JPWO2020219871A5 - - Google Patents
Download PDFInfo
- Publication number
- JPWO2020219871A5 JPWO2020219871A5 JP2021563666A JP2021563666A JPWO2020219871A5 JP WO2020219871 A5 JPWO2020219871 A5 JP WO2020219871A5 JP 2021563666 A JP2021563666 A JP 2021563666A JP 2021563666 A JP2021563666 A JP 2021563666A JP WO2020219871 A5 JPWO2020219871 A5 JP WO2020219871A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- pharmaceutically acceptable
- compound
- acceptable salt
- 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
Links
- 150000003839 salts Chemical class 0.000 claims 57
- 150000001875 compounds Chemical class 0.000 claims 56
- -1 pyrrolidyl Chemical group 0.000 claims 54
- 125000000623 heterocyclic group Chemical group 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 13
- 125000005936 piperidyl group Chemical group 0.000 claims 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 241000002163 Mesapamea fractilinea Species 0.000 claims 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 238000006467 substitution reaction Methods 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 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 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 9
- 239000003795 chemical substances by application Substances 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 230000000155 isotopic effect Effects 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000002757 morpholinyl group Chemical group 0.000 claims 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 5
- 229910052727 yttrium Inorganic materials 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical class CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 4
- 239000003096 antiparasitic agent Substances 0.000 claims 4
- 229940125687 antiparasitic agent Drugs 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004069 aziridinyl group Chemical group 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000003566 oxetanyl group Chemical group 0.000 claims 3
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims 2
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims 2
- 208000006968 Helminthiasis Diseases 0.000 claims 2
- 208000015336 Helminthic disease Diseases 0.000 claims 2
- 206010061201 Helminthic infection Diseases 0.000 claims 2
- 241000604961 Wolbachia Species 0.000 claims 2
- RCKMWOKWVGPNJF-UHFFFAOYSA-N diethylcarbamazine Chemical compound CCN(CC)C(=O)N1CCN(C)CC1 RCKMWOKWVGPNJF-UHFFFAOYSA-N 0.000 claims 2
- 229960003974 diethylcarbamazine Drugs 0.000 claims 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 2
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 229960002418 ivermectin Drugs 0.000 claims 2
- 230000004899 motility Effects 0.000 claims 2
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 230000008685 targeting Effects 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.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 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims 1
- NQPDXQQQCQDHHW-UHFFFAOYSA-N 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole Chemical compound ClC=1C=C2NC(SC)=NC2=CC=1OC1=CC=CC(Cl)=C1Cl NQPDXQQQCQDHHW-UHFFFAOYSA-N 0.000 claims 1
- 239000005660 Abamectin Substances 0.000 claims 1
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims 1
- AQXXZDYPVDOQEE-MXDQRGINSA-N Pyrantel pamoate Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1.C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 AQXXZDYPVDOQEE-MXDQRGINSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 229950008167 abamectin Drugs 0.000 claims 1
- YQNQNVDNTFHQSW-UHFFFAOYSA-N acetic acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] ester Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 YQNQNVDNTFHQSW-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229960002669 albendazole Drugs 0.000 claims 1
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 claims 1
- 229960003722 doxycycline Drugs 0.000 claims 1
- XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 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 claims 1
- 229960001575 emodepside Drugs 0.000 claims 1
- 108010056417 emodepside Proteins 0.000 claims 1
- 229960005473 fenbendazole Drugs 0.000 claims 1
- IRHZVMHXVHSMKB-UHFFFAOYSA-N fenbendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 IRHZVMHXVHSMKB-UHFFFAOYSA-N 0.000 claims 1
- CPEUVMUXAHMANV-UHFFFAOYSA-N flubendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=C(F)C=C1 CPEUVMUXAHMANV-UHFFFAOYSA-N 0.000 claims 1
