JP5448818B2 - アザベンゾフラニル化合物および使用方法 - Google Patents

Info

Publication number

JP5448818B2

JP5448818B2 JP2009525720A JP2009525720A JP5448818B2 JP 5448818 B2 JP5448818 B2 JP 5448818B2 JP 2009525720 A JP2009525720 A JP 2009525720A JP 2009525720 A JP2009525720 A JP 2009525720A JP 5448818 B2 JP5448818 B2 JP 5448818B2

Authority

JP

Japan

Prior art keywords

pyridine

fluoro

furo

phenylamino

carboxylic acid

Prior art date

2006-08-21

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

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims description 343
• 238000000034 method Methods 0.000 title description 154
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 342
• -1 2,2-dimethyl-1,3-dioxolanyl Chemical group 0.000 claims description 100
• 125000000217 alkyl group Chemical group 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 125000005843 halogen group Chemical group 0.000 claims description 35
• 241000124008 Mammalia Species 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 23
• 208000035475 disorder Diseases 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 230000002159 abnormal effect Effects 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 239000002246 antineoplastic agent Substances 0.000 claims description 12
• 230000010261 cell growth Effects 0.000 claims description 12
• 229940127089 cytotoxic agent Drugs 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 230000003463 hyperproliferative effect Effects 0.000 claims description 9
• 208000027866 inflammatory disease Diseases 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 230000002062 proliferating effect Effects 0.000 claims description 8
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 7
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
• 230000003176 fibrotic effect Effects 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 208000017169 kidney disease Diseases 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 208000023275 Autoimmune disease Diseases 0.000 claims description 3
• 208000020084 Bone disease Diseases 0.000 claims description 3
• 206010033645 Pancreatitis Diseases 0.000 claims description 3
• 125000002393 azetidinyl group Chemical group 0.000 claims description 3
• 230000001066 destructive effect Effects 0.000 claims description 3
• 230000004770 neurodegeneration Effects 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 230000003612 virological effect Effects 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 208000015181 infectious disease Diseases 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims 3
• ZNGLPDOTLBLTIX-SECBINFHSA-N 7-chloro-n-[(2r)-2,3-dihydroxypropoxy]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=C(Cl)C=NC=C2C=1NC1=CC=C(I)C=C1F ZNGLPDOTLBLTIX-SECBINFHSA-N 0.000 claims 2
• AREKJPKIPLDVQY-UHFFFAOYSA-N 7-fluoro-3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=C(F)C=NC=C2C=1NC1=CC=C(I)C=C1F AREKJPKIPLDVQY-UHFFFAOYSA-N 0.000 claims 2
• MOKOPMFVODBALH-SNVBAGLBSA-N n-[(2r)-2,3-dihydroxypropoxy]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F MOKOPMFVODBALH-SNVBAGLBSA-N 0.000 claims 2
• 125000005976 1-phenylethyloxy group Chemical group 0.000 claims 1
• HIXYMKKKJVOWOY-MRVPVSSYSA-N 3-(2,5-difluoro-4-iodoanilino)-n-[(2r)-2,3-dihydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC(F)=C(I)C=C1F HIXYMKKKJVOWOY-MRVPVSSYSA-N 0.000 claims 1
• YOTPJQSYYZLQTK-SECBINFHSA-N 3-(2,6-difluoro-4-iodoanilino)-n-[(2r)-2,3-dihydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=C(F)C=C(I)C=C1F YOTPJQSYYZLQTK-SECBINFHSA-N 0.000 claims 1
• NSUHKSDBHFLPTJ-SNVBAGLBSA-N 3-(2-chloro-4-iodoanilino)-n-[(2r)-2,3-dihydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1Cl NSUHKSDBHFLPTJ-SNVBAGLBSA-N 0.000 claims 1
• ZSVBLZJTOHYBFS-UHFFFAOYSA-N 3-(2-fluoro-4-iodo-n-methylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC=C2C=1N(C)C1=CC=C(I)C=C1F ZSVBLZJTOHYBFS-UHFFFAOYSA-N 0.000 claims 1
• XCCBPYPWIAZDAS-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(1-hydroxypropan-2-yloxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCC(C)ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F XCCBPYPWIAZDAS-UHFFFAOYSA-N 0.000 claims 1
• ZASFNBPGAMDLGQ-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(1-methylpiperidin-4-yl)oxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound C1CN(C)CCC1ONC(=O)C1=C(NC=2C(=CC(I)=CC=2)F)C2=CN=CC=C2O1 ZASFNBPGAMDLGQ-UHFFFAOYSA-N 0.000 claims 1
• YXSFFGDHEKCEFI-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(1h-imidazol-5-ylmethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCC=2NC=NC=2)OC2=CC=NC=C12 YXSFFGDHEKCEFI-UHFFFAOYSA-N 0.000 claims 1
• BRHYIGCVKINWRY-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-4-methylfuro[3,2-c]pyridine-2-carboxamide Chemical compound C1=2C(C)=NC=CC=2OC(C(=O)NOCCO)=C1NC1=CC=C(I)C=C1F BRHYIGCVKINWRY-UHFFFAOYSA-N 0.000 claims 1
• HJPVQFUUZVDHQC-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-7-phenylfuro[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=C(C=3C=CC=CC=3)C=NC=C2C=1NC1=CC=C(I)C=C1F HJPVQFUUZVDHQC-UHFFFAOYSA-N 0.000 claims 1
• OWQKOFHCOAAMTL-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-n-methylfuro[3,2-c]pyridine-2-carboxamide Chemical compound OCCON(C)C(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F OWQKOFHCOAAMTL-UHFFFAOYSA-N 0.000 claims 1
• LVHMCPRJISQGAK-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F LVHMCPRJISQGAK-UHFFFAOYSA-N 0.000 claims 1
• KQFHBRNOZGXYQF-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxypropoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound CC(O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F KQFHBRNOZGXYQF-UHFFFAOYSA-N 0.000 claims 1
• YMNVIHJYFYSIHE-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-methylpropoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound CC(C)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F YMNVIHJYFYSIHE-UHFFFAOYSA-N 0.000 claims 1
• BIQWLTRWWSVHFH-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-morpholin-4-ylethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCCN2CCOCC2)OC2=CC=NC=C12 BIQWLTRWWSVHFH-UHFFFAOYSA-N 0.000 claims 1
• YHQVEEYIFZLAAL-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-piperidin-1-ylethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCCN2CCCCC2)OC2=CC=NC=C12 YHQVEEYIFZLAAL-UHFFFAOYSA-N 0.000 claims 1
• CWSIFJGKWFWQAR-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(oxan-4-yloxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOC2CCOCC2)OC2=CC=NC=C12 CWSIFJGKWFWQAR-UHFFFAOYSA-N 0.000 claims 1
• KQFHBRNOZGXYQF-SECBINFHSA-N 3-(2-fluoro-4-iodoanilino)-n-[(2r)-2-hydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound C[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F KQFHBRNOZGXYQF-SECBINFHSA-N 0.000 claims 1
• KQFHBRNOZGXYQF-VIFPVBQESA-N 3-(2-fluoro-4-iodoanilino)-n-[(2s)-2-hydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound C[C@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F KQFHBRNOZGXYQF-VIFPVBQESA-N 0.000 claims 1
• AJZFZFIDJMYVGI-MERQFXBCSA-N 3-(2-fluoro-4-iodoanilino)-n-[(3s)-pyrrolidin-3-yl]oxyfuro[3,2-c]pyridine-2-carboxamide;formic acid Chemical compound OC=O.FC1=CC(I)=CC=C1NC1=C(C(=O)NO[C@@H]2CNCC2)OC2=CC=NC=C12 AJZFZFIDJMYVGI-MERQFXBCSA-N 0.000 claims 1
• RILXIUKJZTVWOR-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-[2-(2-oxopyrrolidin-1-yl)ethoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCCN2C(CCC2)=O)OC2=CC=NC=C12 RILXIUKJZTVWOR-UHFFFAOYSA-N 0.000 claims 1
• JOSPHXYARVDBKV-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-[2-(methanesulfonamido)ethoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound CS(=O)(=O)NCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F JOSPHXYARVDBKV-UHFFFAOYSA-N 0.000 claims 1
• GXPHNPWQZJWDIE-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-[2-(methylamino)ethoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound CNCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F GXPHNPWQZJWDIE-UHFFFAOYSA-N 0.000 claims 1
• GPXSOWYDMXOJSA-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-hydroxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F GPXSOWYDMXOJSA-UHFFFAOYSA-N 0.000 claims 1
• NLSWTNSYKVDGOT-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-methoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F NLSWTNSYKVDGOT-UHFFFAOYSA-N 0.000 claims 1
• IQXHJWQCHIFPOH-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-phenoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOC=2C=CC=CC=2)OC2=CC=NC=C12 IQXHJWQCHIFPOH-UHFFFAOYSA-N 0.000 claims 1
• YYSYZXLKBHAFQP-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-phenylmethoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCC=2C=CC=CC=2)OC2=CC=NC=C12 YYSYZXLKBHAFQP-UHFFFAOYSA-N 0.000 claims 1
• PYVXSCSFCDZMET-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-piperidin-4-yloxyfuro[3,2-c]pyridine-2-carboxamide;formic acid Chemical compound OC=O.FC1=CC(I)=CC=C1NC1=C(C(=O)NOC2CCNCC2)OC2=CC=NC=C12 PYVXSCSFCDZMET-UHFFFAOYSA-N 0.000 claims 1
• WDYKHMRALAELNL-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-propan-2-yloxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound CC(C)ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F WDYKHMRALAELNL-UHFFFAOYSA-N 0.000 claims 1
• GYCNBDSPAUCLMY-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-propoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound CCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F GYCNBDSPAUCLMY-UHFFFAOYSA-N 0.000 claims 1
• IDPRSJFPZKEETI-UHFFFAOYSA-N 3-(2-fluoro-4-methoxyanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC1=C(C(=O)NOCCO)OC2=CC=NC=C12 IDPRSJFPZKEETI-UHFFFAOYSA-N 0.000 claims 1
• YMYLFFXZIBNVOX-UHFFFAOYSA-N 3-(2-fluoro-4-methylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(C)=CC=C1NC1=C(C(=O)NOCCO)OC2=CC=NC=C12 YMYLFFXZIBNVOX-UHFFFAOYSA-N 0.000 claims 1
• XRJBBHQHSPVSSV-UHFFFAOYSA-N 3-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)OC2=CC=NC=C12 XRJBBHQHSPVSSV-UHFFFAOYSA-N 0.000 claims 1
• MBDVAIXTFKWSIQ-UHFFFAOYSA-N 3-(4-bromo-2-chloroanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(Br)C=C1Cl MBDVAIXTFKWSIQ-UHFFFAOYSA-N 0.000 claims 1
• KFCJJPYOSOKYOC-SNVBAGLBSA-N 3-(4-bromo-2-fluoroanilino)-n-[(2r)-2,3-dihydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(Br)C=C1F KFCJJPYOSOKYOC-SNVBAGLBSA-N 0.000 claims 1
• ZHAATOXXOFJKOI-UHFFFAOYSA-N 4-chloro-3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC(Cl)=C2C=1NC1=CC=C(I)C=C1F ZHAATOXXOFJKOI-UHFFFAOYSA-N 0.000 claims 1
• DBCSLIDHWJMBTA-SECBINFHSA-N 7-bromo-n-[(2r)-2,3-dihydroxypropoxy]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=C(Br)C=NC=C2C=1NC1=CC=C(I)C=C1F DBCSLIDHWJMBTA-SECBINFHSA-N 0.000 claims 1
• BLTCPZNAPZCEHZ-UHFFFAOYSA-N 7-chloro-3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=C(Cl)C=NC=C2C=1NC1=CC=C(I)C=C1F BLTCPZNAPZCEHZ-UHFFFAOYSA-N 0.000 claims 1
• MXTXYFYQDUYXJL-JTQLQIEISA-N 7-chloro-3-(2-fluoro-4-iodoanilino)-n-[(3s)-pyrrolidin-3-yl]oxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NO[C@@H]2CNCC2)OC2=C(Cl)C=NC=C12 MXTXYFYQDUYXJL-JTQLQIEISA-N 0.000 claims 1
• GHRBIPYIAHXFCH-UHFFFAOYSA-N 7-chloro-3-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)OC2=C(Cl)C=NC=C12 GHRBIPYIAHXFCH-UHFFFAOYSA-N 0.000 claims 1
• RZJMBERNOWZWPE-UHFFFAOYSA-N 7-cyano-3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=C(C#N)C=NC=C2C=1NC1=CC=C(I)C=C1F RZJMBERNOWZWPE-UHFFFAOYSA-N 0.000 claims 1
• KTCIDTVOVGOCMK-UHFFFAOYSA-N 7-fluoro-3-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)OC2=C(F)C=NC=C12 KTCIDTVOVGOCMK-UHFFFAOYSA-N 0.000 claims 1
• SEEBPOKQKKFAJK-UHFFFAOYSA-N C(=O)O.N1CC(CCC1)ONC(=O)C1=C(C=2C=NC=CC2O1)NC1=C(C=C(C=C1)I)F Chemical compound C(=O)O.N1CC(CCC1)ONC(=O)C1=C(C=2C=NC=CC2O1)NC1=C(C=C(C=C1)I)F SEEBPOKQKKFAJK-UHFFFAOYSA-N 0.000 claims 1
• ZEZHPEIEEFTILY-QMMMGPOBSA-N G-573 Chemical compound C[C@H](O)CONC(=O)C=1OC2=C(F)C=NC=C2C=1NC1=CC=C(I)C=C1F ZEZHPEIEEFTILY-QMMMGPOBSA-N 0.000 claims 1
• GOYLXWIEDLPDLQ-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yloxy)-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCC(CO)ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F GOYLXWIEDLPDLQ-UHFFFAOYSA-N 0.000 claims 1
• UNYVYIUFNWQXAD-UHFFFAOYSA-N n-(2-aminoethoxy)-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound NCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F UNYVYIUFNWQXAD-UHFFFAOYSA-N 0.000 claims 1
