CA2949229A1 - Derives de benzene sulfonamide et leur utilisation comme modulateurs de rorc - Google Patents
Derives de benzene sulfonamide et leur utilisation comme modulateurs de rorc Download PDFInfo
- Publication number
- CA2949229A1 CA2949229A1 CA2949229A CA2949229A CA2949229A1 CA 2949229 A1 CA2949229 A1 CA 2949229A1 CA 2949229 A CA2949229 A CA 2949229A CA 2949229 A CA2949229 A CA 2949229A CA 2949229 A1 CA2949229 A1 CA 2949229A1
- Authority
- CA
- Canada
- Prior art keywords
- methylsulfonyl
- piperidin
- 6alkyl
- isobutyl
- oxy
- 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.)
- Abandoned
Links
- 229940124824 RORC modulator Drugs 0.000 title description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 238000000034 method Methods 0.000 claims abstract description 77
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 206010003246 arthritis Diseases 0.000 claims abstract description 10
- -1 N-(4-fluorophenyl)-N-isobutyl-6-((1-(methylsulfonyl)azetidin-3-yl)oxy)pyridine-sulfonamide Chemical compound 0.000 claims description 103
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 76
- 125000005843 halogen group Chemical group 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 claims description 32
- 125000004429 atom Chemical group 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 24
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000002837 carbocyclic group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- HGKUMNWJDULGOK-UHFFFAOYSA-N 1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-2,3-dihydroindole Chemical compound CS(=O)(=O)N1CCC(CC1)OC1=CC=C(C=C1)S(=O)(=O)N1CCC2=CC=CC=C12 HGKUMNWJDULGOK-UHFFFAOYSA-N 0.000 claims description 3
- FXZRFZMZPMIHCM-UHFFFAOYSA-N 2-methyl-1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-2,3-dihydroindole Chemical compound CC1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C FXZRFZMZPMIHCM-UHFFFAOYSA-N 0.000 claims description 3
- ZDZLYIANTIWBNN-UHFFFAOYSA-N 4-[4-[3-(4-chlorophenyl)pyrrolidin-1-yl]sulfonylphenoxy]-1-methylsulfonylpiperidine Chemical compound ClC1=CC=C(C=C1)C1CN(CC1)S(=O)(=O)C1=CC=C(OC2CCN(CC2)S(=O)(=O)C)C=C1 ZDZLYIANTIWBNN-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 24
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- LJVFCGKVAXNHDU-UHFFFAOYSA-N 2-methyl-1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-3,4-dihydro-2H-quinoline Chemical compound CC1CCC2=C(C=CC=C2)N1S(=O)(=O)C1=CC=C(OC2CCN(CC2)S(C)(=O)=O)C=C1 LJVFCGKVAXNHDU-UHFFFAOYSA-N 0.000 claims 2
- PNFCGWUMSRHLEI-OAQYLSRUSA-N N-(2-methylpropyl)-4-(4-methylsulfonylpiperazin-1-yl)-N-[(2S)-2-phenylpropyl]benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)N1CCN(CC1)S(=O)(=O)C)C[C@@H](C)C1=CC=CC=C1 PNFCGWUMSRHLEI-OAQYLSRUSA-N 0.000 claims 2
- MMTZBJKUTRKTJB-UHFFFAOYSA-N N-[2-(4-chlorophenyl)ethyl]-N-(2-methylpropyl)-4-(4-methylsulfonylpiperazin-1-yl)benzenesulfonamide Chemical compound ClC1=CC=C(C=C1)CCN(S(=O)(=O)C1=CC=C(C=C1)N1CCN(CC1)S(=O)(=O)C)CC(C)C MMTZBJKUTRKTJB-UHFFFAOYSA-N 0.000 claims 2
