JP2006522750A - 代謝性症候群ならびに関連の疾患および障害を治療するために、11β−ヒドロキシステロイドデヒドロゲナーゼ1型阻害剤および抗高血圧剤を使用する併用療法 - Google Patents
代謝性症候群ならびに関連の疾患および障害を治療するために、11β−ヒドロキシステロイドデヒドロゲナーゼ1型阻害剤および抗高血圧剤を使用する併用療法 Download PDFInfo
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- JP2006522750A JP2006522750A JP2006504357A JP2006504357A JP2006522750A JP 2006522750 A JP2006522750 A JP 2006522750A JP 2006504357 A JP2006504357 A JP 2006504357A JP 2006504357 A JP2006504357 A JP 2006504357A JP 2006522750 A JP2006522750 A JP 2006522750A
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- phenyl
- alkyl
- aryl
- methanone
- methyl
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- 238000002648 combination therapy Methods 0.000 title claims abstract description 27
- 239000002220 antihypertensive agent Substances 0.000 title claims abstract description 26
- 229940030600 antihypertensive agent Drugs 0.000 title claims abstract description 26
- 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 title claims abstract description 17
- 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 title claims abstract description 17
- 239000003112 inhibitor Substances 0.000 title claims abstract description 14
- 208000001145 Metabolic Syndrome Diseases 0.000 title claims description 17
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 title claims description 17
- 208000037765 diseases and disorders Diseases 0.000 title abstract description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 19
- 206010020772 Hypertension Diseases 0.000 claims abstract description 15
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 12
- 208000008589 Obesity Diseases 0.000 claims abstract description 12
- 235000020824 obesity Nutrition 0.000 claims abstract description 12
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 10
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims description 689
- 125000001072 heteroaryl group Chemical group 0.000 claims description 459
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 439
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 265
- 125000000217 alkyl group Chemical group 0.000 claims description 241
- 239000001257 hydrogen Substances 0.000 claims description 156
- 229910052739 hydrogen Inorganic materials 0.000 claims description 156
- 150000002431 hydrogen Chemical class 0.000 claims description 146
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 139
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 109
- 125000004122 cyclic group Chemical group 0.000 claims description 104
- 229920006395 saturated elastomer Polymers 0.000 claims description 103
- 125000004043 oxo group Chemical group O=* 0.000 claims description 101
- 229910052757 nitrogen Inorganic materials 0.000 claims description 95
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 94
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 90
- 125000005843 halogen group Chemical group 0.000 claims description 85
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 83
- 230000003287 optical effect Effects 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 79
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 78
- 125000004432 carbon atom Chemical group C* 0.000 claims description 75
- 229910052760 oxygen Inorganic materials 0.000 claims description 70
- 125000004104 aryloxy group Chemical group 0.000 claims description 68
- 239000001301 oxygen Chemical group 0.000 claims description 66
- 229910052717 sulfur Chemical group 0.000 claims description 59
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 58
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 57
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 57
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 57
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 56
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 56
- 239000011593 sulfur Chemical group 0.000 claims description 55
- 125000005842 heteroatom Chemical group 0.000 claims description 49
- 229940126558 11β-HSD1 inhibitor Drugs 0.000 claims description 46
- 125000002619 bicyclic group Chemical group 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 35
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 229940002612 prodrug Drugs 0.000 claims description 26
- 239000000651 prodrug Substances 0.000 claims description 26
- 125000004951 trihalomethoxy group Chemical group 0.000 claims description 26
- 239000000556 agonist Substances 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- 125000005110 aryl thio group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- BZVYPVRTYHVXQF-UHFFFAOYSA-N [5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-(2-methylpiperidin-1-yl)methanone Chemical compound CC1CCCCN1C(=O)C1=C2N=C(C=3OC=CC=3)C=C(C(F)(F)F)N2N=C1 BZVYPVRTYHVXQF-UHFFFAOYSA-N 0.000 claims description 10
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 9
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- ZIHAUZPDTWGAGA-UHFFFAOYSA-N (5,7-diphenylpyrazolo[1,5-a]pyrimidin-2-yl)-(2-methylpiperidin-1-yl)methanone Chemical compound CC1CCCCN1C(=O)C1=NN2C(C=3C=CC=CC=3)=CC(C=3C=CC=CC=3)=NC2=C1 ZIHAUZPDTWGAGA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- MLHZDTXTESQRTD-UHFFFAOYSA-N [5-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-piperidin-1-ylmethanone Chemical compound C1=C2N=C(C)C=C(C(F)(F)F)N2N=C1C(=O)N1CCCCC1 MLHZDTXTESQRTD-UHFFFAOYSA-N 0.000 claims description 6
- QRROROQYZZXGBJ-UHFFFAOYSA-N [5-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-piperidin-1-ylmethanone Chemical compound N=1N2C(C(F)(F)F)=CC(C=3C=CC=CC=3)=NC2=CC=1C(=O)N1CCCCC1 QRROROQYZZXGBJ-UHFFFAOYSA-N 0.000 claims description 6
- CZOAFVKPCSRZOI-UHFFFAOYSA-N [5-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-piperidin-1-ylmethanone Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3C=CC=CC=3)=NC2=C1C(=O)N1CCCCC1 CZOAFVKPCSRZOI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 6
- QTSHYHWZCCQNPO-UHFFFAOYSA-N n-cyclohexyl-n,5-dimethyl-7-phenylpyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C1=C2N=C(C)C=C(C=3C=CC=CC=3)N2N=C1C(=O)N(C)C1CCCCC1 QTSHYHWZCCQNPO-UHFFFAOYSA-N 0.000 claims description 6
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- RQVNPEVSYLEJSV-UHFFFAOYSA-N (2,6-dimethylpiperidin-1-yl)-[7-(4-ethoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound C1=CC(OCC)=CC=C1C1=CC(C)=NC2=CC(C(=O)N3C(CCCC3C)C)=NN12 RQVNPEVSYLEJSV-UHFFFAOYSA-N 0.000 claims description 4
- LYIFABCEPRQWQI-UHFFFAOYSA-N (2-methylpiperidin-1-yl)-[5-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound CC1CCCCN1C(=O)C1=NN2C(C(F)(F)F)=CC(C)=NC2=C1 LYIFABCEPRQWQI-UHFFFAOYSA-N 0.000 claims description 4
- JGRMHLNCOFTDRJ-UHFFFAOYSA-N (2-methylpiperidin-1-yl)-[5-naphthalen-1-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound CC1CCCCN1C(=O)C1=NN2C(C(F)(F)F)=CC(C=3C4=CC=CC=C4C=CC=3)=NC2=C1 JGRMHLNCOFTDRJ-UHFFFAOYSA-N 0.000 claims description 4
- RMODZCVFVYOBED-UHFFFAOYSA-N (2-methylpiperidin-1-yl)-[5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound CC1CCCCN1C(=O)C1=C2N=C(C=3SC=CC=3)C=C(C(F)(F)F)N2N=C1 RMODZCVFVYOBED-UHFFFAOYSA-N 0.000 claims description 4
- DMMLDRWUYKWPBU-UHFFFAOYSA-N (3,6-dibromopyrazolo[1,5-a]pyrimidin-2-yl)-piperidin-1-ylmethanone Chemical compound N=1N2C=C(Br)C=NC2=C(Br)C=1C(=O)N1CCCCC1 DMMLDRWUYKWPBU-UHFFFAOYSA-N 0.000 claims description 4
- HFKCGKDMHGFQPE-UHFFFAOYSA-N (4-benzylpiperazin-1-yl)-[5-(4-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)N3CCN(CC=4C=CC=CC=4)CC3)C=NN2C(C(F)(F)F)=C1 HFKCGKDMHGFQPE-UHFFFAOYSA-N 0.000 claims description 4
- KLVNDWJMPOPRQD-UHFFFAOYSA-N (4-benzylpiperazin-1-yl)-[5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3SC=CC=3)=NC2=C1C(=O)N(CC1)CCN1CC1=CC=CC=C1 KLVNDWJMPOPRQD-UHFFFAOYSA-N 0.000 claims description 4
- ZQKPEGVYICVUKT-UHFFFAOYSA-N (5,7-diphenylpyrazolo[1,5-a]pyrimidin-2-yl)-piperidin-1-ylmethanone Chemical compound C1=C2N=C(C=3C=CC=CC=3)C=C(C=3C=CC=CC=3)N2N=C1C(=O)N1CCCCC1 ZQKPEGVYICVUKT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- ZTLJTWNUGYFNOO-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinolin-2-yl-[5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound N=1C2=CC(C(=O)N3CC4=CC=CC=C4CC3)=NN2C(C(F)(F)F)=CC=1C1=CC=CS1 ZTLJTWNUGYFNOO-UHFFFAOYSA-N 0.000 claims description 4
- ZNJBJSJCYDHLOQ-UHFFFAOYSA-N 3,4-dihydro-2h-quinolin-1-yl-[5-(4-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)N3C4=CC=CC=C4CCC3)C=NN2C(C(F)(F)F)=C1 ZNJBJSJCYDHLOQ-UHFFFAOYSA-N 0.000 claims description 4
- YRVQVNYRNOTDSR-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-n-cyclohexyl-n-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3C=C4OCOC4=CC=3)=NC2=C1C(=O)N(C)C1CCCCC1 YRVQVNYRNOTDSR-UHFFFAOYSA-N 0.000 claims description 4
- LWQLDLBVTYCLQT-UHFFFAOYSA-N [3-bromo-5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-(3,4-dihydro-2h-quinolin-1-yl)methanone Chemical compound N=1C2=C(Br)C(C(=O)N3C4=CC=CC=C4CCC3)=NN2C(C(F)(F)F)=CC=1C1=CC=CO1 LWQLDLBVTYCLQT-UHFFFAOYSA-N 0.000 claims description 4
- KZQKGTMCIHZZJZ-UHFFFAOYSA-N [3-bromo-5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-piperidin-1-ylmethanone Chemical compound N=1N2C(C(F)(F)F)=CC(C=3OC=CC=3)=NC2=C(Br)C=1C(=O)N1CCCCC1 KZQKGTMCIHZZJZ-UHFFFAOYSA-N 0.000 claims description 4
- RFKOCDXSTXVFMM-UHFFFAOYSA-N [4-(4-fluorophenyl)piperazin-1-yl]-[5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound C1=CC(F)=CC=C1N1CCN(C(=O)C2=NN3C(=CC(=NC3=C2)C=2SC=CC=2)C(F)(F)F)CC1 RFKOCDXSTXVFMM-UHFFFAOYSA-N 0.000 claims description 4
- OHILVJRDWLTZLQ-UHFFFAOYSA-N [5-(1,3-benzodioxol-5-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3C=C4OCOC4=CC=3)=NC2=C1C(=O)N1CCCC1 OHILVJRDWLTZLQ-UHFFFAOYSA-N 0.000 claims description 4
- YHWWUXFNTWSSIO-UHFFFAOYSA-N [5-(4-bromophenyl)-3-chloro-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-pyrrolidin-1-ylmethanone Chemical compound N=1N2C(C(F)(F)F)=CC(C=3C=CC(Br)=CC=3)=NC2=C(Cl)C=1C(=O)N1CCCC1 YHWWUXFNTWSSIO-UHFFFAOYSA-N 0.000 claims description 4
- SFUQDBQUORTYLG-UHFFFAOYSA-N [5-(4-bromophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-(2-methylpiperidin-1-yl)methanone Chemical compound CC1CCCCN1C(=O)C1=C2N=C(C=3C=CC(Br)=CC=3)C=C(C(F)(F)F)N2N=C1 SFUQDBQUORTYLG-UHFFFAOYSA-N 0.000 claims description 4
- WANDXXHDRIBGLY-UHFFFAOYSA-N [5-(4-bromophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-morpholin-4-ylmethanone Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3C=CC(Br)=CC=3)=NC2=C1C(=O)N1CCOCC1 WANDXXHDRIBGLY-UHFFFAOYSA-N 0.000 claims description 4
- GTFFRCRFPPNQPG-UHFFFAOYSA-N [5-(4-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-thiomorpholin-4-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(C(=O)N3CCSCC3)=NN2C(C(F)(F)F)=C1 GTFFRCRFPPNQPG-UHFFFAOYSA-N 0.000 claims description 4
- OZGHGJFSSWPCNA-UHFFFAOYSA-N [5-(4-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-morpholin-4-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)N3CCOCC3)C=NN2C(C(F)(F)F)=C1 OZGHGJFSSWPCNA-UHFFFAOYSA-N 0.000 claims description 4
- BLPMCYGERRNQSC-UHFFFAOYSA-N [5-(4-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)N3CCCC3)C=NN2C(C(F)(F)F)=C1 BLPMCYGERRNQSC-UHFFFAOYSA-N 0.000 claims description 4
- YZEIHZPMIUPJRH-UHFFFAOYSA-N [5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-pyrrolidin-1-ylmethanone Chemical compound N=1N2C(C(F)(F)F)=CC(C=3OC=CC=3)=NC2=CC=1C(=O)N1CCCC1 YZEIHZPMIUPJRH-UHFFFAOYSA-N 0.000 claims description 4
- ALLAXDLUGQMUBZ-UHFFFAOYSA-N [5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C2N=C(C=3OC=CC=3)C=C(C(F)(F)F)N2N=C1 ALLAXDLUGQMUBZ-UHFFFAOYSA-N 0.000 claims description 4
- BRHKYYGGLQYEPB-UHFFFAOYSA-N [5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]-thiomorpholin-4-ylmethanone Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3OC=CC=3)=NC2=C1C(=O)N1CCSCC1 BRHKYYGGLQYEPB-UHFFFAOYSA-N 0.000 claims description 4
- XQCAMTPRKIYUTD-UHFFFAOYSA-N [5-naphthalen-1-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-piperidin-1-ylmethanone Chemical compound N=1N2C(C(F)(F)F)=CC(C=3C4=CC=CC=C4C=CC=3)=NC2=CC=1C(=O)N1CCCCC1 XQCAMTPRKIYUTD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
- FCCISPLISCEDCP-UHFFFAOYSA-N azepan-1-yl-(5,7-diphenylpyrazolo[1,5-a]pyrimidin-3-yl)methanone Chemical compound C1=NN2C(C=3C=CC=CC=3)=CC(C=3C=CC=CC=3)=NC2=C1C(=O)N1CCCCCC1 FCCISPLISCEDCP-UHFFFAOYSA-N 0.000 claims description 4
- YIXSGTRDFWXVGM-UHFFFAOYSA-N azepan-1-yl-[3-bromo-5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound N=1N2C(C(F)(F)F)=CC(C=3OC=CC=3)=NC2=C(Br)C=1C(=O)N1CCCCCC1 YIXSGTRDFWXVGM-UHFFFAOYSA-N 0.000 claims description 4
- RIYNNDAOGXNYFD-UHFFFAOYSA-N azepan-1-yl-[3-chloro-5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound N=1N2C(C(F)(F)F)=CC(C=3SC=CC=3)=NC2=C(Cl)C=1C(=O)N1CCCCCC1 RIYNNDAOGXNYFD-UHFFFAOYSA-N 0.000 claims description 4
- PBHKXCYWSZPJIT-UHFFFAOYSA-N azepan-1-yl-[5-(4-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(C(=O)N3CCCCCC3)=NN2C(C(F)(F)F)=C1 PBHKXCYWSZPJIT-UHFFFAOYSA-N 0.000 claims description 4
- CJBMERVAMZMDSS-UHFFFAOYSA-N azepan-1-yl-[5-(4-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)N3CCCCCC3)C=NN2C(C(F)(F)F)=C1 CJBMERVAMZMDSS-UHFFFAOYSA-N 0.000 claims description 4
- UFMHYTUAKUPDRG-UHFFFAOYSA-N azepan-1-yl-[7-(trifluoromethyl)-5-(3,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound COC1=C(OC)C(OC)=CC(C2=NC3=C(C(=O)N4CCCCCC4)C=NN3C(=C2)C(F)(F)F)=C1 UFMHYTUAKUPDRG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- MJRFHDWVUOQCHI-UHFFFAOYSA-N furan-2-yl-[4-[5-(4-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carbonyl]piperazin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(C(=O)N3CCN(CC3)C(=O)C=3OC=CC=3)=NN2C(C(F)(F)F)=C1 MJRFHDWVUOQCHI-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
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- YRCWUMHRRJVNFB-UHFFFAOYSA-N azepan-1-yl-[5-(4-chlorophenyl)-2-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound CC1=NN2C(C(F)(F)F)=CC(C=3C=CC(Cl)=CC=3)=NC2=C1C(=O)N1CCCCCC1 YRCWUMHRRJVNFB-UHFFFAOYSA-N 0.000 claims description 2
- ZPRMVXIWDAGRNB-UHFFFAOYSA-N azepan-1-yl-[5-(4-fluorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=NC2=CC(C(=O)N3CCCCCC3)=NN2C(C(F)(F)F)=C1 ZPRMVXIWDAGRNB-UHFFFAOYSA-N 0.000 claims description 2
- WIPKOJFJCNOQLA-UHFFFAOYSA-N azepan-1-yl-[5-(4-nitrophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl]methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NC2=CC(C(=O)N3CCCCCC3)=NN2C(C(F)(F)F)=C1 WIPKOJFJCNOQLA-UHFFFAOYSA-N 0.000 claims description 2
- SOCDFQDHAGVMQG-UHFFFAOYSA-N azepan-1-yl-[5-(furan-2-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3OC=CC=3)=NC2=C1C(=O)N1CCCCCC1 SOCDFQDHAGVMQG-UHFFFAOYSA-N 0.000 claims description 2
- ILBDOFYZWPFZAY-UHFFFAOYSA-N azepan-1-yl-[5-cyclopropyl-7-(difluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound C1=NN2C(C(F)F)=CC(C3CC3)=NC2=C1C(=O)N1CCCCCC1 ILBDOFYZWPFZAY-UHFFFAOYSA-N 0.000 claims description 2
- KPUHGPXZPOFCLH-UHFFFAOYSA-N azepan-1-yl-[5-thiophen-2-yl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone Chemical compound C1=NN2C(C(F)(F)F)=CC(C=3SC=CC=3)=NC2=C1C(=O)N1CCCCCC1 KPUHGPXZPOFCLH-UHFFFAOYSA-N 0.000 claims description 2
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- ZINWADPKZHBBEQ-UHFFFAOYSA-N ethyl 1-[5-(3-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)C1=C2N=C(C=3C=C(OC)C=CC=3)C=C(C(F)(F)F)N2N=C1 ZINWADPKZHBBEQ-UHFFFAOYSA-N 0.000 claims description 2
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- AEFHHMQJRBXPQR-UHFFFAOYSA-N ethyl 4-[5-(1,3-benzodioxol-5-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carbonyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)C1=NN2C(C(F)(F)F)=CC(C=3C=C4OCOC4=CC=3)=NC2=C1 AEFHHMQJRBXPQR-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003937 drug carrier Substances 0.000 claims 4
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- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 3
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- JIUOGBKTFGUCKG-UHFFFAOYSA-N (2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl)-(2,4,4-trimethyl-6-azabicyclo[3.2.1]octan-6-yl)methanone Chemical compound C1C(C(CC2(C)C)C)CC2N1C(=O)C1=CC=CC2=C1OC(C)C2C JIUOGBKTFGUCKG-UHFFFAOYSA-N 0.000 claims 2
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- YBJYREROQOWSCS-UHFFFAOYSA-N 1h-indol-4-yl-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)C1=CC=CC2=C1C=CN2 YBJYREROQOWSCS-UHFFFAOYSA-N 0.000 claims 2
