JP4926402B2 - サイトカインインヒビターとしての１，２，３−トリアゾールアミド誘導体 - Google Patents
サイトカインインヒビターとしての１，２，３−トリアゾールアミド誘導体 Download PDFInfo
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- JP4926402B2 JP4926402B2 JP2004557232A JP2004557232A JP4926402B2 JP 4926402 B2 JP4926402 B2 JP 4926402B2 JP 2004557232 A JP2004557232 A JP 2004557232A JP 2004557232 A JP2004557232 A JP 2004557232A JP 4926402 B2 JP4926402 B2 JP 4926402B2
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- Japan
- Prior art keywords
- phenyl
- methyl
- methoxy
- tert
- butyl
- 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.)
- Expired - Lifetime
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- 102000004127 Cytokines Human genes 0.000 title abstract description 44
- 108090000695 Cytokines Proteins 0.000 title abstract description 44
- 239000003112 inhibitor Substances 0.000 title description 8
- OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical class NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 238000000034 method Methods 0.000 claims abstract description 27
- -1 hydroxy, hydroxy Chemical group 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- XOZZYNPAVVPHRQ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(O)=O)=C1 XOZZYNPAVVPHRQ-UHFFFAOYSA-N 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 150000004702 methyl esters Chemical class 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000004442 acylamino group Chemical group 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- VLHZHHLVRNKJKP-UHFFFAOYSA-N 5-amino-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2C(=C(C(O)=O)N=N2)N)=C1 VLHZHHLVRNKJKP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 150000001540 azides Chemical class 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- WCNFFKHKJLERFM-UHFFFAOYSA-N thiomorpholinyl sulfone group Chemical group N1(CCSCC1)S(=O)(=O)N1CCSCC1 WCNFFKHKJLERFM-UHFFFAOYSA-N 0.000 claims description 7
- ZCAGUOCUDGWENZ-UHFFFAOYSA-N thiomorpholinyl sulfoxide group Chemical group N1(CCSCC1)S(=O)N1CCSCC1 ZCAGUOCUDGWENZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 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 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 3
- MYKHBWFULXPPPE-UHFFFAOYSA-N 1-[5-[(3-amino-5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound COC1=C(N)C=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 MYKHBWFULXPPPE-UHFFFAOYSA-N 0.000 claims description 3
- QOEOCMUCZLZNLQ-HXUWFJFHSA-N 1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 QOEOCMUCZLZNLQ-HXUWFJFHSA-N 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 3
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004276 dioxalanyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- ZVNDOKIIMUJRSN-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-1-[5-[[3-(methanesulfonamido)-2-methoxy-5-(1-methylcyclopropyl)phenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxamide Chemical compound C1=C(C2(C)CC2)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C(C=1)=CC=C(C)C=1N1C=C(C(=O)NCC(C)(C)C)N=N1 ZVNDOKIIMUJRSN-UHFFFAOYSA-N 0.000 claims description 3
- HOPHKMATGGUWCH-HSZRJFAPSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[(2s)-3-hydroxy-2-phenylpropanoyl]triazol-1-yl]-4-methylbenzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)[C@H](CO)C=2C=CC=CC=2)=C1 HOPHKMATGGUWCH-HSZRJFAPSA-N 0.000 claims description 3