- IKIQKDFNKVLPJC-UHFFFAOYSA-N n-(4-fluorophenyl)-n-(2-methylpropyl)-6-(1-methylsulfonylpiperidin-4-yl)oxypyridine-3-sulfonamide Chemical compound C=1C=C(OC2CCN(CC2)S(C)(=O)=O)N=CC=1S(=O)(=O)N(CC(C)C)C1=CC=C(F)C=C1 IKIQKDFNKVLPJC-UHFFFAOYSA-N 0.000 claims 2
- RZEAZPGTSYPDOP-UHFFFAOYSA-N n-(4-fluorophenyl)-n-(2-methylpropyl)-6-[(1-methylsulfonylpiperidin-4-yl)amino]pyridine-3-sulfonamide Chemical compound C=1C=C(NC2CCN(CC2)S(C)(=O)=O)N=CC=1S(=O)(=O)N(CC(C)C)C1=CC=C(F)C=C1 RZEAZPGTSYPDOP-UHFFFAOYSA-N 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- JOVVLGPCSQCBBU-UHFFFAOYSA-N 1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-2,3,4,5-tetrahydro-1-benzazepine Chemical compound CS(=O)(=O)N1CCC(CC1)OC1=CC=C(C=C1)S(=O)(=O)N1C2=C(CCCC1)C=CC=C2 JOVVLGPCSQCBBU-UHFFFAOYSA-N 0.000 claims 1
- QTZUJNYPCIRQCZ-UHFFFAOYSA-N 1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-3,4-dihydro-2H-quinoline Chemical compound CS(=O)(=O)N1CCC(CC1)OC1=CC=C(C=C1)S(=O)(=O)N1CCCC2=C1C=CC=C2 QTZUJNYPCIRQCZ-UHFFFAOYSA-N 0.000 claims 1
- ZDFBHPSZFOEIOC-UHFFFAOYSA-N 1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-3,5-dihydro-2H-4,1-benzoxazepine Chemical compound CS(=O)(=O)N1CCC(CC1)OC1=CC=C(C=C1)S(=O)(=O)N1CCOCC2=C1C=CC=C2 ZDFBHPSZFOEIOC-UHFFFAOYSA-N 0.000 claims 1
- MOKROUGCQSXKPR-UHFFFAOYSA-N 1-[4-[(2-chlorophenyl)-(2-methylpropyl)sulfamoyl]phenyl]piperidine-4-carboxylic acid Chemical compound CC(C)CN(C1=C(Cl)C=CC=C1)S(=O)(=O)C1=CC=C(C=C1)N1CCC(CC1)C(O)=O MOKROUGCQSXKPR-UHFFFAOYSA-N 0.000 claims 1
- GQEPWCJKHBONAE-UHFFFAOYSA-N 11-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-11-azatricyclo[6.2.1.02,7]undeca-2,4,6-triene Chemical compound CS(=O)(=O)N1CCC(CC1)OC1=CC=C(C=C1)S(=O)(=O)N1C2CCC1C1=CC=CC=C21 GQEPWCJKHBONAE-UHFFFAOYSA-N 0.000 claims 1
- XYCLWIAFAUPNAE-UHFFFAOYSA-N 2-ethyl-N-(4-fluorophenyl)-N-methyl-4-(4-methylsulfonylpiperazin-1-yl)benzenesulfonamide Chemical compound C(C)C1=C(C=CC(=C1)N1CCN(CC1)S(=O)(=O)C)S(=O)(=O)N(C)C1=CC=C(C=C1)F XYCLWIAFAUPNAE-UHFFFAOYSA-N 0.000 claims 1
- AHNSFKQIQNCSLL-UHFFFAOYSA-N 2-fluoro-N-(2-methylpropyl)-4-(4-methylsulfonylpiperazin-1-yl)-N-(2-phenylethyl)benzenesulfonamide Chemical compound FC1=C(C=CC(=C1)N1CCN(CC1)S(=O)(=O)C)S(=O)(=O)N(CCC1=CC=CC=C1)CC(C)C AHNSFKQIQNCSLL-UHFFFAOYSA-N 0.000 claims 1
- NEMHNVNNMYKZAI-UHFFFAOYSA-N 3-benzyl-1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonylazepane Chemical compound C(C1=CC=CC=C1)C1CN(CCCC1)S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C NEMHNVNNMYKZAI-UHFFFAOYSA-N 0.000 claims 1
- ZCTFXAPEEKBHAC-UHFFFAOYSA-N 3-fluoro-N-(2-methylpropyl)-4-(4-methylsulfonylpiperazin-1-yl)-N-(2-phenylethyl)benzenesulfonamide Chemical compound FC=1C=C(C=CC1N1CCN(CC1)S(=O)(=O)C)S(=O)(=O)N(CCC1=CC=CC=C1)CC(C)C ZCTFXAPEEKBHAC-UHFFFAOYSA-N 0.000 claims 1
- QJPHKCIZBABCGO-UHFFFAOYSA-N 3-methyl-1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-2,3,4,5-tetrahydro-1-benzazepine Chemical compound CC1CCC2=C(N(C1)S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)C=CC=C2 QJPHKCIZBABCGO-UHFFFAOYSA-N 0.000 claims 1