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- JUDJWZJHJGVFNL-UHFFFAOYSA-N 2-[[5-(4-aminophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-1-(4-nitrophenyl)ethanone Chemical compound N=1N=C(C=2C=CC(N)=CC=2)N(C)C=1SCC(=O)C1=CC=C([N+]([O-])=O)C=C1 JUDJWZJHJGVFNL-UHFFFAOYSA-N 0.000 claims 2
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- FVPNQJQFMJMQBP-UHFFFAOYSA-N 3-(2-bromophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound BrC1=CC=CC=C1C1=NN=C2N1CCCCC2 FVPNQJQFMJMQBP-UHFFFAOYSA-N 0.000 claims 2
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- LPQUUTFFETVGJJ-UHFFFAOYSA-N 3h-benzimidazol-5-yl-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1=C2NC=NC2=CC(C(=O)N2C3CC(CC(C)(C)C3)(C2)C)=C1 LPQUUTFFETVGJJ-UHFFFAOYSA-N 0.000 claims 2
- UTJJXMWOLIFXSW-UHFFFAOYSA-N 4-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-indole-3-carboxylic acid Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)C1=CC=CC2=C1C(C(O)=O)=CN2 UTJJXMWOLIFXSW-UHFFFAOYSA-N 0.000 claims 2
- WMNAHCAAPNEUSQ-UHFFFAOYSA-N 4-[5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl WMNAHCAAPNEUSQ-UHFFFAOYSA-N 0.000 claims 2
- CAIPLUDSZJCLRO-UHFFFAOYSA-N 4-fluoro-n-[4-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)phenyl]benzenesulfonamide Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1 CAIPLUDSZJCLRO-UHFFFAOYSA-N 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
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- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
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- NNTUSYMOTQWYOW-UHFFFAOYSA-N (2,6-dimethylmorpholin-4-yl)-[4-(naphthalen-1-yloxymethyl)phenyl]methanone Chemical compound C1C(C)OC(C)CN1C(=O)C(C=C1)=CC=C1COC1=CC=CC2=CC=CC=C12 NNTUSYMOTQWYOW-UHFFFAOYSA-N 0.000 claims 1
- ZGQCDPXTQARJRN-UHFFFAOYSA-N (2,6-dimethylmorpholin-4-yl)-[4-(naphthalen-2-yloxymethyl)phenyl]methanone Chemical compound C1C(C)OC(C)CN1C(=O)C(C=C1)=CC=C1COC1=CC=C(C=CC=C2)C2=C1 ZGQCDPXTQARJRN-UHFFFAOYSA-N 0.000 claims 1
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- CGDBBVPEBGIJLJ-UHFFFAOYSA-N (2-amino-3h-benzimidazol-5-yl)-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1=C2NC(N)=NC2=CC(C(=O)N2C3CC(CC(C)(C)C3)(C2)C)=C1 CGDBBVPEBGIJLJ-UHFFFAOYSA-N 0.000 claims 1
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- QPAATTRMFDTNHF-UHFFFAOYSA-N (2-chlorophenyl)-(6-fluoro-2-methyl-3,4-dihydro-2h-quinolin-1-yl)methanone Chemical compound CC1CCC2=CC(F)=CC=C2N1C(=O)C1=CC=CC=C1Cl QPAATTRMFDTNHF-UHFFFAOYSA-N 0.000 claims 1
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- RVOGFGIPWLCTPQ-UHFFFAOYSA-N (2-methyl-3h-benzimidazol-5-yl)-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C1=CC=C(NC(C)=N2)C2=C1 RVOGFGIPWLCTPQ-UHFFFAOYSA-N 0.000 claims 1
- LDSRBZAVERTFSJ-UHFFFAOYSA-N (2-methylphenyl)-(2-methylpiperidin-1-yl)methanone Chemical compound CC1CCCCN1C(=O)C1=CC=CC=C1C LDSRBZAVERTFSJ-UHFFFAOYSA-N 0.000 claims 1
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- FGVHXWMGZMGETK-UHFFFAOYSA-N (6-methyl-1h-indol-3-yl)-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C1=CNC2=CC(C)=CC=C21 FGVHXWMGZMGETK-UHFFFAOYSA-N 0.000 claims 1
- MUDWIJMMYALAGU-UHFFFAOYSA-N (6-nitro-1h-indol-3-yl)-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound [O-][N+](=O)C1=CC=C2C(C(=O)N3C4CC(CC(C)(C)C4)(C3)C)=CNC2=C1 MUDWIJMMYALAGU-UHFFFAOYSA-N 0.000 claims 1
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- HVMDTGSDSRRYTQ-UHFFFAOYSA-N (7-hydroxy-3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-phenylmethanone Chemical compound C12CC(O)CCC2CCCN1C(=O)C1=CC=CC=C1 HVMDTGSDSRRYTQ-UHFFFAOYSA-N 0.000 claims 1
- LBVCKSDEHLTWSN-UHFFFAOYSA-N (7-nitro-1h-indol-3-yl)-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1=CC=C2C(C(=O)N3C4CC(CC(C)(C)C4)(C3)C)=CNC2=C1[N+]([O-])=O LBVCKSDEHLTWSN-UHFFFAOYSA-N 0.000 claims 1
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- WKFABOAGIPBQAF-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)-2-[[5-[(2,4-dimethylanilino)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound N=1N=C(SCC(=O)N2C3=CC=CC=C3CCC2)N(CC)C=1CNC1=CC=C(C)C=C1C WKFABOAGIPBQAF-UHFFFAOYSA-N 0.000 claims 1
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- KKWSMSBRJWEUDS-UHFFFAOYSA-N 1-(4-benzylpiperidin-1-yl)-2-benzylsulfanylethanone Chemical compound C1CC(CC=2C=CC=CC=2)CCN1C(=O)CSCC1=CC=CC=C1 KKWSMSBRJWEUDS-UHFFFAOYSA-N 0.000 claims 1
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- LABLZKSZGSYJKL-UHFFFAOYSA-N 1-(4-bromophenyl)-2-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound N=1N=C(C=2OC=CC=2)N(C)C=1SCC(=O)C1=CC=C(Br)C=C1 LABLZKSZGSYJKL-UHFFFAOYSA-N 0.000 claims 1
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- ROIJMAYXBGSVHD-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[[4-methyl-5-[4-(trifluoromethyl)pyridin-3-yl]-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound N=1N=C(C=2C(=CC=NC=2)C(F)(F)F)N(C)C=1SCC(=O)C1=CC=C(Cl)C=C1 ROIJMAYXBGSVHD-UHFFFAOYSA-N 0.000 claims 1
- SNVPQIRFGLLEPM-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexyl-n,5-dimethylpyrazole-4-carboxamide Chemical compound C1=NN(C=2C=CC(Cl)=CC=2)C(C)=C1C(=O)N(C)C1CCCCC1 SNVPQIRFGLLEPM-UHFFFAOYSA-N 0.000 claims 1
- TXOIGTCLNINOIR-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexyl-n-methyl-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=NN(C=2C=CC(Cl)=CC=2)C(C(F)(F)F)=C1C(=O)N(C)C1CCCCC1 TXOIGTCLNINOIR-UHFFFAOYSA-N 0.000 claims 1
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- FITANMHEOCKQFD-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[(4-methyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]butan-1-one;2-[(4-methyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound N=1N=C(C=2C=CC=CC=2)N(C)C=1SCCCC(=O)C1=CC=C(F)C=C1.CN1C(SCC(=O)C=2C=C3CCCCC3=CC=2)=NN=C1C1=CC=CC=C1 FITANMHEOCKQFD-UHFFFAOYSA-N 0.000 claims 1
- JGMZKVWWDYIGBR-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[[4-(2-phenylethyl)-5-pyridin-4-yl-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CSC(N1CCC=2C=CC=CC=2)=NN=C1C1=CC=NC=C1 JGMZKVWWDYIGBR-UHFFFAOYSA-N 0.000 claims 1
- LWBSCBZYYQRHKA-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[[4-methyl-5-(2-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CSC(N1C)=NN=C1C1=CC=CC=C1C LWBSCBZYYQRHKA-UHFFFAOYSA-N 0.000 claims 1
- XXMKZAKAWTXDHT-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[[4-methyl-5-(4-nitrophenyl)-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CSC(N1C)=NN=C1C1=CC=C([N+]([O-])=O)C=C1 XXMKZAKAWTXDHT-UHFFFAOYSA-N 0.000 claims 1
- NMKQVFRVDXXVSD-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[[5-phenyl-4-(2-phenylethyl)-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CSC(N1CCC=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 NMKQVFRVDXXVSD-UHFFFAOYSA-N 0.000 claims 1
- CTPKJVXHHPQCCL-UHFFFAOYSA-N 1-(4-methylphenyl)-2-[(4-methyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]ethanone Chemical compound C1=CC(C)=CC=C1C(=O)CSC(N1C)=NN=C1C1=CC=CC=C1 CTPKJVXHHPQCCL-UHFFFAOYSA-N 0.000 claims 1
- HMHFTZDXVSPCRP-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-2-[[4-(2-phenylethyl)-5-pyridin-4-yl-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)CSC(N1CCC=2C=CC=CC=2)=NN=C1C1=CC=NC=C1 HMHFTZDXVSPCRP-UHFFFAOYSA-N 0.000 claims 1
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- JHPVFCZLMIXTIE-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-2-[[4-methyl-5-(4-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]ethanone Chemical compound COC1=CC=C(Cl)C=C1C(=O)CSC(N1C)=NN=C1C1=CC=C(C)C=C1 JHPVFCZLMIXTIE-UHFFFAOYSA-N 0.000 claims 1
- VAGSHINATNLVMH-UHFFFAOYSA-N 1-(azepan-1-yl)-3-(4-chlorophenyl)sulfanylpropan-1-one Chemical compound C1=CC(Cl)=CC=C1SCCC(=O)N1CCCCCC1 VAGSHINATNLVMH-UHFFFAOYSA-N 0.000 claims 1
- DMYFTZJMMDFIOF-UHFFFAOYSA-N 1-(azepane-1-carbonyl)fluoren-9-one Chemical compound C=1C=CC=2C3=CC=CC=C3C(=O)C=2C=1C(=O)N1CCCCCC1 DMYFTZJMMDFIOF-UHFFFAOYSA-N 0.000 claims 1
- NDFBRHTXABKGQJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-n-cyclooctylpyrrolidine-2-carboxamide Chemical compound C1CCN(S(=O)(=O)C=2C=CC=CC=2)C1C(=O)NC1CCCCCCC1 NDFBRHTXABKGQJ-UHFFFAOYSA-N 0.000 claims 1
- GIGGJMZITBFZDE-UHFFFAOYSA-N 1-(thiophene-2-carbonyl)-2,3-dihydroquinolin-4-one Chemical compound C1CC(=O)C2=CC=CC=C2N1C(=O)C1=CC=CS1 GIGGJMZITBFZDE-UHFFFAOYSA-N 0.000 claims 1
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- OROJQMWAAMSHCB-UHFFFAOYSA-N 2-[(6-amino-1,3-benzothiazol-2-yl)sulfanyl]-n-cyclohexylacetamide Chemical compound S1C2=CC(N)=CC=C2N=C1SCC(=O)NC1CCCCC1 OROJQMWAAMSHCB-UHFFFAOYSA-N 0.000 claims 1
- KDLAKIOJEPTQDT-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)tetrazol-5-yl]sulfanyl-n-phenyl-n-propan-2-ylacetamide Chemical compound C=1C=CC=CC=1N(C(C)C)C(=O)CSC1=NN=NN1C1=CC(C)=CC=C1C KDLAKIOJEPTQDT-UHFFFAOYSA-N 0.000 claims 1
- FZAXAPQYHLECOI-UHFFFAOYSA-N 2-[1-(2,6-dimethylmorpholin-4-yl)-1-oxopropan-2-yl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C)C(=O)N1CC(C)OC(C)C1 FZAXAPQYHLECOI-UHFFFAOYSA-N 0.000 claims 1
- SAIAGGQCMGMEIA-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)sulfonylbenzimidazol-2-yl]sulfanyl-n-(thiophen-2-ylmethyl)acetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C2=CC=CC=C2N=C1SCC(=O)NCC1=CC=CS1 SAIAGGQCMGMEIA-UHFFFAOYSA-N 0.000 claims 1
- WHZXXYYHHHQBQY-UHFFFAOYSA-N 2-[1-(azepan-1-yl)-3-methyl-1-oxobutan-2-yl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C(C)C)C(=O)N1CCCCCC1 WHZXXYYHHHQBQY-UHFFFAOYSA-N 0.000 claims 1
- TVUZQZKYWYADOX-UHFFFAOYSA-N 2-[1-morpholin-4-yl-3-(4-nitrophenyl)-1-oxopropan-2-yl]isoindole-1,3-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC(C(=O)N1CCOCC1)N1C(=O)C2=CC=CC=C2C1=O TVUZQZKYWYADOX-UHFFFAOYSA-N 0.000 claims 1
- XDUFXJIZTFOCLG-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-2-adamantyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CC1(C=2C=CC(Cl)=CC=2)C(C2)CC3CC2CC1C3 XDUFXJIZTFOCLG-UHFFFAOYSA-N 0.000 claims 1
- GGKNHRRHTQJTTL-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-2-adamantyl]-1-[4-(4-methoxyphenyl)piperazin-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)CC2(C3CC4CC(C3)CC2C4)C=2C=CC(Cl)=CC=2)CC1 GGKNHRRHTQJTTL-UHFFFAOYSA-N 0.000 claims 1
- OGOUTJBZNBTLDZ-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-2-adamantyl]-n-(2-hydroxyethyl)acetamide Chemical compound C1C2CC(C3)CC1CC3C2(CC(=O)NCCO)C1=CC=C(Cl)C=C1 OGOUTJBZNBTLDZ-UHFFFAOYSA-N 0.000 claims 1
- BOKVJFHTLJCVEB-UHFFFAOYSA-N 2-[2-(5-bicyclo[2.2.1]hept-2-enylamino)-4-oxo-1,3-thiazol-5-yl]-n-(2-chlorophenyl)acetamide Chemical compound ClC1=CC=CC=C1NC(=O)CC1C(=O)N=C(NC2C3CC(C=C3)C2)S1 BOKVJFHTLJCVEB-UHFFFAOYSA-N 0.000 claims 1
- HPOGVCKERGTYKP-UHFFFAOYSA-N 2-[2-[[(2-amino-2-oxoethyl)-[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C=1C(OC)=CC(C(=O)N(CC(N)=O)CC=2C(=CC=CC=2)OCC(O)=O)=CC=1C(=O)C1=CC=CC=N1 HPOGVCKERGTYKP-UHFFFAOYSA-N 0.000 claims 1
- JYVBDKZKULSJKM-UHFFFAOYSA-N 2-[2-[[2-methoxyethyl-[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C=1C(OC)=CC(C(=O)C=2N=CC=CC=2)=CC=1C(=O)N(CCOC)CC1=CC=CC=C1OCC(O)=O JYVBDKZKULSJKM-UHFFFAOYSA-N 0.000 claims 1
- LLOIADUZZZXHIZ-UHFFFAOYSA-N 2-[2-[[[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]-(3-methylbutyl)amino]methyl]phenoxy]acetic acid Chemical compound C=1C(OC)=CC(C(=O)N(CCC(C)C)CC=2C(=CC=CC=2)OCC(O)=O)=CC=1C(=O)C1=CC=CC=N1 LLOIADUZZZXHIZ-UHFFFAOYSA-N 0.000 claims 1
- IHPWLYWFNHBBJS-UHFFFAOYSA-N 2-[2-[[[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]-methylamino]methyl]phenoxy]acetic acid Chemical compound C=1C(OC)=CC(C(=O)N(C)CC=2C(=CC=CC=2)OCC(O)=O)=CC=1C(=O)C1=CC=CC=N1 IHPWLYWFNHBBJS-UHFFFAOYSA-N 0.000 claims 1
- NQGOXWWAGHYVOM-UHFFFAOYSA-N 2-[2-[[[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]-pyridin-4-ylamino]methyl]phenoxy]acetic acid Chemical compound C=1C(OC)=CC(C(=O)N(CC=2C(=CC=CC=2)OCC(O)=O)C=2C=CN=CC=2)=CC=1C(=O)C1=CC=CC=N1 NQGOXWWAGHYVOM-UHFFFAOYSA-N 0.000 claims 1
- BAYIZJYSJMYCJL-UHFFFAOYSA-N 2-[2-[[cyclopentyl-[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C=1C(OC)=CC(C(=O)N(CC=2C(=CC=CC=2)OCC(O)=O)C2CCCC2)=CC=1C(=O)C1=CC=CC=N1 BAYIZJYSJMYCJL-UHFFFAOYSA-N 0.000 claims 1
- SOQRFSOECBDGBK-UHFFFAOYSA-N 2-[2-[[cyclopropyl-[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C=1C(OC)=CC(C(=O)N(CC=2C(=CC=CC=2)OCC(O)=O)C2CC2)=CC=1C(=O)C1=CC=CC=N1 SOQRFSOECBDGBK-UHFFFAOYSA-N 0.000 claims 1
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- MBRMOBDUCLMTMR-UHFFFAOYSA-N 2-[3-(azepane-1-carbonyl)phenyl]isoindole-1,3-dione Chemical compound C=1C=CC(N2C(C3=CC=CC=C3C2=O)=O)=CC=1C(=O)N1CCCCCC1 MBRMOBDUCLMTMR-UHFFFAOYSA-N 0.000 claims 1
- WSEFWDLSBIPVAF-UHFFFAOYSA-N 2-[3-[4-(2-chlorophenyl)piperazin-1-yl]-3-oxopropyl]isoindole-1,3-dione Chemical compound ClC1=CC=CC=C1N1CCN(C(=O)CCN2C(C3=CC=CC=C3C2=O)=O)CC1 WSEFWDLSBIPVAF-UHFFFAOYSA-N 0.000 claims 1
- GVQXUZISFDJWHR-UHFFFAOYSA-N 2-[3-imidazol-1-ylpropyl-[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]amino]acetic acid Chemical compound C=1C(OC)=CC(C(=O)N(CCCN2C=NC=C2)CC(O)=O)=CC=1C(=O)C1=CC=CC=N1 GVQXUZISFDJWHR-UHFFFAOYSA-N 0.000 claims 1
- BMJFHITXZQCGRM-UHFFFAOYSA-N 2-[4-(1,3-benzothiazol-2-yl)piperazin-1-yl]-n-cyclohexylacetamide Chemical compound C1CN(C=2SC3=CC=CC=C3N=2)CCN1CC(=O)NC1CCCCC1 BMJFHITXZQCGRM-UHFFFAOYSA-N 0.000 claims 1
- ZHONOIXVBFLUNK-UHFFFAOYSA-N 2-[4-(2-methoxyethyl)-5-(2-methoxyethylsulfanyl)-1,2,4-triazol-3-yl]-1-methylpiperidine Chemical compound COCCN1C(SCCOC)=NN=C1C1N(C)CCCC1 ZHONOIXVBFLUNK-UHFFFAOYSA-N 0.000 claims 1
- QNYYKYDVCRJADV-UHFFFAOYSA-N 2-[4-(2-methoxyethyl)-5-(2-methoxyethylsulfanyl)-1,2,4-triazol-3-yl]phenol Chemical compound COCCN1C(SCCOC)=NN=C1C1=CC=CC=C1O QNYYKYDVCRJADV-UHFFFAOYSA-N 0.000 claims 1
- DBFZXNIOYMDGPC-UHFFFAOYSA-N 2-[4-(2-methoxyethyl)-5-(pyridin-2-ylmethylsulfanyl)-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CCOC)C=1SCC1=CC=CC=N1 DBFZXNIOYMDGPC-UHFFFAOYSA-N 0.000 claims 1
- BLNIYEIMTLMHGY-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]-n-(1-phenylethyl)propanamide Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C(=O)NC(C)C1=CC=CC=C1 BLNIYEIMTLMHGY-UHFFFAOYSA-N 0.000 claims 1
- JFJNSJBPRUNIHJ-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethyl)-5-(pyridin-2-ylmethylsulfanyl)-1,2,4-triazol-3-yl]phenol Chemical compound OC1=CC=CC=C1C(N1CCN2CCCCC2)=NN=C1SCC1=CC=CC=N1 JFJNSJBPRUNIHJ-UHFFFAOYSA-N 0.000 claims 1
- JBDYWCYCAGIOLC-UHFFFAOYSA-N 2-[4-(3,3,4-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)phenyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C=C1)=CC=C1C(=O)N(C1)C2CC1C(C)C(C)(C)C2 JBDYWCYCAGIOLC-UHFFFAOYSA-N 0.000 claims 1
- HYIOYEXEHHOTRT-UHFFFAOYSA-N 2-[4-(3-methoxypropyl)-5-(pyridin-2-ylmethylsulfanyl)-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CCCOC)C=1SCC1=CC=CC=N1 HYIOYEXEHHOTRT-UHFFFAOYSA-N 0.000 claims 1
- YFQOUUOEKOIYSD-UHFFFAOYSA-N 2-[4-(adamantane-1-carbonylamino)phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1NC(=O)C1(C2)CC(C3)CC2CC3C1 YFQOUUOEKOIYSD-UHFFFAOYSA-N 0.000 claims 1
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- BVKGZHNESWEZBH-UHFFFAOYSA-N 2-[4-(cyclopropylmethyl)-5-(2-methoxyethylsulfanyl)-1,2,4-triazol-3-yl]phenol Chemical compound C1CC1CN1C(SCCOC)=NN=C1C1=CC=CC=C1O BVKGZHNESWEZBH-UHFFFAOYSA-N 0.000 claims 1
- MNLIOEDPEDTPIH-UHFFFAOYSA-N 2-[4-(cyclopropylmethyl)-5-(pyridin-2-ylmethylsulfanyl)-1,2,4-triazol-3-yl]phenol Chemical compound OC1=CC=CC=C1C(N1CC2CC2)=NN=C1SCC1=CC=CC=N1 MNLIOEDPEDTPIH-UHFFFAOYSA-N 0.000 claims 1
- JTLLXTGXSYXFGS-UHFFFAOYSA-N 2-[4-cyclopropyl-5-(2-methoxyethylsulfanyl)-1,2,4-triazol-3-yl]-1-methylpiperidine Chemical compound C1CC1N1C(SCCOC)=NN=C1C1CCCCN1C JTLLXTGXSYXFGS-UHFFFAOYSA-N 0.000 claims 1
- DWXHVTUOXMDSRV-UHFFFAOYSA-N 2-[4-cyclopropyl-5-(2-methoxyethylsulfanyl)-1,2,4-triazol-3-yl]phenol Chemical compound C1CC1N1C(SCCOC)=NN=C1C1=CC=CC=C1O DWXHVTUOXMDSRV-UHFFFAOYSA-N 0.000 claims 1
- WUSCLOLDRCUNRE-UHFFFAOYSA-N 2-[4-cyclopropyl-5-(pyridin-2-ylmethylsulfanyl)-1,2,4-triazol-3-yl]phenol Chemical compound OC1=CC=CC=C1C(N1C2CC2)=NN=C1SCC1=CC=CC=N1 WUSCLOLDRCUNRE-UHFFFAOYSA-N 0.000 claims 1
- QLGVFLQRHXIJDO-UHFFFAOYSA-N 2-[4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O QLGVFLQRHXIJDO-UHFFFAOYSA-N 0.000 claims 1
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- TUGNHRLVKXOBPA-UHFFFAOYSA-N 2-[4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 TUGNHRLVKXOBPA-UHFFFAOYSA-N 0.000 claims 1
