JP2017530093A - 駆虫薬としての新規スルホニルアミノベンズアミド化合物 - Google Patents
駆虫薬としての新規スルホニルアミノベンズアミド化合物 Download PDFInfo
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- JP2017530093A JP2017530093A JP2017506992A JP2017506992A JP2017530093A JP 2017530093 A JP2017530093 A JP 2017530093A JP 2017506992 A JP2017506992 A JP 2017506992A JP 2017506992 A JP2017506992 A JP 2017506992A JP 2017530093 A JP2017530093 A JP 2017530093A
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- Prior art keywords
- substituted
- alkyl
- halogen
- haloalkyl
- alkoxy
- Prior art date
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- CAWFFBLMSQUZPF-UHFFFAOYSA-N 2-(sulfonylamino)benzamide Chemical class NC(=O)C1=CC=CC=C1N=S(=O)=O CAWFFBLMSQUZPF-UHFFFAOYSA-N 0.000 title description 3
- 239000003096 antiparasitic agent Substances 0.000 title 1
- 229940125687 antiparasitic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 244000045947 parasite Species 0.000 claims abstract description 13
- 244000079386 endoparasite Species 0.000 claims abstract description 9
- -1 SF 5 Chemical group 0.000 claims description 160
- 150000002367 halogens Chemical class 0.000 claims description 133
- 229910052736 halogen Inorganic materials 0.000 claims description 132
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 35
- 241001465754 Metazoa Species 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 14
- 229910052796 boron Inorganic materials 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000003386 piperidinyl group Chemical group 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 11
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 7
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 7
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 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 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004522 1,3,4-thiadiazol-5-yl group Chemical group S1C=NN=C1* 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 241000723346 Cinnamomum camphora Species 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 229930008380 camphor Natural products 0.000 claims description 2
- 229960000846 camphor Drugs 0.000 claims description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 4
- 241000251539 Vertebrata <Metazoa> Species 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 0 **C(c1cc(*)ccc1[N+]([O-])=O)=O Chemical compound **C(c1cc(*)ccc1[N+]([O-])=O)=O 0.000 description 5
- 241000243988 Dirofilaria immitis Species 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 229940099686 dirofilaria immitis Drugs 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- DSSYKIVIOFKYAU-OIBJUYFYSA-N (S)-camphor Chemical compound C1C[C@]2(C)C(=O)C[C@H]1C2(C)C DSSYKIVIOFKYAU-OIBJUYFYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003071 parasitic effect Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 229930007886 (R)-camphor Natural products 0.000 description 3
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 125000004995 haloalkylthio group Chemical group 0.000 description 3
- 244000000013 helminth Species 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 230000033001 locomotion Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 229940075963 (-)- camphor Drugs 0.000 description 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