- 229960004500 flubendazole Drugs 0.000 claims 1
- 229960001614 levamisole Drugs 0.000 claims 1
- 229960003439 mebendazole Drugs 0.000 claims 1
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- WTERNLDOAPYGJD-SFHVURJKSA-N monepantel Chemical compound C([C@@](C)(NC(=O)C=1C=CC(SC(F)(F)F)=CC=1)C#N)OC1=CC(C#N)=CC=C1C(F)(F)F WTERNLDOAPYGJD-SFHVURJKSA-N 0.000 claims 1
- 229950003439 monepantel Drugs 0.000 claims 1
- 229960004816 moxidectin Drugs 0.000 claims 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 claims 1
- 229960001920 niclosamide Drugs 0.000 claims 1
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 claims 1
- 229960002480 nitazoxanide Drugs 0.000 claims 1
- BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 claims 1
- 229960004454 oxfendazole Drugs 0.000 claims 1
- 229950003126 oxyclozanide Drugs 0.000 claims 1
- JYWIYHUXVMAGLG-UHFFFAOYSA-N oxyclozanide Chemical compound OC1=C(Cl)C=C(Cl)C=C1NC(=O)C1=C(O)C(Cl)=CC(Cl)=C1Cl JYWIYHUXVMAGLG-UHFFFAOYSA-N 0.000 claims 1
- 229960002957 praziquantel Drugs 0.000 claims 1
- 229960000996 pyrantel pamoate Drugs 0.000 claims 1
- 229960002245 selamectin Drugs 0.000 claims 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 claims 1
- 229960005314 suramin Drugs 0.000 claims 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 claims 1
- 238000003419 tautomerization reaction Methods 0.000 claims 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims 1
- 229960004546 thiabendazole Drugs 0.000 claims 1
- 239000004308 thiabendazole Substances 0.000 claims 1
- 235000010296 thiabendazole Nutrition 0.000 claims 1
- 229960000323 triclabendazole Drugs 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962839552P | 2019-04-26 | 2019-04-26 | |
| US62/839,552 | 2019-04-26 | ||
| PCT/US2020/029805 WO2020219871A1 (en) | 2019-04-26 | 2020-04-24 | Heterocyclic compounds and their use for treatment of helminthic infections and diseases |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2022529541A JP2022529541A (ja) | 2022-06-22 |
| JP2022529541A5 JP2022529541A5 (https=) | 2023-04-13 |
| JPWO2020219871A5 true JPWO2020219871A5 (https=) | 2023-04-13 |
| JP7546596B2 JP7546596B2 (ja) | 2024-09-06 |
Family
ID=70775481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021563666A Active JP7546596B2 (ja) | 2019-04-26 | 2020-04-24 | ヘテロ環式化合物ならびに蠕虫感染および疾患におけるその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US11505548B2 (https=) |
| EP (1) | EP3959207A1 (https=) |
| JP (1) | JP7546596B2 (https=) |
| KR (1) | KR102939516B1 (https=) |
| CN (1) | CN114072395A (https=) |
| WO (1) | WO2020219871A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2019301510B2 (en) | 2018-07-09 | 2024-06-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelminthic heterocyclic compounds |
| CA3133100A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| US11505548B2 (en) * | 2019-04-26 | 2022-11-22 | Celgene Corporation | Heterocyclic compounds and their use for treatment of helminthic infections and diseases |
| EP4077322A1 (en) | 2019-12-18 | 2022-10-26 | Intervet International B.V. | Anthelmintic compounds comprising azaindoles structure |
| AU2020406093A1 (en) | 2019-12-18 | 2022-06-16 | Intervet International B.V. | Anthelmintic compounds comprising a quinoline structure |
| KR20230028268A (ko) | 2020-05-29 | 2023-02-28 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 헤테로시클릭 화합물 |
| KR20230043904A (ko) | 2020-07-24 | 2023-03-31 | 엘랑코 유에스 인코포레이티드 | 이속사졸린 화합물 및 이의 중간체의 제조 공정 |
| CN116744917A (zh) | 2020-09-04 | 2023-09-12 | 礼蓝美国公司 | 适口调配物 |
| US20240025891A1 (en) * | 2020-10-23 | 2024-01-25 | Celgene Corporation | Heterocyclic compounds and their use for treatment of helminthic infections and diseases |
| US20240043446A1 (en) | 2020-12-11 | 2024-02-08 | Intervet Inc. | Anthelmintic compounds comprising a thienopyridine structure |
| CN112500324B (zh) * | 2020-12-12 | 2022-05-13 | 浙江大学衢州研究院 | 制备硫代酰胺类化合物的方法 |
| US20240148744A1 (en) * | 2021-02-09 | 2024-05-09 | Celgene Corporation | Sulfonamides and their use for treatment of helminthic infections and diseases |
| UY39995A (es) | 2021-11-01 | 2023-05-15 | Boehringer Ingelheim Vetmedica GmbH | Compuestos de pirrolopiridazina como antihelmínticos |
| CN115819429A (zh) * | 2022-12-13 | 2023-03-21 | 成都睿智化学研究有限公司 | 一种5-氯-2,3-二氢呋喃[2,3-c]吡啶的合成方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA879329B (en) * | 1986-12-12 | 1988-06-13 | Ciba-Geigy Ag | Pesticides |
| US4871753A (en) | 1986-12-12 | 1989-10-03 | Ciba-Geigy Corporation | 3-Phenyl-5-trifluoromethyl-1,2,4-oxadiazole compounds which are useful pesticides |