• HFYFOAKWXBVMDY-GFCCVEGCSA-N n-[(2r)-2,3-dihydroxypropoxy]-3-(4-ethynyl-2-fluoroanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(C#C)C=C1F HFYFOAKWXBVMDY-GFCCVEGCSA-N 0.000 claims 1
• KNOYKCKVZWXKDQ-GFCCVEGCSA-N n-[(2r)-2,3-dihydroxypropoxy]-3-(4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1 KNOYKCKVZWXKDQ-GFCCVEGCSA-N 0.000 claims 1
• DAHUPKFQCHIVJO-UHFFFAOYSA-N n-[2-(dimethylamino)ethoxy]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound CN(C)CCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F DAHUPKFQCHIVJO-UHFFFAOYSA-N 0.000 claims 1
• WUNZFKVZZZPIKW-UHFFFAOYSA-N n-ethoxy-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound CCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F WUNZFKVZZZPIKW-UHFFFAOYSA-N 0.000 claims 1
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 348
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 339
• 239000000243 solution Substances 0.000 description 155
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 132
• 235000019439 ethyl acetate Nutrition 0.000 description 121
• 239000000203 mixture Substances 0.000 description 120
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 117
• 239000007787 solid Substances 0.000 description 115
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
• 239000011541 reaction mixture Substances 0.000 description 92
• 239000002904 solvent Substances 0.000 description 92
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 85
• 238000006243 chemical reaction Methods 0.000 description 82
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 82
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
• 238000003818 flash chromatography Methods 0.000 description 72
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 65
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 55
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 53
• 239000012044 organic layer Substances 0.000 description 50
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 50
• 239000003921 oil Substances 0.000 description 46
• 235000019198 oils Nutrition 0.000 description 46
• 239000012267 brine Substances 0.000 description 45
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 45
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 43
• 238000010992 reflux Methods 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 38
• 239000010410 layer Substances 0.000 description 38
• 210000004027 cell Anatomy 0.000 description 36
• 239000000706 filtrate Substances 0.000 description 36
• 238000005160 1H NMR spectroscopy Methods 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 235000019441 ethanol Nutrition 0.000 description 32
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 32
• 235000019341 magnesium sulphate Nutrition 0.000 description 32
• 125000000623 heterocyclic group Chemical group 0.000 description 30
• 238000000746 purification Methods 0.000 description 30
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 29
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
• 239000002585 base Substances 0.000 description 27
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 26
• 206010028980 Neoplasm Diseases 0.000 description 26
• 238000011282 treatment Methods 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
• 239000002244 precipitate Substances 0.000 description 23
• 230000002829 reductive effect Effects 0.000 description 23
• 238000003756 stirring Methods 0.000 description 23
• 238000005481 NMR spectroscopy Methods 0.000 description 22
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 22
• 239000000725 suspension Substances 0.000 description 22
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
• 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 21
• 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 21
• 239000012230 colorless oil Substances 0.000 description 21
• IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
• 229940002612 prodrug Drugs 0.000 description 19
• 239000000651 prodrug Substances 0.000 description 19
• 239000011734 sodium Substances 0.000 description 19
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 19
• 229960000583 acetic acid Drugs 0.000 description 18
• 238000003556 assay Methods 0.000 description 18
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 17
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• 239000002253 acid Substances 0.000 description 17
• 239000012312 sodium hydride Substances 0.000 description 17
• 229910000104 sodium hydride Inorganic materials 0.000 description 17
• 239000012453 solvate Substances 0.000 description 17
• QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 16
• 201000011510 cancer Diseases 0.000 description 16
• 229910052740 iodine Inorganic materials 0.000 description 16
• 229910052938 sodium sulfate Inorganic materials 0.000 description 16
• 235000011152 sodium sulphate Nutrition 0.000 description 16
• 125000001072 heteroaryl group Chemical group 0.000 description 15
• 239000012299 nitrogen atmosphere Substances 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 150000001412 amines Chemical class 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 14
• 125000001424 substituent group Chemical group 0.000 description 14
• 239000000758 substrate Substances 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• 239000000377 silicon dioxide Substances 0.000 description 13
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 229910052786 argon Inorganic materials 0.000 description 12
• 125000004452 carbocyclyl group Chemical group 0.000 description 12
• ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 12
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 12
• 230000004913 activation Effects 0.000 description 11
• 239000000284 extract Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
• HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 10
• 239000000741 silica gel Substances 0.000 description 10
• 229910002027 silica gel Inorganic materials 0.000 description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
• 102000043136 MAP kinase family Human genes 0.000 description 9
• 108091054455 MAP kinase family Proteins 0.000 description 9
• 208000002193 Pain Diseases 0.000 description 9
• 229910004298 SiO 2 Inorganic materials 0.000 description 9
• 108010004469 allophycocyanin Proteins 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• 239000006185 dispersion Substances 0.000 description 9
• 239000002480 mineral oil Substances 0.000 description 9
• 235000010446 mineral oil Nutrition 0.000 description 9
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
• 239000012047 saturated solution Substances 0.000 description 9
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 8
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 description 8
• 102000019149 MAP kinase activity proteins Human genes 0.000 description 8
• 108040008097 MAP kinase activity proteins Proteins 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
• 239000012298 atmosphere Substances 0.000 description 8
• 229940079593 drug Drugs 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 230000037361 pathway Effects 0.000 description 8
• 230000026731 phosphorylation Effects 0.000 description 8
• 238000006366 phosphorylation reaction Methods 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• 238000006722 reduction reaction Methods 0.000 description 8
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
• 235000019345 sodium thiosulphate Nutrition 0.000 description 8
• JRHPOFJADXHYBR-HTQZYQBOSA-N (1r,2r)-1-n,2-n-dimethylcyclohexane-1,2-diamine Chemical compound CN[C@@H]1CCCC[C@H]1NC JRHPOFJADXHYBR-HTQZYQBOSA-N 0.000 description 7
• SRIRADNHFQTPFR-UHFFFAOYSA-N 2-fluoro-4-trimethylsilylaniline Chemical compound C[Si](C)(C)C1=CC=C(N)C(F)=C1 SRIRADNHFQTPFR-UHFFFAOYSA-N 0.000 description 7
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 7
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
• 229940124647 MEK inhibitor Drugs 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 7
• 238000002474 experimental method Methods 0.000 description 7
• 229910000160 potassium phosphate Inorganic materials 0.000 description 7
• 235000011009 potassium phosphates Nutrition 0.000 description 7
• 230000008569 process Effects 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 238000010898 silica gel chromatography Methods 0.000 description 7
• 235000009518 sodium iodide Nutrition 0.000 description 7
• 239000000126 substance Substances 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 239000008346 aqueous phase Substances 0.000 description 6
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
• 238000010828 elution Methods 0.000 description 6
• FYCXHESHLFYDAO-UHFFFAOYSA-N ethyl 3-aminofuro[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(N)=C(C(=O)OCC)OC2=C1 FYCXHESHLFYDAO-UHFFFAOYSA-N 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 239000003112 inhibitor Substances 0.000 description 6
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 6
• 230000035772 mutation Effects 0.000 description 6
• 210000000056 organ Anatomy 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 6
• 125000006413 ring segment Chemical group 0.000 description 6
• DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
• 206010009944 Colon cancer Diseases 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• 206010019280 Heart failures Diseases 0.000 description 5
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
• 102000001291 MAP Kinase Kinase Kinase Human genes 0.000 description 5
• 108060006687 MAP kinase kinase kinase Proteins 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
• 229910000024 caesium carbonate Inorganic materials 0.000 description 5
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
• ZVCKHSPPUCNIIW-UHFFFAOYSA-N ethyl 3-(trifluoromethylsulfonyloxy)furo[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(OS(=O)(=O)C(F)(F)F)=C(C(=O)OCC)OC2=C1 ZVCKHSPPUCNIIW-UHFFFAOYSA-N 0.000 description 5
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
• 239000012065 filter cake Substances 0.000 description 5
• 230000012010 growth Effects 0.000 description 5
• 230000005764 inhibitory process Effects 0.000 description 5
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
• 210000004072 lung Anatomy 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 239000002207 metabolite Substances 0.000 description 5
• 229910052751 metal Inorganic materials 0.000 description 5
• 239000002184 metal Substances 0.000 description 5
• 108090000623 proteins and genes Proteins 0.000 description 5
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
• 229940124597 therapeutic agent Drugs 0.000 description 5
• 238000012546 transfer Methods 0.000 description 5
• 229940062627 tribasic potassium phosphate Drugs 0.000 description 5
• WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 4
• SUZAIHLOLUYRJG-UHFFFAOYSA-N 1-bromo-2-fluoro-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(Br)C(F)=C1 SUZAIHLOLUYRJG-UHFFFAOYSA-N 0.000 description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
• 206010007559 Cardiac failure congestive Diseases 0.000 description 4
• 241000701022 Cytomegalovirus Species 0.000 description 4
• 208000002249 Diabetes Complications Diseases 0.000 description 4
• 101000876610 Dictyostelium discoideum Extracellular signal-regulated kinase 2 Proteins 0.000 description 4
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 4
• 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 4
• 241000588724 Escherichia coli Species 0.000 description 4
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 4
• 241000282412 Homo Species 0.000 description 4
• 101001052493 Homo sapiens Mitogen-activated protein kinase 1 Proteins 0.000 description 4
• 241000701044 Human gammaherpesvirus 4 Species 0.000 description 4
• 241000701806 Human papillomavirus Species 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
• 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 4
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
• 239000012828 PI3K inhibitor Substances 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
• 206010052779 Transplant rejections Diseases 0.000 description 4