- FEEDSYTZNJYBBU-UHFFFAOYSA-N 3-methyl-1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-3,4-dihydro-2H-quinoline Chemical compound CC1CN(C2=C(C1)C=CC=C2)S(=O)(=O)C1=CC=C(OC2CCN(CC2)S(C)(=O)=O)C=C1 FEEDSYTZNJYBBU-UHFFFAOYSA-N 0.000 claims 1
- PSBKKICRGWQAAH-UHFFFAOYSA-N 4-(4-acetylpiperazin-1-yl)-N-(5-fluoropyridin-2-yl)-N-(2-methylpropyl)benzenesulfonamide Chemical compound C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)S(=O)(=O)N(CC(C)C)C1=NC=C(C=C1)F PSBKKICRGWQAAH-UHFFFAOYSA-N 0.000 claims 1
- NBHNCBNDFSXYCZ-UHFFFAOYSA-N 4-(4-acetylpiperazin-1-yl)-N-[(4-fluorophenyl)methyl]-N-(2-methylpropyl)benzenesulfonamide Chemical compound C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)S(=O)(=O)N(CC(C)C)CC1=CC=C(C=C1)F NBHNCBNDFSXYCZ-UHFFFAOYSA-N 0.000 claims 1
- HYJQQPXRJUSXQE-UHFFFAOYSA-N 4-(4-acetylpiperazin-1-yl)-n-(2-methylpropyl)-n-[2-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound C=1C=C(N2CCN(CC2)C(C)=O)C=CC=1S(=O)(=O)N(CC(C)C)C1=CC=CC=C1C(F)(F)F HYJQQPXRJUSXQE-UHFFFAOYSA-N 0.000 claims 1
- PZYGNMWOOHESPU-UHFFFAOYSA-N 4-(4-acetylpiperazin-1-yl)-n-(2-methylpropyl)-n-[[2-(trifluoromethyl)phenyl]methyl]benzenesulfonamide Chemical compound C=1C=C(N2CCN(CC2)C(C)=O)C=CC=1S(=O)(=O)N(CC(C)C)CC1=CC=CC=C1C(F)(F)F PZYGNMWOOHESPU-UHFFFAOYSA-N 0.000 claims 1
- AQWGHENWBXBJNK-UHFFFAOYSA-N 4-[1-(cyanomethylsulfonyl)piperidin-4-yl]oxy-N-(5-fluoropyridin-2-yl)-N-(2-methylpropyl)benzenesulfonamide Chemical compound C(#N)CS(=O)(=O)N1CCC(CC1)OC1=CC=C(C=C1)S(=O)(=O)N(CC(C)C)C1=NC=C(C=C1)F AQWGHENWBXBJNK-UHFFFAOYSA-N 0.000 claims 1
- QBZDTPVHFOKKHV-UHFFFAOYSA-N 4-[methoxy-(1-methylsulfonylpiperidin-4-ylidene)methyl]-N-(2-methylpropyl)-N-[2-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)C(=C1CCN(CC1)S(=O)(=O)C)OC)C1=C(C=CC=C1)C(F)(F)F QBZDTPVHFOKKHV-UHFFFAOYSA-N 0.000 claims 1
- SRIMGNIRQHPAAJ-UHFFFAOYSA-N 5-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-3,4-dihydro-2H-1,5-benzoxazepine Chemical compound CS(=O)(=O)N1CCC(CC1)OC1=CC=C(C=C1)S(=O)(=O)N1C2=C(OCCC1)C=CC=C2 SRIMGNIRQHPAAJ-UHFFFAOYSA-N 0.000 claims 1
- TZJHHIALLMHTHE-UHFFFAOYSA-N 5-methyl-1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-2,3,4,5-tetrahydro-1-benzazepine Chemical compound CC1C2=C(N(CCC1)S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)C=CC=C2 TZJHHIALLMHTHE-UHFFFAOYSA-N 0.000 claims 1
- HFEYUGMUFQSEGA-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)-N-[(4-fluorophenyl)methyl]-N-(2-methylpropyl)pyridine-3-sulfonamide Chemical compound C(C)(=O)N1CCN(CC1)C1=CC=C(C=N1)S(=O)(=O)N(CC(C)C)CC1=CC=C(C=C1)F HFEYUGMUFQSEGA-UHFFFAOYSA-N 0.000 claims 1
- UUKXVYAQBHTTCV-UHFFFAOYSA-N 6-[4-(2-cyanoacetyl)piperazin-1-yl]-N-(4-fluorophenyl)-N-(2-methylpropyl)pyridine-3-sulfonamide Chemical compound C(#N)CC(=O)N1CCN(CC1)C1=CC=C(C=N1)S(=O)(=O)N(CC(C)C)C1=CC=C(C=C1)F UUKXVYAQBHTTCV-UHFFFAOYSA-N 0.000 claims 1
- GQZSDYMFKQPRDI-UHFFFAOYSA-N 6-fluoro-2-methyl-1-[4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]sulfonyl-3,4-dihydro-2H-quinoline Chemical compound FC=1C=C2CCC(N(C2=CC1)S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)C GQZSDYMFKQPRDI-UHFFFAOYSA-N 0.000 claims 1