- XCVCVXQXUHWWMN-UHFFFAOYSA-N 5-chloro-2-nitro-N-(3,4,5-trichlorophenyl)benzamide Chemical compound [O-][N+](=O)C1=C(C=C(Cl)C=C1)C(=O)NC1=CC(Cl)=C(Cl)C(Cl)=C1 XCVCVXQXUHWWMN-UHFFFAOYSA-N 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 2
- 241000244186 Ascaris Species 0.000 description 2
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- 241001126268 Cooperia Species 0.000 description 2
- 241001147667 Dictyocaulus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000242711 Fasciola hepatica Species 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 241000243976 Haemonchus Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 206010062717 Increased upper airway secretion Diseases 0.000 description 2
- 241001626440 Joyeuxiella Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UMAMCCVQWMKGLF-UHFFFAOYSA-N N-[3,5-bis(trifluoromethyl)phenyl]-5-bromo-2-(methanesulfonamido)benzamide Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)NC(C1=C(C=CC(=C1)Br)NS(=O)(=O)C)=O)(F)F UMAMCCVQWMKGLF-UHFFFAOYSA-N 0.000 description 2
- 241001137882 Nematodirus Species 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000244174 Strongyloides Species 0.000 description 2
- 241000244154 Taenia ovis Species 0.000 description 2
- 241000243774 Trichinella Species 0.000 description 2
- 241001489151 Trichuris Species 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 230000002141 anti-parasite Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 210000002216 heart Anatomy 0.000 description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 2
- 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 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
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- 210000004185 liver Anatomy 0.000 description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/56—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
Description
発明の概要
nは0または1であって、
AはC1〜C6−アルキルであり、C1〜C6−ハロアルキルであり、C3〜C6−シクロアルキルであり、C3〜C6−ハロシクロアルキルであり、B、N、OおよびSから成る群から選択される1〜3個の同じまたは異なるヘテロ原子を有する5または6員のヘテロシクロアルキルであり、ハロゲン、C1〜C4−アルキルまたはC1〜C4−アルコキシによってさらに置換されないまたは置換され、またはハロゲン、C1〜C6−アルキル、C1〜C6−ハロアルキル、C3〜C6−シクロアルキル、C3〜C6−ハロシクロアルキル、C1〜C6−アルコキシ、C1〜C6−ハロアルコキシ、C1〜C6−アルキルチオ、C1〜C6−ハロアルキルチオ、C1〜C6−アルキル−スルフィニル、C1〜C6−ハロアルキルスルフィニル、C1〜C6−アルキルスルホニル、C1〜C6−ハロアルキルアルキルスルホニル、SF5によって置換されないまたは置換されるフェニルであり、アミノ、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノ、トリ−C1〜C4−アルキルシリル、C1〜C6−アルコキシカルボニル、アミノカルボニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノカルボニル、アミノスルホニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノスルホニル、C1〜C6−アルコキシカルボニルアミノ、N−C1〜C4−アルキル−N−C1〜C6−アルコキシカルボニルアミノ、シアノ、ニトロ、または非置換もしくはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、C1〜C4−アルコキシ−、C1〜C4−ハロアルコキシ−、アミノ−、シアノ−もしくはニトロ置換C3〜C6−ヘテロシクリルであり、またはシンナミルであり、ハロゲン、C1〜C4−アルキルもしくはC1〜C4−アルコキシによってフェニル部分で置換されないまたは置換され、またはヘテロ芳香族基であり、ハロゲン、シアノ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−ハロアルコキシ、C2〜C4−アルカノイル、5または6員のヘテロシクロアルキル−C1〜C2−アルキルまたは非置換もしくはハロゲン−、C1〜C4−アルキル−またはC1〜C4−アルコキシ置換フェニルによってさらに置換されないまたは置換され、または合計8〜10個の環員を含むヘテロ二環式環であり、1〜5個、好ましくは1または2個の員はB、N、OおよびSから成る群から選択される同じまたは異なるヘテロ原子であり、0〜2個の員は-C(O)−基であり、二環式環基はハロゲン、シアノ、ヒドロキシル、C1〜C4−アルキルまたはC1〜C4−ハロアルキルによって置換されないまたは置換され、