• 125000003172 aldehyde group Chemical group 0.000 description 4
• 150000001299 aldehydes Chemical class 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 235000011114 ammonium hydroxide Nutrition 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 239000007822 coupling agent Substances 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• JQEBDKPNMXJDEH-UHFFFAOYSA-N ethyl 7-bromo-3-hydroxyfuro[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(O)=C(C(=O)OCC)OC2=C1Br JQEBDKPNMXJDEH-UHFFFAOYSA-N 0.000 description 4
• YEOIHKISLYUZEQ-UHFFFAOYSA-N ethyl 7-fluoro-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(F)C=NC=C2C=1NC1=CC=C(I)C=C1F YEOIHKISLYUZEQ-UHFFFAOYSA-N 0.000 description 4
• 229960002949 fluorouracil Drugs 0.000 description 4
• OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 4
• 235000019253 formic acid Nutrition 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 239000011521 glass Substances 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 150000002500 ions Chemical class 0.000 description 4
• 210000003734 kidney Anatomy 0.000 description 4
• 229940043355 kinase inhibitor Drugs 0.000 description 4
• HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 4
• 239000003446 ligand Substances 0.000 description 4
• 150000002632 lipids Chemical class 0.000 description 4
• 239000002609 medium Substances 0.000 description 4
• 229960000485 methotrexate Drugs 0.000 description 4
• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 4
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
• 239000012074 organic phase Substances 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 239000000546 pharmaceutical excipient Substances 0.000 description 4
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
• 235000018102 proteins Nutrition 0.000 description 4
• 102000004169 proteins and genes Human genes 0.000 description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 150000003335 secondary amines Chemical class 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 208000024891 symptom Diseases 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
• 238000005406 washing Methods 0.000 description 4
• JLDHXHPQMBNKMC-RQJHMYQMSA-N (2s,3r)-3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](O)[C@H]1C(O)=O JLDHXHPQMBNKMC-RQJHMYQMSA-N 0.000 description 3
• AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
• ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 3
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
• GZRMNMGWNKSANY-UHFFFAOYSA-N 4-bromo-2-fluoroaniline Chemical compound NC1=CC=C(Br)C=C1F GZRMNMGWNKSANY-UHFFFAOYSA-N 0.000 description 3
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
• 208000000094 Chronic Pain Diseases 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 3
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
• 108010008165 Etanercept Proteins 0.000 description 3
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
• 239000007821 HATU Substances 0.000 description 3
• 241000238631 Hexapoda Species 0.000 description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
• 206010061218 Inflammation Diseases 0.000 description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 description 3
• 239000002841 Lewis acid Substances 0.000 description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 3
• 229910019142 PO4 Inorganic materials 0.000 description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 230000010933 acylation Effects 0.000 description 3
• 238000005917 acylation reaction Methods 0.000 description 3
• 125000003158 alcohol group Chemical group 0.000 description 3
• 230000029936 alkylation Effects 0.000 description 3
• 238000005804 alkylation reaction Methods 0.000 description 3
• 125000003277 amino group Chemical group 0.000 description 3
• 230000003110 anti-inflammatory effect Effects 0.000 description 3
• 239000012131 assay buffer Substances 0.000 description 3
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
• 239000004305 biphenyl Substances 0.000 description 3
• 235000010290 biphenyl Nutrition 0.000 description 3
• 238000001516 cell proliferation assay Methods 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• 229940001468 citrate Drugs 0.000 description 3
• 208000029742 colonic neoplasm Diseases 0.000 description 3
• 230000008878 coupling Effects 0.000 description 3
• 238000010168 coupling process Methods 0.000 description 3
• 238000005859 coupling reaction Methods 0.000 description 3
• 125000004093 cyano group Chemical group *C#N 0.000 description 3
• 231100000433 cytotoxic Toxicity 0.000 description 3
• 230000001472 cytotoxic effect Effects 0.000 description 3
• 206010012601 diabetes mellitus Diseases 0.000 description 3
• KTLADQLSXYYOMO-UHFFFAOYSA-N ethyl 3-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyloxy)furo[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=C(C(=O)OCC)OC2=C1 KTLADQLSXYYOMO-UHFFFAOYSA-N 0.000 description 3
• MGAYCAFTAPAJQS-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-methylsulfanylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(SC)C=C1F MGAYCAFTAPAJQS-UHFFFAOYSA-N 0.000 description 3
• JEMNTJDZZSQHDV-UHFFFAOYSA-N ethyl 3-(4-bromo-2-chloroanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(Br)C=C1Cl JEMNTJDZZSQHDV-UHFFFAOYSA-N 0.000 description 3
• NRNFODFYWKTHKW-UHFFFAOYSA-N ethyl 3-amino-7-chlorofuro[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(N)=C(C(=O)OCC)OC2=C1Cl NRNFODFYWKTHKW-UHFFFAOYSA-N 0.000 description 3
• BHODOJGSGCTSTC-UHFFFAOYSA-N ethyl 3-amino-7-fluorofuro[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(N)=C(C(=O)OCC)OC2=C1F BHODOJGSGCTSTC-UHFFFAOYSA-N 0.000 description 3
• PLNBDPQVBXHQAC-UHFFFAOYSA-N ethyl 3-hydroxyfuro[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(O)=C(C(=O)OCC)OC2=C1 PLNBDPQVBXHQAC-UHFFFAOYSA-N 0.000 description 3
• PNTLRQVAWYIEKL-UHFFFAOYSA-N ethyl 4,5-dibromopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(Br)=C1Br PNTLRQVAWYIEKL-UHFFFAOYSA-N 0.000 description 3
• HKQZTHJGZCHBQZ-UHFFFAOYSA-N ethyl 4-chloro-3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC(Cl)=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F HKQZTHJGZCHBQZ-UHFFFAOYSA-N 0.000 description 3
• LLGMGBPYKVYQSO-UHFFFAOYSA-N ethyl 7-bromo-3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(Br)C=NC=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F LLGMGBPYKVYQSO-UHFFFAOYSA-N 0.000 description 3
• WUFBISPGAWRBDT-UHFFFAOYSA-N ethyl 7-chloro-3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(Cl)C=NC=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F WUFBISPGAWRBDT-UHFFFAOYSA-N 0.000 description 3
• OADMIBKWTJUNDN-UHFFFAOYSA-N ethyl 7-fluoro-3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(F)C=NC=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F OADMIBKWTJUNDN-UHFFFAOYSA-N 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
• GWQVMPWSEVRGPY-UHFFFAOYSA-N europium cryptate Chemical compound [Eu+3].N=1C2=CC=CC=1CN(CC=1N=C(C=CC=1)C=1N=C(C3)C=CC=1)CC(N=1)=CC(C(=O)NCCN)=CC=1C(N=1)=CC(C(=O)NCCN)=CC=1CN3CC1=CC=CC2=N1 GWQVMPWSEVRGPY-UHFFFAOYSA-N 0.000 description 3
• 230000005284 excitation Effects 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 230000014509 gene expression Effects 0.000 description 3
• 230000002140 halogenating effect Effects 0.000 description 3
• 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 3
• 150000002430 hydrocarbons Chemical group 0.000 description 3
• 150000002443 hydroxylamines Chemical class 0.000 description 3
• 238000000338 in vitro Methods 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• 238000011065 in-situ storage Methods 0.000 description 3
• 230000004054 inflammatory process Effects 0.000 description 3
• 229910052742 iron Inorganic materials 0.000 description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 description 3
• 150000007517 lewis acids Chemical class 0.000 description 3
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 3
• 210000004962 mammalian cell Anatomy 0.000 description 3
• 239000011159 matrix material Substances 0.000 description 3
• 201000001441 melanoma Diseases 0.000 description 3
• 229960001428 mercaptopurine Drugs 0.000 description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 208000004296 neuralgia Diseases 0.000 description 3
• 208000021722 neuropathic pain Diseases 0.000 description 3
• 210000004940 nucleus Anatomy 0.000 description 3
• XZTSFVPMMQNIAJ-UHFFFAOYSA-N o-(2-ethenoxyethyl)hydroxylamine Chemical compound NOCCOC=C XZTSFVPMMQNIAJ-UHFFFAOYSA-N 0.000 description 3
• QFRHQZLHZLSOHJ-UHFFFAOYSA-N o-(pyridin-2-ylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=CC=N1 QFRHQZLHZLSOHJ-UHFFFAOYSA-N 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 230000002018 overexpression Effects 0.000 description 3
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
• 230000001575 pathological effect Effects 0.000 description 3
• LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 3
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
• 239000010452 phosphate Substances 0.000 description 3
• UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 3
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
• 150000003141 primary amines Chemical class 0.000 description 3
• 235000013772 propylene glycol Nutrition 0.000 description 3
• 229960004063 propylene glycol Drugs 0.000 description 3
• 230000005855 radiation Effects 0.000 description 3
• HXCHCVDVKSCDHU-PJKCJEBCSA-N s-[(2r,3s,4s,6s)-6-[[(2r,3s,4s,5r,6r)-5-[(2s,4s,5s)-5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[(2s,5z,9r,13e)-9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-m Chemical compound C1[C@H](OC)[C@@H](NCC)CO[C@H]1O[C@H]1[C@H](O[C@@H]2C\3=C(NC(=O)OC)C(=O)C[C@@](C/3=C/CSSSC)(O)C#C\C=C/C#C2)O[C@H](C)[C@@H](NO[C@@H]2O[C@H](C)[C@@H](SC(=O)C=3C(=C(OC)C(O[C@H]4[C@@H]([C@H](OC)[C@@H](O)[C@H](C)O4)O)=C(I)C=3C)OC)[C@@H](O)C2)[C@@H]1O HXCHCVDVKSCDHU-PJKCJEBCSA-N 0.000 description 3
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](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 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 3
• 206010041823 squamous cell carcinoma Diseases 0.000 description 3
• WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 description 3
• 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 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
• 230000001225 therapeutic effect Effects 0.000 description 3
• TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 3
• JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 3
• 230000009385 viral infection Effects 0.000 description 3
• 239000003039 volatile agent Substances 0.000 description 3
• PWZIBVWIAKQRMS-UHFFFAOYSA-N (2-fluoro-4-trimethylsilylphenyl) trifluoromethanesulfonate Chemical compound C[Si](C)(C)C1=CC=C(OS(=O)(=O)C(F)(F)F)C(F)=C1 PWZIBVWIAKQRMS-UHFFFAOYSA-N 0.000 description 2
• QOJCEWYVJOLFHN-TYSVMGFPSA-N (2r,3r)-2-(hydroxymethyl)pyrrolidin-3-ol;hydrochloride Chemical compound Cl.OC[C@H]1NCC[C@H]1O QOJCEWYVJOLFHN-TYSVMGFPSA-N 0.000 description 2
• WWVCWLBEARZMAH-GHMZBOCLSA-N (2r,4r)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound C1[C@H](O)C[C@H](C(O)=O)N1C(=O)OCC1=CC=CC=C1 WWVCWLBEARZMAH-GHMZBOCLSA-N 0.000 description 2
• HHDQVBSXYDRQGD-QWWZWVQMSA-N (2r,4r)-4-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound O[C@@H]1C[C@H](C(O)=O)N(C(O)=O)C1 HHDQVBSXYDRQGD-QWWZWVQMSA-N 0.000 description 2
• XBSYFWFTVVETPJ-UHFFFAOYSA-N (3-fluoro-4-nitrophenyl)-trimethylsilane Chemical compound C[Si](C)(C)C1=CC=C([N+]([O-])=O)C(F)=C1 XBSYFWFTVVETPJ-UHFFFAOYSA-N 0.000 description 2
• IZBMPGFJNIDMRR-RKDXNWHRSA-N (3r,4r)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione Chemical compound O=C1[C@H](O)[C@@H](O)C(=O)N1CC1=CC=CC=C1 IZBMPGFJNIDMRR-RKDXNWHRSA-N 0.000 description 2
• QJRIUWQPJVPYSO-QWRGUYRKSA-N (3s,4s)-1-benzylpyrrolidine-3,4-diol Chemical compound C1[C@H](O)[C@@H](O)CN1CC1=CC=CC=C1 QJRIUWQPJVPYSO-QWRGUYRKSA-N 0.000 description 2
• VADWFRGDDJHKNB-MMALYQPHSA-N (3s,4s)-pyrrolidine-3,4-diol;hydrochloride Chemical compound Cl.O[C@H]1CNC[C@@H]1O VADWFRGDDJHKNB-MMALYQPHSA-N 0.000 description 2
• ZPXGUUJPLNQRCZ-UHFFFAOYSA-N (4-bromo-3-fluorophenyl)methoxy-tri(propan-2-yl)silane Chemical compound CC(C)[Si](C(C)C)(C(C)C)OCC1=CC=C(Br)C(F)=C1 ZPXGUUJPLNQRCZ-UHFFFAOYSA-N 0.000 description 2
