JP2019528291A5 - - Google Patents
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- JP2019528291A5 JP2019528291A5 JP2019510688A JP2019510688A JP2019528291A5 JP 2019528291 A5 JP2019528291 A5 JP 2019528291A5 JP 2019510688 A JP2019510688 A JP 2019510688A JP 2019510688 A JP2019510688 A JP 2019510688A JP 2019528291 A5 JP2019528291 A5 JP 2019528291A5
- Authority
- JP
- Japan
- Prior art keywords
- oxazole
- benzo
- oxadiazole
- amine
- alkyl
- 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.)
- Withdrawn
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- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000004122 cyclic group Chemical group 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 28
- 208000035143 Bacterial infection Diseases 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 241000894006 Bacteria Species 0.000 claims description 17
- -1 cyano, hydroxyl Chemical group 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 241000194032 Enterococcus faecalis Species 0.000 claims description 7
- 241000194017 Streptococcus Species 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 241000588653 Neisseria Species 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 241000588652 Neisseria gonorrhoeae Species 0.000 claims description 5
- 241001505901 Streptococcus sp. 'group A' Species 0.000 claims description 5
- 241000589884 Treponema pallidum Species 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 241000186046 Actinomyces Species 0.000 claims description 4
- 241000606125 Bacteroides Species 0.000 claims description 4
- 241000193163 Clostridioides difficile Species 0.000 claims description 4
- 241000193468 Clostridium perfringens Species 0.000 claims description 4
- 241000186216 Corynebacterium Species 0.000 claims description 4
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 4
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 4
- 241000191967 Staphylococcus aureus Species 0.000 claims description 4
- 241000193985 Streptococcus agalactiae Species 0.000 claims description 4
- 241000194049 Streptococcus equinus Species 0.000 claims description 4
- 241000193998 Streptococcus pneumoniae Species 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 229940032049 enterococcus faecalis Drugs 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 241000122230 Acinetobacter junii Species 0.000 claims description 3
- 241000186041 Actinomyces israelii Species 0.000 claims description 3
- 241000589876 Campylobacter Species 0.000 claims description 3
- 241000193449 Clostridium tetani Species 0.000 claims description 3
- 241000186227 Corynebacterium diphtheriae Species 0.000 claims description 3
- 241000194033 Enterococcus Species 0.000 claims description 3
- 241000194031 Enterococcus faecium Species 0.000 claims description 3
- 241000605986 Fusobacterium nucleatum Species 0.000 claims description 3
- 241000606768 Haemophilus influenzae Species 0.000 claims description 3
- 241000590002 Helicobacter pylori Species 0.000 claims description 3
- 241000589248 Legionella Species 0.000 claims description 3
- 208000007764 Legionnaires' Disease Diseases 0.000 claims description 3
- 241000589902 Leptospira Species 0.000 claims description 3
