CA2562130C - 2-propene-1-ones as hsp 70 inducers - Google Patents
2-propene-1-ones as hsp 70 inducers Download PDFInfo
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- CA2562130C CA2562130C CA2562130A CA2562130A CA2562130C CA 2562130 C CA2562130 C CA 2562130C CA 2562130 A CA2562130 A CA 2562130A CA 2562130 A CA2562130 A CA 2562130A CA 2562130 C CA2562130 C CA 2562130C
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- CA
- Canada
- Prior art keywords
- compound
- phenyl
- 8alkyl
- acryloyl
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000000411 inducer Substances 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 936
- 239000000203 mixture Substances 0.000 claims abstract description 79
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 55
- 201000010099 disease Diseases 0.000 claims abstract description 48
- 230000035882 stress Effects 0.000 claims abstract description 37
- 230000001575 pathological effect Effects 0.000 claims abstract description 35
- 238000011282 treatment Methods 0.000 claims abstract description 32
- 230000006378 damage Effects 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 206010040047 Sepsis Diseases 0.000 claims abstract description 14
- 210000004556 brain Anatomy 0.000 claims abstract description 14
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 14
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 13
- 208000009304 Acute Kidney Injury Diseases 0.000 claims abstract description 11
- 208000033626 Renal failure acute Diseases 0.000 claims abstract description 11
- 208000006011 Stroke Diseases 0.000 claims abstract description 11
- 201000011040 acute kidney failure Diseases 0.000 claims abstract description 11
- 208000012998 acute renal failure Diseases 0.000 claims abstract description 11
- 230000002496 gastric effect Effects 0.000 claims abstract description 11
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 10
- 206010019851 Hepatotoxicity Diseases 0.000 claims abstract description 9
- 230000032683 aging Effects 0.000 claims abstract description 9
- 231100000304 hepatotoxicity Toxicity 0.000 claims abstract description 9
- 230000007686 hepatotoxicity Effects 0.000 claims abstract description 9
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- 230000003961 neuronal insult Effects 0.000 claims abstract description 9
- 230000003612 virological effect Effects 0.000 claims abstract description 9
- 206010048554 Endothelial dysfunction Diseases 0.000 claims abstract description 8
- 208000032843 Hemorrhage Diseases 0.000 claims abstract description 8
- 230000008694 endothelial dysfunction Effects 0.000 claims abstract description 8
- 239000012453 solvate Substances 0.000 claims abstract description 8
- 208000002249 Diabetes Complications Diseases 0.000 claims abstract description 7
- 206010012655 Diabetic complications Diseases 0.000 claims abstract description 7
- 230000007850 degeneration Effects 0.000 claims abstract description 7
- 201000002862 Angle-Closure Glaucoma Diseases 0.000 claims abstract description 4
- -1 nitro, amino Chemical group 0.000 claims description 160
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 102
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 102
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 239000000243 solution Substances 0.000 claims description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 40
- 125000002950 monocyclic group Chemical group 0.000 claims description 36
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 239000004202 carbamide Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
- 238000006467 substitution reaction Methods 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 229910006069 SO3H Inorganic materials 0.000 claims description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000004928 piperidonyl group Chemical group 0.000 claims description 10
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 10
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 9
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 8
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 8
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 8
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000001420 pyrrolonyl group Chemical group 0.000 claims description 7
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 125000003725 azepanyl group Chemical group 0.000 claims description 6
- 125000002785 azepinyl group Chemical group 0.000 claims description 6
- 125000004069 aziridinyl group Chemical group 0.000 claims description 6
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 6
- 125000005959 diazepanyl group Chemical group 0.000 claims description 6
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims description 6
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 6
- PCKXWVZXQXYHED-UHFFFAOYSA-N 1-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]-3-(2-pyridin-2-ylsulfanylethyl)urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)NCCSC1=CC=CC=N1 PCKXWVZXQXYHED-UHFFFAOYSA-N 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- RKZPUSDZMKGGEN-UHFFFAOYSA-N 1-(4-nitrophenyl)-4-[4-(3-quinolin-2-ylprop-2-enoyl)benzoyl]piperazin-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)CN(C(=O)C=2C=CC(=CC=2)C(=O)C=CC=2N=C3C=CC=CC3=CC=2)CC1 RKZPUSDZMKGGEN-UHFFFAOYSA-N 0.000 claims description 4
- HGRHSFHZGZXLHG-UHFFFAOYSA-N 1-[2-[amino-(6-methylpyridin-2-yl)amino]ethyl]-3-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]urea Chemical compound CC1=CC=CC(N(N)CCNC(=O)NC=2C=CC(=CC=2)C(=O)C=CC=2N=C3C=CC=CC3=NC=2)=N1 HGRHSFHZGZXLHG-UHFFFAOYSA-N 0.000 claims description 4
