JP5271897B2 - ポリ（ＡＤＰ−リボース）ポリメラーゼ（ＰＡＲＰ）の阻害剤としての、ピロロ［１，２−ａ］ピラジン−１（２Ｈ）−オン及びピロロ［１，２−ｄ］［１，２，４］トリアジン−１（２Ｈ）−オン誘導体 - Google Patents
ポリ（ＡＤＰ−リボース）ポリメラーゼ（ＰＡＲＰ）の阻害剤としての、ピロロ［１，２−ａ］ピラジン−１（２Ｈ）−オン及びピロロ［１，２−ｄ］［１，２，４］トリアジン−１（２Ｈ）−オン誘導体 Download PDFInfo
- Publication number
- JP5271897B2 JP5271897B2 JP2009512682A JP2009512682A JP5271897B2 JP 5271897 B2 JP5271897 B2 JP 5271897B2 JP 2009512682 A JP2009512682 A JP 2009512682A JP 2009512682 A JP2009512682 A JP 2009512682A JP 5271897 B2 JP5271897 B2 JP 5271897B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrazin
- methyl
- oxo
- dichloro
- dihydropyrrolo
- 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.)
- Expired - Fee Related
Links
- 239000003112 inhibitor Substances 0.000 title description 65
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 title description 37
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 title description 37
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 title description 34
- LFASPBCAVCUZES-UHFFFAOYSA-N 2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound O=C1NC=CN2C=CC=C12 LFASPBCAVCUZES-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 290
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 57
- 229910052760 oxygen Inorganic materials 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 53
- 229910052717 sulfur Inorganic materials 0.000 claims description 43
- 229920006395 saturated elastomer Polymers 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 230000036961 partial effect Effects 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- -1 Oxygen radical Chemical class 0.000 description 703
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical group [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 152
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 106
- 239000000203 mixture Substances 0.000 description 102
- 230000002829 reductive effect Effects 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
- 201000006417 multiple sclerosis Diseases 0.000 description 66
- 206010028980 Neoplasm Diseases 0.000 description 65
- 239000000243 solution Substances 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 238000005481 NMR spectroscopy Methods 0.000 description 55
- 238000011282 treatment Methods 0.000 description 55
- 201000011510 cancer Diseases 0.000 description 53
- 239000003814 drug Substances 0.000 description 53
- 238000000034 method Methods 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 39
- 239000000460 chlorine Substances 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 229940079593 drug Drugs 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
- 239000000047 product Substances 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000011734 sodium Substances 0.000 description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 238000011160 research Methods 0.000 description 29
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- 235000019439 ethyl acetate Nutrition 0.000 description 28
- 239000012661 PARP inhibitor Substances 0.000 description 27
- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 27
- 210000004027 cell Anatomy 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 239000013058 crude material Substances 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 21
- 108020004414 DNA Proteins 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- 238000000746 purification Methods 0.000 description 17
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- 230000002265 prevention Effects 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 230000008439 repair process Effects 0.000 description 15
- 238000004007 reversed phase HPLC Methods 0.000 description 15
- 230000001419 dependent effect Effects 0.000 description 14
- 229950006238 nadide Drugs 0.000 description 14
- 125000003373 pyrazinyl group Chemical group 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 230000002950 deficient Effects 0.000 description 13
- 230000006801 homologous recombination Effects 0.000 description 13
- 238000002744 homologous recombination Methods 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 125000004193 piperazinyl group Chemical group 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- 125000004076 pyridyl group Chemical group 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
- 239000002246 antineoplastic agent Substances 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 230000000144 pharmacologic effect Effects 0.000 description 11
- 125000003386 piperidinyl group Chemical group 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
- 108010064218 Poly (ADP-Ribose) Polymerase-1 Proteins 0.000 description 10
- 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 description 10
- 230000027455 binding Effects 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 102000006495 integrins Human genes 0.000 description 10
- 108010044426 integrins Proteins 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 108010016731 PPAR gamma Proteins 0.000 description 9
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 9
- 239000000556 agonist Substances 0.000 description 9
- 208000027866 inflammatory disease Diseases 0.000 description 9
- 230000037361 pathway Effects 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 9
- 125000000168 pyrrolyl group Chemical group 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000004037 angiogenesis inhibitor Substances 0.000 description 8
- 229940121369 angiogenesis inhibitor Drugs 0.000 description 8
- 125000002393 azetidinyl group Chemical group 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
- 229940127089 cytotoxic agent Drugs 0.000 description 8
- 239000002254 cytotoxic agent Substances 0.000 description 8
- 206010012601 diabetes mellitus Diseases 0.000 description 8
- 125000005959 diazepanyl group Chemical group 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 8
- 230000000302 ischemic effect Effects 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000002953 preparative HPLC Methods 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 8
- 238000001959 radiotherapy Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 102100023652 Poly [ADP-ribose] polymerase 2 Human genes 0.000 description 7
- 206010063837 Reperfusion injury Diseases 0.000 description 7
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 230000004663 cell proliferation Effects 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000002834 estrogen receptor modulator Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 229960004964 temozolomide Drugs 0.000 description 7
- 239000003558 transferase inhibitor Substances 0.000 description 7
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 102000052609 BRCA2 Human genes 0.000 description 6
- 108700020462 BRCA2 Proteins 0.000 description 6
- 229940122361 Bisphosphonate Drugs 0.000 description 6
- 101150008921 Brca2 gene Proteins 0.000 description 6
- 208000024172 Cardiovascular disease Diseases 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 101710144590 Poly [ADP-ribose] polymerase 2 Proteins 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 208000006011 Stroke Diseases 0.000 description 6
- 239000012317 TBTU Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000004663 bisphosphonates Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000002541 furyl group Chemical group 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 6
- 229960004768 irinotecan Drugs 0.000 description 6
- 208000028867 ischemia Diseases 0.000 description 6
- 230000036457 multidrug resistance Effects 0.000 description 6
- 230000004770 neurodegeneration Effects 0.000 description 6
- 108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 description 6
- 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 6
- 239000003755 preservative agent Substances 0.000 description 6
- 235000018102 proteins Nutrition 0.000 description 6
- 102000027483 retinoid hormone receptors Human genes 0.000 description 6
- 108091008679 retinoid hormone receptors Proteins 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 239000000849 selective androgen receptor modulator Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 125000003003 spiro group Chemical group 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
- DELHFEJOUTYMDO-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(1,4-diazepan-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;chloride Chemical compound [Cl-].FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCC[NH2+]CC1 DELHFEJOUTYMDO-UHFFFAOYSA-N 0.000 description 5
- RVPANQUSAILHER-UHFFFAOYSA-N 6,7-dichloro-4-[[4-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]pyridin-1-ium-2-yl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N1C(=O)C2=CC(Cl)=C(Cl)N2C(CC=2[NH+]=CC=C(C=2)C(=O)N2CC3=NN=C(N3CC2)C(F)(F)F)=C1 RVPANQUSAILHER-UHFFFAOYSA-N 0.000 description 5
- QNQXPTXAYKICRO-UHFFFAOYSA-N 7,8-dichloro-4-[[3-(1,4-diazepan-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C=C(Cl)C(Cl)=C3C(=O)NC=2)C=C1C(=O)N1CCC[NH2+]CC1 QNQXPTXAYKICRO-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 230000005778 DNA damage Effects 0.000 description 5
- 231100000277 DNA damage Toxicity 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 description 5
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 5
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 5
- 102000004357 Transferases Human genes 0.000 description 5
- 108090000992 Transferases Proteins 0.000 description 5
- 230000001154 acute effect Effects 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 230000001028 anti-proliverative effect Effects 0.000 description 5
- 230000006907 apoptotic process Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 230000012820 cell cycle checkpoint Effects 0.000 description 5
- 230000030833 cell death Effects 0.000 description 5
- 230000001413 cellular effect Effects 0.000 description 5
- 238000002512 chemotherapy Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 231100000433 cytotoxic Toxicity 0.000 description 5
- 231100000599 cytotoxic agent Toxicity 0.000 description 5
- 230000001472 cytotoxic effect Effects 0.000 description 5
- 229960003901 dacarbazine Drugs 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 5
- 125000002632 imidazolidinyl group Chemical group 0.000 description 5
- 239000000411 inducer Substances 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- 230000000394 mitotic effect Effects 0.000 description 5
- JJAHKALBSXXBND-UHFFFAOYSA-N n-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorophenyl]azetidin-1-ium-3-carboxamide;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1NC(=O)C1C[NH2+]C1 JJAHKALBSXXBND-UHFFFAOYSA-N 0.000 description 5
- 208000004235 neutropenia Diseases 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 description 5
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 5
- 229960000624 procarbazine Drugs 0.000 description 5
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 5
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 5
- 238000012552 review Methods 0.000 description 5
- 230000035939 shock Effects 0.000 description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
- 230000007755 survival signaling Effects 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229940124597 therapeutic agent Drugs 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- PHQXHIWKCSGYDM-UHFFFAOYSA-N 3,4-dichloro-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C=1NC=C(Cl)C=1Cl PHQXHIWKCSGYDM-UHFFFAOYSA-N 0.000 description 4
- MNMMKOBJLQMWLQ-UHFFFAOYSA-N 4,5-dichloro-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)N1 MNMMKOBJLQMWLQ-UHFFFAOYSA-N 0.000 description 4
- WGWUEZVWFCOYAZ-UHFFFAOYSA-N 5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=C1 WGWUEZVWFCOYAZ-UHFFFAOYSA-N 0.000 description 4
- 108010004586 Ataxia Telangiectasia Mutated Proteins Proteins 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 description 4
- 208000031229 Cardiomyopathies Diseases 0.000 description 4
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 4
- 230000033616 DNA repair Effects 0.000 description 4
- 102100029094 DNA repair endonuclease XPF Human genes 0.000 description 4
- 102100039116 DNA repair protein RAD50 Human genes 0.000 description 4
- 102100034483 DNA repair protein RAD51 homolog 4 Human genes 0.000 description 4
- 101000743929 Homo sapiens DNA repair protein RAD50 Proteins 0.000 description 4
- 101001132266 Homo sapiens DNA repair protein RAD51 homolog 4 Proteins 0.000 description 4
- 206010021143 Hypoxia Diseases 0.000 description 4
- 102000010638 Kinesin Human genes 0.000 description 4
- 108010063296 Kinesin Proteins 0.000 description 4
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 102000001195 RAD51 Human genes 0.000 description 4
- 108010068097 Rad51 Recombinase Proteins 0.000 description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 206010047700 Vomiting Diseases 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 208000007502 anemia Diseases 0.000 description 4
- 230000003474 anti-emetic effect Effects 0.000 description 4
- 239000002111 antiemetic agent Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000003443 antiviral agent Substances 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229940127093 camptothecin Drugs 0.000 description 4
- 229960004562 carboplatin Drugs 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- 229960004316 cisplatin Drugs 0.000 description 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000000824 cytostatic agent Substances 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 235000003599 food sweetener Nutrition 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 239000003102 growth factor Substances 0.000 description 4
- 210000002216 heart Anatomy 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000005865 ionizing radiation Effects 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000002757 morpholinyl group Chemical group 0.000 description 4
- 230000035772 mutation Effects 0.000 description 4
- 239000002742 neurokinin 1 receptor antagonist Substances 0.000 description 4
- 238000011275 oncology therapy Methods 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 230000010410 reperfusion Effects 0.000 description 4
- 238000010561 standard procedure Methods 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 4
- 125000003831 tetrazolyl group Chemical group 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 125000001425 triazolyl group Chemical group 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 208000019553 vascular disease Diseases 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- UKLOTOWQAZVCIS-UHFFFAOYSA-N 2,2,2-trichloro-1-(4-chloro-1h-pyrrol-2-yl)ethanone Chemical compound ClC1=CNC(C(=O)C(Cl)(Cl)Cl)=C1 UKLOTOWQAZVCIS-UHFFFAOYSA-N 0.000 description 3
- TWDBZTURBXMHOG-UHFFFAOYSA-N 2-[4-[5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-1,4-diazepan-1-yl]-N-methylacetamide Chemical compound C1CN(CC(=O)NC)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F TWDBZTURBXMHOG-UHFFFAOYSA-N 0.000 description 3
- XTWQFWZBXZCEGP-UHFFFAOYSA-N 3-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorophenyl]-5-methylimidazolidine-2,4-dione Chemical compound O=C1C(C)NC(=O)N1C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F XTWQFWZBXZCEGP-UHFFFAOYSA-N 0.000 description 3
- OWYYGTWUPHVWAR-UHFFFAOYSA-N 4-[(3-amino-4-fluorophenyl)methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(F)C(N)=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=C1 OWYYGTWUPHVWAR-UHFFFAOYSA-N 0.000 description 3
- WLIXQOLBQNYYOO-UHFFFAOYSA-N 4-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-n-(3-fluorophenyl)piperazine-1-carboxamide Chemical compound FC1=CC=CC(NC(=O)N2CCN(CC2)C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)=C1 WLIXQOLBQNYYOO-UHFFFAOYSA-N 0.000 description 3
- PUAVIRQWDQMZBS-UHFFFAOYSA-N 4-[[3-(1,4-diazepane-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=CC=C3C(=O)NC=2)C=C1C(=O)N1CCCNCC1 PUAVIRQWDQMZBS-UHFFFAOYSA-N 0.000 description 3
- YOTWVAYGATYZPA-UHFFFAOYSA-N 4-chloro-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CN1 YOTWVAYGATYZPA-UHFFFAOYSA-N 0.000 description 3
- XBKXFEFDSBITQN-UHFFFAOYSA-N 5-[(7,8-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzamide Chemical compound C1=C(F)C(C(=O)N)=CC(CC=2N3C=C(Cl)C(Cl)=C3C(=O)NC=2)=C1 XBKXFEFDSBITQN-UHFFFAOYSA-N 0.000 description 3
- WQLWIEXSRUDBCH-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(1,4-diazepan-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCC[NH2+]CC1 WQLWIEXSRUDBCH-UHFFFAOYSA-N 0.000 description 3
- FIXJNKZXPREBSP-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(3,3-difluoroazetidin-1-ium-1-yl)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1[NH+]1CC(F)(F)C1 FIXJNKZXPREBSP-UHFFFAOYSA-N 0.000 description 3
- ZTDUIGWNNKEMOQ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(3-pyrrolidin-1-yl-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCN2C1=NN=C2N1CCCC1 ZTDUIGWNNKEMOQ-UHFFFAOYSA-N 0.000 description 3
- PDKZBVVFKOWGCQ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-piperidin-1-ium-1-ylpiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1[NH+]1CCCCC1 PDKZBVVFKOWGCQ-UHFFFAOYSA-N 0.000 description 3
- NNKKJYKDPPOMRJ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-propanoylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)CC)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F NNKKJYKDPPOMRJ-UHFFFAOYSA-N 0.000 description 3
- HVKGBUOWSSCKRD-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(piperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCNCC1 HVKGBUOWSSCKRD-UHFFFAOYSA-N 0.000 description 3
- DUTASWPZTVAFEL-UHFFFAOYSA-N 6-chloro-4-[[3-(1,4-diazepan-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-7-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.ClC1=C(C)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=C(F)C=1C(=O)N1CCC[NH2+]CC1 DUTASWPZTVAFEL-UHFFFAOYSA-N 0.000 description 3
- 102000009062 ADP Ribose Transferases Human genes 0.000 description 3
- 108010049290 ADP Ribose Transferases Proteins 0.000 description 3
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 3
- 206010003571 Astrocytoma Diseases 0.000 description 3
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 3
- 108700020463 BRCA1 Proteins 0.000 description 3
- 102000036365 BRCA1 Human genes 0.000 description 3
- 101150072950 BRCA1 gene Proteins 0.000 description 3
- 206010006187 Breast cancer Diseases 0.000 description 3
- 102100025399 Breast cancer type 2 susceptibility protein Human genes 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 3
- 241000282693 Cercopithecidae Species 0.000 description 3
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 3
- 231100001074 DNA strand break Toxicity 0.000 description 3
- 108010027673 Fanconi Anemia Complementation Group C protein Proteins 0.000 description 3
- 102000018825 Fanconi Anemia Complementation Group C protein Human genes 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 3
- 208000032456 Hemorrhagic Shock Diseases 0.000 description 3
- 101000934858 Homo sapiens Breast cancer type 2 susceptibility protein Proteins 0.000 description 3
- 101000891683 Homo sapiens Fanconi anemia group D2 protein Proteins 0.000 description 3
- 206010061216 Infarction Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 206010028851 Necrosis Diseases 0.000 description 3
- 206010033128 Ovarian cancer Diseases 0.000 description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- 102100032347 Poly(ADP-ribose) glycohydrolase Human genes 0.000 description 3
- 108091026813 Poly(ADPribose) Proteins 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 208000017442 Retinal disease Diseases 0.000 description 3
- 206010038997 Retroviral infections Diseases 0.000 description 3
- 206010049771 Shock haemorrhagic Diseases 0.000 description 3
- UIRKNQLZZXALBI-MSVGPLKSSA-N Squalamine Chemical compound C([C@@H]1C[C@H]2O)[C@@H](NCCCNCCCCN)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@H](C(C)C)OS(O)(=O)=O)[C@@]2(C)CC1 UIRKNQLZZXALBI-MSVGPLKSSA-N 0.000 description 3
- UIRKNQLZZXALBI-UHFFFAOYSA-N Squalamine Natural products OC1CC2CC(NCCCNCCCCN)CCC2(C)C2C1C1CCC(C(C)CCC(C(C)C)OS(O)(=O)=O)C1(C)CC2 UIRKNQLZZXALBI-UHFFFAOYSA-N 0.000 description 3
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 3
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 3
- 229960000643 adenine Drugs 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 230000001668 ameliorated effect Effects 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- 230000033115 angiogenesis Effects 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 125000003725 azepanyl group Chemical group 0.000 description 3
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003246 corticosteroid Substances 0.000 description 3
- 229960001334 corticosteroids Drugs 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 3
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 3
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 3
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 210000002950 fibroblast Anatomy 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 238000001415 gene therapy Methods 0.000 description 3
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 230000000091 immunopotentiator Effects 0.000 description 3
- 230000007574 infarction Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 238000007913 intrathecal administration Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 230000002147 killing effect Effects 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 3
- 208000031225 myocardial ischemia Diseases 0.000 description 3