- KSRPZEGSDPGTEG-UHFFFAOYSA-N 2-[4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC=C(C)C=C1 KSRPZEGSDPGTEG-UHFFFAOYSA-N 0.000 claims 1
- WJVLMPBAYGZROF-UHFFFAOYSA-N 2-[4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 WJVLMPBAYGZROF-UHFFFAOYSA-N 0.000 claims 1
- ZUDCBCMSXZRDDS-UHFFFAOYSA-N 2-[4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 ZUDCBCMSXZRDDS-UHFFFAOYSA-N 0.000 claims 1
- NYYAQIMMHUNUBK-UHFFFAOYSA-N 2-[4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 NYYAQIMMHUNUBK-UHFFFAOYSA-N 0.000 claims 1
- LWNOEQJRDVDQBM-UHFFFAOYSA-N 2-[4-ethyl-5-[(4-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 LWNOEQJRDVDQBM-UHFFFAOYSA-N 0.000 claims 1
- GTSUZRJCUKMHSE-UHFFFAOYSA-N 2-[4-ethyl-5-[(4-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 GTSUZRJCUKMHSE-UHFFFAOYSA-N 0.000 claims 1
- KMTWAGYEIDEIFJ-UHFFFAOYSA-N 2-[4-ethyl-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 KMTWAGYEIDEIFJ-UHFFFAOYSA-N 0.000 claims 1
- RDZOSHIUFUVJIK-UHFFFAOYSA-N 2-[4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O RDZOSHIUFUVJIK-UHFFFAOYSA-N 0.000 claims 1
- MNMAXWCOHZMSRC-UHFFFAOYSA-N 2-[4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O MNMAXWCOHZMSRC-UHFFFAOYSA-N 0.000 claims 1
- KCLMSKPHJFWGLT-UHFFFAOYSA-N 2-[4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 KCLMSKPHJFWGLT-UHFFFAOYSA-N 0.000 claims 1
- QUKLUPQXVGHINW-UHFFFAOYSA-N 2-[4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 QUKLUPQXVGHINW-UHFFFAOYSA-N 0.000 claims 1
- KLHCUYOHQHRXJT-UHFFFAOYSA-N 2-[4-ethyl-5-[[4-(thiadiazol-4-yl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 KLHCUYOHQHRXJT-UHFFFAOYSA-N 0.000 claims 1
- GDCBRBDLEVSCMB-UHFFFAOYSA-N 2-[4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 GDCBRBDLEVSCMB-UHFFFAOYSA-N 0.000 claims 1
- QDXABEWTQGXEKY-UHFFFAOYSA-N 2-[4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 QDXABEWTQGXEKY-UHFFFAOYSA-N 0.000 claims 1
- UBNQYRRJVNGYFE-UHFFFAOYSA-N 2-[5-(2-methoxyethylsulfanyl)-4-(2-piperidin-1-ylethyl)-1,2,4-triazol-3-yl]phenol Chemical compound C1CCCCN1CCN1C(SCCOC)=NN=C1C1=CC=CC=C1O UBNQYRRJVNGYFE-UHFFFAOYSA-N 0.000 claims 1
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- GFPRHIJUJNNSMM-UHFFFAOYSA-N 2-[5-(2-methoxyethylsulfanyl)-4-(3-methoxypropyl)-1,2,4-triazol-3-yl]phenol Chemical compound COCCCN1C(SCCOC)=NN=C1C1=CC=CC=C1O GFPRHIJUJNNSMM-UHFFFAOYSA-N 0.000 claims 1
- ZNWUQVNZPMRDGO-UHFFFAOYSA-N 2-[5-(2-morpholin-4-ylethylsulfanyl)-4-(2-phenylethyl)-1,2,4-triazol-3-yl]phenol Chemical compound OC1=CC=CC=C1C(N1CCC=2C=CC=CC=2)=NN=C1SCCN1CCOCC1 ZNWUQVNZPMRDGO-UHFFFAOYSA-N 0.000 claims 1
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- ICAMFZGTGGJIOT-UHFFFAOYSA-N 2-[5-(cyclohexylmethylsulfanyl)-4-ethyl-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1CCCCC1 ICAMFZGTGGJIOT-UHFFFAOYSA-N 0.000 claims 1
- GVUVLSNZMGWSGD-UHFFFAOYSA-N 2-[5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl GVUVLSNZMGWSGD-UHFFFAOYSA-N 0.000 claims 1
- ORJYMIDFCWMEOD-UHFFFAOYSA-N 2-[5-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl ORJYMIDFCWMEOD-UHFFFAOYSA-N 0.000 claims 1
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- AEGHNVIUXMRJME-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-(2-methoxyphenyl)-1-pyrrolidin-1-ylpropan-1-one Chemical compound COC1=CC=CC=C1C(C=1C=C2OCOC2=CC=1)CC(=O)N1CCCC1 AEGHNVIUXMRJME-UHFFFAOYSA-N 0.000 claims 1
- SQUUWDKKCXOUFN-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O SQUUWDKKCXOUFN-UHFFFAOYSA-N 0.000 claims 1
- APYSFURDEKPNPG-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 APYSFURDEKPNPG-UHFFFAOYSA-N 0.000 claims 1
- SWPSVWPGUSAAQP-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 SWPSVWPGUSAAQP-UHFFFAOYSA-N 0.000 claims 1
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- VACLYSBTPLBLMK-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O VACLYSBTPLBLMK-UHFFFAOYSA-N 0.000 claims 1
- JKKYVKCAZRJCRX-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 JKKYVKCAZRJCRX-UHFFFAOYSA-N 0.000 claims 1
- VDPYERUAJIQQRJ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-5-(cyclohexylmethylsulfanyl)-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1CCCCC1 VDPYERUAJIQQRJ-UHFFFAOYSA-N 0.000 claims 1
- BKRAEGKYBYPRRF-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl BKRAEGKYBYPRRF-UHFFFAOYSA-N 0.000 claims 1
- RHPXENSHHDVUSA-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-5-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl RHPXENSHHDVUSA-UHFFFAOYSA-N 0.000 claims 1
- ALUDBMDJTAIHFW-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-5-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC=CC=C1Cl ALUDBMDJTAIHFW-UHFFFAOYSA-N 0.000 claims 1
- IPONEIAWWGEKND-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-5-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 IPONEIAWWGEKND-UHFFFAOYSA-N 0.000 claims 1
- IIAIJBPOOLHYLV-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-5-[(4-bromophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC=C(Br)C=C1 IIAIJBPOOLHYLV-UHFFFAOYSA-N 0.000 claims 1
- JUNRCDSERGLGRF-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-5-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound C1=C2OCOC2=CC(C2=NN=C(SCC=3C(=CC=4OCOC=4C=3)Cl)N2CC)=C1 JUNRCDSERGLGRF-UHFFFAOYSA-N 0.000 claims 1
- IZVZFYJEVTWHHM-UHFFFAOYSA-N 3-(1,3-dioxoisoindol-2-yl)-n-(2-methylcyclohexyl)propanamide Chemical compound CC1CCCCC1NC(=O)CCN1C(=O)C2=CC=CC=C2C1=O IZVZFYJEVTWHHM-UHFFFAOYSA-N 0.000 claims 1
- FDHALABOVMMWHS-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O FDHALABOVMMWHS-UHFFFAOYSA-N 0.000 claims 1
- QSZRMSSHWVTXMK-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 QSZRMSSHWVTXMK-UHFFFAOYSA-N 0.000 claims 1
- MMOJEUZXXNJMSE-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=C(OC)C=C1 MMOJEUZXXNJMSE-UHFFFAOYSA-N 0.000 claims 1
- QZFFKLBSOVYAFA-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-4-ethyl-5-[(4-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 QZFFKLBSOVYAFA-UHFFFAOYSA-N 0.000 claims 1
- ICWYPJGIOFEUFW-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-4-ethyl-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 ICWYPJGIOFEUFW-UHFFFAOYSA-N 0.000 claims 1
- FOIPLQZASNTOMD-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 FOIPLQZASNTOMD-UHFFFAOYSA-N 0.000 claims 1
- CTULBSGKGGOXEI-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-5-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=CC=C1Cl CTULBSGKGGOXEI-UHFFFAOYSA-N 0.000 claims 1
- LZWGTGSDCKNULB-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-5-[(4-bromophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=C(Br)C=C1 LZWGTGSDCKNULB-UHFFFAOYSA-N 0.000 claims 1
- QWOZYRJMINCFCO-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-5-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound C1=CC=C2SC(C3=NN=C(SCC=4C(=CC=5OCOC=5C=4)Cl)N3CC)=CC2=C1 QWOZYRJMINCFCO-UHFFFAOYSA-N 0.000 claims 1
- OKOUKEMKLYMBMZ-UHFFFAOYSA-N 3-(1-benzylimidazol-2-yl)sulfanyl-n-cyclohexylpropanamide Chemical compound C1CCCCC1NC(=O)CCSC1=NC=CN1CC1=CC=CC=C1 OKOUKEMKLYMBMZ-UHFFFAOYSA-N 0.000 claims 1
- LLUHQFWZRQUSJD-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-4-(2-methylprop-2-enyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(=C)C)C(C=2C(=CC(Cl)=CC=2)Cl)=N1 LLUHQFWZRQUSJD-UHFFFAOYSA-N 0.000 claims 1
- CHVNFDHQTPIKSU-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-4-(furan-2-ylmethyl)-5-methylsulfanyl-1,2,4-triazole Chemical compound C=1C=COC=1CN1C(SC)=NN=C1C1=CC=C(Cl)C=C1Cl CHVNFDHQTPIKSU-UHFFFAOYSA-N 0.000 claims 1
- JMUBCVRQTQJXDS-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-4-prop-2-enyl-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC(Cl)=CC=C1C1=NNC(=S)N1CC=C JMUBCVRQTQJXDS-UHFFFAOYSA-N 0.000 claims 1
- NJQBEFPUXBYGQT-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-5,5-dimethyl-6h-[1,2,4]triazolo[3,4-a]isoquinoline Chemical compound N12C(C)(C)CC3=CC=CC=C3C2=NN=C1C1=CC=C(Cl)C=C1Cl NJQBEFPUXBYGQT-UHFFFAOYSA-N 0.000 claims 1
- FTQFYENWBZENCJ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-6,6-dimethyl-5,7-dihydro-1h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound N12CC(C)(C)CNC2=NN=C1C1=CC=C(Cl)C=C1Cl FTQFYENWBZENCJ-UHFFFAOYSA-N 0.000 claims 1
- NGKOMQXOGMMMDI-UHFFFAOYSA-N 3-(2-bromophenyl)-4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 NGKOMQXOGMMMDI-UHFFFAOYSA-N 0.000 claims 1
- DUGZVFHBSSQHDR-UHFFFAOYSA-N 3-(2-bromophenyl)-4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC=C(OC)C=C1 DUGZVFHBSSQHDR-UHFFFAOYSA-N 0.000 claims 1
- GEZSCPVDYAUXGS-UHFFFAOYSA-N 3-(2-bromophenyl)-4-ethyl-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 GEZSCPVDYAUXGS-UHFFFAOYSA-N 0.000 claims 1
- UBQQVQBPMGUXRO-UHFFFAOYSA-N 3-(2-bromophenyl)-4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O UBQQVQBPMGUXRO-UHFFFAOYSA-N 0.000 claims 1
- NBHVEICNYXNJOF-UHFFFAOYSA-N 3-(2-bromophenyl)-4-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 NBHVEICNYXNJOF-UHFFFAOYSA-N 0.000 claims 1
- YEHRMYOEQVKBRI-UHFFFAOYSA-N 3-(2-bromophenyl)-4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 YEHRMYOEQVKBRI-UHFFFAOYSA-N 0.000 claims 1
- VARJRQAJBOVJFZ-UHFFFAOYSA-N 3-(2-bromophenyl)-5-(cyclohexylmethylsulfanyl)-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1CCCCC1 VARJRQAJBOVJFZ-UHFFFAOYSA-N 0.000 claims 1
- FHFRKPQUXFCTNG-UHFFFAOYSA-N 3-(2-bromophenyl)-5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl FHFRKPQUXFCTNG-UHFFFAOYSA-N 0.000 claims 1
- JUJJGFAJRCMMPX-UHFFFAOYSA-N 3-(2-bromophenyl)-5-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC=CC=C1Cl JUJJGFAJRCMMPX-UHFFFAOYSA-N 0.000 claims 1
- WODFFZGITLJNLS-UHFFFAOYSA-N 3-(2-bromophenyl)-5-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 WODFFZGITLJNLS-UHFFFAOYSA-N 0.000 claims 1
- NCRIPJHEVGSKLF-UHFFFAOYSA-N 3-(2-bromophenyl)-5-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 NCRIPJHEVGSKLF-UHFFFAOYSA-N 0.000 claims 1
- WMLGOGGIJXEBLQ-UHFFFAOYSA-N 3-(2-bromophenyl)-5-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound CCN1C(SCC=2C(=CC=3OCOC=3C=2)Cl)=NN=C1C1=CC=CC=C1Br WMLGOGGIJXEBLQ-UHFFFAOYSA-N 0.000 claims 1
- QEDDHWCZOMHEJN-UHFFFAOYSA-N 3-(2-carbazol-9-ylethyl)-4-(2-methylprop-2-enyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(=C)C)C(CCN2C3=CC=CC=C3C3=CC=CC=C32)=N1 QEDDHWCZOMHEJN-UHFFFAOYSA-N 0.000 claims 1
- SEGJYUDMAPFJDH-UHFFFAOYSA-N 3-(2-carbazol-9-ylethyl)-4-prop-2-enyl-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC=C)C(CCN2C3=CC=CC=C3C3=CC=CC=C32)=N1 SEGJYUDMAPFJDH-UHFFFAOYSA-N 0.000 claims 1
- GWQHAEYSRALLID-UHFFFAOYSA-N 3-(2-chlorophenyl)-6,6-dimethyl-5,7-dihydro-1h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound N12CC(C)(C)CNC2=NN=C1C1=CC=CC=C1Cl GWQHAEYSRALLID-UHFFFAOYSA-N 0.000 claims 1
- GKWMIVQJQWDXQZ-UHFFFAOYSA-N 3-(2-chlorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound ClC1=CC=CC=C1C1=NN=C2N1CCCCC2 GKWMIVQJQWDXQZ-UHFFFAOYSA-N 0.000 claims 1
- QINSYGOHQYKFPF-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-cyclohexyl-n-methylprop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C=CC(=O)N(C)C1CCCCC1 QINSYGOHQYKFPF-UHFFFAOYSA-N 0.000 claims 1
- WIDYZQDJTCZHEP-UHFFFAOYSA-N 3-(2-fluorophenyl)-4-methyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1CSC(N1C)=NN=C1C1=CC=CC=C1F WIDYZQDJTCZHEP-UHFFFAOYSA-N 0.000 claims 1
- NVFDSULLRHMJQU-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-(4-methoxyphenoxy)-[1,2,4]triazolo[4,3-c]quinazoline Chemical compound C1=CC(OC)=CC=C1OC(N12)=NC3=CC=CC=C3C2=NN=C1C1=CC=CC=C1F NVFDSULLRHMJQU-UHFFFAOYSA-N 0.000 claims 1
- HIEGDBRJAYGLNK-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-[(4-fluorophenyl)methylsulfanyl]-4-methyl-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)F)N(C)C=1SCC1=CC=C(F)C=C1 HIEGDBRJAYGLNK-UHFFFAOYSA-N 0.000 claims 1
- HGKDAPBOUPXJKC-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-1,3-di(piperidin-1-yl)propan-1-one Chemical compound OC1=CC=CC=C1C(N1CCCCC1)CC(=O)N1CCCCC1 HGKDAPBOUPXJKC-UHFFFAOYSA-N 0.000 claims 1
- DXLSNMWLJNIWCG-UHFFFAOYSA-N 3-(2-methoxyethylsulfanyl)-4-(3-methoxypropyl)-5-thiophen-2-yl-1,2,4-triazole Chemical compound COCCCN1C(SCCOC)=NN=C1C1=CC=CS1 DXLSNMWLJNIWCG-UHFFFAOYSA-N 0.000 claims 1
- NBQVVFPOWJXAKT-UHFFFAOYSA-N 3-(2-methoxyethylsulfanyl)-5-(2-methoxyphenyl)-4-(3-methoxypropyl)-1,2,4-triazole Chemical compound COCCCN1C(SCCOC)=NN=C1C1=CC=CC=C1OC NBQVVFPOWJXAKT-UHFFFAOYSA-N 0.000 claims 1
- AFRGNIDHOWKOTB-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NN=C2N1CCCCC2 AFRGNIDHOWKOTB-UHFFFAOYSA-N 0.000 claims 1
- PREGFDQQYHBIGQ-UHFFFAOYSA-N 3-(3,4-dihydro-2h-quinoline-1-carbonyl)-n-phenylbenzenesulfonamide Chemical compound C1CCC2=CC=CC=C2N1C(=O)C(C=1)=CC=CC=1S(=O)(=O)NC1=CC=CC=C1 PREGFDQQYHBIGQ-UHFFFAOYSA-N 0.000 claims 1
- NZYZRDCUROHPJS-UHFFFAOYSA-N 3-(3-bromophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound BrC1=CC=CC(C=2N3CCCCCC3=NN=2)=C1 NZYZRDCUROHPJS-UHFFFAOYSA-N 0.000 claims 1
- DKSBFJYPICUHGY-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O DKSBFJYPICUHGY-UHFFFAOYSA-N 0.000 claims 1
- KHOKJXYLHXIULU-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 KHOKJXYLHXIULU-UHFFFAOYSA-N 0.000 claims 1
- OEAWYODXCQXBKI-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=C(C)C=C1 OEAWYODXCQXBKI-UHFFFAOYSA-N 0.000 claims 1
- XXZQXUMKRCUIJL-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O XXZQXUMKRCUIJL-UHFFFAOYSA-N 0.000 claims 1
- LVQHDRPKPCOZHW-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 LVQHDRPKPCOZHW-UHFFFAOYSA-N 0.000 claims 1
- RGDYXWNGNRWOKY-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 RGDYXWNGNRWOKY-UHFFFAOYSA-N 0.000 claims 1
- NHYZBLDZJVEMDA-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 NHYZBLDZJVEMDA-UHFFFAOYSA-N 0.000 claims 1
- KNACMFWQZAPIJJ-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-5-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl KNACMFWQZAPIJJ-UHFFFAOYSA-N 0.000 claims 1
- DXSYANUFWLNTRO-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-5-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=CC=C1Cl DXSYANUFWLNTRO-UHFFFAOYSA-N 0.000 claims 1
- SFLBLJRLLAMZIO-UHFFFAOYSA-N 3-(3-chloro-4-methylthiophen-2-yl)-5-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 SFLBLJRLLAMZIO-UHFFFAOYSA-N 0.000 claims 1
- WPVJPFLNVCGFQS-UHFFFAOYSA-N 3-(3-chlorophenyl)-4-prop-2-enyl-1h-1,2,4-triazole-5-thione Chemical compound ClC1=CC=CC(C=2N(C(=S)NN=2)CC=C)=C1 WPVJPFLNVCGFQS-UHFFFAOYSA-N 0.000 claims 1
- DYOWYUZNXBKQOK-UHFFFAOYSA-N 3-(3-chlorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound ClC1=CC=CC(C=2N3CCCCCC3=NN=2)=C1 DYOWYUZNXBKQOK-UHFFFAOYSA-N 0.000 claims 1
- PUBFRHXTIKNIPW-UHFFFAOYSA-N 3-(3-methyl-2-nitrophenyl)-4-(2-methylprop-2-enyl)-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(CC(=C)C)C(C=2C(=C(C)C=CC=2)[N+]([O-])=O)=N1 PUBFRHXTIKNIPW-UHFFFAOYSA-N 0.000 claims 1
- AGGUEVUAPLNPMU-UHFFFAOYSA-N 3-(3-methylphenyl)-4-prop-2-enyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=CC=CC(C=2N(C(=S)NN=2)CC=C)=C1 AGGUEVUAPLNPMU-UHFFFAOYSA-N 0.000 claims 1
- AMYLUVBFQNSLRI-UHFFFAOYSA-N 3-(4-bromophenyl)-5,5-dimethyl-6h-[1,2,4]triazolo[3,4-a]isoquinoline Chemical compound N12C(C)(C)CC3=CC=CC=C3C2=NN=C1C1=CC=C(Br)C=C1 AMYLUVBFQNSLRI-UHFFFAOYSA-N 0.000 claims 1
- ADECVMMOLHCQTO-UHFFFAOYSA-N 3-(4-bromophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound C1=CC(Br)=CC=C1C1=NN=C2N1CCCCC2 ADECVMMOLHCQTO-UHFFFAOYSA-N 0.000 claims 1
- DRIRVGMWCBVYST-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 DRIRVGMWCBVYST-UHFFFAOYSA-N 0.000 claims 1
- JLOLBXBPRLYBSL-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 JLOLBXBPRLYBSL-UHFFFAOYSA-N 0.000 claims 1
- APYGBEMLYNUVCI-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-ethyl-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 APYGBEMLYNUVCI-UHFFFAOYSA-N 0.000 claims 1
- TWCNQHCTOGUTRB-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O TWCNQHCTOGUTRB-UHFFFAOYSA-N 0.000 claims 1
- AJLJGWCTYZBDQA-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 AJLJGWCTYZBDQA-UHFFFAOYSA-N 0.000 claims 1
- PCJFDYFYSAOPMZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl PCJFDYFYSAOPMZ-UHFFFAOYSA-N 0.000 claims 1
- VYOHRIAPEJXCRD-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl VYOHRIAPEJXCRD-UHFFFAOYSA-N 0.000 claims 1
- TULXKOCSNDHOBC-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=CC=C1Cl TULXKOCSNDHOBC-UHFFFAOYSA-N 0.000 claims 1
- ACPDCMHBCLKTOE-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 ACPDCMHBCLKTOE-UHFFFAOYSA-N 0.000 claims 1
