NO325160B1 - 1,2-dihydropyridinforbindelser, fremgangsmate for fremstilling av de samme og anvendelse derav - Google Patents
1,2-dihydropyridinforbindelser, fremgangsmate for fremstilling av de samme og anvendelse derav Download PDFInfo
- Publication number
- NO325160B1 NO325160B1 NO20025955A NO20025955A NO325160B1 NO 325160 B1 NO325160 B1 NO 325160B1 NO 20025955 A NO20025955 A NO 20025955A NO 20025955 A NO20025955 A NO 20025955A NO 325160 B1 NO325160 B1 NO 325160B1
- Authority
- NO
- Norway
- Prior art keywords
- pyridyl
- dihydropyridin
- phenyl
- cyanophenyl
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 191
- 230000008569 process Effects 0.000 title claims description 21
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical class C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 405
- 150000003839 salts Chemical class 0.000 claims abstract description 150
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 102000003678 AMPA Receptors Human genes 0.000 claims abstract description 27
- 108090000078 AMPA Receptors Proteins 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 175
- 239000002904 solvent Substances 0.000 claims description 166
- -1 piperidyloxy Chemical group 0.000 claims description 164
- 238000006243 chemical reaction Methods 0.000 claims description 149
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 75
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 68
- 239000002585 base Substances 0.000 claims description 65
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 58
- 238000005859 coupling reaction Methods 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 239000003054 catalyst Substances 0.000 claims description 50
- 239000003795 chemical substances by application Substances 0.000 claims description 35
- 229910052763 palladium Inorganic materials 0.000 claims description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 31
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 30
- 150000004677 hydrates Chemical class 0.000 claims description 29
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 239000003153 chemical reaction reagent Substances 0.000 claims description 27
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 24
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical group [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 23
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 23
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 23
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 22
- 125000001544 thienyl group Chemical group 0.000 claims description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 239000005749 Copper compound Substances 0.000 claims description 21
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 21
- 150000001880 copper compounds Chemical class 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 20
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 20
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 125000005493 quinolyl group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002541 furyl group Chemical group 0.000 claims description 18
- 238000005658 halogenation reaction Methods 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 102000000079 Kainic Acid Receptors Human genes 0.000 claims description 16
- 108010069902 Kainic Acid Receptors Proteins 0.000 claims description 16
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 16
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 16
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 16
- 229910052721 tungsten Inorganic materials 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 15
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 15
- 125000005945 imidazopyridyl group Chemical group 0.000 claims description 15
- 125000002524 organometallic group Chemical group 0.000 claims description 15
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 15
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 14
- 229910052723 transition metal Inorganic materials 0.000 claims description 14
- 150000003624 transition metals Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000001041 indolyl group Chemical group 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000000335 thiazolyl group Chemical group 0.000 claims description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 230000003449 preventive effect Effects 0.000 claims description 11
- 230000001225 therapeutic effect Effects 0.000 claims description 11
- 238000010511 deprotection reaction Methods 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- VAYWXCQNXGTBAQ-UHFFFAOYSA-N 2-[1-(3-aminophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound NC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 VAYWXCQNXGTBAQ-UHFFFAOYSA-N 0.000 claims description 8
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 8
- 208000018737 Parkinson disease Diseases 0.000 claims description 8
- QJTAAHJJXWYZSK-UHFFFAOYSA-N [Br].CC(O)=O Chemical compound [Br].CC(O)=O QJTAAHJJXWYZSK-UHFFFAOYSA-N 0.000 claims description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 206010015037 epilepsy Diseases 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- 238000006192 iodination reaction Methods 0.000 claims description 6
- PRMWGUBFXWROHD-UHFFFAOYSA-N perampanel Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 PRMWGUBFXWROHD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
- XJEGKWQBBPBZBM-UHFFFAOYSA-N 2-[5-(2-formylthiophen-3-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound S1C=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=C1C=O XJEGKWQBBPBZBM-UHFFFAOYSA-N 0.000 claims description 5
- KTUDVOUKZFBMAG-UHFFFAOYSA-N 3-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)thiophene-2-carbaldehyde Chemical compound S1C=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1C=O KTUDVOUKZFBMAG-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 238000005893 bromination reaction Methods 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- HAWPVMCOOMZUTD-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyrimidin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CN=2)=CN1C1=CC=CC=C1 HAWPVMCOOMZUTD-UHFFFAOYSA-N 0.000 claims description 4
- UYJJATPPJOSNFM-UHFFFAOYSA-N 2-(2-oxo-5-pyridin-2-yl-1-pyridin-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 UYJJATPPJOSNFM-UHFFFAOYSA-N 0.000 claims description 4
- SRIBOAOQCACOFW-UHFFFAOYSA-N 2-[1-(3-hydroxyphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound OC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 SRIBOAOQCACOFW-UHFFFAOYSA-N 0.000 claims description 4
- UZUVMMADDOPENK-UHFFFAOYSA-N 2-[1-(3-nitrophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 UZUVMMADDOPENK-UHFFFAOYSA-N 0.000 claims description 4
- SBAHNGRZWCURSP-UHFFFAOYSA-N 2-[1-(4-methylsulfanylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(SC)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 SBAHNGRZWCURSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000005749 2-halopyridines Chemical class 0.000 claims description 4
- YWVMGZYXPNDLRV-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-hydroxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)Cl)=CC(C=2N=CC=CC=2)=C1 YWVMGZYXPNDLRV-UHFFFAOYSA-N 0.000 claims description 4
- AISWTIWIIAADRP-UHFFFAOYSA-N 3-(2-chloropyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound ClC1=NC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 AISWTIWIIAADRP-UHFFFAOYSA-N 0.000 claims description 4
- BMXYEXPMZDKGCR-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound FC1=NC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 BMXYEXPMZDKGCR-UHFFFAOYSA-N 0.000 claims description 4
- BGTNYGOBNLWJRT-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound FC1=NC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 BGTNYGOBNLWJRT-UHFFFAOYSA-N 0.000 claims description 4
- 206010034010 Parkinsonism Diseases 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- XAEMOTNPVLUMRS-UHFFFAOYSA-N methyl 3-[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 XAEMOTNPVLUMRS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- OBRUTSCSGNDVDC-UHFFFAOYSA-N 1,3-diphenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 OBRUTSCSGNDVDC-UHFFFAOYSA-N 0.000 claims description 3
- HBVRDIGMVDCZRS-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-(2-fluoropyridin-3-yl)-5-pyridin-2-ylpyridin-2-one Chemical compound FC1=CC=CC(N2C(C(C=3C(=NC=CC=3)F)=CC(=C2)C=2N=CC=CC=2)=O)=C1 HBVRDIGMVDCZRS-UHFFFAOYSA-N 0.000 claims description 3
- NUWRPCHEZDSDPK-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound FC1=CC=CC(N2C(C(C=3C=CC=CC=3)=CC(=C2)C=2N=CC=CC=2)=O)=C1 NUWRPCHEZDSDPK-UHFFFAOYSA-N 0.000 claims description 3
- ORJCITCNJVUPSP-UHFFFAOYSA-N 2-(1-benzyl-2-oxo-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1CC1=CC=CC=C1 ORJCITCNJVUPSP-UHFFFAOYSA-N 0.000 claims description 3
- UXUALQPGAMIQLC-UHFFFAOYSA-N 2-(2-oxo-1,5-diphenylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=CC=CC=2)=CN1C1=CC=CC=C1 UXUALQPGAMIQLC-UHFFFAOYSA-N 0.000 claims description 3
- VSSVPRRVRYAVQU-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-thiophen-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2SC=CC=2)=CN1C1=CC=CC=C1 VSSVPRRVRYAVQU-UHFFFAOYSA-N 0.000 claims description 3
- PYEKXHCYVSBIMU-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-thiophen-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C2=CSC=C2)=CN1C1=CC=CC=C1 PYEKXHCYVSBIMU-UHFFFAOYSA-N 0.000 claims description 3
- BDAUQVDIEIVKDH-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-1-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=CC=CC=2)=CN1C1=CC=CC=N1 BDAUQVDIEIVKDH-UHFFFAOYSA-N 0.000 claims description 3
- UNSTVPJCWLUIPT-UHFFFAOYSA-N 2-(2-oxo-5-pyridin-2-yl-1-pyridin-4-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=NC=C1 UNSTVPJCWLUIPT-UHFFFAOYSA-N 0.000 claims description 3
- OVMRJNJAFNMBJT-UHFFFAOYSA-N 2-(2-oxo-5-pyridin-2-yl-1-thiophen-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C=1C=CSC=1 OVMRJNJAFNMBJT-UHFFFAOYSA-N 0.000 claims description 3
- RPXOWGJZXRBGDS-UHFFFAOYSA-N 2-[1-(2-amino-1,3-benzothiazol-6-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=C2SC(N)=NC2=CC=C1N(C1=O)C=C(C=2N=CC=CC=2)C=C1C1=CC=CC=C1C#N RPXOWGJZXRBGDS-UHFFFAOYSA-N 0.000 claims description 3
- OJBKXQJKVPRFNR-UHFFFAOYSA-N 2-[1-(2-formylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=CC1=CC=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 OJBKXQJKVPRFNR-UHFFFAOYSA-N 0.000 claims description 3
- PXKNDCRXLYKBJZ-UHFFFAOYSA-N 2-[1-(2-methoxyphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound COC1=CC=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 PXKNDCRXLYKBJZ-UHFFFAOYSA-N 0.000 claims description 3
- FSVBNVCEZCRHIY-UHFFFAOYSA-N 2-[1-(3-amino-4-methylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=C(N)C(C)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 FSVBNVCEZCRHIY-UHFFFAOYSA-N 0.000 claims description 3
- AWPTWYZHDCDVGD-UHFFFAOYSA-N 2-[1-(3-aminophenyl)-2-oxo-5-pyrimidin-2-ylpyridin-3-yl]benzonitrile Chemical compound NC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CN=2)=O)=C1 AWPTWYZHDCDVGD-UHFFFAOYSA-N 0.000 claims description 3
- KNFHMGXRIPWLDL-UHFFFAOYSA-N 2-[1-(3-chlorophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound ClC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 KNFHMGXRIPWLDL-UHFFFAOYSA-N 0.000 claims description 3
- TVYAIBSGGCSTFQ-UHFFFAOYSA-N 2-[1-(3-fluorophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound FC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 TVYAIBSGGCSTFQ-UHFFFAOYSA-N 0.000 claims description 3
- IEEWWCIQFGXEKC-UHFFFAOYSA-N 2-[1-(3-formylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=CC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 IEEWWCIQFGXEKC-UHFFFAOYSA-N 0.000 claims description 3
- UYDWRKIMEHMHMK-UHFFFAOYSA-N 2-[1-(3-methoxyphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound COC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 UYDWRKIMEHMHMK-UHFFFAOYSA-N 0.000 claims description 3
- ZZHSASAPKFAMAN-UHFFFAOYSA-N 2-[1-(3-methylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 ZZHSASAPKFAMAN-UHFFFAOYSA-N 0.000 claims description 3
- MTKNBZLFVHRRGB-UHFFFAOYSA-N 2-[1-(3-nitrophenyl)-2-oxo-5-pyrimidin-2-ylpyridin-3-yl]benzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CN=2)=O)=C1 MTKNBZLFVHRRGB-UHFFFAOYSA-N 0.000 claims description 3
- GXSSHSBGGFTCBQ-UHFFFAOYSA-N 2-[1-(4-aminophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(N)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 GXSSHSBGGFTCBQ-UHFFFAOYSA-N 0.000 claims description 3
- WGGKBQUXECUXRN-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 WGGKBQUXECUXRN-UHFFFAOYSA-N 0.000 claims description 3
- ZAZNCROEFXCCQV-UHFFFAOYSA-N 2-[1-(4-formylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(C=O)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 ZAZNCROEFXCCQV-UHFFFAOYSA-N 0.000 claims description 3
- KZYPCFXPJZHGFD-UHFFFAOYSA-N 2-[1-(4-methoxyphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 KZYPCFXPJZHGFD-UHFFFAOYSA-N 0.000 claims description 3
- KQYHSOWCKOKJQP-UHFFFAOYSA-N 2-[1-(4-methylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 KQYHSOWCKOKJQP-UHFFFAOYSA-N 0.000 claims description 3
- UPMSVPRHAFICPZ-UHFFFAOYSA-N 2-[1-(4-methylsulfonylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 UPMSVPRHAFICPZ-UHFFFAOYSA-N 0.000 claims description 3
- XVHFNFSNCDXUMG-UHFFFAOYSA-N 2-[1-(5-methoxypyridin-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound COC1=CN=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 XVHFNFSNCDXUMG-UHFFFAOYSA-N 0.000 claims description 3
- FPDVRZPKNRGEFZ-UHFFFAOYSA-N 2-[1-(6-chloropyridin-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=NC(Cl)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 FPDVRZPKNRGEFZ-UHFFFAOYSA-N 0.000 claims description 3
- BALOECZIFSUQJX-UHFFFAOYSA-N 2-[1-(6-ethylsulfanylpyridin-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=NC(SCC)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 BALOECZIFSUQJX-UHFFFAOYSA-N 0.000 claims description 3
- VGDOZYUYQRLOBW-UHFFFAOYSA-N 2-[1-(6-methoxypyridin-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=NC(OC)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 VGDOZYUYQRLOBW-UHFFFAOYSA-N 0.000 claims description 3
- WMBPDXCBZMBKKG-UHFFFAOYSA-N 2-[1-(furan-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C=1C=COC=1 WMBPDXCBZMBKKG-UHFFFAOYSA-N 0.000 claims description 3
- JKANAXFKIKOPLH-UHFFFAOYSA-N 2-[1-[2-(cyanomethyl)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1CC#N JKANAXFKIKOPLH-UHFFFAOYSA-N 0.000 claims description 3
- DLGYCYJSVYNVRM-UHFFFAOYSA-N 2-[1-[3-(1-methylpiperidin-4-yl)oxyphenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1CN(C)CCC1OC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 DLGYCYJSVYNVRM-UHFFFAOYSA-N 0.000 claims description 3
- HPWJAFXTTZHDRZ-UHFFFAOYSA-N 2-[1-[3-(cyanomethyl)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC(CC#N)=C1 HPWJAFXTTZHDRZ-UHFFFAOYSA-N 0.000 claims description 3
- CHFMJQYTCOYAGH-UHFFFAOYSA-N 2-[1-[3-(dimethylamino)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CN(C)C1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 CHFMJQYTCOYAGH-UHFFFAOYSA-N 0.000 claims description 3
- ZVEWTPBUDSVPJC-UHFFFAOYSA-N 2-[1-[3-(methylamino)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CNC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 ZVEWTPBUDSVPJC-UHFFFAOYSA-N 0.000 claims description 3
- YFBHWKLDFOTNNQ-UHFFFAOYSA-N 2-[1-[3-[2-(dimethylamino)ethoxy]phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CN(C)CCOC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 YFBHWKLDFOTNNQ-UHFFFAOYSA-N 0.000 claims description 3
- PAYYJKPPKZKVFV-UHFFFAOYSA-N 2-[1-[3-[5-(methoxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1OC(COC)CN1C1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 PAYYJKPPKZKVFV-UHFFFAOYSA-N 0.000 claims description 3
- SHEYBDVSKOWDMA-UHFFFAOYSA-N 2-[1-[4-(cyanomethyl)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=C(CC#N)C=C1 SHEYBDVSKOWDMA-UHFFFAOYSA-N 0.000 claims description 3
- YHUWBIBLNSGDIR-UHFFFAOYSA-N 2-[2-oxo-1-[3-(2-piperidin-1-ylethoxy)phenyl]-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CC=CC=1OCCN1CCCCC1 YHUWBIBLNSGDIR-UHFFFAOYSA-N 0.000 claims description 3
- ADVIPHAPALQTAR-UHFFFAOYSA-N 2-[2-oxo-1-[5-(phenylmethoxymethyl)pyridin-3-yl]-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CN=CC=1COCC1=CC=CC=C1 ADVIPHAPALQTAR-UHFFFAOYSA-N 0.000 claims description 3
- PZGWHOWDAZFUJO-UHFFFAOYSA-N 2-[2-oxo-1-phenyl-5-(1,3-thiazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2SC=CN=2)=CN1C1=CC=CC=C1 PZGWHOWDAZFUJO-UHFFFAOYSA-N 0.000 claims description 3
- SWOWDEFHSSXPMX-UHFFFAOYSA-N 2-[2-oxo-5-pyridin-2-yl-1-[3-(trifluoromethyl)phenyl]pyridin-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 SWOWDEFHSSXPMX-UHFFFAOYSA-N 0.000 claims description 3
