JP2020533345A5 - - Google Patents
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- JP2020533345A5 JP2020533345A5 JP2020514550A JP2020514550A JP2020533345A5 JP 2020533345 A5 JP2020533345 A5 JP 2020533345A5 JP 2020514550 A JP2020514550 A JP 2020514550A JP 2020514550 A JP2020514550 A JP 2020514550A JP 2020533345 A5 JP2020533345 A5 JP 2020533345A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- carboxamide
- biphenyl
- triazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 description 49
- 150000003839 salts Chemical class 0.000 description 38
- 125000000217 alkyl group Chemical group 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- -1 2- (4'-(5-methyl-1,3,4-oxadiazole-2-yl)-[1,1'-biphenyl] -4-yl) propane Chemical compound 0.000 description 11
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000008194 pharmaceutical composition Substances 0.000 description 10
- 230000037361 pathway Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000003102 growth factor Substances 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- 125000001475 halogen functional group Chemical group 0.000 description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 4
- 150000003857 carboxamides Chemical class 0.000 description 4
- 230000001737 promoting effect Effects 0.000 description 4
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 description 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 3
- 108091007960 PI3Ks Proteins 0.000 description 3
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 3
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000004452 carbocyclyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229940127557 pharmaceutical product Drugs 0.000 description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 2
- 206010011878 Deafness Diseases 0.000 description 2
- 206010056677 Nerve degeneration Diseases 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000010370 hearing loss Effects 0.000 description 2
- 231100000888 hearing loss Toxicity 0.000 description 2
- 208000016354 hearing loss disease Diseases 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 201000000585 muscular atrophy Diseases 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000000451 tissue damage Effects 0.000 description 2
- 231100000827 tissue damage Toxicity 0.000 description 2
- 230000017423 tissue regeneration Effects 0.000 description 2
- 230000029663 wound healing Effects 0.000 description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 description 1
- SJCDBQHCQSIZHN-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxamide Chemical compound NC(=O)N1NNC=C1 SJCDBQHCQSIZHN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- RQDHRCQCMXSNMW-UHFFFAOYSA-N 1-[4-[2-[4-[4-(3-aminooxetan-3-yl)phenyl]phenyl]propan-2-yl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound NC1(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 RQDHRCQCMXSNMW-UHFFFAOYSA-N 0.000 description 1
- VZQBWUIZZMLGFJ-UHFFFAOYSA-N 1-[4-[2-[4-[4-(dimethylcarbamoyl)phenyl]phenyl]propan-2-yl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound CN(C(=O)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)C VZQBWUIZZMLGFJ-UHFFFAOYSA-N 0.000 description 1
- NZAIOLKRAKMHDD-UHFFFAOYSA-N 1-[4-[2-[4-[4-(dimethylsulfamoyl)phenyl]phenyl]propan-2-yl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound CN(S(=O)(=O)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)C NZAIOLKRAKMHDD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- QYSAYIHDNAXGPX-UHFFFAOYSA-N 1-[4-[[4-[1-[2-(dimethylamino)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound CN(CC(=O)N1CCC(=CC1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1)C QYSAYIHDNAXGPX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- DEBQGEQBYPYZOT-UHFFFAOYSA-N 1-[4-[[4-[4-(2-hydroxyethylsulfonyl)phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OCCS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N DEBQGEQBYPYZOT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- OITYOSLBKDWKRE-UHFFFAOYSA-N 1-[4-[[4-[4-(azetidin-1-ylmethyl)phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound N1(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N OITYOSLBKDWKRE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- DOAHUVPBNSOBEN-UHFFFAOYSA-N 1-[4-[[4-[4-[(2-hydroxyethylamino)methyl]phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OCCNCC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N DOAHUVPBNSOBEN-UHFFFAOYSA-N 0.000 description 1
- MEYLWXUVPRRFNP-UHFFFAOYSA-N 1-[4-[[4-[4-[(3,3-difluoroazetidin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound FC1(CN(C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)F MEYLWXUVPRRFNP-UHFFFAOYSA-N 0.000 description 1
- UWMZMNICHORDAV-UHFFFAOYSA-N 1-[4-[[4-[4-[(3,3-difluoropiperidin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound FC1(CN(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)F UWMZMNICHORDAV-UHFFFAOYSA-N 0.000 description 1
- SVRAWVADXBURIK-UHFFFAOYSA-N 1-[4-[[4-[4-[(3,3-difluoropyrrolidin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound FC1(CN(CC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)F SVRAWVADXBURIK-UHFFFAOYSA-N 0.000 description 1
- BBPQYQFRYMXKLQ-UHFFFAOYSA-N 1-[4-[[4-[4-[(3,3-dimethylpiperazin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound CC1(CN(CCN1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)C BBPQYQFRYMXKLQ-UHFFFAOYSA-N 0.000 description 1
- DNLWPTSGGUBEOY-UHFFFAOYSA-N 1-[4-[[4-[4-[(3,3-dimethylpyrrolidin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound CC1(CN(CC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)C DNLWPTSGGUBEOY-UHFFFAOYSA-N 0.000 description 1
- PTVQBZQLUJXWAJ-UHFFFAOYSA-N 1-[4-[[4-[4-[(3,4-dihydroxypyrrolidin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC1CN(CC1O)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N PTVQBZQLUJXWAJ-UHFFFAOYSA-N 0.000 description 1
- CFXDFRFIUWJYNJ-UHFFFAOYSA-N 1-[4-[[4-[4-[(3,5-dimethylpiperazin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound CC1CN(CC(N1)C)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N CFXDFRFIUWJYNJ-UHFFFAOYSA-N 0.000 description 1
- XYMROYGMKGIHAK-UHFFFAOYSA-N 1-[4-[[4-[4-[(3-fluoropiperidin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound FC1CN(CCC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N XYMROYGMKGIHAK-UHFFFAOYSA-N 0.000 description 1
- WJRZSNQURVSISH-UHFFFAOYSA-N 1-[4-[[4-[4-[(3-fluoropyrrolidin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound FC1CN(CC1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N WJRZSNQURVSISH-UHFFFAOYSA-N 0.000 description 1
- AWMJXERBUDRDKG-UHFFFAOYSA-N 1-[4-[[4-[4-[(3-hydroxy-3-methylazetidin-1-yl)methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OC1(CN(C1)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N)C AWMJXERBUDRDKG-UHFFFAOYSA-N 0.000 description 1
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| US20070191371A1 (en) | 2006-02-14 | 2007-08-16 | Kalypsys, Inc. | Heterocyclic modulators of ppar |
| US20090318410A1 (en) | 2006-10-30 | 2009-12-24 | Novartis Ag | Imidazopyridazines as lipid kinase inhibitors |
| 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 |
| JP2015524483A (ja) * | 2012-08-09 | 2015-08-24 | ニューロポア セラピーズ，インコーポレイティド | Ｐｉ３−キナーゼシグナリング経路の調節因子としてのアリール及びヘテロアリールで置換されたベンゼン誘導体 |
| WO2015056180A1 (en) | 2013-10-15 | 2015-04-23 | Glaxosmithkline Intellectual Property (No.2) Limited | Indoline derivatives as inhibitors of perk |
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