R2はHまたは-S(O2)−Tであり、
TはC1〜C6−アルキルであり、ハロゲン、トリメチルシリル、C3〜C6−シクロアルキル、カルボキシルまたはC1〜C4−アルコキシカルボニルによって置換されないまたは置換され、C3〜C6−シクロアルキルであり、C6〜C12−ビカルボシクリルであり、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキルまたはC1〜C4−アルコキシによって置換されないまたは置換されるフェニルであり、5または6員のヘテロ芳香族基であり、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシによってさらに置換されないまたは置換され、N、O、SおよびS(O2)から成る群から選択される1〜3個の同じまたは異なるヘテロ原子を有する5または6員のヘテロシクロアルキルであり、C1〜C4−アルキル、C1〜C2−アルコキシカルボニルまたは
ベンジルオキシカルボニルによってさらに置換されないまたは置換され、基
R3はC1〜C4−アルキル、非置換またはハロゲン−、C1〜C4−アルキル−もしくはC1〜C4−ハロアルキル置換フェニル、非置換またはハロゲン−、C1〜C4−アルキル−またはC1〜C4−ハロアルキル置換ピリジル、C1〜C4−アルコキシカルボニルメチルまたはモルホリン−4−イル−カルボニルメチルであり、
R0はHまたはヒドロキシであり、
Yは
(i)フェニルまたはフェニルアミノであり、ハロゲン、C1〜C6−アルキル、C1〜C6−ハロアルキル、C3〜C6−シクロアルキル、C3〜C6−ハロシクロアルキル、ヒドロキシル、C1〜C6−アルコキシ、C1〜C6−ハロアルコキシ、C1〜C6−アルキルチオ、C1〜C6−ハロ−アルキルチオ、C1〜C6−アルキル−スルフィニル、C1〜C6−ハロアルキルスルフィニル、C1〜C6−アルキルスルホニル、C1〜C6−ハロアルキル−スルホニル、SF5、アミノ:N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノ、トリ−C1〜C4−アルキルシリル、C1〜C6−アルコキシカルボニル、アミノカルボニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノカルボニル、アミノスルホニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノスルホニル、N−C1〜C6−アルキルスルホニルアミノ、C1〜C6−アルコキシ−カルボニル−アミノ、N−C1〜C4−アルキル−N−C1〜C6−アルコキシカルボニルアミノ、シアノ、ニトロ、および非置換もしくはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、C1〜C4−アルコキシ−、C1〜C4−ハロアルコキシ−、アミノ−、シアノ−もしくはニトロ−置換C3〜C6−ヘテロシクリルから成る群から選択される1つまたは複数の同じまたは異なる基によって置換され、または
(ii)5または6員のヘテロアリールまたはヘテロアリールアミノであり、それぞれ、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−アルコキシカルボニル、C2〜C4−アルカノイル、またはハロゲン、シアノ、ニトロ、メチルもしくはメトキシによってそれぞれ置換されないまたは置換されるフェニルまたはフェニルスルホニルによってさらに置換されないまたは置換され、または
(iii)ベンゾイルまたは5または6員のヘテロアリールカルボニルであり、それぞれ、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−アルコキシカルボニル、C2〜C4−アルカノイルまたはフェニルによってさらに置換されないまたは置換され、または
(iv)C6〜C12−二炭素環式基であり、または
(v)合計8〜10個の環員を含むヘテロ−二環式環基であり、1〜5個の員、好ましくは1または2個の員は、B、N、OおよびSから成る群から選択される同じまたは異なるヘテロ原子であり、0〜2個の員は-C(O)−基であり、二環式環基はハロゲン、シアノ、ヒドロキシル、C1〜C4−アルコキシ、C1〜C4−アルキルまたはC1〜C4−ハロアルキルによってさらに置換されないまたは置換され、または
(vi)-H2C−C(O)−NH−R4基であり、ここでR4はC1〜C4−ハロアルキル、C2〜C3−アルキニルまたはシアノ−C1〜C4−アルキルであり、または
R0およびYはそれらが結合されるN原子と一緒になって、C1〜C4−アルキル、C1〜C4−アルコキシ、非置換またはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、アミノ−および/またはC1〜C4−アルコキシ置換フェニルもしくはベンゾイルアミノまたは非置換もしくはC1〜C4−アルキル−、C1〜C4−ハロアルキル−、C3〜C6−シクロアルキル−またはハロゲン−置換ピリジルもしくはピリミジニルによって置換されるピペリジニルまたはピペラジニル基を形成し、
ただし、
(i)TがCH3である場合、AおよびYの少なくとも一つはフェニル基であってはならず、
(ii)AがC1〜C6−アルキルまたはC1〜C6−ハロアルキルである場合、Tは上述のように置換されないまたは置換されるC1〜C6−アルキルである。
上述の「アルキル」という用語は、単独または「アルキルチオ」、「ハロアルキルチオ」、「ハロアルキル」、「N−アルキルアミノ」、「N,N−ジ−アルキルアミノ」等の化合物の用語のいずれかで使用され、メチル、エチル、n−プロピル、i−プロピル、n−、イソ−、sec.−またはtert.−ブチルまたは異なるペンチルもしくはヘキシル等の直鎖または分岐鎖アルキルを含む。
(i)5または6員のヘテロアリールまたはヘテロアリールアミノであり、それぞれ、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−アルコキシカルボニル、C1〜C4−アルカノイルまたはそれぞれハロゲン、シアノ、ニトロ、メチルもしくはメトキシによって置換されないまたは置換されるフェニルもしくはフェニルスルホニルによってさらに置換されないまたは置換され、
(ii)ベンゾイルまたは5または6員のヘテロアリールカルボニルであり、それぞれ、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−アルコキシカルボニル、C1〜C4−アルカノイルまたはフェニルによってさらに置換されないまたは置換され、
(iii)C6〜C12−二炭素環式基であり、または
(iv)合計8〜10個の環員を含むヘテロ二環式環基であり、1〜5個、好ましくは1または2個の員はB、N、OおよびSから成る群から選択される同じまたは異なるヘテロ原子であり、0〜2個の員は-C(O)−基であり、二環式環基はハロゲン、シアノ、ヒドロキシル、C1〜C4−アルコキシ、C1〜C4−アルキルまたはC1〜C4−ハロアルキルによってさらに置換されないまたは置換され、または