- ORTQXUXPELXLAB-UHFFFAOYSA-N 2-[2-oxo-5-pyridin-2-yl-1-[4-(trifluoromethyl)phenyl]pyridin-3-yl]benzonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 ORTQXUXPELXLAB-UHFFFAOYSA-N 0.000 claims description 3
- DRCIUZZYDGCZKC-UHFFFAOYSA-N 2-[5-(2-fluorophenyl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound FC1=CC=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 DRCIUZZYDGCZKC-UHFFFAOYSA-N 0.000 claims description 3
- PNRVQMKGCIHJTK-UHFFFAOYSA-N 2-[5-(2-methoxyphenyl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound COC1=CC=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 PNRVQMKGCIHJTK-UHFFFAOYSA-N 0.000 claims description 3
- ILIMNTJQKZLNSO-UHFFFAOYSA-N 2-[5-(3,4-dimethoxyphenyl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 ILIMNTJQKZLNSO-UHFFFAOYSA-N 0.000 claims description 3
- NMRYXQCGTCYCFV-UHFFFAOYSA-N 2-[5-(3-hydroxypyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound OC1=CC=CN=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 NMRYXQCGTCYCFV-UHFFFAOYSA-N 0.000 claims description 3
- QWVZEPOFQXVCIF-UHFFFAOYSA-N 2-[5-(5-methylpyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N1=CC(C)=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 QWVZEPOFQXVCIF-UHFFFAOYSA-N 0.000 claims description 3
- HLPXMQNKYVXIFS-UHFFFAOYSA-N 2-[5-(6-bromopyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound BrC1=CC=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=N1 HLPXMQNKYVXIFS-UHFFFAOYSA-N 0.000 claims description 3
- MIIUNJUGFYQMDE-UHFFFAOYSA-N 2-[5-(6-methoxypyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound COC1=CC=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=N1 MIIUNJUGFYQMDE-UHFFFAOYSA-N 0.000 claims description 3
- YYUAVYNWNFRMEX-UHFFFAOYSA-N 2-[5-(furan-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2OC=CC=2)=CN1C1=CC=CC=C1 YYUAVYNWNFRMEX-UHFFFAOYSA-N 0.000 claims description 3
- VKHTYXHWYBCTGJ-UHFFFAOYSA-N 2-[5-(furan-3-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C2=COC=C2)=CN1C1=CC=CC=C1 VKHTYXHWYBCTGJ-UHFFFAOYSA-N 0.000 claims description 3
- JTSHGRSOCKDKSD-UHFFFAOYSA-N 2-[5-[2-(diethylaminomethyl)thiophen-3-yl]-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound S1C=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=C1CN(CC)CC JTSHGRSOCKDKSD-UHFFFAOYSA-N 0.000 claims description 3
- DYPSTMQSGHFEFJ-UHFFFAOYSA-N 2-[5-[2-(hydroxymethyl)thiophen-3-yl]-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound S1C=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=C1CO DYPSTMQSGHFEFJ-UHFFFAOYSA-N 0.000 claims description 3
- DTQULZGXSSNUCP-UHFFFAOYSA-N 2-[5-[6-(diethylaminomethyl)pyridin-2-yl]-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound CCN(CC)CC1=CC=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=N1 DTQULZGXSSNUCP-UHFFFAOYSA-N 0.000 claims description 3
- HPNOKFAMDVBHDE-UHFFFAOYSA-N 3-(2,6-dimethylphenyl)-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound CC1=CC=CC(C)=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 HPNOKFAMDVBHDE-UHFFFAOYSA-N 0.000 claims description 3
- FCZNKYPVTAHPCO-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(3-hydroxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound OC1=CC=CC(N2C(C(C=3C(=CC=CC=3)Cl)=CC(=C2)C=2N=CC=CC=2)=O)=C1 FCZNKYPVTAHPCO-UHFFFAOYSA-N 0.000 claims description 3
- JGYAGDDTSSVEAG-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)Cl)=CC(C=2N=CC=CC=2)=C1 JGYAGDDTSSVEAG-UHFFFAOYSA-N 0.000 claims description 3
- OPRUKMXXVPQIOF-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-[2-[3-(dimethylamino)propoxy]phenyl]-5-pyridin-2-ylpyridin-2-one Chemical compound CN(C)CCCOC1=CC=CC=C1N1C(=O)C(C=2C(=CC=CC=2)Cl)=CC(C=2N=CC=CC=2)=C1 OPRUKMXXVPQIOF-UHFFFAOYSA-N 0.000 claims description 3
- AANFFKAQYYILPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-[3-[2-(dimethylamino)ethoxy]phenyl]-5-pyridin-2-ylpyridin-2-one Chemical compound CN(C)CCOC1=CC=CC(N2C(C(C=3C(=CC=CC=3)Cl)=CC(=C2)C=2N=CC=CC=2)=O)=C1 AANFFKAQYYILPX-UHFFFAOYSA-N 0.000 claims description 3
- QSQAWDLDFQXCGX-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(OCCN(C)C)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)Cl)=CC(C=2N=CC=CC=2)=C1 QSQAWDLDFQXCGX-UHFFFAOYSA-N 0.000 claims description 3
- QLYBJSAIVVWOPP-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound ClC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QLYBJSAIVVWOPP-UHFFFAOYSA-N 0.000 claims description 3
- MRTOEHCBCUGICH-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound ClC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 MRTOEHCBCUGICH-UHFFFAOYSA-N 0.000 claims description 3
- UXIVBSREKRCXPW-UHFFFAOYSA-N 3-(2-fluorophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound FC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 UXIVBSREKRCXPW-UHFFFAOYSA-N 0.000 claims description 3
- FJAUTYUZNMXHDC-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-1-(3-methoxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound COC1=CC=CC(N2C(C(C=3C(=NC=CC=3)F)=CC(=C2)C=2N=CC=CC=2)=O)=C1 FJAUTYUZNMXHDC-UHFFFAOYSA-N 0.000 claims description 3
- CRKADRRMBRCTCT-UHFFFAOYSA-N 3-(2-nitrophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 CRKADRRMBRCTCT-UHFFFAOYSA-N 0.000 claims description 3
- PLIZTYWVQASSAE-UHFFFAOYSA-N 3-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)pyridine-2-carbonitrile Chemical compound O=C1C(C=2C(=NC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 PLIZTYWVQASSAE-UHFFFAOYSA-N 0.000 claims description 3
- ZMNWXHZSYLBCIG-UHFFFAOYSA-N 3-(2-oxo-5-pyridin-2-yl-1-pyridin-3-ylpyridin-3-yl)thiophene-2-carbonitrile Chemical compound O=C1C(C2=C(SC=C2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 ZMNWXHZSYLBCIG-UHFFFAOYSA-N 0.000 claims description 3
- JKWYRKMVVXFLJR-UHFFFAOYSA-N 3-(6-oxo-1h-pyridin-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound OC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=N1 JKWYRKMVVXFLJR-UHFFFAOYSA-N 0.000 claims description 3
- LIQWSSNIMMLXBV-UHFFFAOYSA-N 3-[2-(1,3-oxazol-5-yl)phenyl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2C(=CC=CC=2)C=2OC=NC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 LIQWSSNIMMLXBV-UHFFFAOYSA-N 0.000 claims description 3
- QUCLLVDPQMXLMA-UHFFFAOYSA-N 3-[2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O1C(C)=NC(C=2C(=CC=CC=2)C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=N1 QUCLLVDPQMXLMA-UHFFFAOYSA-N 0.000 claims description 3
- KYLNQFFKALLDPF-UHFFFAOYSA-N 3-[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 KYLNQFFKALLDPF-UHFFFAOYSA-N 0.000 claims description 3
- IFSJBYIVJYAKOF-UHFFFAOYSA-N 3-phenyl-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 IFSJBYIVJYAKOF-UHFFFAOYSA-N 0.000 claims description 3
- XLOBLKSBINMEPZ-UHFFFAOYSA-N 5-pyridin-2-yl-1-pyridin-3-yl-3-thiophen-3-ylpyridin-2-one Chemical compound O=C1C(C2=CSC=C2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 XLOBLKSBINMEPZ-UHFFFAOYSA-N 0.000 claims description 3
- LVAILVUXOFTKOY-UHFFFAOYSA-N [3-[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]phenyl]methyl acetate Chemical compound CC(=O)OCC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 LVAILVUXOFTKOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- CZVJGEWQTDYGNY-UHFFFAOYSA-N ethyl 3-[3-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)thiophen-2-yl]prop-2-enoate Chemical compound S1C=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1C=CC(=O)OCC CZVJGEWQTDYGNY-UHFFFAOYSA-N 0.000 claims description 3
- XJOJWQKENXRJQP-UHFFFAOYSA-N methyl 2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 XJOJWQKENXRJQP-UHFFFAOYSA-N 0.000 claims description 3
- WPHURXZUZWMENM-UHFFFAOYSA-N n-[2-[5-(2-cyanophenyl)-6-oxo-1-phenylpyridin-3-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 WPHURXZUZWMENM-UHFFFAOYSA-N 0.000 claims description 3
- IWGNKNLLKIQVNT-UHFFFAOYSA-N n-[3-[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 IWGNKNLLKIQVNT-UHFFFAOYSA-N 0.000 claims description 3
- KWQIRBDGJOQBFU-UHFFFAOYSA-N n-[[3-[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 KWQIRBDGJOQBFU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- ALLWLWLGHPVIEP-UHFFFAOYSA-N 2-(2-oxo-1-pyridin-3-yl-5-pyrimidin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CN=2)=CN1C1=CC=CN=C1 ALLWLWLGHPVIEP-UHFFFAOYSA-N 0.000 claims description 2
- GKRLAACEQJTILE-UHFFFAOYSA-N 2-(2-oxo-5-pyridin-2-yl-1-pyrimidin-5-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CN=CN=C1 GKRLAACEQJTILE-UHFFFAOYSA-N 0.000 claims description 2
- MTKBHZFBGWUNCH-UHFFFAOYSA-N 2-[1-[2-(hydroxymethyl)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound OCC1=CC=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 MTKBHZFBGWUNCH-UHFFFAOYSA-N 0.000 claims description 2
- RFDCHWAANADQJF-UHFFFAOYSA-N 2-[1-[3-(hydroxymethyl)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound OCC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 RFDCHWAANADQJF-UHFFFAOYSA-N 0.000 claims description 2
- BRCNPMJCWOUFRG-UHFFFAOYSA-N 2-[5-(6-methylpyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound CC1=CC=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=N1 BRCNPMJCWOUFRG-UHFFFAOYSA-N 0.000 claims description 2
- 150000005762 2-bromopyridine Chemical class 0.000 claims description 2
- YFPVYPPCNYJAIE-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(3-methoxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound COC1=CC=CC(N2C(C(C=3C(=CC=CC=3)Cl)=CC(=C2)C=2N=CC=CC=2)=O)=C1 YFPVYPPCNYJAIE-UHFFFAOYSA-N 0.000 claims description 2
- HAPXITMJHWWHNQ-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-1-phenyl-5-pyrimidin-2-ylpyridin-2-one Chemical compound FC1=NC=CC=C1C(C1=O)=CC(C=2N=CC=CN=2)=CN1C1=CC=CC=C1 HAPXITMJHWWHNQ-UHFFFAOYSA-N 0.000 claims description 2
- BLOWTBSEUQDRSS-UHFFFAOYSA-N 3-(2-oxo-1-phenyl-5-pyrimidin-2-ylpyridin-3-yl)pyridine-2-carbonitrile Chemical compound O=C1C(C=2C(=NC=CC=2)C#N)=CC(C=2N=CC=CN=2)=CN1C1=CC=CC=C1 BLOWTBSEUQDRSS-UHFFFAOYSA-N 0.000 claims description 2
- GKPFYPIDECPKHB-UHFFFAOYSA-N 3-[2-(1,3-oxazol-5-yl)thiophen-3-yl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C2=C(SC=C2)C=2OC=NC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 GKPFYPIDECPKHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- KORDQHHCNIQTCL-UHFFFAOYSA-N 2-[1-(1-benzyl-3,6-dihydro-2h-pyridin-5-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C1)=CCCN1CC1=CC=CC=C1 KORDQHHCNIQTCL-UHFFFAOYSA-N 0.000 claims 1
- AWINTQLGTLXJOY-UHFFFAOYSA-N N-[3-[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]-2-methylphenyl]methanesulfonamide Chemical compound C(#N)C1=C(C=CC=C1)C=1C(N(C=C(C=1)C1=NC=CC=C1)C1=C(C(=CC=C1)NS(=O)(=O)C)C)=O AWINTQLGTLXJOY-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 6
- 239000003112 inhibitor Substances 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 462
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 390
- 238000005160 1H NMR spectroscopy Methods 0.000 description 372
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 198
- 239000000203 mixture Substances 0.000 description 124
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 111
- 239000000243 solution Substances 0.000 description 104
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 98
- 238000003756 stirring Methods 0.000 description 81
- 238000010898 silica gel chromatography Methods 0.000 description 78
- 238000001816 cooling Methods 0.000 description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 239000012044 organic layer Substances 0.000 description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- 238000005481 NMR spectroscopy Methods 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 51
- 239000012267 brine Substances 0.000 description 48
- 239000002994 raw material Substances 0.000 description 45
- 239000012299 nitrogen atmosphere Substances 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000007864 aqueous solution Substances 0.000 description 35
- 101150041968 CDC13 gene Proteins 0.000 description 34
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 29
- 235000019341 magnesium sulphate Nutrition 0.000 description 29
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 28
- 150000001543 aryl boronic acids Chemical class 0.000 description 27
- 238000010992 reflux Methods 0.000 description 27
- 239000000843 powder Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 24
- 229920006395 saturated elastomer Polymers 0.000 description 22
- 239000013078 crystal Substances 0.000 description 21
- 238000000605 extraction Methods 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- 239000008096 xylene Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 208000016192 Demyelinating disease Diseases 0.000 description 13
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 13
- 229930195712 glutamate Natural products 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- GSESXDVCGLBTLD-UHFFFAOYSA-N 3-bromo-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(Br)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 GSESXDVCGLBTLD-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 11
- 150000002366 halogen compounds Chemical class 0.000 description 11
- 230000004770 neurodegeneration Effects 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 230000001154 acute effect Effects 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 210000005036 nerve Anatomy 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 208000015122 neurodegenerative disease Diseases 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 241000725303 Human immunodeficiency virus Species 0.000 description 8
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 8
- 239000002274 desiccant Substances 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- NSMXWIBVWJWRAA-UHFFFAOYSA-N 2-(2-cyanophenyl)-4H-1,3,2-dioxaborinine-4-carboxylic acid Chemical compound O1C=CC(C(=O)O)OB1C1=CC=CC=C1C#N NSMXWIBVWJWRAA-UHFFFAOYSA-N 0.000 description 7
- 208000024827 Alzheimer disease Diseases 0.000 description 7
- 206010028570 Myelopathy Diseases 0.000 description 7
- 208000002193 Pain Diseases 0.000 description 7
- GQDCUDAXOMFYFV-UHFFFAOYSA-N [Zn]C1=CC=CC=C1 Chemical compound [Zn]C1=CC=CC=C1 GQDCUDAXOMFYFV-UHFFFAOYSA-N 0.000 description 7
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 208000008795 neuromyelitis optica Diseases 0.000 description 7
- ODOPKAJVFRHHGM-UHFFFAOYSA-N phenyltin Chemical compound [Sn]C1=CC=CC=C1 ODOPKAJVFRHHGM-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 7
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 206010019196 Head injury Diseases 0.000 description 6
- 208000023105 Huntington disease Diseases 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 201000002491 encephalomyelitis Diseases 0.000 description 6
- 230000002964 excitative effect Effects 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000008177 pharmaceutical agent Substances 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 208000020431 spinal cord injury Diseases 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- MECNIGGKZPCOJT-UHFFFAOYSA-N 2-(5-bromo-2-oxo-1-phenylpyridin-3-yl)benzonitrile Chemical compound O=C1N(C=2C=CC=CC=2)C=C(Br)C=C1C1=CC=CC=C1C#N MECNIGGKZPCOJT-UHFFFAOYSA-N 0.000 description 5
- HKRPIELNADUEDQ-UHFFFAOYSA-N 3-amino-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 HKRPIELNADUEDQ-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 206010021143 Hypoxia Diseases 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 201000009906 Meningitis Diseases 0.000 description 5
- 206010029350 Neurotoxicity Diseases 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
- 206010044221 Toxic encephalopathy Diseases 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 208000026106 cerebrovascular disease Diseases 0.000 description 5
- 230000001684 chronic effect Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 230000007954 hypoxia Effects 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 230000002458 infectious effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 201000001119 neuropathy Diseases 0.000 description 5
- 230000007823 neuropathy Effects 0.000 description 5
- 230000007135 neurotoxicity Effects 0.000 description 5
- 231100000228 neurotoxicity Toxicity 0.000 description 5
- 239000002858 neurotransmitter agent Substances 0.000 description 5
- 208000033808 peripheral neuropathy Diseases 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 5
- WEUSJAFAAPHFIY-UHFFFAOYSA-N 2-[2-oxo-1-(piperidin-4-ylmethyl)-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1CC1CCNCC1 WEUSJAFAAPHFIY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 206010008025 Cerebellar ataxia Diseases 0.000 description 4
- 206010013654 Drug abuse Diseases 0.000 description 4
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 4
- 241000598436 Human T-cell lymphotropic virus Species 0.000 description 4
- 208000013016 Hypoglycemia Diseases 0.000 description 4