- PHGMTQJBXXFRJO-UHFFFAOYSA-N 3-(4-chlorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound C1=CC(Cl)=CC=C1C1=NN=C2N1CCCCC2 PHGMTQJBXXFRJO-UHFFFAOYSA-N 0.000 claims 1
- HZHSTMOFYQBVPV-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-(4-phenylpiperidin-1-yl)but-2-en-1-one Chemical compound C=1C=C(F)C=CC=1C(C)=CC(=O)N(CC1)CCC1C1=CC=CC=C1 HZHSTMOFYQBVPV-UHFFFAOYSA-N 0.000 claims 1
- WYBSOKBHOSUTJC-UHFFFAOYSA-N 3-(4-methoxyphenyl)-4-(2-methylprop-2-enyl)-1h-1,2,4-triazole-5-thione Chemical compound C1=CC(OC)=CC=C1C1=NNC(=S)N1CC(C)=C WYBSOKBHOSUTJC-UHFFFAOYSA-N 0.000 claims 1
- LUGLLAHZGTUSAE-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5,5,8,9-tetramethyl-6h-[1,2,4]triazolo[3,4-a]isoquinoline Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1C(C)(C)CC1=CC(C)=C(C)C=C12 LUGLLAHZGTUSAE-UHFFFAOYSA-N 0.000 claims 1
- KXLBDDZCWXWYRL-UHFFFAOYSA-N 3-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1CCCCC2 KXLBDDZCWXWYRL-UHFFFAOYSA-N 0.000 claims 1
- MDGGRHZKMXXZRD-UHFFFAOYSA-N 3-(4-methylphenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound C1=CC(C)=CC=C1C1=NN=C2N1CCCCC2 MDGGRHZKMXXZRD-UHFFFAOYSA-N 0.000 claims 1
- FTYKJOBQOANJJP-UHFFFAOYSA-N 3-(4-methylphenyl)-n-propan-2-yladamantane-1-carboxamide Chemical compound C1C(C(=O)NC(C)C)(C2)CC(C3)CC1CC32C1=CC=C(C)C=C1 FTYKJOBQOANJJP-UHFFFAOYSA-N 0.000 claims 1
- MVXLFZJXAAYQJJ-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-5-[(2,6-dichlorophenyl)methylsulfanyl]-4-(furan-2-ylmethyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1CC=2OC=CC=2)=NN=C1SCC1=C(Cl)C=CC=C1Cl MVXLFZJXAAYQJJ-UHFFFAOYSA-N 0.000 claims 1
- OUNBBIYHRZELDA-UHFFFAOYSA-N 3-(5,5-dimethyl-6h-[1,2,4]triazolo[3,4-a]isoquinolin-3-yl)phenol Chemical compound N12C(C)(C)CC3=CC=CC=C3C2=NN=C1C1=CC=CC(O)=C1 OUNBBIYHRZELDA-UHFFFAOYSA-N 0.000 claims 1
- YGTVDHWYOZPHMY-UHFFFAOYSA-N 3-(5-benzylsulfanyl-4-ethyl-1,2,4-triazol-3-yl)-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=CC=C1 YGTVDHWYOZPHMY-UHFFFAOYSA-N 0.000 claims 1
- VPHVTDGUKROOHL-UHFFFAOYSA-N 3-(5-benzylsulfanyl-4-ethyl-1,2,4-triazol-3-yl)pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=CC=C1 VPHVTDGUKROOHL-UHFFFAOYSA-N 0.000 claims 1
- OBSJSIGVRWBCFL-UHFFFAOYSA-N 3-(5-benzylsulfanyl-4-methyl-1,2,4-triazol-3-yl)-2,7-dimethylimidazo[1,2-a]pyridine Chemical compound CC=1N=C2C=C(C)C=CN2C=1C(N1C)=NN=C1SCC1=CC=CC=C1 OBSJSIGVRWBCFL-UHFFFAOYSA-N 0.000 claims 1
- HJNOSFFVUAXXSY-UHFFFAOYSA-N 3-(5-benzylsulfanyl-4-methyl-1,2,4-triazol-3-yl)-2-methylimidazo[1,2-a]pyridine Chemical compound CC=1N=C2C=CC=CN2C=1C(N1C)=NN=C1SCC1=CC=CC=C1 HJNOSFFVUAXXSY-UHFFFAOYSA-N 0.000 claims 1
- MMSKOIQDXOUXSX-UHFFFAOYSA-N 3-(5-bromopyridin-3-yl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound BrC1=CN=CC(C=2N3CCCCCC3=NN=2)=C1 MMSKOIQDXOUXSX-UHFFFAOYSA-N 0.000 claims 1
- YYCWXPFBQDRXTH-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O YYCWXPFBQDRXTH-UHFFFAOYSA-N 0.000 claims 1
- QBVWFWOUVGMAJC-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 QBVWFWOUVGMAJC-UHFFFAOYSA-N 0.000 claims 1
- CGKMIYPWIDPIEW-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 CGKMIYPWIDPIEW-UHFFFAOYSA-N 0.000 claims 1
- SRBQTOUPIGSLSD-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 SRBQTOUPIGSLSD-UHFFFAOYSA-N 0.000 claims 1
- JUMDBOWTNBNBAH-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O JUMDBOWTNBNBAH-UHFFFAOYSA-N 0.000 claims 1
- AGWZHLWCSRPPHL-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 AGWZHLWCSRPPHL-UHFFFAOYSA-N 0.000 claims 1
- KGEWKEKOCXUMHB-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-4-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 KGEWKEKOCXUMHB-UHFFFAOYSA-N 0.000 claims 1
- QJNOKMXOENBCAV-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 QJNOKMXOENBCAV-UHFFFAOYSA-N 0.000 claims 1
- DSTDGDBENPWUKI-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5-(cyclohexylmethylsulfanyl)-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1CCCCC1 DSTDGDBENPWUKI-UHFFFAOYSA-N 0.000 claims 1
- DEGHVHJRDUXQTB-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl DEGHVHJRDUXQTB-UHFFFAOYSA-N 0.000 claims 1
- MQNCKDQKNKRLCB-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl MQNCKDQKNKRLCB-UHFFFAOYSA-N 0.000 claims 1
- IZFUWGQEROOAMA-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 IZFUWGQEROOAMA-UHFFFAOYSA-N 0.000 claims 1
- UDKDUWDCNBRCHZ-UHFFFAOYSA-N 3-(5-hex-1-ynylpyridin-3-yl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound CCCCC#CC1=CN=CC(C=2N3CCCCCC3=NN=2)=C1 UDKDUWDCNBRCHZ-UHFFFAOYSA-N 0.000 claims 1
- JWZIWHICRPFTPD-UHFFFAOYSA-N 3-(6-chloropyridin-2-yl)oxy-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC(OC=2N=C(Cl)C=CC=2)=C1 JWZIWHICRPFTPD-UHFFFAOYSA-N 0.000 claims 1
- VJQYEVURLUHRTB-UHFFFAOYSA-N 3-(6-chloropyridin-3-yl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound C1=NC(Cl)=CC=C1C1=NN=C2N1CCCCC2 VJQYEVURLUHRTB-UHFFFAOYSA-N 0.000 claims 1
- MODAQROJTGKNOV-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1CCCCC1 MODAQROJTGKNOV-UHFFFAOYSA-N 0.000 claims 1
- HWFNQYPSZMBXGY-UHFFFAOYSA-N 3-(cyclohexylmethylsulfanyl)-4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1CCCCC1 HWFNQYPSZMBXGY-UHFFFAOYSA-N 0.000 claims 1
- AGFZJQDWVBDHHF-UHFFFAOYSA-N 3-(furan-2-yl)-5,5,8,9-tetramethyl-6h-[1,2,4]triazolo[3,4-a]isoquinoline Chemical compound N=1N=C2C=3C=C(C)C(C)=CC=3CC(C)(C)N2C=1C1=CC=CO1 AGFZJQDWVBDHHF-UHFFFAOYSA-N 0.000 claims 1
- SQTDQYVVYDFZBN-UHFFFAOYSA-N 3-(furan-2-yl)-5,5-dimethyl-6h-[1,2,4]triazolo[3,4-a]isoquinoline Chemical compound N12C(C)(C)CC3=CC=CC=C3C2=NN=C1C1=CC=CO1 SQTDQYVVYDFZBN-UHFFFAOYSA-N 0.000 claims 1
- BGFVNQHINQLFDX-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl BGFVNQHINQLFDX-UHFFFAOYSA-N 0.000 claims 1
- QERQFZYFMJSMCA-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl QERQFZYFMJSMCA-UHFFFAOYSA-N 0.000 claims 1
- UJIVCZXZMNVCFR-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl UJIVCZXZMNVCFR-UHFFFAOYSA-N 0.000 claims 1
- AJDRZYDXIDTOCN-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-5-naphthalen-1-yl-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl AJDRZYDXIDTOCN-UHFFFAOYSA-N 0.000 claims 1
- SAKNPYKNUYWQRS-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methylsulfanyl]-5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl SAKNPYKNUYWQRS-UHFFFAOYSA-N 0.000 claims 1
- LOJGCWANQZFGFB-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(2-methoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl LOJGCWANQZFGFB-UHFFFAOYSA-N 0.000 claims 1
- OEKRFTKYTLFADR-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl OEKRFTKYTLFADR-UHFFFAOYSA-N 0.000 claims 1
- YZXXYFLKJPWWHU-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl YZXXYFLKJPWWHU-UHFFFAOYSA-N 0.000 claims 1
- DITBEPNZCZFQCA-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl DITBEPNZCZFQCA-UHFFFAOYSA-N 0.000 claims 1
- XXZRCWAGJZZABV-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl XXZRCWAGJZZABV-UHFFFAOYSA-N 0.000 claims 1
- SVIHRIYPMJSUGY-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-5-naphthalen-1-yl-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl SVIHRIYPMJSUGY-UHFFFAOYSA-N 0.000 claims 1
- XBBJHCGKPFKHTM-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=C(Cl)C=CC=C1Cl XBBJHCGKPFKHTM-UHFFFAOYSA-N 0.000 claims 1
- IDKORPCVVKPQDI-UHFFFAOYSA-N 3-[(2-bromophenyl)methylsulfanyl]-4-methyl-5-(4-nitrophenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)[N+]([O-])=O)N(C)C=1SCC1=CC=CC=C1Br IDKORPCVVKPQDI-UHFFFAOYSA-N 0.000 claims 1
- IRYHRUBBGYXNIL-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-5-(2-methoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=CC=C1Cl IRYHRUBBGYXNIL-UHFFFAOYSA-N 0.000 claims 1
- COORSKCUQTXUFA-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=CC=C1Cl COORSKCUQTXUFA-UHFFFAOYSA-N 0.000 claims 1
- GAUAYWJNBPTGLG-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC=CC=C1Cl GAUAYWJNBPTGLG-UHFFFAOYSA-N 0.000 claims 1
- ZSICKQQNKZOXBJ-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 ZSICKQQNKZOXBJ-UHFFFAOYSA-N 0.000 claims 1
- LUOKHYJDRWQRRY-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 LUOKHYJDRWQRRY-UHFFFAOYSA-N 0.000 claims 1
- AQXZWGFZOLXGNA-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 AQXZWGFZOLXGNA-UHFFFAOYSA-N 0.000 claims 1
- XKSAONHUJOUUDX-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 XKSAONHUJOUUDX-UHFFFAOYSA-N 0.000 claims 1
- IHDCPKXRIKICLN-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methylsulfanyl]-5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 IHDCPKXRIKICLN-UHFFFAOYSA-N 0.000 claims 1
- ZJSXIHSBVFDSER-UHFFFAOYSA-N 3-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-5-(2-methoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 ZJSXIHSBVFDSER-UHFFFAOYSA-N 0.000 claims 1
- PMKANHCXMHJNHL-UHFFFAOYSA-N 3-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 PMKANHCXMHJNHL-UHFFFAOYSA-N 0.000 claims 1
- ODWAPLZHNWQTNS-UHFFFAOYSA-N 3-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 ODWAPLZHNWQTNS-UHFFFAOYSA-N 0.000 claims 1
- KMZZIBWYKJTLCK-UHFFFAOYSA-N 3-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 KMZZIBWYKJTLCK-UHFFFAOYSA-N 0.000 claims 1
- MYUAHKWKJFPTEA-UHFFFAOYSA-N 3-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 MYUAHKWKJFPTEA-UHFFFAOYSA-N 0.000 claims 1
- FEJSQOZDTHOEPJ-UHFFFAOYSA-N 3-[(3,5-dimethoxyphenyl)methylsulfanyl]-5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 FEJSQOZDTHOEPJ-UHFFFAOYSA-N 0.000 claims 1
- FLUACYKOEXGOCO-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methylsulfanyl]-4-methyl-5-thiophen-2-yl-1,2,4-triazole Chemical compound COC1=CC=CC(CSC=2N(C(C=3SC=CC=3)=NN=2)C)=C1 FLUACYKOEXGOCO-UHFFFAOYSA-N 0.000 claims 1
- WZFWCZCJXWJYTD-UHFFFAOYSA-N 3-[(4-bromophenyl)methylsulfanyl]-4-ethyl-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=C(Br)C=C1 WZFWCZCJXWJYTD-UHFFFAOYSA-N 0.000 claims 1
- IOKZATWVPBLTGG-UHFFFAOYSA-N 3-[(4-bromophenyl)methylsulfanyl]-4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=C(Br)C=C1 IOKZATWVPBLTGG-UHFFFAOYSA-N 0.000 claims 1
- TVUKXMVXBQEEDL-UHFFFAOYSA-N 3-[(4-bromophenyl)methylsulfanyl]-4-ethyl-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C(Br)C=C1 TVUKXMVXBQEEDL-UHFFFAOYSA-N 0.000 claims 1
- HGEFRRPCYFAVNP-UHFFFAOYSA-N 3-[(4-bromophenyl)methylsulfanyl]-5-(5-chlorothiophen-2-yl)-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(Br)C=C1 HGEFRRPCYFAVNP-UHFFFAOYSA-N 0.000 claims 1
- XWQFBDANJFMJGA-UHFFFAOYSA-N 3-[(4-chlorophenyl)methylsulfanyl]-4-ethyl-5-(4-nitrophenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)[N+]([O-])=O)N(CC)C=1SCC1=CC=C(Cl)C=C1 XWQFBDANJFMJGA-UHFFFAOYSA-N 0.000 claims 1
- PTBOVXACVWXRBG-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-4-methyl-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC1=CC=C(F)C=C1 PTBOVXACVWXRBG-UHFFFAOYSA-N 0.000 claims 1
- NPABVKBKBFUMHA-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methylsulfanyl]-4-methyl-5-phenyl-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1CSC(N1C)=NN=C1C1=CC=CC=C1 NPABVKBKBFUMHA-UHFFFAOYSA-N 0.000 claims 1
- LBBOQIQYPQBDHO-UHFFFAOYSA-N 3-[(4-tert-butylphenyl)methylsulfanyl]-4-methyl-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(C)C=1SCC1=CC=C(C(C)(C)C)C=C1 LBBOQIQYPQBDHO-UHFFFAOYSA-N 0.000 claims 1
- CJZFSHKTPZNMBF-UHFFFAOYSA-N 3-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-5-(2-methoxyphenyl)-1,2,4-triazole Chemical compound CCN1C(SCC=2C(=CC=3OCOC=3C=2)Cl)=NN=C1C1=CC=CC=C1OC CJZFSHKTPZNMBF-UHFFFAOYSA-N 0.000 claims 1
- CWBMMSLNAYLRPT-UHFFFAOYSA-N 3-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound CCN1C(SCC=2C(=CC=3OCOC=3C=2)Cl)=NN=C1C1=CC=CC=C1OC1=CC=CC=C1 CWBMMSLNAYLRPT-UHFFFAOYSA-N 0.000 claims 1
- NJRAIMZHLZAZJT-UHFFFAOYSA-N 3-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazole Chemical compound CCN1C(SCC=2C(=CC=3OCOC=3C=2)Cl)=NN=C1C1=CC=C(OC)C=C1 NJRAIMZHLZAZJT-UHFFFAOYSA-N 0.000 claims 1
- SFQFCEXIVZTHGU-UHFFFAOYSA-N 3-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound CCN1C(SCC=2C(=CC=3OCOC=3C=2)Cl)=NN=C1C1=CC=C(C)S1 SFQFCEXIVZTHGU-UHFFFAOYSA-N 0.000 claims 1
- UDPBMSXXHPBWDF-UHFFFAOYSA-N 3-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound CCN1C(SCC=2C(=CC=3OCOC=3C=2)Cl)=NN=C1C(=C1C(F)(F)F)C=NN1C1=CC=CC=C1 UDPBMSXXHPBWDF-UHFFFAOYSA-N 0.000 claims 1
- CUIUQAMNEKABRY-UHFFFAOYSA-N 3-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-4-ethyl-5-thiophen-2-yl-1,2,4-triazole Chemical compound CCN1C(SCC=2C(=CC=3OCOC=3C=2)Cl)=NN=C1C1=CC=CS1 CUIUQAMNEKABRY-UHFFFAOYSA-N 0.000 claims 1
- KVFIPBBQJARLOV-UHFFFAOYSA-N 3-[(6-chloro-1,3-benzodioxol-5-yl)methylsulfanyl]-5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-1,2,4-triazole Chemical compound CCN1C(SCC=2C(=CC=3OCOC=3C=2)Cl)=NN=C1C(C=C1)=CC=C1N1C(C)=CC=C1C KVFIPBBQJARLOV-UHFFFAOYSA-N 0.000 claims 1
- AESWMSCLVNNIQD-UHFFFAOYSA-N 3-[1-(1h-indole-5-carbonyl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1=C2NC=CC2=CC(C(N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)=O)=C1 AESWMSCLVNNIQD-UHFFFAOYSA-N 0.000 claims 1
- RAWVSRAIUPFWKY-UHFFFAOYSA-N 3-[1-(3-cyclohexylpropanoyl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1C(=O)CCC1CCCCC1 RAWVSRAIUPFWKY-UHFFFAOYSA-N 0.000 claims 1
- VIXSEPGMXMZCNJ-UHFFFAOYSA-N 3-[1-(6-phenylhexanoyl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1C(=O)CCCCCC1=CC=CC=C1 VIXSEPGMXMZCNJ-UHFFFAOYSA-N 0.000 claims 1
- KYKSBULMCOJGHZ-UHFFFAOYSA-N 3-[2-(1,3-dioxoisoindol-2-yl)ethyl]adamantane-1-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC1(C2)CC(C3)CC2CC3(C(=O)O)C1 KYKSBULMCOJGHZ-UHFFFAOYSA-N 0.000 claims 1
- IWUWWHBHHKXIDC-UHFFFAOYSA-N 3-[2-(phenylmethoxymethyl)phenyl]-2,4,5-triazatricyclo[5.3.1.02,6]undeca-3,5-diene Chemical compound C=1C=CC=C(C=2N3C4CC(CCC4)C3=NN=2)C=1COCC1=CC=CC=C1 IWUWWHBHHKXIDC-UHFFFAOYSA-N 0.000 claims 1
- CKHBZLXXKPRRNV-UHFFFAOYSA-N 3-[3-(4-ethoxyphenyl)-7-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbaldehyde Chemical compound C1=CC(OCC)=CC=C1C1=C2N=CC=C(C)N2N=C1C1CN(C=O)CCC1 CKHBZLXXKPRRNV-UHFFFAOYSA-N 0.000 claims 1
- UJJSZCSLQQMCEA-UHFFFAOYSA-N 3-[3-[(2,4-dichlorophenyl)methoxy]thiophen-2-yl]-4-methyl-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(C)C(C2=C(C=CS2)OCC=2C(=CC(Cl)=CC=2)Cl)=N1 UJJSZCSLQQMCEA-UHFFFAOYSA-N 0.000 claims 1
- FWYLPZHZJQXRCC-UHFFFAOYSA-N 3-[3-[(2,4-dichlorophenyl)methoxy]thiophen-2-yl]-4-methyl-5-methylsulfanyl-1,2,4-triazole Chemical compound CN1C(SC)=NN=C1C1=C(OCC=2C(=CC(Cl)=CC=2)Cl)C=CS1 FWYLPZHZJQXRCC-UHFFFAOYSA-N 0.000 claims 1
- OMGQRBXCEOHLIC-UHFFFAOYSA-N 3-[4-(2,3-dimethylphenyl)piperazine-1-carbonyl]isochromen-1-one Chemical compound CC1=CC=CC(N2CCN(CC2)C(=O)C=2OC(=O)C3=CC=CC=C3C=2)=C1C OMGQRBXCEOHLIC-UHFFFAOYSA-N 0.000 claims 1
- WUKSKSMKGWHRNF-UHFFFAOYSA-N 3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O WUKSKSMKGWHRNF-UHFFFAOYSA-N 0.000 claims 1
- RDMZQNGHMYNXHB-UHFFFAOYSA-N 3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 RDMZQNGHMYNXHB-UHFFFAOYSA-N 0.000 claims 1
- FGBONUAUMBDMJP-UHFFFAOYSA-N 3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C(OC)C=C1 FGBONUAUMBDMJP-UHFFFAOYSA-N 0.000 claims 1
- RYPBPPUWFCBFPP-UHFFFAOYSA-N 3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 RYPBPPUWFCBFPP-UHFFFAOYSA-N 0.000 claims 1
- YEBXQSPQBBWMHD-UHFFFAOYSA-N 3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-5-[(4-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 YEBXQSPQBBWMHD-UHFFFAOYSA-N 0.000 claims 1
- HNJLAXQOGWIJNY-UHFFFAOYSA-N 3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O HNJLAXQOGWIJNY-UHFFFAOYSA-N 0.000 claims 1
- UZYKFACDGDQGID-UHFFFAOYSA-N 3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 UZYKFACDGDQGID-UHFFFAOYSA-N 0.000 claims 1
- IQZQPIQRXJBMNP-UHFFFAOYSA-N 3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 IQZQPIQRXJBMNP-UHFFFAOYSA-N 0.000 claims 1
- KYQYKLYWKGVGAP-UHFFFAOYSA-N 3-[4-(2-ethoxyphenyl)piperazine-1-carbonyl]isochromen-1-one Chemical compound CCOC1=CC=CC=C1N1CCN(C(=O)C=2OC(=O)C3=CC=CC=C3C=2)CC1 KYQYKLYWKGVGAP-UHFFFAOYSA-N 0.000 claims 1
- JPKCHGNOMVKVFU-UHFFFAOYSA-N 3-[4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O JPKCHGNOMVKVFU-UHFFFAOYSA-N 0.000 claims 1
- AXLZXXSFCOIMNB-UHFFFAOYSA-N 3-[4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1=CC=CC=C1[N+]([O-])=O AXLZXXSFCOIMNB-UHFFFAOYSA-N 0.000 claims 1
- FCLJMOCSQSZVBA-UHFFFAOYSA-N 3-[4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O FCLJMOCSQSZVBA-UHFFFAOYSA-N 0.000 claims 1