- 230000017074 necrotic cell death Effects 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 229960003966 nicotinamide Drugs 0.000 description 3
- 235000005152 nicotinamide Nutrition 0.000 description 3
- 239000011570 nicotinamide Substances 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 229940127084 other anti-cancer agent Drugs 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 108010078356 poly ADP-ribose glycohydrolase Proteins 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000003233 pyrroles Chemical class 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 229950001248 squalamine Drugs 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 3
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 3
- 229960000303 topotecan Drugs 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 3
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JLXSYISXUJJGPA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-chloro-1h-pyrrole-2-carboxylate Chemical compound ClC1=CNC(C(=O)ON2C(CCC2=O)=O)=C1 JLXSYISXUJJGPA-UHFFFAOYSA-N 0.000 description 2
- YIOOMYJMTOZRGY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-methyl-1H-pyrrole-2-carboxylate Chemical compound CC1=CNC(C(=O)ON2C(CCC2=O)=O)=C1 YIOOMYJMTOZRGY-UHFFFAOYSA-N 0.000 description 2
- JYQWKPMPTMJFCY-BYPYZUCNSA-N (2s)-2-(ethoxycarbonylamino)propanoic acid Chemical compound CCOC(=O)N[C@@H](C)C(O)=O JYQWKPMPTMJFCY-BYPYZUCNSA-N 0.000 description 2
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XCUIIYBHLQAKDK-UHFFFAOYSA-N 2-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=C1 XCUIIYBHLQAKDK-UHFFFAOYSA-N 0.000 description 2
- WYVOPAFVJIUNLJ-UHFFFAOYSA-N 2-[3-[(2,4-dimethoxyphenyl)methylamino]prop-1-ynyl]pyridine-4-carbonitrile Chemical compound COC1=CC(OC)=CC=C1CNCC#CC1=CC(C#N)=CC=N1 WYVOPAFVJIUNLJ-UHFFFAOYSA-N 0.000 description 2
- WYHRKZGNJQCOLK-UHFFFAOYSA-N 2-[4-[5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-1,4-diazepan-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F WYHRKZGNJQCOLK-UHFFFAOYSA-N 0.000 description 2
- AYCCEPLQHDPHIY-UHFFFAOYSA-N 2-fluoro-4-[(1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC(CC=2N3C=CC=C3C(=O)NC=2)=C1 AYCCEPLQHDPHIY-UHFFFAOYSA-N 0.000 description 2
- FOCKAVKKIHZWED-UHFFFAOYSA-N 2-fluoro-5-[(1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]benzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(CC=2N3C=CC=C3C(=O)NC=2)=C1 FOCKAVKKIHZWED-UHFFFAOYSA-N 0.000 description 2
- HHUKJIOFLUNERQ-UHFFFAOYSA-N 2-fluoro-5-[(7-methyl-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]benzoic acid Chemical compound C1=C(C)C=C(C(NC=2)=O)N1C=2CC1=CC=C(F)C(C(O)=O)=C1 HHUKJIOFLUNERQ-UHFFFAOYSA-N 0.000 description 2
- KZDKWTUZEFWFLK-UHFFFAOYSA-N 2-fluoro-5-[(7-methyl-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]benzonitrile Chemical compound C1=C(C)C=C(C(NC=2)=O)N1C=2CC1=CC=C(F)C(C#N)=C1 KZDKWTUZEFWFLK-UHFFFAOYSA-N 0.000 description 2
- BIZHQRAAZMDWNK-UHFFFAOYSA-N 2-fluoro-5-iodobenzonitrile Chemical compound FC1=CC=C(I)C=C1C#N BIZHQRAAZMDWNK-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- FIHFNORJELJQFV-UHFFFAOYSA-N 3-(3-cyano-4-fluorophenyl)prop-2-ynyl-[(2,4-dimethoxyphenyl)methyl]azanium;chloride Chemical compound [Cl-].COC1=CC(OC)=CC=C1C[NH2+]CC#CC1=CC=C(F)C(C#N)=C1 FIHFNORJELJQFV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OHSWUUVPOIPPSZ-UHFFFAOYSA-N 4-(4-iodopyridine-2-carbonyl)-1,4-diazepane-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCCN1C(=O)C1=CC(I)=CC=N1 OHSWUUVPOIPPSZ-UHFFFAOYSA-N 0.000 description 2
- VVZJMILYQZXVGD-UHFFFAOYSA-N 4-[4-[3-[(4-chloro-1H-pyrrole-2-carbonyl)-[(2,4-dimethoxyphenyl)methyl]amino]prop-1-ynyl]pyridine-2-carbonyl]-1,4-diazepane-1-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1CN(C(=O)C=1NC=C(Cl)C=1)CC#CC1=CC=NC(C(=O)N2CCN(CCC2)C(O)=O)=C1 VVZJMILYQZXVGD-UHFFFAOYSA-N 0.000 description 2
- MHSPIBNZNRWJTE-UHFFFAOYSA-N 4-[4-[[7-chloro-2-[(2,4-dimethoxyphenyl)methyl]-1-oxopyrrolo[1,2-a]pyrazin-4-yl]methyl]pyridine-2-carbonyl]-1,4-diazepane-1-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1CN1C(=O)C2=CC(Cl)=CN2C(CC=2C=C(N=CC=2)C(=O)N2CCN(CCC2)C(O)=O)=C1 MHSPIBNZNRWJTE-UHFFFAOYSA-N 0.000 description 2
- JMDCVKIGRLSRNT-UHFFFAOYSA-N 4-[[3-(1,4-diazepan-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-7-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=C(C)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=C(F)C=1C(=O)N1CCC[NH2+]CC1 JMDCVKIGRLSRNT-UHFFFAOYSA-N 0.000 description 2
- FAUHOUDPXZQRLB-UHFFFAOYSA-N 4-[[3-(1,4-diazepane-1-carbonyl)-4-fluorophenyl]methyl]-7-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(C)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=C(F)C=1C(=O)N1CCCNCC1 FAUHOUDPXZQRLB-UHFFFAOYSA-N 0.000 description 2
- IWWVKBUNCYATCF-UHFFFAOYSA-N 4-[[3-(4-acetyl-1,4-diazepane-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C)CCCN1C(=O)C1=CC(CC=2N3C=CC=C3C(=O)NC=2)=CC=C1F IWWVKBUNCYATCF-UHFFFAOYSA-N 0.000 description 2
- PYYCYUPPEICLBG-UHFFFAOYSA-N 4-[[3-[4-(2-aminoethyl)-1,4-diazepane-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CCN)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F PYYCYUPPEICLBG-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- WQTUCQYVWQAXSJ-UHFFFAOYSA-N 4-chloro-n-[3-(3-cyano-4-fluorophenyl)prop-2-ynyl]-n-[(2,4-dimethoxyphenyl)methyl]-1h-pyrrole-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1CN(C(=O)C=1NC=C(Cl)C=1)CC#CC1=CC=C(F)C(C#N)=C1 WQTUCQYVWQAXSJ-UHFFFAOYSA-N 0.000 description 2
- YXYAHRAFINYJPL-UHFFFAOYSA-N 4-methyl-1h-pyrrole-2-carboxylic acid Chemical compound CC1=CNC(C(O)=O)=C1 YXYAHRAFINYJPL-UHFFFAOYSA-N 0.000 description 2
- 102000035037 5-HT3 receptors Human genes 0.000 description 2
- 108091005477 5-HT3 receptors Proteins 0.000 description 2
- ZULDSIFYDVDKFG-UHFFFAOYSA-N 5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1CC1=CNC(=O)C2=CC(Cl)=C(Cl)N12 ZULDSIFYDVDKFG-UHFFFAOYSA-N 0.000 description 2
- ZPGQULYKGAWACZ-UHFFFAOYSA-N 5-[(6-chloro-7-methyl-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoic acid Chemical compound ClC1=C(C)C=C(C(NC=2)=O)N1C=2CC1=CC=C(F)C(C(O)=O)=C1 ZPGQULYKGAWACZ-UHFFFAOYSA-N 0.000 description 2
- PZSKNTXKORUVLC-UHFFFAOYSA-N 5-[(7-chloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(CC=2N3C=C(Cl)C=C3C(=O)NC=2)=C1 PZSKNTXKORUVLC-UHFFFAOYSA-N 0.000 description 2
- MXWVDBVKIVIMGG-UHFFFAOYSA-N 5-[(7-chloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1CC1=CNC(=O)C2=CC(Cl)=CN12 MXWVDBVKIVIMGG-UHFFFAOYSA-N 0.000 description 2
- IVWRCOIGIJIHJL-UHFFFAOYSA-N 5-[[2-[(2,4-dimethoxyphenyl)methyl]-7-methyl-1-oxopyrrolo[1,2-a]pyrazin-4-yl]methyl]-2-fluorobenzonitrile Chemical compound COC1=CC(OC)=CC=C1CN1C(=O)C2=CC(C)=CN2C(CC=2C=C(C(F)=CC=2)C#N)=C1 IVWRCOIGIJIHJL-UHFFFAOYSA-N 0.000 description 2
- JVABMEDXURZYKR-UHFFFAOYSA-N 5-[[7-chloro-2-[(2,4-dimethoxyphenyl)methyl]-1-oxopyrrolo[1,2-a]pyrazin-4-yl]methyl]-2-fluorobenzonitrile Chemical compound COC1=CC(OC)=CC=C1CN1C(=O)C2=CC(Cl)=CN2C(CC=2C=C(C(F)=CC=2)C#N)=C1 JVABMEDXURZYKR-UHFFFAOYSA-N 0.000 description 2
- UFYABCWJPZTWHA-UHFFFAOYSA-N 5-methyl-1h-pyrrole-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)N1 UFYABCWJPZTWHA-UHFFFAOYSA-N 0.000 description 2
- KRVUNMSOWZKYTH-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(4-ethylsulfonylpiperazine-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(S(=O)(=O)CC)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F KRVUNMSOWZKYTH-UHFFFAOYSA-N 0.000 description 2
- PRYYBKNDHCXIDC-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-[2-(dimethylamino)ethyl]-1,4-diazepane-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CCN(C)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F PRYYBKNDHCXIDC-UHFFFAOYSA-N 0.000 description 2
- NXJBDKCBXCPRNC-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(methylaminomethyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(F)C(CNC)=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=C1 NXJBDKCBXCPRNC-UHFFFAOYSA-N 0.000 description 2
- DPYGUECUAJLNRJ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[3-(piperidine-1-carbonyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCN2C1=NN=C2C(=O)N1CCCCC1 DPYGUECUAJLNRJ-UHFFFAOYSA-N 0.000 description 2
- NHZVEVPRMUWGIM-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-methylpyrrolidin-1-ium-2-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCN1C(=O)C1(C)CCC[NH2+]1 NHZVEVPRMUWGIM-UHFFFAOYSA-N 0.000 description 2
- UVZOYPJUDULRAQ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-methyl-1,2,5-oxadiazol-3-yl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound CC1=NON=C1N1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 UVZOYPJUDULRAQ-UHFFFAOYSA-N 0.000 description 2
- VOZPJNIPXVQSHW-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=NN=C(C(F)(F)F)S1 VOZPJNIPXVQSHW-UHFFFAOYSA-N 0.000 description 2
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
- FGFKDJAYDUBAPV-UHFFFAOYSA-N 7-chloro-4-[[2-(1,4-diazepan-4-ium-1-carbonyl)pyridin-1-ium-4-yl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.C1=C(Cl)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=[NH+]C=1C(=O)N1CCC[NH2+]CC1 FGFKDJAYDUBAPV-UHFFFAOYSA-N 0.000 description 2
- LXESPGUPGCNDDV-UHFFFAOYSA-N 7-chloro-4-[[2-(1,4-diazepane-1-carbonyl)pyridin-4-yl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(Cl)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=NC=1C(=O)N1CCCNCC1 LXESPGUPGCNDDV-UHFFFAOYSA-N 0.000 description 2
- CPRGNIMWMJQBJT-UHFFFAOYSA-N 7-chloro-4-[[3-(1,4-diazepan-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCC[NH2+]CC1 CPRGNIMWMJQBJT-UHFFFAOYSA-N 0.000 description 2
- JOQPDHQMLCLVBV-UHFFFAOYSA-N 7-chloro-4-[[3-(1,4-diazepane-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCCNCC1 JOQPDHQMLCLVBV-UHFFFAOYSA-N 0.000 description 2
- IRKGRWLLSBDZNT-UHFFFAOYSA-N 7-chloro-4-[[3-(2,5-diazabicyclo[2.2.2]octane-2-carbonyl)-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1C(NC2)CCC2N1C(=O)C1=CC(CC=2N3C=C(Cl)C=C3C(=O)NC=2)=CC=C1F IRKGRWLLSBDZNT-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 2
- 229930024421 Adenine Natural products 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 102400000068 Angiostatin Human genes 0.000 description 2
- 108010079709 Angiostatins Proteins 0.000 description 2
- 235000003911 Arachis Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010061666 Autonomic neuropathy Diseases 0.000 description 2
- 102100027161 BRCA2-interacting transcriptional repressor EMSY Human genes 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 206010005949 Bone cancer Diseases 0.000 description 2
- 208000018084 Bone neoplasm Diseases 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ZIZNFLNLSJTBAP-UHFFFAOYSA-N C(N)(OC1=C(C=CC(=C1)CC1=CNC(C=2N1C(=C(C2)Cl)Cl)=O)F)=O Chemical compound C(N)(OC1=C(C=CC(=C1)CC1=CNC(C=2N1C(=C(C2)Cl)Cl)=O)F)=O ZIZNFLNLSJTBAP-UHFFFAOYSA-N 0.000 description 2
- 101710083734 CTP synthase Proteins 0.000 description 2
- 102100039866 CTP synthase 1 Human genes 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 239000012623 DNA damaging agent Substances 0.000 description 2
- 102100035186 DNA excision repair protein ERCC-1 Human genes 0.000 description 2
- 102100034490 DNA repair and recombination protein RAD54B Human genes 0.000 description 2
- 102100034484 DNA repair protein RAD51 homolog 3 Human genes 0.000 description 2
- 102100027830 DNA repair protein XRCC2 Human genes 0.000 description 2
- 102100027829 DNA repair protein XRCC3 Human genes 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 208000002249 Diabetes Complications Diseases 0.000 description 2
- 206010012655 Diabetic complications Diseases 0.000 description 2
- 101000582926 Dictyostelium discoideum Probable serine/threonine-protein kinase PLK Proteins 0.000 description 2
- 102100033996 Double-strand break repair protein MRE11 Human genes 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 101150029113 EMSY gene Proteins 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 102000009095 Fanconi Anemia Complementation Group A protein Human genes 0.000 description 2
- 108010087740 Fanconi Anemia Complementation Group A protein Proteins 0.000 description 2
- 108010022012 Fanconi Anemia Complementation Group F protein Proteins 0.000 description 2
- 102000012216 Fanconi Anemia Complementation Group F protein Human genes 0.000 description 2
- 108010033305 Fanconi Anemia Complementation Group G protein Proteins 0.000 description 2
- 102000007122 Fanconi Anemia Complementation Group G protein Human genes 0.000 description 2
- 208000003790 Foot Ulcer Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 108050007570 GTP-binding protein Rad Proteins 0.000 description 2
- 102100035184 General transcription and DNA repair factor IIH helicase subunit XPD Human genes 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000007821 HATU Substances 0.000 description 2
- 101001057996 Homo sapiens BRCA2-interacting transcriptional repressor EMSY Proteins 0.000 description 2
- 101000876529 Homo sapiens DNA excision repair protein ERCC-1 Proteins 0.000 description 2
- 101000712511 Homo sapiens DNA repair and recombination protein RAD54-like Proteins 0.000 description 2
- 101001132263 Homo sapiens DNA repair and recombination protein RAD54B Proteins 0.000 description 2
- 101000770953 Homo sapiens DNA repair endonuclease XPF Proteins 0.000 description 2
- 101001132271 Homo sapiens DNA repair protein RAD51 homolog 3 Proteins 0.000 description 2
- 101000649306 Homo sapiens DNA repair protein XRCC2 Proteins 0.000 description 2
- 101000650600 Homo sapiens DNA-directed RNA polymerase I subunit RPA2 Proteins 0.000 description 2
- 101000591400 Homo sapiens Double-strand break repair protein MRE11 Proteins 0.000 description 2
- 101000876511 Homo sapiens General transcription and DNA repair factor IIH helicase subunit XPD Proteins 0.000 description 2
- 101000977270 Homo sapiens MMS19 nucleotide excision repair protein homolog Proteins 0.000 description 2
- 101000949825 Homo sapiens Meiotic recombination protein DMC1/LIM15 homolog Proteins 0.000 description 2
- 101001046894 Homo sapiens Protein HID1 Proteins 0.000 description 2
- 101000709305 Homo sapiens Replication protein A 14 kDa subunit Proteins 0.000 description 2
- 101001092206 Homo sapiens Replication protein A 32 kDa subunit Proteins 0.000 description 2
- 101000777277 Homo sapiens Serine/threonine-protein kinase Chk2 Proteins 0.000 description 2
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 2
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 2
- MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 208000031773 Insulin resistance syndrome Diseases 0.000 description 2
- 102000006992 Interferon-alpha Human genes 0.000 description 2
- 108010047761 Interferon-alpha Proteins 0.000 description 2
- 102000013462 Interleukin-12 Human genes 0.000 description 2
- 108010065805 Interleukin-12 Proteins 0.000 description 2
- 208000012659 Joint disease Diseases 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 102100023474 MMS19 nucleotide excision repair protein homolog Human genes 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 208000000172 Medulloblastoma Diseases 0.000 description 2
- 102100035285 Meiotic recombination protein DMC1/LIM15 homolog Human genes 0.000 description 2
- 102000005741 Metalloproteases Human genes 0.000 description 2
- 108010006035 Metalloproteases Proteins 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 101000669895 Methanothermobacter thermautotrophicus (strain ATCC 29096 / DSM 1053 / JCM 10044 / NBRC 100330 / Delta H) Replication factor A Proteins 0.000 description 2
- 102000029749 Microtubule Human genes 0.000 description 2
- 108091022875 Microtubule Proteins 0.000 description 2
- 208000034486 Multi-organ failure Diseases 0.000 description 2
- 208000010718 Multiple Organ Failure Diseases 0.000 description 2
- 208000034578 Multiple myelomas Diseases 0.000 description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 2
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
- BGIRTVPPUIPHIZ-UHFFFAOYSA-N N-[2-[4-[5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-1,4-diazepan-1-yl]ethyl]acetamide Chemical compound C1CN(CCNC(=O)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F BGIRTVPPUIPHIZ-UHFFFAOYSA-N 0.000 description 2
- 101100355599 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) mus-11 gene Proteins 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KMSKQZKKOZQFFG-HSUXVGOQSA-N Pirarubicin Chemical compound O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1CCCCO1 KMSKQZKKOZQFFG-HSUXVGOQSA-N 0.000 description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 2
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
- 229940079156 Proteasome inhibitor Drugs 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 101150006234 RAD52 gene Proteins 0.000 description 2
- 102000053062 Rad52 DNA Repair and Recombination Human genes 0.000 description 2
- 108700031762 Rad52 DNA Repair and Recombination Proteins 0.000 description 2
- 208000012322 Raynaud phenomenon Diseases 0.000 description 2
- 208000001647 Renal Insufficiency Diseases 0.000 description 2
- 102100034372 Replication protein A 14 kDa subunit Human genes 0.000 description 2
- 102100035525 Replication protein A 32 kDa subunit Human genes 0.000 description 2
- 206010038923 Retinopathy Diseases 0.000 description 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- YJDYDFNKCBANTM-QCWCSKBGSA-N SDZ PSC 833 Chemical compound C\C=C\C[C@@H](C)C(=O)[C@@H]1N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](C(C)C)NC1=O YJDYDFNKCBANTM-QCWCSKBGSA-N 0.000 description 2
- 101000770949 Saccharolobus solfataricus (strain ATCC 35092 / DSM 1617 / JCM 11322 / P2) 3'-flap repair endonuclease Xpf Proteins 0.000 description 2
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 2
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- 102100031075 Serine/threonine-protein kinase Chk2 Human genes 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 101710183280 Topoisomerase Proteins 0.000 description 2
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 2
- 102100023931 Transcriptional regulator ATRX Human genes 0.000 description 2
- 229940123468 Transferase inhibitor Drugs 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 102100040247 Tumor necrosis factor Human genes 0.000 description 2
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 2
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 2
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 2
- 208000014070 Vestibular schwannoma Diseases 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 108010074310 X-ray repair cross complementing protein 3 Proteins 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DEKZPGQGALUACN-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyrazine-3-carboxylic acid Chemical compound C1=NC=CN2C(C(=O)O)=NN=C21 DEKZPGQGALUACN-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 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 2
- 208000004064 acoustic neuroma Diseases 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 description 2
- 230000000340 anti-metabolite Effects 0.000 description 2
- 229940125683 antiemetic agent Drugs 0.000 description 2
- 229940100197 antimetabolite Drugs 0.000 description 2
- 239000002256 antimetabolite Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- FZCSTZYAHCUGEM-UHFFFAOYSA-N aspergillomarasmine B Natural products OC(=O)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O FZCSTZYAHCUGEM-UHFFFAOYSA-N 0.000 description 2
- 239000012131 assay buffer Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- BXDQJVDEALOIQW-UHFFFAOYSA-N benzyl 1,4-diazepane-1-carboxylate Chemical compound C1CCNCCN1C(=O)OCC1=CC=CC=C1 BXDQJVDEALOIQW-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229960002092 busulfan Drugs 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001722 carbon compounds Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 229960005243 carmustine Drugs 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 230000000973 chemotherapeutic effect Effects 0.000 description 2
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 2
- 229960004630 chlorambucil Drugs 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 208000037976 chronic inflammation Diseases 0.000 description 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 229960005537 combretastatin A-4 Drugs 0.000 description 2
- HVXBOLULGPECHP-UHFFFAOYSA-N combretastatin A4 Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-UHFFFAOYSA-N 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 229940111134 coxibs Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 229960004397 cyclophosphamide Drugs 0.000 description 2
- 229960000975 daunorubicin Drugs 0.000 description 2
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 229960003957 dexamethasone Drugs 0.000 description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 2
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 description 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 2
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 description 2
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000005972 dihydrochromenyl group Chemical group 0.000 description 2
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 description 2
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 description 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000005782 double-strand break Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 230000002068 genetic effect Effects 0.000 description 2
- 210000004907 gland Anatomy 0.000 description 2