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 4
- 208000008238 Muscle Spasticity Diseases 0.000 description 4
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 4
- 206010069350 Osmotic demyelination syndrome Diseases 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 208000010112 Spinocerebellar Degenerations Diseases 0.000 description 4
- 238000006887 Ullmann reaction Methods 0.000 description 4
- 208000002552 acute disseminated encephalomyelitis Diseases 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 208000010353 central nervous system vasculitis Diseases 0.000 description 4
- 208000009885 central pontine myelinolysis Diseases 0.000 description 4
- 206010014599 encephalitis Diseases 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XSYUDOXRZMNSKB-UHFFFAOYSA-N methyl 5-(2-cyanophenyl)-6-oxo-1-phenylpyridine-3-carboxylate Chemical compound O=C1N(C=2C=CC=CC=2)C=C(C(=O)OC)C=C1C1=CC=CC=C1C#N XSYUDOXRZMNSKB-UHFFFAOYSA-N 0.000 description 4
- QUXXZRRPAXEXNG-UHFFFAOYSA-N methyl 5-bromo-6-oxo-1-phenylpyridine-3-carboxylate Chemical compound C1=C(C(=O)OC)C=C(Br)C(=O)N1C1=CC=CC=C1 QUXXZRRPAXEXNG-UHFFFAOYSA-N 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 201000006292 polyarteritis nodosa Diseases 0.000 description 4
- 201000000306 sarcoidosis Diseases 0.000 description 4
- 208000018198 spasticity Diseases 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
- 208000011580 syndromic disease Diseases 0.000 description 4
- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 3
- NAWVENJTRMIKRW-UHFFFAOYSA-N 2-(2-oxo-5-pyridin-2-yl-1h-pyridin-3-yl)benzonitrile Chemical compound O=C1NC=C(C=2N=CC=CC=2)C=C1C1=CC=CC=C1C#N NAWVENJTRMIKRW-UHFFFAOYSA-N 0.000 description 3
- IDKGFKZUFQXJIQ-UHFFFAOYSA-N 2-(5-nitro-2-oxo-1-phenylpyridin-3-yl)benzonitrile Chemical compound O=C1N(C=2C=CC=CC=2)C=C([N+](=O)[O-])C=C1C1=CC=CC=C1C#N IDKGFKZUFQXJIQ-UHFFFAOYSA-N 0.000 description 3
- XICIFIPJVFWZCO-UHFFFAOYSA-N 2-[2-oxo-1-phenyl-5-(pyridine-2-carbonyl)pyridin-3-yl]benzonitrile Chemical compound C=1C=CC=NC=1C(=O)C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1C#N XICIFIPJVFWZCO-UHFFFAOYSA-N 0.000 description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- UJPYMIMQCNFHQE-UHFFFAOYSA-N 3-bromo-1-phenyl-5-(pyridine-2-carbonyl)pyridin-2-one Chemical compound O=C1C(Br)=CC(C(=O)C=2N=CC=CC=2)=CN1C1=CC=CC=C1 UJPYMIMQCNFHQE-UHFFFAOYSA-N 0.000 description 3
- SAISPIQEZDOAKC-UHFFFAOYSA-N 3-bromo-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound O=C1C(Br)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 SAISPIQEZDOAKC-UHFFFAOYSA-N 0.000 description 3
- PEQPGOOJLLJRPM-UHFFFAOYSA-N 3-bromo-5-pyridin-2-yl-1h-pyridin-2-one Chemical compound N1C(=O)C(Br)=CC(C=2N=CC=CC=2)=C1 PEQPGOOJLLJRPM-UHFFFAOYSA-N 0.000 description 3
- KCLSASGVLPGAIB-UHFFFAOYSA-N 5-bromo-3-iodo-1-phenylpyridin-2-one Chemical compound C1=C(Br)C=C(I)C(=O)N1C1=CC=CC=C1 KCLSASGVLPGAIB-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
- 206010016952 Food poisoning Diseases 0.000 description 3
- 208000019331 Foodborne disease Diseases 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000010412 Glaucoma Diseases 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 206010028813 Nausea Diseases 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 206010047700 Vomiting Diseases 0.000 description 3
- XPOVEKCCCRWVQZ-UHFFFAOYSA-N [6-[5-(2-cyanophenyl)-6-oxo-1-phenylpyridin-3-yl]pyridin-3-yl] acetate Chemical compound N1=CC(OC(=O)C)=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 XPOVEKCCCRWVQZ-UHFFFAOYSA-N 0.000 description 3
- WMJMABVHDMRMJA-UHFFFAOYSA-M [Cl-].[Mg+]C1CCCCC1 Chemical compound [Cl-].[Mg+]C1CCCCC1 WMJMABVHDMRMJA-UHFFFAOYSA-M 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 208000011235 central nervous system lupus Diseases 0.000 description 3
- 206010008118 cerebral infarction Diseases 0.000 description 3
- 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 229940014259 gelatin Drugs 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 208000007386 hepatic encephalopathy Diseases 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- ANLYIGWSUNQHRI-UHFFFAOYSA-N methyl 2-oxo-1-phenyl-5-pyridin-2-ylpyridine-3-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ANLYIGWSUNQHRI-UHFFFAOYSA-N 0.000 description 3
- SCFLONUNSORRGI-UHFFFAOYSA-N methyl 5-(2-chlorophenyl)-6-oxo-1-phenylpyridine-3-carboxylate Chemical compound O=C1N(C=2C=CC=CC=2)C=C(C(=O)OC)C=C1C1=CC=CC=C1Cl SCFLONUNSORRGI-UHFFFAOYSA-N 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 230000008693 nausea Effects 0.000 description 3
- 208000004296 neuralgia Diseases 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 description 3
- 201000000980 schizophrenia Diseases 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 3
- 150000003752 zinc compounds Chemical class 0.000 description 3
- QQDNZLLNVWTREG-UHFFFAOYSA-N (6-methoxypyridin-3-yl)-pyridin-2-ylmethanol Chemical compound C1=NC(OC)=CC=C1C(O)C1=CC=CC=N1 QQDNZLLNVWTREG-UHFFFAOYSA-N 0.000 description 2
- XUHJXLCYFRJBIR-UHFFFAOYSA-N (6-methoxypyridin-3-yl)-pyridin-2-ylmethanone Chemical compound C1=NC(OC)=CC=C1C(=O)C1=CC=CC=N1 XUHJXLCYFRJBIR-UHFFFAOYSA-N 0.000 description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 2
- VLSDXINSOMDCBK-BQYQJAHWSA-N (E)-1,1'-azobis(N,N-dimethylformamide) Chemical compound CN(C)C(=O)\N=N\C(=O)N(C)C VLSDXINSOMDCBK-BQYQJAHWSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- WVGIKURDIHJELC-UHFFFAOYSA-N 1,5-dipyridin-2-ylpyridin-2-one Chemical compound O=C1C=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=N1 WVGIKURDIHJELC-UHFFFAOYSA-N 0.000 description 2
- MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 0.000 description 2
- UQNAFPHGVPVTAL-UHFFFAOYSA-N 2,3-Dihydroxy-6-nitro-7-sulfamoyl-benzo(f)quinoxaline Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C1=C2C=CC=C1S(=O)(=O)N UQNAFPHGVPVTAL-UHFFFAOYSA-N 0.000 description 2
- JRUJPPXXVNKJNI-UHFFFAOYSA-N 2-(2-methoxy-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound COC1=NC=C(C=2N=CC=CC=2)C=C1C1=CC=CC=C1C#N JRUJPPXXVNKJNI-UHFFFAOYSA-N 0.000 description 2
- OWGUJMFIWYHPNC-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-tributylstannylpyridin-3-yl)benzonitrile Chemical compound O=C1N(C=2C=CC=CC=2)C=C([Sn](CCCC)(CCCC)CCCC)C=C1C1=CC=CC=C1C#N OWGUJMFIWYHPNC-UHFFFAOYSA-N 0.000 description 2
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 2
- YDKPVJSTXZAHAV-UHFFFAOYSA-N 2-[1-(6-fluoropyridin-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=NC(F)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 YDKPVJSTXZAHAV-UHFFFAOYSA-N 0.000 description 2
- HVLJWTVLYUVFJC-UHFFFAOYSA-N 2-[1-[3-(1-acetylpiperidin-4-yl)oxyphenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1CN(C(=O)C)CCC1OC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 HVLJWTVLYUVFJC-UHFFFAOYSA-N 0.000 description 2
- JBHDUXNXMAVMMD-UHFFFAOYSA-N 2-[5-(2-aminophenyl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound NC1=CC=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 JBHDUXNXMAVMMD-UHFFFAOYSA-N 0.000 description 2
- FHTHYQLXZUMHOH-UHFFFAOYSA-N 2-[5-(2-nitrophenyl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 FHTHYQLXZUMHOH-UHFFFAOYSA-N 0.000 description 2
- CZARCXXKFLNHRB-UHFFFAOYSA-N 2-[5-(3h-imidazo[4,5-c]pyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2NC3=CC=NC=C3N=2)=CN1C1=CC=CC=C1 CZARCXXKFLNHRB-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- MBMQYTQCUCQJEH-UHFFFAOYSA-N 3,5-dibromo-2-methoxypyridine Chemical compound COC1=NC=C(Br)C=C1Br MBMQYTQCUCQJEH-UHFFFAOYSA-N 0.000 description 2
- ZXIJHKPFDOGHRH-UHFFFAOYSA-N 3,5-diphenyl-1-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=CN1C1=CC=CC=N1 ZXIJHKPFDOGHRH-UHFFFAOYSA-N 0.000 description 2
- AEULIBWHJUAKRE-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-methoxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)Cl)=CC(C=2N=CC=CC=2)=C1 AEULIBWHJUAKRE-UHFFFAOYSA-N 0.000 description 2
- YAACRQMRCBUAEO-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(4-chlorophenyl)sulfanyl-1-pyridin-3-ylpyridin-2-one Chemical compound C1=CC(Cl)=CC=C1SC1=CN(C=2C=NC=CC=2)C(=O)C(C=2C(=CC=CC=2)Cl)=C1 YAACRQMRCBUAEO-UHFFFAOYSA-N 0.000 description 2
- XXGCGOZMWCUGQW-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(4-chlorophenyl)sulfinyl-1-pyridin-3-ylpyridin-2-one Chemical compound C1=CC(Cl)=CC=C1S(=O)C1=CN(C=2C=NC=CC=2)C(=O)C(C=2C(=CC=CC=2)Cl)=C1 XXGCGOZMWCUGQW-UHFFFAOYSA-N 0.000 description 2
- ZFEBPSVLGVSBOC-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(4-chlorophenyl)sulfonyl-1-pyridin-3-ylpyridin-2-one Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CN(C=2C=NC=CC=2)C(=O)C(C=2C(=CC=CC=2)Cl)=C1 ZFEBPSVLGVSBOC-UHFFFAOYSA-N 0.000 description 2
- YPIXMLSZYTWWFI-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(hydroxymethyl)-1-phenylpyridin-2-one Chemical compound O=C1N(C=2C=CC=CC=2)C=C(CO)C=C1C1=CC=CC=C1Cl YPIXMLSZYTWWFI-UHFFFAOYSA-N 0.000 description 2
- JAEVGQHKDBHHPM-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfanyl-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(Cl)=CC=C1SC(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 JAEVGQHKDBHHPM-UHFFFAOYSA-N 0.000 description 2
- PPFRNUJOYJTLRP-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfinyl-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(Cl)=CC=C1S(=O)C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 PPFRNUJOYJTLRP-UHFFFAOYSA-N 0.000 description 2
- ZIBJDUBXNZJSMB-UHFFFAOYSA-N 3-(6-chloropyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=NC(Cl)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ZIBJDUBXNZJSMB-UHFFFAOYSA-N 0.000 description 2
- SXSXFQVSHNSDRZ-UHFFFAOYSA-N 3-(6-methoxypyridin-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound COC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=N1 SXSXFQVSHNSDRZ-UHFFFAOYSA-N 0.000 description 2
- QVUYBKHSFJTICG-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QVUYBKHSFJTICG-UHFFFAOYSA-N 0.000 description 2
- XARYCNNFYJWDMF-UHFFFAOYSA-N 3-(6-methyl-1h-benzimidazol-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound N=1C2=CC(C)=CC=C2NC=1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 XARYCNNFYJWDMF-UHFFFAOYSA-N 0.000 description 2
- PNLNIKRPSUFJBD-UHFFFAOYSA-N 3-bromo-1,5-dipyridin-2-ylpyridin-2-one Chemical compound O=C1C(Br)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=N1 PNLNIKRPSUFJBD-UHFFFAOYSA-N 0.000 description 2
- MNAKGQPPTHUTAK-UHFFFAOYSA-N 3-bromo-5-nitro-1-phenylpyridin-2-one Chemical compound C1=C([N+](=O)[O-])C=C(Br)C(=O)N1C1=CC=CC=C1 MNAKGQPPTHUTAK-UHFFFAOYSA-N 0.000 description 2
- HCOPIUVJCIZALB-UHFFFAOYSA-N 3-bromopyridine-2-carbonitrile Chemical compound BrC1=CC=CN=C1C#N HCOPIUVJCIZALB-UHFFFAOYSA-N 0.000 description 2
- SPRHGLXBYNZUBD-UHFFFAOYSA-N 3-nitro-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C([N+](=O)[O-])=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 SPRHGLXBYNZUBD-UHFFFAOYSA-N 0.000 description 2
- BEXNRNCLRFMBCV-UHFFFAOYSA-N 3-nitro-1-phenylpyridin-2-one Chemical compound O=C1C([N+](=O)[O-])=CC=CN1C1=CC=CC=C1 BEXNRNCLRFMBCV-UHFFFAOYSA-N 0.000 description 2
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- MHNGZUMJWHZABH-UHFFFAOYSA-N 5-bromo-1-pyridin-2-ylpyridin-2-one Chemical compound C1=C(Br)C=CC(=O)N1C1=CC=CC=N1 MHNGZUMJWHZABH-UHFFFAOYSA-N 0.000 description 2
- IZKLQVNYCYAPCH-UHFFFAOYSA-N 5-bromo-2-methoxy-3-pyridin-2-ylpyridine Chemical compound COC1=NC=C(Br)C=C1C1=CC=CC=N1 IZKLQVNYCYAPCH-UHFFFAOYSA-N 0.000 description 2
- WAUPPDAXWKLNNU-UHFFFAOYSA-N 5-bromo-3-iodo-1h-pyridin-2-one Chemical compound BrC1=CNC(=O)C(I)=C1 WAUPPDAXWKLNNU-UHFFFAOYSA-N 0.000 description 2
- XPERZSKJGNUSHI-UHFFFAOYSA-N 5-bromo-3-iodopyridin-2-amine Chemical compound NC1=NC=C(Br)C=C1I XPERZSKJGNUSHI-UHFFFAOYSA-N 0.000 description 2
- AXLVAFBQYXYXQN-UHFFFAOYSA-N 5-bromo-3-nitro-1-phenylpyridin-2-one Chemical compound O=C1C([N+](=O)[O-])=CC(Br)=CN1C1=CC=CC=C1 AXLVAFBQYXYXQN-UHFFFAOYSA-N 0.000 description 2
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 2
- YMHILRBBRCVQJU-UHFFFAOYSA-N 5-nitro-1-phenylpyridin-2-one Chemical compound C1=C([N+](=O)[O-])C=CC(=O)N1C1=CC=CC=C1 YMHILRBBRCVQJU-UHFFFAOYSA-N 0.000 description 2
- CJHGRUUVFRQBQY-UHFFFAOYSA-N 5-phenyl-3-pyridin-2-yl-1h-pyridin-2-one Chemical compound O=C1NC=C(C=2C=CC=CC=2)C=C1C1=CC=CC=N1 CJHGRUUVFRQBQY-UHFFFAOYSA-N 0.000 description 2
- NHWKTZWOSIVHOL-UHFFFAOYSA-N 5-pyridin-2-yl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C=2N=CC=CC=2)=C1 NHWKTZWOSIVHOL-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 206010001014 Acute polyneuropathies Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 208000016621 Hearing disease Diseases 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 208000029067 Neuromyelitis optica spectrum disease Diseases 0.000 description 2
- 206010029333 Neurosis Diseases 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 241000169594 Paropsia Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 229940009098 aspartate Drugs 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 235000013405 beer Nutrition 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- MVXFLQKOCQKJNF-UHFFFAOYSA-N benzyl 4-[[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]methyl]piperidine-1-carboxylate Chemical compound C1CC(CN2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)CCN1C(=O)OCC1=CC=CC=C1 MVXFLQKOCQKJNF-UHFFFAOYSA-N 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 2
- 239000001354 calcium citrate Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 2
- 208000013677 cerebrovascular dementia Diseases 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 206010061811 demyelinating polyneuropathy Diseases 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 206010013990 dysuria Diseases 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000026045 iodination Effects 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- VYHKPWZYULRPRX-UHFFFAOYSA-L magnesium diperiodate Chemical compound [Mg++].[O-][I](=O)(=O)=O.[O-][I](=O)(=O)=O VYHKPWZYULRPRX-UHFFFAOYSA-L 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- KDBNUOFZWMPPKI-UHFFFAOYSA-N n-tert-butyl-4-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)(C)C)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 KDBNUOFZWMPPKI-UHFFFAOYSA-N 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 230000000324 neuroprotective effect Effects 0.000 description 2
- 208000015238 neurotic disease Diseases 0.000 description 2
- 230000036963 noncompetitive effect Effects 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- JGOFIIZNFBCVAV-UHFFFAOYSA-N periodic acid;hydrate Chemical compound O.OI(=O)(=O)=O JGOFIIZNFBCVAV-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- CFQJBWKKHCMCGJ-UHFFFAOYSA-N tributyl(pyridin-3-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN=C1 CFQJBWKKHCMCGJ-UHFFFAOYSA-N 0.000 description 2
- 235000013337 tricalcium citrate Nutrition 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- SOCAXRLFGRNEPK-IFZYUDKTSA-N (1r,3s,5r)-2-n-[1-carbamoyl-5-(cyanomethoxy)indol-3-yl]-3-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-2,3-dicarboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)NC1=CN(C2=CC=C(OCC#N)C=C21)C(=O)N)NCC1=CC=CC(Cl)=C1F SOCAXRLFGRNEPK-IFZYUDKTSA-N 0.000 description 1
- VRDAOVQZVXYRNH-UHFFFAOYSA-N (2-chloropyridin-3-yl)boronic acid Chemical compound OB(O)C1=CC=CN=C1Cl VRDAOVQZVXYRNH-UHFFFAOYSA-N 0.000 description 1
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 1
- DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- HGRWHBQLRXWSLV-DEOSSOPVSA-N (4s)-3'-(3,6-dihydro-2h-pyran-5-yl)-1'-fluoro-7'-(3-fluoropyridin-2-yl)spiro[5h-1,3-oxazole-4,5'-chromeno[2,3-c]pyridine]-2-amine Chemical compound C1OC(N)=N[C@]21C1=CC(C=3COCCC=3)=NC(F)=C1OC1=CC=C(C=3C(=CC=CN=3)F)C=C12 HGRWHBQLRXWSLV-DEOSSOPVSA-N 0.000 description 1
- NWKLWOGUAXAQGW-UHFFFAOYSA-N (6-chloropyridin-3-yl) acetate Chemical compound CC(=O)OC1=CC=C(Cl)N=C1 NWKLWOGUAXAQGW-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000005926 1,2-dimethylbutyloxy group Chemical group 0.000 description 1
- 125000005923 1,2-dimethylpropyloxy group Chemical group 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- CJXVCHZOUSZEQL-UHFFFAOYSA-N 1,3-diphenyl-5-(pyridine-2-carbonyl)pyridin-2-one Chemical compound C=1C=CC=NC=1C(=O)C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 CJXVCHZOUSZEQL-UHFFFAOYSA-N 0.000 description 1
- TYRFPEGGQFFLGC-UHFFFAOYSA-N 1-(1-benzyl-3,6-dihydro-2h-pyridin-5-yl)-3-bromo-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(Br)=CC(C=2N=CC=CC=2)=CN1C(C1)=CCCN1CC1=CC=CC=C1 TYRFPEGGQFFLGC-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- STHAMXUCSSZJQW-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(2-fluoropyridin-3-yl)-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C=2C(=NC=CC=2)F)=CC(C=2N=CC=CC=2)=C1 STHAMXUCSSZJQW-UHFFFAOYSA-N 0.000 description 1
