JP2010540569A5 - - Google Patents
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- JP2010540569A5 JP2010540569A5 JP2010527296A JP2010527296A JP2010540569A5 JP 2010540569 A5 JP2010540569 A5 JP 2010540569A5 JP 2010527296 A JP2010527296 A JP 2010527296A JP 2010527296 A JP2010527296 A JP 2010527296A JP 2010540569 A5 JP2010540569 A5 JP 2010540569A5
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- JP
- Japan
- Prior art keywords
- optionally substituted
- phenyl
- lower alkyl
- salt
- hydrogen
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 125000003107 substituted aryl group Chemical group 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 41
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 37
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 34
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 13
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000005647 linker group Chemical group 0.000 claims description 13
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims 46
- 150000003839 salts Chemical class 0.000 claims 45
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- -1 1,3,4 triazolyl Chemical group 0.000 claims 4
- 201000006417 multiple sclerosis Diseases 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims 2
- 230000005784 autoimmunity Effects 0.000 claims 2
- 208000037976 chronic inflammation Diseases 0.000 claims 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000009429 distress Effects 0.000 claims 2
- 230000001506 immunosuppresive effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 1
- HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 claims 1
- GSPMMBYLSBPDPD-UHFFFAOYSA-N 1-[2-[2-(cyclopentylamino)ethoxy]-3-[3-(4-fluorophenyl)butoxy]-4-methoxy-5,6-dimethylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(C)C(C)=C(C(C)=O)C=1OCCNC1CCCC1 GSPMMBYLSBPDPD-UHFFFAOYSA-N 0.000 claims 1
- RQHPSRVBUFJHPD-UHFFFAOYSA-N 1-[2-[2-acetyl-4-chloro-5-methoxy-3-methyl-6-(3-phenylpropoxy)phenoxy]ethyl]azetidin-3-one Chemical compound C=1C=CC=CC=1CCCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CC(=O)C1 RQHPSRVBUFJHPD-UHFFFAOYSA-N 0.000 claims 1
- CGRRNHLPSQSHLB-UHFFFAOYSA-N 1-[2-[2-acetyl-4-chloro-6-[3-(4-fluorophenyl)butoxy]-5-methoxy-3-methylphenoxy]ethyl]piperidin-4-one Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCC(=O)CC1 CGRRNHLPSQSHLB-UHFFFAOYSA-N 0.000 claims 1
- JQRJTRBEMHMVHZ-UHFFFAOYSA-N 1-[3-chloro-4-methoxy-2-methyl-5-(3-phenylpropoxy)-6-(2-thiomorpholin-4-ylethoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCSCC1 JQRJTRBEMHMVHZ-UHFFFAOYSA-N 0.000 claims 1
- XRLDXFLSAONSJB-UHFFFAOYSA-N 1-[3-chloro-4-methoxy-2-methyl-5-(4-phenylbutyl)-6-(2-pyridin-2-ylethoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCCCC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCC1=CC=CC=N1 XRLDXFLSAONSJB-UHFFFAOYSA-N 0.000 claims 1
- AFXQWYJUTLZZCT-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2-methyl-6-(2-morpholin-4-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCOCC1 AFXQWYJUTLZZCT-UHFFFAOYSA-N 0.000 claims 1
- MPKHVTUVOYVYHX-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2-methyl-6-(2-piperidin-1-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCCCC1 MPKHVTUVOYVYHX-UHFFFAOYSA-N 0.000 claims 1