- 229960002989 glutamic acid Drugs 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000003394 haemopoietic effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229940121372 histone deacetylase inhibitor Drugs 0.000 description 2
- 239000004030 hiv protease inhibitor Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- 230000001146 hypoxic effect Effects 0.000 description 2
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 2
- 229960001101 ifosfamide Drugs 0.000 description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- 229940117681 interleukin-12 Drugs 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 208000017169 kidney disease Diseases 0.000 description 2
- 201000006370 kidney failure Diseases 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 201000002818 limb ischemia Diseases 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 229960002247 lomustine Drugs 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 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
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 206010027191 meningioma Diseases 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 210000004688 microtubule Anatomy 0.000 description 2
- 231100000782 microtubule inhibitor Toxicity 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000008600 mitotic progression Effects 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 210000004165 myocardium Anatomy 0.000 description 2
- NUWAEULNPPMFQQ-UHFFFAOYSA-N n-[(2,4-dimethoxyphenyl)methyl]-4-methyl-n-prop-2-ynyl-1h-pyrrole-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1CN(CC#C)C(=O)C1=CC(C)=CN1 NUWAEULNPPMFQQ-UHFFFAOYSA-N 0.000 description 2
- GYAUFAUJSKIJQB-UHFFFAOYSA-N n-[(2,4-dimethoxyphenyl)methyl]-n-prop-2-ynyl-1h-pyrrole-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1CN(CC#C)C(=O)C1=CC=CN1 GYAUFAUJSKIJQB-UHFFFAOYSA-N 0.000 description 2
- IYEMEVZEXZGKFA-UHFFFAOYSA-N n-[(2,4-dimethoxyphenyl)methyl]prop-2-yn-1-amine Chemical compound COC1=CC=C(CNCC#C)C(OC)=C1 IYEMEVZEXZGKFA-UHFFFAOYSA-N 0.000 description 2
- RRUDMAAKCLPVBC-UHFFFAOYSA-N n-[3-(3-cyano-4-fluorophenyl)prop-2-ynyl]-n-[(2,4-dimethoxyphenyl)methyl]-1h-pyrrole-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1CN(C(=O)C=1NC=CC=1)CC#CC1=CC=C(F)C(C#N)=C1 RRUDMAAKCLPVBC-UHFFFAOYSA-N 0.000 description 2
- WJVKYGUNJHLCSV-UHFFFAOYSA-N n-[3-(3-cyano-4-fluorophenyl)prop-2-ynyl]-n-[(2,4-dimethoxyphenyl)methyl]-4-methyl-1h-pyrrole-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1CN(C(=O)C=1NC=C(C)C=1)CC#CC1=CC=C(F)C(C#N)=C1 WJVKYGUNJHLCSV-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 201000001119 neuropathy Diseases 0.000 description 2
- 230000007823 neuropathy Effects 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 2
- 229960001756 oxaliplatin Drugs 0.000 description 2
- 125000005961 oxazepanyl group Chemical group 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- WRUUGTRCQOWXEG-UHFFFAOYSA-N pamidronate Chemical compound NCCC(O)(P(O)(O)=O)P(O)(O)=O WRUUGTRCQOWXEG-UHFFFAOYSA-N 0.000 description 2
- 201000002528 pancreatic cancer Diseases 0.000 description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 229940043138 pentosan polysulfate Drugs 0.000 description 2
- 208000033808 peripheral neuropathy Diseases 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
- 229960001221 pirarubicin Drugs 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000005731 poly ADP ribosylation Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000770 proinflammatory effect Effects 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 2
- 239000003207 proteasome inhibitor Substances 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 108050008067 rad9 Proteins 0.000 description 2
- 102000000611 rad9 Human genes 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 2
- 229960004622 raloxifene Drugs 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229940075993 receptor modulator Drugs 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 2
- VHXNKPBCCMUMSW-FQEVSTJZSA-N rubitecan Chemical compound C1=CC([N+]([O-])=O)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VHXNKPBCCMUMSW-FQEVSTJZSA-N 0.000 description 2
- 229950009213 rubitecan Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 230000036303 septic shock Effects 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 235000011069 sorbitan monooleate Nutrition 0.000 description 2
- 239000001593 sorbitan monooleate Substances 0.000 description 2
- 229940035049 sorbitan monooleate Drugs 0.000 description 2
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 229960001603 tamoxifen Drugs 0.000 description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 2
- 229960003433 thalidomide Drugs 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 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
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 2
- 229960000875 trofosfamide Drugs 0.000 description 2
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 2
- 229960001641 troglitazone Drugs 0.000 description 2
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 241000701161 unidentified adenovirus Species 0.000 description 2
- 102000009816 urokinase plasminogen activator receptor activity proteins Human genes 0.000 description 2
- 108040001269 urokinase plasminogen activator receptor activity proteins Proteins 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 229950010938 valspodar Drugs 0.000 description 2
- 108010082372 valspodar Proteins 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 2
- 229960000237 vorinostat Drugs 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 2
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 description 1
- JKFZMIQMKFWJAY-RQJQXFIZSA-N (1r,3s,5z)-5-[(2e)-2-[(3as,7as)-1-[(2r)-6-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-3a,5,6,7-tetrahydro-3h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C1(/[C@@H]2CC=C([C@]2(CCC1)C)[C@@H](CC#CC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C JKFZMIQMKFWJAY-RQJQXFIZSA-N 0.000 description 1
- JIWYUMAZFCANOG-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 1h-pyrrole-2-carboxylate Chemical compound C=1C=CNC=1C(=O)ON1C(=O)CCC1=O JIWYUMAZFCANOG-UHFFFAOYSA-N 0.000 description 1
- DLMYFMLKORXJPO-FQEVSTJZSA-N (2R)-2-amino-3-[(triphenylmethyl)thio]propanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](N)C(O)=O)C1=CC=CC=C1 DLMYFMLKORXJPO-FQEVSTJZSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- JTBVPIHWMWILJU-MHZLTWQESA-N (2s)-2-(2-acetylanilino)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC(=O)C1=CC=CC=C1N[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 JTBVPIHWMWILJU-MHZLTWQESA-N 0.000 description 1
- VGSJXSLGVQINOL-MHZLTWQESA-N (2s)-2-[4-[2-[(2,4-difluorophenyl)carbamoyl-heptylamino]ethyl]phenoxy]-2-methylbutanoic acid Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CCC1=CC=C(O[C@@](C)(CC)C(O)=O)C=C1 VGSJXSLGVQINOL-MHZLTWQESA-N 0.000 description 1
- ZUQBAQVRAURMCL-DOMZBBRYSA-N (2s)-2-[[4-[2-[(6r)-2-amino-4-oxo-5,6,7,8-tetrahydro-1h-pyrido[2,3-d]pyrimidin-6-yl]ethyl]benzoyl]amino]pentanedioic acid Chemical compound C([C@@H]1CC=2C(=O)N=C(NC=2NC1)N)CC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 ZUQBAQVRAURMCL-DOMZBBRYSA-N 0.000 description 1
- WMUIIGVAWPWQAW-DEOSSOPVSA-N (2s)-2-ethoxy-3-{4-[2-(10h-phenoxazin-10-yl)ethoxy]phenyl}propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2OC2=CC=CC=C21 WMUIIGVAWPWQAW-DEOSSOPVSA-N 0.000 description 1
- YQXRKJHVAUKXRN-NSHDSACASA-N (2s)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC[C@@]1(C)C(O)=O YQXRKJHVAUKXRN-NSHDSACASA-N 0.000 description 1
- MQSMWZHHUGSULF-QNGWXLTQSA-N (2s)-n-benzyl-3-(4-chlorophenyl)-n-(1,5-dipyridin-4-ylpentan-3-yl)-2-[methyl-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]amino]propanamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C(=O)N(C)[C@@H](CC=2C=CC(Cl)=CC=2)C(=O)N(CC=2C=CC=CC=2)C(CCC=2C=CN=CC=2)CCC=2C=CN=CC=2)=C1 MQSMWZHHUGSULF-QNGWXLTQSA-N 0.000 description 1
- PSVUJBVBCOISSP-SPFKKGSWSA-N (2s,3r,4s,5s,6r)-2-bis(2-chloroethylamino)phosphoryloxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OC[C@H]1O[C@@H](OP(=O)(NCCCl)NCCCl)[C@H](O)[C@@H](O)[C@@H]1O PSVUJBVBCOISSP-SPFKKGSWSA-N 0.000 description 1
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
- FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 description 1
- ZKSNZYLCOXUJIR-VOKUKXJJSA-N (5s,5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7-(dimethylamino)-8-hydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)N(C)C)[C@@H]3[C@@H]2C(OC3)=O)=C1 ZKSNZYLCOXUJIR-VOKUKXJJSA-N 0.000 description 1
- DLROLUIVVKTFPW-LVEBQJTPSA-N (5s,5as,8ar,9r)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](NC=3C=CC(=CC=3)[N+]([O-])=O)[C@@H]3[C@@H]2C(OC3)=O)=C1 DLROLUIVVKTFPW-LVEBQJTPSA-N 0.000 description 1
- WTSKMKRYHATLLL-UHFFFAOYSA-N (6-benzoyloxy-3-cyanopyridin-2-yl) 3-[3-(ethoxymethyl)-5-fluoro-2,6-dioxopyrimidine-1-carbonyl]benzoate Chemical compound O=C1N(COCC)C=C(F)C(=O)N1C(=O)C1=CC=CC(C(=O)OC=2C(=CC=C(OC(=O)C=3C=CC=CC=3)N=2)C#N)=C1 WTSKMKRYHATLLL-UHFFFAOYSA-N 0.000 description 1
- BSRQHWFOFMAZRL-BODGVHBXSA-N (7s,9s)-7-[(2r,4s,5s,6s)-5-[(2s,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7h-tetracene-5,12-dione;hydron;chloride Chemical compound Cl.C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@@H](O)C[C@H](O[C@@H]2C3=C(O)C=4C(=O)C5=CC=CC=C5C(=O)C=4C(O)=C3C[C@](O)(C2)C(=O)CO)O[C@H]1C BSRQHWFOFMAZRL-BODGVHBXSA-N 0.000 description 1
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ZGNLFUXWZJGETL-YUSKDDKASA-N (Z)-[(2S)-2-amino-2-carboxyethyl]-hydroxyimino-oxidoazanium Chemical compound N[C@@H](C\[N+]([O-])=N\O)C(O)=O ZGNLFUXWZJGETL-YUSKDDKASA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- BWDQBBCUWLSASG-MDZDMXLPSA-N (e)-n-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1h-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(CCO)CC1=CC=C(\C=C\C(=O)NO)C=C1 BWDQBBCUWLSASG-MDZDMXLPSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 description 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 description 1
- QSNVXCLUVMICBZ-UHFFFAOYSA-N 1,4-diazepane-1-carboxylic acid Chemical compound OC(=O)N1CCCNCC1 QSNVXCLUVMICBZ-UHFFFAOYSA-N 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 description 1
- SZTABURQHHKBND-UHFFFAOYSA-N 1-(1H-imidazol-2-ylmethyl)-1,4-diazepane Chemical compound N=1C=CNC=1CN1CCCNCC1 SZTABURQHHKBND-UHFFFAOYSA-N 0.000 description 1
- VAMFSFIPDOODFH-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NS(=O)(=O)C1=CC=C(OCC2)C2=C1 VAMFSFIPDOODFH-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- SHINCNKTDRJFSG-UHFFFAOYSA-N 1-[1-[5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]piperidin-4-yl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C12=CC=CN=C2NC(=O)N1C(CC1)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F SHINCNKTDRJFSG-UHFFFAOYSA-N 0.000 description 1
- MZNMZWZGUGFQJP-UHFFFAOYSA-N 1-[11-(dodecylamino)-10-hydroxyundecyl]-3,7-dimethylpurine-2,6-dione Chemical compound O=C1N(CCCCCCCCCC(O)CNCCCCCCCCCCCC)C(=O)N(C)C2=C1N(C)C=N2 MZNMZWZGUGFQJP-UHFFFAOYSA-N 0.000 description 1
- IDMPXWWCPGSMAF-UHFFFAOYSA-N 1-[5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorophenyl]-4-methylpiperazine-2,6-dione Chemical compound O=C1CN(C)CC(=O)N1C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F IDMPXWWCPGSMAF-UHFFFAOYSA-N 0.000 description 1
- LUJAKKBYRBQJHS-UHFFFAOYSA-N 1-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorophenyl]-4-methylpiperazin-4-ium-2,6-dione;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O=C1C[NH+](C)CC(=O)N1C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F LUJAKKBYRBQJHS-UHFFFAOYSA-N 0.000 description 1
- RIKWVZGZRYDACA-UHFFFAOYSA-N 1-fluoro-3-isocyanatobenzene Chemical compound FC1=CC=CC(N=C=O)=C1 RIKWVZGZRYDACA-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DDZGQYREBDXECY-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyrazine Chemical group C1=CN=C2C=NNC2=N1 DDZGQYREBDXECY-UHFFFAOYSA-N 0.000 description 1
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical class NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 description 1
- BVTVLEZDVMAWPR-UHFFFAOYSA-N 1h-pyrrolo[2,3-a]acridine Chemical compound C1=CC=CC2=CC3=C(NC=C4)C4=CC=C3N=C21 BVTVLEZDVMAWPR-UHFFFAOYSA-N 0.000 description 1
- ROZCIVXTLACYNY-UHFFFAOYSA-N 2,3,4,5,6-pentafluoro-n-(3-fluoro-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F ROZCIVXTLACYNY-UHFFFAOYSA-N 0.000 description 1
- AUAJGFQDEXTSCT-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.2]octane-2-carboxylic acid Chemical compound C1CC2N(C(=O)O)CC1NC2 AUAJGFQDEXTSCT-UHFFFAOYSA-N 0.000 description 1
- 125000003870 2-(1-piperidinyl)ethoxy group Chemical group [*]OC([H])([H])C([H])([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- XWNJMSJGJFSGRY-UHFFFAOYSA-N 2-(benzylamino)-3,7-dihydropurin-6-one Chemical compound N1C=2N=CNC=2C(=O)N=C1NCC1=CC=CC=C1 XWNJMSJGJFSGRY-UHFFFAOYSA-N 0.000 description 1
- OOHUOYPEBUGEJR-UHFFFAOYSA-N 2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine Chemical compound C1CNCC2=NC(C(F)(F)F)=NC=C21 OOHUOYPEBUGEJR-UHFFFAOYSA-N 0.000 description 1
- WAXINHRGKZWFCJ-UHFFFAOYSA-N 2-(trifluoromethyl)-6,7-dihydro-5h-pyrrolo[3,4-d]pyrimidine Chemical compound FC(F)(F)C1=NC=C2CNCC2=N1 WAXINHRGKZWFCJ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WIQFRYIFXQVNDT-UHFFFAOYSA-N 2-[4-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]piperazin-1-yl]-n,n-dimethyl-2-oxoacetamide Chemical compound C1CN(C(=O)C(=O)N(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F WIQFRYIFXQVNDT-UHFFFAOYSA-N 0.000 description 1
- WHDZIHPUHKKXHG-UHFFFAOYSA-N 2-[4-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]piperazin-1-yl]pyridin-1-ium-3-carbonitrile;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=[NH+]C=CC=C1C#N WHDZIHPUHKKXHG-UHFFFAOYSA-N 0.000 description 1
- RUIWUDJYVYEUJX-UHFFFAOYSA-N 2-[[5,7-dipropyl-3-(trifluoromethyl)-1,2-benzoxazol-6-yl]oxy]-2-methylpropanoic acid Chemical compound CCCC1=C(OC(C)(C)C(O)=O)C(CCC)=CC2=C1ON=C2C(F)(F)F RUIWUDJYVYEUJX-UHFFFAOYSA-N 0.000 description 1
- ORAWNRHPUHILCK-UHFFFAOYSA-N 2-[[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-methylamino]ethyl-methylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=C(F)C(C(=O)N(C)CC[NH2+]C)=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=C1 ORAWNRHPUHILCK-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- RAMAPMJJBMFFEI-UHFFFAOYSA-N 2-iodopyridine-4-carbonitrile Chemical compound IC1=CC(C#N)=CC=N1 RAMAPMJJBMFFEI-UHFFFAOYSA-N 0.000 description 1
- GCGBPPCSOJNFDC-UHFFFAOYSA-N 2-oxoethyl carbamate Chemical compound NC(=O)OCC=O GCGBPPCSOJNFDC-UHFFFAOYSA-N 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- SVMRIWUVQVPFTQ-UHFFFAOYSA-N 2h-pyrrolo[1,2-d][1,2,4]triazin-1-one Chemical class O=C1NN=CN2C=CC=C12 SVMRIWUVQVPFTQ-UHFFFAOYSA-N 0.000 description 1
- FFRFGVHNKJYNOV-DOVUUNBWSA-N 3',4'-Anhydrovinblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C=C(C2)CC)N2CCC2=C1NC1=CC=CC=C21 FFRFGVHNKJYNOV-DOVUUNBWSA-N 0.000 description 1
- QUHVRXKSQHIZNV-UHFFFAOYSA-N 3,3-difluoroazetidine Chemical compound FC1(F)CNC1 QUHVRXKSQHIZNV-UHFFFAOYSA-N 0.000 description 1
- MAMLRMFRYYTAHK-UHFFFAOYSA-N 3,4-dichloro-5-methoxycarbonyl-1h-pyrrole-2-carboxylic acid Chemical compound COC(=O)C=1NC(C(O)=O)=C(Cl)C=1Cl MAMLRMFRYYTAHK-UHFFFAOYSA-N 0.000 description 1
- AQCSCRYRCRORET-UHFFFAOYSA-N 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine;hydrochloride Chemical compound Cl.C1NCCN2C(C(F)(F)F)=NN=C21 AQCSCRYRCRORET-UHFFFAOYSA-N 0.000 description 1
- WUWDLXZGHZSWQZ-UHFFFAOYSA-N 3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one Chemical compound N1C(C)=CC(C)=C1C=C1C2=CC=CC=C2NC1=O WUWDLXZGHZSWQZ-UHFFFAOYSA-N 0.000 description 1
- ZWQBJRSZJUBPNE-UHFFFAOYSA-N 3-[1-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]azetidin-3-yl]pyridine-2-carbonitrile Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CC1C1=CC=CN=C1C#N ZWQBJRSZJUBPNE-UHFFFAOYSA-N 0.000 description 1
- NHFDRBXTEDBWCZ-ZROIWOOFSA-N 3-[2,4-dimethyl-5-[(z)-(2-oxo-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=CC=C3NC\2=O)=C1C NHFDRBXTEDBWCZ-ZROIWOOFSA-N 0.000 description 1
- GSCPDZHWVNUUFI-UHFFFAOYSA-N 3-aminobenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1 GSCPDZHWVNUUFI-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- VHIFIZLIKVIGLC-UHFFFAOYSA-N 3-pyrrolidin-1-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine Chemical compound C1CCCN1C1=NN=C2N1CCNC2 VHIFIZLIKVIGLC-UHFFFAOYSA-N 0.000 description 1
- 239000003185 4 aminobutyric acid B receptor stimulating agent Substances 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- QVESRHVXQZDONP-UHFFFAOYSA-N 4-(2-amino-6,7-dimethoxyquinazolin-4-yl)-2-bromophenol Chemical compound C=12C=C(OC)C(OC)=CC2=NC(N)=NC=1C1=CC=C(O)C(Br)=C1 QVESRHVXQZDONP-UHFFFAOYSA-N 0.000 description 1
- WIYNWLBOSGNXEH-UHFFFAOYSA-N 4-(2-amino-6,7-dimethoxyquinazolin-4-yl)phenol Chemical compound C=12C=C(OC)C(OC)=CC2=NC(N)=NC=1C1=CC=C(O)C=C1 WIYNWLBOSGNXEH-UHFFFAOYSA-N 0.000 description 1
- IYZGMTPUQWNOER-UHFFFAOYSA-N 4-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F IYZGMTPUQWNOER-UHFFFAOYSA-N 0.000 description 1
- FDIOVXDYQPWXIW-UHFFFAOYSA-N 4-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F FDIOVXDYQPWXIW-UHFFFAOYSA-N 0.000 description 1
- OZBUFFXESDBEHG-FXILSDISSA-N 4-[[(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OZBUFFXESDBEHG-FXILSDISSA-N 0.000 description 1
- ZKQOMTAJLSAKRC-UHFFFAOYSA-N 4-[[2-[(2,4-dimethoxyphenyl)methyl]-1-oxopyrrolo[1,2-a]pyrazin-4-yl]methyl]-2-fluorobenzonitrile Chemical compound COC1=CC(OC)=CC=C1CN1C(=O)C2=CC=CN2C(CC=2C=C(F)C(C#N)=CC=2)=C1 ZKQOMTAJLSAKRC-UHFFFAOYSA-N 0.000 description 1
- FKLQJJSBHNWDFJ-UHFFFAOYSA-N 4-[[3-(1,3,4,4a,5,9b-hexahydropyrido[4,3-b]indole-2-carbonyl)-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound N1C2=CC=CC=C2C(C2)C1CCN2C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F FKLQJJSBHNWDFJ-UHFFFAOYSA-N 0.000 description 1
- GJNKGKNWTQHLAU-UHFFFAOYSA-N 4-[[3-(2-aza-8-azoniaspiro[5.5]undecane-2-carbonyl)-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCCC21CCC[NH2+]C2 GJNKGKNWTQHLAU-UHFFFAOYSA-N 0.000 description 1
- PUNCCIJSIGGSQZ-UHFFFAOYSA-N 4-[[3-(3,3-dimethylpiperazine-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CNC(C)(C)CN1C(=O)C1=CC(CC=2N3C=CC=C3C(=O)NC=2)=CC=C1F PUNCCIJSIGGSQZ-UHFFFAOYSA-N 0.000 description 1
- JXHPERCOKNTKOI-UHFFFAOYSA-N 4-[[3-(3-bromo-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl)-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN2C(Br)=NN=C2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F JXHPERCOKNTKOI-UHFFFAOYSA-N 0.000 description 1
- DYJWTCOVYPYXKL-UHFFFAOYSA-N 4-[[3-(4-acetyl-1,4-diazepane-1-carbonyl)-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F DYJWTCOVYPYXKL-UHFFFAOYSA-N 0.000 description 1
- HRUCWUHJVHMCSF-UHFFFAOYSA-N 4-[[3-(4-aminopiperidine-1-carbonyl)-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CC(N)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F HRUCWUHJVHMCSF-UHFFFAOYSA-N 0.000 description 1
- XHURCEULXMTQNM-UHFFFAOYSA-N 4-[[3-(4-benzoylpiperazine-1-carbonyl)-4-fluorophenyl]methyl]-7-chloro-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CC=CC=C1 XHURCEULXMTQNM-UHFFFAOYSA-N 0.000 description 1
- WQMKBBRHKXDKDL-UHFFFAOYSA-N 4-[[3-(4-benzoylpiperidine-1-carbonyl)-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1C(=O)C1=CC=CC=C1 WQMKBBRHKXDKDL-UHFFFAOYSA-N 0.000 description 1
- DMFRTIQADWETQN-UHFFFAOYSA-N 4-[[3-(4-butan-2-yl-1,4-diazepane-1-carbonyl)-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(C)CC)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F DMFRTIQADWETQN-UHFFFAOYSA-N 0.000 description 1
- WXPYTMJOYLOZQS-UHFFFAOYSA-N 4-[[3-(4-butylpiperazine-1-carbonyl)-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CCCC)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F WXPYTMJOYLOZQS-UHFFFAOYSA-N 0.000 description 1
- SOKYPSXMFSKSKW-INIZCTEOSA-N 4-[[3-[(8aS)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine-2-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN2CCC[C@H]2CN1C(=O)C1=CC(CC=2N3C=CC=C3C(=O)NC=2)=CC=C1F SOKYPSXMFSKSKW-INIZCTEOSA-N 0.000 description 1
- CERSGWVBZYNXNG-UHFFFAOYSA-N 4-[[3-[3-(1H-benzimidazol-2-yl)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC=C2NC(C3CCCN(C3)C(=O)C3=CC(CC=4N5C(Cl)=C(Cl)C=C5C(=O)NC=4)=CC=C3F)=NC2=C1 CERSGWVBZYNXNG-UHFFFAOYSA-N 0.000 description 1
- QXQHXIIXDNVUOQ-UHFFFAOYSA-N 4-[[3-[3-(aminomethyl)azetidine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1C(CN)CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F QXQHXIIXDNVUOQ-UHFFFAOYSA-N 0.000 description 1
- GIURQTKCJFHWMP-UHFFFAOYSA-N 4-[[3-[3-(aminomethyl)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1C(CN)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F GIURQTKCJFHWMP-UHFFFAOYSA-N 0.000 description 1
- GWHKYURYAVQJBY-UHFFFAOYSA-N 4-[[3-[4-(1,3-benzothiazol-2-yl)-1,4-diazepane-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1=NC2=CC=CC=C2S1 GWHKYURYAVQJBY-UHFFFAOYSA-N 0.000 description 1
- HHVMXAMPJPRBOA-UHFFFAOYSA-N 4-[[3-[4-(1-azabicyclo[2.2.2]octan-3-yl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1N(CC2)CCC2C1N(CC1)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F HHVMXAMPJPRBOA-UHFFFAOYSA-N 0.000 description 1
- VQZKBOYDFJEZNC-UHFFFAOYSA-N 4-[[3-[4-(1H-benzimidazol-2-yl)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC=C2NC(C3CCN(CC3)C(=O)C3=CC(CC=4N5C(Cl)=C(Cl)C=C5C(=O)NC=4)=CC=C3F)=NC2=C1 VQZKBOYDFJEZNC-UHFFFAOYSA-N 0.000 description 1