- TWHUCNBLQNZESF-UHFFFAOYSA-N 1-morpholin-4-ylsulfonyl-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NS(=O)(=O)N1CCOCC1 TWHUCNBLQNZESF-UHFFFAOYSA-N 0.000 claims description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- YCBMTZJHHRLPFY-UHFFFAOYSA-N propan-2-yl 1-[4-(3-quinolin-2-ylprop-2-enoyl)benzoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC(C)C)CCN1C(=O)C1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=C1 YCBMTZJHHRLPFY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- QKQZVTFKTDFYRV-UHFFFAOYSA-N thiophen-2-ylmethyl n-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C=1C=CSC=1COC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=C1C=CC=CC1=1)=CC=1N1CCOCC1 QKQZVTFKTDFYRV-UHFFFAOYSA-N 0.000 claims description 4
- 229930192474 thiophene Chemical group 0.000 claims description 4
- 230000029663 wound healing Effects 0.000 claims description 4
- VOHKUKJMBMEPFX-UHFFFAOYSA-N (1-methylimidazol-4-yl)methyl n-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]carbamate Chemical compound CN1C=NC(COC(=O)NC=2C=CC(=CC=2)C(=O)C=CC=2N=C3C=CC=CC3=CC=2)=C1 VOHKUKJMBMEPFX-UHFFFAOYSA-N 0.000 claims description 3
- LTAMXOWGQGJLPS-UHFFFAOYSA-N (4-fluorophenyl)methyl n-[4-[3-(6-pyrrolidin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(F)=CC=C1COC(=O)NC1=CC=C(C(=O)C=CC=2N=C(C=CC=2)N2CCCC2)C=C1 LTAMXOWGQGJLPS-UHFFFAOYSA-N 0.000 claims description 3
- HYZJGQRDVJLWPK-UHFFFAOYSA-N 1-(2-morpholin-4-yl-2-oxoethyl)-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NCC(=O)N1CCOCC1 HYZJGQRDVJLWPK-UHFFFAOYSA-N 0.000 claims description 3
- KSLYIYKTZYNAEA-UHFFFAOYSA-N 1-(2-morpholin-4-yl-2-oxoethyl)-3-[4-[3-(6-piperazin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCNCC2)C=CC=1NC(=O)NCC(=O)N1CCOCC1 KSLYIYKTZYNAEA-UHFFFAOYSA-N 0.000 claims description 3
- QLWUDCVSDMOHDO-UHFFFAOYSA-N 1-(2-morpholin-4-ylethyl)-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NCCN1CCOCC1 QLWUDCVSDMOHDO-UHFFFAOYSA-N 0.000 claims description 3
- YTNBZJNEISPYDZ-UHFFFAOYSA-N 1-(2-morpholin-4-ylethyl)-3-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)NCCN1CCOCC1 YTNBZJNEISPYDZ-UHFFFAOYSA-N 0.000 claims description 3
- SQTSPANZQDCPLB-UHFFFAOYSA-N 1-(2-morpholin-4-ylethyl)-3-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)NCCN1CCOCC1 SQTSPANZQDCPLB-UHFFFAOYSA-N 0.000 claims description 3
- SIHKNIZZPDIPIR-UHFFFAOYSA-N 1-(2-morpholin-4-ylethyl)-3-[4-[3-[6-(2-piperidin-1-ylethylamino)pyridin-2-yl]prop-2-enoyl]phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(NCCN3CCCCC3)C=CC=2)C=CC=1NC(=O)NCCN1CCOCC1 SIHKNIZZPDIPIR-UHFFFAOYSA-N 0.000 claims description 3
- YAGXYDLVMXHLLL-UHFFFAOYSA-N 1-(2-piperidin-4-yloxyethyl)-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NCCOC1CCNCC1 YAGXYDLVMXHLLL-UHFFFAOYSA-N 0.000 claims description 3
- JFLDHEWJFKLKAC-UHFFFAOYSA-N 1-(2-pyridin-2-ylsulfanylethyl)-3-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)NCCSC1=CC=CC=N1 JFLDHEWJFKLKAC-UHFFFAOYSA-N 0.000 claims description 3
- YKETYCCBRFJDGY-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C1CN(C)CCN1C(=O)CNC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=C1 YKETYCCBRFJDGY-UHFFFAOYSA-N 0.000 claims description 3
- CLASNUPMGFZDQW-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)ethyl]-3-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]urea Chemical compound C1CN(C)CCN1CCNC(=O)NC1=CC=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=C1 CLASNUPMGFZDQW-UHFFFAOYSA-N 0.000 claims description 3
- WMEMYUIZSGWVCQ-UHFFFAOYSA-N 1-[2-[2-(benzenesulfonyl)hydrazinyl]ethyl]-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NCCNNS(=O)(=O)C1=CC=CC=C1 WMEMYUIZSGWVCQ-UHFFFAOYSA-N 0.000 claims description 3
- WAYFVGWPNPTWTM-UHFFFAOYSA-N 1-[2-[amino-(1-methylpiperidin-4-yl)amino]ethyl]-3-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C1CN(C)CCC1N(N)CCNC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=C1 WAYFVGWPNPTWTM-UHFFFAOYSA-N 0.000 claims description 3
- OZMGSIBDRGEJSD-UHFFFAOYSA-N 1-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]-3-(2-pyridin-2-ylsulfonylethyl)urea Chemical compound C=1C=C(C(=O)C=CC=2N=CC=CC=2)C=CC=1NC(=O)NCCS(=O)(=O)C1=CC=CC=N1 OZMGSIBDRGEJSD-UHFFFAOYSA-N 0.000 claims description 3
- HVNRQGWHOKCUIG-UHFFFAOYSA-N 1-[4-(3-quinolin-2-ylprop-2-enoyl)benzoyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)C1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=C1 HVNRQGWHOKCUIG-UHFFFAOYSA-N 0.000 claims description 3
- GZTMVYRHBRTCOZ-UHFFFAOYSA-N 1-[4-(4-hydroxyiminopiperidine-1-carbonyl)phenyl]-3-quinoxalin-2-ylprop-2-en-1-one Chemical compound C1CC(=NO)CCN1C(=O)C1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=C1 GZTMVYRHBRTCOZ-UHFFFAOYSA-N 0.000 claims description 3
- WMVYHDZRMRQHBL-UHFFFAOYSA-N 1-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]-3-(2-oxo-2-piperazin-1-ylethyl)urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)NCC(=O)N1CCNCC1 WMVYHDZRMRQHBL-UHFFFAOYSA-N 0.000 claims description 3
- UVXHGCSAFKMTOF-UHFFFAOYSA-N 1-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]-3-(2-oxo-2-piperidin-1-ylethyl)urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)NCC(=O)N1CCCCC1 UVXHGCSAFKMTOF-UHFFFAOYSA-N 0.000 claims description 3
- XYJDHCQTDXSZQN-UHFFFAOYSA-N 1-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]-3-(2-piperidin-4-ylsulfanylethyl)urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)NCCSC1CCNCC1 XYJDHCQTDXSZQN-UHFFFAOYSA-N 0.000 claims description 3
- VHHHGCAWYALZKL-UHFFFAOYSA-N 1-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]-3-(2-pyridin-2-ylsulfonylethyl)urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)NCCS(=O)(=O)C1=CC=CC=N1 VHHHGCAWYALZKL-UHFFFAOYSA-N 0.000 claims description 3
- PLVFHIUQWNXRAU-UHFFFAOYSA-N 1-[4-[3-(6-piperazin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]-3-(2-piperidin-1-ylethyl)urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCNCC2)C=CC=1NC(=O)NCCN1CCCCC1 PLVFHIUQWNXRAU-UHFFFAOYSA-N 0.000 claims description 3
- JVXCLFRKMLYVPN-UHFFFAOYSA-N 1-[4-[3-(6-piperazin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]-3-(2-piperidin-4-ylsulfonylethyl)urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCNCC2)C=CC=1NC(=O)NCCS(=O)(=O)C1CCNCC1 JVXCLFRKMLYVPN-UHFFFAOYSA-N 0.000 claims description 3