- 241000186779 Listeria monocytogenes Species 0.000 claims description 3
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 3
- 241000186362 Mycobacterium leprae Species 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 241000588650 Neisseria meningitidis Species 0.000 claims description 3
- 241000606856 Pasteurella multocida Species 0.000 claims description 3
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 3
- 241000193996 Streptococcus pyogenes Species 0.000 claims description 3
- 241000193990 Streptococcus sp. 'group B' Species 0.000 claims description 3
- 241001312524 Streptococcus viridans Species 0.000 claims description 3
- 241000589904 Treponema pallidum subsp. pertenue Species 0.000 claims description 3
- 241000193462 [Clostridium] innocuum Species 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229940047650 haemophilus influenzae Drugs 0.000 claims description 3
- 229940037467 helicobacter pylori Drugs 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229940051027 pasteurella multocida Drugs 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 201000008827 tuberculosis Diseases 0.000 claims description 3
- FRNTUFQKHQMLSE-UHFFFAOYSA-N 1,3-benzoxazole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=COC2=C1 FRNTUFQKHQMLSE-UHFFFAOYSA-N 0.000 claims description 2
- PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 claims description 2
- RAIDETWAVHBZPK-UHFFFAOYSA-N 1-[2-(1,3,4-oxadiazol-2-ylamino)-1,3-benzoxazol-6-yl]pyrrolidin-2-one Chemical compound O1C(=NN=C1)NC=1OC2=C(N=1)C=CC(=C2)N1C(CCC1)=O RAIDETWAVHBZPK-UHFFFAOYSA-N 0.000 claims description 2
- HIJXDBIWKKEDAY-UHFFFAOYSA-N 2-(1,3,4-oxadiazol-2-yl)-3H-1,3-benzoxazole-2,6-diamine Chemical compound O1C(=NN=C1)C1(OC2=C(N1)C=CC(=C2)N)N HIJXDBIWKKEDAY-UHFFFAOYSA-N 0.000 claims description 2
- ZHRXZPHSEOBDCW-UHFFFAOYSA-N 2-(1,3,4-oxadiazol-2-ylamino)-1,3-benzoxazol-6-ol Chemical compound O1C(=NN=C1)NC=1OC2=C(N=1)C=CC(=C2)O ZHRXZPHSEOBDCW-UHFFFAOYSA-N 0.000 claims description 2
- VUAYRVYSQOPQOQ-UHFFFAOYSA-N 2-(1,3,4-oxadiazol-2-ylamino)-1,3-benzoxazole-6-carboxylic acid Chemical compound O1C(=NN=C1)NC=1OC2=C(N=1)C=CC(=C2)C(=O)O VUAYRVYSQOPQOQ-UHFFFAOYSA-N 0.000 claims description 2
- FPEGACXSUIACHC-UHFFFAOYSA-N 3h-oxadiazole-2-carboxylic acid Chemical compound OC(=O)N1NC=CO1 FPEGACXSUIACHC-UHFFFAOYSA-N 0.000 claims description 2
- NIUFVDQQKBARIY-UHFFFAOYSA-N 4-[(6-chloro-1,3-benzoxazol-2-yl)amino]-1,3-oxazole-2-carboxylic acid Chemical compound ClC1=CC2=C(N=C(O2)NC=2N=C(OC=2)C(=O)O)C=C1 NIUFVDQQKBARIY-UHFFFAOYSA-N 0.000 claims description 2
- NVAFYAACHPNJIF-UHFFFAOYSA-N 5-[(5-fluoro-1,3-benzoxazol-2-yl)amino]-1,3,4-oxadiazole-2-carbonitrile Chemical compound FC=1C=CC2=C(N=C(O2)NC2=NN=C(O2)C#N)C=1 NVAFYAACHPNJIF-UHFFFAOYSA-N 0.000 claims description 2
- UXXVLXFFAPWJQO-UHFFFAOYSA-N 5-[(5-fluoro-1,3-benzoxazol-2-yl)amino]-1,3,4-oxadiazole-2-carboxamide Chemical compound FC=1C=CC2=C(N=C(O2)NC2=NN=C(O2)C(=O)N)C=1 UXXVLXFFAPWJQO-UHFFFAOYSA-N 0.000 claims description 2
- BSSGPOJRXJVSBI-UHFFFAOYSA-N 5-[(6-chloro-1,3-benzoxazol-2-yl)amino]-1,3,4-oxadiazole-2-carbonitrile Chemical compound ClC1=CC2=C(N=C(O2)NC2=NN=C(O2)C#N)C=C1 BSSGPOJRXJVSBI-UHFFFAOYSA-N 0.000 claims description 2
