JP7394747B2 - ジフェニル誘導体及びその使用 - Google Patents
ジフェニル誘導体及びその使用 Download PDFInfo
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- JP7394747B2 JP7394747B2 JP2020514550A JP2020514550A JP7394747B2 JP 7394747 B2 JP7394747 B2 JP 7394747B2 JP 2020514550 A JP2020514550 A JP 2020514550A JP 2020514550 A JP2020514550 A JP 2020514550A JP 7394747 B2 JP7394747 B2 JP 7394747B2
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- Prior art keywords
- methyl
- phenyl
- carboxamide
- biphenyl
- triazole
- Prior art date
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- 125000006267 biphenyl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 781
- 150000003839 salts Chemical class 0.000 claims description 751
- 125000000217 alkyl group Chemical group 0.000 claims description 221
- 239000000203 mixture Substances 0.000 claims description 173
- 238000002360 preparation method Methods 0.000 claims description 137
- 229910052799 carbon Inorganic materials 0.000 claims description 113
- 125000000623 heterocyclic group Chemical group 0.000 claims description 105
- 239000008194 pharmaceutical composition Substances 0.000 claims description 76
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 60
- 239000003814 drug Substances 0.000 claims description 57
- 239000003102 growth factor Substances 0.000 claims description 47
- 230000037361 pathway Effects 0.000 claims description 47
- 230000001737 promoting effect Effects 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 230000029663 wound healing Effects 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 27
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 24
- 206010028289 Muscle atrophy Diseases 0.000 claims description 21
- 201000000585 muscular atrophy Diseases 0.000 claims description 21
- 206010011878 Deafness Diseases 0.000 claims description 20
- 230000007850 degeneration Effects 0.000 claims description 20
- 230000010370 hearing loss Effects 0.000 claims description 20
- 231100000888 hearing loss Toxicity 0.000 claims description 20
- 208000016354 hearing loss disease Diseases 0.000 claims description 20
- 230000020763 muscle atrophy Effects 0.000 claims description 20
- 230000004770 neurodegeneration Effects 0.000 claims description 20
- 210000002027 skeletal muscle Anatomy 0.000 claims description 20
- 150000003857 carboxamides Chemical class 0.000 claims description 19
- 210000000056 organ Anatomy 0.000 claims description 19
- 230000017423 tissue regeneration Effects 0.000 claims description 19
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims description 18
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 230000000451 tissue damage Effects 0.000 claims description 18
- 231100000827 tissue damage Toxicity 0.000 claims description 18
- 108091007960 PI3Ks Proteins 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 230000003213 activating effect Effects 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- YTCICUNNDUXOFZ-UHFFFAOYSA-N 5-methyl-1-[4-[2-[4-[4-(pyrrolidin-1-ylmethyl)phenyl]phenyl]propan-2-yl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C1=CC=C(C=C1)CN1CCCC1)C(=O)N YTCICUNNDUXOFZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- DBSMXZFYDNXILM-UHFFFAOYSA-N 1-methylpyrazole-3-carboxamide Chemical compound CN1C=CC(C(N)=O)=N1 DBSMXZFYDNXILM-UHFFFAOYSA-N 0.000 claims description 8
- RGLYOXKDGVQLKL-UHFFFAOYSA-N 5-methyl-1-[4-[[4-(1-methylpyrrolidin-3-yl)phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1CN(CC1)C)C(=O)N RGLYOXKDGVQLKL-UHFFFAOYSA-N 0.000 claims description 8
- STRFXIKETAJZNO-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[6-(piperazin-1-ylmethyl)pyridin-3-yl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1C=NC(=CC=1)CN1CCNCC1)C(=O)N STRFXIKETAJZNO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
- JUWKXPXVNRBHSQ-UHFFFAOYSA-N 1-[4-(6H-benzo[c]chromen-3-ylmethyl)phenyl]-5-methylpyrazole-3-carboxamide Chemical compound C1=C2C3=C(COC2=CC(=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N)C=CC=C3 JUWKXPXVNRBHSQ-UHFFFAOYSA-N 0.000 claims description 7
- GOMJAHNSCJDHPG-NDEPHWFRSA-N 1-[4-[[4-[4-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC[C@H]1N(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N GOMJAHNSCJDHPG-NDEPHWFRSA-N 0.000 claims description 7