• IEXUMDBQLIVNHZ-YOUGDJEHSA-N (8s,11r,13r,14s,17s)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxypropyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(O)CCCO)[C@@]2(C)C1 IEXUMDBQLIVNHZ-YOUGDJEHSA-N 0.000 description 2
• USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 2
• BKTKEYKNTDKDNF-WTDSWWLTSA-N (ne)-n-[(4,5-dichloropyridin-3-yl)methylidene]hydroxylamine Chemical compound O\N=C\C1=CN=CC(Cl)=C1Cl BKTKEYKNTDKDNF-WTDSWWLTSA-N 0.000 description 2
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
• BJDDRAYUVSVPPR-UHFFFAOYSA-N 1-[tert-butyl(dimethyl)silyl]oxypropan-2-ol Chemical compound CC(O)CO[Si](C)(C)C(C)(C)C BJDDRAYUVSVPPR-UHFFFAOYSA-N 0.000 description 2
• ZRONMPPDQBXARP-UHFFFAOYSA-N 1-aminooxy-2-methylpropan-2-ol Chemical compound CC(C)(O)CON ZRONMPPDQBXARP-UHFFFAOYSA-N 0.000 description 2
• XANVIFOBBVAKCY-UHFFFAOYSA-N 1-bromo-2-fluoro-4-methoxybenzene Chemical compound COC1=CC=C(Br)C(F)=C1 XANVIFOBBVAKCY-UHFFFAOYSA-N 0.000 description 2
• GBBSAMQTQCPOBF-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane Chemical compound CB1OB(C)OB(C)O1 GBBSAMQTQCPOBF-UHFFFAOYSA-N 0.000 description 2
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
• QQVBSJGGYUFBKN-UHFFFAOYSA-N 2-(2-aminoethoxy)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(OCCN)C(=O)C2=C1 QQVBSJGGYUFBKN-UHFFFAOYSA-N 0.000 description 2
• MMFMJXXONOZMFK-UHFFFAOYSA-N 2-(2-hydroxy-2-methylpropoxy)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(OCC(C)(O)C)C(=O)C2=C1 MMFMJXXONOZMFK-UHFFFAOYSA-N 0.000 description 2
• UDBWFLHXGSWKQP-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutoxy)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(OCCC(C)(O)C)C(=O)C2=C1 UDBWFLHXGSWKQP-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• ZKBOHEFSABSRIL-UHFFFAOYSA-N 2-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-yloxy]isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(OC(CO[Si](C)(C)C(C)(C)C)C)C(=O)C2=C1 ZKBOHEFSABSRIL-UHFFFAOYSA-N 0.000 description 2
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
• GCUNXHWKISRLSW-UHFFFAOYSA-N 2-[2-[tert-butyl(dimethyl)silyl]oxypropoxy]isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(OCC(C)O[Si](C)(C)C(C)(C)C)C(=O)C2=C1 GCUNXHWKISRLSW-UHFFFAOYSA-N 0.000 description 2
• KFGZXSPFUVKVCA-UHFFFAOYSA-N 2-[[1-(4-methylphenyl)sulfonylimidazol-2-yl]methoxy]isoindole-1,3-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CON2C(C3=CC=CC=C3C2=O)=O)=NC=C1 KFGZXSPFUVKVCA-UHFFFAOYSA-N 0.000 description 2
• FRYOCKYIGKFINL-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxypropan-1-ol Chemical compound OCC(C)O[Si](C)(C)C(C)(C)C FRYOCKYIGKFINL-UHFFFAOYSA-N 0.000 description 2
• INMDOYDAPWNQEW-UHFFFAOYSA-N 2-aminooxy-2-methylpropan-1-ol;hydrochloride Chemical compound Cl.OCC(C)(C)ON INMDOYDAPWNQEW-UHFFFAOYSA-N 0.000 description 2
• 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 2
• 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 2
• RKSKSMBPQYFDKK-UHFFFAOYSA-N 2-o-benzyl 7-o-ethyl 3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-2,7-dicarboxylate Chemical compound C=1C=CC=CC=1COC(=O)C=1OC=2C(C(=O)OCC)=CN=CC=2C=1NC1=CC=C([Si](C)(C)C)C=C1F RKSKSMBPQYFDKK-UHFFFAOYSA-N 0.000 description 2
• KXMCUAJMYHXTEZ-UHFFFAOYSA-N 2-o-benzyl 7-o-ethyl 3-(trifluoromethylsulfonyloxy)furo[3,2-c]pyridine-2,7-dicarboxylate Chemical compound O1C=2C(C(=O)OCC)=CN=CC=2C(OS(=O)(=O)C(F)(F)F)=C1C(=O)OCC1=CC=CC=C1 KXMCUAJMYHXTEZ-UHFFFAOYSA-N 0.000 description 2
• AIMTVYNLIWPNMS-UHFFFAOYSA-N 2-o-benzyl 7-o-ethyl 3-hydroxyfuro[3,2-c]pyridine-2,7-dicarboxylate Chemical compound O1C=2C(C(=O)OCC)=CN=CC=2C(O)=C1C(=O)OCC1=CC=CC=C1 AIMTVYNLIWPNMS-UHFFFAOYSA-N 0.000 description 2
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
• WDIZUNBIUYQBHB-UHFFFAOYSA-N 3,7-dibromo-2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)furo[3,2-c]pyridine Chemical compound CC1(C)COC(C2=C(C3=CN=CC(Br)=C3O2)Br)=N1 WDIZUNBIUYQBHB-UHFFFAOYSA-N 0.000 description 2
• YDHMHSGGBRWVPT-UHFFFAOYSA-N 3,7-dibromo-n-(1-hydroxy-2-methylpropan-2-yl)furo[3,2-c]pyridine-2-carboxamide Chemical compound C1=NC=C2C(Br)=C(C(=O)NC(C)(CO)C)OC2=C1Br YDHMHSGGBRWVPT-UHFFFAOYSA-N 0.000 description 2
• QBHLBOWSRQBAHM-UHFFFAOYSA-N 3,7-dibromofuro[3,2-c]pyridine-2-carboxylic acid Chemical compound C1=NC=C2C(Br)=C(C(=O)O)OC2=C1Br QBHLBOWSRQBAHM-UHFFFAOYSA-N 0.000 description 2
• GEFSIPMQWLIINL-UHFFFAOYSA-N 3-aminooxy-3-methylbutan-1-ol Chemical compound NOC(C)(C)CCO GEFSIPMQWLIINL-UHFFFAOYSA-N 0.000 description 2
• FYEQKMAVRYRMBL-UHFFFAOYSA-N 3-aminopyridine-4-carboxylic acid Chemical compound NC1=CN=CC=C1C(O)=O FYEQKMAVRYRMBL-UHFFFAOYSA-N 0.000 description 2
• JEHGATQUCUYHJL-UHFFFAOYSA-N 3-hydroxypyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=C1O JEHGATQUCUYHJL-UHFFFAOYSA-N 0.000 description 2
• 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 2
• 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 2
• 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 2
• ZDVCDFWGMDLBMU-UHFFFAOYSA-N 3-methylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1(O)CCNC1 ZDVCDFWGMDLBMU-UHFFFAOYSA-N 0.000 description 2
• IHKYGDGPCRXNHQ-UHFFFAOYSA-N 4,5-dibromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1Br IHKYGDGPCRXNHQ-UHFFFAOYSA-N 0.000 description 2
• RYOHOUJPNPVRKU-UHFFFAOYSA-N 4,5-dichloropyridine-3-carbaldehyde Chemical compound ClC1=CN=CC(C=O)=C1Cl RYOHOUJPNPVRKU-UHFFFAOYSA-N 0.000 description 2
• XXJWYDDUDKYVKI-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 XXJWYDDUDKYVKI-UHFFFAOYSA-N 0.000 description 2
• XOYHFIQPPOJMFK-UHFFFAOYSA-N 4-bromo-2,5-difluoroaniline Chemical compound NC1=CC(F)=C(Br)C=C1F XOYHFIQPPOJMFK-UHFFFAOYSA-N 0.000 description 2
• QWSUMJXRROQYPN-UHFFFAOYSA-N 4-bromo-3-fluorobenzenethiol Chemical compound FC1=CC(S)=CC=C1Br QWSUMJXRROQYPN-UHFFFAOYSA-N 0.000 description 2
• ADWNZVMFRDVHBL-UHFFFAOYSA-N 4-chloro-5-fluoropyridine-3-carbonitrile Chemical compound FC1=CN=CC(C#N)=C1Cl ADWNZVMFRDVHBL-UHFFFAOYSA-N 0.000 description 2
• IMRGVWZLCZERSQ-UHFFFAOYSA-N 4-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC=C1Cl IMRGVWZLCZERSQ-UHFFFAOYSA-N 0.000 description 2
• XJNPNXSISMKQEX-UHFFFAOYSA-N 4-nitrocatechol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1O XJNPNXSISMKQEX-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
• LNMMZTRANXOGKD-UHFFFAOYSA-N 7-bromo-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylic acid Chemical compound OC(=O)C=1OC2=C(Br)C=NC=C2C=1NC1=CC=C(I)C=C1F LNMMZTRANXOGKD-UHFFFAOYSA-N 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• 239000012103 Alexa Fluor 488 Substances 0.000 description 2
• 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 2
• 208000024827 Alzheimer disease Diseases 0.000 description 2
• BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 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 2
• ZTVOQLMEUARONT-UHFFFAOYSA-N C[Si](C)(C)C1=CC(=C(C=C1)NC2=C(OC3=C2C=NC=C3)C(=O)O)F Chemical compound C[Si](C)(C)C1=CC(=C(C=C1)NC2=C(OC3=C2C=NC=C3)C(=O)O)F ZTVOQLMEUARONT-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 201000009030 Carcinoma Diseases 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
• 208000011231 Crohn disease Diseases 0.000 description 2
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
• AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 2
• 108010092160 Dactinomycin Proteins 0.000 description 2
• 206010012438 Dermatitis atopic Diseases 0.000 description 2
• 206010012655 Diabetic complications Diseases 0.000 description 2
• 206010012689 Diabetic retinopathy Diseases 0.000 description 2
• 102100023266 Dual specificity mitogen-activated protein kinase kinase 2 Human genes 0.000 description 2
• 101710146529 Dual specificity mitogen-activated protein kinase kinase 2 Proteins 0.000 description 2
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
• IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 241000700721 Hepatitis B virus Species 0.000 description 2
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 2
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 2
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
• 239000005551 L01XE03 - Erlotinib Substances 0.000 description 2
• 239000002136 L01XE07 - Lapatinib Substances 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
• 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 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• 206010025323 Lymphomas Diseases 0.000 description 2
• 102000005741 Metalloproteases Human genes 0.000 description 2
• 108010006035 Metalloproteases Proteins 0.000 description 2
• OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 2
• 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 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• 208000009905 Neurofibromatoses Diseases 0.000 description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
• 235000019502 Orange oil Nutrition 0.000 description 2
• 206010061535 Ovarian neoplasm Diseases 0.000 description 2
• 102000038030 PI3Ks Human genes 0.000 description 2
• 108091007960 PI3Ks Proteins 0.000 description 2
• 229930012538 Paclitaxel Natural products 0.000 description 2
• 108090000430 Phosphatidylinositol 3-kinases Proteins 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
• 208000004550 Postoperative Pain Diseases 0.000 description 2
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 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
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• 229940127361 Receptor Tyrosine Kinase Inhibitors Drugs 0.000 description 2
• 208000001647 Renal Insufficiency Diseases 0.000 description 2
• 206010038389 Renal cancer Diseases 0.000 description 2
• 206010038933 Retinopathy of prematurity Diseases 0.000 description 2
• 206010040070 Septic Shock Diseases 0.000 description 2
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 2
• 241000580858 Simian-Human immunodeficiency virus Species 0.000 description 2
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
• 208000006011 Stroke Diseases 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• 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 2
• 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 2
• FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 2
• 108091008605 VEGF receptors Proteins 0.000 description 2
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 2
• 208000036142 Viral infection Diseases 0.000 description 2
• 208000027418 Wounds and injury Diseases 0.000 description 2
• QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
• 206010064930 age-related macular degeneration Diseases 0.000 description 2
• 150000001350 alkyl halides Chemical class 0.000 description 2
• 229940100198 alkylating agent Drugs 0.000 description 2
• 239000002168 alkylating agent Substances 0.000 description 2
• 125000003368 amide group Chemical group 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 229940024606 amino acid Drugs 0.000 description 2
• 235000001014 amino acid Nutrition 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 2
• 229960003437 aminoglutethimide Drugs 0.000 description 2
• CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 2
• 239000004037 angiogenesis inhibitor Substances 0.000 description 2
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
• 239000003242 anti bacterial agent Substances 0.000 description 2
• 230000001093 anti-cancer Effects 0.000 description 2
• 229940088710 antibiotic agent Drugs 0.000 description 2
• 239000003435 antirheumatic agent Substances 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• 239000003125 aqueous solvent Substances 0.000 description 2
• 239000007900 aqueous suspension Substances 0.000 description 2
• 150000001503 aryl iodides Chemical class 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• 201000008937 atopic dermatitis Diseases 0.000 description 2
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 230000005587 bubbling Effects 0.000 description 2
• 229930195731 calicheamicin Natural products 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
• 229910002091 carbon monoxide Inorganic materials 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 125000002843 carboxylic acid group Chemical group 0.000 description 2
• 238000009903 catalytic hydrogenation reaction Methods 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
• KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 2
• 201000010989 colorectal carcinoma Diseases 0.000 description 2
• 229910052802 copper Inorganic materials 0.000 description 2
• 239000010949 copper Substances 0.000 description 2
• 238000006880 cross-coupling reaction Methods 0.000 description 2
• 239000013058 crude material Substances 0.000 description 2
• 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 2
• OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
• 230000006378 damage Effects 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
• 238000010908 decantation Methods 0.000 description 2
• 238000003745 diagnosis Methods 0.000 description 2
• VWCVCLRAPMHDSQ-UHFFFAOYSA-N diethyl 4-chloropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=CN=CC(C(=O)OCC)=C1Cl VWCVCLRAPMHDSQ-UHFFFAOYSA-N 0.000 description 2
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 2
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 2
• 229940043279 diisopropylamine Drugs 0.000 description 2
• 239000002988 disease modifying antirheumatic drug Substances 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 238000012377 drug delivery Methods 0.000 description 2
• 229960005501 duocarmycin Drugs 0.000 description 2
• VQNATVDKACXKTF-XELLLNAOSA-N duocarmycin Chemical compound COC1=C(OC)C(OC)=C2NC(C(=O)N3C4=CC(=O)C5=C([C@@]64C[C@@H]6C3)C=C(N5)C(=O)OC)=CC2=C1 VQNATVDKACXKTF-XELLLNAOSA-N 0.000 description 2
• 229930184221 duocarmycin Natural products 0.000 description 2
• 239000000975 dye Substances 0.000 description 2
• 229920001971 elastomer Polymers 0.000 description 2
• 239000012039 electrophile Substances 0.000 description 2
• 229940073621 enbrel Drugs 0.000 description 2
• 238000005516 engineering process Methods 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
• 125000004185 ester group Chemical group 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
• KMFWUAUMIFXMBF-UHFFFAOYSA-N ethyl 2,4-dichloropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(Cl)C=CN=C1Cl KMFWUAUMIFXMBF-UHFFFAOYSA-N 0.000 description 2
• GBHOBSUTMUPITN-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoyl)-3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-7-carboxylate Chemical compound CN(C)C(=O)C=1OC=2C(C(=O)OCC)=CN=CC=2C=1NC1=CC=C([Si](C)(C)C)C=C1F GBHOBSUTMUPITN-UHFFFAOYSA-N 0.000 description 2
• JQHNWNNSJFQOGE-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoyl)-3-(trifluoromethylsulfonyloxy)furo[3,2-c]pyridine-7-carboxylate Chemical compound CCOC(=O)C1=CN=CC2=C1OC(C(=O)N(C)C)=C2OS(=O)(=O)C(F)(F)F JQHNWNNSJFQOGE-UHFFFAOYSA-N 0.000 description 2
• CNRKIFPQIGSXON-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoyl)-3-hydroxyfuro[3,2-c]pyridine-7-carboxylate Chemical compound CCOC(=O)C1=CN=CC2=C1OC(C(=O)N(C)C)=C2O CNRKIFPQIGSXON-UHFFFAOYSA-N 0.000 description 2
• BVTJSYTWPFNOFE-CYBMUJFWSA-N ethyl 2-[[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxycarbamoyl]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-7-carboxylate Chemical compound C([C@@H]1OC(C)(C)OC1)ONC(=O)C=1OC=2C(C(=O)OCC)=CN=CC=2C=1NC1=CC=C(I)C=C1F BVTJSYTWPFNOFE-CYBMUJFWSA-N 0.000 description 2
• HSQYNCTUQIVXJD-UHFFFAOYSA-N ethyl 2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]oxypropanoate Chemical compound CCOC(=O)C(C)(C)ONC(=O)OC(C)(C)C HSQYNCTUQIVXJD-UHFFFAOYSA-N 0.000 description 2
• KIZCUVQDFZFRNC-UHFFFAOYSA-N ethyl 3-(2,5-difluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC(F)=C(I)C=C1F KIZCUVQDFZFRNC-UHFFFAOYSA-N 0.000 description 2
• WQWMEYGIXGHJGY-UHFFFAOYSA-N ethyl 3-(2,6-difluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=C(F)C=C(I)C=C1F WQWMEYGIXGHJGY-UHFFFAOYSA-N 0.000 description 2
• ZHWLXCJWXGLWJD-UHFFFAOYSA-N ethyl 3-(2-chloro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1Cl ZHWLXCJWXGLWJD-UHFFFAOYSA-N 0.000 description 2
• RXSRCOKOKCHLGA-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-iodoanilino)-4-methylfuro[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC(C)=C2C=1NC1=CC=C(I)C=C1F RXSRCOKOKCHLGA-UHFFFAOYSA-N 0.000 description 2
• ZFIMZBQDCANQHW-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-iodoanilino)-7-methylfuro[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(C)C=NC=C2C=1NC1=CC=C(I)C=C1F ZFIMZBQDCANQHW-UHFFFAOYSA-N 0.000 description 2
• LAPANZLBYWWVSI-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-iodoanilino)-7-phenylfuro[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(C=3C=CC=CC=3)C=NC=C2C=1NC1=CC=C(I)C=C1F LAPANZLBYWWVSI-UHFFFAOYSA-N 0.000 description 2
• MDAKTSHQUBUWGD-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-iodoanilino)furo[2,3-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CN=CC=C2C=1NC1=CC=C(I)C=C1F MDAKTSHQUBUWGD-UHFFFAOYSA-N 0.000 description 2
• QTIKKFUIHTUXAX-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F QTIKKFUIHTUXAX-UHFFFAOYSA-N 0.000 description 2
• CCHHZCDNNAWHSZ-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-iodophenoxy)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1OC1=CC=C(I)C=C1F CCHHZCDNNAWHSZ-UHFFFAOYSA-N 0.000 description 2
• QEDGDODZQHTMON-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-methoxyanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(OC)C=C1F QEDGDODZQHTMON-UHFFFAOYSA-N 0.000 description 2
• QEWQRDNNORDGEA-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-nitrophenoxy)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1OC1=CC=C([N+]([O-])=O)C=C1F QEWQRDNNORDGEA-UHFFFAOYSA-N 0.000 description 2
• FTOMVNHWILRYQJ-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-trimethylsilylanilino)-4-methylfuro[2,3-b]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=NC=CC(C)=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F FTOMVNHWILRYQJ-UHFFFAOYSA-N 0.000 description 2
• XFNMZBOUVUNINS-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-trimethylsilylanilino)-7-methylfuro[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(C)C=NC=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F XFNMZBOUVUNINS-UHFFFAOYSA-N 0.000 description 2
• STXLVZYFJQMTBN-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-trimethylsilylanilino)-7-phenylfuro[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(C=3C=CC=CC=3)C=NC=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F STXLVZYFJQMTBN-UHFFFAOYSA-N 0.000 description 2
• RXBNJEBMXTWMQR-UHFFFAOYSA-N ethyl 3-(4-amino-2-fluorophenoxy)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1OC1=CC=C(N)C=C1F RXBNJEBMXTWMQR-UHFFFAOYSA-N 0.000 description 2
• MNOAWBKPDTUECS-UHFFFAOYSA-N ethyl 3-(4-bromo-2,5-difluoroanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC(F)=C(Br)C=C1F MNOAWBKPDTUECS-UHFFFAOYSA-N 0.000 description 2
• XFMMRCLYKKSFRI-UHFFFAOYSA-N ethyl 3-(4-bromo-2-fluoroanilino)furo[2,3-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CN=CC=C2C=1NC1=CC=C(Br)C=C1F XFMMRCLYKKSFRI-UHFFFAOYSA-N 0.000 description 2
• UOBYLXVZHBYICT-UHFFFAOYSA-N ethyl 3-(4-bromo-2-fluoroanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(Br)C=C1F UOBYLXVZHBYICT-UHFFFAOYSA-N 0.000 description 2
• UNTMNFJCINWBKJ-UHFFFAOYSA-N ethyl 3-(4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1 UNTMNFJCINWBKJ-UHFFFAOYSA-N 0.000 description 2
• WQVCLDQYXRVNKS-UHFFFAOYSA-N ethyl 3-[2-fluoro-4-[tri(propan-2-yl)silyloxymethyl]anilino]furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(CO[Si](C(C)C)(C(C)C)C(C)C)C=C1F WQVCLDQYXRVNKS-UHFFFAOYSA-N 0.000 description 2
• MQXHCQIAEQWPOC-UHFFFAOYSA-N ethyl 3-hydroxyfuro[2,3-c]pyridine-2-carboxylate Chemical compound N1=CC=C2C(O)=C(C(=O)OCC)OC2=C1 MQXHCQIAEQWPOC-UHFFFAOYSA-N 0.000 description 2
• XIBQCRQYVCFUFO-UHFFFAOYSA-N ethyl 3-hydroxypyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1O XIBQCRQYVCFUFO-UHFFFAOYSA-N 0.000 description 2
• RYANKFVJHKIENT-UHFFFAOYSA-N ethyl 4-(2-ethoxy-2-oxoethoxy)pyrimidine-5-carboxylate Chemical compound CCOC(=O)COC1=NC=NC=C1C(=O)OCC RYANKFVJHKIENT-UHFFFAOYSA-N 0.000 description 2
• ZOMODLZCBKIDPL-UHFFFAOYSA-N ethyl 4-chloro-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC(Cl)=C2C=1NC1=CC=C(I)C=C1F ZOMODLZCBKIDPL-UHFFFAOYSA-N 0.000 description 2
• HDVQGLKZQFBTRK-UHFFFAOYSA-N ethyl 4-chloro-3-(trifluoromethylsulfonyloxy)furo[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC(Cl)=C2C(OS(=O)(=O)C(F)(F)F)=C(C(=O)OCC)OC2=C1 HDVQGLKZQFBTRK-UHFFFAOYSA-N 0.000 description 2
• AZWFCHLANFLTFV-UHFFFAOYSA-N ethyl 4-chloro-3-hydroxyfuro[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC(Cl)=C2C(O)=C(C(=O)OCC)OC2=C1 AZWFCHLANFLTFV-UHFFFAOYSA-N 0.000 description 2
• URQGPVFLBZWNQC-UHFFFAOYSA-N ethyl 4-chloro-5-fluoropyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(F)=C1Cl URQGPVFLBZWNQC-UHFFFAOYSA-N 0.000 description 2
• AZJAMMCCAZZXIK-UHFFFAOYSA-N ethyl 4-chloropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=CN=C1Cl AZJAMMCCAZZXIK-UHFFFAOYSA-N 0.000 description 2
• BJAVHYAWENFVID-UHFFFAOYSA-N ethyl 5-(trifluoromethylsulfonyloxy)furo[2,3-d]pyrimidine-6-carboxylate Chemical compound C1=NC=C2C(OS(=O)(=O)C(F)(F)F)=C(C(=O)OCC)OC2=N1 BJAVHYAWENFVID-UHFFFAOYSA-N 0.000 description 2
• LOVDGMMAHIFKFP-UHFFFAOYSA-N ethyl 7-bromo-3-(trifluoromethylsulfonyloxy)furo[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(OS(=O)(=O)C(F)(F)F)=C(C(=O)OCC)OC2=C1Br LOVDGMMAHIFKFP-UHFFFAOYSA-N 0.000 description 2
• FSQKGMMARHFVOW-UHFFFAOYSA-N ethyl 7-chloro-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(Cl)C=NC=C2C=1NC1=CC=C(I)C=C1F FSQKGMMARHFVOW-UHFFFAOYSA-N 0.000 description 2
• PXFCRBLLKQEODD-UHFFFAOYSA-N ethyl 7-cyano-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(C#N)C=NC=C2C=1NC1=CC=C(I)C=C1F PXFCRBLLKQEODD-UHFFFAOYSA-N 0.000 description 2
• PMOLKXRWSPATAE-UHFFFAOYSA-N ethyl 7-fluoro-3-(trifluoromethylsulfonyloxy)furo[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(OS(=O)(=O)C(F)(F)F)=C(C(=O)OCC)OC2=C1F PMOLKXRWSPATAE-UHFFFAOYSA-N 0.000 description 2
• JBDRFTMDIQVDKZ-UHFFFAOYSA-N ethyl 7-fluoro-3-hydroxyfuro[3,2-c]pyridine-2-carboxylate Chemical compound C1=NC=C2C(O)=C(C(=O)OCC)OC2=C1F JBDRFTMDIQVDKZ-UHFFFAOYSA-N 0.000 description 2
• 229940087476 femara Drugs 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• 239000012530 fluid Substances 0.000 description 2
• 235000019152 folic acid Nutrition 0.000 description 2
• 239000011724 folic acid Substances 0.000 description 2
• 229960000304 folic acid Drugs 0.000 description 2
• 235000013355 food flavoring agent Nutrition 0.000 description 2
• CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 2
• 239000007789 gas 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
• 210000004602 germ cell Anatomy 0.000 description 2
• 239000003102 growth factor Substances 0.000 description 2
• 150000008282 halocarbons Chemical class 0.000 description 2
• 201000011066 hemangioma Diseases 0.000 description 2
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
• NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
• 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 2
• 238000002513 implantation Methods 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 208000014674 injury Diseases 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• 208000036971 interstitial lung disease 2 Diseases 0.000 description 2
• 239000011630 iodine Substances 0.000 description 2
• 239000012948 isocyanate Substances 0.000 description 2
• 150000002513 isocyanates Chemical class 0.000 description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• 201000010982 kidney cancer Diseases 0.000 description 2
• 201000006370 kidney failure Diseases 0.000 description 2
• 238000000021 kinase assay Methods 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 2
• 229960003881 letrozole Drugs 0.000 description 2
• 239000002502 liposome Substances 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 210000004185 liver Anatomy 0.000 description 2
• 208000020816 lung neoplasm Diseases 0.000 description 2
• IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
• 208000002780 macular degeneration Diseases 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
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 230000003211 malignant effect Effects 0.000 description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
• 239000012528 membrane Substances 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 229960004857 mitomycin Drugs 0.000 description 2