- VFOJTZADMXSWDN-UHFFFAOYSA-N 1-[amino(benzenesulfonyl)amino]-3-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)NN(N)S(=O)(=O)C1=CC=CC=C1 VFOJTZADMXSWDN-UHFFFAOYSA-N 0.000 claims description 3
- MJNXPUUCHWFNTM-UHFFFAOYSA-N 1-piperazin-1-ylsulfonyl-3-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C1CNCCN1S(=O)(=O)NC(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC=CC=N1 MJNXPUUCHWFNTM-UHFFFAOYSA-N 0.000 claims description 3
- ZUKQENNJYHNWSQ-UHFFFAOYSA-N 1-piperazin-1-ylsulfonyl-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NS(=O)(=O)N1CCNCC1 ZUKQENNJYHNWSQ-UHFFFAOYSA-N 0.000 claims description 3
- ITOPIZNDSKMXEY-UHFFFAOYSA-N 1-piperazin-1-ylsulfonyl-3-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)NS(=O)(=O)N1CCNCC1 ITOPIZNDSKMXEY-UHFFFAOYSA-N 0.000 claims description 3
- FAUBUFWVUBDTCJ-UHFFFAOYSA-N 2,2-dimethyl-n-[1-[4-(3-quinoxalin-2-ylprop-2-enoyl)benzoyl]piperidin-4-yl]propanamide Chemical compound C1CC(NC(=O)C(C)(C)C)CCN1C(=O)C1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=C1 FAUBUFWVUBDTCJ-UHFFFAOYSA-N 0.000 claims description 3
- FDOSPHNXSYYUTA-UHFFFAOYSA-N 2,2-dimethylpropyl n-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC(C)(C)C)=CC=C1C(=O)C=CC1=CC(N2CCOCC2)=C(C=CC=C2)C2=N1 FDOSPHNXSYYUTA-UHFFFAOYSA-N 0.000 claims description 3
- DWLUSMRRGGUGDA-UHFFFAOYSA-N 2-(1,2,4-triazol-1-yl)ethyl n-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=NC=NN1CCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCOCC1 DWLUSMRRGGUGDA-UHFFFAOYSA-N 0.000 claims description 3
- VPDAUELYCVYSSG-UHFFFAOYSA-N 2-(1,2,4-triazol-1-yl)ethyl n-[4-[3-(6-piperazin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=NC=NN1CCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCNCC1 VPDAUELYCVYSSG-UHFFFAOYSA-N 0.000 claims description 3
- GQMBWIZXWWLPTL-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)ethyl n-[4-[3-[6-(4-methylpiperazin-1-yl)pyridin-2-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1CN(C)CCN1C1=CC=CC(C=CC(=O)C=2C=CC(NC(=O)OCCN3C(=CC(C)=N3)C)=CC=2)=N1 GQMBWIZXWWLPTL-UHFFFAOYSA-N 0.000 claims description 3
- CXLKCWGZUZITFG-UHFFFAOYSA-N 2-(benzenesulfonamido)ethyl n-[4-[3-[6-(4-methylpiperazin-1-yl)pyridin-2-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1CN(C)CCN1C1=CC=CC(C=CC(=O)C=2C=CC(NC(=O)OCCNS(=O)(=O)C=3C=CC=CC=3)=CC=2)=N1 CXLKCWGZUZITFG-UHFFFAOYSA-N 0.000 claims description 3
- YSFGROPCKNPUGY-UHFFFAOYSA-N 2-[(4-methylpiperazin-1-yl)sulfonylamino]ethyl n-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]carbamate Chemical compound C1CN(C)CCN1S(=O)(=O)NCCOC(=O)NC1=CC=C(C(=O)C=CC=2N=CC=CC=2)C=C1 YSFGROPCKNPUGY-UHFFFAOYSA-N 0.000 claims description 3
- UGODTVHLSVKISO-UHFFFAOYSA-N 2-[(4-methylpiperazin-1-yl)sulfonylamino]ethyl n-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]carbamate Chemical compound C1CN(C)CCN1S(=O)(=O)NCCOC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=C1 UGODTVHLSVKISO-UHFFFAOYSA-N 0.000 claims description 3
- LNMLKUUGLKVAQO-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)hydrazinyl]ethyl n-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]carbamate Chemical compound C=1C=CC=CC=1S(=O)(=O)NNCCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC=CC=N1 LNMLKUUGLKVAQO-UHFFFAOYSA-N 0.000 claims description 3
- VKRLKBNAUYJDFJ-UHFFFAOYSA-N 2-[amino(pyridin-2-yl)amino]ethyl n-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]carbamate Chemical compound C=1C=CC=NC=1N(N)CCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC=CC=N1 VKRLKBNAUYJDFJ-UHFFFAOYSA-N 0.000 claims description 3
- CLJWBHVEEGPPMG-UHFFFAOYSA-N 2-[amino(pyridin-2-yl)amino]ethyl n-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C=1C=CC=NC=1N(N)CCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCOCC1 CLJWBHVEEGPPMG-UHFFFAOYSA-N 0.000 claims description 3
- UTUMPXNGERRHPF-UHFFFAOYSA-N 2-[amino-(5-methyl-1,2-oxazol-3-yl)amino]ethyl n-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]carbamate Chemical compound O1C(C)=CC(N(N)CCOC(=O)NC=2C=CC(=CC=2)C(=O)C=CC=2N=CC=CC=2)=N1 UTUMPXNGERRHPF-UHFFFAOYSA-N 0.000 claims description 3
- CIKBGBSHXUAXCH-UHFFFAOYSA-N 2-methylpropyl n-[4-[3-(4-piperidin-1-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC(C)C)=CC=C1C(=O)C=CC1=CC(N2CCCCC2)=C(C=CC=C2)C2=N1 CIKBGBSHXUAXCH-UHFFFAOYSA-N 0.000 claims description 3
- FWPNNESZPAJBEK-UHFFFAOYSA-N 2-morpholin-4-yl-2-oxo-n-[4-(4,4,4-trifluoro-3-quinolin-3-ylbut-2-enoyl)phenyl]acetamide Chemical compound C=1N=C2C=CC=CC2=CC=1C(C(F)(F)F)=CC(=O)C(C=C1)=CC=C1NC(=O)C(=O)N1CCOCC1 FWPNNESZPAJBEK-UHFFFAOYSA-N 0.000 claims description 3
- KBDJNZQHZAYJSF-UHFFFAOYSA-N 2-morpholin-4-ylethyl n-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1COCCN1CCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCOCC1 KBDJNZQHZAYJSF-UHFFFAOYSA-N 0.000 claims description 3
- MAJRJMDOXPXQRA-UHFFFAOYSA-N 2-piperidin-1-ylethyl n-[4-[3-(6-piperidin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1CCCCN1CCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCCCC1 MAJRJMDOXPXQRA-UHFFFAOYSA-N 0.000 claims description 3
- LQEUKMWBBYMSDY-UHFFFAOYSA-N 2-pyridin-2-ylsulfonylethyl n-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C=1C=CC=NC=1S(=O)(=O)CCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCOCC1 LQEUKMWBBYMSDY-UHFFFAOYSA-N 0.000 claims description 3
- LUYQXFMHGFUNBL-UHFFFAOYSA-N 3-(6-piperidin-1-ylpyridin-3-yl)-1-[4-(pyrazole-1-carbonyl)phenyl]but-2-en-1-one Chemical compound C=1C=C(N2CCCCC2)N=CC=1C(C)=CC(=O)C(C=C1)=CC=C1C(=O)N1C=CC=N1 LUYQXFMHGFUNBL-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- WSEHEQQQAABODR-UHFFFAOYSA-N [4-[3-(6-piperidin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1C(=O)C=CC1=CC=CC(N2CCCCC2)=N1 WSEHEQQQAABODR-UHFFFAOYSA-N 0.000 claims description 3
- YFSAUMIMWOYZAO-UHFFFAOYSA-N ethyl n-[4-[3-(2-pyrrolidin-1-ylquinolin-3-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)C=CC1=CC2=CC=CC=C2N=C1N1CCCC1 YFSAUMIMWOYZAO-UHFFFAOYSA-N 0.000 claims description 3