- BGKMPCZEOYJLKA-UHFFFAOYSA-N N-(2-cyanophenyl)-N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxybenzenesulfonamide Chemical compound C(#N)C1=C(C=CC=C1)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)CC(C)C BGKMPCZEOYJLKA-UHFFFAOYSA-N 0.000 claims 1
- KZMMTBNGDZUTHC-UHFFFAOYSA-N N-(2-methylpropyl)-3-(4-methylsulfonylpiperazin-1-yl)-N-(2-phenylethyl)benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC(=CC=C1)N1CCN(CC1)S(=O)(=O)C)CCC1=CC=CC=C1 KZMMTBNGDZUTHC-UHFFFAOYSA-N 0.000 claims 1
- IMFPQGVKKJSPKM-UHFFFAOYSA-N N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxy-N-(pyridin-2-ylmethyl)benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)CC1=NC=CC=C1 IMFPQGVKKJSPKM-UHFFFAOYSA-N 0.000 claims 1
- SZISJOMVSJFKGN-UHFFFAOYSA-N N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxy-N-(pyridin-3-ylmethyl)benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)CC=1C=NC=CC1 SZISJOMVSJFKGN-UHFFFAOYSA-N 0.000 claims 1
- AKBGZOMDMJMIME-UHFFFAOYSA-N N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxy-N-(pyridin-4-ylmethyl)benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)CC1=CC=NC=C1 AKBGZOMDMJMIME-UHFFFAOYSA-N 0.000 claims 1
- QVDIVIPWVNWEEF-UHFFFAOYSA-N N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxy-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)C1=CC(=CC=C1)C(F)(F)F QVDIVIPWVNWEEF-UHFFFAOYSA-N 0.000 claims 1
- ZKBCHSJYWPOSGZ-UHFFFAOYSA-N N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxy-N-pyridin-2-ylbenzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)C1=NC=CC=C1 ZKBCHSJYWPOSGZ-UHFFFAOYSA-N 0.000 claims 1
- YDNGFCFYSONPQT-UHFFFAOYSA-N N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxy-N-pyridin-3-ylbenzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)C=1C=NC=CC1 YDNGFCFYSONPQT-UHFFFAOYSA-N 0.000 claims 1
- NVBAPAAISYCVRZ-UHFFFAOYSA-N N-(2-methylpropyl)-4-(1-methylsulfonylpiperidine-4-carbonyl)-N-[2-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)C(=O)C1CCN(CC1)S(=O)(=O)C)C1=C(C=CC=C1)C(F)(F)F NVBAPAAISYCVRZ-UHFFFAOYSA-N 0.000 claims 1
- YXQTUZBZOIRWAM-UHFFFAOYSA-N N-(2-methylpropyl)-4-(4-methylsulfonylpiperazin-1-yl)-N-(2-phenylethyl)benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)N1CCN(CC1)S(=O)(=O)C)CCC1=CC=CC=C1 YXQTUZBZOIRWAM-UHFFFAOYSA-N 0.000 claims 1
- PNFCGWUMSRHLEI-UHFFFAOYSA-N N-(2-methylpropyl)-4-(4-methylsulfonylpiperazin-1-yl)-N-(2-phenylpropyl)benzenesulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=CC=C(C=C1)N1CCN(CC1)S(=O)(=O)C)CC(C)C1=CC=CC=C1 PNFCGWUMSRHLEI-UHFFFAOYSA-N 0.000 claims 1
- OQQIUFAVSJAIJX-UHFFFAOYSA-N N-(2-methylpropyl)-5-(4-methylsulfonylpiperazin-1-yl)-N-(2-phenylethyl)pyridine-2-sulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C1=NC=C(C=C1)N1CCN(CC1)S(=O)(=O)C)CCC1=CC=CC=C1 OQQIUFAVSJAIJX-UHFFFAOYSA-N 0.000 claims 1
- GHQZDNUYKXKRSE-UHFFFAOYSA-N N-(2-methylpropyl)-6-(4-methylsulfonylpiperazin-1-yl)-N-(2-phenylethyl)pyridine-3-sulfonamide Chemical compound C(C(C)C)N(S(=O)(=O)C=1C=NC(=CC1)N1CCN(CC1)S(=O)(=O)C)CCC1=CC=CC=C1 GHQZDNUYKXKRSE-UHFFFAOYSA-N 0.000 claims 1