- SYJCJFOFBGNDES-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(2-hydroxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound OC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=C(F)C=C1 SYJCJFOFBGNDES-UHFFFAOYSA-N 0.000 description 1
- QJKMOSJQNOEOST-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(2-methoxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound COC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=C(F)C=C1 QJKMOSJQNOEOST-UHFFFAOYSA-N 0.000 description 1
- LSNIALXTJNQQLI-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=C1 LSNIALXTJNQQLI-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- OCMPXVJMKPVOAZ-UHFFFAOYSA-N 1-phenyl-3,5-dipyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2N=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 OCMPXVJMKPVOAZ-UHFFFAOYSA-N 0.000 description 1
- GADFBVUTEBNSFU-UHFFFAOYSA-N 1-phenyl-3-(1-phenylbenzimidazol-2-yl)-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 GADFBVUTEBNSFU-UHFFFAOYSA-N 0.000 description 1
- FVNJJRVAFPJABV-UHFFFAOYSA-N 1-phenyl-3-(1-piperidin-4-ylbenzimidazol-2-yl)-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2N(C3=CC=CC=C3N=2)C2CCNCC2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 FVNJJRVAFPJABV-UHFFFAOYSA-N 0.000 description 1
- RYSHLMSQZJDGST-UHFFFAOYSA-N 1-phenyl-3-(2-phenylethynyl)-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C#CC=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 RYSHLMSQZJDGST-UHFFFAOYSA-N 0.000 description 1
- RROYOCUFHBJJAL-UHFFFAOYSA-N 1-phenyl-3-(3-phenyl-1,2,4-oxadiazol-5-yl)-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2ON=C(N=2)C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 RROYOCUFHBJJAL-UHFFFAOYSA-N 0.000 description 1
- ARBADSOSSKIQCB-UHFFFAOYSA-N 1-phenyl-3-pyrazin-2-yl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2N=CC=NC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ARBADSOSSKIQCB-UHFFFAOYSA-N 0.000 description 1
- FNBMQEANBBQMAF-UHFFFAOYSA-N 1-phenyl-3-pyridazin-3-yl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2N=NC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 FNBMQEANBBQMAF-UHFFFAOYSA-N 0.000 description 1
- GDYFZSCHWYGTKZ-UHFFFAOYSA-N 1-phenyl-3-pyridazin-4-yl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2C=NN=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 GDYFZSCHWYGTKZ-UHFFFAOYSA-N 0.000 description 1
- CTBDFLWZBWNKEF-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-(1,3-thiazol-2-yl)pyridin-2-one Chemical compound O=C1C(C=2SC=CN=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 CTBDFLWZBWNKEF-UHFFFAOYSA-N 0.000 description 1
- GBRSIPWQGXDUMU-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-(1,3-thiazol-4-yl)pyridin-2-one Chemical compound O=C1C(C=2N=CSC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 GBRSIPWQGXDUMU-UHFFFAOYSA-N 0.000 description 1
- TZXQCFJFHJSFMZ-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-(2-pyridin-2-ylethenyl)pyridin-2-one Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1C=CC1=CC=CC=N1 TZXQCFJFHJSFMZ-UHFFFAOYSA-N 0.000 description 1
- SLRKSBXXGJBHCA-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-(6-pyrrolidin-1-ylpyridin-3-yl)pyridin-2-one Chemical compound O=C1C(C=2C=NC(=CC=2)N2CCCC2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 SLRKSBXXGJBHCA-UHFFFAOYSA-N 0.000 description 1
- STAOZLZHJVMCCI-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-(pyridin-2-ylamino)pyridin-2-one Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1NC1=CC=CC=N1 STAOZLZHJVMCCI-UHFFFAOYSA-N 0.000 description 1
- ZLGFORZHBJOZPL-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]pyridin-2-one Chemical compound N=1C2=CC(C(F)(F)F)=CC=C2SC=1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ZLGFORZHBJOZPL-UHFFFAOYSA-N 0.000 description 1
- BLLFYTIASVHQER-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-pyridin-3-ylpyridin-2-one Chemical compound O=C1C(C=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 BLLFYTIASVHQER-UHFFFAOYSA-N 0.000 description 1
- VGVWMEFSYRZWHL-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-pyridin-4-ylpyridin-2-one Chemical compound O=C1C(C=2C=CN=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 VGVWMEFSYRZWHL-UHFFFAOYSA-N 0.000 description 1
- JOBXNCMMPSACLG-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-pyrimidin-2-ylpyridin-2-one Chemical compound O=C1C(C=2N=CC=CN=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 JOBXNCMMPSACLG-UHFFFAOYSA-N 0.000 description 1
- RSKQATJCMHLJOD-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-pyrimidin-4-ylpyridin-2-one Chemical compound O=C1C(C=2N=CN=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 RSKQATJCMHLJOD-UHFFFAOYSA-N 0.000 description 1
- PSXHIHFKGSJZPM-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-pyrimidin-5-ylpyridin-2-one Chemical compound O=C1C(C=2C=NC=NC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 PSXHIHFKGSJZPM-UHFFFAOYSA-N 0.000 description 1
- PSMBSUMUGNJKMO-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-pyrrol-1-ylpyridin-2-one Chemical compound O=C1C(N2C=CC=C2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 PSMBSUMUGNJKMO-UHFFFAOYSA-N 0.000 description 1
- HUZSJYQINGHCLB-UHFFFAOYSA-N 1-phenyl-5-pyridin-2-yl-3-quinolin-8-ylpyridin-2-one Chemical compound O=C1C(C=2C3=NC=CC=C3C=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 HUZSJYQINGHCLB-UHFFFAOYSA-N 0.000 description 1
- RBLXWIPBPPVLPU-UHFFFAOYSA-N 1-phenylpentane-1,4-dione Chemical compound CC(=O)CCC(=O)C1=CC=CC=C1 RBLXWIPBPPVLPU-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- TTYWSMWHPYKDEW-UHFFFAOYSA-N 1-pyridin-2-ylpyridin-2-one Chemical compound O=C1C=CC=CN1C1=CC=CC=N1 TTYWSMWHPYKDEW-UHFFFAOYSA-N 0.000 description 1
- BBHYMJRPJFVNPI-UHFFFAOYSA-N 2,3,5-tribromopyridine Chemical compound BrC1=CN=C(Br)C(Br)=C1 BBHYMJRPJFVNPI-UHFFFAOYSA-N 0.000 description 1
- WWJLJUAHQHXDGM-UHFFFAOYSA-N 2,5-dibromo-4-methylpyridine Chemical compound CC1=CC(Br)=NC=C1Br WWJLJUAHQHXDGM-UHFFFAOYSA-N 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- CJULECNSDMJARF-UHFFFAOYSA-N 2-(1-cyclopentyl-2-oxo-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1CCCC1 CJULECNSDMJARF-UHFFFAOYSA-N 0.000 description 1
- VYCZAYGGPNQENW-UHFFFAOYSA-N 2-(1-naphthalen-1-yl-2-oxo-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound C=1N(C=2C3=CC=CC=C3C=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=CC=1C1=CC=CC=N1 VYCZAYGGPNQENW-UHFFFAOYSA-N 0.000 description 1
- GGQSLBIBYNRLMT-UHFFFAOYSA-N 2-(1-naphthalen-2-yl-2-oxo-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound C=1N(C=2C=C3C=CC=CC3=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=CC=1C1=CC=CC=N1 GGQSLBIBYNRLMT-UHFFFAOYSA-N 0.000 description 1
- UBGYSLDXSFWRRT-UHFFFAOYSA-N 2-(2-oxo-1,5-dipyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=N1 UBGYSLDXSFWRRT-UHFFFAOYSA-N 0.000 description 1
- ZJDIVWKOBHRAEY-UHFFFAOYSA-N 2-(2-oxo-1,5-dipyridin-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=NC=CC=2)=CN1C1=CC=CN=C1 ZJDIVWKOBHRAEY-UHFFFAOYSA-N 0.000 description 1
- LJORHFLBTAKHRP-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyrazin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=NC=2)=CN1C1=CC=CC=C1 LJORHFLBTAKHRP-UHFFFAOYSA-N 0.000 description 1
- WRIQQNRLOAZUCM-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyridazin-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=NC=CC=2)=CN1C1=CC=CC=C1 WRIQQNRLOAZUCM-UHFFFAOYSA-N 0.000 description 1
- ZERDHJWZXCXAEV-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyridazin-4-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=NN=CC=2)=CN1C1=CC=CC=C1 ZERDHJWZXCXAEV-UHFFFAOYSA-N 0.000 description 1
- OMCYMMRAZDUHTJ-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzaldehyde Chemical compound O=CC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 OMCYMMRAZDUHTJ-UHFFFAOYSA-N 0.000 description 1
- QWXWKENPMNTMCA-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzamide Chemical compound NC(=O)C1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QWXWKENPMNTMCA-UHFFFAOYSA-N 0.000 description 1
- FKSLLXRNMPQCSJ-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)pyridine-3-carbonitrile Chemical compound O=C1C(C=2C(=CC=CN=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 FKSLLXRNMPQCSJ-UHFFFAOYSA-N 0.000 description 1
- FOCKQWMAYPOCNF-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyridin-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=NC=CC=2)=CN1C1=CC=CC=C1 FOCKQWMAYPOCNF-UHFFFAOYSA-N 0.000 description 1
- DCIMISQWWLKMKI-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyridin-4-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=CN=CC=2)=CN1C1=CC=CC=C1 DCIMISQWWLKMKI-UHFFFAOYSA-N 0.000 description 1
- BBHAWOMJLOILAI-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyrimidin-4-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CN=CC=2)=CN1C1=CC=CC=C1 BBHAWOMJLOILAI-UHFFFAOYSA-N 0.000 description 1
- QHFADEMAEKPSGO-UHFFFAOYSA-N 2-(2-oxo-1-phenyl-5-pyrimidin-5-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=NC=NC=2)=CN1C1=CC=CC=C1 QHFADEMAEKPSGO-UHFFFAOYSA-N 0.000 description 1
- VROCZKNXZCBEMW-UHFFFAOYSA-N 2-(2-oxo-1-piperidin-3-yl-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1CCCNC1 VROCZKNXZCBEMW-UHFFFAOYSA-N 0.000 description 1
- UUCCVMUOMSGEEO-UHFFFAOYSA-N 2-(2-oxo-1-pyridin-3-yl-5-quinolin-8-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C3=NC=CC=C3C=CC=2)=CN1C1=CC=CN=C1 UUCCVMUOMSGEEO-UHFFFAOYSA-N 0.000 description 1
- LIMAJPURYNDVHR-UHFFFAOYSA-N 2-(2-oxo-3-phenyl-5-pyridin-2-ylpyridin-1-yl)benzonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1C#N LIMAJPURYNDVHR-UHFFFAOYSA-N 0.000 description 1
- CRZHVMKYXBKPMB-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-1-pyridin-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=CC=CC=2)=CN1C1=CC=CN=C1 CRZHVMKYXBKPMB-UHFFFAOYSA-N 0.000 description 1
- AXNVHTVVUXAIAA-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-1-pyridin-3-ylpyridin-3-yl)pyridine-3-carbonitrile Chemical compound O=C1C(C=2C(=CC=CN=2)C#N)=CC(C=2C=CC=CC=2)=CN1C1=CC=CN=C1 AXNVHTVVUXAIAA-UHFFFAOYSA-N 0.000 description 1
- YZKAEKFPIPJUAE-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-3-pyridin-2-ylpyridin-1-yl)benzonitrile Chemical compound O=C1C(C=2N=CC=CC=2)=CC(C=2C=CC=CC=2)=CN1C1=CC=CC=C1C#N YZKAEKFPIPJUAE-UHFFFAOYSA-N 0.000 description 1
- XPTORAHWSFTGIF-UHFFFAOYSA-N 2-(2-oxo-5-pyridin-2-yl-1-quinolin-8-ylpyridin-3-yl)benzonitrile Chemical compound C=1N(C=2C3=NC=CC=C3C=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=CC=1C1=CC=CC=N1 XPTORAHWSFTGIF-UHFFFAOYSA-N 0.000 description 1
- TYPGGZHKTPBIOL-UHFFFAOYSA-N 2-(5-amino-2-oxo-1-phenylpyridin-3-yl)benzonitrile Chemical compound O=C1N(C=2C=CC=CC=2)C=C(N)C=C1C1=CC=CC=C1C#N TYPGGZHKTPBIOL-UHFFFAOYSA-N 0.000 description 1
- OTLMKEZITRUOTD-UHFFFAOYSA-N 2-(5-naphthalen-1-yl-2-oxo-1-pyridin-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C3=CC=CC=C3C=CC=2)=CN1C1=CC=CN=C1 OTLMKEZITRUOTD-UHFFFAOYSA-N 0.000 description 1
- SUKAIHJGDZVFNI-UHFFFAOYSA-N 2-(5-naphthalen-2-yl-2-oxo-1-pyridin-3-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C=C3C=CC=CC3=CC=2)=CN1C1=CC=CN=C1 SUKAIHJGDZVFNI-UHFFFAOYSA-N 0.000 description 1
- WPCDGUBJERWHIH-UHFFFAOYSA-N 2-(6-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2N=CC=CC=2)=CC(C=2C(=CC=CC=2)C#N)=CN1C1=CC=CC=C1 WPCDGUBJERWHIH-UHFFFAOYSA-N 0.000 description 1
- UMYMOSFVWFEHOK-UHFFFAOYSA-N 2-(6-oxo-5-phenyl-1-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2C(=CC=CC=2)C#N)=CN1C1=CC=CC=N1 UMYMOSFVWFEHOK-UHFFFAOYSA-N 0.000 description 1
- UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical compound OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- MTZOLTPNBYLIAB-UHFFFAOYSA-N 2-[(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)amino]benzonitrile Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1NC1=CC=CC=C1C#N MTZOLTPNBYLIAB-UHFFFAOYSA-N 0.000 description 1
- VQOZTVZHRDLEBW-UHFFFAOYSA-N 2-[1-(1-benzylpiperidin-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C1)CCCN1CC1=CC=CC=C1 VQOZTVZHRDLEBW-UHFFFAOYSA-N 0.000 description 1
- LDYONEXWIFKQCZ-UHFFFAOYSA-N 2-[1-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1C#N LDYONEXWIFKQCZ-UHFFFAOYSA-N 0.000 description 1
- SVNZFPJPCTYPMR-UHFFFAOYSA-N 2-[1-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)piperidin-4-yl]benzonitrile Chemical compound O=C1C(N2CCC(CC2)C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 SVNZFPJPCTYPMR-UHFFFAOYSA-N 0.000 description 1
- QDWLKQDRLSHCQO-UHFFFAOYSA-N 2-[1-(3-acetylphenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CC(=O)C1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 QDWLKQDRLSHCQO-UHFFFAOYSA-N 0.000 description 1
- GDQVXOXDIDKEGP-UHFFFAOYSA-N 2-[1-(3-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC(C#N)=C1 GDQVXOXDIDKEGP-UHFFFAOYSA-N 0.000 description 1
- WJKGNHGCQBHHNP-UHFFFAOYSA-N 2-[1-(4-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=C(C#N)C=C1 WJKGNHGCQBHHNP-UHFFFAOYSA-N 0.000 description 1
- UNEJYMOVVWSWIF-UHFFFAOYSA-N 2-[1-(4-methyl-3-nitrophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 UNEJYMOVVWSWIF-UHFFFAOYSA-N 0.000 description 1
- WQICGROGZZWOKU-UHFFFAOYSA-N 2-[1-(4-nitrophenyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 WQICGROGZZWOKU-UHFFFAOYSA-N 0.000 description 1
- PDSPXEZPYKMWED-UHFFFAOYSA-N 2-[1-(6-ethylpyridin-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=NC(CC)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 PDSPXEZPYKMWED-UHFFFAOYSA-N 0.000 description 1
- PVECTQZDJBLFIC-UHFFFAOYSA-N 2-[1-(6-ethylsulfonylpyridin-3-yl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=NC(S(=O)(=O)CC)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 PVECTQZDJBLFIC-UHFFFAOYSA-N 0.000 description 1
- WIYQFARKYOPQEN-UHFFFAOYSA-N 2-[1-(cyclopentylmethyl)-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1CC1CCCC1 WIYQFARKYOPQEN-UHFFFAOYSA-N 0.000 description 1
- JZZKWUIPDCYWCM-UHFFFAOYSA-N 2-[1-[(1-acetylpiperidin-4-yl)methyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1CN(C(=O)C)CCC1CN1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 JZZKWUIPDCYWCM-UHFFFAOYSA-N 0.000 description 1
- CAAGDMRCEBQTNK-UHFFFAOYSA-N 2-[1-[(1-benzoylpiperidin-4-yl)methyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C=1C=CC=CC=1C(=O)N(CC1)CCC1CN(C1=O)C=C(C=2N=CC=CC=2)C=C1C1=CC=CC=C1C#N CAAGDMRCEBQTNK-UHFFFAOYSA-N 0.000 description 1
- JYISAABRCDNBSA-UHFFFAOYSA-N 2-[1-[(1-benzylpiperidin-4-yl)methyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1CC(CC1)CCN1CC1=CC=CC=C1 JYISAABRCDNBSA-UHFFFAOYSA-N 0.000 description 1
- GXAIWXLGOFZCTO-UHFFFAOYSA-N 2-[1-[(1-methylpiperidin-4-yl)methyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1CN(C)CCC1CN1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 GXAIWXLGOFZCTO-UHFFFAOYSA-N 0.000 description 1
- OCWYNXPIFWLNLY-UHFFFAOYSA-N 2-[1-[(1-methylsulfonylpiperidin-4-yl)methyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1CN(S(=O)(=O)C)CCC1CN1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 OCWYNXPIFWLNLY-UHFFFAOYSA-N 0.000 description 1
- RSIYUKNQBVZLEO-UHFFFAOYSA-N 2-[1-[2-[(dimethylamino)methyl]phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CN(C)CC1=CC=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 RSIYUKNQBVZLEO-UHFFFAOYSA-N 0.000 description 1
- JFOPCFILDDHOJK-UHFFFAOYSA-N 2-[1-[2-[3-(dimethylamino)propoxy]phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CN(C)CCCOC1=CC=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 JFOPCFILDDHOJK-UHFFFAOYSA-N 0.000 description 1
- SYVKVYHCQHKKFQ-UHFFFAOYSA-N 2-[1-[3-(1-benzoylpiperidin-4-yl)oxyphenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C=1C=CC=CC=1C(=O)N(CC1)CCC1OC(C=1)=CC=CC=1N(C1=O)C=C(C=2N=CC=CC=2)C=C1C1=CC=CC=C1C#N SYVKVYHCQHKKFQ-UHFFFAOYSA-N 0.000 description 1
- LLCRHIVGFWMCPU-UHFFFAOYSA-N 2-[1-[3-(1-benzylpiperidin-4-yl)oxyphenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CC=CC=1OC(CC1)CCN1CC1=CC=CC=C1 LLCRHIVGFWMCPU-UHFFFAOYSA-N 0.000 description 1
- LOIDJCDQKKVWPA-UHFFFAOYSA-N 2-[1-[3-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 LOIDJCDQKKVWPA-UHFFFAOYSA-N 0.000 description 1
- VXQMJLXBYHGHHV-UHFFFAOYSA-N 2-[1-[3-(2-morpholin-4-ylethoxy)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CC=CC=1OCCN1CCOCC1 VXQMJLXBYHGHHV-UHFFFAOYSA-N 0.000 description 1
- JDLZLUDSNBAOJA-UHFFFAOYSA-N 2-[1-[3-[(4-acetylpiperazin-1-yl)methyl]phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1CN(C(=O)C)CCN1CC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 JDLZLUDSNBAOJA-UHFFFAOYSA-N 0.000 description 1
- VCEACWVJRLMQLN-UHFFFAOYSA-N 2-[1-[3-[2-(diethylamino)ethoxy]phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CCN(CC)CCOC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 VCEACWVJRLMQLN-UHFFFAOYSA-N 0.000 description 1
- FFDRPQQWGJPRKM-UHFFFAOYSA-N 2-[1-[3-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CC(C)N(C(C)C)CCOC1=CC=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 FFDRPQQWGJPRKM-UHFFFAOYSA-N 0.000 description 1