- GOMJAHNSCJDHPG-UHFFFAOYSA-N 1-[4-[[4-[4-[[2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OCC1N(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N GOMJAHNSCJDHPG-UHFFFAOYSA-N 0.000 claims description 7
- FLSKEMPQAOXGGL-UHFFFAOYSA-N 1-[4-[[4-[5-(2-hydroxypropan-2-yl)pyridin-2-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC(C)(C)C=1C=CC(=NC=1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 FLSKEMPQAOXGGL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- IPUGUGOYXJDUPU-UHFFFAOYSA-N 1-[4-[2-[4-[4-[3-(aminomethyl)oxetan-3-yl]phenyl]phenyl]propan-2-yl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound NCC1(COC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N IPUGUGOYXJDUPU-UHFFFAOYSA-N 0.000 claims description 6
- ZOLRRIPWXDETAM-UHFFFAOYSA-N 1-[4-[[4-[2-(2-hydroxypropan-2-yl)pyridin-4-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC(C)(C)C1=NC=CC(=C1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 ZOLRRIPWXDETAM-UHFFFAOYSA-N 0.000 claims description 6
- JTUJFYPCGOKTLW-UHFFFAOYSA-N 1-[4-[[4-[4-[2-[(2-hydroxy-2-methylpropyl)amino]propan-2-yl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC(CNC(C)(C)C1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)(C)C JTUJFYPCGOKTLW-UHFFFAOYSA-N 0.000 claims description 6
- FHIVJAIZSVDBRU-UHFFFAOYSA-N 1-[4-[[4-[5-(2-hydroxypropan-2-yl)-6-methylpyridin-2-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC(C)(C)C=1C=CC(=NC=1C)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 FHIVJAIZSVDBRU-UHFFFAOYSA-N 0.000 claims description 6
- NCWPTVGMPVPCKA-UHFFFAOYSA-N 1-[4-[[4-[6-(3-hydroxyoxetan-3-yl)pyridin-3-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC1(COC1)C1=CC=C(C=N1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 NCWPTVGMPVPCKA-UHFFFAOYSA-N 0.000 claims description 6
- QNABIAVEPNBNRO-UHFFFAOYSA-N 5-methyl-1-[4-[2-(4-pyridin-2-ylphenyl)propan-2-yl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C1=NC=CC=C1)C(=O)N QNABIAVEPNBNRO-UHFFFAOYSA-N 0.000 claims description 6
- WSZBLEJBFHWZJS-UHFFFAOYSA-N 5-methyl-1-[4-[2-[4-(4-morpholin-4-ylcyclohexen-1-yl)phenyl]propan-2-yl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C=1CCC(CC=1)N1CCOCC1)C(=O)N WSZBLEJBFHWZJS-UHFFFAOYSA-N 0.000 claims description 6
- XMXNTNOBXVRTGM-UHFFFAOYSA-N 5-methyl-1-[4-[2-[4-[4-(pyrrolidin-1-ylmethyl)phenyl]phenyl]propan-2-yl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C1=CC=C(C=C1)CN1CCCC1)C(=O)N XMXNTNOBXVRTGM-UHFFFAOYSA-N 0.000 claims description 6
- GJNNVSFIKQZPTR-UHFFFAOYSA-N 5-methyl-1-[4-[[4-(1-methylpiperidin-4-yl)phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1CCN(CC1)C)C(=O)N GJNNVSFIKQZPTR-UHFFFAOYSA-N 0.000 claims description 6
- WDTDCUXOYBGINY-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(1-methylpyrrolidin-3-yl)oxyphenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)OC1CN(CC1)C)C(=O)N WDTDCUXOYBGINY-UHFFFAOYSA-N 0.000 claims description 6
- JPBJANAKZHMXTO-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(piperazine-1-carbonyl)phenyl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)N1CCNCC1)C(=O)N JPBJANAKZHMXTO-UHFFFAOYSA-N 0.000 claims description 6
- GWHAQVBBLRZAAA-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(pyrrolidin-1-ylmethyl)phenyl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CN1CCCC1)C(=O)N GWHAQVBBLRZAAA-UHFFFAOYSA-N 0.000 claims description 6
- LXKKNMIXYTWMAS-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[5-(piperazine-1-carbonyl)pyridin-2-yl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=NC=C(C=C1)C(=O)N1CCNCC1)C(=O)N LXKKNMIXYTWMAS-UHFFFAOYSA-N 0.000 claims description 6
- HGBFQHFQTQBDHO-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[6-(piperazine-1-carbonyl)pyridin-3-yl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1C=NC(=CC=1)C(=O)N1CCNCC1)C(=O)N HGBFQHFQTQBDHO-UHFFFAOYSA-N 0.000 claims description 6
- FEQKMECBDQMGGD-IBGZPJMESA-N 5-methyl-1-[4-[[4-[6-[[(3S)-3-methylpiperazin-1-yl]methyl]pyridin-3-yl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1C=NC(=CC=1)CN1C[C@@H](NCC1)C)C(=O)N FEQKMECBDQMGGD-IBGZPJMESA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 claims description 5
- KAXYUIACJONUCH-UHFFFAOYSA-N 1-[4-[2-(4-chlorophenyl)propan-2-yl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N KAXYUIACJONUCH-UHFFFAOYSA-N 0.000 claims description 5