- NMXDDCIDHCFWOV-UHFFFAOYSA-N 3-[4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1=CC=CC([N+]([O-])=O)=C1 NMXDDCIDHCFWOV-UHFFFAOYSA-N 0.000 claims 1
- RKSOGEXMQNGICA-UHFFFAOYSA-N 3-[4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 RKSOGEXMQNGICA-UHFFFAOYSA-N 0.000 claims 1
- UPHYKYARZIXRIB-UHFFFAOYSA-N 3-[4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 UPHYKYARZIXRIB-UHFFFAOYSA-N 0.000 claims 1
- HXZYKKYLHOJMQK-UHFFFAOYSA-N 3-[4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=C(C)C=C1 HXZYKKYLHOJMQK-UHFFFAOYSA-N 0.000 claims 1
- HXNVXTNSOQDIAV-UHFFFAOYSA-N 3-[4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 HXNVXTNSOQDIAV-UHFFFAOYSA-N 0.000 claims 1
- DABBXGIEQXBRBS-UHFFFAOYSA-N 3-[4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 DABBXGIEQXBRBS-UHFFFAOYSA-N 0.000 claims 1
- NLABIGWVHQVUNX-UHFFFAOYSA-N 3-[4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1=CC=C(S(C)(=O)=O)C=C1 NLABIGWVHQVUNX-UHFFFAOYSA-N 0.000 claims 1
- BLXHHWJLQHRCRE-UHFFFAOYSA-N 3-[4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 BLXHHWJLQHRCRE-UHFFFAOYSA-N 0.000 claims 1
- QOOSBVXUMBBSIM-UHFFFAOYSA-N 3-[4-ethyl-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 QOOSBVXUMBBSIM-UHFFFAOYSA-N 0.000 claims 1
- JPMQUJRZAOCXCM-UHFFFAOYSA-N 3-[4-ethyl-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 JPMQUJRZAOCXCM-UHFFFAOYSA-N 0.000 claims 1
- KBHMOSDOPCSSSJ-UHFFFAOYSA-N 3-[4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O KBHMOSDOPCSSSJ-UHFFFAOYSA-N 0.000 claims 1
- XNEUNIPTDIKTHX-UHFFFAOYSA-N 3-[4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1=CC(C)=CC=C1[N+]([O-])=O XNEUNIPTDIKTHX-UHFFFAOYSA-N 0.000 claims 1
- DKXLSAPVUXSUPS-UHFFFAOYSA-N 3-[4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O DKXLSAPVUXSUPS-UHFFFAOYSA-N 0.000 claims 1
- PWTPVTAMRQRLLE-UHFFFAOYSA-N 3-[4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 PWTPVTAMRQRLLE-UHFFFAOYSA-N 0.000 claims 1
- MUUMKPOBYXXBQQ-UHFFFAOYSA-N 3-[4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1=CC=CC(OC(F)(F)F)=C1 MUUMKPOBYXXBQQ-UHFFFAOYSA-N 0.000 claims 1
- INXKOPLFUHPDKT-UHFFFAOYSA-N 3-[4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 INXKOPLFUHPDKT-UHFFFAOYSA-N 0.000 claims 1
- LIQKCJGUBVDPRD-UHFFFAOYSA-N 3-[4-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 LIQKCJGUBVDPRD-UHFFFAOYSA-N 0.000 claims 1
- SRNOJCSARXWTAT-UHFFFAOYSA-N 3-[4-ethyl-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 SRNOJCSARXWTAT-UHFFFAOYSA-N 0.000 claims 1
- JXHVHSWQECWVRF-UHFFFAOYSA-N 3-[4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 JXHVHSWQECWVRF-UHFFFAOYSA-N 0.000 claims 1
- NNFOYWRVDVJJKX-UHFFFAOYSA-N 3-[4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1=CC=C(C(F)(F)F)C=C1 NNFOYWRVDVJJKX-UHFFFAOYSA-N 0.000 claims 1
- LTPRKFGJHMENLP-UHFFFAOYSA-N 3-[4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 LTPRKFGJHMENLP-UHFFFAOYSA-N 0.000 claims 1
- PGZCWMRBISUIIZ-UHFFFAOYSA-N 3-[5-(cyclohexylmethylsulfanyl)-4-ethyl-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1CCCCC1 PGZCWMRBISUIIZ-UHFFFAOYSA-N 0.000 claims 1
- RNFVTUFEPVBIQP-UHFFFAOYSA-N 3-[5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl RNFVTUFEPVBIQP-UHFFFAOYSA-N 0.000 claims 1
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- ZUDRZNYQBNGXPM-UHFFFAOYSA-N 3-[5-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1=CC=CC=C1Cl ZUDRZNYQBNGXPM-UHFFFAOYSA-N 0.000 claims 1
- YCRQXBFFTSUFSD-UHFFFAOYSA-N 3-[5-[(2-chlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=CC=C1Cl YCRQXBFFTSUFSD-UHFFFAOYSA-N 0.000 claims 1
- ZTFNZLSGIUNRPY-UHFFFAOYSA-N 3-[5-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]-2-methylsulfanylpyridine Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 ZTFNZLSGIUNRPY-UHFFFAOYSA-N 0.000 claims 1
- DPBJNGLWHONYCE-UHFFFAOYSA-N 3-[5-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]propan-1-ol Chemical compound CCN1C(CCCO)=NN=C1SCC1=CC=C(Cl)C(Cl)=C1 DPBJNGLWHONYCE-UHFFFAOYSA-N 0.000 claims 1
- LASUOURWKYTOJW-UHFFFAOYSA-N 3-[5-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=C(Cl)C(Cl)=C1 LASUOURWKYTOJW-UHFFFAOYSA-N 0.000 claims 1
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- KXLMJGGWGIGLQZ-UHFFFAOYSA-N 3-[[4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]methyl]-1h-indole Chemical compound CCN1C(CC=2C3=CC=CC=C3NC=2)=NN=C1SCC1=CC=CC(OC(F)(F)F)=C1 KXLMJGGWGIGLQZ-UHFFFAOYSA-N 0.000 claims 1
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- XMZOCSCCWOIESM-UHFFFAOYSA-N 3-[[5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]methyl]-1h-indole Chemical compound CCN1C(CC=2C3=CC=CC=C3NC=2)=NN=C1SCC1=CC=C(Cl)C=C1Cl XMZOCSCCWOIESM-UHFFFAOYSA-N 0.000 claims 1
- JWAKVDYLOYTRAI-UHFFFAOYSA-N 3-[[5-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]methyl]-1h-indole Chemical compound CCN1C(CC=2C3=CC=CC=C3NC=2)=NN=C1SCC1=C(Cl)C=CC=C1Cl JWAKVDYLOYTRAI-UHFFFAOYSA-N 0.000 claims 1
- IYQNQRHORBZDKL-UHFFFAOYSA-N 3-[[5-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]methyl]-1h-indole Chemical compound CCN1C(CC=2C3=CC=CC=C3NC=2)=NN=C1SCC1=CC=C(Cl)C(Cl)=C1 IYQNQRHORBZDKL-UHFFFAOYSA-N 0.000 claims 1
- LAFGXKLOHXWNCS-UHFFFAOYSA-N 3-[[5-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]methyl]-1h-indole Chemical compound CCN1C(CC=2C3=CC=CC=C3NC=2)=NN=C1SCC1=CC(OC)=CC(OC)=C1 LAFGXKLOHXWNCS-UHFFFAOYSA-N 0.000 claims 1
- QSSZFEXITQOVAN-UHFFFAOYSA-N 3-amino-n-cyclohexyl-n-methylbenzamide Chemical compound C=1C=CC(N)=CC=1C(=O)N(C)C1CCCCC1 QSSZFEXITQOVAN-UHFFFAOYSA-N 0.000 claims 1
- DFDCVQAGGAQLPM-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl(1h-imidazol-5-yl)methanone Chemical compound C1C(CC2)CCC2CN1C(=O)C1=CNC=N1 DFDCVQAGGAQLPM-UHFFFAOYSA-N 0.000 claims 1
- OMWOJLYJWCJZBS-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl(1h-indol-3-yl)methanone Chemical compound C1CC(C2)CCC1CN2C(=O)C1=CNC2=CC=CC=C12 OMWOJLYJWCJZBS-UHFFFAOYSA-N 0.000 claims 1
- CRQKCCXRMKLINA-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl(1h-indol-5-yl)methanone Chemical compound C1CC(C2)CCC1CN2C(=O)C1=CC=C(NC=C2)C2=C1 CRQKCCXRMKLINA-UHFFFAOYSA-N 0.000 claims 1
- UEOPWQUBKNHVMA-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl(quinolin-2-yl)methanone Chemical compound C1CC(C2)CCC1CN2C(=O)C1=CC=C(C=CC=C2)C2=N1 UEOPWQUBKNHVMA-UHFFFAOYSA-N 0.000 claims 1
- DNLQVIGADVTFPN-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl-(1-methylindol-3-yl)methanone Chemical compound C1CC(C2)CCC1CN2C(=O)C1=CN(C)C2=CC=CC=C21 DNLQVIGADVTFPN-UHFFFAOYSA-N 0.000 claims 1
- PFGGHCQDRUHGQF-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl-(2,4-dimethyl-1,3-thiazol-5-yl)methanone Chemical compound S1C(C)=NC(C)=C1C(=O)N1CC(CC2)CCC2C1 PFGGHCQDRUHGQF-UHFFFAOYSA-N 0.000 claims 1
- NXOVBRAJXCOONU-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl-(2-bromophenyl)methanone Chemical compound BrC1=CC=CC=C1C(=O)N1CC(CC2)CCC2C1 NXOVBRAJXCOONU-UHFFFAOYSA-N 0.000 claims 1
- NTLUMMHVTHLTLV-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl-(4-methyl-2-phenyl-1,3-thiazol-5-yl)methanone Chemical compound S1C(C(=O)N2CC3CCC(CC3)C2)=C(C)N=C1C1=CC=CC=C1 NTLUMMHVTHLTLV-UHFFFAOYSA-N 0.000 claims 1
- IOUVKGGHRRTOHA-UHFFFAOYSA-N 3-benzyl-4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(SCC=2C(=CC=CC=2)[N+]([O-])=O)N(CC)C=1CC1=CC=CC=C1 IOUVKGGHRRTOHA-UHFFFAOYSA-N 0.000 claims 1
- YETRWAVEVYCBJG-UHFFFAOYSA-N 3-benzyl-4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(SCC=2C=CC(OC)=CC=2)N(CC)C=1CC1=CC=CC=C1 YETRWAVEVYCBJG-UHFFFAOYSA-N 0.000 claims 1
- SPGKHGVGMWIKEH-UHFFFAOYSA-N 3-benzyl-4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(SCC=2C=CC(C)=CC=2)N(CC)C=1CC1=CC=CC=C1 SPGKHGVGMWIKEH-UHFFFAOYSA-N 0.000 claims 1
- DCMJNEXEPFHOJH-UHFFFAOYSA-N 3-benzyl-4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(SCC=2C(=CC=C(C)C=2)[N+]([O-])=O)N(CC)C=1CC1=CC=CC=C1 DCMJNEXEPFHOJH-UHFFFAOYSA-N 0.000 claims 1
- DOMVEPZAHSQDKM-UHFFFAOYSA-N 3-benzyl-4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(SCC=2C=CC(=CC=2)C(F)(F)F)N(CC)C=1CC1=CC=CC=C1 DOMVEPZAHSQDKM-UHFFFAOYSA-N 0.000 claims 1
- PSBSJXFQHPXRLP-UHFFFAOYSA-N 3-benzyl-5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(SCC=2C(=CC(Cl)=CC=2)Cl)N(CC)C=1CC1=CC=CC=C1 PSBSJXFQHPXRLP-UHFFFAOYSA-N 0.000 claims 1
- OQHBWSLNFUSMQP-UHFFFAOYSA-N 3-benzyl-5-[(2,6-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(SCC=2C(=CC=CC=2Cl)Cl)N(CC)C=1CC1=CC=CC=C1 OQHBWSLNFUSMQP-UHFFFAOYSA-N 0.000 claims 1
- DBFWVYFXFUDNRN-UHFFFAOYSA-N 3-benzyl-5-[(2-chloro-6-fluorophenyl)methylsulfanyl]-4-methyl-1,2,4-triazole Chemical compound N=1N=C(SCC=2C(=CC=CC=2F)Cl)N(C)C=1CC1=CC=CC=C1 DBFWVYFXFUDNRN-UHFFFAOYSA-N 0.000 claims 1
- DJSHOVRQEUVJFW-UHFFFAOYSA-N 3-benzyl-5-[(3,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(SCC=2C=C(Cl)C(Cl)=CC=2)N(CC)C=1CC1=CC=CC=C1 DJSHOVRQEUVJFW-UHFFFAOYSA-N 0.000 claims 1
- DQRONKYBFVOFDF-UHFFFAOYSA-N 3-benzyl-5-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-1,2,4-triazole Chemical compound N=1N=C(SCC=2C=C(OC)C=C(OC)C=2)N(CC)C=1CC1=CC=CC=C1 DQRONKYBFVOFDF-UHFFFAOYSA-N 0.000 claims 1
- HSQIYJMQYYYHJT-UHFFFAOYSA-N 3-benzyl-5-[(4-chlorophenyl)methylsulfanyl]-4-methyl-1,2,4-triazole Chemical compound N=1N=C(SCC=2C=CC(Cl)=CC=2)N(C)C=1CC1=CC=CC=C1 HSQIYJMQYYYHJT-UHFFFAOYSA-N 0.000 claims 1
- ZNTLWYFQGSFBOM-UHFFFAOYSA-N 3-benzyl-5-benzylsulfanyl-4-ethyl-1,2,4-triazole;4-[5-[(2-chloro-6-fluorophenyl)methylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(SCC=2C=CC=CC=2)N(CC)C=1CC1=CC=CC=C1.N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC1=C(F)C=CC=C1Cl ZNTLWYFQGSFBOM-UHFFFAOYSA-N 0.000 claims 1
- WYRSPYXQDGIYCX-UHFFFAOYSA-N 3-benzylsulfanyl-4-ethyl-5-(4-nitrophenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)[N+]([O-])=O)N(CC)C=1SCC1=CC=CC=C1 WYRSPYXQDGIYCX-UHFFFAOYSA-N 0.000 claims 1
- KMBWUQZURFUDPU-UHFFFAOYSA-N 3-benzylsulfanyl-4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=CC=C1 KMBWUQZURFUDPU-UHFFFAOYSA-N 0.000 claims 1
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- GJFQTEDCEPUYKK-UHFFFAOYSA-N 3-benzylsulfanyl-4-methyl-5-(3,4,5-trimethoxyphenyl)-1,2,4-triazole Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(SCC=3C=CC=CC=3)=NN=2)C)=C1 GJFQTEDCEPUYKK-UHFFFAOYSA-N 0.000 claims 1
- ICFSYQMPQQLGAZ-UHFFFAOYSA-N 3-benzylsulfanyl-5-(2-methoxyphenyl)-4-methyl-1,2,4-triazole Chemical compound COC1=CC=CC=C1C(N1C)=NN=C1SCC1=CC=CC=C1 ICFSYQMPQQLGAZ-UHFFFAOYSA-N 0.000 claims 1
- LRXYRGFVYAHAPZ-UHFFFAOYSA-N 3-benzylsulfanyl-5-(4-methoxyphenyl)-4-methyl-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C(N1C)=NN=C1SCC1=CC=CC=C1 LRXYRGFVYAHAPZ-UHFFFAOYSA-N 0.000 claims 1
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- TVCPFXRYXOOVCW-UHFFFAOYSA-N 3-bicyclo[2.2.1]heptanyl-[4-(2,3-dimethylphenyl)piperazin-1-yl]methanone Chemical compound CC1=CC=CC(N2CCN(CC2)C(=O)C2C3CCC(C3)C2)=C1C TVCPFXRYXOOVCW-UHFFFAOYSA-N 0.000 claims 1
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- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
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- CBLGYZSCFONDCM-UHFFFAOYSA-N 4-[4-[(4-ethyl-5-pyridin-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 CBLGYZSCFONDCM-UHFFFAOYSA-N 0.000 claims 1
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- GPDLQULFHHPNGY-UHFFFAOYSA-N 4-[4-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 GPDLQULFHHPNGY-UHFFFAOYSA-N 0.000 claims 1
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- GTNQPQNVLRLTCQ-UHFFFAOYSA-N 4-[4-[[4-ethyl-5-(2-phenoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 GTNQPQNVLRLTCQ-UHFFFAOYSA-N 0.000 claims 1
- KQDRKEZEXONQKL-UHFFFAOYSA-N 4-[4-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 KQDRKEZEXONQKL-UHFFFAOYSA-N 0.000 claims 1
- RTHARHUIYLMPDW-UHFFFAOYSA-N 4-[4-[[4-ethyl-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 RTHARHUIYLMPDW-UHFFFAOYSA-N 0.000 claims 1
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- BGBGYKQVRVOOJF-UHFFFAOYSA-N 4-[4-[[5-(1,3-benzodioxol-5-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 BGBGYKQVRVOOJF-UHFFFAOYSA-N 0.000 claims 1
- LFJYRICFGCWGLX-UHFFFAOYSA-N 4-[4-[[5-(1-benzothiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 LFJYRICFGCWGLX-UHFFFAOYSA-N 0.000 claims 1
- XCUPFZHLHYDCNX-UHFFFAOYSA-N 4-[4-[[5-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 XCUPFZHLHYDCNX-UHFFFAOYSA-N 0.000 claims 1
- BMMUAFBXVFHGPP-UHFFFAOYSA-N 4-[4-[[5-(4-chlorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 BMMUAFBXVFHGPP-UHFFFAOYSA-N 0.000 claims 1
- RYWLDCMGGNRWLC-UHFFFAOYSA-N 4-[4-[[5-(5-chlorothiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]thiadiazole Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC(C=C1)=CC=C1C1=CSN=N1 RYWLDCMGGNRWLC-UHFFFAOYSA-N 0.000 claims 1
- ATRROVFKDWDIKQ-UHFFFAOYSA-N 4-[4-ethyl-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O ATRROVFKDWDIKQ-UHFFFAOYSA-N 0.000 claims 1
- OUYCXSAGTHGGJJ-UHFFFAOYSA-N 4-[4-ethyl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 OUYCXSAGTHGGJJ-UHFFFAOYSA-N 0.000 claims 1
- MXRDZHAYTHVKIY-UHFFFAOYSA-N 4-[4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]-n,n-dimethylaniline Chemical compound N=1N=C(C=2C=CC(=CC=2)N(C)C)N(CC)C=1SCC1=CC=C(OC)C=C1 MXRDZHAYTHVKIY-UHFFFAOYSA-N 0.000 claims 1
- GLVAEIXDDKOVRD-UHFFFAOYSA-N 4-[4-ethyl-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 GLVAEIXDDKOVRD-UHFFFAOYSA-N 0.000 claims 1
- APUOSMIWAIFJBP-UHFFFAOYSA-N 4-[4-ethyl-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 APUOSMIWAIFJBP-UHFFFAOYSA-N 0.000 claims 1
- FZUQSOVFDFUGLN-UHFFFAOYSA-N 4-[4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 FZUQSOVFDFUGLN-UHFFFAOYSA-N 0.000 claims 1
- IOZSWHQHVPBNGE-UHFFFAOYSA-N 4-[4-ethyl-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 IOZSWHQHVPBNGE-UHFFFAOYSA-N 0.000 claims 1
- ONPJCEYLMNBNRD-UHFFFAOYSA-N 4-[4-ethyl-5-[(4-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]-n,n-dimethylaniline Chemical compound N=1N=C(C=2C=CC(=CC=2)N(C)C)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 ONPJCEYLMNBNRD-UHFFFAOYSA-N 0.000 claims 1
- PYUIMMDIINJDHK-UHFFFAOYSA-N 4-[4-ethyl-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 PYUIMMDIINJDHK-UHFFFAOYSA-N 0.000 claims 1
- VLMPNOBPFDZHGP-UHFFFAOYSA-N 4-[4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]-n,n-dimethylaniline Chemical compound N=1N=C(C=2C=CC(=CC=2)N(C)C)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O VLMPNOBPFDZHGP-UHFFFAOYSA-N 0.000 claims 1
- ZXIMFLGCCZZJPK-UHFFFAOYSA-N 4-[4-ethyl-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O ZXIMFLGCCZZJPK-UHFFFAOYSA-N 0.000 claims 1
- LCAHTRHNNGPQBQ-UHFFFAOYSA-N 4-[4-ethyl-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 LCAHTRHNNGPQBQ-UHFFFAOYSA-N 0.000 claims 1
- MZXMJRXLRDGTEK-UHFFFAOYSA-N 4-[4-ethyl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 MZXMJRXLRDGTEK-UHFFFAOYSA-N 0.000 claims 1
- QGMRICCOCAZISZ-UHFFFAOYSA-N 4-[5-(6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepin-3-yl)pyridin-2-yl]morpholine Chemical compound C1COCCN1C1=CC=C(C=2N3CCCCCC3=NN=2)C=N1 QGMRICCOCAZISZ-UHFFFAOYSA-N 0.000 claims 1
- IDNWCNHKUOMRRB-UHFFFAOYSA-N 4-[5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]-n,n-dimethylaniline Chemical compound N=1N=C(C=2C=CC(=CC=2)N(C)C)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl IDNWCNHKUOMRRB-UHFFFAOYSA-N 0.000 claims 1
- YMHASMKSPODPMT-UHFFFAOYSA-N 4-[5-[(2,4-dichlorophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC=C(Cl)C=C1Cl YMHASMKSPODPMT-UHFFFAOYSA-N 0.000 claims 1
- HLZVIUZAYFVDSA-UHFFFAOYSA-N 4-[5-[(2,6-dichlorophenyl)methylsulfanyl]-4-(furan-2-ylmethyl)-1,2,4-triazol-3-yl]pyridine Chemical compound ClC1=CC=CC(Cl)=C1CSC(N1CC=2OC=CC=2)=NN=C1C1=CC=NC=C1 HLZVIUZAYFVDSA-UHFFFAOYSA-N 0.000 claims 1
- ZHOYYBOHVOLBKW-UHFFFAOYSA-N 4-[5-[(3,5-dimethoxyphenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC1=CC(OC)=CC(OC)=C1 ZHOYYBOHVOLBKW-UHFFFAOYSA-N 0.000 claims 1
- KYXIMLKSQIMTGY-UHFFFAOYSA-N 4-[5-[(4-bromophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]phenol Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC=C(Br)C=C1 KYXIMLKSQIMTGY-UHFFFAOYSA-N 0.000 claims 1
- RLTJGWZANMGDJP-UHFFFAOYSA-N 4-[5-[(4-bromophenyl)methylsulfanyl]-4-ethyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC1=CC=C(Br)C=C1 RLTJGWZANMGDJP-UHFFFAOYSA-N 0.000 claims 1