- MGPPRGSIHDVBBK-UHFFFAOYSA-N 5-[(6-chloro-1,3-benzoxazol-2-yl)amino]-1,3,4-oxadiazole-2-carboxamide Chemical compound ClC1=CC2=C(N=C(O2)NC2=NN=C(O2)C(=O)N)C=C1 MGPPRGSIHDVBBK-UHFFFAOYSA-N 0.000 claims description 2
- WSSDTWAPGLKDCQ-UHFFFAOYSA-N 5-[(6-fluoro-1,3-benzoxazol-2-yl)amino]-1,3,4-oxadiazole-2-carboxamide Chemical compound FC1=CC2=C(N=C(O2)NC2=NN=C(O2)C(=O)N)C=C1 WSSDTWAPGLKDCQ-UHFFFAOYSA-N 0.000 claims description 2
- AZMGETFUDRUHCX-UHFFFAOYSA-N 5-chloro-6-methoxy-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC=1C(=CC2=C(N=C(O2)NC=2OC=NN=2)C=1)OC AZMGETFUDRUHCX-UHFFFAOYSA-N 0.000 claims description 2
- BBZSIWQJQGZBSA-UHFFFAOYSA-N 5-chloro-6-methyl-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC=1C(=CC2=C(N=C(O2)NC=2OC=NN=2)C=1)C BBZSIWQJQGZBSA-UHFFFAOYSA-N 0.000 claims description 2
- SYRSOQLBQJAHGZ-UHFFFAOYSA-N 5-chloro-N-(1,3,4-oxadiazol-2-yl)-6-(trifluoromethoxy)-1,3-benzoxazol-2-amine Chemical compound ClC=1C(=CC2=C(N=C(O2)NC=2OC=NN=2)C=1)OC(F)(F)F SYRSOQLBQJAHGZ-UHFFFAOYSA-N 0.000 claims description 2
- UVMFTQOFGZTLLF-UHFFFAOYSA-N 5-chloro-N-(1,3-thiazol-4-yl)-1,3-benzoxazol-2-amine Chemical compound ClC=1C=CC2=C(N=C(O2)NC=2N=CSC=2)C=1 UVMFTQOFGZTLLF-UHFFFAOYSA-N 0.000 claims description 2
- CYJUNIDNMCKMEI-UHFFFAOYSA-N 5-fluoro-6-methoxy-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound FC=1C(=CC2=C(N=C(O2)NC=2OC=NN=2)C=1)OC CYJUNIDNMCKMEI-UHFFFAOYSA-N 0.000 claims description 2
- SBILZBCLSVWOTH-UHFFFAOYSA-N 5-fluoro-6-methyl-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound FC=1C(=CC2=C(N=C(O2)NC=2OC=NN=2)C=1)C SBILZBCLSVWOTH-UHFFFAOYSA-N 0.000 claims description 2
- NZSZXMBTYGMBEV-UHFFFAOYSA-N 5-fluoro-N-(1,3,4-oxadiazol-2-yl)-6-(trifluoromethoxy)-1,3-benzoxazol-2-amine Chemical compound FC=1C(=CC2=C(N=C(O2)NC=2OC=NN=2)C=1)OC(F)(F)F NZSZXMBTYGMBEV-UHFFFAOYSA-N 0.000 claims description 2
- UZNJREMMYCBNHT-UHFFFAOYSA-N 5-methyl-N-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]-1,3,4-thiadiazol-2-amine Chemical compound CC1=NN=C(S1)NC1=NC2=C(N1)C=CC(=C2)C(F)(F)F UZNJREMMYCBNHT-UHFFFAOYSA-N 0.000 claims description 2
- ZOEARHYZLYQFNW-UHFFFAOYSA-N 6-(2-methoxyethoxy)-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound COCCOC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1 ZOEARHYZLYQFNW-UHFFFAOYSA-N 0.000 claims description 2
- GZSPPESWVWTQNX-UHFFFAOYSA-N 6-bromo-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound BrC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1 GZSPPESWVWTQNX-UHFFFAOYSA-N 0.000 claims description 2
- ICRQUQUHPZRAFR-UHFFFAOYSA-N 6-chloro-4-fluoro-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC=NN=2)C(=C1)F ICRQUQUHPZRAFR-UHFFFAOYSA-N 0.000 claims description 2
- APTIOJOQJKSQIL-UHFFFAOYSA-N 6-chloro-4-methyl-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC=NN=2)C(=C1)C APTIOJOQJKSQIL-UHFFFAOYSA-N 0.000 claims description 2
- FRZLFCVAZSOOJH-UHFFFAOYSA-N 6-chloro-5-methoxy-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1OC FRZLFCVAZSOOJH-UHFFFAOYSA-N 0.000 claims description 2
- GFJZRLUYMXDHSV-UHFFFAOYSA-N 6-chloro-5-methyl-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1C GFJZRLUYMXDHSV-UHFFFAOYSA-N 0.000 claims description 2