- XQEVEEDPXWFWFM-UHFFFAOYSA-N 1-[4-[2-[4-(4-hydroxycyclohexen-1-yl)phenyl]propan-2-yl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC1CCC(=CC1)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N XQEVEEDPXWFWFM-UHFFFAOYSA-N 0.000 claims description 5
- OVCYKANXQIAMNU-UHFFFAOYSA-N 1-[4-[2-[4-[4-(1-amino-2,2,2-trifluoroethyl)phenyl]phenyl]propan-2-yl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound NC(C(F)(F)F)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N OVCYKANXQIAMNU-UHFFFAOYSA-N 0.000 claims description 5
- MYZDNJQPBPZKDW-UHFFFAOYSA-N 1-[4-[[4-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OCC(C)(C)C1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N MYZDNJQPBPZKDW-UHFFFAOYSA-N 0.000 claims description 5
- MLTUTMDKHQJFPC-UHFFFAOYSA-N 1-[4-[[4-[4-[(2-hydroxy-2-methylpropyl)sulfamoyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC(CNS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)(C)C MLTUTMDKHQJFPC-UHFFFAOYSA-N 0.000 claims description 5
- DROBUYPBFWBCMQ-AREMUKBSSA-N 1-[4-[[4-[4-[(3R)-3-(hydroxymethyl)piperazine-1-carbonyl]phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC[C@H]1CN(CCN1)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N DROBUYPBFWBCMQ-AREMUKBSSA-N 0.000 claims description 5
- GOMJAHNSCJDHPG-MUUNZHRXSA-N 1-[4-[[4-[4-[[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC[C@@H]1N(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N GOMJAHNSCJDHPG-MUUNZHRXSA-N 0.000 claims description 5
- PRMVQLBAAQMAFQ-HHHXNRCGSA-N 1-[4-[[4-[4-[[(2R)-4,4-difluoro-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound FC1(C[C@@H](N(C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N)CO)F PRMVQLBAAQMAFQ-HHHXNRCGSA-N 0.000 claims description 5
- VWBLEIYDNDMWKE-UHFFFAOYSA-N 1-[4-[[4-[5-(1-hydroxy-2-methylpropan-2-yl)pyridin-2-yl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OCC(C)(C)C=1C=CC(=NC=1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(N=C2C)C(=O)N)C=C1 VWBLEIYDNDMWKE-UHFFFAOYSA-N 0.000 claims description 5
- GKHCALANTAWMHZ-UHFFFAOYSA-N 1-[4-[[4-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC(C)(C)C1=CC=C(C=N1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(N=C2C)C(=O)N)C=C1 GKHCALANTAWMHZ-UHFFFAOYSA-N 0.000 claims description 5
- HALUSEIYAGYWMY-UHFFFAOYSA-N 5-methyl-1-[4-[(4-pyridin-3-ylphenyl)methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1C=NC=CC=1)C(=O)N HALUSEIYAGYWMY-UHFFFAOYSA-N 0.000 claims description 5
- XFHIYOWUJOXEDE-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[2-(1-methylpiperidin-4-yl)ethynyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C#CC1CCN(CC1)C)C(=O)N XFHIYOWUJOXEDE-UHFFFAOYSA-N 0.000 claims description 5
- IGSSQHFKVHRTNF-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(2-oxa-7-azaspiro[3.4]octan-7-ylmethyl)phenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound C1OCC11CN(CC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N IGSSQHFKVHRTNF-UHFFFAOYSA-N 0.000 claims description 5
- OTFWTWOGALFHJS-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(piperazin-1-ylmethyl)phenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CN1CCNCC1)C(=O)N OTFWTWOGALFHJS-UHFFFAOYSA-N 0.000 claims description 5
- TUKYQKYMGWDXMK-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(piperazine-1-carbonyl)phenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)N1CCNCC1)C(=O)N TUKYQKYMGWDXMK-UHFFFAOYSA-N 0.000 claims description 5
- WDTDCUXOYBGINY-SANMLTNESA-N 5-methyl-1-[4-[[4-[4-[(3S)-1-methylpyrrolidin-3-yl]oxyphenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)O[C@@H]1CN(CC1)C)C(=O)N WDTDCUXOYBGINY-SANMLTNESA-N 0.000 claims description 5
- FPLYCJURGXXYKZ-IBGZPJMESA-N 5-methyl-1-[4-[[4-[4-[(3S)-3-methylpiperazine-1-carbonyl]phenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)N1C[C@@H](NCC1)C)C(=O)N FPLYCJURGXXYKZ-IBGZPJMESA-N 0.000 claims description 5
- MRVJARZWGPQLJK-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CN1CCN(CC1)C)C(=O)N MRVJARZWGPQLJK-UHFFFAOYSA-N 0.000 claims description 5
- WYCNISOCNLYRGT-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[5-(piperazin-1-ylmethyl)pyridin-2-yl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=NC=C(C=C1)CN1CCNCC1)C(=O)N WYCNISOCNLYRGT-UHFFFAOYSA-N 0.000 claims description 5