- DNBCCTCVENITSE-UHFFFAOYSA-N ethyl n-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)C=CC1=CC(N2CCOCC2)=C(C=CC=C2)C2=N1 DNBCCTCVENITSE-UHFFFAOYSA-N 0.000 claims description 3
- PJOGOMRNMMDQAR-UHFFFAOYSA-N ethyl n-[4-[3-(4-piperidin-1-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)C=CC1=CC(N2CCCCC2)=C(C=CC=C2)C2=N1 PJOGOMRNMMDQAR-UHFFFAOYSA-N 0.000 claims description 3
- VQLMGOKCIMPUKM-UHFFFAOYSA-N ethyl n-[4-[3-(6-piperidin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)C=CC1=CC=CC(N2CCCCC2)=N1 VQLMGOKCIMPUKM-UHFFFAOYSA-N 0.000 claims description 3
- LRLAGRUNTSJZRC-UHFFFAOYSA-N ethyl n-[4-[3-[2-(4-hydroxypiperidin-1-yl)quinolin-3-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)C=CC1=CC2=CC=CC=C2N=C1N1CCC(O)CC1 LRLAGRUNTSJZRC-UHFFFAOYSA-N 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- IDHQAKCDFMUNMQ-UHFFFAOYSA-N furan-2-ylmethyl n-[4-[3-(6-piperidin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C=1C=COC=1COC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCCCC1 IDHQAKCDFMUNMQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- ABAALXVDKZVHMS-UHFFFAOYSA-N methyl 4-morpholin-4-yl-2-[3-oxo-3-[4-(pyrrolidine-1-carbonyl)phenyl]prop-1-enyl]quinoline-6-carboxylate Chemical compound C1=C(N2CCOCC2)C2=CC(C(=O)OC)=CC=C2N=C1C=CC(=O)C(C=C1)=CC=C1C(=O)N1CCCC1 ABAALXVDKZVHMS-UHFFFAOYSA-N 0.000 claims description 3
- NBBWHIASXDATSQ-UHFFFAOYSA-N methyl n-[2-[3-[4-[[2-(4-methylpiperazin-1-yl)-2-oxoacetyl]amino]phenyl]-3-oxoprop-1-enyl]quinolin-4-yl]carbamate Chemical compound N=1C2=CC=CC=C2C(NC(=O)OC)=CC=1C=CC(=O)C(C=C1)=CC=C1NC(=O)C(=O)N1CCN(C)CC1 NBBWHIASXDATSQ-UHFFFAOYSA-N 0.000 claims description 3
- MGZDLQNJKROEIL-UHFFFAOYSA-N methyl n-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(=O)C=CC1=CC(N2CCOCC2)=C(C=CC=C2)C2=N1 MGZDLQNJKROEIL-UHFFFAOYSA-N 0.000 claims description 3
- DAISSIUAPIKZPS-UHFFFAOYSA-N methyl n-[4-[3-[2-(4-hydroxypiperidin-1-yl)quinolin-3-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(=O)C=CC1=CC2=CC=CC=C2N=C1N1CCC(O)CC1 DAISSIUAPIKZPS-UHFFFAOYSA-N 0.000 claims description 3
- BAHPRIBPOPCEAQ-UHFFFAOYSA-N methyl n-[4-[3-[6-(thiadiazol-4-yl)quinolin-2-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(=O)C=CC1=CC=C(C=C(C=C2)C=3N=NSC=3)C2=N1 BAHPRIBPOPCEAQ-UHFFFAOYSA-N 0.000 claims description 3
- OWIXOTTWKCZJBK-UHFFFAOYSA-N methyl n-[5-methoxy-2-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC(OC)=CC=C1C(=O)C=CC1=CC(N2CCOCC2)=C(C=CC=C2)C2=N1 OWIXOTTWKCZJBK-UHFFFAOYSA-N 0.000 claims description 3
- LPYFDHREVBKELC-UHFFFAOYSA-N n'-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]-n-(2-pyridin-2-ylsulfonylethyl)oxamide Chemical compound C=1C=C(C(=O)C=CC=2N=CC=CC=2)C=CC=1NC(=O)C(=O)NCCS(=O)(=O)C1=CC=CC=N1 LPYFDHREVBKELC-UHFFFAOYSA-N 0.000 claims description 3
- HYUGYAJYINQMGL-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-n'-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)C(=O)NCCN1CCOCC1 HYUGYAJYINQMGL-UHFFFAOYSA-N 0.000 claims description 3
- RMLSNZDJZPCDAG-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-n'-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]oxamide Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)C(=O)NCCN1CCOCC1 RMLSNZDJZPCDAG-UHFFFAOYSA-N 0.000 claims description 3
- NPAFCMSMHULSJJ-UHFFFAOYSA-N n-(2-oxo-2-piperazin-1-ylethyl)-n'-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound C1CNCCN1C(=O)CNC(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC=CC=N1 NPAFCMSMHULSJJ-UHFFFAOYSA-N 0.000 claims description 3
- CYOYLHMYXYSHHN-UHFFFAOYSA-N n-(2-piperazin-1-ylethyl)-n'-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound C=1C=C(C(=O)C=CC=2N=CC=CC=2)C=CC=1NC(=O)C(=O)NCCN1CCNCC1 CYOYLHMYXYSHHN-UHFFFAOYSA-N 0.000 claims description 3
- GHUTWZKGYLXKBT-UHFFFAOYSA-N n-(2-pyridin-2-ylsulfonylethyl)-n'-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)C(=O)NCCS(=O)(=O)C1=CC=CC=N1 GHUTWZKGYLXKBT-UHFFFAOYSA-N 0.000 claims description 3
- UJERBCWBEUDUEZ-UHFFFAOYSA-N n-[1-[4-[4-(3-pyridin-2-ylprop-2-enoyl)benzoyl]piperazin-1-yl]piperidin-4-yl]methanesulfonamide Chemical compound C1CC(NS(=O)(=O)C)CCN1N1CCN(C(=O)C=2C=CC(=CC=2)C(=O)C=CC=2N=CC=CC=2)CC1 UJERBCWBEUDUEZ-UHFFFAOYSA-N 0.000 claims description 3
- LSPZFELUIYWOLQ-UHFFFAOYSA-N n-[2-(piperazin-1-ylsulfonylamino)ethyl]-n'-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound C=1C=C(C(=O)C=CC=2N=CC=CC=2)C=CC=1NC(=O)C(=O)NCCNS(=O)(=O)N1CCNCC1 LSPZFELUIYWOLQ-UHFFFAOYSA-N 0.000 claims description 3
- XBCJUFYBFBFZTC-UHFFFAOYSA-N n-[2-(piperidine-4-carbonylamino)ethyl]-n'-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound C1CNCCC1C(=O)NCCNC(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC=CC=N1 XBCJUFYBFBFZTC-UHFFFAOYSA-N 0.000 claims description 3
- LZNSJBMSTQYEIF-UHFFFAOYSA-N n-[2-[[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]carbamoylamino]ethyl]pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)C=CC=2N=CC=CC=2)C=CC=1NC(=O)NCCNC(=O)C1=CC=CN=C1 LZNSJBMSTQYEIF-UHFFFAOYSA-N 0.000 claims description 3
- PEEQIPPSBGGKAQ-UHFFFAOYSA-N n-[2-[[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamoylamino]ethyl]piperidine-4-carboxamide Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)NCCNC(=O)C1CCNCC1 PEEQIPPSBGGKAQ-UHFFFAOYSA-N 0.000 claims description 3
- KWEBXNDBSUJWGV-UHFFFAOYSA-N n-[2-[[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamoylamino]ethyl]pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)NCCNC(=O)C1=CC=CN=C1 KWEBXNDBSUJWGV-UHFFFAOYSA-N 0.000 claims description 3
- UVCAXSONWMFDJO-UHFFFAOYSA-N n-[2-[amino-(6-methylpyridin-2-yl)amino]ethyl]-n'-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound CC1=CC=CC(N(N)CCNC(=O)C(=O)NC=2C=CC(=CC=2)C(=O)C=CC=2N=CC=CC=2)=N1 UVCAXSONWMFDJO-UHFFFAOYSA-N 0.000 claims description 3
