RU2707298C2 - Противогельминтные депсипептидные соединения - Google Patents
Противогельминтные депсипептидные соединения Download PDFInfo
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- RU2707298C2 RU2707298C2 RU2017144495A RU2017144495A RU2707298C2 RU 2707298 C2 RU2707298 C2 RU 2707298C2 RU 2017144495 A RU2017144495 A RU 2017144495A RU 2017144495 A RU2017144495 A RU 2017144495A RU 2707298 C2 RU2707298 C2 RU 2707298C2
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- alkyl
- group
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- independently
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- 230000000507 anthelmentic effect Effects 0.000 title claims description 53
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 158
- 108010002156 Depsipeptides Proteins 0.000 claims abstract description 72
- 244000045947 parasite Species 0.000 claims abstract description 20
- 241000124008 Mammalia Species 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 274
- 150000002367 halogens Chemical class 0.000 claims description 231
- 125000000217 alkyl group Chemical group 0.000 claims description 208
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 196
- 125000001424 substituent group Chemical group 0.000 claims description 184
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 183
- 125000001072 heteroaryl group Chemical group 0.000 claims description 162
- 125000000623 heterocyclic group Chemical group 0.000 claims description 159
- 125000003277 amino group Chemical group 0.000 claims description 143
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 139
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 121
- 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 115
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 84
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 76
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
- 125000004076 pyridyl group Chemical group 0.000 claims description 61
- 125000005843 halogen group Chemical group 0.000 claims description 55
- 125000002757 morpholinyl group Chemical group 0.000 claims description 54
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 54
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 52
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 26
- 208000015181 infectious disease Diseases 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 208000030852 Parasitic disease Diseases 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 239000005660 Abamectin Substances 0.000 claims 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[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 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims 1
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 claims 1
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 206010061217 Infestation Diseases 0.000 abstract 1
- 210000004209 hair Anatomy 0.000 abstract 1
- 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 3041
- -1 depsipeptide compound Chemical class 0.000 description 121
- 125000003545 alkoxy group Chemical group 0.000 description 94
- 125000003282 alkyl amino group Chemical group 0.000 description 93
- 125000004995 haloalkylthio group Chemical group 0.000 description 92
- 125000004414 alkyl thio group Chemical group 0.000 description 91
- 125000004663 dialkyl amino group Chemical group 0.000 description 91
- 125000004438 haloalkoxy group Chemical group 0.000 description 91
- 125000003118 aryl group Chemical group 0.000 description 87
- 239000004305 biphenyl Substances 0.000 description 68
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 66
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 58
- 125000003342 alkenyl group Chemical group 0.000 description 56
- 125000000304 alkynyl group Chemical group 0.000 description 54
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 54
- 125000003386 piperidinyl group Chemical group 0.000 description 51
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 50
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 description 50
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 50
- 125000001188 haloalkyl group Chemical group 0.000 description 49
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 49
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 46
- 125000000262 haloalkenyl group Chemical group 0.000 description 43
- 125000000232 haloalkynyl group Chemical group 0.000 description 41
- 125000003373 pyrazinyl group Chemical group 0.000 description 35
- 125000002098 pyridazinyl group Chemical group 0.000 description 35
- 125000000714 pyrimidinyl group Chemical group 0.000 description 35
- 125000004404 heteroalkyl group Chemical group 0.000 description 34
- 125000000168 pyrrolyl group Chemical group 0.000 description 32
- 125000002541 furyl group Chemical group 0.000 description 31
- 229920000728 polyester Polymers 0.000 description 31
- 125000002883 imidazolyl group Chemical group 0.000 description 30
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 30
- 125000001544 thienyl group Chemical group 0.000 description 30
- 125000003226 pyrazolyl group Chemical group 0.000 description 29
- 125000002971 oxazolyl group Chemical group 0.000 description 28
- 125000001786 isothiazolyl group Chemical group 0.000 description 27
- 125000004306 triazinyl group Chemical group 0.000 description 27
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 22
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 22
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 21
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 20
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 19
- 125000004043 oxo group Chemical group O=* 0.000 description 19
- 244000079386 endoparasite Species 0.000 description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 14
- 241000282472 Canis lupus familiaris Species 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 244000000013 helminth Species 0.000 description 13
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 12
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 12
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 230000000747 cardiac effect Effects 0.000 description 11
- 241000243988 Dirofilaria immitis Species 0.000 description 10
- 229940099686 dirofilaria immitis Drugs 0.000 description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 8
- 241000002163 Mesapamea fractilinea Species 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 8
- 244000078703 ectoparasite Species 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 230000002265 prevention Effects 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 6
- 241000271566 Aves Species 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- 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 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 5
- ZMQMTKVVAMWKNY-YSXLEBCMSA-N emodepside Chemical compound C([C@@H]1C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C)C(=O)N(C)[C@H](C(O[C@H](CC=2C=CC(=CC=2)N2CCOCC2)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)C(C=C1)=CC=C1N1CCOCC1 ZMQMTKVVAMWKNY-YSXLEBCMSA-N 0.000 description 5
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- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 5
- 125000004001 thioalkyl group Chemical group 0.000 description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 108010034145 Helminth Proteins Proteins 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 238000009395 breeding Methods 0.000 description 4
- 230000001488 breeding effect Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 210000001147 pulmonary artery Anatomy 0.000 description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
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- 241000258242 Siphonaptera Species 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
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- 229940099245 milbemycin oxime Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 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
- 125000006107 n-hexyl sulfinyl 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
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 230000036281 parasite infection Effects 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000021317 phosphate Nutrition 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
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000006085 pyrrolopyridyl group Chemical group 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 125000001984 thiazolidinyl group Chemical group 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
- 239000000273 veterinary drug Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- 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
- 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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P17/00—Pest repellants
-
- 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
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
-
- 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
- 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
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562163997P | 2015-05-20 | 2015-05-20 | |
| US62/163,997 | 2015-05-20 | ||
| PCT/US2016/033522 WO2016187534A1 (en) | 2015-05-20 | 2016-05-20 | Anthelmintic depsipeptide compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2019137136A Division RU2019137136A (ru) | 2015-05-20 | 2016-05-20 | Противогельминтные депсипептидные соединения |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017144495A3 RU2017144495A3 (enExample) | 2019-06-20 |
| RU2017144495A RU2017144495A (ru) | 2019-06-20 |
| RU2707298C2 true RU2707298C2 (ru) | 2019-11-26 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017144495A RU2707298C2 (ru) | 2015-05-20 | 2016-05-20 | Противогельминтные депсипептидные соединения |
Country Status (32)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2747149C1 (ru) * | 2017-11-29 | 2021-04-28 | ЗОЕТИС СЕРВИСИЗ ЭлЭлСи | Анти-эндопаразитарные депсипептиды |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114891070A (zh) | 2015-05-20 | 2022-08-12 | 勃林格殷格翰动物保健美国公司 | 驱虫缩酚酸肽化合物 |
| KR20220003663A (ko) | 2015-12-28 | 2022-01-10 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 뎁시펩티드 화합물 |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| MX2019005628A (es) | 2016-11-16 | 2019-12-18 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos depsipeptidos antihelminticos. |
| AU2018219273B2 (en) | 2017-02-08 | 2023-08-17 | Boehringer lngelheim Vetmedica GMBH | In vivo model for parasitic worm infection and methods for evaluating antiparasitic compounds, including compounds active against canine heartworm |
| GB201713633D0 (en) * | 2017-08-24 | 2017-10-11 | Walshe Nigel | Methods for production of emodepside from pf 1022a derivatives |
| AU2018363696B2 (en) * | 2017-11-07 | 2023-09-14 | Elanco Animal Health Gmbh | Method for the synthesis of cyclic depsipeptides |
| EP3749096A1 (en) | 2018-02-08 | 2020-12-16 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof |
| CN112384511B (zh) * | 2018-05-10 | 2024-01-30 | 硕腾服务有限责任公司 | 内寄生虫缩肽 |
| EP3908330A1 (en) | 2019-01-10 | 2021-11-17 | Zoetis Services LLC | Anthelmintic laboratory animal model for heartworm |
| BR112021018631A2 (pt) | 2019-03-19 | 2021-11-23 | Boehringer Ingelheim Animal Health Usa Inc | Compostos anti-helmínticos de aza-benzotiofeno e aza-benzofurano |
| CN110343056B (zh) * | 2019-07-19 | 2022-01-07 | 爱斯特（成都）生物制药股份有限公司 | 一种n-叔丁氧羰基-n-甲基-2-氨基-4,4-二甲基戊酸的制备方法 |
| WO2021242581A1 (en) | 2020-05-29 | 2021-12-02 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic heterocyclic compounds |
| WO2022140728A1 (en) | 2020-12-21 | 2022-06-30 | Boehringer Ingelheim Animam Health Usa Inc. | Parasiticidal collar comprising isoxazoline compounds |
| 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 |
| CN114920669A (zh) * | 2022-06-28 | 2022-08-19 | 吉尔多肽生物制药(大连市)有限公司 | 一种n-甲基-n-苄氧羰基-l-天门冬氨酸（4-叔丁酯）二环己胺盐的合成方法 |
| CN116606237A (zh) * | 2023-05-23 | 2023-08-18 | 上海吉奉生物科技有限公司 | 一种色氨酸衍生物的合成方法 |
| CN116640091A (zh) * | 2023-05-25 | 2023-08-25 | 上海吉奉生物科技有限公司 | 一种Boc-3-（3-吡啶基）- L -丙氨酸的合成方法 |
| CN116655534A (zh) * | 2023-06-07 | 2023-08-29 | 上海吉奉生物科技有限公司 | 一种Boc-3-（3-吡唑）- L -丙氨酸的合成方法 |
| EP4538282A1 (en) * | 2023-10-13 | 2025-04-16 | Vetoquinol SA | Synthesis of emodepside |
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| EP0685469A1 (en) * | 1993-02-19 | 1995-12-06 | Meiji Seika Kaisha Ltd. | Pf1022 derivative, cyclic depsipeptide |
| EP0626375A1 (de) * | 1993-05-26 | 1994-11-30 | Bayer Ag | Octacylodepsideptide mit endoparasitizider Wirkung |
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| Krücken J et al "Anthelmintic cyclcooctadepsipeptides: complex in structure and mode of action.", Trends Parasitol. 2012 Sep; 28(9), 385-394. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2747149C1 (ru) * | 2017-11-29 | 2021-04-28 | ЗОЕТИС СЕРВИСИЗ ЭлЭлСи | Анти-эндопаразитарные депсипептиды |
| RU2747149C9 (ru) * | 2017-11-29 | 2021-06-29 | ЗОЕТИС СЕРВИСИЗ ЭлЭлСи | Анти-эндопаразитарные депсипептиды |
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