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- OUFPCLUUQYRIQE-UHFFFAOYSA-N 4-[5-[(4-chlorophenyl)methylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]aniline Chemical compound N=1N=C(C=2C=CC(N)=CC=2)N(C)C=1SCC1=CC=C(Cl)C=C1 OUFPCLUUQYRIQE-UHFFFAOYSA-N 0.000 claims 1
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- SBBLEUVFEHJPGB-UHFFFAOYSA-N 4-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]benzonitrile Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=C(C#N)C=C1 SBBLEUVFEHJPGB-UHFFFAOYSA-N 0.000 claims 1
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- AZDXADGHORPDIT-UHFFFAOYSA-N 4-[[5-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzonitrile Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=C(C#N)C=C1 AZDXADGHORPDIT-UHFFFAOYSA-N 0.000 claims 1
- KRBJECGCLMEFFZ-UHFFFAOYSA-N 4-[[5-(4-chlorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzonitrile Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(C#N)C=C1 KRBJECGCLMEFFZ-UHFFFAOYSA-N 0.000 claims 1
- NSBMTWPTPAUAKE-UHFFFAOYSA-N 4-[[5-(5-chlorothiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzonitrile Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(C#N)C=C1 NSBMTWPTPAUAKE-UHFFFAOYSA-N 0.000 claims 1
- WWIXCWSAVMUZRS-UHFFFAOYSA-N 4-[[5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzonitrile Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C(C#N)C=C1 WWIXCWSAVMUZRS-UHFFFAOYSA-N 0.000 claims 1
- PFIOQDWZNYYLGN-UHFFFAOYSA-N 4-[benzyl(methylsulfonyl)amino]-n-(furan-2-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC=2OC=CC=2)C=CC=1N(S(=O)(=O)C)CC1=CC=CC=C1 PFIOQDWZNYYLGN-UHFFFAOYSA-N 0.000 claims 1
- NJPRATJHCGOAKI-UHFFFAOYSA-N 4-amino-n-(2,3-dihydro-1h-inden-2-yl)-n-[(3-hydroxyphenyl)methyl]-2-(propanoylamino)butanamide Chemical compound C1C2=CC=CC=C2CC1N(C(=O)C(CCN)NC(=O)CC)CC1=CC=CC(O)=C1 NJPRATJHCGOAKI-UHFFFAOYSA-N 0.000 claims 1
- VBQURISEJZGIJF-UHFFFAOYSA-N 4-amino-n-cyclohexyl-n-methylbenzamide Chemical compound C=1C=C(N)C=CC=1C(=O)N(C)C1CCCCC1 VBQURISEJZGIJF-UHFFFAOYSA-N 0.000 claims 1
- KSMOEHJKKPNNLU-UHFFFAOYSA-N 4-benzoyl-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 KSMOEHJKKPNNLU-UHFFFAOYSA-N 0.000 claims 1
- AUTMXVSOOABCRA-UHFFFAOYSA-N 4-benzyl-3,5-bis(4-methylphenyl)-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1C(N1CC=2C=CC=CC=2)=NN=C1C1=CC=C(C)C=C1 AUTMXVSOOABCRA-UHFFFAOYSA-N 0.000 claims 1
- OMJCGOMLYOLCQK-UHFFFAOYSA-N 4-benzyl-3-[(4-fluoronaphthalen-1-yl)methylsulfanyl]-5-phenyl-1,2,4-triazole Chemical compound C12=CC=CC=C2C(F)=CC=C1CSC(N1CC=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 OMJCGOMLYOLCQK-UHFFFAOYSA-N 0.000 claims 1
- XILSEGNRZUYELB-UHFFFAOYSA-N 4-benzyl-3-cyclohexyl-1h-1,2,4-triazole-5-thione Chemical compound C=1C=CC=CC=1CN1C(=S)NN=C1C1CCCCC1 XILSEGNRZUYELB-UHFFFAOYSA-N 0.000 claims 1
- RZGYDZODJLKUAS-UHFFFAOYSA-N 4-bromo-1-ethyl-n-(2-methylsulfanylphenyl)pyrazole-3-carboxamide Chemical compound CCN1C=C(Br)C(C(=O)NC=2C(=CC=CC=2)SC)=N1 RZGYDZODJLKUAS-UHFFFAOYSA-N 0.000 claims 1
- SOOIJPNTAQSLKT-UHFFFAOYSA-N 4-bromo-n-[3-(piperidine-1-carbonyl)phenyl]benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NC1=CC=CC(C(=O)N2CCCCC2)=C1 SOOIJPNTAQSLKT-UHFFFAOYSA-N 0.000 claims 1
- UZZVSLCBVYKWJP-UHFFFAOYSA-N 4-butyl-3-(3-chlorophenyl)-1h-1,2,4-triazole-5-thione Chemical compound CCCCN1C(S)=NN=C1C1=CC=CC(Cl)=C1 UZZVSLCBVYKWJP-UHFFFAOYSA-N 0.000 claims 1
- PPOIDZGFAOGDMF-UHFFFAOYSA-N 4-chloro-n-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)benzamide Chemical compound CC1(C)C(C2)CCC1(C)C2NC(=O)C1=CC=C(Cl)C=C1 PPOIDZGFAOGDMF-UHFFFAOYSA-N 0.000 claims 1
- LIXSCNLHIZAPAQ-UHFFFAOYSA-N 4-chloro-n-[3-methyl-1-oxo-1-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)pentan-2-yl]benzamide Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C(C(C)CC)NC(=O)C1=CC=C(Cl)C=C1 LIXSCNLHIZAPAQ-UHFFFAOYSA-N 0.000 claims 1
- DSEGTCSERAIXAT-UHFFFAOYSA-N 4-chloro-n-cyclohexyl-n-ethyl-3-nitrobenzamide Chemical compound C=1C=C(Cl)C([N+]([O-])=O)=CC=1C(=O)N(CC)C1CCCCC1 DSEGTCSERAIXAT-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- ODZPQBCHGIRTHD-UHFFFAOYSA-N 4-cyclopropyl-3-(2-methoxyethylsulfanyl)-5-(2-methoxyphenyl)-1,2,4-triazole Chemical compound C1CC1N1C(SCCOC)=NN=C1C1=CC=CC=C1OC ODZPQBCHGIRTHD-UHFFFAOYSA-N 0.000 claims 1
- AOUOKAHXWSRPEE-UHFFFAOYSA-N 4-cyclopropyl-3-(2-methoxyethylsulfanyl)-5-thiophen-2-yl-1,2,4-triazole Chemical compound C1CC1N1C(SCCOC)=NN=C1C1=CC=CS1 AOUOKAHXWSRPEE-UHFFFAOYSA-N 0.000 claims 1
- CTPUECQCTXSBMM-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O CTPUECQCTXSBMM-UHFFFAOYSA-N 0.000 claims 1
- REBPSPZTHZRFQR-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[(4-methylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=C(C)C=C1 REBPSPZTHZRFQR-UHFFFAOYSA-N 0.000 claims 1
- ZAFFZYIXKBDCHO-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 ZAFFZYIXKBDCHO-UHFFFAOYSA-N 0.000 claims 1
- GSIDREWZVJVEIF-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[(4-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 GSIDREWZVJVEIF-UHFFFAOYSA-N 0.000 claims 1
- ARBASIDAVPCJHA-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 ARBASIDAVPCJHA-UHFFFAOYSA-N 0.000 claims 1
- GXPGRBWFHBQUCF-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[(5-methyl-2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O GXPGRBWFHBQUCF-UHFFFAOYSA-N 0.000 claims 1
- XOMILXVIANENOJ-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 XOMILXVIANENOJ-UHFFFAOYSA-N 0.000 claims 1
- HEFFRPZKFLKGKN-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 HEFFRPZKFLKGKN-UHFFFAOYSA-N 0.000 claims 1
- TXVIAEAZRHFPSD-UHFFFAOYSA-N 4-ethyl-3-(2-methoxyphenyl)-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 TXVIAEAZRHFPSD-UHFFFAOYSA-N 0.000 claims 1
- FSZZUCJWZZZGGB-UHFFFAOYSA-N 4-ethyl-3-(2-phenoxyphenyl)-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 FSZZUCJWZZZGGB-UHFFFAOYSA-N 0.000 claims 1
- FGNZSUZIPBNIIH-UHFFFAOYSA-N 4-ethyl-3-(2-phenoxyphenyl)-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 FGNZSUZIPBNIIH-UHFFFAOYSA-N 0.000 claims 1
- PQEYJSXHIFZQHI-UHFFFAOYSA-N 4-ethyl-3-(2-phenoxyphenyl)-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 PQEYJSXHIFZQHI-UHFFFAOYSA-N 0.000 claims 1
- CKBYENMOKAIAPX-UHFFFAOYSA-N 4-ethyl-3-(4-methoxyphenyl)-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O CKBYENMOKAIAPX-UHFFFAOYSA-N 0.000 claims 1
- XESYVWOXHFYGJS-UHFFFAOYSA-N 4-ethyl-3-(4-methoxyphenyl)-5-[(4-methoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 XESYVWOXHFYGJS-UHFFFAOYSA-N 0.000 claims 1
- JNQQUNKQHQTCCT-UHFFFAOYSA-N 4-ethyl-3-(4-methoxyphenyl)-5-[(4-methylsulfonylphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 JNQQUNKQHQTCCT-UHFFFAOYSA-N 0.000 claims 1
- WYYGCPZFPLRJLX-UHFFFAOYSA-N 4-ethyl-3-(4-methoxyphenyl)-5-[(4-phenylmethoxyphenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 WYYGCPZFPLRJLX-UHFFFAOYSA-N 0.000 claims 1
- NCBBFMBQKVBQMZ-UHFFFAOYSA-N 4-ethyl-3-(4-methoxyphenyl)-5-[[3-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=CC(OC(F)(F)F)=C1 NCBBFMBQKVBQMZ-UHFFFAOYSA-N 0.000 claims 1
- WNHUSXQMCUNCQY-UHFFFAOYSA-N 4-ethyl-3-(4-methoxyphenyl)-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 WNHUSXQMCUNCQY-UHFFFAOYSA-N 0.000 claims 1
- VQIFYRTWGIWQEE-UHFFFAOYSA-N 4-ethyl-3-(5-methylthiophen-2-yl)-5-[(2-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O VQIFYRTWGIWQEE-UHFFFAOYSA-N 0.000 claims 1
- ARIBLEKFHQWSJO-UHFFFAOYSA-N 4-ethyl-3-(5-methylthiophen-2-yl)-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 ARIBLEKFHQWSJO-UHFFFAOYSA-N 0.000 claims 1
- ODGMVQORVYJCPO-UHFFFAOYSA-N 4-ethyl-3-(5-methylthiophen-2-yl)-5-[(4-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 ODGMVQORVYJCPO-UHFFFAOYSA-N 0.000 claims 1
- NJYUCKYVUWCUPX-UHFFFAOYSA-N 4-ethyl-3-(5-methylthiophen-2-yl)-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 NJYUCKYVUWCUPX-UHFFFAOYSA-N 0.000 claims 1
- PORJHQAGLXRDTL-UHFFFAOYSA-N 4-ethyl-3-(5-methylthiophen-2-yl)-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 PORJHQAGLXRDTL-UHFFFAOYSA-N 0.000 claims 1
- FCWOFTAAJAMCSV-UHFFFAOYSA-N 4-ethyl-3-[(2-nitrophenyl)methylsulfanyl]-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O FCWOFTAAJAMCSV-UHFFFAOYSA-N 0.000 claims 1
- IGCCKFJXTSOYOC-UHFFFAOYSA-N 4-ethyl-3-[(2-nitrophenyl)methylsulfanyl]-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC=CC=C1[N+]([O-])=O IGCCKFJXTSOYOC-UHFFFAOYSA-N 0.000 claims 1
- ZTEWMOVFUTVCQW-UHFFFAOYSA-N 4-ethyl-3-[(3-nitrophenyl)methylsulfanyl]-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 ZTEWMOVFUTVCQW-UHFFFAOYSA-N 0.000 claims 1
- XIBOJQFSTHLSIN-UHFFFAOYSA-N 4-ethyl-3-[(4-methoxyphenyl)methylsulfanyl]-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 XIBOJQFSTHLSIN-UHFFFAOYSA-N 0.000 claims 1
- LRPBBFNCFVEOPV-UHFFFAOYSA-N 4-ethyl-3-[(4-methoxyphenyl)methylsulfanyl]-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 LRPBBFNCFVEOPV-UHFFFAOYSA-N 0.000 claims 1
- ULZOWEVPJIIBKR-UHFFFAOYSA-N 4-ethyl-3-[(4-methoxyphenyl)methylsulfanyl]-5-naphthalen-1-yl-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 ULZOWEVPJIIBKR-UHFFFAOYSA-N 0.000 claims 1
- WNJFIVGBJDQDSS-UHFFFAOYSA-N 4-ethyl-3-[(4-methoxyphenyl)methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C(OC)C=C1 WNJFIVGBJDQDSS-UHFFFAOYSA-N 0.000 claims 1
- IBBGLODAOHHFMO-UHFFFAOYSA-N 4-ethyl-3-[(4-methylphenyl)methylsulfanyl]-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 IBBGLODAOHHFMO-UHFFFAOYSA-N 0.000 claims 1
- UHKOIOLBKJKVQD-UHFFFAOYSA-N 4-ethyl-3-[(4-methylphenyl)methylsulfanyl]-5-(4-nitrophenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC(=CC=2)[N+]([O-])=O)N(CC)C=1SCC1=CC=C(C)C=C1 UHKOIOLBKJKVQD-UHFFFAOYSA-N 0.000 claims 1
- NHTLTXJUEMHAMF-UHFFFAOYSA-N 4-ethyl-3-[(4-methylphenyl)methylsulfanyl]-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 NHTLTXJUEMHAMF-UHFFFAOYSA-N 0.000 claims 1
- AOSMUGPYCRQJDB-UHFFFAOYSA-N 4-ethyl-3-[(4-methylphenyl)methylsulfanyl]-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC=C(C)C=C1 AOSMUGPYCRQJDB-UHFFFAOYSA-N 0.000 claims 1
- JDORSLUONBPTFH-UHFFFAOYSA-N 4-ethyl-3-[(4-methylphenyl)methylsulfanyl]-5-naphthalen-1-yl-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 JDORSLUONBPTFH-UHFFFAOYSA-N 0.000 claims 1
- FVIGYVNFOJVLCQ-UHFFFAOYSA-N 4-ethyl-3-[(4-methylphenyl)methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C(C)C=C1 FVIGYVNFOJVLCQ-UHFFFAOYSA-N 0.000 claims 1
- PMHYXCRFZGYKLU-UHFFFAOYSA-N 4-ethyl-3-[(4-methylsulfonylphenyl)methylsulfanyl]-5-(2-phenoxyphenyl)-1,2,4-triazole Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 PMHYXCRFZGYKLU-UHFFFAOYSA-N 0.000 claims 1
- ZDNNSVQKWQFUCM-UHFFFAOYSA-N 4-ethyl-3-[(4-methylsulfonylphenyl)methylsulfanyl]-5-(5-methylthiophen-2-yl)-1,2,4-triazole Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 ZDNNSVQKWQFUCM-UHFFFAOYSA-N 0.000 claims 1
- OIFDZFISYKRABH-UHFFFAOYSA-N 4-ethyl-3-[(4-methylsulfonylphenyl)methylsulfanyl]-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 OIFDZFISYKRABH-UHFFFAOYSA-N 0.000 claims 1
- PBLTXWMLGMDBTA-UHFFFAOYSA-N 4-ethyl-3-[(4-methylsulfonylphenyl)methylsulfanyl]-5-naphthalen-1-yl-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 PBLTXWMLGMDBTA-UHFFFAOYSA-N 0.000 claims 1
- HAZPMUOTNFHHPN-UHFFFAOYSA-N 4-ethyl-3-[(4-methylsulfonylphenyl)methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C(S(C)(=O)=O)C=C1 HAZPMUOTNFHHPN-UHFFFAOYSA-N 0.000 claims 1
- ZZYCPGBATIITLA-UHFFFAOYSA-N 4-ethyl-3-[(4-nitrophenyl)methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 ZZYCPGBATIITLA-UHFFFAOYSA-N 0.000 claims 1
- FZOXXTPVJJDGQB-UHFFFAOYSA-N 4-ethyl-3-[(4-phenylmethoxyphenyl)methylsulfanyl]-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 FZOXXTPVJJDGQB-UHFFFAOYSA-N 0.000 claims 1
- NPOYIHYSCDSVPU-UHFFFAOYSA-N 4-ethyl-3-[(5-methyl-2-nitrophenyl)methylsulfanyl]-5-naphthalen-1-yl-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O NPOYIHYSCDSVPU-UHFFFAOYSA-N 0.000 claims 1
- ONTBBQIOQCFBHH-UHFFFAOYSA-N 4-ethyl-3-[(5-methyl-2-nitrophenyl)methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC(C)=CC=C1[N+]([O-])=O ONTBBQIOQCFBHH-UHFFFAOYSA-N 0.000 claims 1
- HZGSVZSAEVNTCU-UHFFFAOYSA-N 4-ethyl-3-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 HZGSVZSAEVNTCU-UHFFFAOYSA-N 0.000 claims 1
- WQMYUIWCKGPMOD-UHFFFAOYSA-N 4-ethyl-3-naphthalen-1-yl-5-[(3-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC=CC([N+]([O-])=O)=C1 WQMYUIWCKGPMOD-UHFFFAOYSA-N 0.000 claims 1
- WPMNOAFWIAOCDI-UHFFFAOYSA-N 4-ethyl-3-naphthalen-1-yl-5-[(4-nitrophenyl)methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC=C([N+]([O-])=O)C=C1 WPMNOAFWIAOCDI-UHFFFAOYSA-N 0.000 claims 1
- AFSZDIIOIYCDPL-UHFFFAOYSA-N 4-ethyl-3-naphthalen-1-yl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 AFSZDIIOIYCDPL-UHFFFAOYSA-N 0.000 claims 1
- WVOCXAPOSDDJDD-UHFFFAOYSA-N 4-ethyl-3-thiophen-2-yl-5-[[4-(trifluoromethoxy)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C(OC(F)(F)F)C=C1 WVOCXAPOSDDJDD-UHFFFAOYSA-N 0.000 claims 1
- MODKOYXFRWMZAF-UHFFFAOYSA-N 4-ethyl-3-thiophen-2-yl-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazole Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C(C(F)(F)F)C=C1 MODKOYXFRWMZAF-UHFFFAOYSA-N 0.000 claims 1
- JGFVAUUDLCHKQI-UHFFFAOYSA-N 4-hydroxy-n-[(4-hydroxyphenyl)methyl]-n-(2-methylpropyl)benzamide Chemical compound C=1C=C(O)C=CC=1C(=O)N(CC(C)C)CC1=CC=C(O)C=C1 JGFVAUUDLCHKQI-UHFFFAOYSA-N 0.000 claims 1
- ZDTDRQKMYDIBCL-UHFFFAOYSA-N 4-methyl-3-(4-methylphenyl)-5-(2-phenylethylsulfanyl)-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1C(N1C)=NN=C1SCCC1=CC=CC=C1 ZDTDRQKMYDIBCL-UHFFFAOYSA-N 0.000 claims 1
- VJTNNIOWMBZUGK-UHFFFAOYSA-N 4-methyl-3-[(2-methylphenyl)methylsulfanyl]-5-thiophen-2-yl-1,2,4-triazole Chemical compound CC1=CC=CC=C1CSC(N1C)=NN=C1C1=CC=CS1 VJTNNIOWMBZUGK-UHFFFAOYSA-N 0.000 claims 1
- SFMXKNDDMRQDNZ-UHFFFAOYSA-N 4-methyl-3-[(4-methylphenyl)methylsulfanyl]-5-[3-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1CSC(N1C)=NN=C1C1=CC=CC(C(F)(F)F)=C1 SFMXKNDDMRQDNZ-UHFFFAOYSA-N 0.000 claims 1
- YSWSUZCEBFYVND-UHFFFAOYSA-N 4-methyl-3-[(4-nitrophenyl)methylsulfanyl]-5-phenyl-1,2,4-triazole Chemical compound N=1N=C(C=2C=CC=CC=2)N(C)C=1SCC1=CC=C([N+]([O-])=O)C=C1 YSWSUZCEBFYVND-UHFFFAOYSA-N 0.000 claims 1
- HVACUGYQMUTBDJ-UHFFFAOYSA-N 4-methyl-3-[3-[(4-methylphenyl)methoxy]thiophen-2-yl]-5-methylsulfanyl-1,2,4-triazole Chemical compound CN1C(SC)=NN=C1C1=C(OCC=2C=CC(C)=CC=2)C=CS1 HVACUGYQMUTBDJ-UHFFFAOYSA-N 0.000 claims 1
- JGPSODNQURDKFU-UHFFFAOYSA-N 4-methyl-3-[3-[[3-(trifluoromethyl)phenyl]methoxy]thiophen-2-yl]-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(C)C(C2=C(C=CS2)OCC=2C=C(C=CC=2)C(F)(F)F)=N1 JGPSODNQURDKFU-UHFFFAOYSA-N 0.000 claims 1
- BTMDFZSYLBTEOT-UHFFFAOYSA-N 4-methyl-3-methylsulfanyl-5-[3-[[3-(trifluoromethyl)phenyl]methoxy]thiophen-2-yl]-1,2,4-triazole Chemical compound CN1C(SC)=NN=C1C1=C(OCC=2C=C(C=CC=2)C(F)(F)F)C=CS1 BTMDFZSYLBTEOT-UHFFFAOYSA-N 0.000 claims 1
- IJOYYGFIORIFJG-UHFFFAOYSA-N 4-methyl-5-(4-methyl-5-prop-2-ynylsulfanyl-1,2,4-triazol-3-yl)-2-phenyl-1,3-thiazole Chemical compound CC=1N=C(C=2C=CC=CC=2)SC=1C1=NN=C(SCC#C)N1C IJOYYGFIORIFJG-UHFFFAOYSA-N 0.000 claims 1
- WBRQXZXOGRAPJI-UHFFFAOYSA-N 4-methyl-n-[2-(phenoxazine-10-carbonyl)phenyl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)N1C2=CC=CC=C2OC2=CC=CC=C21 WBRQXZXOGRAPJI-UHFFFAOYSA-N 0.000 claims 1
- AFPFMPNSJWQYPJ-UHFFFAOYSA-N 4-methyl-n-[3-methyl-1-oxo-1-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)pentan-2-yl]benzamide Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C(C(C)CC)NC(=O)C1=CC=C(C)C=C1 AFPFMPNSJWQYPJ-UHFFFAOYSA-N 0.000 claims 1
- NWEAQWFUCTVJDI-UHFFFAOYSA-N 4-methyl-n-naphthalen-1-yl-2-phenyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C3=CC=CC=C3C=CC=2)=C(C)N=C1C1=CC=CC=C1 NWEAQWFUCTVJDI-UHFFFAOYSA-N 0.000 claims 1
- LHNSBIUPQDSYIO-UHFFFAOYSA-N 4-tert-butyl-n-cyclooctylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1CCCCCCC1 LHNSBIUPQDSYIO-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- UMCSDNAWBPUNIJ-UHFFFAOYSA-N 5,5-dimethyl-3-(3,4,5-trimethoxyphenyl)-6h-[1,2,4]triazolo[3,4-a]isoquinoline Chemical compound COC1=C(OC)C(OC)=CC(C=2N3C(C)(C)CC4=CC=CC=C4C3=NN=2)=C1 UMCSDNAWBPUNIJ-UHFFFAOYSA-N 0.000 claims 1
- LFESZQRDPUZMOE-UHFFFAOYSA-N 5,5-dimethyl-3-(4-methylphenyl)-6h-[1,2,4]triazolo[3,4-a]isoquinoline Chemical compound C1=CC(C)=CC=C1C1=NN=C2N1C(C)(C)CC1=CC=CC=C12 LFESZQRDPUZMOE-UHFFFAOYSA-N 0.000 claims 1
- CSCOJYVCYSWDLT-UHFFFAOYSA-N 5,5-dimethyl-3-phenyl-6h-[1,2,4]triazolo[3,4-a]isoquinoline Chemical compound N12C(C)(C)CC3=CC=CC=C3C2=NN=C1C1=CC=CC=C1 CSCOJYVCYSWDLT-UHFFFAOYSA-N 0.000 claims 1