| ES2140543T3 (es) | 1993-08-13 | 2000-03-01 | Zeneca Ltd | Derivados de tia- y oxadiazol y su uso como fungicidas o insecticidas. |
| US5614470A (en) | 1994-04-01 | 1997-03-25 | Sankyo Company, Limited | 13-substituted milbemycin derivatives, their preparation and their use |
| JP3689462B2 (ja) * | 1994-11-17 | 2005-08-31 | 三共アグロ株式会社 | 殺虫活性を有する１３位置換ミルベマイシン誘導体 |
| CN1915016B (zh) | 1995-11-08 | 2010-12-22 | 默沙东公司 | 农药制剂 |
| HU228375B1 (en) | 1995-11-08 | 2013-03-28 | Merck Sharp & Dohme | Pesticidal formulation |
| DE19858193A1 (de) * | 1998-12-17 | 2000-06-21 | Aventis Cropscience Gmbh | 4-Trifluormethyl-3-oxadiazolylpyridine, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
| US6310049B1 (en) | 1998-08-11 | 2001-10-30 | Nihon Bayer Agrochem K.K. | Nematicidal pyrazoles |
| EP1954696B1 (en) * | 2005-01-19 | 2011-02-23 | Bristol-Myers Squibb Company | 2-phenoxy-n-(1,3,4-thiadizol-2-yl)pyridin-3-amine derivatives and related compounds as p2y1 receptor inhibitors for the treatment of thromboembolic disorders |
| CL2008000979A1 (es) | 2007-04-11 | 2008-10-17 | Sumitomo Chemical Co | Proceso para producir un compuesto derivado de 2-piridin-2-il-2h-pirazol-3-fenilamida; compuestos intermediarios; el compuesto en si; composicion plaguicida que contiene a dicho compuesto; uso de dicho compuesto como plaguicida; y metodo para control |
| TW201210597A (en) * | 2010-06-09 | 2012-03-16 | Gilead Sciences Inc | Inhibitors of hepatitis C virus |
| EP2651405A2 (en) * | 2010-12-14 | 2013-10-23 | Electrophoretics Limited | Casein kinase 1 (ck1 ) inhibitors |
| US11505548B2 (en) * | 2019-04-26 | 2022-11-22 | Celgene Corporation | Heterocyclic compounds and their use for treatment of helminthic infections and diseases |
-
2020
- 2020-04-24 US US16/858,410 patent/US11505548B2/en active Active
- 2020-04-24 WO PCT/US2020/029805 patent/WO2020219871A1/en not_active Ceased
- 2020-04-24 CN CN202080046747.4A patent/CN114072395A/zh active Pending
- 2020-04-24 KR KR1020217038203A patent/KR102939516B1/ko active Active
- 2020-04-24 JP JP2021563666A patent/JP7546596B2/ja active Active
- 2020-04-24 EP EP20726997.8A patent/EP3959207A1/en active Pending
-
2022
- 2022-10-04 US US17/960,046 patent/US12338235B2/en active Active
-
2025
- 2025-05-16 US US19/211,032 patent/US20250276967A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPWO2020219871A5 (https=) | ||
| JP7579402B2 (ja) | 癌治療用ｐｔｐｎ１１（ｓｈｐ２）阻害剤としての６－（４－アミノ－３－メチル－２－オキサ－８－アザスピロ［４．５］デカン－８－イル）－３－（２，３－ジクロロフェニル）－２－メチルピリミジン－４（３ｈ）－オン誘導体及び関連化合物 | |
| AU2015352603B2 (en) | New substituted indazoles, methods for the production thereof, pharmaceutical preparations that contain said new substituted indazoles, and use of said new substituted indazoles to produce drugs | |
| AU2016226468B2 (en) | TGF-beta inhibitors | |
| DE69709727T2 (de) | Parazinon thrombin inhibitoren | |
| CA2984259C (en) | Combinations of inhibitors of irak4 with inhibitors of btk | |
| CA2832123C (en) | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts | |
| JP6117999B2 (ja) | テトラヒドロシクロペンタピロール誘導体およびその製造方法 | |
| ES2732902T3 (es) | Bencimidazol-2-aminas como inhibidores de MIDH1 | |
| WO2018136634A1 (en) | Fused heterocyclic compounds as selective bmp inhibitors | |
| TW201842919A (zh) | 經修飾環二核苷酸化合物 | |
| CN106986856A (zh) | 作为用于治疗疾病诸如癌症的nampt抑制剂的4‑{[(吡啶‑3‑基‑甲基)氨基羰基]氨基}苯‑砜衍生物 | |
| JP2020510015A5 (https=) | ||
| MA27475A1 (fr) | Composes de pyrazolo [3,4-b] pyridine et leur utilisation en tant qu'inhibiteurs de phosphodiesterase | |
| EP3221318B1 (en) | Fused imidazole derivatives as tgf-beta inhibitors | |
| EA031655B1 (ru) | Бензимидазол-2-амины в качестве ингибиторов midhi | |
| RU2004109812A (ru) | Ингибиторы цистеинпротеазы 2-циано-4-аминопиримидинового строения с ингибирующим действием на катепсин к для лечения воспалительных и других заболеваний | |
| JP2007519694A5 (https=) | ||
| RU2013114848A (ru) | Гуанидиновые соединения и композиции для ингибирования nampt | |
| CA2749040A1 (en) | Triazolo and tetrazolo pyrimidine derivatives as hne inhibitors for treating copd | |
| EP2588107A1 (en) | COMBINATION OF A cMET INHIBITOR AND AN ANTIBODY TO HGF AND/OR cMET | |
| CN101918079A (zh) | 蛋白激酶抑制剂及其用途 | |
| KR101010871B1 (ko) | 시아노구아니딘 프로드럭 | |
| US3457269A (en) | N-substituted phenyl and n-substituted phenylalkyl 3 - indazolecarboxamides and preparation thereof | |
| ES2292820T3 (es) | 2-(3-sulfonilamino-2-oxopyrrolidin-1-yl)propanamidas como inhibidores del factor xa. |