- ZWWDUVKOTZMCIS-UHFFFAOYSA-N 2-[1-[4-(hydroxymethyl)phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(CO)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 ZWWDUVKOTZMCIS-UHFFFAOYSA-N 0.000 description 1
- IREDRYJBNAWXCN-UHFFFAOYSA-N 2-[1-[4-[(dimethylamino)methyl]phenyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=CC(CN(C)C)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 IREDRYJBNAWXCN-UHFFFAOYSA-N 0.000 description 1
- CXWJWMFSCOAAMG-UHFFFAOYSA-N 2-[1-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-3-yl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound CC(C)(C)[Si](C)(C)OCC1=CN=CC(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)=C1 CXWJWMFSCOAAMG-UHFFFAOYSA-N 0.000 description 1
- YKZXTELAQCVAND-UHFFFAOYSA-N 2-[1-[6-(2-hydroxyethoxy)pyridin-3-yl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1=NC(OCCO)=CC=C1N1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 YKZXTELAQCVAND-UHFFFAOYSA-N 0.000 description 1
- JOMCTYCPCQAVAA-UHFFFAOYSA-N 2-[1-[6-(4-benzylpiperazin-1-yl)pyridin-3-yl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=N1)=CC=C1N(CC1)CCN1CC1=CC=CC=C1 JOMCTYCPCQAVAA-UHFFFAOYSA-N 0.000 description 1
- BGNLUFYNWRRFDX-UHFFFAOYSA-N 2-[1-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C1CN(C)CCN1C1=CC=C(N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)C=N1 BGNLUFYNWRRFDX-UHFFFAOYSA-N 0.000 description 1
- MFCXSICKYLPRKZ-UHFFFAOYSA-N 2-[1-[[1-(benzenesulfonyl)piperidin-4-yl]methyl]-2-oxo-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1CC(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 MFCXSICKYLPRKZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KYWNKKBKXWWDGV-UHFFFAOYSA-N 2-[2-oxo-1-(1-phenylethyl)-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound C(#N)C1=C(C=CC=C1)C=1C(N(C=C(C1)C1=NC=CC=C1)C(C)C1=CC=CC=C1)=O KYWNKKBKXWWDGV-UHFFFAOYSA-N 0.000 description 1
- KDUNQKMBIWJXIE-UHFFFAOYSA-N 2-[2-oxo-1-(3-phenylmethoxyphenyl)-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CC=CC=1OCC1=CC=CC=C1 KDUNQKMBIWJXIE-UHFFFAOYSA-N 0.000 description 1
- DXRBWXJOIFYTNT-UHFFFAOYSA-N 2-[2-oxo-1-(phenylmethoxymethyl)-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1COCC1=CC=CC=C1 DXRBWXJOIFYTNT-UHFFFAOYSA-N 0.000 description 1
- XSHHLFXVBHBAQA-UHFFFAOYSA-N 2-[2-oxo-1-[3-(4-piperidin-1-ylbutoxy)phenyl]-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CC=CC=1OCCCCN1CCCCC1 XSHHLFXVBHBAQA-UHFFFAOYSA-N 0.000 description 1
- BWTATTXEUCPZBP-UHFFFAOYSA-N 2-[2-oxo-1-[6-(2-phenylmethoxyethoxy)pyridin-3-yl]-5-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=N1)=CC=C1OCCOCC1=CC=CC=C1 BWTATTXEUCPZBP-UHFFFAOYSA-N 0.000 description 1
- AZUJASVKHIHZFO-UHFFFAOYSA-N 2-[2-oxo-1-phenyl-5-(1,3-thiazol-4-yl)pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CSC=2)=CN1C1=CC=CC=C1 AZUJASVKHIHZFO-UHFFFAOYSA-N 0.000 description 1
- INILDJQTNATUMO-UHFFFAOYSA-N 2-[2-oxo-1-phenyl-5-(1-phenylbenzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CN1C1=CC=CC=C1 INILDJQTNATUMO-UHFFFAOYSA-N 0.000 description 1
- FVQORONEJQKJFR-UHFFFAOYSA-N 2-[2-oxo-1-phenyl-5-(1-pyridin-4-ylbenzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CN=CC=2)=CN1C1=CC=CC=C1 FVQORONEJQKJFR-UHFFFAOYSA-N 0.000 description 1
- CADXXMRVYHLQKU-UHFFFAOYSA-N 2-[2-oxo-1-phenyl-5-(2-pyridin-2-ylethenyl)pyridin-3-yl]benzonitrile Chemical compound C=1N(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=CC=1C=CC1=CC=CC=N1 CADXXMRVYHLQKU-UHFFFAOYSA-N 0.000 description 1
- UYFIQSVQFVKFCM-UHFFFAOYSA-N 2-[2-oxo-1-phenyl-5-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2ON=C(N=2)C=2C=CC=CC=2)=CN1C1=CC=CC=C1 UYFIQSVQFVKFCM-UHFFFAOYSA-N 0.000 description 1
- HCTDSPJRESEWMZ-UHFFFAOYSA-N 2-[2-oxo-1-phenyl-5-[5-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]benzonitrile Chemical compound N1=CC(C(F)(F)F)=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 HCTDSPJRESEWMZ-UHFFFAOYSA-N 0.000 description 1
- BTCZBKGWSPORSG-UHFFFAOYSA-N 2-[2-oxo-5-(3-oxocyclohexen-1-yl)-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1CCCC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=C1 BTCZBKGWSPORSG-UHFFFAOYSA-N 0.000 description 1
- RETHIGXEJPKZQZ-UHFFFAOYSA-N 2-[2-oxo-5-pyridin-2-yl-1-(1h-pyrrol-3-yl)pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C=1C=CNC=1 RETHIGXEJPKZQZ-UHFFFAOYSA-N 0.000 description 1
- TZKBXZJJBVQDBP-UHFFFAOYSA-N 2-[2-oxo-5-pyridin-2-yl-1-(6-pyrrolidin-1-ylpyridin-3-yl)pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=N1)=CC=C1N1CCCC1 TZKBXZJJBVQDBP-UHFFFAOYSA-N 0.000 description 1
- GNCBHCMFBLHDMD-UHFFFAOYSA-N 2-[2-oxo-5-pyridin-2-yl-1-[3-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CC=CC=1OCCN1CCCC1 GNCBHCMFBLHDMD-UHFFFAOYSA-N 0.000 description 1
- WPFOSHJXMCAZAI-UHFFFAOYSA-N 2-[2-oxo-5-pyridin-2-yl-1-[3-(pyrrolidin-1-ylmethyl)phenyl]pyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CC=CC=1CN1CCCC1 WPFOSHJXMCAZAI-UHFFFAOYSA-N 0.000 description 1
- OZUJUQBVZPUXDT-UHFFFAOYSA-N 2-[5-(1-methyl-3,6-dihydro-2h-pyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound CN1CC=CCC1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 OZUJUQBVZPUXDT-UHFFFAOYSA-N 0.000 description 1
- CGUDTAFYBXUHKB-UHFFFAOYSA-N 2-[5-(1-methylpiperidin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound CN1CCCCC1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 CGUDTAFYBXUHKB-UHFFFAOYSA-N 0.000 description 1
- WVZZAFNBZDWMAR-UHFFFAOYSA-N 2-[5-(1-methylpyrazol-4-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound C1=NN(C)C=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 WVZZAFNBZDWMAR-UHFFFAOYSA-N 0.000 description 1
- OCVJSBAQDUDBST-UHFFFAOYSA-N 2-[5-(1h-benzimidazol-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2NC3=CC=CC=C3N=2)=CN1C1=CC=CC=C1 OCVJSBAQDUDBST-UHFFFAOYSA-N 0.000 description 1
- YPMLDAHSPQSHHE-UHFFFAOYSA-N 2-[5-(2,3-dihydro-1,4-dioxin-5-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2OCCOC=2)=CN1C1=CC=CC=C1 YPMLDAHSPQSHHE-UHFFFAOYSA-N 0.000 description 1
- AFRYYSYVWHFASU-UHFFFAOYSA-N 2-[5-(2,4-dimethoxypyrimidin-5-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound COC1=NC(OC)=NC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 AFRYYSYVWHFASU-UHFFFAOYSA-N 0.000 description 1
- BGVAZWHWNRMMCN-UHFFFAOYSA-N 2-[5-(2-cyanophenyl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C(=CC=CC=2)C#N)=CN1C1=CC=CC=C1 BGVAZWHWNRMMCN-UHFFFAOYSA-N 0.000 description 1
- ZUAYLKNBQAKHOH-UHFFFAOYSA-N 2-[5-(2-cyanophenyl)-2-oxo-1-pyridin-2-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2C(=CC=CC=2)C#N)=CN1C1=CC=CC=N1 ZUAYLKNBQAKHOH-UHFFFAOYSA-N 0.000 description 1
- HDEOXZOQUIGHMC-UHFFFAOYSA-N 2-[5-(2-methoxyphenyl)-2-oxo-1-pyridin-3-ylpyridin-3-yl]benzonitrile Chemical compound COC1=CC=CC=C1C1=CN(C=2C=NC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 HDEOXZOQUIGHMC-UHFFFAOYSA-N 0.000 description 1
- INVIRGZOYNPPGY-UHFFFAOYSA-N 2-[5-(3-aminopyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound NC1=CC=CN=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 INVIRGZOYNPPGY-UHFFFAOYSA-N 0.000 description 1
- FGGHYVHAIGEXRJ-UHFFFAOYSA-N 2-[5-(3-methylpyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound CC1=CC=CN=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 FGGHYVHAIGEXRJ-UHFFFAOYSA-N 0.000 description 1
- UPOVVAJMRPMUEH-UHFFFAOYSA-N 2-[5-(3-nitropyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound [O-][N+](=O)C1=CC=CN=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 UPOVVAJMRPMUEH-UHFFFAOYSA-N 0.000 description 1
- AXOVZXUSDUPDRO-UHFFFAOYSA-N 2-[5-(4-methyl-1h-benzimidazol-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N=1C=2C(C)=CC=CC=2NC=1C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1C#N AXOVZXUSDUPDRO-UHFFFAOYSA-N 0.000 description 1
- HGTNQGXOIVMPKX-UHFFFAOYSA-N 2-[5-(4-methylimidazo[4,5-b]pyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N1=C2N(C)C=CC=C2N=C1C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1C#N HGTNQGXOIVMPKX-UHFFFAOYSA-N 0.000 description 1
- RKLYTZVMTSFDQJ-UHFFFAOYSA-N 2-[5-(4-methylpyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound CC1=CC=NC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=C1 RKLYTZVMTSFDQJ-UHFFFAOYSA-N 0.000 description 1
- SXXCQMZHANMUGS-UHFFFAOYSA-N 2-[5-(5,6-dichloro-1h-benzimidazol-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N1C=2C=C(Cl)C(Cl)=CC=2N=C1C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1C#N SXXCQMZHANMUGS-UHFFFAOYSA-N 0.000 description 1
- XRKNDSDPEDELSD-UHFFFAOYSA-N 2-[5-(5-aminopyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N1=CC(N)=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 XRKNDSDPEDELSD-UHFFFAOYSA-N 0.000 description 1
- ANABGQBVYPBTIS-UHFFFAOYSA-N 2-[5-(5-hydroxypyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N1=CC(O)=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 ANABGQBVYPBTIS-UHFFFAOYSA-N 0.000 description 1
- IKQYPVDIISPVKO-UHFFFAOYSA-N 2-[5-(5-methoxypyridin-3-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound COC1=CN=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=C1 IKQYPVDIISPVKO-UHFFFAOYSA-N 0.000 description 1
- NRLUSZRDEZJOIW-UHFFFAOYSA-N 2-[5-(5-nitropyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N1=CC([N+](=O)[O-])=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 NRLUSZRDEZJOIW-UHFFFAOYSA-N 0.000 description 1
- PYVOGFYBFQSKNV-UHFFFAOYSA-N 2-[5-(6-aminopyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound NC1=CC=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=N1 PYVOGFYBFQSKNV-UHFFFAOYSA-N 0.000 description 1
- JDKJHOQXKCUHOO-UHFFFAOYSA-N 2-[5-(6-methoxy-1h-benzimidazol-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N=1C2=CC(OC)=CC=C2NC=1C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1C#N JDKJHOQXKCUHOO-UHFFFAOYSA-N 0.000 description 1
- DCLXJYDAAVHLKL-UHFFFAOYSA-N 2-[5-(6-methoxypyridin-3-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound C1=NC(OC)=CC=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 DCLXJYDAAVHLKL-UHFFFAOYSA-N 0.000 description 1
- QKRHFYCOFRRCJA-UHFFFAOYSA-N 2-[5-(6-methyl-1h-benzimidazol-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound N=1C2=CC(C)=CC=C2NC=1C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1C#N QKRHFYCOFRRCJA-UHFFFAOYSA-N 0.000 description 1
- XUYIERGENNCVQI-UHFFFAOYSA-N 2-[5-(6-morpholin-4-ylpyridin-2-yl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=C(C=CC=2)N2CCOCC2)=CN1C1=CC=CC=C1 XUYIERGENNCVQI-UHFFFAOYSA-N 0.000 description 1
- HDSWXJWAMYALCE-UHFFFAOYSA-N 2-[5-(benzylamino)-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound C=1N(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=CC=1NCC1=CC=CC=C1 HDSWXJWAMYALCE-UHFFFAOYSA-N 0.000 description 1
- DHIDOIYGPLLABL-UHFFFAOYSA-N 2-[5-[1-(1-benzylpiperidin-4-yl)benzimidazol-2-yl]-2-oxo-1-phenylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N(C3=CC=CC=C3N=2)C2CCN(CC=3C=CC=CC=3)CC2)=CN1C1=CC=CC=C1 DHIDOIYGPLLABL-UHFFFAOYSA-N 0.000 description 1
- VNKITSVVXPROST-UHFFFAOYSA-N 2-[5-[3-(benzenesulfonyl)-1h-indol-2-yl]-2-oxo-1-pyridin-3-ylpyridin-3-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C2=C(C3=CC=CC=C3N2)S(=O)(=O)C=2C=CC=CC=2)=CN1C1=CC=CN=C1 VNKITSVVXPROST-UHFFFAOYSA-N 0.000 description 1
- VUMZNLOQJGKGNE-UHFFFAOYSA-N 2-amino-5-methylbenzenethiol Chemical compound CC1=CC=C(N)C(S)=C1 VUMZNLOQJGKGNE-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- 125000003858 2-ethylbutoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])O*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000005924 2-methylpentyloxy group Chemical group 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 1
- BGRXBNZMPMGLQI-UHFFFAOYSA-N 2-octyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC BGRXBNZMPMGLQI-UHFFFAOYSA-N 0.000 description 1
- LNTJUZJONXEAJG-UHFFFAOYSA-N 2-oxo-n',1-diphenyl-5-pyridin-2-ylpyridine-3-carbohydrazide Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1C(=O)NNC1=CC=CC=C1 LNTJUZJONXEAJG-UHFFFAOYSA-N 0.000 description 1
- ATYRGNYBPIAGEI-UHFFFAOYSA-N 2-oxo-n,1-diphenyl-5-pyridin-2-ylpyridine-3-carboxamide Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1C(=O)NC1=CC=CC=C1 ATYRGNYBPIAGEI-UHFFFAOYSA-N 0.000 description 1
- FRICBZWJFIRJOB-UHFFFAOYSA-N 2-piperazin-1-ylbenzonitrile Chemical compound N#CC1=CC=CC=C1N1CCNCC1 FRICBZWJFIRJOB-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- RZHBZSKPYJXXQE-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2SC3=CC=CC=C3N=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 RZHBZSKPYJXXQE-UHFFFAOYSA-N 0.000 description 1
- SFKKHPJOCRJOMK-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2OC3=CC=CC=C3N=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 SFKKHPJOCRJOMK-UHFFFAOYSA-N 0.000 description 1
- RXLYZWKVWAAJPW-UHFFFAOYSA-N 3-(1-adamantyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C23CC4CC(CC(C4)C2)C3)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 RXLYZWKVWAAJPW-UHFFFAOYSA-N 0.000 description 1
- QZTJJXKYPWNPDB-UHFFFAOYSA-N 3-(1-adamantylamino)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(NC23CC4CC(CC(C4)C2)C3)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QZTJJXKYPWNPDB-UHFFFAOYSA-N 0.000 description 1
- KBMSGGYYUBOLDJ-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2NC3=CC=CC=C3N=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 KBMSGGYYUBOLDJ-UHFFFAOYSA-N 0.000 description 1
- GZFRPOBNLQQQBB-UHFFFAOYSA-N 3-(2,2-dichloro-1-hydroxyheptyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C(O)C(Cl)(Cl)CCCCC)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 GZFRPOBNLQQQBB-UHFFFAOYSA-N 0.000 description 1
- JPQGYORYUQIISF-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-dioxin-5-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2OCCOC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 JPQGYORYUQIISF-UHFFFAOYSA-N 0.000 description 1
- YUEDQHPZMWJQED-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound ClC1=CC(Cl)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 YUEDQHPZMWJQED-UHFFFAOYSA-N 0.000 description 1
- YYXRZCZLEQLUSG-UHFFFAOYSA-N 3-(2,5-dimethylpyrrol-1-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound CC1=CC=C(C)N1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 YYXRZCZLEQLUSG-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- XCXVMIAKKSJLPZ-UHFFFAOYSA-N 3-(2-acetylphenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound CC(=O)C1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 XCXVMIAKKSJLPZ-UHFFFAOYSA-N 0.000 description 1
- AADNBFJPPVHCJB-UHFFFAOYSA-N 3-(2-adamantyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C2C3CC4CC(C3)CC2C4)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 AADNBFJPPVHCJB-UHFFFAOYSA-N 0.000 description 1
- QSSBULVYXONWDD-UHFFFAOYSA-N 3-(2-aminophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound NC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QSSBULVYXONWDD-UHFFFAOYSA-N 0.000 description 1
- YYKGSEHGOCTNED-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-phenyl-5-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]pyridin-2-one Chemical compound N=1C2=CC(C(F)(F)F)=CC=C2SC=1C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1Cl YYKGSEHGOCTNED-UHFFFAOYSA-N 0.000 description 1
- CLCXDNTWHAIPRX-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(phenoxymethyl)-1-phenylpyridin-2-one Chemical compound ClC1=CC=CC=C1C(C1=O)=CC(COC=2C=CC=CC=2)=CN1C1=CC=CC=C1 CLCXDNTWHAIPRX-UHFFFAOYSA-N 0.000 description 1
- DSFRODNYVFDMED-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-cyclohexyl-1-phenylpyridin-2-one Chemical compound ClC1=CC=CC=C1C(C1=O)=CC(C2CCCCC2)=CN1C1=CC=CC=C1 DSFRODNYVFDMED-UHFFFAOYSA-N 0.000 description 1
- GJOCLAAJFGTGRV-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-1-(4-methylsulfanylphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(SC)=CC=C1N1C(=O)C(C=2C(=NC=CC=2)F)=CC(C=2N=CC=CC=2)=C1 GJOCLAAJFGTGRV-UHFFFAOYSA-N 0.000 description 1
- LPTRRIGMVNTZAU-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-1-(4-methylsulfonylphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C(C=2C(=NC=CC=2)F)=CC(C=2N=CC=CC=2)=C1 LPTRRIGMVNTZAU-UHFFFAOYSA-N 0.000 description 1
- NGYRLLIOEFUTPW-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-1-pyridin-3-yl-5-pyrimidin-2-ylpyridin-2-one Chemical compound FC1=NC=CC=C1C(C1=O)=CC(C=2N=CC=CN=2)=CN1C1=CC=CN=C1 NGYRLLIOEFUTPW-UHFFFAOYSA-N 0.000 description 1
- OOLTYILVCQHZJJ-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-5-phenyl-1-pyridin-3-ylpyridin-2-one Chemical compound FC1=NC=CC=C1C(C1=O)=CC(C=2C=CC=CC=2)=CN1C1=CC=CN=C1 OOLTYILVCQHZJJ-UHFFFAOYSA-N 0.000 description 1
- BFPOTWPKWPOMMN-UHFFFAOYSA-N 3-(2-fluoropyridin-3-yl)-5-pyridin-2-yl-1-pyrimidin-5-ylpyridin-2-one Chemical compound FC1=NC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CN=CN=C1 BFPOTWPKWPOMMN-UHFFFAOYSA-N 0.000 description 1