(v)-H2C−C(O)−NH−R4基であって、R4はC1〜C4−ハロアルキル、C2〜C3−アルキニルまたはシアノ−C1〜C4−アルキルであり、またはR0およびYはそれらが結合されるN原子と一緒になって、C1〜C4−アルキル、C1〜C4−アルコキシ非置換またはハロゲン−、C1〜C4−アルキル−、ハロ−C1〜C4−アルキル−、アミノ−および/またはC1〜C4−アルコキシ置換フェニルもしくはベンゾイルアミノまたは非置換もしくはC1〜C4−アルキル−、C1〜C4−ハロアルキル−、C3〜C6−シクロアルキル−またはハロゲン−置換ピリジルもしくはピリミジニルによって置換されるピペリジニルまたはピペラジニル基を形成する。
(i)ハロゲン、C1〜C4−アルキルまたはC1〜C2−アルコキシによって置換されないまたは置換される2−、3−または4−ピリジルであり、C1〜C2−アルキル、C1〜C2−アルコキシカルボニルによって置換されないまたは置換される2−チエニルであり、ハロゲン、シアノ、ニトロ、C1〜C2−アルキル、C1〜C2−ハロアルキル、C1〜C2−アルコキシカルボニル、またはそれぞれ順番にハロゲン、シアノ、ニトロもしくはメチルによって置換されないまたは置換されるフェニルもしくはフェニルスルホニルによって置換されないまたは置換される2−チアゾリルであり、ハロゲンまたはメチルによって置換されないまたは置換される5−イソチアゾイルであり、2−オキサゾリルであり、C1〜C2−アルキルまたはC1〜C2−ハロアルキルによって置換されないまたは置換され、またはC1〜C2−アルキルまたはC1〜C2−ハロアルキルよって置換されないまたは置換される1,3,4−チアジアゾール−5−イルであり、ハロゲン、C1〜C4−アルキルまたはC1〜C2−アルコキシによって置換されないまたは置換される2−、3−または4−ピリジルアミノであり、または
(ii)ハロゲンまたはC1〜C4−アルキルによって置換されないまたは置換される2−、3−もしくは4−ピリジルカルボニルによって置換されないまたは置換されるベンゾイルであって、または
(iii)基
基
(iv)ベンゾチアゾリル、インドリル、キノリニル、メチレンジオキソ−フェニル、ベンゾオキサボロニル、トリアゾロピリミジノニルまたはフタルヒドラジジルであり、それぞれハロゲン、C1〜C4−アルキル、C1〜C2−ハロアルキルまたはヒドロキシによって置換されないまたは置換され、または
(v)-H2C−C(O)−NH−CH2−C≡CH基、-H2C−C(O)−NH−CH2−CN基または-H2C−C(O)−NH−CH2−CF3であって、またはR0およびYはそれらが結合されるN原子と一緒になって、ピペリジニルもしくはピペラジニル基を形成し、メチル、メトキシ、ハロゲン−、アミノ−、メトキシ−もしくはトリフルオロメチル置換フェニルまたはベンゾイルアミノ、またはハロゲン−、トリフルオロメチル−および/もしくはシクロプロピル置換ピリジルまたはピリミジニルによって置換される。
式
式
ここで変数は上述の通りであり、ニトロ基の還元後、得られたアミンをメタンスルホニルクロリドとさらに反応させる。これらの反応の詳細は有機化学のテキストで既知である。式(VI)の化合物は、式(II)の式の化合物と類似して調製することができる。式(VII)の化合物はそれ自体既知であり、市販されている。
式
2−(メチルスルホンアミド)−5−モルホリノ−N−(3,4,5−トリクロロフェニル)ベンズアミドの合成(表1の例1.2)
5−クロロ−2−ニトロ安息香酸(10g)を還流で4時間、塩化チオニル(7.2mL)で処理した。過剰なSOCl2を真空下で取り除いた。CH2Cl2(100mL)を塩化アシルに添加した。0℃で、100mLのCH2Cl2中の3,4,5−トリクロロアニリン(9.7g)およびNEt3(13.8mL)をゆっくりと添加した。反応混合物を温め、室温で一晩攪拌した。反応混合物を200mLのジエチルエーテルで希釈した。10mLのHCl 2 Nおよび200mLのH2Oを添加し、混合物を黄色の沈殿物が形成されるまで攪拌した。沈殿物を濾去し、分析前に高真空下で乾燥させた(収率66%)。LCMS(方法B):1.97分で380.59(M+H)+。
1.5mLのDMF中の300mgの5−クロロ−2−ニトロ−N−(3,4,5−トリクロロフェニル)ベンズアミドの溶液にモルホリン(206μL)を添加した。反応混合物を110℃で1.5時間加熱した。AcOEtでワークアップおよび抽出を行った後、混合物を蒸発乾固した。表題化合物はステップBに進むのに十分に純粋であった(収率71%)。LCMS(方法B):1.81分で427.7(M−H)−。
N2下で、4mLのEtOH/H2O(3/1)中の5−モルホリノ−2−ニトロ−N−(3,4,5−トリクロロフェニル)ベンズアミド(230mg)を、Fe(208mg)および25%のHCl(4μL)で処理し、反応混合物を室温で4時間攪拌した。還元か完了した後、反応混合物をセライトのプラグで濾過し、酢酸エチルで洗浄した。濾液を真空下で蒸発させた。酢酸エチルを添加し、有機層をブラインで洗浄し、MgSO4で乾燥させ、蒸発乾固した(収率95%)。LCMS(方法B):1.61分で399.68(M+H)+。
3mLのCH2Cl2中の2−アミノ−5−モルホリノ−N−(3,4,5−トリクロロフェニル)ベンズアミド(193mg)のN2脱ガス溶液に、ピリジン(0.194mL)を添加した。混合物を0℃で冷却し、メタンスルホニルクロリド(0.037mL)を滴下した。反応混合物を室温で一晩攪拌し、50mLの酢酸エチルで希釈した。有機層をNa2CO3の飽和溶液とブラインで洗浄し、MgSO4で乾燥させ、蒸発乾固した(収率43%。LCMS(方法B):1.78分で477.7(M+H)+。
N−(3,5−ビス(トリフルオロメチル)フェニル)−5−(2−フルオロピリジン−3−イル)−2−(メチルスルホンアミド)ベンズアミド(表1の例1.14)
10mLの1ピリジン中の2−アミノ−5−ブロモ安息香酸メチル(2.8g)のN2脱ガス溶液を0℃で冷却し、メタンスルホニルクロリド(0.9mL)を滴下した。反応混合物を室温で一晩攪拌し、50mLの酢酸エチルで希釈した。有機層をNa2CO3の飽和溶液とブラインとで洗浄し、MgSO4で乾燥させ、蒸発乾固した(収率82%)。LCMS(方法B):1.55分で305.6(M−H)−。
メチル5−ブロモ−2−(メチルスルホンアミド)ベンゾアート(3.15g)をTHF(20mL、1/1)に懸濁した。NaOH 4N(6.9mL)を添加し、反応混合物を還流で4時間攪拌した。完了した後、反応混合物を2N HCl(1mL)で処理し、酢酸エチルで2回抽出した。一つに合わせた有機層をH2O、ブラインで洗浄し、Na2SO4で乾燥させ、濾過し、蒸発乾固した。表題の生成物は、LCMSによって、さらに精製することなく次のステップに進むのに純粋であった(収率:66%)。LCMS(方法B):1.2分で291.64(M−H)−。
5−ブロモ−2−(メチルスルホンアミド)安息香酸(2.4g)を還流で4時間、塩化チオニル(23mL)で処理した。過剰なSOCl2を真空下で取り除いた。CH2Cl2(20mL)を塩化アシルに添加した。0℃で、10mLのCH2Cl2中の3,5−ビス(トリフルオロメチル)アニリン(1.4mL)およびNEt3(5.68mL)をゆっくりと添加した。反応混合物を温め、室温で一晩攪拌した。
LCMS(方法B):1.99分で502.93(M−H)−。