- RXANGDVFVPYSOX-UHFFFAOYSA-N 4-[[3-[4-(2,3-dihydro-1H-inden-2-yl)-1,4-diazepane-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=CC=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1CC2=CC=CC=C2C1 RXANGDVFVPYSOX-UHFFFAOYSA-N 0.000 description 1
- BQRPLGMBLZDJBU-UHFFFAOYSA-N 4-[[3-[4-(2-amino-2-methylpropyl)-1,4-diazepane-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CC(C)(N)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F BQRPLGMBLZDJBU-UHFFFAOYSA-N 0.000 description 1
- BYOIUGJXULOTTL-UHFFFAOYSA-N 4-[[3-[4-(4-acetylphenyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 BYOIUGJXULOTTL-UHFFFAOYSA-N 0.000 description 1
- NXRHQLRWGIBVDV-UHFFFAOYSA-N 4-[[3-[4-(azepan-1-ium-1-yl)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1[NH+]1CCCCCC1 NXRHQLRWGIBVDV-UHFFFAOYSA-N 0.000 description 1
- NLWAKKCJWJKESX-UHFFFAOYSA-N 4-[[3-[4-(azetidin-1-ium-1-yl)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1[NH+]1CCC1 NLWAKKCJWJKESX-UHFFFAOYSA-N 0.000 description 1
- FIARVTUNWAWXGW-UHFFFAOYSA-N 4-[[3-[4-(azetidin-1-ium-3-carbonyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)C1C[NH2+]C1 FIARVTUNWAWXGW-UHFFFAOYSA-N 0.000 description 1
- MOXHPOZNDYUEKR-UHFFFAOYSA-N 4-[[3-[4-(azetidin-3-yl)-1,4-diazepane-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1CNC1 MOXHPOZNDYUEKR-UHFFFAOYSA-N 0.000 description 1
- ASSXTMNEJYFCGH-SFHVURJKSA-N 4-[[3-[4-[(2s)-azetidine-2-carbonyl]piperazine-1-carbonyl]-4-fluorophenyl]methyl]-6,7-dichloro-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)[C@@H]1CCN1 ASSXTMNEJYFCGH-SFHVURJKSA-N 0.000 description 1
- QBQLYIISSRXYKL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O QBQLYIISSRXYKL-UHFFFAOYSA-N 0.000 description 1
- JVWMGVABXGYRFD-UHFFFAOYSA-N 4-[[4-fluoro-3-(4-methyl-1,4-diazepane-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C)CCCN1C(=O)C1=CC(CC=2N3C=CC=C3C(=O)NC=2)=CC=C1F JVWMGVABXGYRFD-UHFFFAOYSA-N 0.000 description 1
- JZNUTZUMLNEMMN-UHFFFAOYSA-N 4-[[4-fluoro-3-(4-pyridin-2-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=CC=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=CC=CC=N1 JZNUTZUMLNEMMN-UHFFFAOYSA-N 0.000 description 1
- BHIWOJYVVONDKM-UHFFFAOYSA-N 4-[[4-fluoro-3-(piperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=CC=C3C(=O)NC=2)C=C1C(=O)N1CCNCC1 BHIWOJYVVONDKM-UHFFFAOYSA-N 0.000 description 1
- YJJCOLVTMCBMRQ-UHFFFAOYSA-N 4-[[4-fluoro-3-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN2C(C(F)(F)F)=NN=C2CN1C(=O)C1=CC(CC=2N3C=CC=C3C(=O)NC=2)=CC=C1F YJJCOLVTMCBMRQ-UHFFFAOYSA-N 0.000 description 1
- QBMDYTWLLPHYBL-UHFFFAOYSA-N 4-[[4-fluoro-3-[4-(2-hydroxyethyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CCO)CCN1C(=O)C1=CC(CC=2N3C=CC=C3C(=O)NC=2)=CC=C1F QBMDYTWLLPHYBL-UHFFFAOYSA-N 0.000 description 1
- YLDCUKJMEKGGFI-QCSRICIXSA-N 4-acetamidobenzoic acid;9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one;1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C.CC(O)CN(C)C.CC(O)CN(C)C.CC(=O)NC1=CC=C(C(O)=O)C=C1.CC(=O)NC1=CC=C(C(O)=O)C=C1.CC(=O)NC1=CC=C(C(O)=O)C=C1.O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(NC=NC2=O)=C2N=C1 YLDCUKJMEKGGFI-QCSRICIXSA-N 0.000 description 1
- IUQFZBPPHOHNHQ-JQCXWYLXSA-N 4-amino-1-[(2r,3r,4s,5s)-3,4-dihydroxy-5-(1-hydroxyethenyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](C(O)=C)O1 IUQFZBPPHOHNHQ-JQCXWYLXSA-N 0.000 description 1
- TVZGACDUOSZQKY-LBPRGKRZSA-N 4-aminofolic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 TVZGACDUOSZQKY-LBPRGKRZSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- RNQAFQCXISTQJB-UHFFFAOYSA-N 4-iodopyridine-2-carboxylic acid;hydroiodide Chemical compound [I-].OC(=O)C1=CC(I)=CC=[NH+]1 RNQAFQCXISTQJB-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- FGQJBZHMORPBRR-UHFFFAOYSA-N 4-methylmorpholine-2,6-dione Chemical compound CN1CC(=O)OC(=O)C1 FGQJBZHMORPBRR-UHFFFAOYSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
- NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 description 1
- LGZKGOGODCLQHG-CYBMUJFWSA-N 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C[C@@H](O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-CYBMUJFWSA-N 0.000 description 1
- JLOKOYQIXCWTRN-UHFFFAOYSA-N 5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluoro-N-[1-(pyridin-4-ylmethyl)piperidin-4-yl]benzamide Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)NC(CC1)CCN1CC1=CC=NC=C1 JLOKOYQIXCWTRN-UHFFFAOYSA-N 0.000 description 1
- UMAXVJBKADAOAG-UHFFFAOYSA-N 5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluoro-N-[2-(4-methyl-1,4-diazepan-1-yl)ethyl]benzamide Chemical compound C1CN(C)CCCN1CCNC(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F UMAXVJBKADAOAG-UHFFFAOYSA-N 0.000 description 1
- FTBBBRJQQDCJRB-RTBURBONSA-N 5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluoro-N-methyl-N-[(1R,2R)-2-(methylamino)cyclohexyl]benzamide Chemical compound CN[C@@H]1CCCC[C@H]1N(C)C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F FTBBBRJQQDCJRB-RTBURBONSA-N 0.000 description 1
- WDGSEZGLZCSFMM-UHFFFAOYSA-N 5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluoro-N-methyl-N-[3-(methylamino)propyl]benzamide Chemical compound C1=C(F)C(C(=O)N(C)CCCNC)=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=C1 WDGSEZGLZCSFMM-UHFFFAOYSA-N 0.000 description 1
- RNCBZHZTNFNXRA-UHFFFAOYSA-N 5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluoro-N-piperidin-4-ylbenzamide Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)NC1CCNCC1 RNCBZHZTNFNXRA-UHFFFAOYSA-N 0.000 description 1
- NXMZPPOQYGSGDR-UHFFFAOYSA-N 5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluoro-n-(1-methylpiperidin-1-ium-4-yl)benzamide;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C[NH+](C)CCC1NC(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F NXMZPPOQYGSGDR-UHFFFAOYSA-N 0.000 description 1
- FLJOAVIGXAEZNJ-UHFFFAOYSA-N 5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzamide Chemical compound C1=C(F)C(C(=O)N)=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=C1 FLJOAVIGXAEZNJ-UHFFFAOYSA-N 0.000 description 1
- OBRKYXFJWQXBTM-UHFFFAOYSA-N 5-[(7,8-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(CC=2N3C=C(Cl)C(Cl)=C3C(=O)NC=2)=C1 OBRKYXFJWQXBTM-UHFFFAOYSA-N 0.000 description 1
- GNWFFRUVNPGIFY-UHFFFAOYSA-N 5-[1-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]azetidin-3-yl]pyridine-2-carbonitrile Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CC1C1=CC=C(C#N)N=C1 GNWFFRUVNPGIFY-UHFFFAOYSA-N 0.000 description 1
- IETKPTYAGKZLKY-UHFFFAOYSA-N 5-[[4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2C(=O)N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O IETKPTYAGKZLKY-UHFFFAOYSA-N 0.000 description 1
- 239000002677 5-alpha reductase inhibitor Substances 0.000 description 1
- XAUDJQYHKZQPEU-KVQBGUIXSA-N 5-aza-2'-deoxycytidine Chemical compound O=C1N=C(N)N=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XAUDJQYHKZQPEU-KVQBGUIXSA-N 0.000 description 1
- WZXKBPYJTFTQAL-UHFFFAOYSA-N 5-methyl-n-[2-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C(=CC=CC=2)C(F)(F)F)=C1C WZXKBPYJTFTQAL-UHFFFAOYSA-N 0.000 description 1
- GBOQUHPYCRYKGV-UHFFFAOYSA-N 5-nitro-2-(2-pyrrolidin-1-ylethyl)benzo[de]isoquinoline-1,3-dione Chemical compound O=C1C(C=23)=CC=CC3=CC([N+](=O)[O-])=CC=2C(=O)N1CCN1CCCC1 GBOQUHPYCRYKGV-UHFFFAOYSA-N 0.000 description 1
- GPIBUHIRGWDJRU-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(1,4-diazepane-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCCNCC1 GPIBUHIRGWDJRU-UHFFFAOYSA-N 0.000 description 1
- JVAQCWQFAYIGHQ-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(1,7-diazaspiro[3.5]nonane-7-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC21CCN2 JVAQCWQFAYIGHQ-UHFFFAOYSA-N 0.000 description 1
- HATHVQLHSBBXIA-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(1,8-diazaspiro[4.5]decane-8-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC21CCCN2 HATHVQLHSBBXIA-UHFFFAOYSA-N 0.000 description 1
- SNLNDEXRVZSRLX-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(1,9-diazaspiro[5.5]undecane-9-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC21CCCCN2 SNLNDEXRVZSRLX-UHFFFAOYSA-N 0.000 description 1
- GZLYHNMZYHQNKP-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(2,5-diazabicyclo[2.2.2]octane-2-carbonyl)-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1C(NC2)CCC2N1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F GZLYHNMZYHQNKP-UHFFFAOYSA-N 0.000 description 1
- ZMEDCZTWTFWUQL-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(2,6-diazaspiro[3.3]heptane-2-carbonyl)-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CC21CNC2 ZMEDCZTWTFWUQL-UHFFFAOYSA-N 0.000 description 1
- AAXAGRYHVBCAIT-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(2,8-diazaspiro[3.5]nonane-2-carbonyl)-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CC21CCCNC2 AAXAGRYHVBCAIT-UHFFFAOYSA-N 0.000 description 1
- ISMWYVJCMHQSJK-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(2,9-diazaspiro[4.5]decane-2-carbonyl)-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCC21CCCNC2 ISMWYVJCMHQSJK-UHFFFAOYSA-N 0.000 description 1
- RXWMOKJLXSQKFY-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(3,4-dihydro-1h-2,6-naphthyridin-6-ium-2-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CC2=C[NH+]=CC=C2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F RXWMOKJLXSQKFY-UHFFFAOYSA-N 0.000 description 1
- QZXAIAKHEWLNLO-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(3,4-dihydro-1h-2,7-naphthyridin-7-ium-2-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CC2=CC=[NH+]C=C2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F QZXAIAKHEWLNLO-UHFFFAOYSA-N 0.000 description 1
- XPLNEZLHJNMESU-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(3,4-dihydro-1h-isoquinoline-2-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CC2=CC=CC=C2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F XPLNEZLHJNMESU-UHFFFAOYSA-N 0.000 description 1
- DENVHUQERJNKTP-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(3,9-diazabicyclo[4.2.1]nonane-9-carbonyl)-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CNCC2CCC1N2C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F DENVHUQERJNKTP-UHFFFAOYSA-N 0.000 description 1
- ZMRXXRYJUCUMOE-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(4,9-diazabicyclo[4.2.1]nonane-4-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CC(N2)CCC2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F ZMRXXRYJUCUMOE-UHFFFAOYSA-N 0.000 description 1
- ZUKBGLCCKRTMPF-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(4-cyclohexylpiperazine-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1CCCCC1 ZUKBGLCCKRTMPF-UHFFFAOYSA-N 0.000 description 1
- SREWHHVVFRYZQK-UHFFFAOYSA-N 6,7-dichloro-4-[[3-(6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN2C=NN=C2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F SREWHHVVFRYZQK-UHFFFAOYSA-N 0.000 description 1
- IXPFCEXRUQAOHQ-OLZOCXBDSA-N 6,7-dichloro-4-[[3-[(1r,5s)-3,6-diazabicyclo[3.2.1]octane-3-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound N1C(=O)C2=CC(Cl)=C(Cl)N2C(CC=2C=C(C(=CC=2)F)C(=O)N2C[C@@]3([H])NC[C@@](C3)(C2)[H])=C1 IXPFCEXRUQAOHQ-OLZOCXBDSA-N 0.000 description 1
- IXPFCEXRUQAOHQ-QWHCGFSZSA-N 6,7-dichloro-4-[[3-[(1s,5r)-3,6-diazabicyclo[3.2.1]octane-3-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound N1C(=O)C2=CC(Cl)=C(Cl)N2C(CC=2C=C(C(=CC=2)F)C(=O)N2C[C@]3([H])NC[C@](C3)(C2)[H])=C1 IXPFCEXRUQAOHQ-QWHCGFSZSA-N 0.000 description 1
- IAQLOMOAEDDBCN-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[3-[(3,3-difluoroazetidin-1-ium-1-yl)methyl]azetidine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CC1C[NH+]1CC(F)(F)C1 IAQLOMOAEDDBCN-UHFFFAOYSA-N 0.000 description 1
- LTJSIAXJABQWEC-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[3-[(dimethylamino)methyl]azetidine-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1C(CN(C)C)CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F LTJSIAXJABQWEC-UHFFFAOYSA-N 0.000 description 1
- RDCKXWGQXCPZRS-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[3-[(dimethylamino)methyl]piperidine-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1C(CN(C)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F RDCKXWGQXCPZRS-UHFFFAOYSA-N 0.000 description 1
- QMDXEGLZYLNDQJ-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[3-[2-(ethylamino)propyl]azetidine-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1C(CC(C)NCC)CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F QMDXEGLZYLNDQJ-UHFFFAOYSA-N 0.000 description 1
- XYLHCVQXXSVQNF-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(3,3-difluoropyrrolidin-1-yl)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1N1CCC(F)(F)C1 XYLHCVQXXSVQNF-UHFFFAOYSA-N 0.000 description 1
- RRZCPGGADAYSFO-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(3,6-dimethylpyrazin-2-yl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound CC1=CN=C(C)C(N2CCN(CC2)C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)=N1 RRZCPGGADAYSFO-UHFFFAOYSA-N 0.000 description 1
- NYXBOZXGSIVHDU-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(3-chloropyridin-1-ium-2-yl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=[NH+]C=CC=C1Cl NYXBOZXGSIVHDU-UHFFFAOYSA-N 0.000 description 1
- RCZCYOJPEPQHLX-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(4,6-dimethylpyrimidin-2-yl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound CC1=CC(C)=NC(N2CCN(CC2)C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)=N1 RCZCYOJPEPQHLX-UHFFFAOYSA-N 0.000 description 1
- GRQOIXPHBLALBZ-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(5-chloropyridin-1-ium-2-yl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=CC=C(Cl)C=[NH+]1 GRQOIXPHBLALBZ-UHFFFAOYSA-N 0.000 description 1
- RWGKTDIVOONWAN-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(cyclopentanecarbonyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)C1CCCC1 RWGKTDIVOONWAN-UHFFFAOYSA-N 0.000 description 1
- HCAOOPPQWIGYNP-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(diethylamino)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CC(N(CC)CC)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F HCAOOPPQWIGYNP-UHFFFAOYSA-N 0.000 description 1
- LGYROJGFXLLJDY-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-(dimethylamino)piperidine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CC(N(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F LGYROJGFXLLJDY-UHFFFAOYSA-N 0.000 description 1
- UUIVUZRXVIOOIP-LJQANCHMSA-N 6,7-dichloro-4-[[3-[4-[(2r)-2-(dimethylamino)-3,3,3-trifluoropropanoyl]piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)[C@@H](N(C)C)C(F)(F)F)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F UUIVUZRXVIOOIP-LJQANCHMSA-N 0.000 description 1
- HZVNXUDWCBCABW-PMACEKPBSA-N 6,7-dichloro-4-[[3-[4-[(3S,4S)-3,4-difluoropyrrolidin-1-yl]piperidine-1-carbonyl]-4-fluorophenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1[C@H](F)[C@@H](F)CN1C1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 HZVNXUDWCBCABW-PMACEKPBSA-N 0.000 description 1
- KOXUSQYCBSKEKW-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-[2-(dimethylamino)-2-methylpropanoyl]piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C(C)(C)N(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F KOXUSQYCBSKEKW-UHFFFAOYSA-N 0.000 description 1
- JNRNEEZKJZFVLI-UHFFFAOYSA-N 6,7-dichloro-4-[[3-[4-[2-(dimethylamino)ethyl]piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CCN(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F JNRNEEZKJZFVLI-UHFFFAOYSA-N 0.000 description 1
- PHRMNHROYGPNGT-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(1,4,7-triazonane-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCNCCNCC1 PHRMNHROYGPNGT-UHFFFAOYSA-N 0.000 description 1
- ZPOUEUGBLZCSKI-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(1-methyl-1,7-diazaspiro[3.5]nonane-7-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound CN1CCC11CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 ZPOUEUGBLZCSKI-UHFFFAOYSA-N 0.000 description 1
- BAQVPMZKHVXBKJ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(1-methyl-8-aza-1-azoniaspiro[4.5]decane-8-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C[NH+]1CCCC11CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 BAQVPMZKHVXBKJ-UHFFFAOYSA-N 0.000 description 1
- YAVVEFNVRAGKSS-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(1-methyl-9-aza-1-azoniaspiro[5.5]undecane-9-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C[NH+]1CCCCC11CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 YAVVEFNVRAGKSS-UHFFFAOYSA-N 0.000 description 1
- OAAQSYLIVPQQKS-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(3-phenyl-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCN2C1=NN=C2C1=CC=CC=C1 OAAQSYLIVPQQKS-UHFFFAOYSA-N 0.000 description 1
- IBLUXRMBIUTXRD-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(3-phenyl-6,8-dihydro-5H-imidazo[1,2-a]pyrazine-7-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCN2C1=NC=C2C1=CC=CC=C1 IBLUXRMBIUTXRD-UHFFFAOYSA-N 0.000 description 1
- MVOIZCRRJUDKIQ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-hydroxy-4-phenylpiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCC1(O)C1=CC=CC=C1 MVOIZCRRJUDKIQ-UHFFFAOYSA-N 0.000 description 1
- GLNVEPGMQJIWLI-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-hydroxy-4-pyridin-1-ium-3-ylpiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCC1(O)C1=CC=C[NH+]=C1 GLNVEPGMQJIWLI-UHFFFAOYSA-N 0.000 description 1
- ITEMDYAQDJARFU-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-hydroxypiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CC(O)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F ITEMDYAQDJARFU-UHFFFAOYSA-N 0.000 description 1
- CGDKRRCSRTZBRR-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-isoquinolin-1-ylpiperazine-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC=C2C(N3CCN(CC3)C(=O)C3=CC(CC=4N5C(Cl)=C(Cl)C=C5C(=O)NC=4)=CC=C3F)=NC=CC2=C1 CGDKRRCSRTZBRR-UHFFFAOYSA-N 0.000 description 1
- JKEBRBIRLXIQRZ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-isoquinolin-3-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC=C2C=NC(N3CCN(CC3)C(=O)C3=CC(CC=4N5C(Cl)=C(Cl)C=C5C(=O)NC=4)=CC=C3F)=CC2=C1 JKEBRBIRLXIQRZ-UHFFFAOYSA-N 0.000 description 1
- XWOJXDKXEJJHCO-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-methyl-1,4-diazepane-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F XWOJXDKXEJJHCO-UHFFFAOYSA-N 0.000 description 1
- GLSRWZDSRTTXKW-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-morpholin-4-ylpiperidine-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1N1CCOCC1 GLSRWZDSRTTXKW-UHFFFAOYSA-N 0.000 description 1
- OZRGZRYNOMCUNN-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-oxopiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCC(=O)CC1 OZRGZRYNOMCUNN-UHFFFAOYSA-N 0.000 description 1
- BLIQLWZZSVGXJW-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-pentan-3-yl-1,4-diazepane-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(CC)CC)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F BLIQLWZZSVGXJW-UHFFFAOYSA-N 0.000 description 1
- VZNOKESWFDLQTF-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-piperidin-1-ium-4-ylpiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1C1CC[NH2+]CC1 VZNOKESWFDLQTF-UHFFFAOYSA-N 0.000 description 1
- GQNBBATVZRYMCA-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-piperidin-1-ylpiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1N1CCCCC1 GQNBBATVZRYMCA-UHFFFAOYSA-N 0.000 description 1
- BIIBPIGTLMBCDW-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-propan-2-ylpiperazine-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F BIIBPIGTLMBCDW-UHFFFAOYSA-N 0.000 description 1
- RDVMQXDXBHRJQY-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-propyl-1,4-diazepane-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CCC)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F RDVMQXDXBHRJQY-UHFFFAOYSA-N 0.000 description 1
- MEJICRUFOHWXRW-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-pyridin-1-ium-2-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=CC=CC=[NH+]1 MEJICRUFOHWXRW-UHFFFAOYSA-N 0.000 description 1
- HSKARLJPMBVLAG-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-pyridin-1-ium-3-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=CC=C[NH+]=C1 HSKARLJPMBVLAG-UHFFFAOYSA-N 0.000 description 1
- MJOSMYFERFGVBB-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-pyridin-1-ium-4-ylpiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1C1=CC=[NH+]C=C1 MJOSMYFERFGVBB-UHFFFAOYSA-N 0.000 description 1
- GSIVBUUBEYUCHS-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-pyrimidin-2-yl-1,4-diazepane-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1=NC=CC=N1 GSIVBUUBEYUCHS-UHFFFAOYSA-N 0.000 description 1
- CFGURPLVDZLPKX-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-pyrimidin-2-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=NC=CC=N1 CFGURPLVDZLPKX-UHFFFAOYSA-N 0.000 description 1
- KMLGMISLCMRTRU-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-pyrrolidin-1-ium-1-ylpiperidine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1[NH+]1CCCC1 KMLGMISLCMRTRU-UHFFFAOYSA-N 0.000 description 1
- BGCVPVYSYBYSLA-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-quinazolin-2-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC=CC2=NC(N3CCN(CC3)C(=O)C3=CC(CC=4N5C(Cl)=C(Cl)C=C5C(=O)NC=4)=CC=C3F)=NC=C21 BGCVPVYSYBYSLA-UHFFFAOYSA-N 0.000 description 1
- RYGUYLPUSPBYMI-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-quinazolin-4-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC=C2C(N3CCN(CC3)C(=O)C3=CC(CC=4N5C(Cl)=C(Cl)C=C5C(=O)NC=4)=CC=C3F)=NC=NC2=C1 RYGUYLPUSPBYMI-UHFFFAOYSA-N 0.000 description 1