- ARVNJCBUCQXYTF-UHFFFAOYSA-N 5,6-dihydrobenzo[b][1]benzazepin-11-yl-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C2=CC=CC=C2CCC2=CC=CC=C21 ARVNJCBUCQXYTF-UHFFFAOYSA-N 0.000 claims 1
- KLWVLLPTXFKYLW-UHFFFAOYSA-N 5-(2,6-dichlorophenyl)sulfanyl-n-(naphthalen-1-ylmethyl)pentanamide Chemical compound ClC1=CC=CC(Cl)=C1SCCCCC(=O)NCC1=CC=CC2=CC=CC=C12 KLWVLLPTXFKYLW-UHFFFAOYSA-N 0.000 claims 1
- OADYUHNMWNRALE-UHFFFAOYSA-N 5-(2,6-dichlorophenyl)sulfanyl-n-[2-[3-(trifluoromethyl)phenyl]ethyl]pentanamide Chemical compound FC(F)(F)C1=CC=CC(CCNC(=O)CCCCSC=2C(=CC=CC=2Cl)Cl)=C1 OADYUHNMWNRALE-UHFFFAOYSA-N 0.000 claims 1
- IGJLEHOJTAUBNS-UHFFFAOYSA-N 5-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(C(=O)N2C3CC(CC(C)(C)C3)(C2)C)=C1 IGJLEHOJTAUBNS-UHFFFAOYSA-N 0.000 claims 1
- RMDCDDMQIQXVPW-UHFFFAOYSA-N 5-(5-benzylsulfanyl-4-ethyl-1,2,4-triazol-3-yl)-4-methylthiadiazole Chemical compound N=1N=C(C2=C(N=NS2)C)N(CC)C=1SCC1=CC=CC=C1 RMDCDDMQIQXVPW-UHFFFAOYSA-N 0.000 claims 1
- GAPVDAUIUSONCC-UHFFFAOYSA-N 5-[(4-nitrophenyl)methylsulfanyl]-1h-1,2,4-triazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1CSC1=NC=NN1 GAPVDAUIUSONCC-UHFFFAOYSA-N 0.000 claims 1
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- FWORSSYSVONBFV-UHFFFAOYSA-N [1-[[4-(trifluoromethoxy)phenyl]methyl]indol-5-yl]-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)C(C=C1C=C2)=CC=C1N2CC1=CC=C(OC(F)(F)F)C=C1 FWORSSYSVONBFV-UHFFFAOYSA-N 0.000 claims 1
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- JTAJMIZQWOCLTK-UHFFFAOYSA-N [3-[(4-bromopyrazol-1-yl)methyl]phenyl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=CC(CN2N=CC(Br)=C2)=C1 JTAJMIZQWOCLTK-UHFFFAOYSA-N 0.000 claims 1
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- YSIGHMXTVPOKOG-UHFFFAOYSA-N [4-(2-chloro-6-nitrophenyl)piperazin-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1CCN(C=2C(=CC=CC=2Cl)[N+]([O-])=O)CC1 YSIGHMXTVPOKOG-UHFFFAOYSA-N 0.000 claims 1
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- LHZYREUROAQJCW-UHFFFAOYSA-N [4-(3,5-dimethylpiperidine-1-carbonyl)phenyl] acetate Chemical compound C1C(C)CC(C)CN1C(=O)C1=CC=C(OC(C)=O)C=C1 LHZYREUROAQJCW-UHFFFAOYSA-N 0.000 claims 1
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- JTHNOLKHHKCTPL-UHFFFAOYSA-N [4-(4-methylpiperidine-1-carbonyl)phenyl] acetate Chemical compound C1CC(C)CCN1C(=O)C1=CC=C(OC(C)=O)C=C1 JTHNOLKHHKCTPL-UHFFFAOYSA-N 0.000 claims 1
- DRTKTDQTTOPSAQ-UHFFFAOYSA-N [4-(adamantane-1-carbonylamino)-2,6-dimethylpyridin-3-yl] adamantane-1-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)OC1=C(NC(=O)C23CC4CC(CC(C4)C2)C3)C=C(C)N=C1C DRTKTDQTTOPSAQ-UHFFFAOYSA-N 0.000 claims 1
- ITMCBJAQMJMNNC-UHFFFAOYSA-N [4-(adamantane-1-carbonylamino)-2-ethyl-6-methylpyridin-3-yl] adamantane-1-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)OC1=C(NC(=O)C23CC4CC(CC(C4)C2)C3)C=C(C)N=C1CC ITMCBJAQMJMNNC-UHFFFAOYSA-N 0.000 claims 1
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- XQKXJVMZSDQGOF-UHFFFAOYSA-N [4-(benzenesulfonyl)phenyl]-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)C(C=C1)=CC=C1S(=O)(=O)C1=CC=CC=C1 XQKXJVMZSDQGOF-UHFFFAOYSA-N 0.000 claims 1
- DGWFQDMNODCWRA-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(CC(C)(C)C2)CC2(C)C1 DGWFQDMNODCWRA-UHFFFAOYSA-N 0.000 claims 1
- CQOAUJONINNUQL-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-(3-hydroxy-3-methyl-8-azabicyclo[3.2.1]octan-8-yl)methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C2CCC1CC(C)(O)C2 CQOAUJONINNUQL-UHFFFAOYSA-N 0.000 claims 1
- HNFLFHXMJRABSF-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-(3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C2CCC1CC(O)C2 HNFLFHXMJRABSF-UHFFFAOYSA-N 0.000 claims 1
- BFXZQIBGNIOOGD-UHFFFAOYSA-N [4-(tetrazol-1-yl)phenyl]-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)C(C=C1)=CC=C1N1C=NN=N1 BFXZQIBGNIOOGD-UHFFFAOYSA-N 0.000 claims 1
- BNQBIMPSYNRLDO-UHFFFAOYSA-N [4-[(2-methoxynaphthalen-1-yl)methyl]piperazin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCN(CC=2C3=CC=CC=C3C=CC=2OC)CC1 BNQBIMPSYNRLDO-UHFFFAOYSA-N 0.000 claims 1
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- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 claims 1
- DOHBALJMFBMLDS-UHFFFAOYSA-N cyclohexyl 2-[(4-benzyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]acetate Chemical compound C1CCCCC1OC(=O)CSC(N1CC=2C=CC=CC=2)=NN=C1C1=CC=CN=C1 DOHBALJMFBMLDS-UHFFFAOYSA-N 0.000 claims 1
- GDYPXATYYNJLNJ-UHFFFAOYSA-N cyclohexyl 2-[(5-benzyl-4-methyl-1,2,4-triazol-3-yl)sulfanyl]acetate Chemical compound N=1N=C(SCC(=O)OC2CCCCC2)N(C)C=1CC1=CC=CC=C1 GDYPXATYYNJLNJ-UHFFFAOYSA-N 0.000 claims 1
- XKVSTBWZIGVECM-UHFFFAOYSA-N cyclohexyl 2-[[4-(furan-2-ylmethyl)-5-(4-hydroxyphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound C1=CC(O)=CC=C1C(N1CC=2OC=CC=2)=NN=C1SCC(=O)OC1CCCCC1 XKVSTBWZIGVECM-UHFFFAOYSA-N 0.000 claims 1
- SXDVTPWMORKRBI-UHFFFAOYSA-N cyclohexyl 2-[[4-ethyl-5-(4-hydroxyphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC(=O)OC1CCCCC1 SXDVTPWMORKRBI-UHFFFAOYSA-N 0.000 claims 1
- OEEDQEZCWMYAJS-UHFFFAOYSA-N cyclohexyl 2-[[4-ethyl-5-[(4-fluoroanilino)methyl]-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1N=C(SCC(=O)OC2CCCCC2)N(CC)C=1CNC1=CC=C(F)C=C1 OEEDQEZCWMYAJS-UHFFFAOYSA-N 0.000 claims 1
- MUAQWJFXTAODNQ-UHFFFAOYSA-N cyclohexyl 2-[[5-(4-bromophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1N=C(C=2C=CC(Br)=CC=2)N(C)C=1SCC(=O)OC1CCCCC1 MUAQWJFXTAODNQ-UHFFFAOYSA-N 0.000 claims 1
- QKPVMEAYJPEUBD-UHFFFAOYSA-N cyclohexyl 2-[[5-[(2,4-dimethylanilino)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1N=C(SCC(=O)OC2CCCCC2)N(CC)C=1CNC1=CC=C(C)C=C1C QKPVMEAYJPEUBD-UHFFFAOYSA-N 0.000 claims 1
- APQWWESOSGWSNQ-UHFFFAOYSA-N cyclohexyl 2-[[5-[(2-chloroanilino)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1N=C(SCC(=O)OC2CCCCC2)N(CC)C=1CNC1=CC=CC=C1Cl APQWWESOSGWSNQ-UHFFFAOYSA-N 0.000 claims 1
- MUAVJQMZQZZVSX-UHFFFAOYSA-N cyclohexyl 2-[[5-[(3-chloro-4-methylanilino)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1N=C(SCC(=O)OC2CCCCC2)N(CC)C=1CNC1=CC=C(C)C(Cl)=C1 MUAVJQMZQZZVSX-UHFFFAOYSA-N 0.000 claims 1
- WJVDRVKZRSDMSC-UHFFFAOYSA-N cyclohexyl 2-[[5-[(4-chloroanilino)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1N=C(SCC(=O)OC2CCCCC2)N(CC)C=1CNC1=CC=C(Cl)C=C1 WJVDRVKZRSDMSC-UHFFFAOYSA-N 0.000 claims 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 claims 1
- LQJVHIOSGBLNRR-UHFFFAOYSA-N ethyl 1-(3-cyclopentylpropanoyl)piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)CCC1CCCC1 LQJVHIOSGBLNRR-UHFFFAOYSA-N 0.000 claims 1
- LXMMPYWOJVDLMJ-UHFFFAOYSA-N ethyl 1-benzoylpiperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C1=CC=CC=C1 LXMMPYWOJVDLMJ-UHFFFAOYSA-N 0.000 claims 1
- DZTAJGBADYJNRE-UHFFFAOYSA-N ethyl 2-(adamantane-1-carbonylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1NC(=O)C1(C2)CC(C3)CC2CC3C1 DZTAJGBADYJNRE-UHFFFAOYSA-N 0.000 claims 1
- CDBCPHKJBMRFHR-UHFFFAOYSA-N ethyl 2-[(4-benzyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]acetate Chemical compound C=1C=CC=CC=1CN1C(SCC(=O)OCC)=NN=C1C1=CC=CC=C1 CDBCPHKJBMRFHR-UHFFFAOYSA-N 0.000 claims 1
- VRMSQWSZMZMFFT-UHFFFAOYSA-N ethyl 2-[6-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)indol-1-yl]acetate Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C1=CC=C2C=CN(CC(=O)OCC)C2=C1 VRMSQWSZMZMFFT-UHFFFAOYSA-N 0.000 claims 1
- AZJBUSLFCKOROQ-UHFFFAOYSA-N ethyl 2-[[4-(2-phenylethyl)-5-pyridin-3-yl-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound C=1C=CC=CC=1CCN1C(SCC(=O)OCC)=NN=C1C1=CC=CN=C1 AZJBUSLFCKOROQ-UHFFFAOYSA-N 0.000 claims 1
- RWNCHDWXPXMQKN-UHFFFAOYSA-N ethyl 2-[[4-benzyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound C=1C=CC=CC=1CN1C(SCC(=O)OCC)=NN=C1C1=CC=C(OC)C=C1 RWNCHDWXPXMQKN-UHFFFAOYSA-N 0.000 claims 1
- MVQVPGRPNVSFJT-UHFFFAOYSA-N ethyl 2-[[4-ethyl-5-(2-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound CCN1C(SCC(=O)OCC)=NN=C1C1=CC=CC=C1OC MVQVPGRPNVSFJT-UHFFFAOYSA-N 0.000 claims 1
- DXAPIMIWEMKPPC-UHFFFAOYSA-N ethyl 2-[benzyl-(4-nitrobenzoyl)amino]acetate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=O)N(CC(=O)OCC)CC1=CC=CC=C1 DXAPIMIWEMKPPC-UHFFFAOYSA-N 0.000 claims 1
- WXWBQJRIFVEWGT-UHFFFAOYSA-N ethyl 2-amino-4-methyl-5-(piperidine-1-carbonyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC(C(=O)N2CCCCC2)=C1C WXWBQJRIFVEWGT-UHFFFAOYSA-N 0.000 claims 1
- JJLSXJUIHYRBOV-UHFFFAOYSA-N ethyl 2-amino-5-(azepane-1-carbonyl)-4-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC(C(=O)N2CCCCCC2)=C1C JJLSXJUIHYRBOV-UHFFFAOYSA-N 0.000 claims 1
- ONEQTHCBJHMZHZ-UHFFFAOYSA-N ethyl 2-amino-5-(cyclohexylcarbamoyl)-4-methylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC(C(=O)NC2CCCCC2)=C1C ONEQTHCBJHMZHZ-UHFFFAOYSA-N 0.000 claims 1
- XUENQTYWYCCBGX-UHFFFAOYSA-N ethyl 3-[5-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)indol-1-yl]propanoate Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C1=CC=C2N(CCC(=O)OCC)C=CC2=C1 XUENQTYWYCCBGX-UHFFFAOYSA-N 0.000 claims 1
- ZPVCURRGCDGYLA-UHFFFAOYSA-N ethyl 3-[[5-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-indole-3-carbonyl]amino]propanoate Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C1=CC=C2NC=C(C(=O)NCCC(=O)OCC)C2=C1 ZPVCURRGCDGYLA-UHFFFAOYSA-N 0.000 claims 1
- WDJQYZSPNXKRJE-UHFFFAOYSA-N ethyl 4-[[2-[(5-cyclohexyl-4-methyl-1,2,4-triazol-3-yl)sulfanyl]acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)CSC(N1C)=NN=C1C1CCCCC1 WDJQYZSPNXKRJE-UHFFFAOYSA-N 0.000 claims 1
- ZUZXVUWNKNIUII-UHFFFAOYSA-N ethyl 4-[[2-[[5-(2-bromophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)CSC(N1C)=NN=C1C1=CC=CC=C1Br ZUZXVUWNKNIUII-UHFFFAOYSA-N 0.000 claims 1
- APSWRCMFDKPCOL-UHFFFAOYSA-N ethyl 4-[[3-methoxy-5-(pyridine-2-carbonyl)benzoyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC(=O)C1=CC(OC)=CC(C(=O)C=2N=CC=CC=2)=C1 APSWRCMFDKPCOL-UHFFFAOYSA-N 0.000 claims 1
- RKEMWDBWPAAWAK-UHFFFAOYSA-N ethyl 6-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-indole-3-carboxylate Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C1=CC=C2C(C(=O)OCC)=CNC2=C1 RKEMWDBWPAAWAK-UHFFFAOYSA-N 0.000 claims 1
- KBIJOMUAIJBJRE-UHFFFAOYSA-N furan-2-yl-[4-(4-methylphenyl)sulfonylpiperazin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCN(C(=O)C=2OC=CC=2)CC1 KBIJOMUAIJBJRE-UHFFFAOYSA-N 0.000 claims 1
- DNJFMXHTNUVNII-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazol-6-yl-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)methanone Chemical compound C1C2CC(C)(C)CC1(C)CN2C(=O)C1=CN(C=CS2)C2=N1 DNJFMXHTNUVNII-UHFFFAOYSA-N 0.000 claims 1
- IENZCGNHSIMFJE-UHFFFAOYSA-N indole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC=CC2=C1 IENZCGNHSIMFJE-UHFFFAOYSA-N 0.000 claims 1
- ZJZIVDCVOLKKFB-UHFFFAOYSA-N methyl 2-(adamantane-1-carbonylamino)-3-phenylpropanoate Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NC(C(=O)OC)CC1=CC=CC=C1 ZJZIVDCVOLKKFB-UHFFFAOYSA-N 0.000 claims 1
- HJWKNMQFBNEIPC-UHFFFAOYSA-N methyl 2-[(2-methoxybenzoyl)amino]-4-methyl-5-(piperidine-1-carbonyl)thiophene-3-carboxylate Chemical compound COC(=O)C=1C(C)=C(C(=O)N2CCCCC2)SC=1NC(=O)C1=CC=CC=C1OC HJWKNMQFBNEIPC-UHFFFAOYSA-N 0.000 claims 1
- FBSJQHFZRYKPQK-UHFFFAOYSA-N methyl 2-[(3-fluorobenzoyl)amino]-4-methyl-5-(piperidine-1-carbonyl)thiophene-3-carboxylate Chemical compound COC(=O)C=1C(C)=C(C(=O)N2CCCCC2)SC=1NC(=O)C1=CC=CC(F)=C1 FBSJQHFZRYKPQK-UHFFFAOYSA-N 0.000 claims 1
- XVYXYBDZHBRSDJ-UHFFFAOYSA-N methyl 2-[[2-[[4-ethyl-5-(3-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]benzoate Chemical compound N=1N=C(C=2C=C(C)C=CC=2)N(CC)C=1SCC(=O)NC1=CC=CC=C1C(=O)OC XVYXYBDZHBRSDJ-UHFFFAOYSA-N 0.000 claims 1
- PGWMMDGZOLEYMY-UHFFFAOYSA-N methyl 2-[[2-[[4-methyl-5-(3-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CSC(N1C)=NN=C1C1=CC=CC(C)=C1 PGWMMDGZOLEYMY-UHFFFAOYSA-N 0.000 claims 1
- LLGCIOWMDCLFGV-UHFFFAOYSA-N methyl 2-[[3-(4-methylphenyl)adamantane-1-carbonyl]amino]propanoate Chemical compound C1C(C(=O)NC(C)C(=O)OC)(C2)CC(C3)CC1CC32C1=CC=C(C)C=C1 LLGCIOWMDCLFGV-UHFFFAOYSA-N 0.000 claims 1
- ANQMBDBYRBFSQZ-UHFFFAOYSA-N methyl 3-[6-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-benzimidazol-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2NC3=CC=C(C=C3N=2)C(=O)N2C3CC(CC(C)(C)C3)(C)C2)=C1 ANQMBDBYRBFSQZ-UHFFFAOYSA-N 0.000 claims 1
- DXZPXECYINTUDB-UHFFFAOYSA-N methyl 4-[(4-ethyl-5-naphthalen-1-yl-1,2,4-triazol-3-yl)sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C3=CC=CC=C3C=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 DXZPXECYINTUDB-UHFFFAOYSA-N 0.000 claims 1
- OTMTWNJAHZRMCH-UHFFFAOYSA-N methyl 4-[(4-ethyl-5-pyridin-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2N=CC=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 OTMTWNJAHZRMCH-UHFFFAOYSA-N 0.000 claims 1
- PQKXWFNDCWLHCO-UHFFFAOYSA-N methyl 4-[(4-ethyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C=NC=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 PQKXWFNDCWLHCO-UHFFFAOYSA-N 0.000 claims 1
- BJMZPFJOFOIPTC-UHFFFAOYSA-N methyl 4-[(4-ethyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 BJMZPFJOFOIPTC-UHFFFAOYSA-N 0.000 claims 1
- WEZWMAPLBZLUEG-UHFFFAOYSA-N methyl 4-[(4-ethyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2SC=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 WEZWMAPLBZLUEG-UHFFFAOYSA-N 0.000 claims 1
- WRHXNHYSDZMSOV-UHFFFAOYSA-N methyl 4-[[2-[[4-methyl-5-(2-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)CSC(N1C)=NN=C1C1=CC=CC=C1C WRHXNHYSDZMSOV-UHFFFAOYSA-N 0.000 claims 1
- MQQQHWSZLZEKBK-UHFFFAOYSA-N methyl 4-[[2-[[5-(2-bromophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]benzoate Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC(=O)NC1=CC=C(C(=O)OC)C=C1 MQQQHWSZLZEKBK-UHFFFAOYSA-N 0.000 claims 1
- PTRXAQBPTBMLQR-UHFFFAOYSA-N methyl 4-[[2-[[5-(2-bromophenyl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)CSC(N1C)=NN=C1C1=CC=CC=C1Br PTRXAQBPTBMLQR-UHFFFAOYSA-N 0.000 claims 1
- QWEKOVAQYQYMSN-UHFFFAOYSA-N methyl 4-[[4-ethyl-5-(2-hydroxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C(=CC=CC=2)O)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 QWEKOVAQYQYMSN-UHFFFAOYSA-N 0.000 claims 1
- XJCOOCQMCVDBLZ-UHFFFAOYSA-N methyl 4-[[4-ethyl-5-(2-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 XJCOOCQMCVDBLZ-UHFFFAOYSA-N 0.000 claims 1
- AYWMHTZPTFMTIK-UHFFFAOYSA-N methyl 4-[[4-ethyl-5-(2-methylsulfanylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 AYWMHTZPTFMTIK-UHFFFAOYSA-N 0.000 claims 1
- RESQYUISXLOHOX-UHFFFAOYSA-N methyl 4-[[4-ethyl-5-(2-phenoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 RESQYUISXLOHOX-UHFFFAOYSA-N 0.000 claims 1
- YJCHGKKNQDCWIN-UHFFFAOYSA-N methyl 4-[[4-ethyl-5-(4-hydroxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C=CC(O)=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 YJCHGKKNQDCWIN-UHFFFAOYSA-N 0.000 claims 1
- WHGLCEFWBQUWMW-UHFFFAOYSA-N methyl 4-[[4-ethyl-5-(4-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C=CC(OC)=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 WHGLCEFWBQUWMW-UHFFFAOYSA-N 0.000 claims 1
- JZNXWDJIFAVCGW-UHFFFAOYSA-N methyl 4-[[4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 JZNXWDJIFAVCGW-UHFFFAOYSA-N 0.000 claims 1
- WJORAEFMESMYRR-UHFFFAOYSA-N methyl 4-[[4-ethyl-5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 WJORAEFMESMYRR-UHFFFAOYSA-N 0.000 claims 1
- FNUVMUDNXXDPHH-UHFFFAOYSA-N methyl 4-[[5-(1,3-benzodioxol-5-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C=C3OCOC3=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 FNUVMUDNXXDPHH-UHFFFAOYSA-N 0.000 claims 1
- QGKZADYDXZUJFG-UHFFFAOYSA-N methyl 4-[[5-(1-benzothiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 QGKZADYDXZUJFG-UHFFFAOYSA-N 0.000 claims 1
- JEVWSXYOUBTXQJ-UHFFFAOYSA-N methyl 4-[[5-(3-chloro-4-methylthiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C2=C(C(C)=CS2)Cl)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 JEVWSXYOUBTXQJ-UHFFFAOYSA-N 0.000 claims 1
- YFOVORSXBYVNRX-UHFFFAOYSA-N methyl 4-[[5-(4-chlorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 YFOVORSXBYVNRX-UHFFFAOYSA-N 0.000 claims 1
- FYDNCJPPYJAAJD-UHFFFAOYSA-N methyl 4-[[5-(5-chlorothiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2SC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 FYDNCJPPYJAAJD-UHFFFAOYSA-N 0.000 claims 1