N2下で、ジオキサン/H2O(6mL、1/1)中のN−(3,5−ビス(トリフルオロメチル)フェニル)−5−ブロモ−2−(メチルスルホンアミド)ベンズアミド(0.2g)および2−フルオロ−3−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)ピリジン(133mg)の溶液に、Na2CO3(252mg)、Pd(dppf)Cl2.CH2Cl2(355mg)を添加した。反応混合物を80℃で3時間攪拌した。酢酸エチルで希釈し、セライトによって濾過した。濾液をH2O、ブラインで洗浄し、Na2SO4で乾燥させ、濾過し、蒸発乾固した。
LCMS(方法C):1.90分で521.8(M+H)+。
5−フェノキシ−2−(フェニルスルホンアミド)−N−(3,4,5−トリクロロフェニル)ベンズアミド(表2の例2.2)
DMA中の5−クロロ−2−ニトロ−N−(3,4,5−トリクロロフェニル)ベンズアミド(29.1g)、K2CO3(21.3g)およびフェノール(8g)を140℃で14時間加熱した。反応混合物をH2O(100mL)に注ぎ、沈殿物を濾去し、高真空下で乾燥させ、茶色の固体を得た(収率80%)。LCMS(方法B):2.14分で436.6(M−H)−。
2−ニトロ−5−フェノキシ−N−(3,4,5−トリクロロフェニル)ベンズアミドを、ステップC実施例1に記載の方法と同様の方法で鉄で処理した(収率27%)。LCMS(方法B):2.28分で406.7(M+H)+。
2mLのCH2Cl2中の2−アミノ−5−フェノキシ−N−(3,4,5−トリクロロフェニル)ベンズアミド(0.26mg)のN2脱ガス溶液に、ピリジン(0.25mL)を添加した。混合物を0℃で冷却し、ベンゼンスルホニルクロリド(0.124mg)を滴下した。反応混合物を室温で一晩攪拌し、追加の5mLのCH2Cl2で希釈した。有機層をNa2CO3の飽和溶液とブラインとで洗浄し、MgSO4で乾燥させ、蒸発乾固した(収率81%)。LCMS(方法B):2.39分で546.7(M+H)+。
2−(メチルスルホンアミド)−N−(3,4,5−トリクロロフェニル)−5−((2−(トリフルオロメチル)ピリジン−3−イル)オキシ)ベンズアミド(表3の例3.2)
5−クロロ−2−ニトロ安息香酸メチルを実施例3の合成のステップAと同様の方法で処理した(収率28%)。LCMS(方法B):1.63分で342.86(M+H)+。
2−ニトロ−5−((2−(トリフルオロメチル)ピリジン−3−イル)オキシ)安息香酸メチル(277mg)を、THF/MeOH(8mL、2/1)中、NaOH 1N(4.13mL)で室温で一晩処理した(収率98%)。LCMS(方法B):1.33分で328.84(M+H)+。
2−ニトロ−5−((2−(トリフルオロメチル)ピリジン−3−イル)オキシ)安息香酸を実施例1の合成のステップAと同様の方法で処理した(収率45%)。LCMS(方法B):2.05分で505.7(M+H)+。
5−(4−クロロフェノキシ)−2−(メチルスルホンアミド)−N−(4−(トリフルオロメチル)オキサゾール−2−イル)ベンズアミド(表4の例4.16)
5−クロロ−2−ニトロ安息香酸メチルを実施例3の合成のステップAと同様の方法で処理した(収率90%)。LCMS(方法B):1.67分で305.0(M+H)+。
5−(4−クロロフェノキシ)−2−ニトロ安息香酸メチルを実施例1の合成のステップCと同様の方法で処理した(収率100%)。LCMS(方法B):1.88分で277.82(M+H)+。
2−アミノ−5−(4−クロロフェノキシ)安息香酸メチルを実施例1の合成のステップDと同様の方法で処理した(収率95%)。LCMS(方法B):1.84分で353.78(M−H)−。
5−(4−クロロフェノキシ)−2−(メチルスルホンアミド)安息香酸メチルを実施例4の合成のステップBと同様の方法で処理した(収率96%)。LCMS(方法B):1.61分で339.62(M−H)−。
5−(4−クロロフェノキシ)−2−(メチルスルホンアミド)安息香酸を実施例1の合成のステップAと同様の方法で処理した(収率3%)。LCMS(方法B):1.70分で475.64(M+H)+。
胃腸における幼虫の発生アッセイ
新しく回収し清潔な線虫の卵を使用して、試験物質を含む適切にフォーマットしたプレートに播種し、抗寄生虫的活動および卵を3令幼虫を通じて完全に発育させることができる培地を評価する。プレートを25℃、60%の相対湿度で6日間インキュベートする。卵孵および結果として生じる幼虫の発生を記録し、可能性としてある殺線虫の活動を識別する。有効性は、卵孵が減少した割合、L3の発生の減少または任意のステージでの運動麻痺および死亡で表す。化合物No.1.4、1.10−1.12、1.14、1.16−1.21、1.23、1.25−1.26、1.29−1.33、2.1、2.22、2.28、2.42−2.43、3.1−3.2、4.1、4.3−4.8、4.19−4.24、4.28、4.32、4.34、4.36−4.37、4.39、4.42−4.43および4.51は、10ppmで60%以上の有効性を達成し、したがって活性であると考えられる。
新しく回収し清潔なDirofilaria immitisミクロフィラリアをドナー動物のイヌの血液から調製する。ミクロフィラリアを試験物質を含むフォーマットしたマクロプレートに分配し、抗寄生虫的活動を評価する。プレートを25℃、60%の相対湿度(RH)で48時間インキュベートする。ミクロフィラリアの運動性を記録し、有効性を決定した。有効性は、対照および標準と比較した運動性の減少の割合で表す。化合物No.1.2−1.4および1.6〜1.33、2.1−2.20、2.22−2.44、2.46、3.1−3.4、4.1−4.10、4.12−4.16、4.17−4.18、4.21−4.29、4.31−4.39、4.42および4.46−4.52は、10ppmで50%以上の有効性を達成し、したがって活性であると考えられる。
スナネズミを皮下注射によって人工的にA.viteaeの80 L3幼虫に感染させる。処方した試験化合物で経管栄養する処理を、感染後、5日目から9日目まで連続して行う。感染後84日目に、Fuchs-Rosenthal血算盤および顕微鏡を使用して、循環しているミクロフィラリアの数を数えるために出血させる。循環しているミクロフィラリアの数の平均がプラセボ処理群より少なくとも50%低い試験群のみを、成虫を回収するために完全に解剖する。有効性は、Abbot公式を使用して、プラセボ処理群と比較した寄生虫の数の減少の割合として表す。化合物No.1.6−1.8、1.17、1.25、1.30、1.32、2.24、4.13、4.24は、10mg/kgで80%以上の有効性を示した。
ウシまたはヒツジの肝臓から新しく回収した成虫のFasciola hepaticaを、4mLのRPMI完全培地で、12ウェルのプレート(ウェルあたり1隻の吸虫)に分配し、37℃で約12時間孵卵器に保持した。培地を新しくした後、肝蛭の生存率は個々の肝蛭の動きをビデオ登録することによって決定する(前値)。試験化合物を100μg/mLの濃度で添加し、肝蛭の動きを6時間後および24時間後に測定する。有効性は、前値と未処理群に基づいて、動きの減少率として表す。この試験では、実施例2.2、4.13で6時間後に90%超の有効性、24時間後に95%超の有効性を示し、ポジティブであると考えられる。
Claims (11)
- 式
nは0または1であり、