- SZEUKZMBMXXADZ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(4-quinolin-1-ium-2-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC=CC2=[NH+]C(N3CCN(CC3)C(=O)C3=CC(CC=4N5C(Cl)=C(Cl)C=C5C(=O)NC=4)=CC=C3F)=CC=C21 SZEUKZMBMXXADZ-UHFFFAOYSA-N 0.000 description 1
- WNINAKNSNRWKGQ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(5-methyl-2,5-diazabicyclo[2.2.2]octane-2-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound N1C(=O)C2=CC(Cl)=C(Cl)N2C(CC=2C=C(C(=CC=2)F)C(=O)N2CC3CCC2CN3C)=C1 WNINAKNSNRWKGQ-UHFFFAOYSA-N 0.000 description 1
- MYAPOHCEHNQSGC-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(8-methyl-2,8-diazaspiro[3.5]nonane-2-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1N(C)CCCC11CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)C1 MYAPOHCEHNQSGC-UHFFFAOYSA-N 0.000 description 1
- PQLUIAUWDHNAFN-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-(spiro[8-azabicyclo[3.2.1]octane-3,3'-pyrrolidine]-1'-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1C(N2)CCC2CC1(C1)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F PQLUIAUWDHNAFN-UHFFFAOYSA-N 0.000 description 1
- RSYOIWPAVNXWMH-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[3-(4-methylpiperazine-1-carbonyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C)CCN1C(=O)C1=NN=C2N1CCN(C(=O)C=1C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=1)F)C2 RSYOIWPAVNXWMH-UHFFFAOYSA-N 0.000 description 1
- JJHBENYVEMJFMX-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[3-(morpholin-4-ylmethyl)piperidine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCCC1CN1CCOCC1 JJHBENYVEMJFMX-UHFFFAOYSA-N 0.000 description 1
- CBVMRXFBELXVQW-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[3-(piperidin-1-ium-1-ylmethyl)azetidine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CC1C[NH+]1CCCCC1 CBVMRXFBELXVQW-UHFFFAOYSA-N 0.000 description 1
- NJEOKIYKNGXUSI-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[3-(pyrrolidin-1-ium-1-ylmethyl)azetidine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CC1C[NH+]1CCCC1 NJEOKIYKNGXUSI-UHFFFAOYSA-N 0.000 description 1
- DXVINJHVFQBUHM-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[3-(pyrrolidine-1-carbonyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCN2C1=NN=C2C(=O)N1CCCC1 DXVINJHVFQBUHM-UHFFFAOYSA-N 0.000 description 1
- AKQKWKIHUPZPRU-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN2C(C(F)(F)F)=NN=C2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F AKQKWKIHUPZPRU-UHFFFAOYSA-N 0.000 description 1
- NNUPXPCCWADETG-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[3-[4-(trifluoromethyl)phenyl]imino-2,5,6,7,8,8a-hexahydro-[1,2,4]triazolo[4,3-a]pyrazine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound O=C(C(C=C(CC(N(C1=C2)C(Cl)=C2Cl)=CNC1=O)C=C1)=C1F)N1N=C(NC2=CC=C(C(F)(F)F)C=C2)N2C1CNCC2 NNUPXPCCWADETG-UHFFFAOYSA-N 0.000 description 1
- JYRBKFVKDQMUPH-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1,3-oxazol-2-ylmethyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1CC1=NC=CO1 JYRBKFVKDQMUPH-UHFFFAOYSA-N 0.000 description 1
- YHNAWQNCJXLBOW-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1,3-oxazol-4-ylmethyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1CC1=COC=N1 YHNAWQNCJXLBOW-UHFFFAOYSA-N 0.000 description 1
- VTHBBDFEQGVMBP-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1-fluoropropan-2-yl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(CF)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F VTHBBDFEQGVMBP-UHFFFAOYSA-N 0.000 description 1
- WEOVLCBJBKWBQZ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1-hydroxycyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCN1C(=O)C1(O)CC1 WEOVLCBJBKWBQZ-UHFFFAOYSA-N 0.000 description 1
- DXWOTPHRCCRHCZ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1-hydroxypropan-2-yl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(CO)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F DXWOTPHRCCRHCZ-UHFFFAOYSA-N 0.000 description 1
- NETVOCJLLMESOO-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1H-imidazol-5-ylmethyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1CC1=CN=CN1 NETVOCJLLMESOO-UHFFFAOYSA-N 0.000 description 1
- LRNBXYBGNKHKRG-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1H-pyrrol-3-ylmethyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1CC=1C=CNC=1 LRNBXYBGNKHKRG-UHFFFAOYSA-N 0.000 description 1
- ZVQLSMLGABVUNQ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1h-1,2,4-triazol-4-ium-4-yl)piperidine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1N1C=N[NH+]=C1 ZVQLSMLGABVUNQ-UHFFFAOYSA-N 0.000 description 1
- PFMUUSIECIASRE-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(1h-imidazole-2-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=NC=CN1 PFMUUSIECIASRE-UHFFFAOYSA-N 0.000 description 1
- GRYINJIYVKKKEO-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2,2,2-trifluoroacetyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCN(C(=O)C(F)(F)F)CC1 GRYINJIYVKKKEO-UHFFFAOYSA-N 0.000 description 1
- SYQZLSBUCQPQDB-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-fluorophenyl)piperazin-4-ium-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=CC=C1[NH+]1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 SYQZLSBUCQPQDB-UHFFFAOYSA-N 0.000 description 1
- FBBAHHVHLABGEB-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-hydroxy-2-methylpropanoyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F FBBAHHVHLABGEB-UHFFFAOYSA-N 0.000 description 1
- TZHOESILILVBKD-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-hydroxy-2-phenylacetyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCN1C(=O)C(O)C1=CC=CC=C1 TZHOESILILVBKD-UHFFFAOYSA-N 0.000 description 1
- RORSOTCMIOOSCW-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-hydroxy-3-methylbutanoyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C(O)C(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F RORSOTCMIOOSCW-UHFFFAOYSA-N 0.000 description 1
- WGHVAZJPXZBOAP-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-hydroxyethyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CCO)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F WGHVAZJPXZBOAP-UHFFFAOYSA-N 0.000 description 1
- LLFUKWDXHPJYMT-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-hydroxyethyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CCO)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F LLFUKWDXHPJYMT-UHFFFAOYSA-N 0.000 description 1
- YPSVPLAOXRAPEG-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-methylazetidine-2-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCN1C(=O)C1(C)CCN1 YPSVPLAOXRAPEG-UHFFFAOYSA-N 0.000 description 1
- LHMGGULLIKNPKX-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-methylpropyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(CC(C)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F LHMGGULLIKNPKX-UHFFFAOYSA-N 0.000 description 1
- HTYIZGXVKXBMGX-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-methylpropyl)piperazin-4-ium-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1C[NH+](CC(C)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F HTYIZGXVKXBMGX-UHFFFAOYSA-N 0.000 description 1
- VRJSEZGHEKHAHS-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-methylpyrrolidine-2-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCN1C(=O)C1(C)CCCN1 VRJSEZGHEKHAHS-UHFFFAOYSA-N 0.000 description 1
- SYWNNXFOFJCQRV-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-morpholin-4-yl-2-oxoethyl)piperazin-4-ium-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CC[NH+]1CC(=O)N1CCOCC1 SYWNNXFOFJCQRV-UHFFFAOYSA-N 0.000 description 1
- UYYFAHHRBCQETF-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2-morpholin-4-ylpropanoyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCN1C(=O)C(C)N1CCOCC1 UYYFAHHRBCQETF-UHFFFAOYSA-N 0.000 description 1
- NXTYINIPTNGIGM-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(2H-triazol-4-ylmethyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1CC=1C=NNN=1 NXTYINIPTNGIGM-UHFFFAOYSA-N 0.000 description 1
- CZOQVYSTGOLQSO-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(3,3,3-trifluoro-2-hydroxypropanoyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C(O)C(F)(F)F)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F CZOQVYSTGOLQSO-UHFFFAOYSA-N 0.000 description 1
- BBCQMVCWTWUPKO-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(3-fluorobenzoyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=CC(C(=O)N2CCN(CC2)C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)=C1 BBCQMVCWTWUPKO-UHFFFAOYSA-N 0.000 description 1
- GYDMGBKXPUCXMM-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(3-hydroxybutan-2-yl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(C)C(O)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F GYDMGBKXPUCXMM-UHFFFAOYSA-N 0.000 description 1
- CRIKPZLHYXGADY-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(3-methoxypyridin-2-yl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound COC1=CC=CN=C1N1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 CRIKPZLHYXGADY-UHFFFAOYSA-N 0.000 description 1
- ZEOZVEDVMZVARN-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(3-methylbutan-2-yl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(C)C(C)C)CCCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F ZEOZVEDVMZVARN-UHFFFAOYSA-N 0.000 description 1
- OHCZEYWSVPAKDO-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)piperidine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1C(ON=1)=NC=1C1=CC=CN=C1 OHCZEYWSVPAKDO-UHFFFAOYSA-N 0.000 description 1
- DWQNTZVQKWJWMX-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-fluorophenyl)piperazin-4-ium-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(F)=CC=C1[NH+]1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 DWQNTZVQKWJWMX-UHFFFAOYSA-N 0.000 description 1
- CVSROSZUTBTEPX-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-methoxyphenyl)-3,3-dimethylpiperazine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(OC)=CC=C1N1C(C)(C)CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 CVSROSZUTBTEPX-UHFFFAOYSA-N 0.000 description 1
- HVFVBQYIMMXGRE-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-methoxyphenyl)piperazin-4-ium-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(OC)=CC=C1[NH+]1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 HVFVBQYIMMXGRE-UHFFFAOYSA-N 0.000 description 1
- PVFKXXXXQSMPKE-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-methoxypyridin-2-yl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)=C1 PVFKXXXXQSMPKE-UHFFFAOYSA-N 0.000 description 1
- IKDDKXXAUMOVIY-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-methoxypyrimidin-2-yl)piperazine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound COC1=CC=NC(N2CCN(CC2)C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)=N1 IKDDKXXAUMOVIY-UHFFFAOYSA-N 0.000 description 1
- OFOGSLHNAJXEBL-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-methylmorpholine-3-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound CN1CCOCC1C(=O)N1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 OFOGSLHNAJXEBL-UHFFFAOYSA-N 0.000 description 1
- VSHZHBDIVWKDNU-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-methylpiperidin-1-yl)piperidine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CC(C)CCN1C1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 VSHZHBDIVWKDNU-UHFFFAOYSA-N 0.000 description 1
- COLFNGXJHLEBOB-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(4-methylpyridin-1-ium-2-yl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=CC=[NH+]C(N2CCN(CC2)C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)=C1 COLFNGXJHLEBOB-UHFFFAOYSA-N 0.000 description 1
- QEXNVJFHPWJEQP-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(5-nitropyridin-1-ium-2-yl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH+]1=CC([N+](=O)[O-])=CC=C1N1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCC1 QEXNVJFHPWJEQP-UHFFFAOYSA-N 0.000 description 1
- VKFUNRMEZRZXLK-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(6-fluoro-1H-benzimidazol-2-yl)piperidine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound N1C(=O)C2=CC(Cl)=C(Cl)N2C(CC=2C=C(C(=CC=2)F)C(=O)N2CCC(CC2)C2=NC3=CC=C(C=C3N2)F)=C1 VKFUNRMEZRZXLK-UHFFFAOYSA-N 0.000 description 1
- FWOPQQLWFWZAKK-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(furan-2-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CC=CO1 FWOPQQLWFWZAKK-UHFFFAOYSA-N 0.000 description 1
- HBOUHPZOFLNLLQ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(furan-3-ylmethyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1CC=1C=COC=1 HBOUHPZOFLNLLQ-UHFFFAOYSA-N 0.000 description 1
- UPMCDYBNJNGTEB-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(imidazol-1-ylmethyl)piperidine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1CN1C=CN=C1 UPMCDYBNJNGTEB-UHFFFAOYSA-N 0.000 description 1
- IYKWVJXPHAWZRK-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(morpholin-4-ylmethyl)piperidine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1CN1CCOCC1 IYKWVJXPHAWZRK-UHFFFAOYSA-N 0.000 description 1
- RCMLUIIVXSQGBI-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(morpholine-2-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)C1CNCCO1 RCMLUIIVXSQGBI-UHFFFAOYSA-N 0.000 description 1
- MREMDXASRQCNBL-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(morpholine-4-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)N1CCOCC1 MREMDXASRQCNBL-UHFFFAOYSA-N 0.000 description 1
- DTPZZJVYPVKDSE-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(pyridin-3-ylmethyl)-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1CC1=CC=CN=C1 DTPZZJVYPVKDSE-UHFFFAOYSA-N 0.000 description 1
- ILPILELZFOGZTC-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-(pyridine-2-carbonyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CC=CC=N1 ILPILELZFOGZTC-UHFFFAOYSA-N 0.000 description 1
- QLNHKIMWWLWNAQ-LJQANCHMSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[(2r)-2-hydroxybutanoyl]piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)[C@H](O)CC)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F QLNHKIMWWLWNAQ-LJQANCHMSA-N 0.000 description 1
- WFORBGKUSLZNPA-GFCCVEGCSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[(2r)-2-hydroxypropanoyl]piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)[C@H](O)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F WFORBGKUSLZNPA-GFCCVEGCSA-N 0.000 description 1
- HKANJRYCSLLZCY-LJQANCHMSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[(2r)-pyrrolidine-2-carbonyl]piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)[C@H]1CCCN1 HKANJRYCSLLZCY-LJQANCHMSA-N 0.000 description 1
- WFORBGKUSLZNPA-LBPRGKRZSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[(2s)-2-hydroxypropanoyl]piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F WFORBGKUSLZNPA-LBPRGKRZSA-N 0.000 description 1
- ILSZJCPTHOUFOH-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[(3-fluoropyridin-2-yl)methyl]-1,4-diazepane-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=CN=C1CN1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCC1 ILSZJCPTHOUFOH-UHFFFAOYSA-N 0.000 description 1
- KNNSBZPDHPLRSD-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[1-(methylamino)cyclopropanecarbonyl]piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CCN1C(=O)C1(NC)CC1 KNNSBZPDHPLRSD-UHFFFAOYSA-N 0.000 description 1
- NBFVWALVZPYMMR-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[2-nitro-4-(trifluoromethyl)phenyl]piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 NBFVWALVZPYMMR-UHFFFAOYSA-N 0.000 description 1
- SSHOPWLPAVRYKR-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[3-(trifluoromethyl)phenoxy]piperidine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1OC1=CC=CC(C(F)(F)F)=C1 SSHOPWLPAVRYKR-UHFFFAOYSA-N 0.000 description 1
- UHIHKIWKXBHEIY-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[3-(trifluoromethyl)pyridin-1-ium-2-yl]-1,4-diazepane-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1=[NH+]C=CC=C1C(F)(F)F UHIHKIWKXBHEIY-UHFFFAOYSA-N 0.000 description 1
- PUJUZTYEFQSHAR-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]piperidine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1C(ON=1)=NC=1C1=CC=CC(C(F)(F)F)=C1 PUJUZTYEFQSHAR-UHFFFAOYSA-N 0.000 description 1
- GSHGFAYVWQCEQI-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[4-(trifluoromethyl)pyrimidin-2-yl]piperazine-1-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=NC=CC(C(F)(F)F)=N1 GSHGFAYVWQCEQI-UHFFFAOYSA-N 0.000 description 1
- LJXXEEDZAQKCPJ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[5-(trifluoromethyl)pyridin-1-ium-2-yl]-1,4-diazepane-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1=CC=C(C(F)(F)F)C=[NH+]1 LJXXEEDZAQKCPJ-UHFFFAOYSA-N 0.000 description 1
- QTXPRKGCMYQDHJ-UHFFFAOYSA-N 6,7-dichloro-4-[[4-fluoro-3-[4-[5-(trifluoromethyl)pyridin-1-ium-2-yl]piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=CC=C(C(F)(F)F)C=[NH+]1 QTXPRKGCMYQDHJ-UHFFFAOYSA-N 0.000 description 1
- PKIDPNIFOXPYPZ-UHFFFAOYSA-N 6,8-dichloro-4-[[3-(1,4-diazepan-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=CC(Cl)=C3C(=O)NC=2)C=C1C(=O)N1CCC[NH2+]CC1 PKIDPNIFOXPYPZ-UHFFFAOYSA-N 0.000 description 1
- RXLXIIGOQKRHHY-UHFFFAOYSA-N 6-[1-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]azetidin-3-yl]pyridine-2-carbonitrile Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CC1C1=CC=CC(C#N)=N1 RXLXIIGOQKRHHY-UHFFFAOYSA-N 0.000 description 1
- SZFDVQXJRQUWCK-UHFFFAOYSA-N 6-[4-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-1,4-diazepan-1-yl]pyridin-1-ium-3-carbonitrile;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1=CC=C(C#N)C=[NH+]1 SZFDVQXJRQUWCK-UHFFFAOYSA-N 0.000 description 1
- YTPQSNYVISFGCS-UHFFFAOYSA-N 6-[4-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]piperazin-1-yl]pyridin-1-ium-3-carbonitrile;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=CC=C(C#N)C=[NH+]1 YTPQSNYVISFGCS-UHFFFAOYSA-N 0.000 description 1
- GBSSHPSZEYXMFY-UHFFFAOYSA-N 6-chloro-4-[[3-(1,4-diazepane-1-carbonyl)-4-fluorophenyl]methyl]-7-methyl-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC1=C(C)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=C(F)C=1C(=O)N1CCCNCC1 GBSSHPSZEYXMFY-UHFFFAOYSA-N 0.000 description 1
- GGOKCGHXSGURAV-UHFFFAOYSA-N 6-chloro-4-[[4-fluoro-3-(4-piperidin-1-ylpiperidine-1-carbonyl)phenyl]methyl]-7-methyl-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC1=C(C)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=C(F)C=1C(=O)N(CC1)CCC1N1CCCCC1 GGOKCGHXSGURAV-UHFFFAOYSA-N 0.000 description 1
- SGSKYBFSPOHRSP-UHFFFAOYSA-N 6-chloro-4-[[4-fluoro-3-(4-pyrrolidin-1-ium-1-ylpiperidine-1-carbonyl)phenyl]methyl]-7-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.ClC1=C(C)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=C(F)C=1C(=O)N(CC1)CCC1[NH+]1CCCC1 SGSKYBFSPOHRSP-UHFFFAOYSA-N 0.000 description 1
- KAEVHZSIYLATMK-UHFFFAOYSA-N 6-n-[bis(aziridin-1-yl)phosphoryl]-2-n,2-n,7-trimethylpurine-2,6-diamine Chemical compound C=12N(C)C=NC2=NC(N(C)C)=NC=1NP(=O)(N1CC1)N1CC1 KAEVHZSIYLATMK-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- UKYTYLUITWMKGZ-UHFFFAOYSA-N 7,8-dichloro-4-[[4-fluoro-3-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN2C(C(F)(F)F)=NN=C2CN1C(=O)C1=CC(CC=2N3C=C(Cl)C(Cl)=C3C(=O)NC=2)=CC=C1F UKYTYLUITWMKGZ-UHFFFAOYSA-N 0.000 description 1
- RGVRUQHYQSORBY-UHFFFAOYSA-N 7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyethyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(CCO)CC1OC1CC(N)C(O)C(C)O1 RGVRUQHYQSORBY-UHFFFAOYSA-N 0.000 description 1
- VNLBQRIGUCMDEU-UHFFFAOYSA-N 7-[5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxamide Chemical compound N1C(=O)C2=CC(Cl)=C(Cl)N2C(CC=2C=C(C(=CC=2)F)C(=O)N2CC3=NN=C(N3CC2)C(=O)N)=C1 VNLBQRIGUCMDEU-UHFFFAOYSA-N 0.000 description 1
- KABRXLINDSPGDF-UHFFFAOYSA-N 7-bromoisoquinoline Chemical compound C1=CN=CC2=CC(Br)=CC=C21 KABRXLINDSPGDF-UHFFFAOYSA-N 0.000 description 1
- FLAPYZZVCQHGJR-UHFFFAOYSA-N 7-chloro-4-[[3-(1,4-diazepan-4-ium-1-carbonyl)-4-fluorophenyl]methyl]-6-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=C(Cl)C=C(C(NC=2)=O)N1C=2CC(C=1)=CC=C(F)C=1C(=O)N1CCC[NH2+]CC1 FLAPYZZVCQHGJR-UHFFFAOYSA-N 0.000 description 1
- OWJZRMSQOUZEKH-UHFFFAOYSA-N 7-chloro-4-[[3-[4-(cyclopentanecarbonyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)C1CCCC1 OWJZRMSQOUZEKH-UHFFFAOYSA-N 0.000 description 1
- JBQIASXDSCMFLZ-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-(3-phenyl-6,8-dihydro-5h-imidazo[1,2-a]pyrazine-7-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCN2C1=NC=C2C1=CC=CC=C1 JBQIASXDSCMFLZ-UHFFFAOYSA-N 0.000 description 1
- HVHKOHIUNOAZMM-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-(4-isoquinolin-3-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC=C2C=NC(N3CCN(CC3)C(=O)C3=CC(CC=4N5C=C(Cl)C=C5C(=O)NC=4)=CC=C3F)=CC2=C1 HVHKOHIUNOAZMM-UHFFFAOYSA-N 0.000 description 1
- PULPHVQWRLBRLO-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-(4-propanoylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C(=O)CC)CCN1C(=O)C1=CC(CC=2N3C=C(Cl)C=C3C(=O)NC=2)=CC=C1F PULPHVQWRLBRLO-UHFFFAOYSA-N 0.000 description 1
- XCBMJPIJIWDBFF-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-(4-pyridin-2-ylpiperazine-1-carbonyl)phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C1=CC=CC=N1 XCBMJPIJIWDBFF-UHFFFAOYSA-N 0.000 description 1
- BPTKOTZIEBBPPD-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-(piperazine-1-carbonyl)phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N1CCNCC1 BPTKOTZIEBBPPD-UHFFFAOYSA-N 0.000 description 1
- LDOCJXWDTBBHOG-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]methyl]-2H-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN2C(C(F)(F)F)=NN=C2CN1C(=O)C1=CC(CC=2N3C=C(Cl)C=C3C(=O)NC=2)=CC=C1F LDOCJXWDTBBHOG-UHFFFAOYSA-N 0.000 description 1