• AVXXAVLWFWIJIK-UHFFFAOYSA-N n-(2-aminooxyethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCON AVXXAVLWFWIJIK-UHFFFAOYSA-N 0.000 description 2
• RIJYDCJKZDJLNP-UHFFFAOYSA-N n-[(4-chloro-5-fluoropyridin-3-yl)methylidene]hydroxylamine Chemical compound ON=CC1=CN=CC(F)=C1Cl RIJYDCJKZDJLNP-UHFFFAOYSA-N 0.000 description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 201000004931 neurofibromatosis Diseases 0.000 description 2
• 150000002825 nitriles Chemical class 0.000 description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
• 208000002154 non-small cell lung carcinoma Diseases 0.000 description 2
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
• IGVCHDNSQSPODG-UHFFFAOYSA-N o-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]hydroxylamine Chemical compound NOC(C)CO[Si](C)(C)C(C)(C)C IGVCHDNSQSPODG-UHFFFAOYSA-N 0.000 description 2
• MDNVANLCJLEKMY-UHFFFAOYSA-N o-[2-[tert-butyl(dimethyl)silyl]oxypropyl]hydroxylamine Chemical compound NOCC(C)O[Si](C)(C)C(C)(C)C MDNVANLCJLEKMY-UHFFFAOYSA-N 0.000 description 2
• BPQWQFUYGCPJSQ-UHFFFAOYSA-N o-[[1-(4-methylphenyl)sulfonylimidazol-2-yl]methyl]hydroxylamine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CON)=NC=C1 BPQWQFUYGCPJSQ-UHFFFAOYSA-N 0.000 description 2
• 239000010502 orange oil Substances 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 150000002894 organic compounds Chemical class 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 239000001301 oxygen Chemical group 0.000 description 2
• 229960001592 paclitaxel Drugs 0.000 description 2
• 201000002528 pancreatic cancer Diseases 0.000 description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• 102000020233 phosphotransferase Human genes 0.000 description 2
• 208000030761 polycystic kidney disease Diseases 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 201000008171 proliferative glomerulonephritis Diseases 0.000 description 2
• 108060006633 protein kinase Proteins 0.000 description 2
• 239000003586 protic polar solvent Substances 0.000 description 2
• RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 2
• 125000002755 pyrazolinyl group Chemical group 0.000 description 2
• 229960004622 raloxifene Drugs 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
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 2
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 2
• 238000006268 reductive amination reaction Methods 0.000 description 2
• 229940116176 remicade Drugs 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 description 2
• 206010039083 rhinitis Diseases 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 229940095743 selective estrogen receptor modulator Drugs 0.000 description 2
• 239000000333 selective estrogen receptor modulator Substances 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
• 229960002930 sirolimus Drugs 0.000 description 2
• 150000003384 small molecules Chemical class 0.000 description 2
• 239000012279 sodium borohydride Substances 0.000 description 2
• 229910000033 sodium borohydride Inorganic materials 0.000 description 2
• 235000010288 sodium nitrite Nutrition 0.000 description 2
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
• 229960003787 sorafenib Drugs 0.000 description 2
• VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 2
• PVYJZLYGTZKPJE-UHFFFAOYSA-N streptonigrin Chemical compound C=1C=C2C(=O)C(OC)=C(N)C(=O)C2=NC=1C(C=1N)=NC(C(O)=O)=C(C)C=1C1=CC=C(OC)C(OC)=C1O PVYJZLYGTZKPJE-UHFFFAOYSA-N 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
• 239000011593 sulfur Chemical group 0.000 description 2
• 230000004083 survival effect Effects 0.000 description 2
• 238000010189 synthetic method Methods 0.000 description 2
• 239000003826 tablet Substances 0.000 description 2
• FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 2
• TXBMUODKIHDYCT-ZETCQYMHSA-N tert-butyl (3s)-3-aminooxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](ON)C1 TXBMUODKIHDYCT-ZETCQYMHSA-N 0.000 description 2
• FXYJNVGRFDRSKS-UHFFFAOYSA-N tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C)(O)C1 FXYJNVGRFDRSKS-UHFFFAOYSA-N 0.000 description 2
• ZOGLEOIAQNHQHA-UHFFFAOYSA-N tert-butyl n-(1-hydroxy-2-methylpropan-2-yl)oxycarbamate Chemical compound CC(C)(C)OC(=O)NOC(C)(C)CO ZOGLEOIAQNHQHA-UHFFFAOYSA-N 0.000 description 2
• UDICTKJZWXXLJB-UHFFFAOYSA-N tert-butyl n-[2-(1,3-dioxoisoindol-2-yl)oxyethyl]carbamate Chemical compound C1=CC=C2C(=O)N(OCCNC(=O)OC(C)(C)C)C(=O)C2=C1 UDICTKJZWXXLJB-UHFFFAOYSA-N 0.000 description 2
• DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 2
• JXNYUPXVCHGUHU-UHFFFAOYSA-N tert-butyl-dimethyl-(1-phenylmethoxypropan-2-yloxy)silane Chemical compound CC(C)(C)[Si](C)(C)OC(C)COCC1=CC=CC=C1 JXNYUPXVCHGUHU-UHFFFAOYSA-N 0.000 description 2
• 238000012360 testing method Methods 0.000 description 2
• 229960001196 thiotepa Drugs 0.000 description 2
• 229960003087 tioguanine Drugs 0.000 description 2
• 238000011200 topical administration Methods 0.000 description 2
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
• 230000004614 tumor growth Effects 0.000 description 2
• 229960005486 vaccine Drugs 0.000 description 2
• UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 description 2
• 229950000578 vatalanib Drugs 0.000 description 2
• YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 description 2
• 238000010792 warming Methods 0.000 description 2
• 239000003643 water by type Substances 0.000 description 2
• 239000008096 xylene Substances 0.000 description 2
• AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical group N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
• WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 description 1
• SVNJBEMPMKWDCO-KCHLEUMXSA-N (2s)-2-[[(2s)-3-carboxy-2-[[2-[[(2s)-5-(diaminomethylideneamino)-2-[[4-oxo-4-[[4-(4-oxo-8-phenylchromen-2-yl)morpholin-4-ium-4-yl]methoxy]butanoyl]amino]pentanoyl]amino]acetyl]amino]propanoyl]amino]-3-hydroxypropanoate Chemical compound C=1C(=O)C2=CC=CC(C=3C=CC=CC=3)=C2OC=1[N+]1(COC(=O)CCC(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C([O-])=O)CCOCC1 SVNJBEMPMKWDCO-KCHLEUMXSA-N 0.000 description 1
• URLVCROWVOSNPT-XOTOMLERSA-N (2s)-4-[(13r)-13-hydroxy-13-[(2r,5r)-5-[(2r,5r)-5-[(1r)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2h-furan-5-one Chemical compound O1[C@@H]([C@H](O)CCCCCCCCCC)CC[C@@H]1[C@@H]1O[C@@H]([C@H](O)CCCCCCCCCCCCC=2C(O[C@@H](C)C=2)=O)CC1 URLVCROWVOSNPT-XOTOMLERSA-N 0.000 description 1
• CGMTUJFWROPELF-YPAAEMCBSA-N (3E,5S)-5-[(2S)-butan-2-yl]-3-(1-hydroxyethylidene)pyrrolidine-2,4-dione Chemical compound CC[C@H](C)[C@@H]1NC(=O)\C(=C(/C)O)C1=O CGMTUJFWROPELF-YPAAEMCBSA-N 0.000 description 1
• OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 1
• IUHDMWJWUWKOFE-TYSVMGFPSA-N (3r,5r)-5-(hydroxymethyl)pyrrolidin-3-ol;hydrochloride Chemical compound Cl.OC[C@H]1C[C@@H](O)CN1 IUHDMWJWUWKOFE-TYSVMGFPSA-N 0.000 description 1
• VQDUFYPJCUBGQW-UHFFFAOYSA-N (4-bromo-3-fluorophenyl)methanol Chemical compound OCC1=CC=C(Br)C(F)=C1 VQDUFYPJCUBGQW-UHFFFAOYSA-N 0.000 description 1
• XRBSKUSTLXISAB-XVVDYKMHSA-N (5r,6r,7r,8r)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H](CO)[C@@H]2C(O)=O)=C1 XRBSKUSTLXISAB-XVVDYKMHSA-N 0.000 description 1
• OMJKFYKNWZZKTK-POHAHGRESA-N (5z)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide Chemical compound CN(C)N\N=C1/N=CN=C1C(N)=O OMJKFYKNWZZKTK-POHAHGRESA-N 0.000 description 1
• XRBSKUSTLXISAB-UHFFFAOYSA-N (7R,7'R,8R,8'R)-form-Podophyllic acid Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C(CO)C2C(O)=O)=C1 XRBSKUSTLXISAB-UHFFFAOYSA-N 0.000 description 1
• INAUWOVKEZHHDM-PEDBPRJASA-N (7s,9s)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2r,4s,5s,6s)-5-hydroxy-6-methyl-4-morpholin-4-yloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1 INAUWOVKEZHHDM-PEDBPRJASA-N 0.000 description 1
• NOPNWHSMQOXAEI-PUCKCBAPSA-N (7s,9s)-7-[(2r,4s,5s,6s)-4-(2,3-dihydropyrrol-1-yl)-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCC=C1 NOPNWHSMQOXAEI-PUCKCBAPSA-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
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-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
• AGNGYMCLFWQVGX-AGFFZDDWSA-N (e)-1-[(2s)-2-amino-2-carboxyethoxy]-2-diazonioethenolate Chemical compound OC(=O)[C@@H](N)CO\C([O-])=C\[N+]#N AGNGYMCLFWQVGX-AGFFZDDWSA-N 0.000 description 1
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 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
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 description 1
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
• WJUKOGPNGRUXMG-UHFFFAOYSA-N 1,2-dibromo-1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)(Br)C(Cl)(Cl)Br WJUKOGPNGRUXMG-UHFFFAOYSA-N 0.000 description 1
• RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 1
• KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
• LLCWGQYEQKYRDO-UHFFFAOYSA-N 1,2-oxazolidin-4-ol;hydrochloride Chemical compound [Cl-].OC1C[NH2+]OC1 LLCWGQYEQKYRDO-UHFFFAOYSA-N 0.000 description 1
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
• FONKWHRXTPJODV-DNQXCXABSA-N 1,3-bis[2-[(8s)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydro-3h-pyrrolo[3,2-e]indole-6-carbonyl]-1h-indol-5-yl]urea Chemical compound C1([C@H](CCl)CN2C(=O)C=3NC4=CC=C(C=C4C=3)NC(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C4=CC(O)=C5NC=C(C5=C4[C@H](CCl)C3)C)=C2C=C(O)C2=C1C(C)=CN2 FONKWHRXTPJODV-DNQXCXABSA-N 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
• LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 1
• SLFNGVGRINFJLK-UHFFFAOYSA-N 1-bromo-2-fluoro-4-methylbenzene Chemical compound CC1=CC=C(Br)C(F)=C1 SLFNGVGRINFJLK-UHFFFAOYSA-N 0.000 description 1
• DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
• DFPYXQYWILNVAU-UHFFFAOYSA-N 1-hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1.C1=CC=C2N(O)N=NC2=C1 DFPYXQYWILNVAU-UHFFFAOYSA-N 0.000 description 1
• KJBPYIUAQLPHJG-UHFFFAOYSA-N 1-phenylmethoxypropan-2-ol Chemical compound CC(O)COCC1=CC=CC=C1 KJBPYIUAQLPHJG-UHFFFAOYSA-N 0.000 description 1
• XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical class C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
• BTOTXLJHDSNXMW-POYBYMJQSA-N 2,3-dideoxyuridine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(=O)NC(=O)C=C1 BTOTXLJHDSNXMW-POYBYMJQSA-N 0.000 description 1
• KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical group C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
• ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
• TYPVHTOETJVYIV-UHFFFAOYSA-N 2,4-dichloropyridine Chemical compound ClC1=CC=NC(Cl)=C1 TYPVHTOETJVYIV-UHFFFAOYSA-N 0.000 description 1
• FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical class C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 description 1
• JQDNCGRNPYKRAO-UHFFFAOYSA-N 2-(bromomethyl)pyridine;hydron;bromide Chemical compound Br.BrCC1=CC=CC=N1 JQDNCGRNPYKRAO-UHFFFAOYSA-N 0.000 description 1
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 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
• 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
• QINPEPAQOBZPOF-UHFFFAOYSA-N 2-amino-n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-2-methylpropanamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)C(C)(C)N)C=CC=2)=C1 QINPEPAQOBZPOF-UHFFFAOYSA-N 0.000 description 1
• VNBAOSVONFJBKP-UHFFFAOYSA-N 2-chloro-n,n-bis(2-chloroethyl)propan-1-amine;hydrochloride Chemical compound Cl.CC(Cl)CN(CCCl)CCCl VNBAOSVONFJBKP-UHFFFAOYSA-N 0.000 description 1
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
• ZINVZVDSYNURHM-UHFFFAOYSA-N 2-fluoro-4-methylsulfanylaniline Chemical compound CSC1=CC=C(N)C(F)=C1 ZINVZVDSYNURHM-UHFFFAOYSA-N 0.000 description 1
• JNQVLKWNKVMFBN-UHFFFAOYSA-N 2-hydroxy-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CO JNQVLKWNKVMFBN-UHFFFAOYSA-N 0.000 description 1
• 125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
• AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical class NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• 150000004065 2-pyrrolines Chemical class 0.000 description 1
• 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• YIMDLWDNDGKDTJ-QLKYHASDSA-N 3'-deamino-3'-(3-cyanomorpholin-4-yl)doxorubicin Chemical compound N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1C#N YIMDLWDNDGKDTJ-QLKYHASDSA-N 0.000 description 1