- MEDHWFJZSMUCHP-UHFFFAOYSA-N N-(3-chlorophenyl)-N-(2-methylpropyl)-5-[(1-methylsulfonylpiperidin-4-yl)amino]pyridine-2-sulfonamide Chemical compound ClC=1C=C(C=CC1)N(S(=O)(=O)C1=NC=C(C=C1)NC1CCN(CC1)S(=O)(=O)C)CC(C)C MEDHWFJZSMUCHP-UHFFFAOYSA-N 0.000 claims 1
- HKVJPSJYBUKRPX-UHFFFAOYSA-N N-(3-chlorophenyl)-N-(2-methylpropyl)-6-(1-methylsulfonylpiperidin-4-yl)oxypyridine-3-sulfonamide Chemical compound ClC=1C=C(C=CC1)N(S(=O)(=O)C=1C=NC(=CC1)OC1CCN(CC1)S(=O)(=O)C)CC(C)C HKVJPSJYBUKRPX-UHFFFAOYSA-N 0.000 claims 1
- ZHYWJQYTAOJWGR-UHFFFAOYSA-N N-(3-cyanophenyl)-N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxybenzenesulfonamide Chemical compound C(#N)C=1C=C(C=CC1)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)CC(C)C ZHYWJQYTAOJWGR-UHFFFAOYSA-N 0.000 claims 1
- NTWWBXUIMFTACU-UHFFFAOYSA-N N-(4-cyanophenyl)-N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxybenzenesulfonamide Chemical compound C(#N)C1=CC=C(C=C1)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)CC(C)C NTWWBXUIMFTACU-UHFFFAOYSA-N 0.000 claims 1
- FIMOAMSOCHFQDI-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-N-(2-methylpropyl)-4-(1-methylsulfonylpiperidin-4-yl)oxybenzenesulfonamide Chemical compound C(#N)C1=CC(=NC=C1)N(S(=O)(=O)C1=CC=C(C=C1)OC1CCN(CC1)S(=O)(=O)C)CC(C)C FIMOAMSOCHFQDI-UHFFFAOYSA-N 0.000 claims 1
- HTDOXUYPLWMEBN-UHFFFAOYSA-N N-(4-cyanopyridin-2-yl)-N-(2-methylpropyl)-6-(1-methylsulfonylpiperidin-4-yl)oxypyridine-3-sulfonamide Chemical compound C(#N)C1=CC(=NC=C1)N(S(=O)(=O)C=1C=NC(=CC1)OC1CCN(CC1)S(=O)(=O)C)CC(C)C HTDOXUYPLWMEBN-UHFFFAOYSA-N 0.000 claims 1
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- 239000004945 silicone rubber Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4468—Non condensed piperidines, e.g. piperocaine having a nitrogen directly attached in position 4, e.g. clebopride, fentanyl
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- A—HUMAN NECESSITIES
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
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- C—CHEMISTRY; METALLURGY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462002339P | 2014-05-23 | 2014-05-23 | |
| US62/002,339 | 2014-05-23 | ||
| PCT/EP2015/061347 WO2015177325A1 (fr) | 2014-05-23 | 2015-05-22 | Dérivés de benzène sulfonamide et leur utilisation comme modulateurs de rorc |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2949229A1 true CA2949229A1 (fr) | 2015-11-26 |
Family
ID=53264662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2949229A Abandoned CA2949229A1 (fr) | 2014-05-23 | 2015-05-22 | Derives de benzene sulfonamide et leur utilisation comme modulateurs de rorc |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP3145912A1 (fr) |
| JP (1) | JP2017521480A (fr) |
| KR (1) | KR20170007816A (fr) |
| CN (1) | CN106458991A (fr) |
| CA (1) | CA2949229A1 (fr) |
| MX (1) | MX2016015247A (fr) |
| RU (1) | RU2016149804A (fr) |