- PIVITOMPTXKKRX-HXUWFJFHSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-4-methyl-3-[4-[(2r)-2-phenylpropanoyl]triazol-1-yl]benzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)[C@H](C)C=2C=CC=CC=2)=C1 PIVITOMPTXKKRX-HXUWFJFHSA-N 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- CPXCJMGYKWMJBM-UHFFFAOYSA-N tert-butyl 4-[[[1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carbonyl]amino]methyl]piperidine-1-carboxylate Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CCN(CC2)C(=O)OC(C)(C)C)=C1 CPXCJMGYKWMJBM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 3
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims description 3
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims description 3
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- FFDIGMODELFUPV-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-(2-morpholin-4-ylethyl)triazole-4-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCCN2CCOCC2)=C1 FFDIGMODELFUPV-UHFFFAOYSA-N 0.000 claims description 2
- VRZHJBDQJUZDEO-QGZVFWFLSA-N 1-[5-[[5-(1,1,1,3,3,3-hexafluoropropan-2-yl)-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C(F)(F)F)C(F)(F)F)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 VRZHJBDQJUZDEO-QGZVFWFLSA-N 0.000 claims description 2
- BSCPSIHMYYIRHZ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-fluorophenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(F)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 BSCPSIHMYYIRHZ-UHFFFAOYSA-N 0.000 claims description 2
- SZCBXPJTUSQJOC-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1-methylpiperidin-3-yl)methyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CN(C)CCC2)=C1 SZCBXPJTUSQJOC-UHFFFAOYSA-N 0.000 claims description 2
- BEUFWZFQQOTSOA-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1-methylpiperidin-4-yl)methyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CCN(C)CC2)=C1 BEUFWZFQQOTSOA-UHFFFAOYSA-N 0.000 claims description 2
- DQLWSPCQROQYAG-SSEXGKCCSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1s)-2-(dimethylamino)-1-phenylethyl]-n-methyltriazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N(C)[C@H](CN(C)C)C=2C=CC=CC=2)=C1 DQLWSPCQROQYAG-SSEXGKCCSA-N 0.000 claims description 2
- FXKFUQGISSNGPZ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[2-(dimethylamino)-2-methylpropyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)N(C)C)=C1 FXKFUQGISSNGPZ-UHFFFAOYSA-N 0.000 claims description 2
- UYAPGVFFEFPITJ-QFIPXVFZSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]triazole-4-carboxamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CN(C=2C(=CC=C(C=2)C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C)(C)C)OC)C)N=N1 UYAPGVFFEFPITJ-QFIPXVFZSA-N 0.000 claims description 2
- CPPRGDCVJNIOIR-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-phenyltriazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NC=2C=CC=CC=2)=C1 CPPRGDCVJNIOIR-UHFFFAOYSA-N 0.000 claims description 2
- OPAOMYVCXCLDME-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-pyridin-4-yltriazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NC=2C=CN=CC=2)=C1 OPAOMYVCXCLDME-UHFFFAOYSA-N 0.000 claims description 2
- UYDMEPBGRBYBKD-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-3-fluoro-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC(F)=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 UYDMEPBGRBYBKD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- UDULYZBKGCUSCR-UHFFFAOYSA-N methyl 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C)(C)C)OC)=CC=C1C UDULYZBKGCUSCR-UHFFFAOYSA-N 0.000 claims description 2
- ULDIVZQLPBUHAG-UHFFFAOYSA-N n',n',2,2-tetramethylpropane-1,3-diamine Chemical compound CN(C)CC(C)(C)CN ULDIVZQLPBUHAG-UHFFFAOYSA-N 0.000 claims description 2
- TYEWNBMWTXMGOC-UHFFFAOYSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-4-methyl-3-[4-(morpholine-4-carbonyl)triazol-1-yl]benzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N2CCOCC2)=C1 TYEWNBMWTXMGOC-UHFFFAOYSA-N 0.000 claims description 2