AはC1〜C6−アルキルであり、C1〜C6−ハロアルキルであり、C3〜C6−シクロアルキルであり、C3−C6−ハロシクロアルキルであり、B、N、OおよびSから成る群から選択される1〜3個の同じまたは異なるヘテロ原子を有する5または6員のヘテロシクロアルキルであり、ハロゲン、C1〜C4−アルキルまたはC1〜C4−アルコキシによってさらに置換されないまたは置換され、またはハロゲン、C1〜C6−アルキル、C1〜C6−ハロアルキル、C3〜C6−シクロアルキル、C3〜C6−ハロシクロアルキル、C1〜C6−アルコキシ、C1〜C6−ハロアルコキシ、C1〜C6−アルキルチオ、C1〜C6−ハロアルキルチオ、C1〜C6−アルキル−スルフィニル、C1〜C6−ハロアルキルスルフィニル、C1〜C6−アルキルスルホニル、C1〜C6−ハロアルキルスルホニル、SF5、アミノ、N−モノ−もしくはN,N−ジ−C1−C6−アルキルアミノ、トリ−C1〜C4−アルキルシリル、C1〜C6−アルコキシカルボニル、アミノカルボニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノカルボニル、アミノスルホニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノスルホニル、C1〜C6−アルコキシカルボニルアミノ、N−C1〜C4−アルキル−N−C1〜C6−アルコキシカルボニルアミノ、シアノ、ニトロ、または非置換もしくはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、C1〜C4−アルコキシ−、C1〜C4−ハロアルコキシ−、アミノ−、シアノ−もしくはニトロ−置換C3〜C6−ヘテロシクリルによって置換されないまたは置換されるフェニル基であり、またはハロゲン、C1〜C4−アルキルもしくはC1〜C4−アルコキシによってフェニル部分で置換されないまたは置換されるシンナミルであり、またはハロゲン、シアノ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−ハロアルコキシ、C2〜C4−アルカノイル、5または6員のヘテロシクロアルキル−C1〜C2−アルキルまたは非置換もしくはハロゲン−、C1〜C4−アルキル−またはC1〜C4−アルコキシ−置換フェニルによってさらに置換されないまたは置換されるヘテロ芳香族基であり、または合計8〜10個の環員を含むヘテロ−二環式環であり、1〜5個の員は、B、N、OおよびSから成る群から選択される同じもしくは異なるヘテロ原子であり、0〜2個の員は-C(O)−基であり、二環式環はハロゲン、シアノ、ヒドロキシル、C1〜C4−アルキルまたはC1〜C4−ハロアルキルによってさらに置換されないまたは置換され、
R2はHまたは-S(O2)−Tであり、
Tはハロゲン、トリメチルシリル、C3−C6−シクロアルキル、カルボキシルまたはC1〜C4−アルコキシカルボニルによって置換されないまたは置換されるC1〜C6−アルキルであり、C3−C6−シクロアルキルであり、C6−C12−ビカルボシクリルであり、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキルまたはC1〜C4−アルコキシによって置換されないまたは置換されるフェニルであり、ハロゲン、シアノ、ニトロ、C1−C4−アルキル、C1−C4−ハロアルキルまたはC1−C4−アルコキシによってさらに置換されないまたは置換される5または6員のヘテロ芳香族基であり、N、O、SおよびS(O2)から成る群から選択される1〜3個の同じまたは異なるヘテロ原子を有する5または6員のヘテロシクロアルキルであり、C1−C4−アルキル、C1−C2−アルコキシカルボニルまたはベンジルオキシカルボニルによってさらに置換されないまたは置換され、基
R3はC1〜C4−アルキル、非置換またはハロゲン、C1〜C4−アルキル−またはC1〜C4−ハロアルキル−置換フェニル、非置換またはハロゲン−、C1〜C4−アルキル−またはC1〜C4−ハロアルキル−置換ピリジル、C1〜C4−アルコキシ−カルボニル−メチルまたはモルホリン−4−イル−カルボニルメチルであり、
R0はHまたはヒドロキシであり、
Yは
(i)フェニルまたはフェニルアミノであり、ハロゲン、C1〜C6−アルキル、C1〜C6−ハロアルキル、C3〜C6−シクロアルキル、C3〜C6−ハロシクロアルキル、ヒドロキシル、C1〜C6−アルコキシ、C1〜C6−ハロアルコキシ、C1〜C6−アルキルチオ、C1〜C6−ハロアルキルチオ、C1〜C6−アルキル−スルフィニル、C1〜C6−ハロアルキルスルフィニル、C1〜C6−アルキルスルホニル、C1〜C6−ハロアルキルスルホニル、SF5、アミノ、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノ、トリ−C1〜C4−アルキルシリル、C1〜C6−アルコキシカルボニル、アミノ−カルボニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノカルボニル、アミノスルホニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノスルホニル、N−C1〜C6−アルキルスルホニルアミノ、C1〜C6−アルコキシカルボニルアミノ、N−C1〜C4−アルキル−N−C1〜C6−アルコキシカルボニルアミノ、シアノ、ニトロ、および非置換もしくはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、C1〜C4−アルコキシ−、C1〜C4−ハロアルコキシ−、アミノ−、シアノ−もしくはニトロ−置換C3〜C6−ヘテロシクリルから成る群から選択される1つまたは複数の同じまたは異なる基によって置換され、または
(ii)5または6員のヘテロアリールまたはヘテロアリールアミノであり、それぞれ、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−アルコキシカルボニル、C2〜C4−アルカノイル、またはハロゲン、シアノ、ニトロ、またはメチルもしくはメトキシによって置換されないまたは置換されるフェニルもしくはフェニルスルホニルによってさらに置換されないまたは置換され、または
(iii)ベンゾイルまたは5もしくは6員のヘテロアリールカルボニルであり、それぞれ、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−アルコキシカルボニル、C2〜C4−アルカノイルまたはフェニルによってさらに置換されないまたは置換され、または
(iv)C6〜C12−二炭素環式基であり、または
(v)合計8〜10個の環員を含むヘテロ−二環式環基であり、1〜5個の員、好ましくは1または2個の員はB、N、OおよびSから成る群から選択される同じまたは異なるヘテロ原子であり、0〜2個の員は-C(O)−基であり、二環式環基はハロゲン、シアノ、ヒドロキシル、C1〜C4−アルコキシ、C1〜C4−アルキルまたはC1〜C4−ハロアルキルによってさらに置換されないまたは置換され、または
(vi)-H2C−C(O)−NH−R4基であり、ここでR4はC1〜C4−ハロアルキル、C2〜C3−アルキニルまたはシアノ−C1〜C4−アルキルであり、または
