JPWO2022087326A5 - - Google Patents
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- JPWO2022087326A5 JPWO2022087326A5 JP2023524715A JP2023524715A JPWO2022087326A5 JP WO2022087326 A5 JPWO2022087326 A5 JP WO2022087326A5 JP 2023524715 A JP2023524715 A JP 2023524715A JP 2023524715 A JP2023524715 A JP 2023524715A JP WO2022087326 A5 JPWO2022087326 A5 JP WO2022087326A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- pharma
- tautomer
- stereoisomer
- 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.)
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- 150000003839 salts Chemical class 0.000 claims 69
- 150000001875 compounds Chemical class 0.000 claims 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 49
- -1 2-pyrimidyl Chemical group 0.000 claims 39
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 125000001424 substituent group Chemical group 0.000 claims 26
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 25
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 21
- 239000003814 drug Substances 0.000 claims 18
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 229940079593 drug Drugs 0.000 claims 11
- 125000004193 piperazinyl group Chemical group 0.000 claims 11
- 125000005936 piperidyl group Chemical group 0.000 claims 11
- 241000002163 Mesapamea fractilinea Species 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 208000006968 Helminthiasis Diseases 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 8
- 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 6
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000015181 infectious disease Diseases 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 241000604961 Wolbachia Species 0.000 claims 2
- 230000000507 anthelmentic effect Effects 0.000 claims 2
- 239000000921 anthelmintic agent Substances 0.000 claims 2
- 125000004069 aziridinyl group Chemical group 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
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- 230000004899 motility Effects 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 1
- 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
- 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 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
- 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 1
- 239000005660 Abamectin Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- UYPBHECWVMHJQR-UHFFFAOYSA-N N-(5-chloropyridin-2-yl)-4-pyrimidin-2-yl-1,3-thiazol-2-amine Chemical compound Clc1ccc(Nc2nc(cs2)-c2ncccn2)nc1 UYPBHECWVMHJQR-UHFFFAOYSA-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
- 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
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 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
- 229960001575 emodepside Drugs 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
- 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
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 229960002418 ivermectin 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
- 229950003439 monepantel Drugs 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
- DYQFPHHPIWNYFO-UHFFFAOYSA-N n,4-bis(4-methylpyridin-2-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC(NC=2SC=C(N=2)C=2N=CC=C(C)C=2)=C1 DYQFPHHPIWNYFO-UHFFFAOYSA-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
- 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229960002957 praziquantel Drugs 0.000 claims 1
- 229960000996 pyrantel pamoate Drugs 0.000 claims 1
- 125000006085 pyrrolopyridyl group Chemical group 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
- 230000008685 targeting Effects 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 |
|---|---|---|---|
| US202063105013P | 2020-10-23 | 2020-10-23 | |
| US63/105,013 | 2020-10-23 | ||
| PCT/US2021/056127 WO2022087326A1 (en) | 2020-10-23 | 2021-10-22 | Heterocyclic compounds and their use for treatment of helminthic infections and diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2023547396A JP2023547396A (ja) | 2023-11-10 |
| JP2023547396A5 JP2023547396A5 (https=) | 2024-10-29 |
| JPWO2022087326A5 true JPWO2022087326A5 (https=) | 2024-10-29 |
Family
ID=78676658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023524715A Pending JP2023547396A (ja) | 2020-10-23 | 2021-10-22 | 蠕虫感染及び疾患の処置のための複素環式化合物及びその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20240025891A1 (https=) |
| EP (1) | EP4232449A1 (https=) |
| JP (1) | JP2023547396A (https=) |
| KR (1) | KR20230092972A (https=) |
| CN (1) | CN116547282A (https=) |
| WO (1) | WO2022087326A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA3219348A1 (en) | 2021-05-27 | 2022-12-01 | Anthony B. Pinkerton | Checkpoint kinase 1 (chk1) inhibitors and uses thereof |
| KR20250025634A (ko) * | 2022-05-24 | 2025-02-24 | 바운드리스 바이오, 인크. | 피리딘 관문 키나제 1(chk1) 억제제 및 그의 용도 |
| EP4626433A1 (en) * | 2022-11-29 | 2025-10-08 | Boundless Bio, Inc. | Checkpoint kinase 1 (chk1) inhibitors combinations and uses thereof |
| 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 (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20050227989A1 (en) * | 2004-04-13 | 2005-10-13 | Icagen, Inc. | Polycyclic thiazoles as potassium ion channel modulators |
| KR20140071472A (ko) * | 2011-10-04 | 2014-06-11 | 인스티튜트 포 헤퍼타이티스 앤드 바이러스 리서치 | 간세포 암종을 포함하는 암의 저해제로서 그리고 간염 바이러스 복제의 저해제로서의 치환된 아미노티아졸 |
| US9695193B2 (en) * | 2013-06-26 | 2017-07-04 | The Trustees Of Columbia University In The City Of New York | Inhibitors of Plasmodium falciparum equilibrative nucleoside transporter type I as anti-parasitic compounds |
| WO2016144678A1 (en) * | 2015-03-12 | 2016-09-15 | E I Du Pont De Nemours And Company | Heterocycle-substituted bicyclic azole pesticides |
| US10913734B2 (en) * | 2016-07-11 | 2021-02-09 | Baruch S. Blumberg Institute | Substituted aminothiazoles |
| US11505548B2 (en) * | 2019-04-26 | 2022-11-22 | Celgene Corporation | Heterocyclic compounds and their use for treatment of helminthic infections and diseases |
-
2021
- 2021-10-22 US US18/032,998 patent/US20240025891A1/en active Pending
- 2021-10-22 EP EP21810484.2A patent/EP4232449A1/en active Pending
- 2021-10-22 JP JP2023524715A patent/JP2023547396A/ja active Pending
- 2021-10-22 WO PCT/US2021/056127 patent/WO2022087326A1/en not_active Ceased
- 2021-10-22 CN CN202180071227.3A patent/CN116547282A/zh active Pending
- 2021-10-22 KR KR1020237016754A patent/KR20230092972A/ko active Pending
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