- SDZCAOTUJXNNED-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2-methyl-6-(2-pyrazin-2-yloxyethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCOC1=CN=CC=N1 SDZCAOTUJXNNED-UHFFFAOYSA-N 0.000 claims 1
- LMABIUNSRMPZEJ-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2-methyl-6-(2-pyridin-2-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCC1=CC=CC=N1 LMABIUNSRMPZEJ-UHFFFAOYSA-N 0.000 claims 1
- RHHDNRDBTLFLTK-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2-methyl-6-(3-morpholin-4-ylpropoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCCN1CCOCC1 RHHDNRDBTLFLTK-UHFFFAOYSA-N 0.000 claims 1
- KOMPETZPHDRUMU-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2-methyl-6-(pyridin-2-ylmethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCC1=CC=CC=N1 KOMPETZPHDRUMU-UHFFFAOYSA-N 0.000 claims 1
- PGUGAUHBYMMBMG-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2-methyl-6-[2-(1,2,4-triazol-1-yl)ethoxy]phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1C=NC=N1 PGUGAUHBYMMBMG-UHFFFAOYSA-N 0.000 claims 1
- OWKPEMVKNFBFNL-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2-methyl-6-[3-(1-oxo-1,4-thiazinan-4-yl)propoxy]phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCCN1CCS(=O)CC1 OWKPEMVKNFBFNL-UHFFFAOYSA-N 0.000 claims 1
- JVYQJZLNAIRPMD-UHFFFAOYSA-N 1-[3-chloro-5-[3-(4-fluorophenyl)propoxy]-4-methoxy-2-methyl-6-(2-morpholin-4-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1CCCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCOCC1 JVYQJZLNAIRPMD-UHFFFAOYSA-N 0.000 claims 1
- KXTCDYKQXOIIER-UHFFFAOYSA-N 1-[3-chloro-5-[4-(4-fluorophenyl)pentyl]-4-methoxy-2-methyl-6-(2-morpholin-4-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCCC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCOCC1 KXTCDYKQXOIIER-UHFFFAOYSA-N 0.000 claims 1
- FOXXBOZZEZOPJH-UHFFFAOYSA-N 1-[3-chloro-5-[4-(4-fluorophenyl)pentyl]-4-methoxy-2-methyl-6-(2-pyridin-2-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCCC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCC1=CC=CC=N1 FOXXBOZZEZOPJH-UHFFFAOYSA-N 0.000 claims 1
- XVIBLMUDQBTZKO-UHFFFAOYSA-N 1-[4-methoxy-6-methyl-2-(2-morpholin-4-ylethoxy)-3-(3-phenylpropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCCOC=1C(OC)=CC(C)=C(C(C)=O)C=1OCCN1CCOCC1 XVIBLMUDQBTZKO-UHFFFAOYSA-N 0.000 claims 1
- ACEMEYWSGDXKJA-UHFFFAOYSA-N 1-[5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2,3-dimethyl-6-(2-morpholin-4-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(C)C(C)=C(C(C)=O)C=1OCCN1CCOCC1 ACEMEYWSGDXKJA-UHFFFAOYSA-N 0.000 claims 1
- CILRSKCBTLHOIZ-UHFFFAOYSA-N 1-[5-[3-(4-fluorophenyl)butoxy]-4-methoxy-2,3-dimethyl-6-(2-pyridin-2-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(C)C(C)=C(C(C)=O)C=1OCCC1=CC=CC=N1 CILRSKCBTLHOIZ-UHFFFAOYSA-N 0.000 claims 1
- PMJWSQWEHYPHNW-UHFFFAOYSA-N 1-[5-[3-(4-fluorophenyl)propoxy]-4-methoxy-2,3-dimethyl-6-(2-morpholin-4-ylethoxy)phenyl]ethanone Chemical compound C=1C=C(F)C=CC=1CCCOC=1C(OC)=C(C)C(C)=C(C(C)=O)C=1OCCN1CCOCC1 PMJWSQWEHYPHNW-UHFFFAOYSA-N 0.000 claims 1