R0およびYは、それらが結合されるN原子と一緒になってC1〜C4−アルキル、C1〜C4−アルコキシ、非置換またはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、アミノ−および/またはC1〜C4−アルコキシ−置換フェニルまたはベンゾイルアミノ、または非置換もしくはC1〜C4−アルキル−、C1〜C4−ハロアルキル−、C3〜C6−シクロアルキル−またはハロゲン−置換ピリジルもしくはピリミジニルによって置換されるピペリジニルまたはピペラジニル基を形成し、ただし、
(i)TがCH3である場合、AおよびYの少なくとも1つはフェニル基であってはならず、
(ii)AがC1〜C6−アルキルまたはC1〜C6−ハロアルキルである場合、Tは上述のように置換されないまたは置換されるC1〜C6−アルキルである、前記化合物。 - 式
Y’はハロゲン、C1〜C6−アルキル、C1〜C6−ハロアルキル、C3〜C6−シクロアルキル、C3〜C6−ハロシクロ−アルキル、ヒドロキシル、C1〜C6−アルコキシ、C1〜C6−ハロアルコキシ、C1〜C6−アルキルチオ、C1〜C6−ハロアルキルチオ、C1〜C6−アルキル−スルフィニル、C1〜C6−ハロアルキルスルフィニル、C1〜C6−アルキルスルホニル、C1〜C6−ハロアルキルスルホニル、SF5、アミノ、N−モノ−もしくはN,N−ジ−C1−C6−アルキルアミノ、トリ−C1−C4−アルキルシリル、C1〜C6−アルコキシカルボニル、アミノ−カルボニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノカルボニル、アミノスルホニル、N−モノ−もしくはN,N−ジ−C1〜C6−アルキルアミノスルホニル、N−C1〜C6−アルキルスルホニルアミノ、C1〜C6−アルコキシカルボニルアミノ、N−C1〜C4−アルキル−N−C1〜C6−アルコキシカルボニルアミノ、シアノ、ニトロ、および非置換もしくはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、C1〜C4−アルコキシ−、C1〜C4−ハロアルコキシ−、アミノ−、シアノ−もしくはニトロ−置換C3〜C6−ヘテロシクリルから成る群から選択される1つまたは複数の同じまたは異なる基によって置換されるフェニルであり、および
A’はC1〜C6−アルキルであり、C1〜C6−ハロアルキルであり、C3−C6−シクロアルキルであり、C3〜C6−ハロシクロアルキルであり、B、N、OおよびSから成る群から選択される1〜3個の同じまたは異なるヘテロ原子を有する5または6員のヘテロシクロアルキルであり、ハロゲン、C1〜C4−アルキルまたはC1〜C4−アルコキシによってさらに置換されないまたは置換され、ヘテロ芳香族基であり、ハロゲン、シアノ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−ハロアルコキシ、C1〜C4−アルカノイル、5もしくは6員のヘテロシクロ−アルキル−C1〜C2−アルキルまたは非置換もしくはハロゲン−、C1〜C4−アルキル−またはC1〜C4−アルコキシ−置換フェニルによってさらに置換されないまたは置換され、または合計8〜10個の環員を含むヘテロ二環式環基であり、1〜5個、好ましくは1または2個の員はB、N、OおよびSから成る群から選択される同じまたは異なるヘテロ原子であり、0〜2個の員は、-C(O)−基であり、二環式環基はハロゲン、シアノ、ヒドロキシル、C1〜C4−アルキルまたはC1〜C4−ハロアルキルによってさらに置換されないまたは置換される、前記化合物。 - 請求項2に記載の化合物であって、Y’はハロゲンまたはCF3から選択される2または3個の同じまたは異なる基によって置換されるフェニルであり、A’はC1〜C4−アルキル、CF3、ピロリジニル、ピペラジニル、モルホリニルまたはジオキサボロラニルであり、それぞれメチル、ピリル、ピラゾリル、トリアゾリル、チエニル、チアジニル、チアゾリル、ピリジルまたはピリミジニルによって置換されないまたは置換され、それぞれ、ハロゲン、シアノ、C1〜C2−アルキル、C1〜C2−アルコキシ、C1〜C2−ハロアルキル、アセチル、プロピオニル、フェニルまたはモルホリン−4−イル−メチル、またはインドリル、ベンゾピラゾリルまたはベンゾチアゾリルによって置換されないまたは置換され、それぞれメチルによって置換されないまたは置換され、nが1である、前記化合物。
- 式
Aはハロゲン、C1〜C6−アルキル、C1〜C6−ハロアルキル、C3〜C6−シクロアルキル、C3〜C6−ハロシクロアルキル、C1〜C6−アルコキシ、C1〜C6−ハロアルコキシ、C1〜C6−アルキルチオ、C1〜C6−ハロアルキルチオ、C1〜C6−アルキル−スルフィニル、C1〜C6−ハロアルキルスルフィニル、C1〜C6−アルキルスルホニル、C1〜C6−ハロアルキルスルホニル、SF5、アミノ、N−モノ−またはN,N−ジ−C1〜C6−アルキルアミノ、トリ−C1〜C4−アルキルシリル、C1〜C6−アルコキシカルボニル、アミノカルボニル、N−モノ−またはN,N−ジ−C1〜C6−アルキルアミノカルボニル、アミノスルホニル、N−モノ−またはN,N−ジ−C1〜C6−アルキルアミノスルホニル、C1〜C6−アルコキシカルボニルアミノ、N−C1〜C4−アルキル−N−C1〜C6−アルコキシカルボニルアミノ、シアノ、ニトロ、または非置換もしくはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、C1〜C4−アルコキシ−、C1〜C4−ハロアルコキシ−、アミノ−、シアノ−もしくはニトロ−置換C3〜C6−ヘテロシクリルによって置換されないまたは置換されるフェニルであり、
Yはハロゲン、C1〜C6−アルキル、C1〜C6−ハロアルキル、C3〜C6−シクロアルキル、C3〜C6−ハロシクロアルキル、ヒドロキシル、C1〜C6−アルコキシ、C1〜C6−ハロアルコキシ、C1〜C6−アルキルチオ、C1〜C6−ハロアルキルチオ、C1〜C6−アルキル−スルフィニル、C1〜C6−ハロアルキルスルフィニル、C1〜C6−アルキルスルホニル、C1〜C6−ハロアルキルスルホニル、SF5、アミノ、N−モノ−またはN,N−ジ−C1〜C6−アルキルアミノ、トリ−C1〜C4−アルキルシリル、C1〜C6−アルコキシカルボニル、アミノカルボニル、N−モノ−またはN,N−ジ−C1〜C6−アルキルアミノカルボニル、アミノスルホニル、N−モノ−またはN,N−ジ−C1〜C6−アルキルアミノスルホニル、N−C1〜C6−アルキルスルホニルアミノ、C1〜C6−アルコキシカルボニルアミノ、N−C1〜C6−アルキル−N−C1〜C4−アルコキシカルボニルアミノ、シアノ、ニトロ、および非置換またはハロゲン−、C1〜C4−アルキル−、C1〜C4−ハロアルキル−、C1〜C4−アルコキシ−、C1〜C4−ハロアルコキシ−、アミノ−、シアノ−もしくはニトロ−置換C3〜C6−ヘテロシクリルから成る群から選択される1つまたは複数の同じまたは異なる基によって置換されるフェニルであり、
TはC2〜C6−アルキルであり、ハロゲン、トリメチルシリル、C3〜C6−シクロアルキル、カルボキシまたはC1〜C4−アルコキシカルボニルによって置換されないまたは置換され、C3〜C6−シクロアルキルであり、C6〜C12−ビカルボシクリルであり、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキルまたはC1〜C4−アルコキシによって置換されないまたは置換されるフェニルであり、5もしくは6員のヘテロ芳香族基であり、ハロゲン、C1〜C4−アルキルまたはC1〜C4−アルコキシによってさらに置換されないまたは置換され、アミノであり、N−モノ−もしくはN,N−ジ−C1〜C4−アルキルアミノであり、N、O、SおよびS(O2)から成る群から選択される1〜3個の同じまたは異なるヘテロ原子を有する5または6員のヘテロシクロアルキルであり、C1〜C4−アルキルによってさらに置換されないまたは置換され、または基