- OJSZMSJAJRTQPZ-UHFFFAOYSA-N n-[4-[3-(6-morpholin-4-ylpyridin-3-yl)but-2-enoyl]phenyl]morpholine-4-carboxamide Chemical compound C=1C=C(N2CCOCC2)N=CC=1C(C)=CC(=O)C(C=C1)=CC=C1NC(=O)N1CCOCC1 OJSZMSJAJRTQPZ-UHFFFAOYSA-N 0.000 claims description 3
- MGSNVPMFVNZOAI-UHFFFAOYSA-N n-[4-[4,4,4-trifluoro-3-(4-morpholin-4-ylquinolin-3-yl)but-2-enoyl]phenyl]morpholine-4-carboxamide Chemical compound C=1N=C2C=CC=CC2=C(N2CCOCC2)C=1C(C(F)(F)F)=CC(=O)C(C=C1)=CC=C1NC(=O)N1CCOCC1 MGSNVPMFVNZOAI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- PXWJSVWSQGKTPZ-UHFFFAOYSA-N phenyl n-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=C1C=CC=CC1=1)=CC=1N1CCOCC1 PXWJSVWSQGKTPZ-UHFFFAOYSA-N 0.000 claims description 3
- IWQCVJIRLWTILG-UHFFFAOYSA-N phenyl n-[4-[3-[2-(4-hydroxypiperidin-1-yl)quinolin-3-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1CC(O)CCN1C1=NC2=CC=CC=C2C=C1C=CC(=O)C(C=C1)=CC=C1NC(=O)OC1=CC=CC=C1 IWQCVJIRLWTILG-UHFFFAOYSA-N 0.000 claims description 3
- YSAGHKYDFUCMMF-UHFFFAOYSA-N phenyl n-[4-[3-[6-(thiadiazol-4-yl)quinolin-2-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=C1C=C2)=CC=C1C=C2C1=CSN=N1 YSAGHKYDFUCMMF-UHFFFAOYSA-N 0.000 claims description 3
- RFWZJKSNQWBQNM-UHFFFAOYSA-N phenyl n-[6-[3-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3-oxoprop-1-enyl]pyridin-2-yl]carbamate Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C(=O)C=CC=2N=C(NC(=O)OC=3C=CC=CC=3)C=CC=2)C=C1 RFWZJKSNQWBQNM-UHFFFAOYSA-N 0.000 claims description 3
- OIKQZEXSYMYBLR-UHFFFAOYSA-N piperidin-4-yl n-[4-[3-[6-(4-methylpiperazin-1-yl)pyridin-2-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1CN(C)CCN1C1=CC=CC(C=CC(=O)C=2C=CC(NC(=O)OC3CCNCC3)=CC=2)=N1 OIKQZEXSYMYBLR-UHFFFAOYSA-N 0.000 claims description 3
- QTUGKHOKNFMTTP-UHFFFAOYSA-N pyridin-2-ylmethyl n-[4-[3-(6-pyrrolidin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C=1C=CC=NC=1COC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCCC1 QTUGKHOKNFMTTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- IAHPSBDHHXVOLL-UHFFFAOYSA-N (1-methylpyrrol-3-yl) n-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound CN1C=CC(OC(=O)NC=2C=CC(=CC=2)C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)=C1 IAHPSBDHHXVOLL-UHFFFAOYSA-N 0.000 claims description 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
- LJYYOIBFHHDAJW-UHFFFAOYSA-N 1,2-oxazol-3-yl n-[4-[3-[6-(4-methylpiperazin-1-yl)pyridin-2-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1CN(C)CCN1C1=CC=CC(C=CC(=O)C=2C=CC(NC(=O)OC3=NOC=C3)=CC=2)=N1 LJYYOIBFHHDAJW-UHFFFAOYSA-N 0.000 claims description 2
- XQUKTEBLWVXVBZ-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NCCN1CCNCC1 XQUKTEBLWVXVBZ-UHFFFAOYSA-N 0.000 claims description 2
- BVPMJEBUNWEHIM-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)-3-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)NCCN1CCNCC1 BVPMJEBUNWEHIM-UHFFFAOYSA-N 0.000 claims description 2
- VWVSEGDXOYLOOF-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)-3-[4-[3-(6-piperidin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCCCC2)C=CC=1NC(=O)NCCN1CCNCC1 VWVSEGDXOYLOOF-UHFFFAOYSA-N 0.000 claims description 2
- XWUQJBJVENYVHV-UHFFFAOYSA-N 1-(2-pyridin-4-yloxyethyl)-3-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NCCOC1=CC=NC=C1 XWUQJBJVENYVHV-UHFFFAOYSA-N 0.000 claims description 2
- CYJIGNDQLVZTHP-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-[4-[3-(6-piperidin-1-ylpyridin-2-yl)prop-2-enoyl]phenyl]urea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(C(=O)C=CC=2N=C(C=CC=2)N2CCCCC2)C=C1 CYJIGNDQLVZTHP-UHFFFAOYSA-N 0.000 claims description 2
- LQKSDUSMDKSACE-UHFFFAOYSA-N 1-(4-methylthiophen-2-yl)-3-[4-[3-[4-piperidin-1-yl-6-(trifluoromethyl)quinolin-2-yl]prop-2-enoyl]phenyl]urea Chemical compound CC1=CSC(NC(=O)NC=2C=CC(=CC=2)C(=O)C=CC=2N=C3C=CC(=CC3=C(N3CCCCC3)C=2)C(F)(F)F)=C1 LQKSDUSMDKSACE-UHFFFAOYSA-N 0.000 claims description 2
- VXPFNDOCSCDDPU-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]urea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=C1C=CC=CC1=1)=CC=1N1CCOCC1 VXPFNDOCSCDDPU-UHFFFAOYSA-N 0.000 claims description 2
- ICXYDPITGSMJHO-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-[4-[3-(6-methyl-4-piperidin-1-ylquinolin-2-yl)prop-2-enoyl]phenyl]urea Chemical compound C1=C(N2CCCCC2)C2=CC(C)=CC=C2N=C1C=CC(=O)C(C=C1)=CC=C1NC(=O)NS(=O)(=O)C1=CC=CC=C1 ICXYDPITGSMJHO-UHFFFAOYSA-N 0.000 claims description 2
- XDBLWMZBIMNJKH-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-[4-[3-[6-(3,5-dimethylmorpholin-4-yl)pyridin-3-yl]prop-2-enoyl]phenyl]urea Chemical compound CC1COCC(C)N1C(N=C1)=CC=C1C=CC(=O)C(C=C1)=CC=C1NC(=O)NS(=O)(=O)C1=CC=CC=C1 XDBLWMZBIMNJKH-UHFFFAOYSA-N 0.000 claims description 2
- GJDKODXNFAWBCU-UHFFFAOYSA-N 1-[2-[2-(benzenesulfonyl)hydrazinyl]ethyl]-3-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=CC=CC=2)C=CC=1NC(=O)NCCNNS(=O)(=O)C1=CC=CC=C1 GJDKODXNFAWBCU-UHFFFAOYSA-N 0.000 claims description 2
- LJYMDNLHDMKISP-UHFFFAOYSA-N 1-[4-(3-quinolin-2-ylprop-2-enoyl)benzoyl]piperidin-4-one Chemical compound C=1C=C2C=CC=CC2=NC=1C=CC(=O)C(C=C1)=CC=C1C(=O)N1CCC(=O)CC1 LJYMDNLHDMKISP-UHFFFAOYSA-N 0.000 claims description 2
- BCVREBPAJZUQAX-UHFFFAOYSA-N 1-[4-(3-quinolin-2-ylprop-2-enoyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)C1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=C1 BCVREBPAJZUQAX-UHFFFAOYSA-N 0.000 claims description 2
- FGJWSTVHYNKVKX-UHFFFAOYSA-N 1-[4-(3-quinoxalin-2-ylprop-2-enoyl)benzoyl]piperidin-4-one Chemical compound C=1N=C2C=CC=CC2=NC=1C=CC(=O)C(C=C1)=CC=C1C(=O)N1CCC(=O)CC1 FGJWSTVHYNKVKX-UHFFFAOYSA-N 0.000 claims description 2
- IOLSPKYTZYCUFM-UHFFFAOYSA-N 1-[4-[3-(3-oxo-4h-quinoxalin-2-yl)prop-2-enoyl]benzoyl]pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)C1=CC=C(C(=O)C=CC=2C(=NC3=CC=CC=C3N=2)O)C=C1 IOLSPKYTZYCUFM-UHFFFAOYSA-N 0.000 claims description 2
- KNOBFAZZNHSEQJ-UHFFFAOYSA-N 1-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)C1=CC=CC=C1NC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=C(N3CCOCC3)C=2)C=C1 KNOBFAZZNHSEQJ-UHFFFAOYSA-N 0.000 claims description 2