- ZXENQDIBAOYHCS-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-[4-(2-fluorobenzoyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=CC=C1C(=O)N1CCN(C(=O)C=2C(=CC=C(CC=3N4C=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 ZXENQDIBAOYHCS-UHFFFAOYSA-N 0.000 description 1
- DMASFPFAQCNLFU-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-[4-(2-phenylacetyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound FC1=CC=C(CC=2N3C=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(=O)CC1=CC=CC=C1 DMASFPFAQCNLFU-UHFFFAOYSA-N 0.000 description 1
- YDENXUDBWWICPS-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-[4-(4-fluorobenzoyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(F)=CC=C1C(=O)N1CCN(C(=O)C=2C(=CC=C(CC=3N4C=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 YDENXUDBWWICPS-UHFFFAOYSA-N 0.000 description 1
- PJNWVAWPLUSLIM-UHFFFAOYSA-N 7-chloro-4-[[4-fluoro-3-[4-(4-methoxybenzoyl)piperazine-1-carbonyl]phenyl]methyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCN(C(=O)C=2C(=CC=C(CC=3N4C=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 PJNWVAWPLUSLIM-UHFFFAOYSA-N 0.000 description 1
- PBCZSGKMGDDXIJ-XMCQDBRXSA-N 7-hydroxystaurosporine Chemical compound N([C@@H](O)C1=C2C3=CC=CC=C3N3C2=C24)C(=O)C1=C2C1=CC=CC=C1N4[C@@H]1C[C@@H](NC)[C@@H](OC)[C@@]3(C)O1 PBCZSGKMGDDXIJ-XMCQDBRXSA-N 0.000 description 1
- PBCZSGKMGDDXIJ-UHFFFAOYSA-N 7beta-hydroxystaurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3C(O)NC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 PBCZSGKMGDDXIJ-UHFFFAOYSA-N 0.000 description 1
- XOLKYLRDCOMHDC-UHFFFAOYSA-N 8-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC21NCNC2=O XOLKYLRDCOMHDC-UHFFFAOYSA-N 0.000 description 1
- JEMMFBJCCNLGNT-UHFFFAOYSA-N 8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylic acid Chemical compound N=1N=CN2C=1CN(C=C2)C(=O)O JEMMFBJCCNLGNT-UHFFFAOYSA-N 0.000 description 1
- FUXVKZWTXQUGMW-FQEVSTJZSA-N 9-Aminocamptothecin Chemical compound C1=CC(N)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 FUXVKZWTXQUGMW-FQEVSTJZSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- BUROJSBIWGDYCN-GAUTUEMISA-N AP 23573 Chemical compound C1C[C@@H](OP(C)(C)=O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 BUROJSBIWGDYCN-GAUTUEMISA-N 0.000 description 1
- 206010000599 Acromegaly Diseases 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- 206010000890 Acute myelomonocytic leukaemia Diseases 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 208000003200 Adenoma Diseases 0.000 description 1
- 206010001233 Adenoma benign Diseases 0.000 description 1
- 108700028369 Alleles Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- 201000003076 Angiosarcoma Diseases 0.000 description 1
- 229940123413 Angiotensin II antagonist Drugs 0.000 description 1
- 108020004491 Antisense DNA Proteins 0.000 description 1
- 108020005544 Antisense RNA Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 206010003226 Arteriovenous fistula Diseases 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 102000007371 Ataxin-3 Human genes 0.000 description 1
- 102000014461 Ataxins Human genes 0.000 description 1
- 108010078286 Ataxins Proteins 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 206010003662 Atrial flutter Diseases 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 108090000433 Aurora kinases Proteins 0.000 description 1
- 102000003989 Aurora kinases Human genes 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 208000030767 Autoimmune encephalitis Diseases 0.000 description 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 1
- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 208000023514 Barrett esophagus Diseases 0.000 description 1
- 208000005440 Basal Cell Neoplasms Diseases 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 1
- 206010068597 Bulbospinal muscular atrophy congenital Diseases 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- CUWBAOQFLODAEN-UHFFFAOYSA-N C1=C2C=CC(=O)CC2=CC2=C1OCO2 Chemical compound C1=C2C=CC(=O)CC2=CC2=C1OCO2 CUWBAOQFLODAEN-UHFFFAOYSA-N 0.000 description 1
- WDRKIMMLUOABKG-UHFFFAOYSA-N C1CN2C=C(C(F)(F)F)N=C2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F Chemical compound C1CN2C=C(C(F)(F)F)N=C2CN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F WDRKIMMLUOABKG-UHFFFAOYSA-N 0.000 description 1
- ZOJDFHRJCRBPRX-UHFFFAOYSA-N C1N(C(=O)O)CC21CN(C(=O)C=1C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=1)F)C2 Chemical compound C1N(C(=O)O)CC21CN(C(=O)C=1C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=1)F)C2 ZOJDFHRJCRBPRX-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 108010082830 CEP 2563 Proteins 0.000 description 1
- FQIBSVYHGVOBQV-UHFFFAOYSA-O CS(NC1=CC=C([N+]2(CCNCC2)C(C(C=C(CC(N(C2=C3)C(Cl)=C3Cl)=CNC2=O)C=C2)=C2F)=O)N=N1)(=O)=O Chemical compound CS(NC1=CC=C([N+]2(CCNCC2)C(C(C=C(CC(N(C2=C3)C(Cl)=C3Cl)=CNC2=O)C=C2)=C2F)=O)N=N1)(=O)=O FQIBSVYHGVOBQV-UHFFFAOYSA-O 0.000 description 1
- 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 description 1
- 101100326430 Caenorhabditis elegans bub-1 gene Proteins 0.000 description 1
- 101100220616 Caenorhabditis elegans chk-2 gene Proteins 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 1
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000003847 Carboxypeptidase B2 Human genes 0.000 description 1
- 108090000201 Carboxypeptidase B2 Proteins 0.000 description 1
- 206010007558 Cardiac failure chronic Diseases 0.000 description 1
- AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 description 1
- 108010078791 Carrier Proteins Proteins 0.000 description 1
- 206010007749 Cataract diabetic Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 102000000844 Cell Surface Receptors Human genes 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 102100025832 Centromere-associated protein E Human genes 0.000 description 1
- 206010008025 Cerebellar ataxia Diseases 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000005243 Chondrosarcoma Diseases 0.000 description 1
- 201000009047 Chordoma Diseases 0.000 description 1
- 208000006332 Choriocarcinoma Diseases 0.000 description 1
- 108010077544 Chromatin Proteins 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 102100031162 Collagen alpha-1(XVIII) chain Human genes 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 208000016998 Conn syndrome Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 208000009798 Craniopharyngioma Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 229930188224 Cryptophycin Natural products 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- 208000014311 Cushing syndrome Diseases 0.000 description 1
- 206010011703 Cyanosis Diseases 0.000 description 1
- 229940122204 Cyclooxygenase inhibitor Drugs 0.000 description 1
- 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 1
- 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 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 108090000323 DNA Topoisomerases Proteins 0.000 description 1
- 102000003915 DNA Topoisomerases Human genes 0.000 description 1
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- 208000016192 Demyelinating disease Diseases 0.000 description 1
- 201000008163 Dentatorubral pallidoluysian atrophy 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
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- CYQFCXCEBYINGO-DLBZAZTESA-N Dronabinol Natural products C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@H]21 CYQFCXCEBYINGO-DLBZAZTESA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 201000009051 Embryonal Carcinoma Diseases 0.000 description 1
- 208000010334 End Stage Liver Disease Diseases 0.000 description 1
- 108010079505 Endostatins Proteins 0.000 description 1
- SAMRUMKYXPVKPA-VFKOLLTISA-N Enocitabine Chemical compound O=C1N=C(NC(=O)CCCCCCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 SAMRUMKYXPVKPA-VFKOLLTISA-N 0.000 description 1
- 206010014967 Ependymoma Diseases 0.000 description 1
- 102400001368 Epidermal growth factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
- 108010074604 Epoetin Alfa Proteins 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 208000000461 Esophageal Neoplasms Diseases 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- 208000006168 Ewing Sarcoma Diseases 0.000 description 1
- XEGWFLXQQZYRSU-UHFFFAOYSA-N FC(F)(F)[N+]=1N=C2N(CCCC2)C1 Chemical compound FC(F)(F)[N+]=1N=C2N(CCCC2)C1 XEGWFLXQQZYRSU-UHFFFAOYSA-N 0.000 description 1
- YFOUUBTUYNJUTO-UHFFFAOYSA-N FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCC2=C1N=NN2CC(F)(F)F Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCC2=C1N=NN2CC(F)(F)F YFOUUBTUYNJUTO-UHFFFAOYSA-N 0.000 description 1
- RSJSPHWAVGWOLX-UHFFFAOYSA-N FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCN2C1=NN=C2C1=CC=CO1 Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(C1)CCN2C1=NN=C2C1=CC=CO1 RSJSPHWAVGWOLX-UHFFFAOYSA-N 0.000 description 1
- NFCFWZINKVVCOO-UHFFFAOYSA-N FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1N1C=CN=C1 Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCC1N1C=CN=C1 NFCFWZINKVVCOO-UHFFFAOYSA-N 0.000 description 1
- VOSFSAHHPWBGFH-UHFFFAOYSA-N FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1=NC2=CC=C(Cl)C=C2S1 Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCCN1C1=NC2=CC=C(Cl)C=C2S1 VOSFSAHHPWBGFH-UHFFFAOYSA-N 0.000 description 1
- BCRAWGISNVGWPM-UHFFFAOYSA-N FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(SN=1)=NC=1C1=CC=CC=C1 Chemical compound FC1=CC=C(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)C=C1C(=O)N(CC1)CCN1C(SN=1)=NC=1C1=CC=CC=C1 BCRAWGISNVGWPM-UHFFFAOYSA-N 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- RSCIYYHIBVZXDI-UHFFFAOYSA-O Fagaridine Chemical compound C1=C2OCOC2=CC2=CC=C3C4=CC=C(OC)C(O)=C4C=[N+](C)C3=C21 RSCIYYHIBVZXDI-UHFFFAOYSA-O 0.000 description 1
- 102000013601 Fanconi Anemia Complementation Group D2 protein Human genes 0.000 description 1
- 108010026653 Fanconi Anemia Complementation Group D2 protein Proteins 0.000 description 1
- 108010077898 Fanconi Anemia Complementation Group E protein Proteins 0.000 description 1
- 102000010634 Fanconi Anemia Complementation Group E protein Human genes 0.000 description 1
- 102100027285 Fanconi anemia group B protein Human genes 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- 108010029961 Filgrastim Proteins 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 1
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
- CEVCTNCUIVEQOY-UHFFFAOYSA-N Fumagillol Natural products O1C(CC=C(C)C)C1(C)C1C(OC)C(O)CCC21CO2 CEVCTNCUIVEQOY-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- GGUVRMBIEPYOKL-WMVCGJOFSA-N GW 409544 Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 GGUVRMBIEPYOKL-WMVCGJOFSA-N 0.000 description 1
- 206010017711 Gangrene Diseases 0.000 description 1
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
- 208000031448 Genomic Instability Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 208000032612 Glial tumor Diseases 0.000 description 1
- 201000010915 Glioblastoma multiforme Diseases 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 102400000321 Glucagon Human genes 0.000 description 1
- 108060003199 Glucagon Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 241000282575 Gorilla Species 0.000 description 1
- ZBLLGPUWGCOJNG-UHFFFAOYSA-N Halichondrin B Natural products CC1CC2(CC(C)C3OC4(CC5OC6C(CC5O4)OC7CC8OC9CCC%10OC(CC(C(C9)C8=C)C%11%12CC%13OC%14C(OC%15CCC(CC(=O)OC7C6C)OC%15C%14O%11)C%13O%12)CC%10=C)CC3O2)OC%16OC(CC1%16)C(O)CC(O)CO ZBLLGPUWGCOJNG-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000001258 Hemangiosarcoma Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 208000003923 Hereditary Corneal Dystrophies Diseases 0.000 description 1
- 108010033040 Histones Proteins 0.000 description 1
- 102000006947 Histones Human genes 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 101000729474 Homo sapiens DNA-directed RNA polymerase I subunit RPA1 Proteins 0.000 description 1
- 101000914679 Homo sapiens Fanconi anemia group B protein Proteins 0.000 description 1
- 101000746367 Homo sapiens Granulocyte colony-stimulating factor Proteins 0.000 description 1
- 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 description 1
- 101000605743 Homo sapiens Kinesin-like protein KIF23 Proteins 0.000 description 1
- 101000585548 Homo sapiens PAXIP1-associated glutamate-rich protein 1 Proteins 0.000 description 1
- 101001113440 Homo sapiens Poly [ADP-ribose] polymerase 2 Proteins 0.000 description 1
- 101001092125 Homo sapiens Replication protein A 70 kDa DNA-binding subunit Proteins 0.000 description 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
- 101000851018 Homo sapiens Vascular endothelial growth factor receptor 1 Proteins 0.000 description 1
- 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 241000282620 Hylobates sp. Species 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
- JJKOTMDDZAJTGQ-DQSJHHFOSA-N Idoxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN2CCCC2)=CC=1)/C1=CC=C(I)C=C1 JJKOTMDDZAJTGQ-DQSJHHFOSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 description 1
- 208000017034 Insulin-resistance syndrome type A Diseases 0.000 description 1
- 206010022680 Intestinal ischaemia Diseases 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 1
- 208000027747 Kennedy disease Diseases 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 102100038406 Kinesin-like protein KIF23 Human genes 0.000 description 1
- 102100023424 Kinesin-like protein KIF2C Human genes 0.000 description 1
- 101710134369 Kinesin-like protein KIF2C Proteins 0.000 description 1
- MLFKVJCWGUZWNV-UHFFFAOYSA-N L-alanosine Natural products OC(=O)C(N)CN(O)N=O MLFKVJCWGUZWNV-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- 108010043135 L-methionine gamma-lyase Proteins 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
- 239000005551 L01XE03 - Erlotinib Substances 0.000 description 1
- DAQAKHDKYAWHCG-UHFFFAOYSA-N Lactacystin Natural products CC(=O)NC(C(O)=O)CSC(=O)C1(C(O)C(C)C)NC(=O)C(C)C1O DAQAKHDKYAWHCG-UHFFFAOYSA-N 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
- 208000018142 Leiomyosarcoma Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
- 206010025282 Lymphoedema Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 208000002569 Machado-Joseph Disease Diseases 0.000 description 1
- 229930126263 Maytansine Natural products 0.000 description 1
- 208000035490 Megakaryoblastic Acute Leukemia Diseases 0.000 description 1
- 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
- 208000035489 Monocytic Acute Leukemia Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 101100073787 Mus musculus Kif20b gene Proteins 0.000 description 1
- 101100462869 Mus musculus Tiparp gene Proteins 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 208000033835 Myelomonocytic Acute Leukemia Diseases 0.000 description 1
- 208000021908 Myocardial disease Diseases 0.000 description 1
- 208000007201 Myocardial reperfusion injury Diseases 0.000 description 1
- NQDQBAQSFQCDTF-UHFFFAOYSA-N N-(3-chlorophenyl)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine methanesulfonic acid Chemical compound CS(O)(=O)=O.Cc1[nH]c2ncnc(Nc3cccc(Cl)c3)c2c1C NQDQBAQSFQCDTF-UHFFFAOYSA-N 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-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
- LHNKAWGUFJRZKI-UHFFFAOYSA-N N1C(=CC=C1)ON1C(CCC1=O)=O Chemical compound N1C(=CC=C1)ON1C(CCC1=O)=O LHNKAWGUFJRZKI-UHFFFAOYSA-N 0.000 description 1
- LNSLXEBBFQFCRI-UHFFFAOYSA-N N1C(=O)C2=CC(Cl)=C(Cl)N2C(CC=2C=C(C(=CC=2)F)C(=O)N2CC3=NN=C(N3CC2)CN(C)C)=C1 Chemical compound N1C(=O)C2=CC(Cl)=C(Cl)N2C(CC=2C=C(C(=CC=2)F)C(=O)N2CC3=NN=C(N3CC2)CN(C)C)=C1 LNSLXEBBFQFCRI-UHFFFAOYSA-N 0.000 description 1
- FTFRZXFNZVCRSK-UHFFFAOYSA-N N4-(3-chloro-4-fluorophenyl)-N6-(1-methyl-4-piperidinyl)pyrimido[5,4-d]pyrimidine-4,6-diamine Chemical compound C1CN(C)CCC1NC1=NC=C(N=CN=C2NC=3C=C(Cl)C(F)=CC=3)C2=N1 FTFRZXFNZVCRSK-UHFFFAOYSA-N 0.000 description 1
- 206010028729 Nasal cavity cancer Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010056969 Necrobiosis lipoidica diabeticorum Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 229940123821 Neurokinin 1 receptor antagonist Drugs 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 102000007999 Nuclear Proteins Human genes 0.000 description 1
- 108010089610 Nuclear Proteins Proteins 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- WNLGISRKEZFSJJ-UHFFFAOYSA-N O=C(C(C=C(CC(N(C1=C2)C(Cl)=C2Cl)=CNC1=O)C=C1)=C1F)N1CC2=NN=C(C3=CC=CN=C3)N2CC1 Chemical compound O=C(C(C=C(CC(N(C1=C2)C(Cl)=C2Cl)=CNC1=O)C=C1)=C1F)N1CC2=NN=C(C3=CC=CN=C3)N2CC1 WNLGISRKEZFSJJ-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 201000010133 Oligodendroglioma Diseases 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 241000243985 Onchocerca volvulus Species 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 102100029882 PAXIP1-associated glutamate-rich protein 1 Human genes 0.000 description 1
- 102000038030 PI3Ks Human genes 0.000 description 1
- 108091007960 PI3Ks Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101150023417 PPARG gene Proteins 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000282577 Pan troglodytes Species 0.000 description 1
- 208000016222 Pancreatic disease Diseases 0.000 description 1
- 241001504519 Papio ursinus Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 description 1
- 229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 description 1
- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 description 1
- 208000007641 Pinealoma Diseases 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 1
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 102100037664 Poly [ADP-ribose] polymerase tankyrase-1 Human genes 0.000 description 1
- 101710129670 Poly [ADP-ribose] polymerase tankyrase-1 Proteins 0.000 description 1
- 102100037477 Poly [ADP-ribose] polymerase tankyrase-2 Human genes 0.000 description 1
- 101710129674 Poly [ADP-ribose] polymerase tankyrase-2 Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 206010036105 Polyneuropathy Diseases 0.000 description 1
- 241000282405 Pongo abelii Species 0.000 description 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 102000029797 Prion Human genes 0.000 description 1
- 108091000054 Prion Proteins 0.000 description 1
- 208000024777 Prion disease Diseases 0.000 description 1
- 208000033826 Promyelocytic Acute Leukemia Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 101710176890 Protein ADP-ribosyltransferase PARP3 Proteins 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 102100034935 Protein mono-ADP-ribosyltransferase PARP3 Human genes 0.000 description 1
- 101710204718 Protein mono-ADP-ribosyltransferase PARP3 Proteins 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- AHHFEZNOXOZZQA-ZEBDFXRSSA-N Ranimustine Chemical compound CO[C@H]1O[C@H](CNC(=O)N(CCCl)N=O)[C@@H](O)[C@H](O)[C@H]1O AHHFEZNOXOZZQA-ZEBDFXRSSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 description 1
- 208000003782 Raynaud disease Diseases 0.000 description 1
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 1
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- 206010061481 Renal injury Diseases 0.000 description 1
- 102100035729 Replication protein A 70 kDa DNA-binding subunit Human genes 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 208000007135 Retinal Neovascularization Diseases 0.000 description 1
- 201000000582 Retinoblastoma Diseases 0.000 description 1
- IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 190014017285 Satraplatin Chemical compound 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 201000010208 Seminoma Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
- 102100031463 Serine/threonine-protein kinase PLK1 Human genes 0.000 description 1
- 101710183160 Serine/threonine-protein kinase PLK1 Proteins 0.000 description 1
- 102100023085 Serine/threonine-protein kinase mTOR Human genes 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 206010040943 Skin Ulcer Diseases 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- OCOKWVBYZHBHLU-UHFFFAOYSA-N Sobuzoxane Chemical compound C1C(=O)N(COC(=O)OCC(C)C)C(=O)CN1CCN1CC(=O)N(COC(=O)OCC(C)C)C(=O)C1 OCOKWVBYZHBHLU-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010041329 Somatostatinoma Diseases 0.000 description 1
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 description 1
- 208000036834 Spinocerebellar ataxia type 3 Diseases 0.000 description 1
- 208000007718 Stable Angina Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 206010042742 Sympathetic ophthalmia Diseases 0.000 description 1
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 1
- 102000002259 TNF-Related Apoptosis-Inducing Ligand Receptors Human genes 0.000 description 1
- 108010000449 TNF-Related Apoptosis-Inducing Ligand Receptors Proteins 0.000 description 1
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- NAVMQTYZDKMPEU-UHFFFAOYSA-N Targretin Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(=C)C1=CC=C(C(O)=O)C=C1 NAVMQTYZDKMPEU-UHFFFAOYSA-N 0.000 description 1
- LGGHDPFKSSRQNS-UHFFFAOYSA-N Tariquidar Chemical compound C1=CC=CC2=CC(C(=O)NC3=CC(OC)=C(OC)C=C3C(=O)NC3=CC=C(C=C3)CCN3CCC=4C=C(C(=CC=4C3)OC)OC)=CN=C21 LGGHDPFKSSRQNS-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 229940123464 Thiazolidinedione Drugs 0.000 description 1
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 1
- 206010043515 Throat cancer Diseases 0.000 description 1
- 108010078233 Thymalfasin Proteins 0.000 description 1