| WO (1) | WO2015177325A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11396503B2 (en) | 2017-09-30 | 2022-07-26 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Sulfonyl substituted bicyclic compound which acts as ROR inhibitor |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE057838T2 (hu) | 2016-06-07 | 2022-06-28 | Jacobio Pharmaceuticals Co Ltd | SHP2 inhibitorokként hasznos új heterociklusos származékok |
| CN108503584B (zh) * | 2017-02-27 | 2021-05-04 | 复旦大学 | 一种1,2,3,4-四氢喹啉磺酰胺类化合物及其应用 |
| TWI664175B (zh) | 2017-03-23 | 2019-07-01 | 大陸商北京加科思新藥研發有限公司 | 用於作為shp2抑制劑之新穎雜環衍生物 |
| CN109896998B (zh) * | 2017-12-10 | 2022-06-07 | 复旦大学 | 一种3,4-二氢异喹啉磺酰胺类化合物及其应用 |
| CN112839935A (zh) | 2018-09-26 | 2021-05-25 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
| CN113166061B (zh) * | 2018-11-27 | 2023-11-21 | 正大天晴药业集团股份有限公司 | 含有磺酰基结构的RORγ抑制剂 |
| WO2020205867A1 (fr) | 2019-04-02 | 2020-10-08 | Aligos Therapeutics, Inc. | Composés ciblant prmt5 |
| CN112830893A (zh) * | 2019-10-28 | 2021-05-25 | 成都倍特药业股份有限公司 | 一类RORγ抑制剂、其制备方法及其在医药上的应用 |
| JP7651708B2 (ja) * | 2020-12-31 | 2025-03-26 | シノハブ ファーマシューティカルズ カンパニー リミテッド | プラスミン阻害剤、そのための調製方法及びその応用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200522944A (en) * | 2003-12-23 | 2005-07-16 | Lilly Co Eli | CB1 modulator compounds |
| WO2008109154A1 (fr) * | 2007-03-08 | 2008-09-12 | Altiris Therapeutics, Inc. | Modulateurs de récepteur de chimiokine |
| CU20080028A6 (es) * | 2008-02-29 | 2011-02-24 | Ct Ingenieria Genetica Biotech | Compuestos químicos obtenidos in silico para la preparación de composiciones farmacéuticas para atenuar o inhibir la infección por virus dengue y otros flavivirus |
| US9216988B2 (en) * | 2011-12-22 | 2015-12-22 | Genentech, Inc. | Benzyl sulfonamide derivatives as RORc modulators |
| US9403800B2 (en) * | 2012-01-24 | 2016-08-02 | Chemregen, Inc. | Compounds for inhibition of cancer cell proliferation |
| TWI593678B (zh) * | 2012-04-27 | 2017-08-01 | 葛蘭素集團有限公司 | 作為類視色素相關孤兒受體γ(RORγ)調節劑之化合物、其醫藥組合物及用途 |
| HK1214598A1 (zh) * | 2012-12-10 | 2016-07-29 | F. Hoffmann-La Roche Ag | 作为rorc调节剂的苄基磺酰胺衍生物 |
-
2015
- 2015-05-22 KR KR1020167035789A patent/KR20170007816A/ko not_active Withdrawn
- 2015-05-22 EP EP15724296.7A patent/EP3145912A1/fr not_active Withdrawn
- 2015-05-22 JP JP2017513345A patent/JP2017521480A/ja active Pending
- 2015-05-22 MX MX2016015247A patent/MX2016015247A/es unknown
- 2015-05-22 RU RU2016149804A patent/RU2016149804A/ru unknown
- 2015-05-22 CA CA2949229A patent/CA2949229A1/fr not_active Abandoned
- 2015-05-22 WO PCT/EP2015/061347 patent/WO2015177325A1/fr not_active Ceased
- 2015-05-22 CN CN201580025888.7A patent/CN106458991A/zh active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11396503B2 (en) | 2017-09-30 | 2022-07-26 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Sulfonyl substituted bicyclic compound which acts as ROR inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015177325A1 (fr) | 2015-11-26 |
| MX2016015247A (es) | 2017-02-23 |
| EP3145912A1 (fr) | 2017-03-29 |
| KR20170007816A (ko) | 2017-01-20 |
| RU2016149804A (ru) | 2018-06-26 |
| CN106458991A (zh) | 2017-02-22 |
| JP2017521480A (ja) | 2017-08-03 |
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| FZDE | Discontinued |
Effective date: 20190522 |