- XVGWIEFKFDMPAV-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[5-(piperazin-1-ylmethyl)pyridin-2-yl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=NC=C(C=C1)CN1CCNCC1)C(=O)N XVGWIEFKFDMPAV-UHFFFAOYSA-N 0.000 claims description 5
- XDGYFUYWBZXGEH-UHFFFAOYSA-N 6-[4-[[4-(3-carbamoyl-5-methylpyrazol-1-yl)phenyl]methyl]phenyl]-N-(2-hydroxy-2-methylpropyl)pyridine-3-carboxamide Chemical compound C(N)(=O)C1=NN(C(=C1)C)C1=CC=C(CC2=CC=C(C=C2)C2=NC=C(C(=O)NCC(C)(C)O)C=C2)C=C1 XDGYFUYWBZXGEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- MJKCVZRNXUJWBR-UHFFFAOYSA-N 1-[4-[2-(4-isoquinolin-7-ylphenyl)propan-2-yl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound C1=NC=CC2=CC=C(C=C12)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N MJKCVZRNXUJWBR-UHFFFAOYSA-N 0.000 claims description 4
- DSPVTXXBMLBJQD-UHFFFAOYSA-N 1-[4-[2-[4-(1H-indazol-5-yl)phenyl]propan-2-yl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound N1N=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N DSPVTXXBMLBJQD-UHFFFAOYSA-N 0.000 claims description 4
- PCOHELUPPYTZFL-UHFFFAOYSA-N 1-[4-[2-[4-(2-aminopyridin-4-yl)phenyl]propan-2-yl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound NC1=NC=CC(=C1)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N PCOHELUPPYTZFL-UHFFFAOYSA-N 0.000 claims description 4
- WGKSHADIVBMDBG-UHFFFAOYSA-N 1-[4-[[4-(2,3-dihydro-1H-isoindol-5-yl)phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound C1NCC2=CC(=CC=C12)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 WGKSHADIVBMDBG-UHFFFAOYSA-N 0.000 claims description 4
- ZPQCLFUREXPUKH-UHFFFAOYSA-N 1-[4-[[4-[2-(1-hydroxycyclohexyl)ethynyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC1(CCCCC1)C#CC1=CC=C(CC2=CC=C(C=C2)N2N=C(N=C2C)C(=O)N)C=C1 ZPQCLFUREXPUKH-UHFFFAOYSA-N 0.000 claims description 4
- DEWQPHULDQIGEP-UHFFFAOYSA-N 1-[4-[[4-[2-(2-hydroxypropan-2-yl)pyrimidin-5-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC(C)(C)C1=NC=C(C=N1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 DEWQPHULDQIGEP-UHFFFAOYSA-N 0.000 claims description 4
- QVINNGZQWAPOAB-UHFFFAOYSA-N 1-[4-[[4-[2-(hydroxymethyl)pyridin-4-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OCC1=NC=CC(=C1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 QVINNGZQWAPOAB-UHFFFAOYSA-N 0.000 claims description 4
- QJMDUPNBCBWBQI-UHFFFAOYSA-N 1-[4-[[4-[2-[(dimethylamino)methyl]pyridin-4-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound CN(C)CC1=NC=CC(=C1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 QJMDUPNBCBWBQI-UHFFFAOYSA-N 0.000 claims description 4
- LNTCYPATJIPZRZ-UHFFFAOYSA-N 1-[4-[[4-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC(C)(C)C1CCN(CC1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(N=C2C)C(=O)N)C=C1 LNTCYPATJIPZRZ-UHFFFAOYSA-N 0.000 claims description 4
- NCYZLMYWZYTCQM-UHFFFAOYSA-N 1-[4-[[4-[4-(2-hydroxypropan-2-yl)pyridin-2-yl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC(C)(C)C1=CC(=NC=C1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(N=C2C)C(=O)N)C=C1 NCYZLMYWZYTCQM-UHFFFAOYSA-N 0.000 claims description 4
- KGSLDVHIPILEPN-UHFFFAOYSA-N 1-[4-[[4-[4-(azetidin-3-ylcarbamoyl)phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound N1CC(C1)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N KGSLDVHIPILEPN-UHFFFAOYSA-N 0.000 claims description 4
- OPEBBNOTVKZRLN-UHFFFAOYSA-N 1-[4-[[4-[4-(diethylaminomethyl)phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound C(C)N(CC)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N OPEBBNOTVKZRLN-UHFFFAOYSA-N 0.000 claims description 4
- DTHOUUTYDUBWLQ-UHFFFAOYSA-N 1-[4-[[4-[4-[(2-hydroxy-2-methylpropyl)carbamoyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC(CNC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)(C)C DTHOUUTYDUBWLQ-UHFFFAOYSA-N 0.000 claims description 4
- HCCJCKBXKZRENW-HHHXNRCGSA-N 1-[4-[[4-[4-[[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC[C@@H]1N(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N HCCJCKBXKZRENW-HHHXNRCGSA-N 0.000 claims description 4
- HCCJCKBXKZRENW-MHZLTWQESA-N 1-[4-[[4-[4-[[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC[C@H]1N(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N HCCJCKBXKZRENW-MHZLTWQESA-N 0.000 claims description 4
