JP2019535706A5 - - Google Patents
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- JP2019535706A5 JP2019535706A5 JP2019524276A JP2019524276A JP2019535706A5 JP 2019535706 A5 JP2019535706 A5 JP 2019535706A5 JP 2019524276 A JP2019524276 A JP 2019524276A JP 2019524276 A JP2019524276 A JP 2019524276A JP 2019535706 A5 JP2019535706 A5 JP 2019535706A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- halogen atoms
- halogenoalkyl
- group
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000005843 halogen group Chemical group 0.000 claims 284
- 229910052736 halogen Inorganic materials 0.000 claims 150
- 150000002367 halogens Chemical group 0.000 claims 142
- 229910052739 hydrogen Inorganic materials 0.000 claims 114
- 239000001257 hydrogen Substances 0.000 claims 113
- 125000004093 cyano group Chemical group *C#N 0.000 claims 98
- 125000001424 substituent group Chemical group 0.000 claims 82
- 150000002431 hydrogen Chemical group 0.000 claims 81
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 74
- -1 -OH Chemical group 0.000 claims 63
- 150000001875 compounds Chemical class 0.000 claims 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 47
- 229910052731 fluorine Inorganic materials 0.000 claims 45
- 239000011737 fluorine Substances 0.000 claims 45
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 42
- 125000004043 oxo group Chemical group O=* 0.000 claims 39
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 35
- 125000001072 heteroaryl group Chemical group 0.000 claims 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 34
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 31
- 229910052801 chlorine Inorganic materials 0.000 claims 30
- 239000000460 chlorine Chemical group 0.000 claims 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 29
- 229910052799 carbon Inorganic materials 0.000 claims 27
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 18
- 229910052717 sulfur Inorganic materials 0.000 claims 18
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 17
- 125000002950 monocyclic group Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 150000001204 N-oxides Chemical class 0.000 claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 238000006467 substitution reaction Methods 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 2
- WNBQDDAKLKODPH-UHFFFAOYSA-N 1,2,4-triazolidine Chemical compound C1NCNN1 WNBQDDAKLKODPH-UHFFFAOYSA-N 0.000 claims 2
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 2
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical compound C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims 2
- CGYYAUFHKJHMCK-UHFFFAOYSA-N 3,9-dioxa-7-azabicyclo[3.3.1]nonane Chemical compound C1OCC2CNCC1O2 CGYYAUFHKJHMCK-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 2
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 1
- ZKRNFYHDRLBLJL-UHFFFAOYSA-N 4-oxa-7-azaspiro[2.5]octane Chemical compound C1CC11OCCNC1 ZKRNFYHDRLBLJL-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- WDJAQSJMDRFZIX-UHFFFAOYSA-N 6-oxa-3-azabicyclo[3.1.1]heptane Chemical compound C1NCC2CC1O2 WDJAQSJMDRFZIX-UHFFFAOYSA-N 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 206010061201 Helminthic infection Diseases 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 230000000507 anthelmentic effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 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 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- NXZIGGBPLGAPTI-UHFFFAOYSA-N tert-butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC2OC21 NXZIGGBPLGAPTI-UHFFFAOYSA-N 0.000 claims 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 0 Cc1c(*)c(C)nc(*)c1* Chemical compound Cc1c(*)c(C)nc(*)c1* 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16198550.2 | 2016-11-11 | ||
| EP16198550 | 2016-11-11 | ||
| PCT/EP2017/078319 WO2018087036A1 (en) | 2016-11-11 | 2017-11-06 | New anthelmintic quinoline-3-carboxamide derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019535706A JP2019535706A (ja) | 2019-12-12 |
| JP2019535706A5 true JP2019535706A5 (enExample) | 2020-12-17 |
| JP7165129B2 JP7165129B2 (ja) | 2022-11-02 |
Family
ID=57321155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019524276A Active JP7165129B2 (ja) | 2016-11-11 | 2017-11-06 | 新規な駆虫性キノリン－３－カルボキサミド誘導体 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US10889573B2 (enExample) |