- SDZWBGVCULIJNU-UHFFFAOYSA-N 1-[4-[3-(5,6,7-trimethoxy-6,7-dihydroquinolin-2-yl)prop-2-enoyl]benzoyl]piperidin-4-one Chemical compound C1=CC2=C(OC)C(OC)C(OC)C=C2N=C1C=CC(=O)C(C=C1)=CC=C1C(=O)N1CCC(=O)CC1 SDZWBGVCULIJNU-UHFFFAOYSA-N 0.000 claims description 2
- RKUHFXREVVQHDB-UHFFFAOYSA-N 1-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]-3-piperazin-1-ylsulfonylurea Chemical compound C1CNCCN1S(=O)(=O)NC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCOCC1 RKUHFXREVVQHDB-UHFFFAOYSA-N 0.000 claims description 2
- VLVDCPYDCKLQML-UHFFFAOYSA-N 1-[4-[3-[4-piperidin-1-yl-6-(trifluoromethyl)quinolin-2-yl]prop-2-enoyl]phenyl]-3-(2,3,4-trimethoxyphenyl)urea Chemical compound COC1=C(OC)C(OC)=CC=C1NC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC(=CC3=C(N3CCCCC3)C=2)C(F)(F)F)C=C1 VLVDCPYDCKLQML-UHFFFAOYSA-N 0.000 claims description 2
- AOXFJFGDKFESAD-UHFFFAOYSA-N 1-[5-[3-oxo-3-[4-(phenoxycarbonylamino)phenyl]prop-1-enyl]pyridin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(N=C1)=CC=C1C=CC(=O)C(C=C1)=CC=C1NC(=O)OC1=CC=CC=C1 AOXFJFGDKFESAD-UHFFFAOYSA-N 0.000 claims description 2
- DXKDKRKZKMNAAO-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]urea Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=C(N3CCOCC3)C=2)C=CC=1NC(=O)NC1CCCCC1 DXKDKRKZKMNAAO-UHFFFAOYSA-N 0.000 claims description 2
- JAZQZTPRISFTPQ-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[3-[4-piperidin-1-yl-6-(trifluoromethyl)quinolin-2-yl]prop-2-enoyl]phenyl]urea Chemical compound C1=C(N2CCCCC2)C2=CC(C(F)(F)F)=CC=C2N=C1C=CC(=O)C(C=C1)=CC=C1NC(=O)NC1CCCCC1 JAZQZTPRISFTPQ-UHFFFAOYSA-N 0.000 claims description 2
- FYYQRZPACSEVSH-UHFFFAOYSA-N 1-pyridin-2-yl-3-[4-[3-(2-pyrrolidin-1-ylquinolin-3-yl)prop-2-enoyl]phenyl]urea Chemical compound C=1C=CC=NC=1NC(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC2=CC=CC=C2N=C1N1CCCC1 FYYQRZPACSEVSH-UHFFFAOYSA-N 0.000 claims description 2
- KDCIGFGGMOAMQR-UHFFFAOYSA-N 2,2-dimethyl-n-[2-[3-oxo-3-[4-(pyrazole-1-carbonyl)phenyl]prop-1-enyl]quinolin-6-yl]propanamide Chemical compound C1=CC2=CC(NC(=O)C(C)(C)C)=CC=C2N=C1C=CC(=O)C(C=C1)=CC=C1C(=O)N1C=CC=N1 KDCIGFGGMOAMQR-UHFFFAOYSA-N 0.000 claims description 2
- OOMQYIVQXNEPKT-UHFFFAOYSA-N 2-(benzenesulfonamido)ethyl n-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]carbamate Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)OCCNS(=O)(=O)C1=CC=CC=C1 OOMQYIVQXNEPKT-UHFFFAOYSA-N 0.000 claims description 2
- GCLMCVBMSRINGQ-UHFFFAOYSA-N 2-(n-aminoanilino)-2-oxo-n-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]acetamide Chemical compound C=1C=CC=CC=1N(N)C(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC=CC=N1 GCLMCVBMSRINGQ-UHFFFAOYSA-N 0.000 claims description 2
- LVDLZIJGXUHIJH-UHFFFAOYSA-N 2-[(4-methylpiperazine-1-carbonyl)amino]ethyl n-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]carbamate Chemical compound C1CN(C)CCN1C(=O)NCCOC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=C1 LVDLZIJGXUHIJH-UHFFFAOYSA-N 0.000 claims description 2
- RCLBQELDFCVINO-UHFFFAOYSA-N 2-[3-[4-(3,5-dimethylpyrazole-1-carbonyl)phenyl]-3-oxoprop-1-enyl]quinoline-6-sulfonamide Chemical compound N1=C(C)C=C(C)N1C(=O)C1=CC=C(C(=O)C=CC=2N=C3C=CC(=CC3=CC=2)S(N)(=O)=O)C=C1 RCLBQELDFCVINO-UHFFFAOYSA-N 0.000 claims description 2
- AWDNALLYINNCHD-UHFFFAOYSA-N 2-[3-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3-oxoprop-1-enyl]-1h-quinazolin-4-one Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C(=O)C=CC=2NC(=O)C3=CC=CC=C3N=2)C=C1 AWDNALLYINNCHD-UHFFFAOYSA-N 0.000 claims description 2
- JLOWLSHUWIXYDS-UHFFFAOYSA-N 2-[3-[4-(morpholine-4-carbonyl)phenyl]-3-oxoprop-1-enyl]-1h-quinazolin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)NC=1C=CC(=O)C(C=C1)=CC=C1C(=O)N1CCOCC1 JLOWLSHUWIXYDS-UHFFFAOYSA-N 0.000 claims description 2
- DDLQCHJDUXCCJB-UHFFFAOYSA-N 2-[3-[4-[3-(dimethylamino)pyrazole-1-carbonyl]phenyl]-3-oxoprop-1-enyl]quinoline-6-sulfonamide Chemical compound N1=C(N(C)C)C=CN1C(=O)C1=CC=C(C(=O)C=CC=2N=C3C=CC(=CC3=CC=2)S(N)(=O)=O)C=C1 DDLQCHJDUXCCJB-UHFFFAOYSA-N 0.000 claims description 2
- YAVRTWRBFFSQMN-UHFFFAOYSA-N 2-[3-oxo-3-[4-(pyrazole-1-carbonyl)phenyl]prop-1-enyl]-1h-quinazolin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)NC=1C=CC(=O)C(C=C1)=CC=C1C(=O)N1C=CC=N1 YAVRTWRBFFSQMN-UHFFFAOYSA-N 0.000 claims description 2
- PYDVFBLZIXTMPB-UHFFFAOYSA-N 2-[amino-(6-methylpyridin-2-yl)amino]-2-oxo-n-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]acetamide Chemical compound CC1=CC=CC(N(N)C(=O)C(=O)NC=2C=CC(=CC=2)C(=O)C=CC=2N=C3C=CC=CC3=CC=2)=N1 PYDVFBLZIXTMPB-UHFFFAOYSA-N 0.000 claims description 2
- XKXHHOKEKUKZQG-UHFFFAOYSA-N 2-morpholin-4-yl-2-oxo-n-[4-(3-quinolin-2-ylprop-2-enoyl)phenyl]acetamide Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=CC=2)C=CC=1NC(=O)C(=O)N1CCOCC1 XKXHHOKEKUKZQG-UHFFFAOYSA-N 0.000 claims description 2
- HTXQVNMZJBYNOA-UHFFFAOYSA-N 2-morpholin-4-yl-2-oxo-n-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]acetamide Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)C(=O)N1CCOCC1 HTXQVNMZJBYNOA-UHFFFAOYSA-N 0.000 claims description 2
- VSZAPOOHNWSMFG-UHFFFAOYSA-N 2-morpholin-4-yl-2-oxo-n-[4-[3-(4-pyrrol-1-ylquinolin-2-yl)prop-2-enoyl]phenyl]acetamide Chemical compound C1COCCN1C(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=C1C=CC=CC1=1)=CC=1N1C=CC=C1 VSZAPOOHNWSMFG-UHFFFAOYSA-N 0.000 claims description 2
- RGXPPEZUMTUHLE-UHFFFAOYSA-N 2-morpholin-4-yl-n-[4-[3-(2-morpholin-4-ylquinolin-3-yl)prop-2-enoyl]phenyl]-2-oxoacetamide Chemical compound C1COCCN1C(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC2=CC=CC=C2N=C1N1CCOCC1 RGXPPEZUMTUHLE-UHFFFAOYSA-N 0.000 claims description 2
- KIVLBMWAZTVPRR-UHFFFAOYSA-N 2-morpholin-4-yl-n-[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]-2-oxoacetamide Chemical compound C1COCCN1C(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=C1C=CC=CC1=1)=CC=1N1CCOCC1 KIVLBMWAZTVPRR-UHFFFAOYSA-N 0.000 claims description 2