• RWKMLYFUEIGBGS-UHFFFAOYSA-N 3,4-dichloro-2h-pyridine-3-carbonitrile Chemical compound ClC1=CC=NCC1(Cl)C#N RWKMLYFUEIGBGS-UHFFFAOYSA-N 0.000 description 1
• ZMPYQKNNUHPTLT-UHFFFAOYSA-N 3,4-dichloropyridine Chemical compound ClC1=CC=NC=C1Cl ZMPYQKNNUHPTLT-UHFFFAOYSA-N 0.000 description 1
• NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
• JXOSTNJEKOKHON-UHFFFAOYSA-N 3-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyloxy)furo[2,3-c]pyridine-2-carboxylic acid Chemical compound C1=CN=CC2=C1C(=C(O2)C(=O)O)OS(=O)(=O)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F JXOSTNJEKOKHON-UHFFFAOYSA-N 0.000 description 1
• QPECKTCAAZCYNN-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxylic acid Chemical compound OC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F QPECKTCAAZCYNN-UHFFFAOYSA-N 0.000 description 1
• PWMYMKOUNYTVQN-UHFFFAOYSA-N 3-(8,8-diethyl-2-aza-8-germaspiro[4.5]decan-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C1C[Ge](CC)(CC)CCC11CN(CCCN(C)C)CC1 PWMYMKOUNYTVQN-UHFFFAOYSA-N 0.000 description 1
• HWUUIOGCBIJILJ-UHFFFAOYSA-N 3-(trifluoromethylsulfonyloxy)furo[3,2-c]pyridine-2-carboxylic acid Chemical compound C1=NC=C2C(OS(=O)(=O)C(F)(F)F)=C(C(=O)O)OC2=C1 HWUUIOGCBIJILJ-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
• FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 150000004066 3-pyrrolines Chemical class 0.000 description 1
• 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 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
• GNYISXOUYFOTGA-UHFFFAOYSA-N 4,5-dichloropyridine-3-carbonitrile Chemical compound ClC1=CN=CC(C#N)=C1Cl GNYISXOUYFOTGA-UHFFFAOYSA-N 0.000 description 1
• CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 description 1
• CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical class [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
• DODQJNMQWMSYGS-QPLCGJKRSA-N 4-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenylbut-1-en-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 DODQJNMQWMSYGS-QPLCGJKRSA-N 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-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
• BFQSQUAVMNHOEF-UHFFFAOYSA-N 4-bromo-2,6-difluoroaniline Chemical compound NC1=C(F)C=C(Br)C=C1F BFQSQUAVMNHOEF-UHFFFAOYSA-N 0.000 description 1
• INMZDDDQLHKGPF-UHFFFAOYSA-N 4-bromo-2-chloroaniline Chemical compound NC1=CC=C(Br)C=C1Cl INMZDDDQLHKGPF-UHFFFAOYSA-N 0.000 description 1
• IZCXVIACMHTZNA-UHFFFAOYSA-N 4-bromo-3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC(S(Cl)(=O)=O)=CC=C1Br IZCXVIACMHTZNA-UHFFFAOYSA-N 0.000 description 1
• MRQYTJXVULSNIS-UHFFFAOYSA-N 4-bromo-3-fluorophenol Chemical compound OC1=CC=C(Br)C(F)=C1 MRQYTJXVULSNIS-UHFFFAOYSA-N 0.000 description 1
• PTCPUGKKWNMITF-UHFFFAOYSA-N 4-chloro-2-fluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1F PTCPUGKKWNMITF-UHFFFAOYSA-N 0.000 description 1
• BEQUUSCRAKEKQM-UHFFFAOYSA-N 4-chloro-3-fluoropyridine Chemical compound FC1=CN=CC=C1Cl BEQUUSCRAKEKQM-UHFFFAOYSA-N 0.000 description 1
• SDRWXOCHMBWAAW-UHFFFAOYSA-N 4-chloro-5-fluoropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(F)=C1Cl SDRWXOCHMBWAAW-UHFFFAOYSA-N 0.000 description 1
• PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 1
• QBKPXDUZFDINDV-UHFFFAOYSA-N 4-chloropyridine-3-carbonitrile Chemical compound ClC1=CC=NC=C1C#N QBKPXDUZFDINDV-UHFFFAOYSA-N 0.000 description 1
• 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
• 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
• GTIHJXQWOSMOPO-UHFFFAOYSA-N 5-(2-fluoro-4-iodoanilino)furo[2,3-d]pyrimidine-6-carboxylic acid Chemical compound OC(=O)C=1OC2=NC=NC=C2C=1NC1=CC=C(I)C=C1F GTIHJXQWOSMOPO-UHFFFAOYSA-N 0.000 description 1
• IDPUKCWIGUEADI-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]uracil Chemical compound ClCCN(CCCl)C1=CNC(=O)NC1=O IDPUKCWIGUEADI-UHFFFAOYSA-N 0.000 description 1
• NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
• FQIUCPGDKPXSLL-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1 FQIUCPGDKPXSLL-UHFFFAOYSA-N 0.000 description 1
• VWXGRWMELBPMCU-UHFFFAOYSA-N 5-chloro-1-[3-(dimethylamino)propyl]-3-phenylbenzimidazol-2-one Chemical compound O=C1N(CCCN(C)C)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 VWXGRWMELBPMCU-UHFFFAOYSA-N 0.000 description 1
• FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 description 1
• LUEQHIRJPGPRQM-UHFFFAOYSA-N 5-hydroxyfuro[2,3-d]pyrimidine-6-carboxylic acid Chemical compound C1=NC=C2C(O)=C(C(=O)O)OC2=N1 LUEQHIRJPGPRQM-UHFFFAOYSA-N 0.000 description 1
• WYXSYVWAUAUWLD-SHUUEZRQSA-N 6-azauridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=N1 WYXSYVWAUAUWLD-SHUUEZRQSA-N 0.000 description 1
• YCWQAMGASJSUIP-YFKPBYRVSA-N 6-diazo-5-oxo-L-norleucine Chemical compound OC(=O)[C@@H](N)CCC(=O)C=[N+]=[N-] YCWQAMGASJSUIP-YFKPBYRVSA-N 0.000 description 1
• 229960005538 6-diazo-5-oxo-L-norleucine Drugs 0.000 description 1
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 1
• PFLZEBDUNBZKLS-UHFFFAOYSA-N 7-bromo-2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-n-(2-fluoro-4-iodophenyl)furo[3,2-c]pyridin-3-amine Chemical compound CC1(C)COC(C2=C(C3=CN=CC(Br)=C3O2)NC=2C(=CC(I)=CC=2)F)=N1 PFLZEBDUNBZKLS-UHFFFAOYSA-N 0.000 description 1
• STWAMEZNLRBSMD-UHFFFAOYSA-N 7-ethoxycarbonyl-3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-2-carboxylic acid Chemical compound OC(=O)C=1OC=2C(C(=O)OCC)=CN=CC=2C=1NC1=CC=C([Si](C)(C)C)C=C1F STWAMEZNLRBSMD-UHFFFAOYSA-N 0.000 description 1
• ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 description 1
• GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
• HDZZVAMISRMYHH-UHFFFAOYSA-N 9beta-Ribofuranosyl-7-deazaadenin Natural products C1=CC=2C(N)=NC=NC=2N1C1OC(CO)C(O)C1O HDZZVAMISRMYHH-UHFFFAOYSA-N 0.000 description 1
• 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
• 206010000830 Acute leukaemia Diseases 0.000 description 1
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
• 108010012934 Albumin-Bound Paclitaxel Proteins 0.000 description 1
• 208000007848 Alcoholism Diseases 0.000 description 1
• CEIZFXOZIQNICU-UHFFFAOYSA-N Alternaria alternata Crofton-weed toxin Natural products CCC(C)C1NC(=O)C(C(C)=O)=C1O CEIZFXOZIQNICU-UHFFFAOYSA-N 0.000 description 1
• 206010061424 Anal cancer Diseases 0.000 description 1
• 108090000644 Angiozyme Proteins 0.000 description 1
• 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 238000006218 Arndt-Eistert homologation reaction Methods 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
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 208000000412 Avitaminosis Diseases 0.000 description 1
• 208000037157 Azotemia Diseases 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 description 1
• 229940122361 Bisphosphonate Drugs 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 206010005003 Bladder cancer Diseases 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• 208000003174 Brain Neoplasms Diseases 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• MBABCNBNDNGODA-LTGLSHGVSA-N Bullatacin Natural products O=C1C(C[C@H](O)CCCCCCCCCC[C@@H](O)[C@@H]2O[C@@H]([C@@H]3O[C@H]([C@@H](O)CCCCCCCCCC)CC3)CC2)=C[C@H](C)O1 MBABCNBNDNGODA-LTGLSHGVSA-N 0.000 description 1
• KGGVWMAPBXIMEM-ZRTAFWODSA-N Bullatacinone Chemical compound O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@@H]1[C@@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@H]2OC(=O)[C@H](CC(C)=O)C2)CC1 KGGVWMAPBXIMEM-ZRTAFWODSA-N 0.000 description 1
• KGGVWMAPBXIMEM-JQFCFGFHSA-N Bullatacinone Natural products O=C(C[C@H]1C(=O)O[C@H](CCCCCCCCCC[C@H](O)[C@@H]2O[C@@H]([C@@H]3O[C@@H]([C@@H](O)CCCCCCCCCC)CC3)CC2)C1)C KGGVWMAPBXIMEM-JQFCFGFHSA-N 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• PHMPZFSMUHSZJW-UHFFFAOYSA-N C1=CN=CC2=C1OC(=C2NC3=C(C=C(C=C3F)Br)F)C(=O)O Chemical compound C1=CN=CC2=C1OC(=C2NC3=C(C=C(C=C3F)Br)F)C(=O)O PHMPZFSMUHSZJW-UHFFFAOYSA-N 0.000 description 1
• OYLNDKYXUZGGHA-UHFFFAOYSA-N C1=CN=CC2=C1OC(=C2NC3=CC(=C(C=C3F)Br)F)C(=O)O Chemical compound C1=CN=CC2=C1OC(=C2NC3=CC(=C(C=C3F)Br)F)C(=O)O OYLNDKYXUZGGHA-UHFFFAOYSA-N 0.000 description 1
• QHHRVOGLXUQUQY-UHFFFAOYSA-N CON(O)CCOC=C Chemical compound CON(O)CCOC=C QHHRVOGLXUQUQY-UHFFFAOYSA-N 0.000 description 1
• UJIKDUPOXHCNSP-UHFFFAOYSA-N C[Si](C)(C)C1=CC(=C(C=C1)NC2=C(OC3=NC=NC=C23)C(=O)O)F Chemical compound C[Si](C)(C)C1=CC(=C(C=C1)NC2=C(OC3=NC=NC=C23)C(=O)O)F UJIKDUPOXHCNSP-UHFFFAOYSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-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
• UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
• 208000005623 Carcinogenesis 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
• 108090000994 Catalytic RNA Proteins 0.000 description 1
• 102000053642 Catalytic RNA Human genes 0.000 description 1
• 208000001387 Causalgia Diseases 0.000 description 1
• 206010008342 Cervix carcinoma Diseases 0.000 description 1
• 229920002567 Chondroitin Polymers 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
• 208000035473 Communicable disease Diseases 0.000 description 1
• 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 1
• 208000034656 Contusions Diseases 0.000 description 1
• 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
• 102000010907 Cyclooxygenase 2 Human genes 0.000 description 1
• 108010037462 Cyclooxygenase 2 Proteins 0.000 description 1
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(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)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
• 108010036949 Cyclosporine Proteins 0.000 description 1
• AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 1
• 108020004414 DNA Proteins 0.000 description 1
• 230000033616 DNA repair Effects 0.000 description 1
• WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
• 201000004624 Dermatitis Diseases 0.000 description 1
• 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
• AUGQEEXBDZWUJY-ZLJUKNTDSA-N Diacetoxyscirpenol Chemical compound C([C@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@@H]1C=C(C)CC[C@@]13COC(=O)C)O2 AUGQEEXBDZWUJY-ZLJUKNTDSA-N 0.000 description 1
• AUGQEEXBDZWUJY-UHFFFAOYSA-N Diacetoxyscirpenol Natural products CC(=O)OCC12CCC(C)=CC1OC1C(O)C(OC(C)=O)C2(C)C11CO1 AUGQEEXBDZWUJY-UHFFFAOYSA-N 0.000 description 1
• 206010061818 Disease progression Diseases 0.000 description 1
• ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
• 238000002965 ELISA Methods 0.000 description 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 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
• OBMLHUPNRURLOK-XGRAFVIBSA-N Epitiostanol Chemical compound C1[C@@H]2S[C@@H]2C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 OBMLHUPNRURLOK-XGRAFVIBSA-N 0.000 description 1
• 229930189413 Esperamicin Natural products 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
• 108050007372 Fibroblast Growth Factor Proteins 0.000 description 1
• 102000018233 Fibroblast Growth Factor Human genes 0.000 description 1
• 238000005967 Finkelstein reaction Methods 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 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
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 description 1
• 108010069236 Goserelin Proteins 0.000 description 1
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
• VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
• 208000004454 Hyperalgesia Diseases 0.000 description 1
• 206010021135 Hypovitaminosis Diseases 0.000 description 1
• MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 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
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 102000051628 Interleukin-1 receptor antagonist Human genes 0.000 description 1
• 108700021006 Interleukin-1 receptor antagonist Proteins 0.000 description 1
• UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
• 239000005909 Kieselgur Substances 0.000 description 1
• 239000001358 L(+)-tartaric acid Substances 0.000 description 1
• 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
• FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-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
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
• 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