| EP (1) | EP3538512B1 (enExample) |
| JP (1) | JP7165129B2 (enExample) |
| KR (1) | KR102595730B1 (enExample) |
| CN (1) | CN109890793B (enExample) |
| AU (1) | AU2017357503B2 (enExample) |
| CA (1) | CA3043298A1 (enExample) |
| CL (1) | CL2019001292A1 (enExample) |
| CO (1) | CO2019004776A2 (enExample) |
| DK (1) | DK3538512T3 (enExample) |
| DO (1) | DOP2019000117A (enExample) |
| ES (1) | ES2884073T3 (enExample) |
| IL (1) | IL266407B (enExample) |
| MX (1) | MX2019005569A (enExample) |
| MY (1) | MY196327A (enExample) |
| NZ (1) | NZ752550A (enExample) |
| PH (1) | PH12019501034A1 (enExample) |
| PL (1) | PL3538512T3 (enExample) |
| PT (1) | PT3538512T (enExample) |
| SG (1) | SG11201903059SA (enExample) |
| SI (1) | SI3538512T1 (enExample) |
| TW (1) | TWI821165B (enExample) |
| UA (1) | UA126119C2 (enExample) |
| UY (1) | UY37480A (enExample) |
| WO (1) | WO2018087036A1 (enExample) |
| ZA (1) | ZA201903708B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3068350A1 (en) | 2017-06-30 | 2019-01-03 | Bayer Animal Health Gmbh | New azaquinoline derivatives |
| US11254661B2 (en) * | 2017-08-04 | 2022-02-22 | Bayer Animal Health Gmbh | Quinoline derivatives for treating infections with helminths |
| EP3692037A1 (en) * | 2017-12-15 | 2020-08-12 | Bayer Animal Health GmbH | Process for preparing antihelmintic 4-amino-quinoline-3-carboxamide derivatives |
| SG11202010024UA (en) * | 2018-05-09 | 2020-11-27 | Bayer Animal Health Gmbh | New quinoline derivatives |
| WO2020014068A1 (en) | 2018-07-09 | 2020-01-16 | Boehringer Ingelheim Animal Health USA Inc. | Anthelminthic heterocyclic compounds |
| EP3643711A1 (en) * | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
| PL3897842T3 (pl) * | 2018-12-18 | 2025-05-19 | Elanco Tiergesundheit Ag | Pochodne bicykliczne |
| NZ777370A (en) * | 2018-12-18 | 2024-11-29 | Elanco Tiergesundheit Ag | Bicyclic derivatives |
| CA3133100A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| US12448391B2 (en) | 2019-06-07 | 2025-10-21 | Elanco Tiergesundheit Ag | Bicyclic derivatives for treating endoparasites |
| TWI865563B (zh) * | 2019-07-30 | 2024-12-11 | 德商拜耳動物保健有限公司 | 新穎異喹啉衍生物 |
| WO2021122906A1 (en) | 2019-12-18 | 2021-06-24 | Intervet International B.V. | Anthelmintic compounds comprising azaindoles structure |
| CA3164098A1 (en) * | 2019-12-18 | 2021-06-24 | Intervet International B.V. | Anthelmintic compounds comprising a quinoline structure |
| WO2021204930A1 (en) | 2020-04-09 | 2021-10-14 | Bayer Animal Health Gmbh | Substituted condensed azines as anthelmintic compounds |
| AU2021278889A1 (en) | 2020-05-29 | 2023-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelmintic heterocyclic compounds |
| CN116685584A (zh) * | 2020-11-18 | 2023-09-01 | 礼蓝动物保健有限公司 | 用于治疗心丝虫感染的n-(2,3-二氢-1,4-苯并噁嗪-4-基)-3-异丙基-7-(2,3,5-三氟苯基)苯并噻吩-2-甲酰胺衍生物和类似化合物 |
| JP2023553269A (ja) | 2020-11-18 | 2023-12-21 | エランコ・ティアゲゾンタイト・アーゲー | イヌ糸状虫感染症を治療するためのｎ－（２，３－ジヒドロ－１，４－ベンゾオキサジン－４－イル）－３－イソプロピル－７－（２，３，５－トリフルオロフェニル）ベンゾ－チオフェン－２－カルボキサミド誘導体及び類似化合物 |
| TW202237600A (zh) * | 2020-12-04 | 2022-10-01 | 瑞士商禮藍動物保健股份有限公司 | 雙環衍生物 |
| CN116888124A (zh) * | 2020-12-04 | 2023-10-13 | 礼蓝动物保健有限公司 | 二环衍生物 |
| US20240043446A1 (en) | 2020-12-11 | 2024-02-08 | Intervet Inc. | Anthelmintic compounds comprising a thienopyridine structure |
| US20240043385A1 (en) | 2020-12-11 | 2024-02-08 | Intervet Inc. | Anthelmintic compounds comprising a pyridine structure |
| EP4148052A1 (en) | 2021-09-09 | 2023-03-15 | Bayer Animal Health GmbH | New quinoline derivatives |
| UY39995A (es) | 2021-11-01 | 2023-05-15 | Boehringer Ingelheim Vetmedica GmbH | Compuestos de pirrolopiridazina como antihelmínticos |
| WO2024213752A1 (en) | 2023-04-14 | 2024-10-17 | Elanco Animal Health Gmbh | Long-term prevention and/or treatment of a disease by slo-1 inhibitors |
| WO2025027117A1 (en) | 2023-08-02 | 2025-02-06 | Intervet International B.V. | Carboxamide-4-quinoline compounds with anthelmintic activity |
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| KR840000768A (ko) * | 1982-07-23 | 1984-02-27 | 박이은 | 무연통의 무연탄 난로 |
| DE3639877A1 (de) | 1986-11-21 | 1988-05-26 | Bayer Ag | Hetarylalkyl substituierte 5- und 6-ringheterocyclen |
| US6559145B2 (en) | 2000-07-12 | 2003-05-06 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
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