- PHHHJHHNFPOTRT-UHFFFAOYSA-N 1-[5-chloro-2-[2-(3,3-difluoroazetidin-1-yl)ethoxy]-3-[3-(4-fluorophenyl)butoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CC(F)(F)C1 PHHHJHHNFPOTRT-UHFFFAOYSA-N 0.000 claims 1
- TUEIEJCESFKYPU-UHFFFAOYSA-N 1-[5-chloro-2-[2-(3,3-difluoroazetidin-1-yl)ethoxy]-4-methoxy-6-methyl-3-(3-phenylpropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CC(F)(F)C1 TUEIEJCESFKYPU-UHFFFAOYSA-N 0.000 claims 1
- KBCOVKKZKQHXKQ-UHFFFAOYSA-N 1-[5-chloro-2-[2-(3,3-difluoropiperidin-1-yl)ethoxy]-3-[3-(4-fluorophenyl)butoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCCC(F)(F)C1 KBCOVKKZKQHXKQ-UHFFFAOYSA-N 0.000 claims 1
- BHGUSJZLADDXGG-UHFFFAOYSA-N 1-[5-chloro-2-[2-(3,3-difluoropyrrolidin-1-yl)ethoxy]-4-methoxy-6-methyl-3-(3-phenylpropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCC(F)(F)C1 BHGUSJZLADDXGG-UHFFFAOYSA-N 0.000 claims 1
- YJOSRRCHKXMTAA-UHFFFAOYSA-N 1-[5-chloro-2-[2-(3-hydroxyazetidin-1-yl)ethoxy]-4-methoxy-6-methyl-3-(3-phenylpropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CC(O)C1 YJOSRRCHKXMTAA-UHFFFAOYSA-N 0.000 claims 1
- YCYCGOUZGYWODG-UHFFFAOYSA-N 1-[5-chloro-2-[2-(4,4-difluoropiperidin-1-yl)ethoxy]-3-[3-(4-fluorophenyl)butoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCC(F)(F)CC1 YCYCGOUZGYWODG-UHFFFAOYSA-N 0.000 claims 1
- JLISGBOIDPFSRD-UHFFFAOYSA-N 1-[5-chloro-2-[2-(cyclopentylamino)ethoxy]-3-[3-(4-fluorophenyl)butoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCNC1CCCC1 JLISGBOIDPFSRD-UHFFFAOYSA-N 0.000 claims 1
- SJMHDSOPXSARFU-UHFFFAOYSA-N 1-[5-chloro-2-[2-(cyclopentylamino)ethoxy]-4-methoxy-6-methyl-3-(3-phenylpropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCNC1CCCC1 SJMHDSOPXSARFU-UHFFFAOYSA-N 0.000 claims 1
- MBLFTTRVTPTPIA-UHFFFAOYSA-N 1-[5-chloro-2-[2-(dimethylamino)ethoxy]-3-[3-(4-fluorophenyl)butoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound COC1=C(Cl)C(C)=C(C(C)=O)C(OCCN(C)C)=C1OCCC(C)C1=CC=C(F)C=C1 MBLFTTRVTPTPIA-UHFFFAOYSA-N 0.000 claims 1
- VEAPPFBWEHILQO-UHFFFAOYSA-N 1-[5-chloro-2-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propoxy]-3-[3-(4-fluorophenyl)butoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCCN1CCS(=O)(=O)CC1 VEAPPFBWEHILQO-UHFFFAOYSA-N 0.000 claims 1
- AKEYKAZDWGUJMH-UHFFFAOYSA-N 1-[5-chloro-3-[3-(4-fluorophenyl)butoxy]-2-(2-imidazol-1-ylethoxy)-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1C=CN=C1 AKEYKAZDWGUJMH-UHFFFAOYSA-N 0.000 claims 1
- RIARVNMNNHWZTI-UHFFFAOYSA-N 1-[5-chloro-3-[3-(4-fluorophenyl)butoxy]-2-[2-(4-fluoropiperidin-1-yl)ethoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCC(F)CC1 RIARVNMNNHWZTI-UHFFFAOYSA-N 0.000 claims 1
- IRIXQIIFKKDDTC-UHFFFAOYSA-N 1-[5-chloro-3-[3-(4-fluorophenyl)butoxy]-2-[2-(4-hydroxypiperidin-1-yl)ethoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CCC(O)CC1 IRIXQIIFKKDDTC-UHFFFAOYSA-N 0.000 claims 1
- APEZGFTUXCOSNT-CAWMZFRYSA-N 1-[5-chloro-3-[3-(4-fluorophenyl)butoxy]-2-[2-[(3r)-3-fluoropyrrolidin-1-yl]ethoxy]-4-methoxy-6-methylphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1C(C)CCOC=1C(OC)=C(Cl)C(C)=C(C(C)=O)C=1OCCN1CC[C@@H](F)C1 APEZGFTUXCOSNT-CAWMZFRYSA-N 0.000 claims 1