- NKBBHMPYXBDHFI-UHFFFAOYSA-N 2-oxo-2-piperidin-1-yl-n-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]acetamide Chemical compound C=1C=C(C(=O)C=CC=2N=C3C=CC=CC3=NC=2)C=CC=1NC(=O)C(=O)N1CCCCC1 NKBBHMPYXBDHFI-UHFFFAOYSA-N 0.000 claims description 2
- QKTZDTGHRCLHAX-UHFFFAOYSA-N 2-oxo-2-piperidin-1-yl-n-[4-[3-(2-piperidin-1-ylquinolin-3-yl)prop-2-enoyl]phenyl]acetamide Chemical compound C1CCCCN1C(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC2=CC=CC=C2N=C1N1CCCCC1 QKTZDTGHRCLHAX-UHFFFAOYSA-N 0.000 claims description 2
- MNWXYQXNQWELRB-UHFFFAOYSA-N 2-oxo-2-piperidin-1-yl-n-[4-[3-(4-pyrrol-1-ylquinolin-2-yl)prop-2-enoyl]phenyl]acetamide Chemical compound C1CCCCN1C(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=C1C=CC=CC1=1)=CC=1N1C=CC=C1 MNWXYQXNQWELRB-UHFFFAOYSA-N 0.000 claims description 2
- KUUUBQWVLQPGNE-UHFFFAOYSA-N 2-pyridin-2-ylsulfanylethyl n-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]carbamate Chemical compound C=1C=CC=NC=1SCCOC(=O)NC(C=C1)=CC=C1C(=O)C=CC(N=1)=CC=CC=1N1CCOCC1 KUUUBQWVLQPGNE-UHFFFAOYSA-N 0.000 claims description 2
- YXNQJFHDIDQEDK-UHFFFAOYSA-N 3-[3-oxo-3-[4-(4-oxopiperidine-1-carbonyl)phenyl]prop-1-enyl]-1h-quinoxalin-2-one Chemical compound OC1=NC2=CC=CC=C2N=C1C=CC(=O)C(C=C1)=CC=C1C(=O)N1CCC(=O)CC1 YXNQJFHDIDQEDK-UHFFFAOYSA-N 0.000 claims description 2
- OQVNUXIMIKZCBA-UHFFFAOYSA-N 4,4,4-trifluoro-1-[4-(morpholine-4-carbonyl)phenyl]-3-quinolin-3-ylbut-2-en-1-one Chemical compound C=1N=C2C=CC=CC2=CC=1C(C(F)(F)F)=CC(=O)C(C=C1)=CC=C1C(=O)N1CCOCC1 OQVNUXIMIKZCBA-UHFFFAOYSA-N 0.000 claims description 2
- CJRUNTZJXRAURI-UHFFFAOYSA-N 4-[[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamoylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=C(N3CCOCC3)C=2)C=C1 CJRUNTZJXRAURI-UHFFFAOYSA-N 0.000 claims description 2
- UWRPJLIACQBRMB-UHFFFAOYSA-N 4-[[4-[3-(4-piperidin-1-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamoylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=C(N3CCCCC3)C=2)C=C1 UWRPJLIACQBRMB-UHFFFAOYSA-N 0.000 claims description 2
- BRTZRIVZZGSIDZ-UHFFFAOYSA-N [1-[4-[4-(3-pyridin-2-ylprop-2-enoyl)benzoyl]piperazin-1-yl]piperidin-4-yl]sulfonylurea Chemical compound C1CC(S(=O)(=O)NC(=O)N)CCN1N1CCN(C(=O)C=2C=CC(=CC=2)C(=O)C=CC=2N=CC=CC=2)CC1 BRTZRIVZZGSIDZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- KIWZOXHOHVJCRE-UHFFFAOYSA-N ethyl 4-[[4-[3-(4-morpholin-4-ylquinolin-2-yl)prop-2-enoyl]phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)NC1=CC=C(C(=O)C=CC=2N=C3C=CC=CC3=C(N3CCOCC3)C=2)C=C1 KIWZOXHOHVJCRE-UHFFFAOYSA-N 0.000 claims description 2
- XEFXXOULOOLJTD-UHFFFAOYSA-N ethyl n-[2-[3-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3-oxoprop-1-enyl]quinolin-6-yl]carbamate Chemical compound C1=CC2=CC(NC(=O)OCC)=CC=C2N=C1C=CC(=O)C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 XEFXXOULOOLJTD-UHFFFAOYSA-N 0.000 claims description 2
- YKERLABQDQPUMD-UHFFFAOYSA-N ethyl n-[2-[3-[4-(ethoxycarbonylamino)phenyl]-3-oxoprop-1-enyl]quinolin-6-yl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(=O)C=CC1=CC=C(C=C(NC(=O)OCC)C=C2)C2=N1 YKERLABQDQPUMD-UHFFFAOYSA-N 0.000 claims description 2
- DHOFWLGNDJLSGU-UHFFFAOYSA-N ethyl n-[6-[3-[4-(benzenesulfonylcarbamoylamino)phenyl]-3-oxoprop-1-enyl]pyridin-2-yl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C=CC(=O)C=2C=CC(NC(=O)NS(=O)(=O)C=3C=CC=CC=3)=CC=2)=N1 DHOFWLGNDJLSGU-UHFFFAOYSA-N 0.000 claims description 2
- HFQLFMZEKLBVNB-UHFFFAOYSA-N ethyl n-[6-[3-oxo-3-[4-(4-pyridin-2-yloxypiperidine-1-carbonyl)phenyl]prop-1-enyl]pyridin-2-yl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C=CC(=O)C=2C=CC(=CC=2)C(=O)N2CCC(CC2)OC=2N=CC=CC=2)=N1 HFQLFMZEKLBVNB-UHFFFAOYSA-N 0.000 claims description 2
- CBZUYDQPNIWWBE-UHFFFAOYSA-N furan-2-ylmethyl n-[4-[3-[6-(4-methylpiperazin-1-yl)pyridin-2-yl]prop-2-enoyl]phenyl]carbamate Chemical compound C1CN(C)CCN1C1=CC=CC(C=CC(=O)C=2C=CC(NC(=O)OCC=3OC=CC=3)=CC=2)=N1 CBZUYDQPNIWWBE-UHFFFAOYSA-N 0.000 claims description 2
- VVYXKLMQDOSCEL-UHFFFAOYSA-N methyl 4-imidazol-1-yl-2-[3-oxo-3-[4-(trichloromethoxycarbonylamino)phenyl]prop-1-enyl]quinoline-6-carboxylate Chemical compound C1=C(N2C=NC=C2)C2=CC(C(=O)OC)=CC=C2N=C1C=CC(=O)C1=CC=C(NC(=O)OC(Cl)(Cl)Cl)C=C1 VVYXKLMQDOSCEL-UHFFFAOYSA-N 0.000 claims description 2
- XQBKADUZXIFZIG-UHFFFAOYSA-N methyl n-[6-[3-oxo-3-[4-[4-(pyrrolidine-1-carbonyl)piperidine-1-carbonyl]phenyl]prop-1-enyl]pyridin-2-yl]carbamate Chemical compound COC(=O)NC1=CC=CC(C=CC(=O)C=2C=CC(=CC=2)C(=O)N2CCC(CC2)C(=O)N2CCCC2)=N1 XQBKADUZXIFZIG-UHFFFAOYSA-N 0.000 claims description 2
- CFLXSNGHCUBWHR-UHFFFAOYSA-N n'-(benzenesulfonyl)-n-[4-(3-pyridin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)C(=O)NC(C=C1)=CC=C1C(=O)C=CC1=CC=CC=N1 CFLXSNGHCUBWHR-UHFFFAOYSA-N 0.000 claims description 2
- MYOUCFIWMYZQMB-UHFFFAOYSA-N n'-[4-(3-quinoxalin-2-ylprop-2-enoyl)phenyl]oxamide Chemical compound C1=CC(NC(=O)C(=O)N)=CC=C1C(=O)C=CC1=CN=C(C=CC=C2)C2=N1 MYOUCFIWMYZQMB-UHFFFAOYSA-N 0.000 claims description 2
- USAJOASTFOQXMD-UHFFFAOYSA-N n'-[4-[3-(2-morpholin-4-ylquinolin-3-yl)prop-2-enoyl]phenyl]oxamide Chemical compound C1=CC(NC(=O)C(=O)N)=CC=C1C(=O)C=CC1=CC2=CC=CC=C2N=C1N1CCOCC1 USAJOASTFOQXMD-UHFFFAOYSA-N 0.000 claims description 2
- NCGHRRWWODLOKV-UHFFFAOYSA-N n'-[4-[3-(2-piperidin-1-ylquinolin-3-yl)prop-2-enoyl]phenyl]oxamide Chemical compound C1=CC(NC(=O)C(=O)N)=CC=C1C(=O)C=CC1=CC2=CC=CC=C2N=C1N1CCCCC1 NCGHRRWWODLOKV-UHFFFAOYSA-N 0.000 claims description 2
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- FSFWSLDVZJKYME-UHFFFAOYSA-N n'-[4-[3-(6-morpholin-4-ylpyridin-2-yl)prop-2-enoyl]phenyl]-n-(2-piperazin-1-ylethyl)oxamide Chemical compound C=1C=C(C(=O)C=CC=2N=C(C=CC=2)N2CCOCC2)C=CC=1NC(=O)C(=O)NCCN1CCNCC1 FSFWSLDVZJKYME-UHFFFAOYSA-N 0.000 claims description 2
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- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Toxicology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN178KO2004 | 2004-04-12 | ||
| IN178/KOL/2004 | 2004-04-12 | ||
| PCT/IN2005/000112 WO2005097746A2 (en) | 2004-04-12 | 2005-04-11 | 2-propene-1-ones as hsp 70 inducers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2562130A1 CA2562130A1 (en) | 2005-10-20 |
| CA2562130C true CA2562130C (en) | 2011-06-07 |
Family
ID=34972223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2562130A Expired - Fee Related CA2562130C (en) | 2004-04-12 | 2005-04-11 | 2-propene-1-ones as hsp 70 inducers |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080207608A1 (OSRAM) |
| EP (1) | EP1748987A2 (OSRAM) |
| JP (1) | JP4790704B2 (OSRAM) |
| KR (1) | KR100825492B1 (OSRAM) |
| CN (1) | CN1964946A (OSRAM) |
| AU (1) | AU2005232159B2 (OSRAM) |
| BR (1) | BRPI0509799A (OSRAM) |
| CA (1) | CA2562130C (OSRAM) |
| MX (1) | MXPA06011770A (OSRAM) |
| RU (1) | RU2341522C2 (OSRAM) |
| WO (1) | WO2005097746A2 (OSRAM) |
| ZA (1) | ZA200608077B (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101679456B (zh) * | 2007-06-12 | 2012-09-05 | 霍夫曼-拉罗奇有限公司 | 噻唑并嘧啶类和它们作为磷脂酰肌醇3-激酶的抑制剂的应用 |
| KR100989093B1 (ko) | 2008-01-18 | 2010-10-25 | 한화제약주식회사 | 생강나무 가지의 추출물을 포함하는 심혈관계 질환의 예방 및 치료용 조성물 |
| KR101799429B1 (ko) * | 2010-05-03 | 2017-11-21 | 에스케이바이오팜 주식회사 | 신경 세포 사멸 또는 신경 퇴화를 억제하기 위한 약학적 조성물 |
| WO2013025498A1 (en) | 2011-08-12 | 2013-02-21 | Schubert David R | Neuroprotective polyphenol analogs |
| WO2013025484A1 (en) * | 2011-08-12 | 2013-02-21 | Lapchak Paul A | Polyphenol analogs to treat ischemia |
| WO2013148228A1 (en) * | 2012-03-29 | 2013-10-03 | Advanced Cancer Therapeutics, Llc | Pfkfb3 inhibitor and methods of use as an anti-cancer therapeutic |
| JPWO2014123203A1 (ja) * | 2013-02-06 | 2017-02-02 | 京都薬品工業株式会社 | 糖尿病治療薬 |
| WO2014164749A1 (en) | 2013-03-13 | 2014-10-09 | Forma Therapeutics, Inc. | Novel compounds and compositions for inhibition of fasn |
| WO2015187934A1 (en) * | 2014-06-06 | 2015-12-10 | Cureveda, Llc | Functionalized hetroaryl enones exhibiting nrf2 activation and their method of use |
| US10874101B2 (en) | 2014-08-25 | 2020-12-29 | Yasuo Yamauchi | Tolerance improving agent for plants |
| CN105237487B (zh) * | 2015-10-19 | 2017-10-10 | 安徽中医药大学 | 含川芎嗪基查尔酮芳氧烷酸类化合物、制备方法及其应用 |
| CA3005470A1 (en) * | 2015-11-20 | 2017-05-26 | Hoyun LEE | Quinolone chalcone compounds and uses thereof |
| CN105503745B (zh) * | 2016-01-07 | 2018-10-19 | 首都师范大学 | 含4-氧代喹唑啉-2-基的查耳酮类似物及其制备方法和用途 |
| CN108558763B (zh) * | 2018-05-16 | 2021-08-24 | 辽宁大学 | 含吲唑的查尔酮类衍生物及其应用 |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| US10793554B2 (en) | 2018-10-29 | 2020-10-06 | Forma Therapeutics, Inc. | Solid forms of 4-(2-fluoro-4-(1-methyl-1H-benzo[d]imidazol-5-yl)benzoyl)piperazin-1-yl)(1-hydroxycyclopropyl)methanone |
| CN111171018B (zh) * | 2018-11-13 | 2022-08-16 | 沈阳化工研究院有限公司 | 一种查尔酮类化合物及其应用 |
| CN109620827B (zh) * | 2018-12-14 | 2021-01-19 | 中国医学科学院医药生物技术研究所 | 杂环丙烯酮类化合物作为抗菌剂的用途 |
| EP4027994A4 (en) * | 2019-09-13 | 2024-03-27 | Dana-Farber Cancer Institute, Inc. | KDM INHIBITORS AND THEIR USES |
| CN114105927B (zh) * | 2020-08-31 | 2023-10-24 | 湖南超亟检测技术有限责任公司 | 一种苯并吡喃腈类荧光分子探针的构建及其体外诊断应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5348945A (en) * | 1990-04-06 | 1994-09-20 | Wake Forest University | Method of treatment with hsp70 |
| US5739170A (en) * | 1992-09-11 | 1998-04-14 | The Regents Of The University Of California | Inhibitors of metazoan parasite proteases |
| HU222994B1 (hu) * | 1995-11-02 | 2004-01-28 | BIOREX Kutató és Fejlesztő Rt. | Hidroxilaminszármazékok és azok alkalmazása sejtek molekuláris chaperon-termelésének fokozására alkalmas gyógyszerkészítmények előállítására |
| US6096711A (en) * | 1998-02-25 | 2000-08-01 | Sherman; Michael | Hsp72 induction and applications |
| WO2000018390A1 (fr) * | 1998-09-28 | 2000-04-06 | Hsp Research Institute, Inc. | Inducteurs d'expression de proteine de choc thermique |
| US6174875B1 (en) * | 1999-04-01 | 2001-01-16 | University Of Pittsburgh | Benzoquinoid ansamycins for the treatment of cardiac arrest and stroke |
| US7642367B2 (en) * | 2002-05-17 | 2010-01-05 | Lica Pharmaceuticals A/S | Diamino-functional chalcones |
| US7750160B2 (en) * | 2003-11-13 | 2010-07-06 | Ambit Biosciences Corporation | Isoxazolyl urea derivatives as kinase modulators |
-
2005
- 2005-04-11 AU AU2005232159A patent/AU2005232159B2/en not_active Ceased
- 2005-04-11 CN CNA2005800190202A patent/CN1964946A/zh active Pending
- 2005-04-11 CA CA2562130A patent/CA2562130C/en not_active Expired - Fee Related
- 2005-04-11 KR KR1020067023669A patent/KR100825492B1/ko not_active Expired - Fee Related
- 2005-04-11 US US11/578,354 patent/US20080207608A1/en not_active Abandoned
- 2005-04-11 WO PCT/IN2005/000112 patent/WO2005097746A2/en not_active Ceased
- 2005-04-11 JP JP2007507931A patent/JP4790704B2/ja not_active Expired - Fee Related
- 2005-04-11 RU RU2006139940/04A patent/RU2341522C2/ru not_active IP Right Cessation
- 2005-04-11 MX MXPA06011770A patent/MXPA06011770A/es active IP Right Grant
- 2005-04-11 BR BRPI0509799-1A patent/BRPI0509799A/pt not_active IP Right Cessation
- 2005-04-11 EP EP05752199A patent/EP1748987A2/en not_active Withdrawn
-
2006
- 2006-09-28 ZA ZA200608077A patent/ZA200608077B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06011770A (es) | 2007-04-13 |
| US20080207608A1 (en) | 2008-08-28 |
| KR20060135950A (ko) | 2006-12-29 |
| KR100825492B1 (ko) | 2008-04-28 |
| AU2005232159A1 (en) | 2005-10-20 |
| WO2005097746A3 (en) | 2006-01-19 |
| RU2006139940A (ru) | 2008-05-20 |
| JP4790704B2 (ja) | 2011-10-12 |
| ZA200608077B (en) | 2008-08-27 |
| CA2562130A1 (en) | 2005-10-20 |
| RU2341522C2 (ru) | 2008-12-20 |
| EP1748987A2 (en) | 2007-02-07 |
| JP2007532632A (ja) | 2007-11-15 |
| CN1964946A (zh) | 2007-05-16 |
| WO2005097746A2 (en) | 2005-10-20 |
| BRPI0509799A (pt) | 2007-11-13 |
| AU2005232159B2 (en) | 2008-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130411 |