- FWBBMKQKFJQKIC-UHFFFAOYSA-N methyl 4-[[5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]benzoate Chemical compound N=1N=C(C=2C=CC(=CC=2)N2C(=CC=C2C)C)N(CC)C=1SCC1=CC=C(C(=O)OC)C=C1 FWBBMKQKFJQKIC-UHFFFAOYSA-N 0.000 claims 1
- ISINGHVAECMBPX-UHFFFAOYSA-N n'-(3,7,7-trimethyl-4-bicyclo[2.2.1]heptanyl)-n-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)hexanediamide Chemical compound C1C(C2(C)C)CCC2(C)C1NC(=O)CCCCC(=O)NC1(C2(C)C)CCC2CC1C ISINGHVAECMBPX-UHFFFAOYSA-N 0.000 claims 1
- CBICPLYVLNSDTG-UHFFFAOYSA-N n'-(4-methylphenyl)-n-[4-(1-naphthalen-2-ylsulfonylpiperidin-3-yl)butyl]oxamide Chemical compound C1=CC(C)=CC=C1NC(=O)C(=O)NCCCCC1CN(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)CCC1 CBICPLYVLNSDTG-UHFFFAOYSA-N 0.000 claims 1
- XQUPIYUNYHIPPF-UHFFFAOYSA-N n,n'-bis(2,4-difluorophenyl)-3,3-dimethylpentanediamide Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)CC(C)(C)CC(=O)NC1=CC=C(F)C=C1F XQUPIYUNYHIPPF-UHFFFAOYSA-N 0.000 claims 1
- CZZLQUVWVGDTCW-UHFFFAOYSA-N n,n-dibenzyl-1h-indole-5-carboxamide Chemical compound C=1C=C2NC=CC2=CC=1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 CZZLQUVWVGDTCW-UHFFFAOYSA-N 0.000 claims 1
- FBVXYPJHMXIEIE-UHFFFAOYSA-N n,n-dibenzyl-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 FBVXYPJHMXIEIE-UHFFFAOYSA-N 0.000 claims 1
- DAKYKYJUYQRPIB-UHFFFAOYSA-N n,n-dibenzyl-3,4-dichlorobenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 DAKYKYJUYQRPIB-UHFFFAOYSA-N 0.000 claims 1
- LGXXIXHEOKUPTC-UHFFFAOYSA-N n,n-dibenzyl-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 LGXXIXHEOKUPTC-UHFFFAOYSA-N 0.000 claims 1
- BSVBUMJNVPLWLP-UHFFFAOYSA-N n,n-dibenzyl-3-chloro-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 BSVBUMJNVPLWLP-UHFFFAOYSA-N 0.000 claims 1
- UGHSNYACOXBNJJ-UHFFFAOYSA-N n,n-dibenzyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 UGHSNYACOXBNJJ-UHFFFAOYSA-N 0.000 claims 1
- ASTXNWPSIPDNBE-UHFFFAOYSA-N n,n-dibenzylthiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 ASTXNWPSIPDNBE-UHFFFAOYSA-N 0.000 claims 1
- UDVDKLWQHCSBQO-UHFFFAOYSA-N n,n-diethyl-1-(2-nitrophenyl)piperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1C1=CC=CC=C1[N+]([O-])=O UDVDKLWQHCSBQO-UHFFFAOYSA-N 0.000 claims 1
- SAPCUOAGJIIDAQ-UHFFFAOYSA-N n,n-diethyl-1-(4-nitrophenyl)piperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1C1=CC=C([N+]([O-])=O)C=C1 SAPCUOAGJIIDAQ-UHFFFAOYSA-N 0.000 claims 1
- QKSOXXNRTPOXPG-UHFFFAOYSA-N n,n-dimethyl-2-[3-(4-nitrophenyl)-1-adamantyl]acetamide Chemical compound C1C(CC(=O)N(C)C)(C2)CC(C3)CC1CC32C1=CC=C([N+]([O-])=O)C=C1 QKSOXXNRTPOXPG-UHFFFAOYSA-N 0.000 claims 1
- SPJBYXZFFMMCEN-UHFFFAOYSA-N n,n-dimethyl-5-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-indole-3-carboxamide Chemical compound C1C(CC(C)(C)C2)(C)CC2N1C(=O)C1=CC=C2NC=C(C(=O)N(C)C)C2=C1 SPJBYXZFFMMCEN-UHFFFAOYSA-N 0.000 claims 1
- RMRZPLJAVNSFCJ-UHFFFAOYSA-N n,n-dimethyladamantane-1-carboxamide Chemical compound C1C(C2)CC3CC2CC1(C(=O)N(C)C)C3 RMRZPLJAVNSFCJ-UHFFFAOYSA-N 0.000 claims 1
- JCOZSOSHYHVYRW-UHFFFAOYSA-N n-(1,1-dioxothiolan-3-yl)-5-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-indole-3-carboxamide Chemical compound C1C(C)(C)CC(C)(C2)CC1N2C(=O)C(C=C12)=CC=C1NC=C2C(=O)NC1CCS(=O)(=O)C1 JCOZSOSHYHVYRW-UHFFFAOYSA-N 0.000 claims 1
- NHNAYPQCUJLMGT-UHFFFAOYSA-N n-(1,1-dioxothiolan-3-yl)adamantane-1-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NC1CCS(=O)(=O)C1 NHNAYPQCUJLMGT-UHFFFAOYSA-N 0.000 claims 1
- KILTUXSBXYMWIF-UHFFFAOYSA-N n-(1,2,3,4-tetrahydronaphthalen-1-yl)-1-benzothiophene-3-carboxamide Chemical compound C1=CC=C2C(C(NC3C4=CC=CC=C4CCC3)=O)=CSC2=C1 KILTUXSBXYMWIF-UHFFFAOYSA-N 0.000 claims 1
- HOGHZVFLOZCSQV-UHFFFAOYSA-N n-(1,3-benzodioxol-4-yl)-1-butylpyrrolidine-2-carboxamide Chemical compound CCCCN1CCCC1C(=O)NC1=CC=CC2=C1OCO2 HOGHZVFLOZCSQV-UHFFFAOYSA-N 0.000 claims 1
- HUXDABLEJAOGSF-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-2,4-dichlorobenzamide Chemical compound ClC1=CC(Cl)=CC=C1C(=O)NC1=CC=C(OCO2)C2=C1 HUXDABLEJAOGSF-UHFFFAOYSA-N 0.000 claims 1
- VZTYFRREFGDKEM-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-2-chlorobenzamide Chemical compound ClC1=CC=CC=C1C(=O)NC1=CC=C(OCO2)C2=C1 VZTYFRREFGDKEM-UHFFFAOYSA-N 0.000 claims 1
- HJRIGSNQNHOTML-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-(2-cyanophenyl)sulfanylbenzamide Chemical compound C=1C=C2OCOC2=CC=1CNC(=O)C1=CC=CC=C1SC1=CC=CC=C1C#N HJRIGSNQNHOTML-UHFFFAOYSA-N 0.000 claims 1
- IHVKROPZRZOWMQ-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)adamantane-1-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NCC1=CC=C(OCO2)C2=C1 IHVKROPZRZOWMQ-UHFFFAOYSA-N 0.000 claims 1
- WSHKKNGZOWLLMK-UHFFFAOYSA-N n-(1-adamantyl)-1-methylindole-3-carboxamide Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)NC1(C2)CC(C3)CC2CC3C1 WSHKKNGZOWLLMK-UHFFFAOYSA-N 0.000 claims 1
- NRCXUNFIDNZGJT-UHFFFAOYSA-N n-(1-adamantyl)-2,4-dichloro-n-ethylbenzamide Chemical compound C1C(C2)CC(C3)CC2CC13N(CC)C(=O)C1=CC=C(Cl)C=C1Cl NRCXUNFIDNZGJT-UHFFFAOYSA-N 0.000 claims 1
- FVMFGNBRCDDCPL-UHFFFAOYSA-N n-(1-adamantyl)-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C)=C1C(=O)NC1(C2)CC(C3)CC2CC3C1 FVMFGNBRCDDCPL-UHFFFAOYSA-N 0.000 claims 1
- UHFLHKZQPYROIV-UHFFFAOYSA-N n-(1-adamantyl)-2-(1-phenyltetrazol-5-yl)sulfanylacetamide Chemical compound C1C(C2)CC(C3)CC2CC13NC(=O)CSC1=NN=NN1C1=CC=CC=C1 UHFLHKZQPYROIV-UHFFFAOYSA-N 0.000 claims 1
- HGMLRIMTBLSJIM-UHFFFAOYSA-N n-(1-adamantyl)-2-(2-benzoyl-5-methoxyphenoxy)acetamide Chemical compound C1C(C2)CC(C3)CC2CC13NC(=O)COC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 HGMLRIMTBLSJIM-UHFFFAOYSA-N 0.000 claims 1
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- PHIREEBXEVROBM-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)-2-[[4-ethyl-5-(2-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC(=O)NC1=CC=CC(Cl)=C1C PHIREEBXEVROBM-UHFFFAOYSA-N 0.000 claims 1
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- PZXTZHMGBQTRIJ-UHFFFAOYSA-N n-(3-nitrophenyl)-2-[[4-(2-phenylethyl)-5-pyridin-4-yl-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound [O-][N+](=O)C1=CC=CC(NC(=O)CSC=2N(C(C=3C=CN=CC=3)=NN=2)CCC=2C=CC=CC=2)=C1 PZXTZHMGBQTRIJ-UHFFFAOYSA-N 0.000 claims 1
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- DCYRIDDVROEAFQ-UHFFFAOYSA-N n-(4-acetylphenyl)-2-[(5-benzyl-4-ethyl-1,2,4-triazol-3-yl)sulfanyl]acetamide Chemical compound N=1N=C(SCC(=O)NC=2C=CC(=CC=2)C(C)=O)N(CC)C=1CC1=CC=CC=C1 DCYRIDDVROEAFQ-UHFFFAOYSA-N 0.000 claims 1
- VSSIQNUQUMVFGU-UHFFFAOYSA-N n-(4-acetylphenyl)-2-[(5-cyclohexyl-4-ethyl-1,2,4-triazol-3-yl)sulfanyl]acetamide Chemical compound N=1N=C(C2CCCCC2)N(CC)C=1SCC(=O)NC1=CC=C(C(C)=O)C=C1 VSSIQNUQUMVFGU-UHFFFAOYSA-N 0.000 claims 1
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- BDGPKIHJGCXARV-UHFFFAOYSA-N n-(4-acetylphenyl)-2-[[4-ethyl-5-(2-methoxyphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1N=C(C=2C(=CC=CC=2)OC)N(CC)C=1SCC(=O)NC1=CC=C(C(C)=O)C=C1 BDGPKIHJGCXARV-UHFFFAOYSA-N 0.000 claims 1
- OSQJVDBWQTYHMW-UHFFFAOYSA-N n-(4-acetylphenyl)-2-[[4-ethyl-5-(3-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1N=C(C=2C=C(C)C=CC=2)N(CC)C=1SCC(=O)NC1=CC=C(C(C)=O)C=C1 OSQJVDBWQTYHMW-UHFFFAOYSA-N 0.000 claims 1
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- PXCUXXQQXFOWJK-UHFFFAOYSA-N n-(4-bromophenyl)-2-[(5-cyclohexyl-4-ethyl-1,2,4-triazol-3-yl)sulfanyl]acetamide Chemical compound N=1N=C(C2CCCCC2)N(CC)C=1SCC(=O)NC1=CC=C(Br)C=C1 PXCUXXQQXFOWJK-UHFFFAOYSA-N 0.000 claims 1
- MEPTZZXYZUSXJQ-UHFFFAOYSA-N n-(4-bromophenyl)-2-[[4-(2-phenylethyl)-5-pyridin-4-yl-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound C1=CC(Br)=CC=C1NC(=O)CSC(N1CCC=2C=CC=CC=2)=NN=C1C1=CC=NC=C1 MEPTZZXYZUSXJQ-UHFFFAOYSA-N 0.000 claims 1
- XCPOOVVFDXQBBU-UHFFFAOYSA-N n-(4-bromophenyl)-2-[[4-ethyl-5-[(4-fluoroanilino)methyl]-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1N=C(SCC(=O)NC=2C=CC(Br)=CC=2)N(CC)C=1CNC1=CC=C(F)C=C1 XCPOOVVFDXQBBU-UHFFFAOYSA-N 0.000 claims 1
- ZZAORWKXJHJAPB-UHFFFAOYSA-N n-(4-bromophenyl)-2-[[5-(2-bromophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1N=C(C=2C(=CC=CC=2)Br)N(CC)C=1SCC(=O)NC1=CC=C(Br)C=C1 ZZAORWKXJHJAPB-UHFFFAOYSA-N 0.000 claims 1
- VJEFEBDPMPLANV-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)-1-cyclohexyl-5-oxopyrrolidine-3-carboxamide Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(NC(=O)C2CC(=O)N(C3CCCCC3)C2)=C1 VJEFEBDPMPLANV-UHFFFAOYSA-N 0.000 claims 1
- HZFLRKOGPXAOAM-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)-2-[[4-methyl-5-(2-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound CC1=CC=CC=C1C(N1C)=NN=C1SCC(=O)NC1=CC=C(Cl)C([N+]([O-])=O)=C1 HZFLRKOGPXAOAM-UHFFFAOYSA-N 0.000 claims 1
- VMXWMXDCWYRQKH-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)-2-[[5-(4-chlorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC(=O)NC1=CC=C(Cl)C([N+]([O-])=O)=C1 VMXWMXDCWYRQKH-UHFFFAOYSA-N 0.000 claims 1
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- GKZIXEPSOLBANQ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[[4-ethyl-5-(3-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1N=C(C=2C=C(C)C=CC=2)N(CC)C=1SCC(=O)NC1=CC=C(Cl)C=C1 GKZIXEPSOLBANQ-UHFFFAOYSA-N 0.000 claims 1
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- QXZFEPADMBZLFG-UHFFFAOYSA-N n-[(3-hydroxyphenyl)methyl]-2-methyl-3-nitro-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound C1=CC=C([N+]([O-])=O)C(C)=C1C(=O)N(CC=1C=C(O)C=CC=1)CC1=CC=C(S(N)(=O)=O)C=C1 QXZFEPADMBZLFG-UHFFFAOYSA-N 0.000 claims 1
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- NRPVGZUSINBTMC-UHFFFAOYSA-N n-[(3-hydroxyphenyl)methyl]-n-[(4-propan-2-ylphenyl)methyl]heptanamide Chemical compound C=1C=CC(O)=CC=1CN(C(=O)CCCCCC)CC1=CC=C(C(C)C)C=C1 NRPVGZUSINBTMC-UHFFFAOYSA-N 0.000 claims 1
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- VOWHPZYBTLSKGE-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-n-[(4-hydroxyphenyl)methyl]-4-methylpentanamide Chemical compound C=1C=C(F)C=CC=1CN(C(=O)CCC(C)C)CC1=CC=C(O)C=C1 VOWHPZYBTLSKGE-UHFFFAOYSA-N 0.000 claims 1
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- CPFNJNJDMSVPFK-UHFFFAOYSA-N n-[(4-hydroxyphenyl)methyl]-n-(2-methylpropyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(CC(C)C)CC1=CC=C(O)C=C1 CPFNJNJDMSVPFK-UHFFFAOYSA-N 0.000 claims 1
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- ASANEODLTKPBTJ-UHFFFAOYSA-N n-[(4-hydroxyphenyl)methyl]-n-(3-methylbutyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(CCC(C)C)CC1=CC=C(O)C=C1 ASANEODLTKPBTJ-UHFFFAOYSA-N 0.000 claims 1
- ACTJJEUWBVIISW-UHFFFAOYSA-N n-[(4-hydroxyphenyl)methyl]-n-(3-propan-2-yloxypropyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(CCCOC(C)C)CC1=CC=C(O)C=C1 ACTJJEUWBVIISW-UHFFFAOYSA-N 0.000 claims 1
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- OYTJXXFVCAJCET-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-5-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-indole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CNC2=CC=C(C(=O)N3C4CC(CC(C)(C)C4)(C)C3)C=C12 OYTJXXFVCAJCET-UHFFFAOYSA-N 0.000 claims 1
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- HXHMFOCQKVNKSX-UHFFFAOYSA-N n-[(5-benzylsulfanyl-4-ethyl-1,2,4-triazol-3-yl)methyl]-4-chloroaniline Chemical compound N=1N=C(SCC=2C=CC=CC=2)N(CC)C=1CNC1=CC=C(Cl)C=C1 HXHMFOCQKVNKSX-UHFFFAOYSA-N 0.000 claims 1
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- YOYOWAJKBHTARZ-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)propyl]-5-(3,3,5-trimethyl-7-azabicyclo[3.2.1]octane-7-carbonyl)-1h-indole-3-carboxamide Chemical compound C1CN(C)CCN1CCCNC(=O)C1=CNC2=CC=C(C(=O)N3C4CC(CC(C)(C)C4)(C)C3)C=C12 YOYOWAJKBHTARZ-UHFFFAOYSA-N 0.000 claims 1
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- AXVKLGAEWBEFDB-UHFFFAOYSA-N n-[4-[[4-ethyl-5-(2-methylsulfanylpyridin-3-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]acetamide Chemical compound N=1N=C(C=2C(=NC=CC=2)SC)N(CC)C=1SCC1=CC=C(NC(C)=O)C=C1 AXVKLGAEWBEFDB-UHFFFAOYSA-N 0.000 claims 1
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- TXSPMALGFZQOHA-UHFFFAOYSA-N n-[4-[[4-ethyl-5-(5-methylthiophen-2-yl)-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]acetamide Chemical compound N=1N=C(C=2SC(C)=CC=2)N(CC)C=1SCC1=CC=C(NC(C)=O)C=C1 TXSPMALGFZQOHA-UHFFFAOYSA-N 0.000 claims 1
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- QTFZZTQNLNYSEX-UHFFFAOYSA-N n-[4-[[5-(1-benzothiophen-2-yl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]acetamide Chemical compound N=1N=C(C=2SC3=CC=CC=C3C=2)N(CC)C=1SCC1=CC=C(NC(C)=O)C=C1 QTFZZTQNLNYSEX-UHFFFAOYSA-N 0.000 claims 1
- GBNZHSRQJXVCGI-UHFFFAOYSA-N n-[4-[[5-(4-chlorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]phenyl]acetamide Chemical compound N=1N=C(C=2C=CC(Cl)=CC=2)N(CC)C=1SCC1=CC=C(NC(C)=O)C=C1 GBNZHSRQJXVCGI-UHFFFAOYSA-N 0.000 claims 1
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- FIGDPVVDJQSDSB-UHFFFAOYSA-N n-[5-[(2,4-dichlorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]-2,2-dimethylpropanamide Chemical compound S1C(NC(=O)C(C)(C)C)=NN=C1SCC1=CC=C(Cl)C=C1Cl FIGDPVVDJQSDSB-UHFFFAOYSA-N 0.000 claims 1
- XMPPBIXEZQVXGO-UHFFFAOYSA-N n-[5-[(2-fluorophenyl)methylsulfanylmethyl]-1,3,4-thiadiazol-2-yl]cyclohexanecarboxamide Chemical compound FC1=CC=CC=C1CSCC(S1)=NN=C1NC(=O)C1CCCCC1 XMPPBIXEZQVXGO-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (30)
| Application Number | Priority Date | Filing Date | Title |
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| DKPA200300567 | 2003-04-11 | ||
| DKPA200300565 | 2003-04-11 | ||
| DKPA200300569 | 2003-04-11 | ||
| DKPA200300570 | 2003-04-11 | ||
| DKPA200300571 | 2003-04-11 | ||
| DKPA200300566 | 2003-04-11 | ||
| US46745303P | 2003-05-02 | 2003-05-02 | |
| US46728403P | 2003-05-02 | 2003-05-02 | |
| US46736203P | 2003-05-02 | 2003-05-02 | |
| US46780003P | 2003-05-02 | 2003-05-02 | |
| US46743703P | 2003-05-02 | 2003-05-02 | |
| US46736303P | 2003-05-02 | 2003-05-02 | |
| DKPA200300776 | 2003-05-22 | ||
| DKPA200300777 | 2003-05-22 | ||
| US47442103P | 2003-05-30 | 2003-05-30 | |
| US47515703P | 2003-06-02 | 2003-06-02 | |
| DKPA200300972 | 2003-06-27 | ||
| DKPA200300990 | 2003-06-30 | ||
| DKPA200300989 | 2003-06-30 | ||
| DKPA200300988 | 2003-06-30 | ||
| DKPA200300998 | 2003-07-02 | ||
| US48607803P | 2003-07-10 | 2003-07-10 | |
| US48609503P | 2003-07-10 | 2003-07-10 | |
| US48609403P | 2003-07-10 | 2003-07-10 | |
| US48609703P | 2003-07-10 | 2003-07-10 | |
| US48609803P | 2003-07-10 | 2003-07-10 | |
| DKPA200301910 | 2003-12-22 | ||
| DKPA200400009 | 2004-01-06 | ||
| US53709904P | 2004-01-16 | 2004-01-16 | |
| PCT/DK2004/000254 WO2004089416A2 (en) | 2003-04-11 | 2004-04-06 | Combination of an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent |
Publications (2)
| Publication Number | Publication Date |
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| JP2006522750A true JP2006522750A (ja) | 2006-10-05 |
| JP2006522750A5 JP2006522750A5 (https=) | 2007-05-24 |
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| JP2006504357A Pending JP2006522750A (ja) | 2003-04-11 | 2004-04-06 | 代謝性症候群ならびに関連の疾患および障害を治療するために、11β−ヒドロキシステロイドデヒドロゲナーゼ1型阻害剤および抗高血圧剤を使用する併用療法 |
Country Status (2)
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| JP (1) | JP2006522750A (https=) |
| WO (1) | WO2004089416A2 (https=) |
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| JP2010513337A (ja) * | 2006-12-21 | 2010-04-30 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 選択的11β−HSD1阻害剤としての2−アダマンチル−ブチルアミド誘導体 |
| JP2011510046A (ja) * | 2008-01-25 | 2011-03-31 | ロディア オペレーションズ | エステルアミドの溶剤としての使用、新規のエステルアミド及びエステルアミドの製造方法 |
| JP2015155410A (ja) * | 2008-10-28 | 2015-08-27 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | アルデヒドデヒドロゲナーゼのモジュレーターおよびその使用方法 |
| JP2016512825A (ja) * | 2013-03-15 | 2016-05-09 | シファ・バイオメディカル・コーポレイションShifa Biomedical Corporation | 抗プロタンパク質転換酵素サブチリシン/ケキシン9型(抗pcsk9)化合物および心血管疾患の治療および/または予防におけるその使用方法 |
| JP2020514323A (ja) * | 2017-02-06 | 2020-05-21 | ケース ウエスタン リザーブ ユニバーシティ | 短鎖デヒドロゲナーゼ活性を調節する組成物と方法 |
| JP2022524290A (ja) * | 2019-01-31 | 2022-05-02 | 杏林製薬株式会社 | 15-pgdh阻害薬 |
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| DE602005017159D1 (de) | 2004-08-30 | 2009-11-26 | Janssen Pharmaceutica Nv | Oxysteroid-dehydrogenase-inhibitoren |
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| WO2004089416A2 (en) | 2004-10-21 |
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