- 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 claims 1
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 108010072051 Glatiramer Acetate Proteins 0.000 claims 1
- 108010005716 Interferon beta-1a Proteins 0.000 claims 1
- 108010005714 Interferon beta-1b Proteins 0.000 claims 1
- 102000004257 Potassium Channel Human genes 0.000 claims 1
- FHEAIOHRHQGZPC-KIWGSFCNSA-N acetic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.C[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 FHEAIOHRHQGZPC-KIWGSFCNSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000003838 furazanyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229960003776 glatiramer acetate Drugs 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 229960004461 interferon beta-1a Drugs 0.000 claims 1
- 229960003161 interferon beta-1b Drugs 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 1
- 229960001156 mitoxantrone Drugs 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 229960005027 natalizumab Drugs 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 108020001213 potassium channel Proteins 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97753807P | 2007-10-04 | 2007-10-04 | |
| PCT/AU2008/001480 WO2009043117A1 (en) | 2007-10-04 | 2008-10-03 | Novel aryl potassium channel blockers and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010540569A JP2010540569A (ja) | 2010-12-24 |
| JP2010540569A5 true JP2010540569A5 (https=) | 2011-10-27 |
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| US (1) | US8202513B2 (https=) |
| EP (1) | EP2197832A4 (https=) |
| JP (1) | JP2010540569A (https=) |
| KR (1) | KR20100087148A (https=) |
| CN (1) | CN101888989A (https=) |
| AU (1) | AU2008307075B2 (https=) |
| BR (1) | BRPI0817520A2 (https=) |
| CA (1) | CA2701579A1 (https=) |
| EA (1) | EA201070420A1 (https=) |
| IL (1) | IL204857A0 (https=) |
| MX (1) | MX2010003541A (https=) |
| NZ (1) | NZ584480A (https=) |
| WO (1) | WO2009043117A1 (https=) |
| ZA (1) | ZA201002385B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US9493451B2 (en) | 2011-05-16 | 2016-11-15 | Bionomics Limited | Amine derivatives as potassium channel blockers |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9556132B2 (en) * | 2012-06-25 | 2017-01-31 | Saniona A/S | Tetrazole derivatives and their use as potassium channel modulators |
| US10118890B2 (en) | 2014-10-10 | 2018-11-06 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| TWI698438B (zh) | 2015-03-13 | 2020-07-11 | 德商４Ｓｃ製藥公司 | Ｋv１.３抑制劑及其醫學應用 |
| TWI701249B (zh) | 2015-03-13 | 2020-08-11 | 德商４Ｓｃ製藥公司 | Ｋv１.３抑制劑及其醫學應用 |
| CA3157026A1 (en) * | 2019-10-07 | 2021-04-15 | D.E. Shaw Research, Llc | Arylmethylene aromatic compounds as kv1.3 potassium shaker channel blockers |
| MX2022004127A (es) * | 2019-10-07 | 2022-06-14 | De Shaw Res Llc | Compuestos heterociclicos de arilo como bloqueadores del canal de potasio tipo shaker kv1.3. |
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| BE635011A (https=) * | 1962-07-17 | |||
| JPS5195033A (ja) | 1975-02-13 | 1976-08-20 | Shinkinaasetofuenonjudotainoseizohoho | |