R3はC1〜C4−アルキル、非置換またはハロゲン−、C1〜C4−アルキル−もしくはC1〜C4−ハロアルキル置換フェニル、非置換またはハロゲン−、C1〜C4−アルキル−またはC1〜C4−ハロアルキル置換ピリジル、C1〜C4−アルコキシ−カルボニル−メチルまたはモルホリン−4−yl−カルボニルメチルである、前記化合物。 - 請求項4に記載の化合物であって、Aは塩素、フッ素またはCF3によって置換されないまたは一置換されるフェニルであり、YはハロゲンまたはCF3から選択される2または3個の同じもしくは異なる基によって置換されるフェニルであり、TはC2〜C4−アルキルであり、ハロゲン、シクロプロピル、シクロヘキシル、トリメチルシリル、カルボキシまたはC1〜C2−アルコキシカルボニによって置換されないまたは置換され、シクロプロピルまたはシクロヘキシルであり、(+)−または(−)−カンフルの基であり、フッ素、塩素、メチル、メトキシ、CF3またはニトロによって置換されないまたは置換されるフェニルであり、またはピリジル、チエニルもしくはピリミジニルであり、ピペリジニル、ピペラジニル、テトラヒドロピラニル、モルホリニル、チオモルホリニルまたはチオモルホリン−4−イル−1,1−ジオキシドであり、それぞれメチルまたはベンジルオキシカルボニルによって置換されないまたは置換される、前記化合物。
- 式
Aは請求項1に記載の置換されないまたは置換されるフェニルであり、
R0はHまたはヒドロキシルであり、
Y’’は
(i)5または6員のヘテロアリールまたはヘテロアリールアミノであり、それぞれ、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−アルコキシカルボニル、C1〜C4−アルカノイルまたはそれぞれハロゲン、シアノ、ニトロメチルもしくはメトキシによって置換されないまたは置換されるフェニルもしくはフェニルスルホニルによってさらに置換されないまたは置換され、
(ii)ベンゾイルまたは5または6員のヘテロアリールカルボニルであり、それぞれ、ハロゲン、シアノ、ニトロ、C1〜C4−アルキル、C1〜C4−ハロアルキル、C1〜C4−アルコキシ、C1〜C4−アルコキシカルボニル、C1〜C4−アルカノイルまたはフェニルによってさらに置換されないまたは置換され、
(iii)C6〜C12−二炭素環式基であり、または
(iv)合計8〜10個の環員を含むヘテロ二環式環基であり、1〜5個、好ましくは1または2個の員はB、N、OおよびSから成る群から選択される同じまたは異なるヘテロ原子であり、0〜2個の員は-C(O)−基であり、二環式環基はハロゲン、シアノ、ヒドロキシル、C1〜C4−アルコキシ、C1〜C4−アルキルまたはC1〜C4−ハロアルキルによってさらに置換されないまたは置換され、または
(v)-H2C−C(O)−NH−R4基であり、ここでR4はC1〜C4−ハロアルキル、C2〜C3−アルキニルまたはシアノ−C1〜C4−アルキルであり、または
R0およびYはそれらが結合されるN原子と一緒になって、C1〜C4−アルキル、C1〜C4−アルコキシ非置換またはハロゲン−、C1〜C4−アルキル−、ハロ−C1〜C4−アルキル−、アミノ−および/またはC1〜C4−アルコキシ置換フェニルもしくはベンゾイルアミノまたは非置換もしくはC1〜C4−アルキル−、C1〜C4−ハロアルキル−、C3〜C6−シクロアルキル−またはハロゲン−置換ピリジルもしくはピリミジニルによって置換されるピペリジニルまたはピペラジニル基を形成する、前記化合物。 - 請求項6に記載の化合物であって、
Aは塩素、フッ素またはCF3によって非置換または一置換されるフェニルであり、
R0はHであり、
Y’’は
(i)ハロゲン、C1〜C4−アルキルまたはC1〜C2−アルコキシによって置換される2−、3−または4−ピリジルであり、C1〜C2−アルキル、C1〜C2−アルコキシカルボニルによって置換されないまたは置換される2−チエニルであり、ハロゲン、シアノ、ニトロ、C1〜C2−アルキル、C1〜C2−ハロアルキル、C1〜C2−アルコキシカルボニル、またはそれぞれ順番にハロゲン、シアノ、ニトロもしくはメチルによって置換されないまたは置換されるフェニルもしくはフェニルスルホニルによって置換されないまたは置換される2−チアゾリルであり、ハロゲンまたはメチルによって置換されないまたは置換される5−イソチアゾイルであり、C1〜C2−アルキルまたはC1〜C2−ハロアルキルによって置換されないまたは置換される2−オキサゾリルであり、またはC1〜C2−アルキルまたはC1〜C2−ハロアルキルよって置換されないまたは置換される1,3,4−チアジアゾール−5−イルであり、またはハロゲン、C1−C4−アルキルまたはC1−C2−アルコキシによって置換されないまたは置換される2−、3−または4−ピリジルアミノであり、または
(ii)ハロゲンによって置換されないまたは置換されるベンゾイルであり、またはハロゲンもしくはC1〜C4−アルキルによって置換されないまたは置換される2−、3−もしくは4−ピリジルカルボニルであり、または
(iii)基、
(iv)ベンゾチアゾリル、インドリル、キノリニル、メチレンジオキソ−フェニル、ベンゾオキサボロニル、トリアゾロピリミジノニルまたはフタルヒドラジジルであり、それぞれハロゲン、C1〜C4−アルキル、C1〜C2−ハロアルキルまたはヒドロキシによって置換されないまたは置換され、または
(v)-H2C−C(O)−NH−CH2−C≡CH基、-H2C−C(O)−NH−CH2−CN基または-H2C−C(O)−NH−CH2−CF3基であり、または
R0およびYはそれらが結合されるN原子と一緒になって、ピペリジニルもしくはピペラジニル基を形成し、メチル、メトキシ、ハロゲン−、アミノ−、メトキシ−もしくはトリフルオロメチル置換フェニルまたはベンゾイルアミノ、またはハロゲン−、トリフルオロメチル−および/もしくはシクロプロピル置換ピリジルまたはピリミジニルによって置換される、前記化合物。 - 担体および/または分散剤の他に、有効成分として請求項1〜7のいずれか1項に記載の式(I)、(Ia)、(Ib)または(Ic)の少なくとも一つの化合物を含む、寄生虫を制御するための組成物。
- 温血動物の体内または表面の内部寄生虫を制御するために使用する、請求項1〜7のいずれか1項に記載の式(I)、(Ia)、(Ib)または(Ic)の化合物。
- 温血動物に、獣医学的に有効量の請求項1〜7のいずれか1項に記載の式(I)、(Ia)、(Ib)または(Ic)の少なくとも一つの化合物を投与することを含む、温血動物の内部寄生虫を制御する方法。
- 温血動物の体内または表面の内部寄生虫に対する獣医学的または医薬組成物の調製における、請求項1〜7のいずれか1項に記載の式(I)、(Ia)、(Ib)または(Ic)の化合物の使用。
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