- FDNWYUONOKRJMK-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound OC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 FDNWYUONOKRJMK-UHFFFAOYSA-N 0.000 description 1
- RBCTZAFVHDBCAO-UHFFFAOYSA-N 3-(2-methoxyphenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound COC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 RBCTZAFVHDBCAO-UHFFFAOYSA-N 0.000 description 1
- LLGZBRFGRAWEET-UHFFFAOYSA-N 3-(2-methoxyphenyl)-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound COC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 LLGZBRFGRAWEET-UHFFFAOYSA-N 0.000 description 1
- ITZSWOZYEGKASO-UHFFFAOYSA-N 3-(2-methyl-5-phenylpyrrol-1-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1N1C(C)=CC=C1C1=CC=CC=C1 ITZSWOZYEGKASO-UHFFFAOYSA-N 0.000 description 1
- DZHLAHOIYQLAQU-UHFFFAOYSA-N 3-(2-methylphenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound CC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 DZHLAHOIYQLAQU-UHFFFAOYSA-N 0.000 description 1
- POQXROXRTVUBHE-UHFFFAOYSA-N 3-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C=C(C=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 POQXROXRTVUBHE-UHFFFAOYSA-N 0.000 description 1
- ZFYTZKKCZVTEGQ-UHFFFAOYSA-N 3-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)pyridine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ZFYTZKKCZVTEGQ-UHFFFAOYSA-N 0.000 description 1
- ADZNLYKWRFRXBN-UHFFFAOYSA-N 3-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)thiophene-2-carbonitrile Chemical compound O=C1C(C2=C(SC=C2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ADZNLYKWRFRXBN-UHFFFAOYSA-N 0.000 description 1
- CCSPXFNHBWYSLB-UHFFFAOYSA-N 3-(2-oxo-1-pyridin-3-yl-5-pyrimidin-2-ylpyridin-3-yl)pyridine-2-carbonitrile Chemical compound O=C1C(C=2C(=NC=CC=2)C#N)=CC(C=2N=CC=CN=2)=CN1C1=CC=CN=C1 CCSPXFNHBWYSLB-UHFFFAOYSA-N 0.000 description 1
- RTIRYKDWQJJJPH-UHFFFAOYSA-N 3-(2-oxo-5-pyridin-2-yl-1-pyridin-3-ylpyridin-3-yl)pyridine-2-carbonitrile Chemical compound O=C1C(C=2C(=NC=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 RTIRYKDWQJJJPH-UHFFFAOYSA-N 0.000 description 1
- PLYVIVXHJZVWLF-UHFFFAOYSA-N 3-(2-oxo-5-pyridin-2-yl-1-pyridin-3-ylpyridin-3-yl)thiophene-2-carbaldehyde Chemical compound S1C=CC(C=2C(N(C=3C=NC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1C=O PLYVIVXHJZVWLF-UHFFFAOYSA-N 0.000 description 1
- MVOOIVJKHPZTEW-UHFFFAOYSA-N 3-(3-aminophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound NC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 MVOOIVJKHPZTEW-UHFFFAOYSA-N 0.000 description 1
- GPFGOUDKDQZNRC-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound ClC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 GPFGOUDKDQZNRC-UHFFFAOYSA-N 0.000 description 1
- XFNJYCJCHQWPJF-UHFFFAOYSA-N 3-(3-fluorophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound FC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 XFNJYCJCHQWPJF-UHFFFAOYSA-N 0.000 description 1
- GDTFBTWKVFAQQQ-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound OC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 GDTFBTWKVFAQQQ-UHFFFAOYSA-N 0.000 description 1
- ZBDFTJGMHCMNNO-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound COC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 ZBDFTJGMHCMNNO-UHFFFAOYSA-N 0.000 description 1
- DASSHPWJFXIELZ-UHFFFAOYSA-N 3-(3-nitrophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound [O-][N+](=O)C1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 DASSHPWJFXIELZ-UHFFFAOYSA-N 0.000 description 1
- VVUGARIBQUNRMT-UHFFFAOYSA-N 3-(3h-imidazo[4,5-c]pyridin-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2NC3=CC=NC=C3N=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 VVUGARIBQUNRMT-UHFFFAOYSA-N 0.000 description 1
- YCYYWNLAJOWPFB-UHFFFAOYSA-N 3-(4-aminophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(N)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 YCYYWNLAJOWPFB-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- QZIJXMBHEVMECD-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(Cl)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QZIJXMBHEVMECD-UHFFFAOYSA-N 0.000 description 1
- SCJGZDDOGOOPDZ-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 SCJGZDDOGOOPDZ-UHFFFAOYSA-N 0.000 description 1
- MSSPAWXVRSQXPS-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(F)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 MSSPAWXVRSQXPS-UHFFFAOYSA-N 0.000 description 1
- VTEOCZPAMRVYKL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(O)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 VTEOCZPAMRVYKL-UHFFFAOYSA-N 0.000 description 1
- ZILOJVYQJRVBPI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(OC)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ZILOJVYQJRVBPI-UHFFFAOYSA-N 0.000 description 1
- SPMYOKHEZRNZEO-UHFFFAOYSA-N 3-(4-nitrophenyl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 SPMYOKHEZRNZEO-UHFFFAOYSA-N 0.000 description 1
- CVJGGZCDLVAUAJ-UHFFFAOYSA-N 3-(5,6-dichloro-1h-benzimidazol-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound N1C=2C=C(Cl)C(Cl)=CC=2N=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 CVJGGZCDLVAUAJ-UHFFFAOYSA-N 0.000 description 1
- VSIMVSMGNLTZLI-UHFFFAOYSA-N 3-(5-chloro-1,3-benzoxazol-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound N=1C2=CC(Cl)=CC=C2OC=1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 VSIMVSMGNLTZLI-UHFFFAOYSA-N 0.000 description 1
- NKSXERSUWMQAAO-UHFFFAOYSA-N 3-(6-chloro-1h-benzimidazol-2-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound N1C2=CC(Cl)=CC=C2N=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 NKSXERSUWMQAAO-UHFFFAOYSA-N 0.000 description 1
- KDONIQREHQYSFB-UHFFFAOYSA-N 3-(6-ethylpyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=NC(CC)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 KDONIQREHQYSFB-UHFFFAOYSA-N 0.000 description 1
- MXFZCTDWGFTCKZ-UHFFFAOYSA-N 3-(6-ethylsulfanylpyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=NC(SCC)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 MXFZCTDWGFTCKZ-UHFFFAOYSA-N 0.000 description 1
- JWEBRESOUYNZFF-UHFFFAOYSA-N 3-(6-ethylsulfinylpyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=NC(S(=O)CC)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 JWEBRESOUYNZFF-UHFFFAOYSA-N 0.000 description 1
- PKJCKSSHJWIVNQ-UHFFFAOYSA-N 3-(6-ethylsulfonylpyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=NC(S(=O)(=O)CC)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 PKJCKSSHJWIVNQ-UHFFFAOYSA-N 0.000 description 1
- HPJJZEKBWATTFL-UHFFFAOYSA-N 3-(6-fluoropyridin-3-yl)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=NC(F)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 HPJJZEKBWATTFL-UHFFFAOYSA-N 0.000 description 1
- MYIHJNHAJHTZDP-UHFFFAOYSA-N 3-(benzylamino)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1NCC1=CC=CC=C1 MYIHJNHAJHTZDP-UHFFFAOYSA-N 0.000 description 1
- FTJDERFAFFOHMW-UHFFFAOYSA-N 3-(dibenzylamino)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 FTJDERFAFFOHMW-UHFFFAOYSA-N 0.000 description 1
- RUOFXNWTIMLQKY-UHFFFAOYSA-N 3-(isoquinolin-1-ylamino)-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(NC=2C3=CC=CC=C3C=CN=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 RUOFXNWTIMLQKY-UHFFFAOYSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- SHRIIKXXOFKRRI-UHFFFAOYSA-N 3-[1-(1-benzylpiperidin-4-yl)benzimidazol-2-yl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2N(C3=CC=CC=C3N=2)C2CCN(CC=3C=CC=CC=3)CC2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 SHRIIKXXOFKRRI-UHFFFAOYSA-N 0.000 description 1
- CMGIGZFNCSGXAF-UHFFFAOYSA-N 3-[1-(benzenesulfonyl)indol-2-yl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2N(C3=CC=CC=C3C=2)S(=O)(=O)C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 CMGIGZFNCSGXAF-UHFFFAOYSA-N 0.000 description 1
- ZYMSIUQVGFOPSH-UHFFFAOYSA-N 3-[2-(dimethylamino)pyridin-3-yl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound CN(C)C1=NC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ZYMSIUQVGFOPSH-UHFFFAOYSA-N 0.000 description 1
- DGULFZFFRHWWQR-UHFFFAOYSA-N 3-[2-(hydroxymethyl)phenyl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound OCC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 DGULFZFFRHWWQR-UHFFFAOYSA-N 0.000 description 1
- QCCXXJZLTSVHRA-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]phenyl]-1-phenyl-5-pyridin-2-ylpyridin-2-one;dihydrochloride Chemical compound Cl.Cl.CN(C)CC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QCCXXJZLTSVHRA-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- OHHPKHDVPWTUHJ-UHFFFAOYSA-N 3-[3-[2-(dimethylamino)ethoxy]phenyl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound CN(C)CCOC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 OHHPKHDVPWTUHJ-UHFFFAOYSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- CTSSSJMFRDQJSY-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(N(C)C)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 CTSSSJMFRDQJSY-UHFFFAOYSA-N 0.000 description 1
- GQJKXFMJYNIQGQ-UHFFFAOYSA-N 3-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C1=CC(OCCN(C)C)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 GQJKXFMJYNIQGQ-UHFFFAOYSA-N 0.000 description 1
- QMEANMGCADMRFJ-UHFFFAOYSA-N 3-anilino-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1NC1=CC=CC=C1 QMEANMGCADMRFJ-UHFFFAOYSA-N 0.000 description 1
- OKQPBNYFLNFWST-UHFFFAOYSA-N 3-bromo-1-(3-hydroxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound OC1=CC=CC(N2C(C(Br)=CC(=C2)C=2N=CC=CC=2)=O)=C1 OKQPBNYFLNFWST-UHFFFAOYSA-N 0.000 description 1
- KVWUZXBTRWEPRO-UHFFFAOYSA-N 3-bromo-1-(3-methoxyphenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound COC1=CC=CC(N2C(C(Br)=CC(=C2)C=2N=CC=CC=2)=O)=C1 KVWUZXBTRWEPRO-UHFFFAOYSA-N 0.000 description 1
- VGRVFGIQMXZJOC-UHFFFAOYSA-N 3-bromo-1-cyclopentyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(Br)=CC(C=2N=CC=CC=2)=CN1C1CCCC1 VGRVFGIQMXZJOC-UHFFFAOYSA-N 0.000 description 1
- ZAJDJVMELGYWQC-UHFFFAOYSA-N 3-bromo-2-methoxy-5-pyridin-2-ylpyridine Chemical compound C1=C(Br)C(OC)=NC=C1C1=CC=CC=N1 ZAJDJVMELGYWQC-UHFFFAOYSA-N 0.000 description 1
- SHZMPEDWLZHZJT-UHFFFAOYSA-N 3-bromo-5-(1-methyl-3,6-dihydro-2h-pyridin-2-yl)-1-phenylpyridin-2-one Chemical compound CN1CC=CCC1C1=CN(C=2C=CC=CC=2)C(=O)C(Br)=C1 SHZMPEDWLZHZJT-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- YFYWQJJKOFDZLH-UHFFFAOYSA-N 3-carbazol-9-yl-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(N2C3=CC=CC=C3C3=CC=CC=C32)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 YFYWQJJKOFDZLH-UHFFFAOYSA-N 0.000 description 1
- QOKNUKKAUXFFDJ-UHFFFAOYSA-N 3-cyclohexyl-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C2CCCCC2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QOKNUKKAUXFFDJ-UHFFFAOYSA-N 0.000 description 1
- YBEJJYLAYJGAQA-UHFFFAOYSA-N 3-indazol-1-yl-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(N2C3=CC=CC=C3C=N2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 YBEJJYLAYJGAQA-UHFFFAOYSA-N 0.000 description 1
- XBBPVPSGSVJFIW-UHFFFAOYSA-N 3-indol-1-yl-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(N2C3=CC=CC=C3C=C2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 XBBPVPSGSVJFIW-UHFFFAOYSA-N 0.000 description 1
- USOPIZYLQLRAAQ-UHFFFAOYSA-N 3-iodo-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(I)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 USOPIZYLQLRAAQ-UHFFFAOYSA-N 0.000 description 1
- CPAHJXMTWDCYNT-UHFFFAOYSA-N 3-methoxy-2-(2-oxo-5-pyridin-2-yl-1-pyridin-3-ylpyridin-3-yl)benzonitrile Chemical compound COC1=CC=CC(C#N)=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 CPAHJXMTWDCYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000005925 3-methylpentyloxy group Chemical group 0.000 description 1
- HBZCASFJOHYEDE-UHFFFAOYSA-N 3-naphthalen-1-yl-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound O=C1C(C=2C3=CC=CC=C3C=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 HBZCASFJOHYEDE-UHFFFAOYSA-N 0.000 description 1
- ZDMDGXIGJLTRDB-UHFFFAOYSA-N 3-naphthalen-2-yl-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2C=C3C=CC=CC3=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 ZDMDGXIGJLTRDB-UHFFFAOYSA-N 0.000 description 1
- QLTCBLDEUINACH-UHFFFAOYSA-N 3-naphthalen-2-yl-5-pyridin-2-yl-1-pyridin-3-ylpyridin-2-one Chemical compound O=C1C(C=2C=C3C=CC=CC3=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 QLTCBLDEUINACH-UHFFFAOYSA-N 0.000 description 1
- BOAFCICMVMFLIT-UHFFFAOYSA-N 3-nitro-1h-pyridin-2-one Chemical compound OC1=NC=CC=C1[N+]([O-])=O BOAFCICMVMFLIT-UHFFFAOYSA-N 0.000 description 1
- BOJFHYYBZGOAPT-UHFFFAOYSA-N 3-phenoxy-1-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1OC1=CC=CC=C1 BOJFHYYBZGOAPT-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OUMJQKGSNLDFIF-UHFFFAOYSA-N 4-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 OUMJQKGSNLDFIF-UHFFFAOYSA-N 0.000 description 1
- OWXDDQDHCVYARP-UHFFFAOYSA-N 4-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzonitrile Chemical compound O=C1C(C=2C=CC(=CC=2)C#N)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 OWXDDQDHCVYARP-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- PSJGTXIYVQSTBT-UHFFFAOYSA-N 4-methyl-1,3-diphenyl-5-pyridin-2-ylpyridin-2-one Chemical compound O=C1C(C=2C=CC=CC=2)=C(C)C(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 PSJGTXIYVQSTBT-UHFFFAOYSA-N 0.000 description 1
- SUOPYDUVUDZULR-UHFFFAOYSA-N 5-(1,3-benzothiazol-2-yl)-3-(2-chlorophenyl)-1-phenylpyridin-2-one Chemical compound ClC1=CC=CC=C1C(C1=O)=CC(C=2SC3=CC=CC=C3N=2)=CN1C1=CC=CC=C1 SUOPYDUVUDZULR-UHFFFAOYSA-N 0.000 description 1
- RCISUIQHNCBFHQ-UHFFFAOYSA-N 5-(1,3-benzothiazol-2-yl)-3-[2-(1,3-benzothiazol-2-yl)phenyl]-1-phenylpyridin-2-one Chemical compound O=C1C(C=2C(=CC=CC=2)C=2SC3=CC=CC=C3N=2)=CC(C=2SC3=CC=CC=C3N=2)=CN1C1=CC=CC=C1 RCISUIQHNCBFHQ-UHFFFAOYSA-N 0.000 description 1
- WDNAUTHNUVVBCC-UHFFFAOYSA-N 5-(1,3-benzoxazol-2-yl)-3-(2-chlorophenyl)-1-phenylpyridin-2-one Chemical compound ClC1=CC=CC=C1C(C1=O)=CC(C=2OC3=CC=CC=C3N=2)=CN1C1=CC=CC=C1 WDNAUTHNUVVBCC-UHFFFAOYSA-N 0.000 description 1
- JHSCXFNLHZQJCO-UHFFFAOYSA-N 5-(1,3-benzoxazol-2-yl)-3-[2-(1,3-benzoxazol-2-yl)phenyl]-1-phenylpyridin-2-one Chemical compound O=C1C(C=2C(=CC=CC=2)C=2OC3=CC=CC=C3N=2)=CC(C=2OC3=CC=CC=C3N=2)=CN1C1=CC=CC=C1 JHSCXFNLHZQJCO-UHFFFAOYSA-N 0.000 description 1
- HHCRZAALJYIJHD-UHFFFAOYSA-N 5-(2-cyanophenyl)-6-oxo-n,1-diphenylpyridine-3-carboxamide Chemical compound C1=C(C=2C(=CC=CC=2)C#N)C(=O)N(C=2C=CC=CC=2)C=C1C(=O)NC1=CC=CC=C1 HHCRZAALJYIJHD-UHFFFAOYSA-N 0.000 description 1
- NACJWECKTQBPBW-UHFFFAOYSA-N 5-(5-chloro-1,3-benzoxazol-2-yl)-3-(2-chlorophenyl)-1-phenylpyridin-2-one Chemical compound N=1C2=CC(Cl)=CC=C2OC=1C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1Cl NACJWECKTQBPBW-UHFFFAOYSA-N 0.000 description 1
- PIRREEGWXLKXII-UHFFFAOYSA-N 5-(6-chloro-1h-benzimidazol-2-yl)-3-(2-chlorophenyl)-1-phenylpyridin-2-one Chemical compound N1C2=CC(Cl)=CC=C2N=C1C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1Cl PIRREEGWXLKXII-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- XADICJHFELMBGX-UHFFFAOYSA-N 5-bromo-2-methoxypyridine Chemical compound COC1=CC=C(Br)C=N1 XADICJHFELMBGX-UHFFFAOYSA-N 0.000 description 1
- AIDOPECDAOBJQE-UHFFFAOYSA-N 5-bromo-3-(2-chlorophenyl)-1-phenylpyridin-2-one Chemical compound ClC1=CC=CC=C1C(C1=O)=CC(Br)=CN1C1=CC=CC=C1 AIDOPECDAOBJQE-UHFFFAOYSA-N 0.000 description 1
- XKWSQIMYNVLGBO-UHFFFAOYSA-N 5-nitro-1h-pyridin-2-one Chemical compound OC1=CC=C([N+]([O-])=O)C=N1 XKWSQIMYNVLGBO-UHFFFAOYSA-N 0.000 description 1
- QLJIDZFJNALBLL-UHFFFAOYSA-N 5-pyridin-2-yl-1-pyridin-3-yl-3-[2-(trifluoromethyl)phenyl]pyridin-2-one Chemical compound FC(F)(F)C1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 QLJIDZFJNALBLL-UHFFFAOYSA-N 0.000 description 1
- LYZXLGOROGAPHD-UHFFFAOYSA-N 5-pyridin-2-yl-1-pyridin-3-yl-3-quinolin-8-ylpyridin-2-one Chemical compound O=C1C(C=2C3=NC=CC=C3C=CC=2)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 LYZXLGOROGAPHD-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- OFAKHNFLHDWLCG-UHFFFAOYSA-N 6-[5-(2-cyanophenyl)-6-oxo-1-phenylpyridin-3-yl]pyridine-2-carbonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=C(C=CC=2)C#N)=CN1C1=CC=CC=C1 OFAKHNFLHDWLCG-UHFFFAOYSA-N 0.000 description 1
- FCWKHHWHDOAOIF-UHFFFAOYSA-N 6-[5-(2-cyanophenyl)-6-oxo-1-phenylpyridin-3-yl]pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=N1 FCWKHHWHDOAOIF-UHFFFAOYSA-N 0.000 description 1
- BLHCMGRVFXRYRN-UHFFFAOYSA-N 6-hydroxynicotinic acid Chemical compound OC(=O)C1=CC=C(O)N=C1 BLHCMGRVFXRYRN-UHFFFAOYSA-N 0.000 description 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 1