- HCCJCKBXKZRENW-UHFFFAOYSA-N 1-[4-[[4-[4-[[2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OCC1N(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N HCCJCKBXKZRENW-UHFFFAOYSA-N 0.000 claims description 4
- MAGIZOAMWBXTOW-UHFFFAOYSA-N 1-[4-[[4-[4-[[4-[(dimethylamino)methyl]piperidin-1-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound CN(C)CC1CCN(CC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N MAGIZOAMWBXTOW-UHFFFAOYSA-N 0.000 claims description 4
- DAWVUCHVCOOLHH-UHFFFAOYSA-N 1-[4-[[4-[5-(1-hydroxy-2-methylpropan-2-yl)pyridin-2-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OCC(C)(C)C=1C=CC(=NC=1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 DAWVUCHVCOOLHH-UHFFFAOYSA-N 0.000 claims description 4
- QODPTSSCBOKYHC-UHFFFAOYSA-N 1-[4-[[4-[5-[(2-hydroxy-2-methylpropyl)sulfamoyl]pyridin-2-yl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC(CNS(=O)(=O)C=1C=CC(=NC=1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(N=C2C)C(=O)N)C=C1)(C)C QODPTSSCBOKYHC-UHFFFAOYSA-N 0.000 claims description 4
- PGGNFJJPAOAVRI-UHFFFAOYSA-N 1-[4-[[4-[5-[(dimethylamino)methyl]pyridin-3-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound CN(C)CC=1C=C(C=NC=1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 PGGNFJJPAOAVRI-UHFFFAOYSA-N 0.000 claims description 4
- RZYWRTUPWNYJGL-UHFFFAOYSA-N 1-[4-[[4-[6-(2-hydroxypropan-2-yl)pyridazin-3-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OC(C)(C)C1=CC=C(N=N1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 RZYWRTUPWNYJGL-UHFFFAOYSA-N 0.000 claims description 4
- DWJDFPYQWHJXAJ-UHFFFAOYSA-N 1-[4-[[4-[6-[(dimethylamino)methyl]pyridin-3-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound CN(C)CC1=CC=C(C=N1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 DWJDFPYQWHJXAJ-UHFFFAOYSA-N 0.000 claims description 4
- PTKUIJKEYWYTER-FQEVSTJZSA-N 1-[4-[[4-[6-[[(3S)-3,4-dimethylpiperazin-1-yl]methyl]pyridin-3-yl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound C[C@H]1CN(CCN1C)CC1=CC=C(C=N1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(N=C2C)C(=O)N)C=C1 PTKUIJKEYWYTER-FQEVSTJZSA-N 0.000 claims description 4
- KADUJZWTVNSKJR-UHFFFAOYSA-N 5-methyl-1-[4-[(4-pyridin-3-ylphenyl)methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1C=NC=CC=1)C(=O)N KADUJZWTVNSKJR-UHFFFAOYSA-N 0.000 claims description 4
- AWBWONUBRAEKDF-UHFFFAOYSA-N 5-methyl-1-[4-[(4-pyridin-4-ylphenyl)methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=NC=C1)C(=O)N AWBWONUBRAEKDF-UHFFFAOYSA-N 0.000 claims description 4
- RDLGLYUNVWWNEI-UHFFFAOYSA-N 5-methyl-1-[4-[2-(4-pyridin-4-ylphenyl)propan-2-yl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C1=CC=NC=C1)C(=O)N RDLGLYUNVWWNEI-UHFFFAOYSA-N 0.000 claims description 4
- VQDIZSUWMDZCBJ-UHFFFAOYSA-N 5-methyl-1-[4-[2-(4-quinolin-6-ylphenyl)propan-2-yl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C=1C=C2C=CC=NC2=CC=1)C(=O)N VQDIZSUWMDZCBJ-UHFFFAOYSA-N 0.000 claims description 4
- QLKIGZNMKZKRKZ-UHFFFAOYSA-N 5-methyl-1-[4-[2-(4-quinoxalin-6-ylphenyl)propan-2-yl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C=1C=C2N=CC=NC2=CC=1)C(=O)N QLKIGZNMKZKRKZ-UHFFFAOYSA-N 0.000 claims description 4
- IMYCJJXMZWPMHL-UHFFFAOYSA-N 5-methyl-1-[4-[2-(4-thiophen-3-ylphenyl)propan-2-yl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C1=CSC=C1)C(=O)N IMYCJJXMZWPMHL-UHFFFAOYSA-N 0.000 claims description 4
- FZKPFHJNEJKQKX-UHFFFAOYSA-N 5-methyl-1-[4-[2-[4-(6-pyrrolidin-1-ylpyridin-3-yl)phenyl]propan-2-yl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C=1C=NC(=CC=1)N1CCCC1)C(=O)N FZKPFHJNEJKQKX-UHFFFAOYSA-N 0.000 claims description 4
- FKODUAYZLXZLSA-UHFFFAOYSA-N 5-methyl-1-[4-[2-[4-[3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]phenyl]propan-2-yl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1OC(=NN=1)C)C(=O)N FKODUAYZLXZLSA-UHFFFAOYSA-N 0.000 claims description 4
- YNXJVJCODJPEDP-UHFFFAOYSA-N 5-methyl-1-[4-[[4-(1,2,3,4-tetrahydroisoquinolin-6-yl)phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1C=C2CCNCC2=CC=1)C(=O)N YNXJVJCODJPEDP-UHFFFAOYSA-N 0.000 claims description 4
- DOMNYDDPVCKSQD-UHFFFAOYSA-N 5-methyl-1-[4-[[4-(1-methyl-2,3,6,7-tetrahydroazepin-4-yl)phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1CCN(CCC=1)C)C(=O)N DOMNYDDPVCKSQD-UHFFFAOYSA-N 0.000 claims description 4