- DKJJVAGXPKPDRL-UHFFFAOYSA-N Tiludronic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)SC1=CC=C(Cl)C=C1 DKJJVAGXPKPDRL-UHFFFAOYSA-N 0.000 description 1
- IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- YCPOZVAOBBQLRI-WDSKDSINSA-N Treosulfan Chemical compound CS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-WDSKDSINSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 1
- 108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
- 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 description 1
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 description 1
- FTNIPWXXIGNQQF-UHFFFAOYSA-N UNPD130147 Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(OC3C(OC(OC4C(OC(O)C(O)C4O)CO)C(O)C3O)CO)C(O)C2O)CO)C(O)C1O FTNIPWXXIGNQQF-UHFFFAOYSA-N 0.000 description 1
- 102000006275 Ubiquitin-Protein Ligases Human genes 0.000 description 1
- 108010083111 Ubiquitin-Protein Ligases Proteins 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 208000002495 Uterine Neoplasms Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 206010046996 Varicose vein Diseases 0.000 description 1
- 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 description 1
- 102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
- 208000008383 Wilms tumor Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 208000006269 X-Linked Bulbo-Spinal Atrophy Diseases 0.000 description 1
- 102100036973 X-ray repair cross-complementing protein 5 Human genes 0.000 description 1
- 101710124921 X-ray repair cross-complementing protein 5 Proteins 0.000 description 1
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
- XMYKNCNAZKMVQN-NYYWCZLTSA-N [(e)-(3-aminopyridin-2-yl)methylideneamino]thiourea Chemical compound NC(=S)N\N=C\C1=NC=CC=C1N XMYKNCNAZKMVQN-NYYWCZLTSA-N 0.000 description 1
- RRGMQHRDBHTZRC-UHFFFAOYSA-N [1-[5-[(6,7-dichloro-1-oxo-2h-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]piperidin-4-yl]-methylazanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1CC([NH2+]C)CCN1C(=O)C1=CC(CC=2N3C(Cl)=C(Cl)C=C3C(=O)NC=2)=CC=C1F RRGMQHRDBHTZRC-UHFFFAOYSA-N 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
- GBTLQIRMUXMWLA-UHFFFAOYSA-N [O-]C(=O)C(F)(F)F.Fc1ccc(Cc2c[nH]c(=O)c3cc(Cl)c(Cl)n23)cc1C(=O)N1CCC(CC1)[NH+]1CCc2ccccc2C1 Chemical compound [O-]C(=O)C(F)(F)F.Fc1ccc(Cc2c[nH]c(=O)c3cc(Cl)c(Cl)n23)cc1C(=O)N1CCC(CC1)[NH+]1CCc2ccccc2C1 GBTLQIRMUXMWLA-UHFFFAOYSA-N 0.000 description 1
- QCLRUNIZLOTOPA-UHFFFAOYSA-N [Pt].CC1=NC=CC(Cl)=C1Cl Chemical compound [Pt].CC1=NC=CC(Cl)=C1Cl QCLRUNIZLOTOPA-UHFFFAOYSA-N 0.000 description 1
- UVIQSJCZCSLXRZ-UBUQANBQSA-N abiraterone acetate Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CC[C@@H](CC4=CC[C@H]31)OC(=O)C)C=C2C1=CC=CN=C1 UVIQSJCZCSLXRZ-UBUQANBQSA-N 0.000 description 1
- 229960004103 abiraterone acetate Drugs 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 208000017733 acquired polycythemia vera Diseases 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 208000037832 acute lymphoblastic B-cell leukemia Diseases 0.000 description 1
- 208000037833 acute lymphoblastic T-cell leukemia Diseases 0.000 description 1
- 208000013593 acute megakaryoblastic leukemia Diseases 0.000 description 1
- 208000020700 acute megakaryocytic leukemia Diseases 0.000 description 1
- 208000011912 acute myelomonocytic leukemia M4 Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- 208000036676 acute undifferentiated leukemia Diseases 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229950005033 alanosine Drugs 0.000 description 1
- DCSBSVSZJRSITC-UHFFFAOYSA-M alendronate sodium trihydrate Chemical compound O.O.O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O DCSBSVSZJRSITC-UHFFFAOYSA-M 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001445 alitretinoin Drugs 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- YETHWGOYCQLNKG-FHERGOJNSA-N alpha-D-Manp-(1->3)-[alpha-D-Manp-(1->6)]-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->2)-D-Manp Chemical compound O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@H]([C@@H](O[C@@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@H](O)[C@@H](CO[C@@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 YETHWGOYCQLNKG-FHERGOJNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229960000473 altretamine Drugs 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229950010817 alvocidib Drugs 0.000 description 1
- BIIVYFLTOXDAOV-YVEFUNNKSA-N alvocidib Chemical compound O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O BIIVYFLTOXDAOV-YVEFUNNKSA-N 0.000 description 1
- 229960003896 aminopterin Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229960002550 amrubicin Drugs 0.000 description 1
- VJZITPJGSQKZMX-XDPRQOKASA-N amrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC=C4C(=O)C=3C(O)=C21)(N)C(=O)C)[C@H]1C[C@H](O)[C@H](O)CO1 VJZITPJGSQKZMX-XDPRQOKASA-N 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 206010002224 anaplastic astrocytoma Diseases 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 230000006427 angiogenic response Effects 0.000 description 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
- 229950001104 anhydrovinblastine Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- CIDNKDMVSINJCG-GKXONYSUSA-N annamycin Chemical compound I[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(=O)CO)C1 CIDNKDMVSINJCG-GKXONYSUSA-N 0.000 description 1
- 150000004303 annulenes Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000002973 anti-dopamine Effects 0.000 description 1
- 230000003388 anti-hormonal effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940045695 antineooplastic colchicine derivative Drugs 0.000 description 1
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 239000003816 antisense DNA Substances 0.000 description 1
- 208000007474 aortic aneurysm Diseases 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 229910052789 astatine Inorganic materials 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 229960005370 atorvastatin Drugs 0.000 description 1
- FQCKMBLVYCEXJB-MNSAWQCASA-L atorvastatin calcium Chemical compound [Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 FQCKMBLVYCEXJB-MNSAWQCASA-L 0.000 description 1
- 206010003668 atrial tachycardia Diseases 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 108010044540 auristatin Proteins 0.000 description 1
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 description 1
- 125000000477 aza group Chemical group 0.000 description 1
- KLNFSAOEKUDMFA-UHFFFAOYSA-N azanide;2-hydroxyacetic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OCC(O)=O KLNFSAOEKUDMFA-UHFFFAOYSA-N 0.000 description 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- 229960000794 baclofen Drugs 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229960003094 belinostat Drugs 0.000 description 1
- NCNRHFGMJRPRSK-MDZDMXLPSA-N belinostat Chemical compound ONC(=O)\C=C\C1=CC=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1 NCNRHFGMJRPRSK-MDZDMXLPSA-N 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- SEXRCKWGFSXUOO-UHFFFAOYSA-N benzo[a]phenazine Chemical compound C1=CC=C2N=C3C4=CC=CC=C4C=CC3=NC2=C1 SEXRCKWGFSXUOO-UHFFFAOYSA-N 0.000 description 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 229960002938 bexarotene Drugs 0.000 description 1
- 229960000997 bicalutamide Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- UBJAHGAUPNGZFF-XOVTVWCYSA-N bms-184476 Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC(C)=O)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)C=3C=CC=CC=3)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OCSC)C(=O)C1=CC=CC=C1 UBJAHGAUPNGZFF-XOVTVWCYSA-N 0.000 description 1
- GMJWGJSDPOAZTP-MIDYMNAOSA-N bms-188797 Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](OC(C)=O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)C=4C=CC=CC=4)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)OC)C(=O)C1=CC=CC=C1 GMJWGJSDPOAZTP-MIDYMNAOSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- 229940028101 boniva Drugs 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 1
- 229960001467 bortezomib Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000003560 cancer drug Substances 0.000 description 1
- 229940022399 cancer vaccine Drugs 0.000 description 1
- 238000009566 cancer vaccine Methods 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 229960004117 capecitabine Drugs 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- WNRZHQBJSXRYJK-UHFFFAOYSA-N carboxyamidotriazole Chemical compound NC1=C(C(=O)N)N=NN1CC(C=C1Cl)=CC(Cl)=C1C(=O)C1=CC=C(Cl)C=C1 WNRZHQBJSXRYJK-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000002612 cardiopulmonary effect Effects 0.000 description 1
- 229930188550 carminomycin Natural products 0.000 description 1
- XREUEWVEMYWFFA-UHFFFAOYSA-N carminomycin I Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XREUEWVEMYWFFA-UHFFFAOYSA-N 0.000 description 1
- 229960003261 carmofur Drugs 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 229950001725 carubicin Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229940047495 celebrex Drugs 0.000 description 1
- 229960000590 celecoxib Drugs 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000006369 cell cycle progression Effects 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 208000025997 central nervous system neoplasm Diseases 0.000 description 1
- 108010031379 centromere protein E Proteins 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 101150113535 chek1 gene Proteins 0.000 description 1
- IQCIQDNWBGEGRL-UHFFFAOYSA-N chembl1614651 Chemical compound O=C1C2=C(O)C=CC(O)=C2N2N=C(CNCCO)C3=CC=C(NCCCN)C1=C32 IQCIQDNWBGEGRL-UHFFFAOYSA-N 0.000 description 1
- YOQPCWIXYUNEET-UHFFFAOYSA-N chembl307697 Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)=NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YOQPCWIXYUNEET-UHFFFAOYSA-N 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 229940044683 chemotherapy drug Drugs 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 208000006990 cholangiocarcinoma Diseases 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 210000003483 chromatin Anatomy 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 208000024207 chronic leukemia Diseases 0.000 description 1
- 208000011444 chronic liver failure Diseases 0.000 description 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 description 1
- AMLYAMJWYAIXIA-VWNVYAMZSA-N cilengitide Chemical compound N1C(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](C(C)C)N(C)C(=O)[C@H]1CC1=CC=CC=C1 AMLYAMJWYAIXIA-VWNVYAMZSA-N 0.000 description 1
- 229950009003 cilengitide Drugs 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 230000005796 circulatory shock Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- ACSIXWWBWUQEHA-UHFFFAOYSA-N clodronic acid Chemical compound OP(O)(=O)C(Cl)(Cl)P(O)(O)=O ACSIXWWBWUQEHA-UHFFFAOYSA-N 0.000 description 1
- 229960002286 clodronic acid Drugs 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000003184 complementary RNA Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 206010011005 corneal dystrophy Diseases 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- POADTFBBIXOWFJ-VWLOTQADSA-N cositecan Chemical compound C1=CC=C2C(CC[Si](C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 POADTFBBIXOWFJ-VWLOTQADSA-N 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 108010006226 cryptophycin Proteins 0.000 description 1
- PSNOPSMXOBPNNV-VVCTWANISA-N cryptophycin 1 Chemical compound C1=C(Cl)C(OC)=CC=C1C[C@@H]1C(=O)NC[C@@H](C)C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@H](C)[C@@H]2[C@H](O2)C=2C=CC=CC=2)C/C=C/C(=O)N1 PSNOPSMXOBPNNV-VVCTWANISA-N 0.000 description 1
- PSNOPSMXOBPNNV-UHFFFAOYSA-N cryptophycin-327 Natural products C1=C(Cl)C(OC)=CC=C1CC1C(=O)NCC(C)C(=O)OC(CC(C)C)C(=O)OC(C(C)C2C(O2)C=2C=CC=CC=2)CC=CC(=O)N1 PSNOPSMXOBPNNV-UHFFFAOYSA-N 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 229950006614 cytarabine ocfosfate Drugs 0.000 description 1
- 102000003675 cytokine receptors Human genes 0.000 description 1
- 108010057085 cytokine receptors Proteins 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 239000002619 cytotoxin Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 229960003603 decitabine Drugs 0.000 description 1
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229960000605 dexrazoxane Drugs 0.000 description 1
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
- 201000007025 diabetic cataract Diseases 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LFQCJSBXBZRMTN-OAQYLSRUSA-N diflomotecan Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC(F)=C(F)C=C3N=C21 LFQCJSBXBZRMTN-OAQYLSRUSA-N 0.000 description 1
- 125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 description 1
- 125000005049 dihydrooxadiazolyl group Chemical group O1N(NC=C1)* 0.000 description 1
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 description 1
- 125000005051 dihydropyrazinyl group Chemical group N1(CC=NC=C1)* 0.000 description 1
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 description 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 description 1
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 description 1
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 125000005058 dihydrotriazolyl group Chemical group N1(NNC=C1)* 0.000 description 1
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical group C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
- 229950009278 dimesna Drugs 0.000 description 1
- KQYGMURBTJPBPQ-UHFFFAOYSA-L disodium;2-(2-sulfonatoethyldisulfanyl)ethanesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCSSCCS([O-])(=O)=O KQYGMURBTJPBPQ-UHFFFAOYSA-L 0.000 description 1
- ZZFKAZHZSSJSSE-UHFFFAOYSA-L disodium;[(cycloheptylamino)-[hydroxy(oxido)phosphoryl]methyl]-hydroxyphosphinate;hydrate Chemical compound O.[Na+].[Na+].OP(O)(=O)C(P([O-])([O-])=O)NC1CCCCCC1 ZZFKAZHZSSJSSE-UHFFFAOYSA-L 0.000 description 1
- IWLDTXOHXPDPQG-UHFFFAOYSA-L disodium;hydroxy-[1-hydroxy-1-[hydroxy(oxido)phosphoryl]-3-pyrrolidin-1-ylpropyl]phosphinate Chemical compound [Na+].[Na+].OP(=O)(O)C(P([O-])([O-])=O)(O)CCN1CCCC1 IWLDTXOHXPDPQG-UHFFFAOYSA-L 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- AMRJKAQTDDKMCE-UHFFFAOYSA-N dolastatin Chemical compound CC(C)C(N(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(C(C)C)C(OC)CC(=O)N1CCCC1C(OC)C(C)C(=O)NC(C=1SC=CN=1)CC1=CC=CC=C1 AMRJKAQTDDKMCE-UHFFFAOYSA-N 0.000 description 1
- 229930188854 dolastatin Natural products 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 229960004242 dronabinol Drugs 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 229940121647 egfr inhibitor Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229950005450 emitefur Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 238000013171 endarterectomy Methods 0.000 description 1
- 208000030172 endocrine system disease Diseases 0.000 description 1
- 206010014801 endophthalmitis Diseases 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 229950011487 enocitabine Drugs 0.000 description 1
- HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 description 1
- INVTYAOGFAGBOE-UHFFFAOYSA-N entinostat Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC(=O)OCC1=CC=CN=C1 INVTYAOGFAGBOE-UHFFFAOYSA-N 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 229940116977 epidermal growth factor Drugs 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- 229960003388 epoetin alfa Drugs 0.000 description 1
- 229930013356 epothilone Natural products 0.000 description 1
- 150000003883 epothilone derivatives Chemical class 0.000 description 1
- 108700002672 epoxomicin Proteins 0.000 description 1
- DOGIDQKFVLKMLQ-JTHVHQAWSA-N epoxomicin Chemical compound CC[C@H](C)[C@H](N(C)C(C)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)[C@@]1(C)CO1 DOGIDQKFVLKMLQ-JTHVHQAWSA-N 0.000 description 1
- 229960001433 erlotinib Drugs 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 230000010437 erythropoiesis Effects 0.000 description 1
- 201000004101 esophageal cancer Diseases 0.000 description 1
- 229960001842 estramustine Drugs 0.000 description 1
- FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- QVSZSYLATZQQSP-UHFFFAOYSA-N ethyl 1-[1-[5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]piperidin-4-yl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 QVSZSYLATZQQSP-UHFFFAOYSA-N 0.000 description 1
- YTHGWAWGWQVOMS-UHFFFAOYSA-N ethyl 1-[1-[5-[(6,7-dichloro-1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl]piperidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1CCN(C(=O)C=2C(=CC=C(CC=3N4C(Cl)=C(Cl)C=C4C(=O)NC=3)C=2)F)CC1 YTHGWAWGWQVOMS-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- LIQODXNTTZAGID-OCBXBXKTSA-N etoposide phosphate Chemical compound COC1=C(OP(O)(O)=O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 LIQODXNTTZAGID-OCBXBXKTSA-N 0.000 description 1
- 229960000752 etoposide phosphate Drugs 0.000 description 1
- ZVYVPGLRVWUPMP-FYSMJZIKSA-N exatecan Chemical compound C1C[C@H](N)C2=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC3=CC(F)=C(C)C1=C32 ZVYVPGLRVWUPMP-FYSMJZIKSA-N 0.000 description 1
- 229950009429 exatecan Drugs 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZZCHHVUQYRMYLW-HKBQPEDESA-N farglitazar Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZZCHHVUQYRMYLW-HKBQPEDESA-N 0.000 description 1
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
- 229960002297 fenofibrate Drugs 0.000 description 1
- 230000020764 fibrinolysis Effects 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 229960004177 filgrastim Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
- 229960004039 finasteride Drugs 0.000 description 1
- 229960000390 fludarabine Drugs 0.000 description 1
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
- 229960000676 flunisolide Drugs 0.000 description 1
- XSFJVAJPIHIPKU-XWCQMRHXSA-N flunisolide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O XSFJVAJPIHIPKU-XWCQMRHXSA-N 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 229960002690 fluphenazine Drugs 0.000 description 1
- 229960002074 flutamide Drugs 0.000 description 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229960002258 fulvestrant Drugs 0.000 description 1
- CEVCTNCUIVEQOY-STXHBLNNSA-N fumagillol Chemical compound C([C@@H](O)[C@H](C1[C@]2(C)[C@H](O2)CC=C(C)C)OC)C[C@@]21CO2 CEVCTNCUIVEQOY-STXHBLNNSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229950004410 galocitabine Drugs 0.000 description 1
- 229960002963 ganciclovir Drugs 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229960002584 gefitinib Drugs 0.000 description 1
- 229960003627 gemfibrozil Drugs 0.000 description 1
- 229940045109 genistein Drugs 0.000 description 1
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 1
- 235000006539 genistein Nutrition 0.000 description 1
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 1
- 208000004104 gestational diabetes Diseases 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
- 229960004666 glucagon Drugs 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 229950011595 glufosfamide Drugs 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- MFWNKCLOYSRHCJ-BTTYYORXSA-N granisetron Chemical compound C1=CC=C2C(C(=O)N[C@H]3C[C@H]4CCC[C@@H](C3)N4C)=NN(C)C2=C1 MFWNKCLOYSRHCJ-BTTYYORXSA-N 0.000 description 1
- 229960003727 granisetron Drugs 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 201000009277 hairy cell leukemia Diseases 0.000 description 1
- FXNFULJVOQMBCW-VZBLNRDYSA-N halichondrin b Chemical compound O([C@@H]1[C@@H](C)[C@@H]2O[C@@H]3C[C@@]4(O[C@H]5[C@@H](C)C[C@@]6(C[C@@H]([C@@H]7O[C@@H](C[C@@H]7O6)[C@@H](O)C[C@@H](O)CO)C)O[C@H]5C4)O[C@@H]3C[C@@H]2O[C@H]1C[C@@H]1C(=C)[C@H](C)C[C@@H](O1)CC[C@H]1C(=C)C[C@@H](O1)CC1)C(=O)C[C@H](O2)CC[C@H]3[C@H]2[C@H](O2)[C@@H]4O[C@@H]5C[C@@]21O[C@@H]5[C@@H]4O3 FXNFULJVOQMBCW-VZBLNRDYSA-N 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 208000025750 heavy chain disease Diseases 0.000 description 1
- 201000002222 hemangioblastoma Diseases 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 239000002874 hemostatic agent Substances 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 description 1
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 229940015872 ibandronate Drugs 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 229960000908 idarubicin Drugs 0.000 description 1
- 229950002248 idoxifene Drugs 0.000 description 1
- 208000009326 ileitis Diseases 0.000 description 1
- 229960002411 imatinib Drugs 0.000 description 1
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000000367 immunologic factor Substances 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000010874 in vitro model Methods 0.000 description 1
- 229950006971 incadronic acid Drugs 0.000 description 1
- 201000001371 inclusion conjunctivitis Diseases 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000013256 infectious meningitis Diseases 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 208000037906 ischaemic injury Diseases 0.000 description 1
- 208000023589 ischemic disease Diseases 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 description 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- LFUJIPVWTMGYDG-UHFFFAOYSA-N isoquinoline-1,5-diol Chemical compound N1=CC=C2C(O)=CC=CC2=C1O LFUJIPVWTMGYDG-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 229960005280 isotretinoin Drugs 0.000 description 1
- 125000003971 isoxazolinyl group Chemical group 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 208000037806 kidney injury Diseases 0.000 description 1