| US5017572A (en) | 1988-04-22 | 1991-05-21 | Delalande S.A. | Derivatives of 1-[3-(4-hydroxyphenyl) 1-hydroxy 1-propyl] benzene substituted in position 2 by an aminoalkyleneoxy chain, the method of preparing same and the application thereof to therapeutics |
| US5126351A (en) * | 1991-01-24 | 1992-06-30 | Glaxo Inc. | Antitumor compounds |
| US5494895A (en) * | 1993-07-22 | 1996-02-27 | Merck & Co., Inc. | Scorpion peptide margatoxin with immunosuppressant activity |
| JPH11511481A (ja) | 1995-10-31 | 1999-10-05 | メルク エンド カンパニー インコーポレーテッド | 免疫抑制活性を有するトリテルペン誘導体 |
| WO1997016438A1 (en) | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Triterpene derivatives with immunosuppressant activity |
| WO1998023639A2 (en) * | 1996-11-27 | 1998-06-04 | University Of Florida | ShK TOXIN COMPOSITIONS AND METHODS OF USE |
| JPH10316853A (ja) | 1997-05-15 | 1998-12-02 | Sumitomo Bakelite Co Ltd | 半導体多層配線用層間絶縁膜樹脂組成物及び該絶縁膜の製造方法 |
| JPH10316617A (ja) | 1997-05-16 | 1998-12-02 | Nippon Kayaku Co Ltd | 新規なフタル酸誘導体 |
| US20030065039A1 (en) * | 1997-06-26 | 2003-04-03 | Statens Serum Institute | Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones |
| US6051590A (en) * | 1999-05-13 | 2000-04-18 | Merck & Co., Inc. | Immunosuppressant tricyclic compounds |
| AU2003224672B2 (en) * | 2002-03-08 | 2010-02-04 | Eisai R&D Management Co., Ltd. | Macrocyclic compounds useful as pharmaceuticals |
| US7915306B2 (en) * | 2002-03-08 | 2011-03-29 | Eisai Co., Ltd. | Macrocyclic compounds useful as pharmaceuticals |
| AUPS110302A0 (en) | 2002-03-14 | 2002-04-18 | Biomolecular Research Institute Limited | Novel chalcone derivatives and uses thereof |
| AUPS127202A0 (en) * | 2002-03-20 | 2002-04-18 | Walter And Eliza Hall Institute Of Medical Research, The | Therapeutic ion channel blocking agents and methods of use thereof |
| US7557138B2 (en) * | 2004-10-04 | 2009-07-07 | The Regents Of The University Of California | 5-phenoxyalkoxypsoralens and methods for selective inhibition of the voltage gated Kv1.3 potassium channel |
| US8063093B2 (en) * | 2005-03-15 | 2011-11-22 | Andrew J Harvey | Potassium channel blockers and uses thereof |
| NZ575685A (en) | 2006-10-04 | 2012-04-27 | Bionomics Ltd | Novel benzofuran potassium channel blockers and uses thereof |
-
2008
- 2008-10-03 JP JP2010527296A patent/JP2010540569A/ja active Pending
- 2008-10-03 BR BRPI0817520-9A patent/BRPI0817520A2/pt not_active IP Right Cessation
- 2008-10-03 MX MX2010003541A patent/MX2010003541A/es not_active Application Discontinuation
- 2008-10-03 WO PCT/AU2008/001480 patent/WO2009043117A1/en not_active Ceased
- 2008-10-03 AU AU2008307075A patent/AU2008307075B2/en not_active Ceased
- 2008-10-03 EA EA201070420A patent/EA201070420A1/ru unknown
- 2008-10-03 CA CA2701579A patent/CA2701579A1/en not_active Abandoned
- 2008-10-03 US US12/681,763 patent/US8202513B2/en not_active Expired - Fee Related
- 2008-10-03 CN CN2008801192463A patent/CN101888989A/zh active Pending
- 2008-10-03 NZ NZ584480A patent/NZ584480A/en not_active IP Right Cessation
- 2008-10-03 EP EP08800115.1A patent/EP2197832A4/en not_active Withdrawn
- 2008-10-03 KR KR1020107009781A patent/KR20100087148A/ko not_active Withdrawn
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