- LZGSLXPVVZTSGZ-UHFFFAOYSA-N 5-methyl-1-[4-[[4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1CCN(CC=1)C)C(=O)N LZGSLXPVVZTSGZ-UHFFFAOYSA-N 0.000 claims description 4
- BPGMFTQKVLCXQE-UHFFFAOYSA-N 5-methyl-1-[4-[[4-(2-methyl-1,3-dihydroisoindol-5-yl)phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1C=C2CN(CC2=CC=1)C)C(=O)N BPGMFTQKVLCXQE-UHFFFAOYSA-N 0.000 claims description 4
- DLMLBLQBHLPSSR-UHFFFAOYSA-N 5-methyl-1-[4-[[4-(2-methyl-3,4-dihydro-1H-isoquinolin-6-yl)phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C=1C=C2CCN(CC2=CC=1)C)C(=O)N DLMLBLQBHLPSSR-UHFFFAOYSA-N 0.000 claims description 4
- HSSFQGDRKVERBG-UHFFFAOYSA-N 5-methyl-1-[4-[[4-(4-methylsulfonylphenyl)phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)S(=O)(=O)C)C(=O)N HSSFQGDRKVERBG-UHFFFAOYSA-N 0.000 claims description 4
- RGLYOXKDGVQLKL-FQEVSTJZSA-N 5-methyl-1-[4-[[4-[(3R)-1-methylpyrrolidin-3-yl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)[C@@H]1CN(CC1)C)C(=O)N RGLYOXKDGVQLKL-FQEVSTJZSA-N 0.000 claims description 4
- RGLYOXKDGVQLKL-HXUWFJFHSA-N 5-methyl-1-[4-[[4-[(3S)-1-methylpyrrolidin-3-yl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)[C@H]1CN(CC1)C)C(=O)N RGLYOXKDGVQLKL-HXUWFJFHSA-N 0.000 claims description 4
- WOFCQNGULJZHJW-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[2-(piperazine-1-carbonyl)spiro[3.3]heptan-6-yl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1CC2(C1)CC(C2)C(=O)N1CCNCC1)C(=O)N WOFCQNGULJZHJW-UHFFFAOYSA-N 0.000 claims description 4
- AUUMBSWONRCIEO-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(1-methylpiperidin-4-yl)oxyphenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)OC1CCN(CC1)C)C(=O)N AUUMBSWONRCIEO-UHFFFAOYSA-N 0.000 claims description 4
- SHOAXBJISWSWFI-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(4-methylpiperazine-1-carbonyl)phenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)N1CCN(CC1)C)C(=O)N SHOAXBJISWSWFI-UHFFFAOYSA-N 0.000 claims description 4
- AKKUGLMALPCIBW-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(piperazine-1-carbonyl)-1-bicyclo[2.2.2]octanyl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C12CCC(CC1)(CC2)C(=O)N1CCNCC1)C(=O)N AKKUGLMALPCIBW-UHFFFAOYSA-N 0.000 claims description 4
- YWYBNHVIXMPORE-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(piperidin-1-ylmethyl)phenyl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CN1CCCCC1)C(=O)N YWYBNHVIXMPORE-UHFFFAOYSA-N 0.000 claims description 4
- KDBABRKESSURRC-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(pyrrolidin-1-ylmethyl)phenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CN1CCCC1)C(=O)N KDBABRKESSURRC-UHFFFAOYSA-N 0.000 claims description 4
- VQVGKHBNDWHCGR-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-[(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)methyl]phenyl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CN1CC2CN(CC2C1)C)C(=O)N VQVGKHBNDWHCGR-UHFFFAOYSA-N 0.000 claims description 4
- WDTDCUXOYBGINY-AREMUKBSSA-N 5-methyl-1-[4-[[4-[4-[(3R)-1-methylpyrrolidin-3-yl]oxyphenyl]phenyl]methyl]phenyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=NC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)O[C@H]1CN(CC1)C)C(=O)N WDTDCUXOYBGINY-AREMUKBSSA-N 0.000 claims description 4
- BQTSZYMXLOAGBQ-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[5-[[4-(oxetan-3-yl)piperazin-1-yl]methyl]pyridin-2-yl]phenyl]methyl]phenyl]pyrazole-3-carboxamide Chemical compound CC1=CC(=NN1C1=CC=C(C=C1)CC1=CC=C(C=C1)C1=NC=C(C=C1)CN1CCN(CC1)C1COC1)C(=O)N BQTSZYMXLOAGBQ-UHFFFAOYSA-N 0.000 claims description 4
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- IJWOERGPGGJTNE-UHFFFAOYSA-N 1-[4-[2-[4-(1,3-benzothiazol-5-yl)phenyl]propan-2-yl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound S1C=NC2=C1C=CC(=C2)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N IJWOERGPGGJTNE-UHFFFAOYSA-N 0.000 claims description 3
- DVWZXJTVCYGFTO-UHFFFAOYSA-N 1-[4-[2-[4-(6-cyanopyridin-3-yl)phenyl]propan-2-yl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound C(#N)C1=CC=C(C=N1)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N DVWZXJTVCYGFTO-UHFFFAOYSA-N 0.000 claims description 3
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- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