- DAQAKHDKYAWHCG-RWTHQLGUSA-N lactacystin Chemical compound CC(=O)N[C@H](C(O)=O)CSC(=O)[C@]1([C@@H](O)C(C)C)NC(=O)[C@H](C)[C@@H]1O DAQAKHDKYAWHCG-RWTHQLGUSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001614 levamisole Drugs 0.000 description 1
- UGFHIPBXIWJXNA-UHFFFAOYSA-N liarozole Chemical compound ClC1=CC=CC(C(C=2C=C3NC=NC3=CC=2)N2C=NC=C2)=C1 UGFHIPBXIWJXNA-UHFFFAOYSA-N 0.000 description 1
- 229950007056 liarozole Drugs 0.000 description 1
- 229940002661 lipitor Drugs 0.000 description 1
- 206010024627 liposarcoma Diseases 0.000 description 1
- 230000003212 lipotrophic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 229950000909 lometrexol Drugs 0.000 description 1
- 229960003538 lonidamine Drugs 0.000 description 1
- WDRYRZXSPDWGEB-UHFFFAOYSA-N lonidamine Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=C(Cl)C=C1Cl WDRYRZXSPDWGEB-UHFFFAOYSA-N 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
- 239000003055 low molecular weight heparin Substances 0.000 description 1
- 229940127215 low-molecular weight heparin Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000012804 lymphangiosarcoma Diseases 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 208000002502 lymphedema Diseases 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 241001515942 marmosets Species 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- WKPWGQKGSOKKOO-RSFHAFMBSA-N maytansine Chemical compound CO[C@@H]([C@@]1(O)C[C@](OC(=O)N1)([C@H]([C@@H]1O[C@@]1(C)[C@@H](OC(=O)[C@H](C)N(C)C(C)=O)CC(=O)N1C)C)[H])\C=C\C=C(C)\CC2=CC(OC)=C(Cl)C1=C2 WKPWGQKGSOKKOO-RSFHAFMBSA-N 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 description 1
- 229960000300 mesoridazine Drugs 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- LHGVCFRRQZZMCK-UHFFFAOYSA-N methyl 4-chloro-1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC(Cl)=CN1 LHGVCFRRQZZMCK-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
- 229960004503 metoclopramide Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 239000002395 mineralocorticoid Substances 0.000 description 1
- VMMKGHQPQIEGSQ-UHFFFAOYSA-N minodronic acid Chemical compound C1=CC=CN2C(CC(O)(P(O)(O)=O)P(O)(O)=O)=CN=C21 VMMKGHQPQIEGSQ-UHFFFAOYSA-N 0.000 description 1
- 229950011129 minodronic acid Drugs 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 201000005518 mononeuropathy Diseases 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 208000001611 myxosarcoma Diseases 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- PFPSZGPAQFBVHZ-UHFFFAOYSA-N n-(3-chlorophenyl)-2-[(4-phenyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]acetamide Chemical compound ClC1=CC=CC(NC(=O)CSC=2N(C(C=3C=CN=CC=3)=NN=2)C=2C=CC=CC=2)=C1 PFPSZGPAQFBVHZ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- CMEGANPVAXDBPL-INIZCTEOSA-N n-[(7s)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(SC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC CMEGANPVAXDBPL-INIZCTEOSA-N 0.000 description 1
- TVYPSLDUBVTDIS-FUOMVGGVSA-N n-[1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C(=CN(C(=O)N=2)[C@H]2[C@@H]([C@H](O)[C@@H](C)O2)O)F)=C1 TVYPSLDUBVTDIS-FUOMVGGVSA-N 0.000 description 1
- ZDUZYDDAHVZGCI-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-9-hydroxy-5,6-dimethylpyrido[4,3-b]carbazole-1-carboxamide Chemical compound CN1C2=CC=C(O)C=C2C2=C1C(C)=C1C=CN=C(C(=O)NCCN(C)C)C1=C2 ZDUZYDDAHVZGCI-UHFFFAOYSA-N 0.000 description 1
- XBGNERSKEKDZDS-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]acridine-4-carboxamide Chemical compound C1=CC=C2N=C3C(C(=O)NCCN(C)C)=CC=CC3=CC2=C1 XBGNERSKEKDZDS-UHFFFAOYSA-N 0.000 description 1
- GWLFIMOOGVXSMZ-UHFFFAOYSA-N n-[[1-[2-(diethylamino)ethylamino]-7-methoxy-9-oxothioxanthen-4-yl]methyl]formamide Chemical compound S1C2=CC=C(OC)C=C2C(=O)C2=C1C(CNC=O)=CC=C2NCCN(CC)CC GWLFIMOOGVXSMZ-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FKORGLNGEASTQE-UHFFFAOYSA-N naphthalene-1,3-disulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 FKORGLNGEASTQE-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 201000008043 necrobiosis lipoidica Diseases 0.000 description 1
- 229950007221 nedaplatin Drugs 0.000 description 1
- 201000008026 nephroblastoma Diseases 0.000 description 1
- 208000009928 nephrosis Diseases 0.000 description 1
- 231100001027 nephrosis Toxicity 0.000 description 1
- PUUSSSIBPPTKTP-UHFFFAOYSA-N neridronic acid Chemical compound NCCCCCC(O)(P(O)(O)=O)P(O)(O)=O PUUSSSIBPPTKTP-UHFFFAOYSA-N 0.000 description 1
- 229950010733 neridronic acid Drugs 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229940101270 nicotinamide adenine dinucleotide (nad) Drugs 0.000 description 1
- XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
- 229960002653 nilutamide Drugs 0.000 description 1
- 229960001420 nimustine Drugs 0.000 description 1
- VFEDRRNHLBGPNN-UHFFFAOYSA-N nimustine Chemical compound CC1=NC=C(CNC(=O)N(CCCl)N=O)C(N)=N1 VFEDRRNHLBGPNN-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 208000002042 onchocerciasis Diseases 0.000 description 1
- 229960005343 ondansetron Drugs 0.000 description 1
- 201000005443 oral cavity cancer Diseases 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 229940078646 other antiemetics in atc Drugs 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000001898 pallidal effect Effects 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
- 229940046231 pamidronate Drugs 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 description 1
- 229960005184 panobinostat Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 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
- 229960002340 pentostatin Drugs 0.000 description 1
- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- 208000028591 pheochromocytoma Diseases 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229950004317 pinafide Drugs 0.000 description 1
- 208000024724 pineal body neoplasm Diseases 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- PEZPMAYDXJQYRV-UHFFFAOYSA-N pixantrone Chemical compound O=C1C2=CN=CC=C2C(=O)C2=C1C(NCCN)=CC=C2NCCN PEZPMAYDXJQYRV-UHFFFAOYSA-N 0.000 description 1
- 229940037129 plain mineralocorticoids for systemic use Drugs 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229950008499 plitidepsin Drugs 0.000 description 1
- UUSZLLQJYRSZIS-LXNNNBEUSA-N plitidepsin Chemical compound CN([C@H](CC(C)C)C(=O)N[C@@H]1C(=O)N[C@@H]([C@H](CC(=O)O[C@H](C(=O)[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(OC)=CC=2)C(=O)O[C@@H]1C)C(C)C)O)[C@@H](C)CC)C(=O)[C@@H]1CCCN1C(=O)C(C)=O UUSZLLQJYRSZIS-LXNNNBEUSA-N 0.000 description 1
- 108010049948 plitidepsin Proteins 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 108010013138 poly(ADP)-ribosylated proteins Proteins 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 208000037244 polycythemia vera Diseases 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 108010040003 polyglutamine Proteins 0.000 description 1
- 229920000155 polyglutamine Polymers 0.000 description 1
- 102000054765 polymorphisms of proteins Human genes 0.000 description 1
- 230000007824 polyneuropathy Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- VWBQYTRBTXKKOG-IYNICTALSA-M pravastatin sodium Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 VWBQYTRBTXKKOG-IYNICTALSA-M 0.000 description 1
- 201000011461 pre-eclampsia Diseases 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 208000013846 primary aldosteronism Diseases 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
- 229960003111 prochlorperazine Drugs 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000004845 protein aggregation Effects 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000001107 pteroylglutamyl group Chemical group 0.000 description 1
- 229950007401 pumitepa Drugs 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 description 1
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 108010077182 raf Kinases Proteins 0.000 description 1
- 102000009929 raf Kinases Human genes 0.000 description 1
- 229960004432 raltitrexed Drugs 0.000 description 1
- 229960002185 ranimustine Drugs 0.000 description 1
- 108091006084 receptor activators Proteins 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000000463 red nucleus Anatomy 0.000 description 1
- 102000037983 regulatory factors Human genes 0.000 description 1
- 108091008025 regulatory factors Proteins 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000028617 response to DNA damage stimulus Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940100552 retinamide Drugs 0.000 description 1
- 230000001177 retroviral effect Effects 0.000 description 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229940089617 risedronate Drugs 0.000 description 1
- XMSXOLDPMGMWTH-UHFFFAOYSA-N rivoglitazone Chemical compound CN1C2=CC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O XMSXOLDPMGMWTH-UHFFFAOYSA-N 0.000 description 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
- 229960000371 rofecoxib Drugs 0.000 description 1
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 description 1
- OHRURASPPZQGQM-UHFFFAOYSA-N romidepsin Natural products O1C(=O)C(C(C)C)NC(=O)C(=CC)NC(=O)C2CSSCCC=CC1CC(=O)NC(C(C)C)C(=O)N2 OHRURASPPZQGQM-UHFFFAOYSA-N 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 description 1
- 229960003271 rosiglitazone maleate Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229960005399 satraplatin Drugs 0.000 description 1
- 208000018964 sebaceous gland cancer Diseases 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
- BTIHMVBBUGXLCJ-OAHLLOKOSA-N seliciclib Chemical compound C=12N=CN(C(C)C)C2=NC(N[C@@H](CO)CC)=NC=1NCC1=CC=CC=C1 BTIHMVBBUGXLCJ-OAHLLOKOSA-N 0.000 description 1
- WUWDLXZGHZSWQZ-WQLSENKSSA-N semaxanib Chemical compound N1C(C)=CC(C)=C1\C=C/1C2=CC=CC=C2NC\1=O WUWDLXZGHZSWQZ-WQLSENKSSA-N 0.000 description 1
- 229950003647 semaxanib Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
- 229950010372 sobuzoxane Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- JJICLMJFIKGAAU-UHFFFAOYSA-M sodium;2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)purin-6-olate Chemical compound [Na+].NC1=NC([O-])=C2N=CN(COC(CO)CO)C2=N1 JJICLMJFIKGAAU-UHFFFAOYSA-M 0.000 description 1
- NSFFYSQTVOCNLX-JKIHJDPOSA-M sodium;[(2r,3s,4s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl octadecyl phosphate;hydrate Chemical compound O.[Na+].O[C@H]1[C@H](O)[C@@H](COP([O-])(=O)OCCCCCCCCCCCCCCCCCC)O[C@H]1N1C(=O)N=C(N)C=C1 NSFFYSQTVOCNLX-JKIHJDPOSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229960003787 sorafenib Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940063675 spermine Drugs 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 206010062261 spinal cord neoplasm Diseases 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
- CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 201000008759 sweat gland cancer Diseases 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 201000008753 synovium neoplasm Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VAZAPHZUAVEOMC-UHFFFAOYSA-N tacedinaline Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)NC1=CC=CC=C1N VAZAPHZUAVEOMC-UHFFFAOYSA-N 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001674 tegafur Drugs 0.000 description 1
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 102000055501 telomere Human genes 0.000 description 1
- 108091035539 telomere Proteins 0.000 description 1
- 210000003411 telomere Anatomy 0.000 description 1
- 229960000235 temsirolimus Drugs 0.000 description 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005886 tetrahydrobenzothienyl group Chemical group 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 description 1
- 229960004231 thymalfasin Drugs 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 229940019375 tiludronate Drugs 0.000 description 1
- 229950002376 tirapazamine Drugs 0.000 description 1
- ORYDPOVDJJZGHQ-UHFFFAOYSA-N tirapazamine Chemical compound C1=CC=CC2=[N+]([O-])C(N)=N[N+]([O-])=C21 ORYDPOVDJJZGHQ-UHFFFAOYSA-N 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 229960005026 toremifene Drugs 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
- 206010044325 trachoma Diseases 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 229960003181 treosulfan Drugs 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 229960005526 triapine Drugs 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- ZNRGQMMCGHDTEI-ITGUQSILSA-N tropisetron Chemical compound C1=CC=C2C(C(=O)O[C@H]3C[C@H]4CC[C@@H](C3)N4C)=CNC2=C1 ZNRGQMMCGHDTEI-ITGUQSILSA-N 0.000 description 1
- 229960003688 tropisetron Drugs 0.000 description 1
- 229950010147 troxacitabine Drugs 0.000 description 1
- RXRGZNYSEHTMHC-BQBZGAKWSA-N troxacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)OC1 RXRGZNYSEHTMHC-BQBZGAKWSA-N 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000005909 tumor killing Effects 0.000 description 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- 229960000653 valrubicin Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
- 208000027185 varicose disease Diseases 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 229960005212 vindesine sulfate Drugs 0.000 description 1
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229940072168 zocor Drugs 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
- 229940002005 zometa Drugs 0.000 description 1
- VLCYCQAOQCDTCN-ZCFIWIBFSA-N α-difluoromethylornithine Chemical compound NCCC[C@@](N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-ZCFIWIBFSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurology (AREA)
- Virology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Molecular Biology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0610670A GB0610670D0 (en) | 2006-05-31 | 2006-05-31 | Therapeutic compounds |
| GB0610670.2 | 2006-05-31 | ||
| GB0707359.6 | 2007-04-17 | ||
| GB0707359A GB0707359D0 (en) | 2007-04-17 | 2007-04-17 | Therapeutic compounds |
| PCT/GB2007/050300 WO2007138355A1 (en) | 2006-05-31 | 2007-05-29 | Pyrrolo[1,2-a]pyrazin-1(2h)-one and pyrrolo[1,2-d][1,2,4]triazin-1(2h)-one derivatives as inhibitors of poly(adp-ribose)polymerase(parp) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009538897A JP2009538897A (ja) | 2009-11-12 |
| JP2009538897A5 JP2009538897A5 (enExample) | 2010-07-22 |
| JP5271897B2 true JP5271897B2 (ja) | 2013-08-21 |
Family
ID=38377212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009512682A Expired - Fee Related JP5271897B2 (ja) | 2006-05-31 | 2007-05-29 | ポリ（ＡＤＰ−リボース）ポリメラーゼ（ＰＡＲＰ）の阻害剤としての、ピロロ［１，２−ａ］ピラジン−１（２Ｈ）−オン及びピロロ［１，２−ｄ］［１，２，４］トリアジン−１（２Ｈ）−オン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7834015B2 (enExample) |
| EP (1) | EP2032140A1 (enExample) |
| JP (1) | JP5271897B2 (enExample) |
| AU (1) | AU2007266840B2 (enExample) |
| CA (1) | CA2652167A1 (enExample) |
| WO (1) | WO2007138355A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0610680D0 (en) * | 2006-05-31 | 2006-07-12 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| CN101616919B (zh) * | 2006-12-28 | 2012-10-10 | 雅培制药有限公司 | 聚（adp核糖）聚合酶抑制剂 |
| AR070221A1 (es) * | 2008-01-23 | 2010-03-25 | Astrazeneca Ab | Derivados de ftalazinona inhibidores de polimerasas, composiciones farmaceuticas que los contienen y usos de los mismos para prevenir y/o tratar tumores cancerigenos,lesiones isquemicas y otras enfermedades asociadas. |
| GB0804755D0 (en) * | 2008-03-14 | 2008-04-16 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| GB0907515D0 (en) * | 2009-04-30 | 2009-06-10 | Glaxo Group Ltd | Compounds |
| CA2794861A1 (en) * | 2010-04-16 | 2011-10-20 | Abbvie Inc. | Pyrrolopyrazinone inhibitors of kinases |
| ES2590682T3 (es) * | 2010-12-02 | 2016-11-23 | Shanghai De Novo Pharmatech Co Ltd. | Derivados heterocíclicos, procesos de preparación y usos médicos de los mismos |
| CN103130723B (zh) | 2011-11-30 | 2015-01-14 | 成都地奥制药集团有限公司 | 一种多聚(adp-核糖)聚合酶抑制剂 |
| HUE030067T2 (en) * | 2012-03-28 | 2017-04-28 | Merck Patent Gmbh | Bicyclic pyrazinone derivatives |
| KR20150011838A (ko) * | 2012-06-20 | 2015-02-02 | 에프. 호프만-라 로슈 아게 | 탄키라아제 억제제로서의 피롤로피라존 |
| CN112521369A (zh) | 2013-03-13 | 2021-03-19 | 福马治疗股份有限公司 | 用于抑制fasn的化合物及组合物 |
| KR101670126B1 (ko) * | 2013-09-13 | 2016-10-27 | 일동제약(주) | 신규 프탈라지논 유도체 및 그 제조방법 |
| BR112017000470B1 (pt) | 2014-07-07 | 2022-11-29 | Jiangsu Hengrui Medicine Co., Ltd | Compostos, composição farmacêutica e uso do composto ou da composição |
| US9994570B2 (en) | 2014-11-26 | 2018-06-12 | Merck Sharp & Dohme Corp. | Bridged diazepane orexin receptor antagonists |
| CN106749261A (zh) * | 2015-11-23 | 2017-05-31 | 中国科学院上海药物研究所 | 一类取代三唑并哌嗪类parp抑制剂及其制备方法和用途 |
| CN107406453B (zh) * | 2016-01-05 | 2018-12-28 | 江苏恒瑞医药股份有限公司 | 一种btk激酶抑制剂的结晶形式及其制备方法 |
| CN106939002B (zh) * | 2016-01-05 | 2019-09-24 | 江苏恒瑞医药股份有限公司 | 一种btk激酶抑制剂的结晶形式及其制备方法 |
| CN105646497B (zh) * | 2016-02-01 | 2019-06-04 | 南京格亚医药科技有限公司 | 吡咯并三嗪酮衍生物 |
| 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) |
| WO2020092395A1 (en) | 2018-10-29 | 2020-05-07 | Forma Therapeutics, Inc. | SOLID FORMS OF (4-(2-FLUORO-4-(1-METHYL-1 H-BENZO[d]IMIDAZOL-5-YL)BENZOYL) PIPERAZIN-1-YL)(1-HYDROXYCYCLOPROPYL)METHANONE |
| CA3159461A1 (en) | 2019-11-25 | 2021-06-03 | Iwao Ojima | Combination therapy using fabp5 inhibitors with taxanes for treatment of cancer |
| AU2020444056A1 (en) | 2020-04-21 | 2022-11-17 | Idience Co., Ltd. | Crystalline forms of phthalazinone compound |
| EP4139298A4 (en) | 2020-04-21 | 2024-05-22 | Idience Co., Ltd. | Process for preparing a phthalazinone derivative and intermediates thereof |
| US12059419B2 (en) | 2020-10-16 | 2024-08-13 | Idience Co., Ltd. | Pharmaceutical composition comprising phthalazinone derivatives |
| WO2024046420A1 (zh) * | 2022-08-31 | 2024-03-07 | 江苏恒瑞医药股份有限公司 | 稠合二环类化合物、其制备方法及其在医药上的应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5719147A (en) | 1992-06-29 | 1998-02-17 | Merck & Co., Inc. | Morpholine and thiomorpholine tachykinin receptor antagonists |
| AU691958B2 (en) | 1994-08-12 | 1998-05-28 | Myriad Genetics, Inc. | 17q-linked breast and ovarian cancer susceptibility gene |
| WO1996005306A2 (en) | 1994-08-12 | 1996-02-22 | Myriad Genetics, Inc. | IN VIVO MUTATIONS AND POLYMORPHISMS IN THE 17q-LINKED BREAST AND OVARIAN CANCER SUSCEPTIBILITY GENE |
| KR100804564B1 (ko) | 2000-10-30 | 2008-02-20 | 쿠도스 파마슈티칼스 리미티드 | 프탈라지논 유도체 |
| EP1397350B1 (en) | 2001-05-08 | 2007-02-28 | Kudos Pharmaceuticals Limited | Isoquinolinone derivatives as parp inhibitors |
| EP1477175B1 (en) * | 2002-02-19 | 2011-04-27 | Ono Pharmaceutical Co., Ltd. | Fused pyridazine derivative compounds and drugs containing the compounds as the active ingredient |
| ES2357057T3 (es) | 2002-04-30 | 2011-04-15 | Kudos Pharmaceuticals Limited | Derivados de ftalazinona. |
| KR101146806B1 (ko) * | 2003-03-12 | 2012-05-22 | 메이브릿지 리미티드 | 프탈라지논 유도체 |
| US7449464B2 (en) * | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| MXPA06009701A (es) | 2004-02-26 | 2007-03-26 | Inotek Pharmaceuticals Corp | Derivados de isoquinolina y metodos de uso de los mismos. |
| WO2006021801A1 (en) | 2004-08-26 | 2006-03-02 | Kudos Pharmaceuticals Limited | 4-heteroarylmethyl substituted phthalazinone derivatives |
| GB0615809D0 (en) | 2006-08-09 | 2006-09-20 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| KR101563103B1 (ko) | 2006-12-13 | 2015-10-23 | 아스카 세이야쿠 가부시키가이샤 | 퀴녹살린 유도체 |
| CN101616919B (zh) | 2006-12-28 | 2012-10-10 | 雅培制药有限公司 | 聚（adp核糖）聚合酶抑制剂 |
-
2007
- 2007-05-29 EP EP07733721A patent/EP2032140A1/en not_active Withdrawn
- 2007-05-29 JP JP2009512682A patent/JP5271897B2/ja not_active Expired - Fee Related
- 2007-05-29 WO PCT/GB2007/050300 patent/WO2007138355A1/en not_active Ceased
- 2007-05-29 AU AU2007266840A patent/AU2007266840B2/en not_active Ceased
- 2007-05-29 US US12/227,501 patent/US7834015B2/en not_active Expired - Fee Related
- 2007-05-29 CA CA002652167A patent/CA2652167A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007266840A1 (en) | 2007-12-06 |
| AU2007266840B2 (en) | 2012-09-20 |
| US7834015B2 (en) | 2010-11-16 |
| JP2009538897A (ja) | 2009-11-12 |
| WO2007138355A1 (en) | 2007-12-06 |
| US20090209523A1 (en) | 2009-08-20 |
| CA2652167A1 (en) | 2007-12-06 |
| EP2032140A1 (en) | 2009-03-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5271897B2 (ja) | ポリ（ＡＤＰ−リボース）ポリメラーゼ（ＰＡＲＰ）の阻害剤としての、ピロロ［１，２−ａ］ピラジン−１（２Ｈ）−オン及びピロロ［１，２−ｄ］［１，２，４］トリアジン−１（２Ｈ）−オン誘導体 | |
| JP5351755B2 (ja) | ポリ（ａｄｐ−リボース）ポリメラーゼ（ｐａｒｐ）インヒビターとしてのピリジノン及びピリダジノン誘導体 | |
| JP4611441B2 (ja) | ポリ（ａｄｐ−リボース）ポリメラーゼ（ｐａｒｐ）阻害剤としてのアミド置換インダゾール及びベンゾトリアゾール誘導体 | |
| CN101415686B (zh) | 作为聚(adp-核糖)聚合酶(parp)抑制剂的酰胺取代的吲唑和苯并三唑衍生物 | |
| US8362030B2 (en) | Tricyclic derivatives as inhibitors of poly(ADP-ribose) polymerase (PARP) | |
| US20100173895A1 (en) | Imidazolopyrimidines and imidazolotriazine derivatives as inhibitors of poly(adp-ribose)polymerase(parp) | |
| RU2472782C2 (ru) | Производные пиридинона и пиридазинона в качестве ингибиторов поли(adp-рибоза) полимеразы (parp) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20090827 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20090827 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100518 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100518 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20120221 |
|
| RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20120314 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20120918 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120925 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20121219 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20121227 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130319 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130416 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130513 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |