TWI693237B - 驅蟲酯肽化合物 - Google Patents

Info

Publication number

TWI693237B

TWI693237B TW105115872A TW105115872A TWI693237B TW I693237 B TWI693237 B TW I693237B TW 105115872 A TW105115872 A TW 105115872A TW 105115872 A TW105115872 A TW 105115872A TW I693237 B TWI693237 B TW I693237B

Authority

TW

Taiwan

Prior art keywords

alkyl

independently

group

halogen

substituted

Prior art date

2015-05-20

Links

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• 230000000507 anthelmentic effect Effects 0.000 title claims description 4
• 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 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 238
• 239000000203 mixture Substances 0.000 claims abstract description 114
• 241001465754 Metazoa Species 0.000 claims abstract description 61
• 244000045947 parasite Species 0.000 claims abstract description 56
• 206010061217 Infestation Diseases 0.000 claims abstract description 18
• -1 cyclic ester Chemical class 0.000 claims description 331
• 229910052736 halogen Inorganic materials 0.000 claims description 267
• 229910052739 hydrogen Inorganic materials 0.000 claims description 235
• 239000001257 hydrogen Substances 0.000 claims description 233
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 205
• 125000000217 alkyl group Chemical group 0.000 claims description 192
• 125000001424 substituent group Chemical group 0.000 claims description 184
• 150000002367 halogens Chemical class 0.000 claims description 179
• 125000001072 heteroaryl group Chemical group 0.000 claims description 172
• 125000000623 heterocyclic group Chemical group 0.000 claims description 146
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 131
• 150000001412 amines Chemical class 0.000 claims description 114
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 113
• 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 111
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 105
• 125000003118 aryl group Chemical group 0.000 claims description 95
• 125000004414 alkyl thio group Chemical group 0.000 claims description 94
• 125000003545 alkoxy group Chemical group 0.000 claims description 93
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 92
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 91
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 73
• 150000003839 salts Chemical class 0.000 claims description 65
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
• 125000003342 alkenyl group Chemical group 0.000 claims description 60
• 125000001188 haloalkyl group Chemical group 0.000 claims description 59
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 59
• 125000003282 alkyl amino group Chemical group 0.000 claims description 57
• 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 55
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
• 125000000304 alkynyl group Chemical group 0.000 claims description 51
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 47
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 46
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 42
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 32
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 229910052731 fluorine Inorganic materials 0.000 claims description 27
• 239000011737 fluorine Substances 0.000 claims description 25
• 239000013543 active substance Substances 0.000 claims description 21
• 239000003795 chemical substances by application Substances 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 15
• 208000030852 Parasitic disease Diseases 0.000 claims description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000004209 (C1-C8) alkyl group Chemical class 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000002837 carbocyclic group Chemical group 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• 239000000077 insect repellent Substances 0.000 claims description 6
• 125000004001 thioalkyl group Chemical group 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000002355 alkine group Chemical group 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 239000002917 insecticide Substances 0.000 claims description 2
• 230000000590 parasiticidal effect Effects 0.000 claims description 2
• RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims 2
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
• 150000002431 hydrogen Chemical class 0.000 claims 2
• 238000000034 method Methods 0.000 abstract description 24
• 241000124008 Mammalia Species 0.000 abstract description 19
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 128
• 125000005843 halogen group Chemical group 0.000 description 92
• 125000002757 morpholinyl group Chemical group 0.000 description 63
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 63
• 125000003373 pyrazinyl group Chemical group 0.000 description 62
• 125000004076 pyridyl group Chemical group 0.000 description 54
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 50
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 50
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 50
• 125000005265 dialkylamine group Chemical group 0.000 description 46
• 238000009472 formulation Methods 0.000 description 42
• 150000003973 alkyl amines Chemical class 0.000 description 41
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 39
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 37
• 125000000714 pyrimidinyl group Chemical group 0.000 description 36
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 35
• 125000002541 furyl group Chemical group 0.000 description 34
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• 125000002971 oxazolyl group Chemical group 0.000 description 33
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 32
• 125000000168 pyrrolyl group Chemical group 0.000 description 32
• 125000001544 thienyl group Chemical group 0.000 description 32
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 31
• 241000002163 Mesapamea fractilinea Species 0.000 description 31
• 229920000728 polyester Polymers 0.000 description 31
• 125000002883 imidazolyl group Chemical group 0.000 description 30
• 125000001786 isothiazolyl group Chemical group 0.000 description 30
• 125000003226 pyrazolyl group Chemical group 0.000 description 30
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 30
• 125000004306 triazinyl group Chemical group 0.000 description 29
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• 239000002904 solvent Substances 0.000 description 27
• 230000000694 effects Effects 0.000 description 25
• 229920001223 polyethylene glycol Polymers 0.000 description 25
• 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 24
• 239000002202 Polyethylene glycol Substances 0.000 description 24
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 22
• 239000004094 surface-active agent Substances 0.000 description 22
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 21
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 20
• 208000015181 infectious disease Diseases 0.000 description 20
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 19
• 241000282472 Canis lupus familiaris Species 0.000 description 18
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
• 125000005083 alkoxyalkoxy group Chemical group 0.000 description 18
• 238000002425 crystallisation Methods 0.000 description 18
• 230000008025 crystallization Effects 0.000 description 18
• 239000003112 inhibitor Substances 0.000 description 18
• 238000006467 substitution reaction Methods 0.000 description 18
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 description 17
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 14
• 239000012071 phase Substances 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 13
• 239000000796 flavoring agent Substances 0.000 description 13
• 235000014113 dietary fatty acids Nutrition 0.000 description 12
• 239000000194 fatty acid Substances 0.000 description 12
• 229930195729 fatty acid Natural products 0.000 description 12
• 125000001153 fluoro group Chemical group F* 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
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• 239000000243 solution Substances 0.000 description 12
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• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 11
• 102000004196 processed proteins & peptides Human genes 0.000 description 11
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• 241000244206 Nematoda Species 0.000 description 10
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• 230000015572 biosynthetic process Effects 0.000 description 10
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 239000003085 diluting agent Substances 0.000 description 10
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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• 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 9
• 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
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• 125000005842 heteroatom Chemical group 0.000 description 9
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• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
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