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- QUTVDBFBBLHQOQ-CQSZACIVSA-N tert-butyl (2R)-4-(4-bromobenzoyl)-2-(hydroxymethyl)piperazine-1-carboxylate Chemical compound BrC1=CC=C(C(=O)N2C[C@@H](N(CC2)C(=O)OC(C)(C)C)CO)C=C1 QUTVDBFBBLHQOQ-CQSZACIVSA-N 0.000 description 1
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- KLAKKXFTOLAYMZ-PGSZONDNSA-N tert-butyl (3aS,6aR)-5-[[4-[4-[[4-(3-carbamoyl-5-methyl-1,2,4-triazol-1-yl)phenyl]methyl]phenyl]phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate Chemical compound C(N)(=O)C1=NN(C(=N1)C)C1=CC=C(CC2=CC=C(C=C2)C2=CC=C(C=C2)CC2C[C@@H]3[C@@H](CN(C3)C(=O)OC(C)(C)C)C2)C=C1 KLAKKXFTOLAYMZ-PGSZONDNSA-N 0.000 description 1
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- IBUAXTZIYJJZNY-UHFFFAOYSA-N tert-butyl 3-[4-[[4-(3-carbamoyl-5-methylpyrazol-1-yl)phenyl]methyl]phenyl]-2,5-dihydropyrrole-1-carboxylate Chemical compound C(N)(=O)C1=NN(C(=C1)C)C1=CC=C(CC2=CC=C(C=C2)C=2CN(CC=2)C(=O)OC(C)(C)C)C=C1 IBUAXTZIYJJZNY-UHFFFAOYSA-N 0.000 description 1
- XZNDJVFOKCLBOM-UHFFFAOYSA-N tert-butyl 4-(6-bromopyridine-3-carbonyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C1=CC=C(Br)N=C1 XZNDJVFOKCLBOM-UHFFFAOYSA-N 0.000 description 1
- YNQYFEHGKDBSOZ-UHFFFAOYSA-N tert-butyl 4-[(5-chloropyridin-2-yl)methyl]piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(Cc2ccc(Cl)cn2)CC1 YNQYFEHGKDBSOZ-UHFFFAOYSA-N 0.000 description 1
- FRSBMSDJJXPARV-UHFFFAOYSA-N tert-butyl 4-[(6-chloropyridin-3-yl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=C(Cl)N=C1 FRSBMSDJJXPARV-UHFFFAOYSA-N 0.000 description 1
- KMIYLRPODAIKKG-UHFFFAOYSA-N tert-butyl 4-[4-[4-[[4-(3-carbamoyl-5-methyl-1,2,4-triazol-1-yl)phenyl]methyl]phenyl]benzoyl]piperazine-1-carboxylate Chemical compound C(N)(=O)C1=NN(C(=N1)C)C1=CC=C(CC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)C=C1 KMIYLRPODAIKKG-UHFFFAOYSA-N 0.000 description 1
- NRUJZFZNAHDFNU-UHFFFAOYSA-N tert-butyl 4-[4-[4-[[4-(3-carbamoyl-5-methylpyrazol-1-yl)phenyl]methyl]phenyl]benzoyl]piperazine-1-carboxylate Chemical compound C(N)(=O)C1=NN(C(=C1)C)C1=CC=C(CC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)C=C1 NRUJZFZNAHDFNU-UHFFFAOYSA-N 0.000 description 1
- JVPKZHNTEJTBNF-UHFFFAOYSA-N tert-butyl 4-[4-[4-[[4-(3-carbamoyl-5-methylpyrazol-1-yl)phenyl]methyl]phenyl]bicyclo[2.2.2]octane-1-carbonyl]piperazine-1-carboxylate Chemical compound C(N)(=O)C1=NN(C(=C1)C)C1=CC=C(CC2=CC=C(C=C2)C23CCC(CC2)(CC3)C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)C=C1 JVPKZHNTEJTBNF-UHFFFAOYSA-N 0.000 description 1
- SDLUZKDQIQDTRZ-UHFFFAOYSA-N tert-butyl 4-[4-[4-[[4-(3-ethoxycarbonyl-5-methylpyrazol-1-yl)phenyl]methyl]phenyl]bicyclo[2.2.2]octane-1-carbonyl]piperazine-1-carboxylate Chemical compound C(C)OC(=O)C1=NN(C(=C1)C)C1=CC=C(CC2=CC=C(C=C2)C23CCC(CC2)(CC3)C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)C=C1 SDLUZKDQIQDTRZ-UHFFFAOYSA-N 0.000 description 1
- MATLHGNTKDKPHC-UHFFFAOYSA-N tert-butyl 4-[5-[4-[[4-(3-carbamoyl-5-methylpyrazol-1-yl)phenyl]methyl]phenyl]pyridine-2-carbonyl]piperazine-1-carboxylate Chemical compound C(N)(=O)C1=NN(C(=C1)C)C1=CC=C(CC2=CC=C(C=C2)C=2C=CC(=NC=2)C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)C=C1 MATLHGNTKDKPHC-UHFFFAOYSA-N 0.000 description 1
- RAKRWPXYJWICJP-UHFFFAOYSA-N tert-butyl 4-[6-[4-[[4-(3-carbamoyl-5-methyl-1,2,4-triazol-1-yl)phenyl]methyl]phenyl]spiro[3.3]heptane-2-carbonyl]piperazine-1-carboxylate Chemical compound C(N)(=O)C1=NN(C(=N1)C)C1=CC=C(CC2=CC=C(C=C2)C2CC3(CC(C3)C(=O)N3CCN(CC3)C(=O)OC(C)(C)C)C2)C=C1 RAKRWPXYJWICJP-UHFFFAOYSA-N 0.000 description 1
- AAEYFMAHSYKHGD-UHFFFAOYSA-N tert-butyl 4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1 AAEYFMAHSYKHGD-UHFFFAOYSA-N 0.000 description 1
- HHWYECSRNZKPHB-UHFFFAOYSA-N tert-butyl 4-[[4-[4-[[4-(3-carbamoyl-5-methyl-1,2,4-triazol-1-yl)phenyl]methyl]phenyl]phenyl]methyl]piperazine-1-carboxylate Chemical compound C(N)(=O)C1=NN(C(=N1)C)C1=CC=C(CC2=CC=C(C=C2)C2=CC=C(C=C2)CN2CCN(CC2)C(=O)OC(C)(C)C)C=C1 HHWYECSRNZKPHB-UHFFFAOYSA-N 0.000 description 1
- INUWDZDWSJJFSQ-UHFFFAOYSA-N tert-butyl 4-ethynylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C#C)CC1 INUWDZDWSJJFSQ-UHFFFAOYSA-N 0.000 description 1
- GGNDIMLSSMWKDR-UHFFFAOYSA-N tert-butyl 5-oxo-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate Chemical compound C1C(=O)CC2CN(C(=O)OC(C)(C)C)CC21 GGNDIMLSSMWKDR-UHFFFAOYSA-N 0.000 description 1
