003277 amino group Chemical group 0.000 claims description 151
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 142
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 142
- 125000001424 substituent group Chemical group 0.000 claims description 142
- 125000002837 carbocyclic group Chemical group 0.000 claims description 130
- 125000001072 heteroaryl group Chemical group 0.000 claims description 121
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 93
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 89
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 88
- 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 86
- 125000001153 fluoro group Chemical group F* 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 75
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 71
- 150000002367 halogens Chemical class 0.000 claims description 68
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 64
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 54
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 36
- 230000015572 biosynthetic process Effects 0.000 claims description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 208000015181 infectious disease Diseases 0.000 claims description 26
- 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
- 125000002757 morpholinyl group Chemical group 0.000 claims description 19
- 125000003386 piperidinyl group Chemical group 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 208000030852 Parasitic disease Diseases 0.000 claims description 15
- 125000002541 furyl group Chemical group 0.000 claims description 15
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 15
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003566 oxetanyl 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
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
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- 125000003971 isoxazolinyl group Chemical group 0.000 claims description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 244000045947 parasite Species 0.000 abstract description 17
- 241000124008 Mammalia Species 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 233
- 125000003545 alkoxy group Chemical group 0.000 description 219
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 214
- 125000004414 alkyl thio group Chemical group 0.000 description 211
- 125000003282 alkyl amino group Chemical group 0.000 description 205
- 125000004438 haloalkoxy group Chemical group 0.000 description 202
- 125000004995 haloalkylthio group Chemical group 0.000 description 202
- 125000004663 dialkyl amino group Chemical group 0.000 description 194
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 182
- 125000004043 oxo group Chemical group O=* 0.000 description 178
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 172
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 170
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 155
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 152
- 125000001188 haloalkyl group Chemical group 0.000 description 125
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 124
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 72
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 62
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 57
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 51
- 125000003342 alkenyl group Chemical group 0.000 description 47
- 125000000304 alkynyl group Chemical group 0.000 description 43
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 34
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 32
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 32
- 125000000262 haloalkenyl group Chemical group 0.000 description 31
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 31
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 30
- 125000000232 haloalkynyl group Chemical group 0.000 description 29
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 28
- 125000004404 heteroalkyl group Chemical group 0.000 description 23
- 229920002554 vinyl polymer Polymers 0.000 description 21
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 18
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 17
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 17
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 17
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 17
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 17
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 16
- 244000079386 endoparasite Species 0.000 description 16
- 125000001041 indolyl group Chemical group 0.000 description 16
- 229930192474 thiophene Natural products 0.000 description 16
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 15
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 15
- 150000003852 triazoles Chemical class 0.000 description 15
- 125000004610 3,4-dihydro-4-oxo-quinazolinyl group Chemical group O=C1NC(=NC2=CC=CC=C12)* 0.000 description 14
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 14
- 235000010290 biphenyl Nutrition 0.000 description 14
- 239000004305 biphenyl Substances 0.000 description 14
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 description 14
- 125000004615 furo[2,3-b]pyridinyl group Chemical group O1C(=CC=2C1=NC=CC2)* 0.000 description 14
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 14
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- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 13
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 description 13
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- 125000004011 3 membered carbocyclic group Chemical group 0.000 description 12
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- 125000006086 furo[3,2-b]pyridinyl] group Chemical group 0.000 description 10
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
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- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 7
- YJNUXGPXJFAUQJ-LYWANRAQSA-N PF1022A Chemical compound C([C@@H]1C(=O)N(C)[C@H](C(O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](CC=2C=CC=CC=2)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O1)=O)CC(C)C)C1=CC=CC=C1 YJNUXGPXJFAUQJ-LYWANRAQSA-N 0.000 description 7
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005945 imidazopyridyl group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 229960002418 ivermectin Drugs 0.000 description 1
- 230000007653 larval development Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229960004330 melarsomine dihydrochloride Drugs 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- CKVMAPHTVCTEMM-ALPQRHTBSA-N milbemycin oxime Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\2)O)C[C@H]4C1.C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\1)O)C[C@H]4C2 CKVMAPHTVCTEMM-ALPQRHTBSA-N 0.000 description 1
- 229940099245 milbemycin oxime Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 description 1
- 229960004816 moxidectin Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
- 125000006099 n-pentyl sulfinyl group Chemical group 0.000 description 1
- 125000006129 n-pentyl sulfonyl group Chemical group 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 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
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 230000000590 parasiticidal effect Effects 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
- VJKGUHZEQQUQNR-UHFFFAOYSA-N phenyl 2-hydroxypropanoate Chemical group CC(O)C(=O)OC1=CC=CC=C1 VJKGUHZEQQUQNR-UHFFFAOYSA-N 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
- 235000021317 phosphate Nutrition 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
- 238000009374 poultry farming Methods 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
- 230000003449 preventive effect Effects 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000033458 reproduction Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 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
- 230000014639 sexual reproduction Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- 150000003527 tetrahydropyrans Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000009466 transformation 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
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)
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 |
|---|---|---|---|
| RU2020107484A Division RU2020107484A (ru) | 2015-12-28 | 2016-12-14 | Противогельминтные депсипептидные соединения |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2018127195A RU2018127195A (ru) | 2020-01-30 |
| RU2018127195A3 RU2018127195A3 (enExample) | 2020-01-30 |
| RU2715556C2 true RU2715556C2 (ru) | 2020-03-02 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018127195A RU2715556C2 (ru) | 2015-12-28 | 2016-12-14 | Противогельминтные депсипептидные соединения |
| RU2020107484A RU2020107484A (ru) | 2015-12-28 | 2016-12-14 | Противогельминтные депсипептидные соединения |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2020107484A RU2020107484A (ru) | 2015-12-28 | 2016-12-14 | Противогельминтные депсипептидные соединения |
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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0626375A1 (de) * | 1993-05-26 | 1994-11-30 | Bayer Ag | Octacylodepsideptide mit endoparasitizider Wirkung |
| EP0662326A2 (de) * | 1994-01-11 | 1995-07-12 | Bayer Ag | Endoparasitizide Mittel die Praziquantel und Epsiprantel enthalten |
| RU2250779C2 (ru) * | 1999-05-12 | 2005-04-27 | Байер Акциенгезельшафт | Эндопаразитицидное средство |
Family Cites Families (42)
| 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 |
| 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 |
| 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 |
| US20060202835A1 (en) | 2005-02-25 | 2006-09-14 | Osborne Industries, Inc. | Dual frequency identification device |
| DE102008022520A1 (de) | 2008-05-07 | 2009-11-12 | Bayer Animal Health Gmbh | Feste Arzneimittelformulierung mit verzögerter Freisetzung |
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