- SWWZJVJEKIFQND-UHFFFAOYSA-N 6-chloro-N-(1,2-oxazol-4-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2C=NOC=2)C=C1 SWWZJVJEKIFQND-UHFFFAOYSA-N 0.000 claims description 2
- GHKJBJUTXROIFY-UHFFFAOYSA-N 6-chloro-N-(1,2-thiazol-3-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC2=NSC=C2)C=C1 GHKJBJUTXROIFY-UHFFFAOYSA-N 0.000 claims description 2
- TXPAXUWKOQXHGO-UHFFFAOYSA-N 6-chloro-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1 TXPAXUWKOQXHGO-UHFFFAOYSA-N 0.000 claims description 2
- MPVYLFKKLSJBAI-UHFFFAOYSA-N 6-chloro-N-(1,3,4-oxadiazol-2-yl)-5-(trifluoromethoxy)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1OC(F)(F)F MPVYLFKKLSJBAI-UHFFFAOYSA-N 0.000 claims description 2
- UOIAYRCVJSHALK-UHFFFAOYSA-N 6-chloro-N-(1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1C(F)(F)F UOIAYRCVJSHALK-UHFFFAOYSA-N 0.000 claims description 2
- BMJJHTNLIQKIJT-UHFFFAOYSA-N 6-chloro-N-(1,3,4-oxadiazol-2-yl)-[1,3]oxazolo[4,5-b]pyridin-2-amine Chemical compound ClC=1C=C2C(=NC=1)N=C(O2)NC=1OC=NN=1 BMJJHTNLIQKIJT-UHFFFAOYSA-N 0.000 claims description 2
- IWPQADCWQUWAEA-UHFFFAOYSA-N 6-chloro-N-(1,3-oxazol-4-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2N=COC=2)C=C1 IWPQADCWQUWAEA-UHFFFAOYSA-N 0.000 claims description 2
- QJTBXESERCOJPW-UHFFFAOYSA-N 6-chloro-N-(1H-1,2,4-triazol-5-yl)-5-(trifluoromethyl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC2=NN=CN2)C=C1C(F)(F)F QJTBXESERCOJPW-UHFFFAOYSA-N 0.000 claims description 2
- GOLYBCJZAOQKKJ-UHFFFAOYSA-N 6-chloro-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC(=NN=2)C2CC2)C=C1 GOLYBCJZAOQKKJ-UHFFFAOYSA-N 0.000 claims description 2
- KOUPDEUQDRFBBH-UHFFFAOYSA-N 6-chloro-N-(5-ethynyl-1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC(=NN=2)C#C)C=C1 KOUPDEUQDRFBBH-UHFFFAOYSA-N 0.000 claims description 2
- WEAJXWVRFSSZOJ-UHFFFAOYSA-N 6-chloro-N-(5-methyl-1,2-oxazol-3-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC2=NOC(=C2)C)C=C1 WEAJXWVRFSSZOJ-UHFFFAOYSA-N 0.000 claims description 2
- WRJYZFMFUKNYLQ-UHFFFAOYSA-N 6-chloro-N-(5-propan-2-yl-1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC(=NN=2)C(C)C)C=C1 WRJYZFMFUKNYLQ-UHFFFAOYSA-N 0.000 claims description 2
- WBBNJVBDLWVWBD-UHFFFAOYSA-N 6-chloro-N-[4-(2-methoxyethyl)-5-methyl-1,2,4-triazol-3-yl]-5-(trifluoromethyl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC2=NN=C(N2CCOC)C)C=C1C(F)(F)F WBBNJVBDLWVWBD-UHFFFAOYSA-N 0.000 claims description 2
- KIAXADQJYUQDKO-UHFFFAOYSA-N 6-chloro-N-[5-(oxolan-2-yl)-1,3,4-oxadiazol-2-yl]-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC(=NN=2)C2OCCC2)C=C1 KIAXADQJYUQDKO-UHFFFAOYSA-N 0.000 claims description 2
- JWOFTIIBCMOCHV-UHFFFAOYSA-N 6-chloro-N-[5-(oxolan-3-yl)-1,3,4-oxadiazol-2-yl]-1,3-benzoxazol-2-amine Chemical compound ClC1=CC2=C(N=C(O2)NC=2OC(=NN=2)C2COCC2)C=C1 JWOFTIIBCMOCHV-UHFFFAOYSA-N 0.000 claims description 2
- QDXJVLXSWHRNIC-UHFFFAOYSA-N 6-cyclopropyl-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound C1(CC1)C1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1 QDXJVLXSWHRNIC-UHFFFAOYSA-N 0.000 claims description 2