- CNYRVWYUFCJIIU-UHFFFAOYSA-N tert-butyl N-[[3-[4-[4-[2-[4-(3-carbamoyl-5-methylpyrazol-1-yl)phenyl]propan-2-yl]phenyl]phenyl]oxetan-3-yl]methyl]carbamate Chemical compound C(N)(=O)C1=NN(C(=C1)C)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)C1=CC=C(C=C1)C1(COC1)CNC(OC(C)(C)C)=O CNYRVWYUFCJIIU-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000007838 tissue remodeling Effects 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
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- 230000002463 transducing effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000037314 wound repair Effects 0.000 description 1
- 229950000339 xinafoate Drugs 0.000 description 1
- ZQJYTTPJYLKTTI-UHFFFAOYSA-M zinc;2h-pyridin-2-ide;bromide Chemical compound Br[Zn+].C1=CC=N[C-]=C1 ZQJYTTPJYLKTTI-UHFFFAOYSA-M 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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| PCT/EP2018/074662 WO2019053090A1 (en) | 2017-09-13 | 2018-09-12 | DIPHENYL DERIVATIVES AND USES THEREOF |
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| JP2020533345A5 JP2020533345A5 (enExample) | 2021-10-21 |
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| CN111848552B (zh) * | 2019-04-28 | 2023-12-19 | 南京富润凯德生物医药有限公司 | 一种3-(取代苯基)氧杂环丁烷-3-羧酸及其中间体的制备方法及应用 |
| GB202003668D0 (en) * | 2020-03-13 | 2020-04-29 | Heptares Therapeutics Ltd | GPR52 Modulator compounds |
| AR121901A1 (es) | 2020-04-22 | 2022-07-20 | Neurocrine Biosciences Inc | Moduladores gpr52 y métodos de uso |
| WO2022232017A1 (en) * | 2021-04-26 | 2022-11-03 | Neurocrine Biosciences, Inc. | Gpr52 modulators and methods of use |
| GB202113186D0 (en) * | 2021-09-15 | 2021-10-27 | Heptares Therapeutics Ltd | GPR52 Modulator compounds |
Citations (3)
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|---|---|---|---|---|
| WO2006136823A1 (en) | 2005-06-21 | 2006-12-28 | Astex Therapeutics Limited | Heterocyclic containing amines as kinase b inhibitors |
| JP2010508314A (ja) | 2006-10-30 | 2010-03-18 | ノバルティス アーゲー | 脂質キナーゼ阻害剤としてのイミダゾピリダジン |
| WO2014026039A2 (en) | 2012-08-09 | 2014-02-13 | Neuropore Therapies, Inc. | Aryl-and heteroaryl-substituted benzene derivatives as modulators of pi3-kinase signalling pathways |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2520804A1 (en) | 2003-04-03 | 2004-10-28 | Merck & Co., Inc. | Biaryl substituted pyrazoles as sodium channel blockers |
| US20070191371A1 (en) | 2006-02-14 | 2007-08-16 | Kalypsys, Inc. | Heterocyclic modulators of ppar |
| TWI579274B (zh) | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備1-芳基-5-烷基吡唑化合物的改良方法 |
| JO3215B1 (ar) | 2012-08-09 | 2018-03-08 | Phenex Pharmaceuticals Ag | حلقات غير متجانسة بها 5 ذرات تحتوي على النيتروجين بها استبدال بكربوكساميد أو سلفوناميد كمعدلات لمستقبل نووي غير محمي RORy |
| WO2015056180A1 (en) | 2013-10-15 | 2015-04-23 | Glaxosmithkline Intellectual Property (No.2) Limited | Indoline derivatives as inhibitors of perk |
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- 2018-09-12 EP EP18769353.6A patent/EP3681883B1/en active Active
- 2018-09-12 WO PCT/EP2018/074662 patent/WO2019053090A1/en not_active Ceased
- 2018-09-12 ES ES18769353T patent/ES2985747T3/es active Active
- 2018-09-12 US US16/129,199 patent/US10633350B2/en active Active
- 2018-09-13 UY UY0001037872A patent/UY37872A/es not_active Application Discontinuation
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006136823A1 (en) | 2005-06-21 | 2006-12-28 | Astex Therapeutics Limited | Heterocyclic containing amines as kinase b inhibitors |
| JP2010508314A (ja) | 2006-10-30 | 2010-03-18 | ノバルティス アーゲー | 脂質キナーゼ阻害剤としてのイミダゾピリダジン |
| WO2014026039A2 (en) | 2012-08-09 | 2014-02-13 | Neuropore Therapies, Inc. | Aryl-and heteroaryl-substituted benzene derivatives as modulators of pi3-kinase signalling pathways |
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| EP3681883B1 (en) | 2024-02-21 |
| TW201920112A (zh) | 2019-06-01 |
| CN111094278B (zh) | 2023-07-14 |
| CN111094278A (zh) | 2020-05-01 |
| ES2985747T3 (es) | 2024-11-07 |
| EP3681883A1 (en) | 2020-07-22 |
| WO2019053090A1 (en) | 2019-03-21 |
| US10633350B2 (en) | 2020-04-28 |
| JP2020533345A (ja) | 2020-11-19 |
| UY37872A (es) | 2019-04-30 |
| US20190077773A1 (en) | 2019-03-14 |
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