- UNQYAAAWKOOBFQ-UHFFFAOYSA-N 7-[(4-chlorophenyl)methyl]-8-[4-chloro-3-(trifluoromethoxy)phenoxy]-1-(3-hydroxypropyl)-3-methylpurine-2,6-dione Chemical compound C=1C=C(Cl)C=CC=1CN1C=2C(=O)N(CCCO)C(=O)N(C)C=2N=C1OC1=CC=C(Cl)C(OC(F)(F)F)=C1 UNQYAAAWKOOBFQ-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- JISGOUWGGCZAIF-UHFFFAOYSA-N C(#N)C1=C(C=CC=C1)C=1C(N(C=C(C1)C1=NC=CC=C1)C1=CC(=CC=C1)C=O)=O.C(#N)C1=C(C=CC=C1)C=1C(N(C=C(C1)C1=NC=CC=C1)C1=CC(=CC=C1)CO)=O Chemical compound C(#N)C1=C(C=CC=C1)C=1C(N(C=C(C1)C1=NC=CC=C1)C1=CC(=CC=C1)C=O)=O.C(#N)C1=C(C=CC=C1)C=1C(N(C=C(C1)C1=NC=CC=C1)C1=CC(=CC=C1)CO)=O JISGOUWGGCZAIF-UHFFFAOYSA-N 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 206010012305 Demyelination Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- VLSMHEGGTFMBBZ-OOZYFLPDSA-M Kainate Chemical compound CC(=C)[C@H]1C[NH2+][C@H](C([O-])=O)[C@H]1CC([O-])=O VLSMHEGGTFMBBZ-OOZYFLPDSA-M 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000034800 Leukoencephalopathies Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 208000001089 Multiple system atrophy Diseases 0.000 description 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 102000004108 Neurotransmitter Receptors Human genes 0.000 description 1
- 108090000590 Neurotransmitter Receptors Proteins 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010036105 Polyneuropathy Diseases 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 208000026723 Urinary tract disease Diseases 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- PTWVHBHYYPLVCD-UHFFFAOYSA-M adamantan-1-ide;bromozinc(1+) Chemical compound Br[Zn+].C1C(C2)CC3CC1C[C-]2C3 PTWVHBHYYPLVCD-UHFFFAOYSA-M 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229940009868 aluminum magnesium silicate Drugs 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000049 anti-anxiety effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- GRDPYTMHGSXCAT-UHFFFAOYSA-N benzyl 4-[3-(3-bromo-2-oxo-5-pyridin-2-ylpyridin-1-yl)phenoxy]piperidine-1-carboxylate Chemical compound O=C1C(Br)=CC(C=2N=CC=CC=2)=CN1C(C=1)=CC=CC=1OC(CC1)CCN1C(=O)OCC1=CC=CC=C1 GRDPYTMHGSXCAT-UHFFFAOYSA-N 0.000 description 1
- JMRDBJLJZSUXPY-UHFFFAOYSA-N benzyl 4-[3-[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]phenoxy]piperidine-1-carboxylate Chemical compound C1CC(OC=2C=C(C=CC=2)N2C(C(C=3C(=CC=CC=3)C#N)=CC(=C2)C=2N=CC=CC=2)=O)CCN1C(=O)OCC1=CC=CC=C1 JMRDBJLJZSUXPY-UHFFFAOYSA-N 0.000 description 1
- JKIUUDJOCYHIGY-UHFFFAOYSA-N benzyl 4-hydroxypiperidine-1-carboxylate Chemical compound C1CC(O)CCN1C(=O)OCC1=CC=CC=C1 JKIUUDJOCYHIGY-UHFFFAOYSA-N 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229940013361 cresol Drugs 0.000 description 1
- 125000004144 cyclobuten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000323 cyclohepten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004145 cyclopenten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000003210 demyelinating effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- ZBQUMMFUJLOTQC-UHFFFAOYSA-N dichloronickel;3-diphenylphosphaniumylpropyl(diphenyl)phosphanium Chemical compound Cl[Ni]Cl.C=1C=CC=CC=1[PH+](C=1C=CC=CC=1)CCC[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 ZBQUMMFUJLOTQC-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 125000005216 haloheteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- IUJPWWXIGWZLRG-UHFFFAOYSA-N methyl 5-bromo-2-oxo-1-phenylpyridine-3-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(Br)=CN1C1=CC=CC=C1 IUJPWWXIGWZLRG-UHFFFAOYSA-N 0.000 description 1
- TXZVFXMZHYRSDN-UHFFFAOYSA-N methyl 5-bromo-2-oxo-1h-pyridine-3-carboxylate Chemical compound COC(=O)C1=CC(Br)=CNC1=O TXZVFXMZHYRSDN-UHFFFAOYSA-N 0.000 description 1
- KKMVACLRBBJYIJ-UHFFFAOYSA-N methyl 5-bromo-6-oxo-1h-pyridine-3-carboxylate Chemical compound COC(=O)C1=CNC(=O)C(Br)=C1 KKMVACLRBBJYIJ-UHFFFAOYSA-N 0.000 description 1
- MSNDPDPQLFUXOH-UHFFFAOYSA-N methyl 6-[5-(2-cyanophenyl)-6-oxo-1-phenylpyridin-3-yl]pyridine-2-carboxylate Chemical compound COC(=O)C1=CC=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=N1 MSNDPDPQLFUXOH-UHFFFAOYSA-N 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- QIXKHZXNMIBQIP-UHFFFAOYSA-N n-(1-adamantyl)-2-oxo-1-phenyl-5-pyridin-2-ylpyridine-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13NC(=O)C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QIXKHZXNMIBQIP-UHFFFAOYSA-N 0.000 description 1
- REOJNVZYRQKVQT-UHFFFAOYSA-N n-(1-adamantyl)-5-(2-cyanophenyl)-6-oxo-1-phenylpyridine-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13NC(=O)C(=CN(C1=O)C=2C=CC=CC=2)C=C1C1=CC=CC=C1C#N REOJNVZYRQKVQT-UHFFFAOYSA-N 0.000 description 1
- WLQDTBLFAACGES-UHFFFAOYSA-N n-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)-3-pyrrolidin-1-ylpropanamide Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1NC(=O)CCN1CCCC1 WLQDTBLFAACGES-UHFFFAOYSA-N 0.000 description 1
- SVDGWDPACQABEX-UHFFFAOYSA-N n-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 SVDGWDPACQABEX-UHFFFAOYSA-N 0.000 description 1
- YEFUBBOQNDRPKG-UHFFFAOYSA-N n-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzenesulfonamide Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1NS(=O)(=O)C1=CC=CC=C1 YEFUBBOQNDRPKG-UHFFFAOYSA-N 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- QQENOLFQZSIVBG-UHFFFAOYSA-N n-[2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 QQENOLFQZSIVBG-UHFFFAOYSA-N 0.000 description 1
- DNWJGCJQKSNWGU-UHFFFAOYSA-N n-[2-[5-(2-cyanophenyl)-6-oxo-1-phenylpyridin-3-yl]pyridin-3-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CN=C1C1=CN(C=2C=CC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 DNWJGCJQKSNWGU-UHFFFAOYSA-N 0.000 description 1
- WQVMTQJRQCFONZ-UHFFFAOYSA-N n-[3-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C(N(C=3C=CC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 WQVMTQJRQCFONZ-UHFFFAOYSA-N 0.000 description 1
- ODYAEZCJHINDGL-UHFFFAOYSA-N n-[3-(2-oxo-5-pyridin-2-yl-1-pyridin-3-ylpyridin-3-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C(N(C=3C=NC=CC=3)C=C(C=2)C=2N=CC=CC=2)=O)=C1 ODYAEZCJHINDGL-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- TURIGTCIZXTEEY-UHFFFAOYSA-N n-[4-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 TURIGTCIZXTEEY-UHFFFAOYSA-N 0.000 description 1
- MWDIHUJVDPGOQH-UHFFFAOYSA-N n-[6-[5-(2-cyanophenyl)-6-oxo-1-phenylpyridin-3-yl]pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=CC=CC(C2=CN(C(=O)C(C=3C(=CC=CC=3)C#N)=C2)C=2C=CC=CC=2)=N1 MWDIHUJVDPGOQH-UHFFFAOYSA-N 0.000 description 1
- VFBILHPIHUPBPZ-UHFFFAOYSA-N n-[[2-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]-1,3-oxazol-4-yl]methyl]-2-ethoxybenzamide Chemical compound CCOC1=CC=CC=C1C(=O)NCC1=COC(C=2C=C(OC(C)C)C(OC(F)F)=CC=2)=N1 VFBILHPIHUPBPZ-UHFFFAOYSA-N 0.000 description 1
- RMMOTIPPKFFKND-UHFFFAOYSA-N n-acetyl-n-[2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)phenyl]acetamide Chemical compound CC(=O)N(C(C)=O)C1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 RMMOTIPPKFFKND-UHFFFAOYSA-N 0.000 description 1
- XOPIBGVZJNKGAB-UHFFFAOYSA-N n-cyclohexyl-2-oxo-1-phenyl-5-pyridin-2-ylpyridine-3-carboxamide Chemical compound C=1C(C=2N=CC=CC=2)=CN(C=2C=CC=CC=2)C(=O)C=1C(=O)NC1CCCCC1 XOPIBGVZJNKGAB-UHFFFAOYSA-N 0.000 description 1
- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- VGBWXRBLDXADBF-UHFFFAOYSA-N n-methyl-2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzamide Chemical compound CNC(=O)C1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CC=C1 VGBWXRBLDXADBF-UHFFFAOYSA-N 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JVRQBXVGWOOFTE-UHFFFAOYSA-N n-tert-butyl-4-[5-(2-cyanophenyl)-6-oxo-1-pyridin-3-ylpyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)(C)C)=CC=C1C1=CN(C=2C=NC=CC=2)C(=O)C(C=2C(=CC=CC=2)C#N)=C1 JVRQBXVGWOOFTE-UHFFFAOYSA-N 0.000 description 1
- 229940037525 nasal preparations Drugs 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229940073665 octyldodecyl myristate Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 208000031237 olivopontocerebellar atrophy Diseases 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 230000007824 polyneuropathy Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical group C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- SSJUQXPDXBRSMB-UHFFFAOYSA-N tert-butyl 2-(2-oxo-5-pyridin-2-yl-1-pyridin-3-ylpyridin-3-yl)pyrrole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=CN1C1=CC=CN=C1 SSJUQXPDXBRSMB-UHFFFAOYSA-N 0.000 description 1
- UJHRNXLFCMDWRB-UHFFFAOYSA-N tert-butyl 4-[[3-(2-cyanophenyl)-2-oxo-5-pyridin-2-ylpyridin-1-yl]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CN1C(=O)C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=C1 UJHRNXLFCMDWRB-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 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
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P27/02—Ophthalmic agents
-
- 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
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Toxicology (AREA)
- Immunology (AREA)
- Addiction (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000175966 | 2000-06-12 | ||
GB0022483A GB0022483D0 (en) | 2000-09-13 | 2000-09-13 | 1 2 Dihydropyridine compounds manufacturing method thereof and use thereof |
PCT/JP2001/004857 WO2001096308A1 (fr) | 2000-06-12 | 2001-06-08 | Composes 1,2-dihydropyridine, leur procede de preparation et leur utilisation |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20025955D0 NO20025955D0 (no) | 2002-12-11 |
NO20025955L NO20025955L (no) | 2003-02-12 |
NO325160B1 true NO325160B1 (no) | 2008-02-11 |
Family
ID=26244997
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20025955A NO325160B1 (no) | 2000-06-12 | 2002-12-11 | 1,2-dihydropyridinforbindelser, fremgangsmate for fremstilling av de samme og anvendelse derav |
NO2012021C NO2012021I2 (no) | 2000-06-12 | 2012-12-18 | Perampanel eller salter eller hydrater derav |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO2012021C NO2012021I2 (no) | 2000-06-12 | 2012-12-18 | Perampanel eller salter eller hydrater derav |
Country Status (27)
Country | Link |
---|---|
US (3) | US6949571B2 (el) |
EP (3) | EP2177520A1 (el) |
JP (3) | JP3922368B2 (el) |
KR (3) | KR100850728B1 (el) |
CN (1) | CN1245386C (el) |
AT (1) | ATE420862T1 (el) |
AU (2) | AU2001262723C1 (el) |
BE (1) | BE2013C003I2 (el) |
BR (1) | BRPI0111596B8 (el) |
CA (1) | CA2412172C (el) |
CY (2) | CY1108969T1 (el) |
DE (1) | DE60137426D1 (el) |
DK (1) | DK1300396T3 (el) |
ES (1) | ES2320973T3 (el) |
FR (1) | FR12C0074I2 (el) |
HK (1) | HK1056871A1 (el) |
HU (2) | HU1300187D0 (el) |
IL (5) | IL152848A0 (el) |
LU (1) | LU92113I2 (el) |
MX (1) | MXPA02012314A (el) |
NL (1) | NL300565I2 (el) |
NO (2) | NO325160B1 (el) |
NZ (1) | NZ522773A (el) |
PT (1) | PT1300396E (el) |
TW (2) | TW200815402A (el) |
WO (1) | WO2001096308A1 (el) |
ZA (1) | ZA200209270B (el) |
Families Citing this family (140)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ522773A (en) | 2000-06-12 | 2005-06-24 | Eisai Co Ltd | 1,2-dihydropyridine compounds, manufacturing method thereof and use thereof |
JP2004536023A (ja) * | 2000-11-20 | 2004-12-02 | ブリストル−マイヤーズ スクイブ カンパニー | aP2インヒビターとしてのピリドン誘導体 |
US20030105144A1 (en) | 2001-04-17 | 2003-06-05 | Ping Gao | Stabilized oral pharmaceutical composition |
JP4119114B2 (ja) * | 2001-11-28 | 2008-07-16 | 広栄化学工業株式会社 | 新規なジヒドロキシ(3−ピリジル)ボラン類 |
GB0129260D0 (en) * | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
EP1465869B1 (en) * | 2001-12-21 | 2013-05-15 | Exelixis Patent Company LLC | Modulators of lxr |
US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
AU2003220401A1 (en) | 2002-03-18 | 2003-10-08 | Bristol-Myers Squibb Company | Uracil derivatives as inhibitors of tnf-alpha converting enzyme (tace) and matrix metalloproteinases |
ATE423094T1 (de) * | 2002-04-19 | 2009-03-15 | Glaxo Group Ltd | Verbindungen mit affinität zum 5ht2c-rezeptor und deren therapeutische verwendung |
JP4208512B2 (ja) | 2002-07-23 | 2009-01-14 | 株式会社クラレ | 5−(2’−ピリジル)−2−ピリドン誘導体の製造方法 |
AU2003274022A1 (en) * | 2002-10-17 | 2004-05-04 | Syngenta Participations Ag | 3-heterocyclylpyridine derivatives useful as herbicides |
US7683069B2 (en) * | 2002-12-16 | 2010-03-23 | Mitsubishi Tanabe Pharma Corporation | 3-substituted-4-pyrimidone derivatives |
US7189716B2 (en) * | 2003-01-03 | 2007-03-13 | Bristol-Myers Squibb Company | Tyrosine kinase inhibitors |
GB0305024D0 (en) * | 2003-03-05 | 2003-04-09 | Glaxo Group Ltd | Compounds |
SE0302324D0 (sv) * | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
SE0302323D0 (sv) * | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
SE0302486D0 (sv) | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
EP2522670A1 (en) | 2004-04-07 | 2012-11-14 | Takeda Pharmaceutical Company Limited | Heterocyclic CRF receptor antagonists |
JP2007099781A (ja) * | 2004-07-06 | 2007-04-19 | Eisai R & D Management Co Ltd | 1,2−ジヒドロピリジン化合物の結晶の製造方法 |
MY148809A (en) * | 2004-07-06 | 2013-05-31 | Eisai R&D Man Co Ltd | Crystals of 1,2-dihydropyridine compound and their production process |
GB0420722D0 (en) * | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
US20060069260A1 (en) * | 2004-09-28 | 2006-03-30 | Huiping Zhang | Preparation of N-aryl pyridones |
AU2005316540A1 (en) | 2004-12-16 | 2006-06-22 | Vertex Pharmaceuticals Incorporated | Pyrid-2-ones useful as inhibitors of Tec family protein kinases for the treatment of inflammatory, proliferative and immunologically-mediated diseases |
CA2603676A1 (en) * | 2005-01-07 | 2006-07-13 | Roskamp Research Llc | Compounds for inhibiting beta-amyloid production and methods of identifying the compounds |
TW200700392A (en) * | 2005-03-16 | 2007-01-01 | Astrazeneca Ab | Novel compounds |
PT1871368E (pt) * | 2005-04-04 | 2011-08-30 | Eisai R&D Man Co Ltd | COMPOSTOS DE DIHIDROPIRIDINA PARA DOENÇAS NEURODEGENERATIVAS E DEMjNCIA |
CA2603959A1 (en) * | 2005-04-08 | 2006-10-19 | Eisai R & D Management Co., Ltd. | Therapeutic agent for dyskinesia |
DK1928454T3 (da) | 2005-05-10 | 2014-11-03 | Intermune Inc | Pyridonderivater til modulering af stress-aktiveret proteinkinasesystem |
GB0510141D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
EP1919895A2 (en) * | 2005-08-02 | 2008-05-14 | Lexicon Pharmaceuticals, Inc. | 2-aminoaryl pyridines as protein kinases inhibitors |
EP1919905B1 (en) * | 2005-08-29 | 2011-02-23 | Vertex Pharmaceuticals Incorporated | 3,5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-recptor tyrosine kinases |
US7691885B2 (en) | 2005-08-29 | 2010-04-06 | Vertex Pharmaceuticals Incorporated | Pyridones useful as inhibitors of kinases |
US7786130B2 (en) | 2005-08-29 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Pyridones useful as inhibitors of kinases |
EP1932840B1 (en) * | 2005-10-03 | 2014-04-09 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic compound and pharmaceutical application thereof |
CA2634056C (en) * | 2005-12-21 | 2014-06-10 | Eisai R&D Management Co., Ltd. | Amorphous form of 1,2-dihydropyridine compound |
WO2007072868A1 (ja) * | 2005-12-21 | 2007-06-28 | Eisai R & D Management Co., Ltd. | 1,2-ジヒドロピリジン化合物の結晶(iv型) |
JP4865337B2 (ja) * | 2006-01-24 | 2012-02-01 | 富士フイルムファインケミカルズ株式会社 | 2,3’−ビピリジル−6’−オンの製造方法 |
AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
WO2007126060A1 (ja) * | 2006-04-28 | 2007-11-08 | Eisai R & D Management Co., Ltd | 1,2-ジヒドロピリジン化合物の塩 |
TW200808771A (en) | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds II |
TW200808763A (en) | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds I |
US20080108622A1 (en) * | 2006-10-19 | 2008-05-08 | Eisenach James C | Combination therapy for the treatment of pain |
US20080108603A1 (en) * | 2006-10-19 | 2008-05-08 | Eisenach James C | Combination therapy for the treatment of pain |
JP2010520154A (ja) * | 2007-03-05 | 2010-06-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 神経変性疾患のためのampaレセプターアンタゴニストおよびnmdaレセプターアンタゴニスト |
TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
US20100130537A1 (en) * | 2007-04-26 | 2010-05-27 | Eisai R&D Management Co., Ltd | Cinnamide compounds for dementia |
WO2009011412A2 (en) * | 2007-07-13 | 2009-01-22 | Eisai R & D Management Co., Ltd. | Combination of ampa receptor antagonists and acetylcholinesterase inhibitors for the treatment of neuropathic pain |
US20100222354A1 (en) * | 2007-07-13 | 2010-09-02 | Eisai R & D Management Co., Ltd. | AMPA Receptor Antagonists and Aldose Reductase Inhibitors for Neuropathic Pain |
EP2205565B1 (en) | 2007-09-14 | 2013-04-17 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1 h-pyridin-2-ones |
ATE516272T1 (de) | 2007-09-14 | 2011-07-15 | Ortho Mcneil Janssen Pharm | 1,3-disubstituierte 4-(aryl-x-phenyl)-1h-pyridin- 2-one |
JP5133416B2 (ja) | 2007-09-14 | 2013-01-30 | オルソー−マクニール−ジャンセン ファーマシューティカルズ, インコーポレイテッド. | 1’,3’−二置換−4−フェニル−3,4,5,6−テトラヒドロ−2h,1’h−[1,4’]ビピリジニル−2’−オン |
WO2009054544A1 (en) * | 2007-10-26 | 2009-04-30 | Eisai R & D Management Co., Ltd. | Ampa receptor antagonists for parkinson's disease and movement disorders |