- XPIRTRAOZKDMPX-UHFFFAOYSA-N 6-fluoro-5-methoxy-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound FC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1OC XPIRTRAOZKDMPX-UHFFFAOYSA-N 0.000 claims description 2
- ZJLBDPLSLDQYLJ-UHFFFAOYSA-N 6-fluoro-5-methyl-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound FC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1C ZJLBDPLSLDQYLJ-UHFFFAOYSA-N 0.000 claims description 2
- SZVQTWSATDRJGI-UHFFFAOYSA-N 6-fluoro-N-(1,3,4-oxadiazol-2-yl)-1,3-benzoxazol-2-amine Chemical compound FC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1 SZVQTWSATDRJGI-UHFFFAOYSA-N 0.000 claims description 2
- UCJUHBIRSSFGBX-UHFFFAOYSA-N 6-fluoro-N-(1,3,4-oxadiazol-2-yl)-5-(trifluoromethoxy)-1,3-benzoxazol-2-amine Chemical compound FC1=CC2=C(N=C(O2)NC=2OC=NN=2)C=C1OC(F)(F)F UCJUHBIRSSFGBX-UHFFFAOYSA-N 0.000 claims description 2
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| EP3636645A1 (de) | 2018-10-11 | 2020-04-15 | Bayer Aktiengesellschaft | Verfahren zur herstellung schwefel-substituierter pyridinderivate |
| KR102793543B1 (ko) | 2018-10-11 | 2025-04-11 | 바이엘 악티엔게젤샤프트 | 이미다졸 유도체의 제조 방법 |
| TWI841671B (zh) | 2019-01-24 | 2024-05-11 | 日商第一三共股份有限公司 | 具有取代基之脲化合物 |
| AU2020225301A1 (en) | 2019-02-22 | 2021-08-26 | Anifera Limited | Compositions providing enhanced antibacterial activity against gram-positive bacteria and use thereof |
| CN111808093B (zh) * | 2019-04-12 | 2023-05-16 | 中国医学科学院医药生物技术研究所 | 一种新德里金属-β-内酰胺酶-1抑制剂 |
| IL287183B2 (en) | 2019-04-12 | 2025-01-01 | Mitobridge Inc | Inductors 1 HMOX |
| US12528798B2 (en) | 2019-10-29 | 2026-01-20 | Lg Chem, Ltd. | Compound for crop protectant |
| CN116528873B (zh) * | 2020-11-19 | 2025-08-22 | A&J科学有限公司 | 新型化合物、其制造方法及包含其的抗生素组合物 |
| CN113185475A (zh) * | 2021-04-29 | 2021-07-30 | 江苏永凯化学有限公司 | 一种高效低污染的精恶唑禾草灵生产工艺 |
| AU2022286464A1 (en) * | 2021-05-31 | 2024-01-18 | Asieris Pharmaceuticals (Shanghai) Co., Ltd. | 7-nitro-8-hydroxyquinoline derivative, preparation method therefor and medical use thereof |
| KR102754999B1 (ko) * | 2022-01-06 | 2025-01-21 | 충남대학교산학협력단 | 신규한 화합물 및 이를 포함하는 결핵균 또는 비결핵항산균 감염질환 치료용 약제학적 조성물 |
| JP2025522339A (ja) * | 2022-06-01 | 2025-07-15 | クダ セラピューティクス インコーポレイテッド | イミダゾピリジン及びオキサゾロピリジン誘導体及びその類似体、その調製方法、ＨＩＦ－１／２ａ経路阻害の方法、並びに、フェロトーシスの誘導 |
| WO2024130173A1 (en) * | 2022-12-16 | 2024-06-20 | Immvention Therapeutix | Benzimidazole derivatives |
| KR102840252B1 (ko) * | 2023-04-27 | 2025-07-30 | 한국화학연구원 | 시아노벤즈이미다졸 유도체, 약제학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약제학적 조성물 |
| CN117003710A (zh) * | 2023-07-19 | 2023-11-07 | 镇江先锋植保科技有限公司 | 一种2-巯基-6-氯苯并恶唑的制备方法 |
| AU2024331213A1 (en) * | 2023-09-01 | 2026-04-16 | Immvention Therapeutix, Inc. | Substituted benzoxazolylamino benzoxazoles |
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| US8604217B2 (en) * | 2009-11-12 | 2013-12-10 | Selvita S.A. | Compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent |
| JP5786402B2 (ja) * | 2011-03-29 | 2015-09-30 | コニカミノルタ株式会社 | 光学フィルム、及びそれを用いた偏光板、液晶表示装置 |
| WO2016039939A1 (en) * | 2014-09-09 | 2016-03-17 | Ptc Therapeutics, Inc. | Bicyclic and tricyclic substituted 2-pyridinone antibacterial compounds |
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2019
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