TW201920112A - 二苯基衍生物及其用途 - Google Patents
二苯基衍生物及其用途 Download PDFInfo
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- TW201920112A TW201920112A TW107132228A TW107132228A TW201920112A TW 201920112 A TW201920112 A TW 201920112A TW 107132228 A TW107132228 A TW 107132228A TW 107132228 A TW107132228 A TW 107132228A TW 201920112 A TW201920112 A TW 201920112A
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- Prior art keywords
- methyl
- phenyl
- carboxamide
- biphenyl
- compound
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- 125000006267 biphenyl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 1058
- 150000003839 salts Chemical class 0.000 claims abstract description 755
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 62
- 239000003102 growth factor Substances 0.000 claims abstract description 40
- 230000037361 pathway Effects 0.000 claims abstract description 38
- 230000029663 wound healing Effects 0.000 claims abstract description 33
- 206010028289 Muscle atrophy Diseases 0.000 claims abstract description 20
- 201000000585 muscular atrophy Diseases 0.000 claims abstract description 20
- 206010011878 Deafness Diseases 0.000 claims abstract description 19
- 230000010370 hearing loss Effects 0.000 claims abstract description 19
- 231100000888 hearing loss Toxicity 0.000 claims abstract description 19
- 208000016354 hearing loss disease Diseases 0.000 claims abstract description 19
- 230000020763 muscle atrophy Effects 0.000 claims abstract description 19
- 230000000451 tissue damage Effects 0.000 claims abstract description 19
- 231100000827 tissue damage Toxicity 0.000 claims abstract description 19
- 210000000056 organ Anatomy 0.000 claims abstract description 18
- 210000002027 skeletal muscle Anatomy 0.000 claims abstract description 18
- 230000017423 tissue regeneration Effects 0.000 claims abstract description 18
- -1 1- (4-((6H-benzo [c] fluoren-3-yl) methyl) phenyl)- 5-methyl-1H-pyrazole-3-carboxamide Chemical compound 0.000 claims description 366
- 125000000217 alkyl group Chemical group 0.000 claims description 201
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 188
- 229910052799 carbon Inorganic materials 0.000 claims description 118
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 111
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 74
- 125000000623 heterocyclic group Chemical group 0.000 claims description 72
- 125000005843 halogen group Chemical group 0.000 claims description 61
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 239000003814 drug Substances 0.000 claims description 37
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 229940124597 therapeutic agent Drugs 0.000 claims description 29
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 24
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 230000015556 catabolic process Effects 0.000 claims description 18
- 238000006731 degradation reaction Methods 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 230000004770 neurodegeneration Effects 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 15
- 125000002837 carbocyclic group Chemical group 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims description 14
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims description 14
- 108091007960 PI3Ks Proteins 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- AKWIAIDKXNKXDI-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C=CNC=1 AKWIAIDKXNKXDI-UHFFFAOYSA-N 0.000 claims description 9
- 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 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 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 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- SJCDBQHCQSIZHN-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxamide Chemical compound NC(=O)N1NNC=C1 SJCDBQHCQSIZHN-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
- 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 claims description 5
- 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 5
- 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 5
- 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 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
- 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 5
- 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 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
- 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
- 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 4
- 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 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
- QKKJCHAEHLWPPG-UHFFFAOYSA-N 1-[4-[[4-[4-[(cyclobutylamino)methyl]phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound C1(CCC1)NCC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(C=C1C)C(=O)N QKKJCHAEHLWPPG-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
- 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
- MPLPSASQUDJYBF-UHFFFAOYSA-N 1-[4-[[4-[6-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]pyridin-3-yl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OCCN1CCN(CC1)CC1=CC=C(C=N1)C1=CC=C(CC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)N)C=C1 MPLPSASQUDJYBF-UHFFFAOYSA-N 0.000 claims description 4
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- VRUQKDLYEZFXTL-UHFFFAOYSA-N 5-methyl-1-[4-[2-[4-(3-methylsulfonylphenyl)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(=CC=C1)S(=O)(=O)C)C(=O)N VRUQKDLYEZFXTL-UHFFFAOYSA-N 0.000 claims description 4
- WWXWCZYJRDWAIL-UHFFFAOYSA-N 5-methyl-1-[4-[2-[4-[4-(morpholin-4-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)CN1CCOCC1)C(=O)N WWXWCZYJRDWAIL-UHFFFAOYSA-N 0.000 claims description 4
- YBYMKWACYXHWGF-UHFFFAOYSA-N 5-methyl-1-[4-[[4-[4-(1-methylpyrrolidin-2-yl)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)C1N(CCC1)C)C(=O)N YBYMKWACYXHWGF-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
- 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 4
- 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 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- DROBUYPBFWBCMQ-UHFFFAOYSA-N 1-[4-[[4-[4-[3-(hydroxymethyl)piperazine-1-carbonyl]phenyl]phenyl]methyl]phenyl]-5-methylpyrazole-3-carboxamide Chemical compound OCC1CN(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-UHFFFAOYSA-N 0.000 claims description 3
- JEOCUYBQNAPOHZ-FITHBNAOSA-N 1-[4-[[4-[4-[[(1S,5R)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexan-3-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-1,2,4-triazole-3-carboxamide Chemical compound OCC1[C@H]2CN(C[C@@H]12)CC1=CC=C(C=C1)C1=CC=C(C=C1)CC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N JEOCUYBQNAPOHZ-FITHBNAOSA-N 0.000 claims description 3
- 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 3
- 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 3
- YIPZVPNYBNTJML-MKPDMIMOSA-N 1-[4-[[4-[4-[[(3aR,6aS)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]pyrrol-5-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-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)CN1C[C@@H]2[C@H](C1)COC2)C(=O)N YIPZVPNYBNTJML-MKPDMIMOSA-N 0.000 claims description 3
- LVKAXHBSOMKHNK-HNRBIFIRSA-N 1-[4-[[4-[4-[[(3aS,6aR)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]methyl]phenyl]phenyl]methyl]phenyl]-5-methyl-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)CN1C[C@@H]2CN(C[C@@H]2C1)C)C(=O)N LVKAXHBSOMKHNK-HNRBIFIRSA-N 0.000 claims description 3
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- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000004952 protein activity Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- FDDQRDMHICUGQC-UHFFFAOYSA-N pyrrole-1-carboxylic acid Chemical compound OC(=O)N1C=CC=C1 FDDQRDMHICUGQC-UHFFFAOYSA-N 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
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- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000013334 tissue model Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 229910052722 tritium Inorganic materials 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GIUOJMHOGPURPS-UHFFFAOYSA-M zinc;1-chloro-4-methanidylbenzene;chloride Chemical compound [Zn+]Cl.[CH2-]C1=CC=C(Cl)C=C1 GIUOJMHOGPURPS-UHFFFAOYSA-M 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
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
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| US201762558065P | 2017-09-13 | 2017-09-13 | |
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| TW201920112A true TW201920112A (zh) | 2019-06-01 |
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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 |
| WO2021216705A1 (en) | 2020-04-22 | 2021-10-28 | Neurocrine Biosciences, Inc. | Gpr52 modulators and methods of use |
| 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 |
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| WO2006136823A1 (en) * | 2005-06-21 | 2006-12-28 | Astex Therapeutics Limited | Heterocyclic containing amines as kinase b inhibitors |
| 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 |
| HK1206331A1 (en) * | 2012-08-09 | 2016-01-08 | Neuropore Therapies, Inc. | Aryl-and heteroaryl-substituted benzene derivatives as modulators of pi3-kinase signalling pathways |
| 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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