CL2008003301A1 (es) | 2007-11-06 | 2009-10-16 | Astrazeneca Ab | Compuestos derivados de 3,4-dihidropirazina-2-carboxamida, inhibidores de la elastasa de neutrofilos humanos; composiciones farmacéuticas; procesos de preparación de compuestos y composición farmacéutica; y uso en el tratamiento de síndrome de dificultad respiratoria de los adultos, fibrosis quística, cáncer, entre otras. |
EP2220083B1 (en) | 2007-11-14 | 2017-07-19 | Janssen Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
CN101883757B (zh) | 2007-12-21 | 2013-06-12 | 株式会社可乐丽 | 6-卤代-3-芳基吡啶衍生物的制备方法 |
US20100297181A1 (en) * | 2007-12-26 | 2010-11-25 | Eisai R&D Management Co., Ltd. | AMPA Receptor Antagonists for Epilepsy, Mental Disorders or Deficits in Sensory Organ |
US20100256191A1 (en) * | 2007-12-26 | 2010-10-07 | Eisai R&D Management Co., Ltd. | Ampa receptor antagonists and zonisamide for epilepsy |
US20110118234A1 (en) * | 2008-05-05 | 2011-05-19 | Kaustav Biswas | Urea Compounds as Gamma Secretase Modulators |
JP5627574B2 (ja) | 2008-06-03 | 2014-11-19 | インターミューン, インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
US8859760B2 (en) | 2008-07-29 | 2014-10-14 | Frontier Scientific, Inc. | Compositions for killing or preventing the growth of microbes |
US8691849B2 (en) | 2008-09-02 | 2014-04-08 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
CA2738849C (en) | 2008-10-16 | 2016-06-28 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
US8598209B2 (en) * | 2008-10-31 | 2013-12-03 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
CN102232074B (zh) | 2008-11-28 | 2014-12-03 | 奥梅-杨森制药有限公司 | 作为代谢性谷氨酸盐受体调节剂的吲哚和苯并噁嗪衍生物 |
WO2010072607A1 (en) | 2008-12-23 | 2010-07-01 | F. Hoffmann-La Roche Ag | Dihydropyridone amides as p2x7 modulators |
WO2010072599A1 (en) | 2008-12-23 | 2010-07-01 | F. Hoffmann-La Roche Ag | Dihydropyridone ureas as p2x7 modulators |
JP5518895B2 (ja) | 2008-12-23 | 2014-06-11 | エフ.ホフマン−ラ ロシュ アーゲー | P2x7モジュレーターとしてのジヒドロピリドンアミド |
CN102264723B (zh) | 2008-12-23 | 2014-12-10 | 霍夫曼-拉罗奇有限公司 | 作为p2x7调节剂的二氢吡啶酮酰胺 |
US8153808B2 (en) | 2008-12-23 | 2012-04-10 | Roche Palo Alto Llc | Dihydropyridone amides as P2X7 modulators |
TW201036957A (en) | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
WO2010114896A1 (en) | 2009-03-31 | 2010-10-07 | Arqule, Inc. | Substituted indolo-pyridinone compounds |
MY161325A (en) | 2009-05-12 | 2017-04-14 | Janssen Pharmaceuticals Inc | 1, 2, 4-triazolo[4,3-a]pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
ES2409006T3 (es) | 2009-05-12 | 2013-06-24 | Janssen Pharmaceuticals Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de los receptores mGluR2 |
MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
WO2011039528A1 (en) | 2009-10-02 | 2011-04-07 | Astrazeneca Ab | 2-pyridone compounds used as inhibitors of neutrophil elastase |
JP2013234123A (ja) * | 2010-09-03 | 2013-11-21 | Taisho Pharmaceutical Co Ltd | 3−ピラゾリル−2−ピリドン誘導体 |
JP5852665B2 (ja) | 2010-11-08 | 2016-02-03 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | 1,2,4−トリアゾロ[4,3−a]ピリジン誘導体およびmGluR2受容体のポジティブアロステリックモジュレーターとしてのそれらの使用 |
ES2552455T3 (es) | 2010-11-08 | 2015-11-30 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
CA2815002C (en) | 2010-11-08 | 2019-10-22 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
JP5848775B2 (ja) * | 2010-12-06 | 2016-01-27 | コンフルエンス・ライフ・サイエンシズ,インコーポレーテッド | 置換ピリジノンピリジニル化合物 |
JP5922157B2 (ja) | 2011-03-04 | 2016-05-24 | エール ユニヴァーシティ | (−)−フペルジンaの工程及び関連組成物並びに治療法 |
ITMI20111952A1 (it) * | 2011-10-27 | 2013-04-28 | Italiana Sint Spa | Procedimento per la prepazione di 2-metossi-5-(piridin-2-il)piridina, un intermedio del perampanel |
WO2013102897A1 (en) | 2012-01-03 | 2013-07-11 | Mapi Pharma Ltd. | Polymorphs of perampanel |
WO2013148174A1 (en) * | 2012-03-31 | 2013-10-03 | University Of Georgia Research Foundation, Inc. | New anti-mycobacterial drugs against tuberculosis |
RU2701156C9 (ru) | 2012-07-18 | 2019-12-18 | Саншайн Лейк Фарма Ко., Лтд. | Азотсодержащие гетероциклические производные и их применение в фармацевтических препаратах |
ITMI20121390A1 (it) | 2012-08-06 | 2014-02-07 | F I S Fabbrica Italiana Sint P A | Procedimento per la preparazione di acido 2-cianofenilboronico e suoi esteri, intermedi del perampanel o di e2040 |
AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
JO3225B1 (ar) * | 2012-11-27 | 2018-03-08 | Lilly Co Eli | 6-((s)-1-{1-[5-(2-هيدروكسي-إيثوكسي)-بيريدين-2-يل]-1h-بيرازول-3-يل}إيثيل)-3h-1 ، 3-بنزو ثيازول-2- أون باعتباره مضاد مستقبل ampa يعتمد على tarp- جاما 8 |
TW201441193A (zh) | 2012-12-06 | 2014-11-01 | Kyowa Hakko Kirin Co Ltd | 吡啶酮化合物 |
US9242969B2 (en) | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
WO2014163210A1 (en) | 2013-04-04 | 2014-10-09 | Eisai R&D Management Co., Ltd. | [11 c] and [18f] labeled 1,3-diphenyl-5-(pyrimidin-2-yl)-pyridin-2(1 h)-one derivatives and their use for pet imaging of the ampa receptor |
JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
CN103274993A (zh) * | 2013-06-13 | 2013-09-04 | 南京工业大学 | 二氢吡啶和吡咯类杂环的新合成方法 |
EA031384B1 (ru) * | 2013-07-25 | 2018-12-28 | Тева Фармасьютикалз Интернэшнл Гмбх | Улучшенные способы получения перампанеля |
JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
EP3063139B1 (en) | 2013-10-29 | 2018-11-21 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
CN103664756A (zh) * | 2013-11-26 | 2014-03-26 | 苏州晶云药物科技有限公司 | 吡仑帕奈新晶型a及其制备方法 |
CN104706604A (zh) * | 2013-12-12 | 2015-06-17 | 北京星昊医药股份有限公司 | 一种吡仑帕奈冻干口崩片及其制备方法 |
CN104725301A (zh) * | 2013-12-20 | 2015-06-24 | 北京蓝贝望生物医药科技股份有限公司 | 一种1,2-二氢吡啶-2-酮衍生物的制备方法 |
BR112016016390B1 (pt) | 2014-01-21 | 2023-04-11 | Janssen Pharmaceutica Nv | Produto compreendendo modulador alostérico positivo do receptor glutamatérgico metabotrópico do subtipo 2 e ligante da proteína de vesícula sináptica 2a |
ES2860298T3 (es) | 2014-01-21 | 2021-10-04 | Janssen Pharmaceutica Nv | Combinaciones que comprenden moduladores alostéricos positivos del receptor glutamatérgico metabotrópico de subtipo 2 y su uso |
RU2692485C2 (ru) | 2014-04-02 | 2019-06-25 | Интермьюн, Инк. | Противофиброзные пиридиноны |
CN105085382B (zh) * | 2014-05-14 | 2019-10-18 | 江苏豪森药业集团有限公司 | 吡仑帕奈异构体晶型及其制备方法和用途 |
TW201609719A (zh) | 2014-05-28 | 2016-03-16 | 美國禮來大藥廠 | 作為TARP-γ8依賴性AMPA受體拮抗劑之6-經取代-3H-1,3-苯并噻唑-2-酮化合物 |
CN103980188B (zh) * | 2014-05-30 | 2016-01-27 | 浙江永宁药业股份有限公司 | 一种吡仑帕奈的合成方法及其中间体和中间体的合成方法 |
UY36294A (es) | 2014-09-12 | 2016-04-29 | Novartis Ag | Compuestos y composiciones como inhibidores de quinasa |
KR101783642B1 (ko) | 2015-02-04 | 2017-10-10 | 비욘드바이오주식회사 | 헤테로 고리 화합물 및 그를 포함하는 약제학적 조성물 |
US10111867B2 (en) | 2015-02-17 | 2018-10-30 | Mapi Pharma Ltd. | Process and intermediates for the preparation of perampanel |
AR104259A1 (es) * | 2015-04-15 | 2017-07-05 | Celgene Quanticel Res Inc | Inhibidores de bromodominio |
WO2016172333A1 (en) | 2015-04-21 | 2016-10-27 | Teva Pharmaceuticals International Gmbh | A solid state form of perampanel |
DK3321252T3 (da) | 2015-07-06 | 2020-11-16 | Public Univ Corp Yokohama City Univ | Ny forbindelse der specifikt binder til ampa-receptor |
CN105085383B (zh) * | 2015-08-19 | 2017-09-01 | 四川大学 | 5‑甲基‑2(1h)吡啶酮衍生物及其制备方法和用途 |
RU2743998C2 (ru) * | 2015-11-13 | 2021-03-01 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Пиранодипиридиновое соединение |
KR101652750B1 (ko) * | 2015-12-03 | 2016-08-31 | 김종선 | 피리딘 및 그 유도체의 정제방법 |
EP3515446B1 (en) | 2016-09-19 | 2023-12-20 | Novartis AG | Therapeutic combinations comprising a raf inhibitor and a erk inhibitor |
MA46589A (fr) | 2016-10-24 | 2019-08-28 | Yumanity Therapeutics Inc | Composés et utilisations de ces derniers |
WO2018094128A1 (en) * | 2016-11-18 | 2018-05-24 | Vps-3, Inc. | 4-((6-bromopyridin-3-yl)oxy)benzonitrile and processes of preparation |
CN109996569B (zh) * | 2016-12-22 | 2022-05-03 | 百多力股份公司 | 用于医疗装置的药物释放涂层及其制备方法 |
JP6241974B1 (ja) | 2017-01-11 | 2017-12-06 | 公立大学法人横浜市立大学 | 霊長類生体の脳内ampa受容体のイメージング方法、プログラム、及びスクリーニング方法 |
GB201702221D0 (en) | 2017-02-10 | 2017-03-29 | Univ Of Sussex | Compounds |
ES2952265T3 (es) | 2017-05-02 | 2023-10-30 | Novartis Ag | Terapia combinada que comprende un inhibidor de Raf y trametinib |
WO2019028062A1 (en) * | 2017-07-31 | 2019-02-07 | Washington University | PIRFENIDONE DERIVATIVES FOR MODULATION OF B-LYMPHOCYTE ACTIVITY AND PROTECTION OF ORGANS |
US11873298B2 (en) | 2017-10-24 | 2024-01-16 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
CN110028442B (zh) * | 2018-01-11 | 2020-07-17 | 新发药业有限公司 | 一种吡仑帕奈的简便制备方法 |
GB201803340D0 (en) * | 2018-03-01 | 2018-04-18 | Univ Of Sussex | Compounds |
EP3560934A1 (en) | 2018-04-26 | 2019-10-30 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Process for the preparation of pure 2-cyanophenylboronic acid and esters thereof, intermediates of perampanel or of e2040 |
CN113226286B (zh) | 2018-12-14 | 2024-08-20 | 卫材R&D管理有限公司 | 1,2-二氢吡啶化合物的水基药物制剂 |
EP3914593A4 (en) | 2019-01-24 | 2022-11-02 | Yumanity Therapeutics, Inc. | COMPOUNDS AND THEIR USES |
CN110483563B (zh) * | 2019-09-06 | 2021-12-28 | 山西医科大学 | 一种新型离子型β-萘酚醛席夫碱锆配合物的制备方法及应用 |
KR102392825B1 (ko) | 2020-02-18 | 2022-04-29 | 명인제약주식회사 | 2-(2-옥소-1-페닐-5-피리딘-2-일피리딘-3-일)벤조니트릴과 l-말릭산의 공결정 화합물 및 이의 제조 방법 |
CN111362930B (zh) * | 2020-04-15 | 2023-02-03 | 安徽医科大学 | 一种1,2,4-噁二唑-吡啶类化合物及其应用 |
EP4403184A1 (en) | 2021-09-15 | 2024-07-24 | University of The Ryukyus | Pharmaceutical composition for use in treating cognitive decline, excess weight, or obesity |
WO2023042888A1 (ja) | 2021-09-15 | 2023-03-23 | 国立大学法人 琉球大学 | 認知機能低下、または過体重もしくは肥満症を処置することに用いるための医薬組成物 |
CN116265440B (zh) * | 2021-12-16 | 2024-09-27 | 贵州大学 | 一种水杨酮拼接吡啶酮类化合物及其制备方法及应用 |
CN114057630B (zh) * | 2021-12-23 | 2023-06-02 | 郑州大学 | 吡非尼酮衍生物及其合成方法和应用 |
US11878958B2 (en) | 2022-05-25 | 2024-01-23 | Ikena Oncology, Inc. | MEK inhibitors and uses thereof |
WO2024010585A1 (en) * | 2022-07-07 | 2024-01-11 | Yale University | Non-covalent inhibitors of the main protease of sars-cov-2 and methods of use |
KR20240008565A (ko) * | 2022-07-12 | 2024-01-19 | 이화여자대학교 산학협력단 | 연속 흐름 공정을 포함하는 페람파넬 유도체의 제조 방법 |
US11958832B1 (en) | 2023-10-12 | 2024-04-16 | King Faisal University | 2-alkoxy[4,3:6,3-terpyridine]-3-carbonitriles as antimicrobial compounds |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5283761A (en) * | 1976-01-01 | 1977-07-12 | Yamanouchi Pharmaceut Co Ltd | Novel pyridone derivative |
JPS5531072A (en) * | 1979-07-30 | 1980-03-05 | Rikagaku Kenkyusho | Preparation of 2-pyridone compound |
DE4003541C1 (el) | 1990-02-06 | 1991-08-08 | Alter S.A., Madrid, Es | |
US5356902A (en) | 1992-11-06 | 1994-10-18 | Eli Lilly And Company | Decahydroisoquinoline compounds as excitatory amino acid receptor antagonists |
IL109397A0 (en) | 1993-04-28 | 1994-07-31 | Schering Ag | Quinoxalinedione derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
HU219777B (hu) | 1993-07-02 | 2001-07-30 | Gyógyszerkutató Intézet Kft. | Optikailag aktív 1-(4-nitro-fenil)-4-metil-7,8-metiléndioxi-3,4-dihidro-5H-2,3-benzodiazepin és eljárás előállítására |
EP0784054B1 (en) | 1994-09-27 | 2001-11-28 | Yamanouchi Pharmaceutical Co. Ltd. | 1,2,3,4-tetrahydroquinoxalinedione derivatives and use as glutamate receptor antagonists |
CN1188401C (zh) * | 1995-04-27 | 2005-02-09 | 三菱制药株式会社 | 杂环类酰胺化合物及其医药用途 |
US5935551A (en) | 1995-11-15 | 1999-08-10 | California Institute Of Technology | Synthesis of zeolites by hydrothermal reaction of zeolite P1 |
DE19604920A1 (de) | 1996-02-01 | 1997-08-07 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
US5891871A (en) | 1996-03-21 | 1999-04-06 | Cocensys, Inc. | Substituted 2,3-benzodiazepin-4-ones and the use thereof |
HU9600871D0 (en) | 1996-04-04 | 1996-05-28 | Gyogyszerkutato Intezet | New 2,3-benzodiazepine derivatives |
CN1103772C (zh) | 1996-05-15 | 2003-03-26 | 辉瑞大药厂 | 新的2,3-二取代-4(3h)-喹唑啉酮类化合物 |
DE19643037A1 (de) | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
WO1998024780A2 (en) | 1996-12-05 | 1998-06-11 | Amgen Inc. | Substituted pyrimidinone and pyridinone compounds and their use |
ES2219866T3 (es) | 1997-02-28 | 2004-12-01 | Pfizer Products Inc. | Atropisomeros de 3-aril-4(3h)-quinazolinonas y su uso como antagonistas del receptor de ampa. |
GB9708945D0 (en) * | 1997-05-01 | 1997-06-25 | Merck Sharp & Dohme | Therapeutic agents |
GB9711753D0 (en) | 1997-06-06 | 1997-08-06 | Merck Sharp & Dohme | Therapeutic agents |
AU1504599A (en) * | 1997-12-17 | 1999-07-05 | Shionogi & Co., Ltd. | Novel pyridine compounds |
EP1100504A2 (en) | 1998-07-02 | 2001-05-23 | Eisai Co., Ltd. | Pharmaceutical compositions and their uses for treatment of demyelinating disorders |
DE19835918A1 (de) | 1998-08-07 | 2000-02-10 | Dresden Arzneimittel | Neue antikonvulsiv wirkende 4-Amino-1-aryl-pyridin-2-one und Verfahren zu deren Herstellung |
NZ522773A (en) | 2000-06-12 | 2005-06-24 | Eisai Co Ltd | 1,2-dihydropyridine compounds, manufacturing method thereof and use thereof |
GB0129260D0 (en) | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
-
2001
- 2001-06-08 NZ NZ522773A patent/NZ522773A/en not_active IP Right Cessation
- 2001-06-08 BR BRPI0111596A patent/BRPI0111596B8/pt not_active IP Right Cessation
- 2001-06-08 JP JP2002510451A patent/JP3922368B2/ja not_active Expired - Lifetime
- 2001-06-08 IL IL15284801A patent/IL152848A0/xx active IP Right Grant
- 2001-06-08 KR KR1020027016890A patent/KR100850728B1/ko active Protection Beyond IP Right Term
- 2001-06-08 KR KR1020077020875A patent/KR100904011B1/ko active IP Right Grant
- 2001-06-08 AU AU2001262723A patent/AU2001262723C1/en active Active
- 2001-06-08 AU AU6272301A patent/AU6272301A/xx active Pending
- 2001-06-08 DK DK01936920T patent/DK1300396T3/da active
- 2001-06-08 AT AT01936920T patent/ATE420862T1/de active
- 2001-06-08 HU HUP1300187 patent/HU1300187D0/hu unknown
- 2001-06-08 EP EP09015363A patent/EP2177520A1/en not_active Withdrawn
- 2001-06-08 MX MXPA02012314A patent/MXPA02012314A/es active IP Right Grant
- 2001-06-08 PT PT01936920T patent/PT1300396E/pt unknown
- 2001-06-08 ES ES01936920T patent/ES2320973T3/es not_active Expired - Lifetime
- 2001-06-08 KR KR1020077020877A patent/KR100869271B1/ko active IP Right Grant
- 2001-06-08 CA CA2412172A patent/CA2412172C/en not_active Expired - Lifetime
- 2001-06-08 CN CNB018110525A patent/CN1245386C/zh not_active Expired - Lifetime
- 2001-06-08 US US10/296,719 patent/US6949571B2/en active Active
- 2001-06-08 DE DE60137426T patent/DE60137426D1/de not_active Expired - Lifetime
- 2001-06-08 EP EP09000287A patent/EP2053041A3/en not_active Withdrawn
- 2001-06-08 EP EP01936920A patent/EP1300396B1/en not_active Expired - Lifetime
- 2001-06-08 WO PCT/JP2001/004857 patent/WO2001096308A1/ja active Application Filing
- 2001-06-08 HU HU0303398A patent/HU229553B1/hu active Protection Beyond IP Right Term
- 2001-06-12 TW TW096134645A patent/TW200815402A/zh not_active IP Right Cessation
- 2001-06-12 TW TW090114146A patent/TWI292757B/zh active
-
2002
- 2002-11-14 ZA ZA2002/09270A patent/ZA200209270B/en unknown
- 2002-11-14 IL IL152848A patent/IL152848A/en active Protection Beyond IP Right Term
- 2002-12-11 NO NO20025955A patent/NO325160B1/no not_active IP Right Cessation
-
2003
- 2003-09-29 HK HK03107029.7A patent/HK1056871A1/xx not_active IP Right Cessation
-
2005
- 2005-07-06 US US11/174,514 patent/US7563811B2/en not_active Expired - Lifetime
-
2006
- 2006-12-13 JP JP2006335187A patent/JP5068069B2/ja not_active Expired - Fee Related
-
2007
- 2007-07-18 IL IL184686A patent/IL184686A/en active IP Right Grant
- 2007-07-18 IL IL184687A patent/IL184687A/en active IP Right Grant
-
2008
- 2008-07-03 IL IL192605A patent/IL192605A/en active IP Right Grant
-
2009
- 2009-02-27 US US12/395,378 patent/US7939549B2/en not_active Expired - Lifetime
- 2009-04-10 CY CY20091100419T patent/CY1108969T1/el unknown
-
2012
- 2012-05-21 JP JP2012115592A patent/JP2012207021A/ja not_active Withdrawn
- 2012-12-10 FR FR12C0074C patent/FR12C0074I2/fr active Active
- 2012-12-12 LU LU92113C patent/LU92113I2/fr unknown
- 2012-12-18 CY CY2012032C patent/CY2012032I2/el unknown
- 2012-12-18 NO NO2012021C patent/NO2012021I2/no unknown
- 2012-12-21 NL NL300565C patent/NL300565I2/nl unknown
-
2013
- 2013-01-03 BE BE2013C003C patent/BE2013C003I2/fr unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO325160B1 (no) | 1,2-dihydropyridinforbindelser, fremgangsmate for fremstilling av de samme og anvendelse derav | |
RU2358733C2 (ru) | Фармацевтические композиции и их применения | |
EP1319659A1 (en) | Pyridazinones and triazinones and medicinal use thereof | |
RU2265015C2 (ru) | Соединения 1,2-дигидропиридина, способ их получения и их использование |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
SPCF | Filing of supplementary protection certificate |
Free format text: PRODUCT NAME: FYCOMPA; REG. NO/DATE: EU/1/12/776/001-016+ 20120827 Spc suppl protection certif: 2012021 Filing date: 20121218 |
|
SPCG | Granted supplementary protection certificate |
Free format text: PRODUCT NAME: FYCOMPA; REG. NO/DATE: EU/1/12/776/001-016+ 20120827 Spc suppl protection certif: 2012021 Filing date: 20121218 Extension date: 20260608 |
|
MK1K | Patent expired |