- KAWCXOHGUGNDJC-UHFFFAOYSA-N n-benzyl-1-[3-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]phenyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=CC(N2N=NC(=C2)C(=O)NCC=2C=CC=CC=2)=C1 KAWCXOHGUGNDJC-UHFFFAOYSA-N 0.000 claims description 2
- WUGPWNUTZZUASG-UHFFFAOYSA-N n-benzyl-1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]triazole-4-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC=2C=CC=CC=2)=C1 WUGPWNUTZZUASG-UHFFFAOYSA-N 0.000 claims description 2
- JJDIIKNVGLYKMW-UHFFFAOYSA-N n-benzyl-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-fluorophenyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(F)C(N2N=NC(=C2)C(=O)NCC=2C=CC=CC=2)=C1 JJDIIKNVGLYKMW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- SUUUBXOVOSRGAM-UHFFFAOYSA-N tert-butyl 3-[[[1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carbonyl]amino]methyl]piperidine-1-carboxylate Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CN(CCC2)C(=O)OC(C)(C)C)=C1 SUUUBXOVOSRGAM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- XBUJGHAGSRFSEN-GOSISDBHSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(Cl)C(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 XBUJGHAGSRFSEN-GOSISDBHSA-N 0.000 claims 2
- WLQPPEXYIUYGHM-HSZRJFAPSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]-n-[(1r)-1-phenylpropyl]triazole-4-carboxamide Chemical compound N([C@H](CC)C=1C=CC=CC=1)C(=O)C(N=N1)=CN1C(C(=CC=1)Cl)=CC=1C(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC WLQPPEXYIUYGHM-HSZRJFAPSA-N 0.000 claims 2
- KNMFMVBWDXPKBO-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(1-pyridin-3-ylethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NC(C)C=2C=NC=CC=2)=C1 KNMFMVBWDXPKBO-UHFFFAOYSA-N 0.000 claims 2
- NSNSJQAJKXHCJR-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2-hydroxy-2-methylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)O)=C1 NSNSJQAJKXHCJR-UHFFFAOYSA-N 0.000 claims 2
- GQEQCKCNBUCAMO-HXUWFJFHSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1r)-1-cyclohexylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C2CCCCC2)=C1 GQEQCKCNBUCAMO-HXUWFJFHSA-N 0.000 claims 2
- DBGHYGSALMWLLM-XMMPIXPASA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1r)-1-phenylpropyl]triazole-4-carboxamide Chemical compound N([C@H](CC)C=1C=CC=CC=1)C(=O)C(N=N1)=CN1C(C(=CC=1)C)=CC=1C(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC DBGHYGSALMWLLM-XMMPIXPASA-N 0.000 claims 2
- RZLBVMIOOFAEBX-HHHXNRCGSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1s)-2-(dimethylamino)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](CN(C)C)C=2C=CC=CC=2)=C1 RZLBVMIOOFAEBX-HHHXNRCGSA-N 0.000 claims 2
- MOYBVQRLCMRPHZ-HHHXNRCGSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1s)-2-methoxy-1-phenylethyl]triazole-4-carboxamide Chemical compound N([C@H](COC)C=1C=CC=CC=1)C(=O)C(N=N1)=CN1C(C(=CC=1)C)=CC=1C(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC MOYBVQRLCMRPHZ-HHHXNRCGSA-N 0.000 claims 2
- BCZVTYMHNFUTNX-GOSISDBHSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(2r)-3,3-dimethylbutan-2-yl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C(C)(C)C)=C1 BCZVTYMHNFUTNX-GOSISDBHSA-N 0.000 claims 2
- UGWSSKXHAHYOAM-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[3-(dimethylamino)-2,2-dimethylpropyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)CN(C)C)=C1 UGWSSKXHAHYOAM-UHFFFAOYSA-N 0.000 claims 2
- CMUUDXZLEPHKMF-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-cyclopentyltriazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NC2CCCC2)=C1 CMUUDXZLEPHKMF-UHFFFAOYSA-N 0.000 claims 2
- GLZIQUGSLFRMPD-KRWDZBQOSA-N 5-amino-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(2s)-3,3-dimethylbutan-2-yl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2C(=C(C(=O)N[C@@H](C)C(C)(C)C)N=N2)N)=C1 GLZIQUGSLFRMPD-KRWDZBQOSA-N 0.000 claims 2
- ZQJWVDFJLKWVCM-UHFFFAOYSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-(cyclohexanecarbonyl)triazol-1-yl]-4-methylbenzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)C2CCCCC2)=C1 ZQJWVDFJLKWVCM-UHFFFAOYSA-N 0.000 claims 2
- CRCTZWNJRMZUIO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical group FC(F)(F)[CH]C(F)(F)F CRCTZWNJRMZUIO-UHFFFAOYSA-N 0.000 claims 1
- OBAHWSLSHGVOTK-LJQANCHMSA-N 1-[3-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]phenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=CC(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 OBAHWSLSHGVOTK-LJQANCHMSA-N 0.000 claims 1
- OAHPEUSJDOZCAG-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2,3-dimethylphenyl]-n-(2-morpholin-4-ylethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC(C)=C(C)C(N2N=NC(=C2)C(=O)NCCN2CCOCC2)=C1 OAHPEUSJDOZCAG-UHFFFAOYSA-N 0.000 claims 1
- VTRVTYITLGKQKR-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(Cl)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 VTRVTYITLGKQKR-UHFFFAOYSA-N 0.000 claims 1
- IEDNIQALLRPMFJ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]-n-(pyridin-3-ylmethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(Cl)C(N2N=NC(=C2)C(=O)NCC=2C=NC=CC=2)=C1 IEDNIQALLRPMFJ-UHFFFAOYSA-N 0.000 claims 1
- TWMNPSJTUSFPEC-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 TWMNPSJTUSFPEC-UHFFFAOYSA-N 0.000 claims 1
- MKXAJPGTSOMAFW-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2-morpholin-4-ylethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCCN2CCOCC2)=C1 MKXAJPGTSOMAFW-UHFFFAOYSA-N 0.000 claims 1
- LIIRZZMKVKMXHG-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2-phenylpropan-2-yl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NC(C)(C)C=2C=CC=CC=2)=C1 LIIRZZMKVKMXHG-UHFFFAOYSA-N 0.000 claims 1
- HPGQOUXJTRWYTC-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2-piperidin-1-ylethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCCN2CCCCC2)=C1 HPGQOUXJTRWYTC-UHFFFAOYSA-N 0.000 claims 1
- QFXBWQVIBRTSLX-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(piperidin-4-ylmethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CCNCC2)=C1 QFXBWQVIBRTSLX-UHFFFAOYSA-N 0.000 claims 1
- OIRLBRWAGYPJRL-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(pyridin-3-ylmethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC=2C=NC=CC=2)=C1 OIRLBRWAGYPJRL-UHFFFAOYSA-N 0.000 claims 1
- UXZKSNGYAVJNHF-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(pyridin-4-ylmethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC=2C=CN=CC=2)=C1 UXZKSNGYAVJNHF-UHFFFAOYSA-N 0.000 claims 1
- GQEQCKCNBUCAMO-FQEVSTJZSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1s)-1-cyclohexylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@@H](C)C2CCCCC2)=C1 GQEQCKCNBUCAMO-FQEVSTJZSA-N 0.000 claims 1
- MPTIBCHEZCLPEU-FQEVSTJZSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1s)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@@H](C)C=2C=CC=CC=2)=C1 MPTIBCHEZCLPEU-FQEVSTJZSA-N 0.000 claims 1
- BCZVTYMHNFUTNX-SFHVURJKSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(2s)-3,3-dimethylbutan-2-yl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@@H](C)C(C)(C)C)=C1 BCZVTYMHNFUTNX-SFHVURJKSA-N 0.000 claims 1
- FAPHDFKIZBBHLR-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[2-(dimethylamino)ethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCCN(C)C)=C1 FAPHDFKIZBBHLR-UHFFFAOYSA-N 0.000 claims 1
- ZMJCFFJNHFXJGK-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-cyclopropyltriazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NC2CC2)=C1 ZMJCFFJNHFXJGK-UHFFFAOYSA-N 0.000 claims 1
- XSDWIMCEOVEIHX-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-methyltriazole-4-carboxamide Chemical compound N1=NC(C(=O)NC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C)(C)C)OC)=CC=C1C XSDWIMCEOVEIHX-UHFFFAOYSA-N 0.000 claims 1
- REDFPWZHDDCNFO-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(N)=O)=C1 REDFPWZHDDCNFO-UHFFFAOYSA-N 0.000 claims 1
- GGONDCZAKSGASR-UHFFFAOYSA-N 3-(4-benzoyltriazol-1-yl)-n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-4-methylbenzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)C=2C=CC=CC=2)=C1 GGONDCZAKSGASR-UHFFFAOYSA-N 0.000 claims 1
- MPFDLGZRXMLAAA-UHFFFAOYSA-N 5-amino-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[3-(dimethylamino)-2,2-dimethylpropyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2C(=C(C(=O)NCC(C)(C)CN(C)C)N=N2)N)=C1 MPFDLGZRXMLAAA-UHFFFAOYSA-N 0.000 claims 1
- AZQHRFIZPVTYNX-UHFFFAOYSA-N CC(C)(C)C(C=C1NS(C)(=O)=O)=CC(NC(C2=CC=C(C)C(N3N=NC(C(O)=O)=C3)=C2)=O)=C1OC.CNCC1=CC=CC=C1 Chemical compound CC(C)(C)C(C=C1NS(C)(=O)=O)=CC(NC(C2=CC=C(C)C(N3N=NC(C(O)=O)=C3)=C2)=O)=C1OC.CNCC1=CC=CC=C1 AZQHRFIZPVTYNX-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- QGIOQDHBGIQYNC-UHFFFAOYSA-N ethyl 1-[5-[[5-(1,1,1,3,3,3-hexafluoropropan-2-yl)-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OCC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C(F)(F)F)C(F)(F)F)OC)=CC=C1C QGIOQDHBGIQYNC-UHFFFAOYSA-N 0.000 claims 1
- MKSRIAPRXGGSJY-UHFFFAOYSA-N ethyl 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OCC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C)(C)C)OC)=CC=C1Cl MKSRIAPRXGGSJY-UHFFFAOYSA-N 0.000 claims 1
- SSTIHKVVJKBUKR-UHFFFAOYSA-N ethyl 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OCC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C)(C)C)OC)=CC=C1C SSTIHKVVJKBUKR-UHFFFAOYSA-N 0.000 claims 1
- MUSXKAUTAHERDY-UHFFFAOYSA-N methyl 1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1C1=CC(C(=O)NC=2C(=CC=C(C=2)C(C)(C)C)OC)=CC=C1C MUSXKAUTAHERDY-UHFFFAOYSA-N 0.000 claims 1
- OSZZMYWVIGDKMW-UHFFFAOYSA-N methyl 1-[5-[[3-(methanesulfonamido)-2-methoxy-5-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(F)(F)F)OC)=CC=C1C OSZZMYWVIGDKMW-UHFFFAOYSA-N 0.000 claims 1
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| US43051902P | 2002-11-27 | 2002-11-27 | |
| US60/430,519 | 2002-11-27 | ||
| PCT/US2003/037104 WO2004050642A1 (en) | 2002-11-27 | 2003-11-20 | 1, 2, 3- triazole amide derivatives as cytokine inhibitors |
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| JP2006514940A JP2006514940A (ja) | 2006-05-18 |
| JP2006514940A5 JP2006514940A5 (enExample) | 2007-01-18 |
| JP4926402B2 true JP4926402B2 (ja) | 2012-05-09 |
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| US7591994B2 (en) * | 2002-12-13 | 2009-09-22 | Immunomedics, Inc. | Camptothecin-binding moiety conjugates |
| US7511042B2 (en) * | 2003-12-03 | 2009-03-31 | Boehringer Ingelheim Pharmaceuticals, Inc. | Triazole compounds |
| US7485657B2 (en) * | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| WO2006109846A1 (ja) * | 2005-04-06 | 2006-10-19 | Takeda Pharmaceutical Company Limited | トリアゾール誘導体およびその用途 |
| JP2008540526A (ja) * | 2005-05-12 | 2008-11-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ハロゲン化アリールのビスアミノ化 |
| CN101228137B (zh) * | 2005-07-25 | 2010-09-29 | 弗·哈夫曼-拉罗切有限公司 | 被取代的三唑衍生物和它们作为神经激肽3受体拮抗剂的用途 |
| BRPI0712795A2 (pt) * | 2006-07-07 | 2012-09-04 | Boehringer Ingelheim Int | derivados de heteroarila substituìdos com fenila e uso dos mesmos como agentes antitumorais |
| PE20090837A1 (es) * | 2007-07-02 | 2009-07-24 | Boehringer Ingelheim Int | Nuevos compuestos quimicos |
| US20100240657A1 (en) * | 2007-07-02 | 2010-09-23 | Boehringer Ingelheim International Gmbh | Chemical compounds |
| TW201014860A (en) | 2008-09-08 | 2010-04-16 | Boehringer Ingelheim Int | New chemical compounds |
| JP5603869B2 (ja) | 2008-09-29 | 2014-10-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規化合物 |
| US8569316B2 (en) | 2009-02-17 | 2013-10-29 | Boehringer Ingelheim International Gmbh | Pyrimido [5,4-D] pyrimidine derivatives for the inhibition of tyrosine kinases |
| JP2011057661A (ja) | 2009-08-14 | 2011-03-24 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
| US8865703B2 (en) | 2010-03-26 | 2014-10-21 | Boehringer Ingelheim International Gmbh | Pyridyltriazoles |
| JP5871896B2 (ja) | 2010-03-26 | 2016-03-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｂ−ｒａｆキナーゼインヒビター |
| US8710055B2 (en) | 2010-12-21 | 2014-04-29 | Boehringer Ingelheim International Gmbh | Triazolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| US8889684B2 (en) | 2011-02-02 | 2014-11-18 | Boehringer Ingelheim International Gmbh | Azaindolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| CA2893239A1 (en) * | 2012-12-03 | 2014-06-12 | F. Hoffmann-La Roche Ag | Substituted triazole and imidazole compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| FR2732967B1 (fr) | 1995-04-11 | 1997-07-04 | Sanofi Sa | 1-phenylpyrazole-3-carboxamides substitues, actifs sur la neurotensine, leur preparation, les compositions pharmaceutiques en contenant |
| AU761361B2 (en) * | 1998-09-25 | 2003-06-05 | Astrazeneca Ab | Benzamide derivatives and their use as cytokine inhibitors |
| BR9915534B1 (pt) | 1998-10-23 | 2011-04-19 | 1-piridil substituìdo)-1,2,4-triazóis inseticidas. | |
| UA73492C2 (en) | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| US20010044445A1 (en) | 1999-04-08 | 2001-11-22 | Bamaung Nwe Y. | Azole inhibitors of cytokine production |
| US7297708B2 (en) | 2001-09-06 | 2007-11-20 | Bristol-Myers Squibb Company | Heteroaromatic substituted cyclopropane as corticotropin releasing hormone ligands |
| AU2002341921B2 (en) | 2001-10-04 | 2007-05-31 | Merck Sharp & Dohme Corp. | Heteroaryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| ATE511840T1 (de) | 2001-10-09 | 2011-06-15 | Amgen Inc | Imidazolderivate als entzündungshemmende mittel |
| WO2003063781A2 (en) | 2002-01-29 | 2003-08-07 | Merck & Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| US7511042B2 (en) * | 2003-12-03 | 2009-03-31 | Boehringer Ingelheim Pharmaceuticals, Inc. | Triazole compounds |
| US7485657B2 (en) * | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
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2003
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- 2003-11-20 JP JP2004557232A patent/JP4926402B2/ja not_active Expired - Lifetime
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| ES2265596T3 (es) | 2007-02-16 |
| DE60306193D1 (de) | 2006-07-27 |
| DE60306193T2 (de) | 2006-10-12 |
| ATE329909T1 (de) | 2006-07-15 |
| WO2004050642A1 (en) | 2004-06-17 |
| US7569568B2 (en) | 2009-08-04 |
| EP1567507A1 (en) | 2005-08-31 |
| EP1567507B1 (en) | 2006-06-14 |
| US7166628B2 (en) | 2007-01-23 |
| AU2003294388A1 (en) | 2004-06-23 |
| US20070032492A1 (en) | 2007-02-08 |
| JP2006514940A (ja) | 2006-05-18 |
| CA2507184A1 (en) | 2004-06-17 |
| CA2507184C (en) | 2012-01-10 |
| US20040102492A1 (en) | 2004-05-27 |
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