• 239000002147 L01XE04 - Sunitinib Substances 0.000 description 1
• 239000005511 L01XE05 - Sorafenib Substances 0.000 description 1
• 229920001491 Lentinan Polymers 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 108010000817 Leuprolide Proteins 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• VJRAUFKOOPNFIQ-UHFFFAOYSA-N Marcellomycin Natural products C12=C(O)C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C=C2C(C(=O)OC)C(CC)(O)CC1OC(OC1C)CC(N(C)C)C1OC(OC1C)CC(O)C1OC1CC(O)C(O)C(C)O1 VJRAUFKOOPNFIQ-UHFFFAOYSA-N 0.000 description 1
• 229930126263 Maytansine Natural products 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 229930192392 Mitomycin Natural products 0.000 description 1
• 241000147123 Moorella group Species 0.000 description 1
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
• IGDKORSMBNIPDP-UHFFFAOYSA-N N-(cyclopropylmethoxy)-N-(2-ethenoxyethyl)hydroxylamine Chemical compound C1(CC1)CON(O)CCOC=C IGDKORSMBNIPDP-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 208000028389 Nerve injury Diseases 0.000 description 1
• 208000005890 Neuroma Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 108010047956 Nucleosomes Proteins 0.000 description 1
• 229930187135 Olivomycin Natural products 0.000 description 1
• 108700020796 Oncogene Proteins 0.000 description 1
• 206010053159 Organ failure Diseases 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 206010033128 Ovarian cancer Diseases 0.000 description 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
• ZJOKWAWPAPMNIM-UHFFFAOYSA-N PD-153035 hydrochloride Chemical compound Cl.C=12C=C(OC)C(OC)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 ZJOKWAWPAPMNIM-UHFFFAOYSA-N 0.000 description 1
• VREZDOWOLGNDPW-ALTGWBOUSA-N Pancratistatin Chemical compound C1=C2[C@H]3[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)[C@@H]3NC(=O)C2=C(O)C2=C1OCO2 VREZDOWOLGNDPW-ALTGWBOUSA-N 0.000 description 1
• VREZDOWOLGNDPW-MYVCAWNPSA-N Pancratistatin Natural products O=C1N[C@H]2[C@H](O)[C@H](O)[C@H](O)[C@H](O)[C@@H]2c2c1c(O)c1OCOc1c2 VREZDOWOLGNDPW-MYVCAWNPSA-N 0.000 description 1
• 108010057150 Peplomycin Proteins 0.000 description 1
• 208000004983 Phantom Limb Diseases 0.000 description 1
• 206010056238 Phantom pain Diseases 0.000 description 1
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
• 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 1
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 1
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• HRHKSTOGXBBQCB-UHFFFAOYSA-N Porfiromycine Chemical compound O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 239000004146 Propane-1,2-diol Substances 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
• 102000001253 Protein Kinase Human genes 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 206010037211 Psychomotor hyperactivity Diseases 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 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
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
• 208000015634 Rectal Neoplasms Diseases 0.000 description 1
• OWPCHSCAPHNHAV-UHFFFAOYSA-N Rhizoxin Natural products C1C(O)C2(C)OC2C=CC(C)C(OC(=O)C2)CC2CC2OC2C(=O)OC1C(C)C(OC)C(C)=CC=CC(C)=CC1=COC(C)=N1 OWPCHSCAPHNHAV-UHFFFAOYSA-N 0.000 description 1
• NSFWWJIQIKBZMJ-YKNYLIOZSA-N Roridin A Chemical compound C([C@]12[C@]3(C)[C@H]4C[C@H]1O[C@@H]1C=C(C)CC[C@@]13COC(=O)[C@@H](O)[C@H](C)CCO[C@H](\C=C\C=C/C(=O)O4)[C@H](O)C)O2 NSFWWJIQIKBZMJ-YKNYLIOZSA-N 0.000 description 1
• 206010061934 Salivary gland cancer Diseases 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 229920002305 Schizophyllan Polymers 0.000 description 1
• 206010039710 Scleroderma Diseases 0.000 description 1
• 206010041067 Small cell lung cancer Diseases 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 208000005718 Stomach Neoplasms Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• BXFOFFBJRFZBQZ-QYWOHJEZSA-N T-2 toxin Chemical compound C([C@@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@H]1[C@]3(COC(C)=O)C[C@@H](C(=C1)C)OC(=O)CC(C)C)O2 BXFOFFBJRFZBQZ-QYWOHJEZSA-N 0.000 description 1
• 229920002253 Tannate Polymers 0.000 description 1
• CGMTUJFWROPELF-UHFFFAOYSA-N Tenuazonic acid Natural products CCC(C)C1NC(=O)C(=C(C)/O)C1=O CGMTUJFWROPELF-UHFFFAOYSA-N 0.000 description 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
• 208000024770 Thyroid neoplasm Diseases 0.000 description 1
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
• 101710183280 Topoisomerase Proteins 0.000 description 1
• FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
• 206010047115 Vasculitis Diseases 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
• 208000004354 Vulvar Neoplasms Diseases 0.000 description 1
• 238000007239 Wittig reaction Methods 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• PVNFMCBFDPTNQI-UIBOPQHZSA-N [(1S,2R,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] acetate [(1S,2R,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 3-methylbutanoate [(1S,2R,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-methylpropanoate [(1S,2R,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] propanoate Chemical compound CO[C@@H]1\C=C\C=C(C)\Cc2cc(OC)c(Cl)c(c2)N(C)C(=O)C[C@H](OC(C)=O)[C@]2(C)OC2[C@H](C)[C@@H]2C[C@@]1(O)NC(=O)O2.CCC(=O)O[C@H]1CC(=O)N(C)c2cc(C\C(C)=C\C=C\[C@@H](OC)[C@@]3(O)C[C@H](OC(=O)N3)[C@@H](C)C3O[C@@]13C)cc(OC)c2Cl.CO[C@@H]1\C=C\C=C(C)\Cc2cc(OC)c(Cl)c(c2)N(C)C(=O)C[C@H](OC(=O)C(C)C)[C@]2(C)OC2[C@H](C)[C@@H]2C[C@@]1(O)NC(=O)O2.CO[C@@H]1\C=C\C=C(C)\Cc2cc(OC)c(Cl)c(c2)N(C)C(=O)C[C@H](OC(=O)CC(C)C)[C@]2(C)OC2[C@H](C)[C@@H]2C[C@@]1(O)NC(=O)O2 PVNFMCBFDPTNQI-UIBOPQHZSA-N 0.000 description 1
• SPJCRMJCFSJKDE-ZWBUGVOYSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 2-[4-[bis(2-chloroethyl)amino]phenyl]acetate Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)C(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 SPJCRMJCFSJKDE-ZWBUGVOYSA-N 0.000 description 1
• DPOQOOQTYRAKHT-UHFFFAOYSA-N [1-(4-methylphenyl)sulfonylimidazol-2-yl]methanol Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(CO)=NC=C1 DPOQOOQTYRAKHT-UHFFFAOYSA-N 0.000 description 1
• XZSRRNFBEIOBDA-CFNBKWCHSA-N [2-[(2s,4s)-4-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]-2-oxoethyl] 2,2-diethoxyacetate 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)C(OCC)OCC)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 XZSRRNFBEIOBDA-CFNBKWCHSA-N 0.000 description 1
• JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
• AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 description 1
• 108010023617 abarelix Proteins 0.000 description 1
• 229960002184 abarelix Drugs 0.000 description 1
• 230000001594 aberrant effect Effects 0.000 description 1
• 229940028652 abraxane Drugs 0.000 description 1
• QUHYUSAHBDACNG-UHFFFAOYSA-N acerogenin 3 Natural products C1=CC(O)=CC=C1CCCCC(=O)CCC1=CC=C(O)C=C1 QUHYUSAHBDACNG-UHFFFAOYSA-N 0.000 description 1
• 229960001138 acetylsalicylic acid Drugs 0.000 description 1
• 238000005903 acid hydrolysis reaction Methods 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 229930188522 aclacinomycin Natural products 0.000 description 1
• USZYSDMBJDPRIF-SVEJIMAYSA-N aclacinomycin A Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1CCC(=O)[C@H](C)O1 USZYSDMBJDPRIF-SVEJIMAYSA-N 0.000 description 1
• 229960004176 aclarubicin Drugs 0.000 description 1
• 229930183665 actinomycin Natural products 0.000 description 1
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 238000009468 active modified atmosphere packaging Methods 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 229940009456 adriamycin Drugs 0.000 description 1
• 108700025316 aldesleukin Proteins 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 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
• 206010053552 allodynia Diseases 0.000 description 1
• 229940061720 alpha hydroxy acid Drugs 0.000 description 1
• 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229960000473 altretamine Drugs 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 230000009435 amidation Effects 0.000 description 1
• 238000007112 amidation reaction Methods 0.000 description 1
• 229960002749 aminolevulinic acid Drugs 0.000 description 1
• 229960003896 aminopterin Drugs 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 201000007538 anal carcinoma Diseases 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 229960002932 anastrozole Drugs 0.000 description 1
• BBDAGFIXKZCXAH-CCXZUQQUSA-N ancitabine Chemical compound N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 BBDAGFIXKZCXAH-CCXZUQQUSA-N 0.000 description 1
• 229950000242 ancitabine Drugs 0.000 description 1
• 239000003098 androgen Substances 0.000 description 1
• 150000001448 anilines Chemical class 0.000 description 1
• 230000002280 anti-androgenic effect Effects 0.000 description 1
• 229940046836 anti-estrogen Drugs 0.000 description 1
• 230000001833 anti-estrogenic effect Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 239000000051 antiandrogen Substances 0.000 description 1
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
• 239000013059 antihormonal agent Substances 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 229940045687 antimetabolites folic acid analogs Drugs 0.000 description 1
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 1
• 239000000074 antisense oligonucleotide Substances 0.000 description 1
• 238000012230 antisense oligonucleotides Methods 0.000 description 1
• 239000006286 aqueous extract Substances 0.000 description 1
• 150000008209 arabinosides Chemical class 0.000 description 1
• 229940059756 arava Drugs 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229940078010 arimidex Drugs 0.000 description 1
• 229940087620 aromasin Drugs 0.000 description 1
• 239000003886 aromatase inhibitor Substances 0.000 description 1
• 229940046844 aromatase inhibitors Drugs 0.000 description 1
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
• 229910052785 arsenic Inorganic materials 0.000 description 1
• 230000002917 arthritic effect Effects 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 125000003120 aryl bromide group Chemical group 0.000 description 1
• 125000003122 aryl chloride group Chemical group 0.000 description 1
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
• 238000006254 arylation reaction Methods 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 229940120638 avastin Drugs 0.000 description 1
• 229960002756 azacitidine Drugs 0.000 description 1
• 229950011321 azaserine Drugs 0.000 description 1
• 229960002170 azathioprine Drugs 0.000 description 1
• LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
• 150000001539 azetidines Chemical class 0.000 description 1
• 150000001541 aziridines Chemical class 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 150000001555 benzenes Chemical class 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 229950005567 benzodepa Drugs 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• VFIUCBTYGKMLCM-UHFFFAOYSA-N benzyl n-[bis(aziridin-1-yl)phosphoryl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NP(=O)(N1CC1)N1CC1 VFIUCBTYGKMLCM-UHFFFAOYSA-N 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
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 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
• 229960000397 bevacizumab Drugs 0.000 description 1
• 229960000997 bicalutamide Drugs 0.000 description 1
• GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
• GNTFBMAGLFYMMZ-UHFFFAOYSA-N bicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CCC2 GNTFBMAGLFYMMZ-UHFFFAOYSA-N 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
• 150000004663 bisphosphonates Chemical class 0.000 description 1
• 229950006844 bizelesin Drugs 0.000 description 1
• 201000000053 blastoma Diseases 0.000 description 1
• 229960001561 bleomycin Drugs 0.000 description 1
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 229910000085 borane Inorganic materials 0.000 description 1
• NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 1
• 229960001467 bortezomib Drugs 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229960005520 bryostatin Drugs 0.000 description 1
• MJQUEDHRCUIRLF-TVIXENOKSA-N bryostatin 1 Chemical compound C([C@@H]1CC(/[C@@H]([C@@](C(C)(C)/C=C/2)(O)O1)OC(=O)/C=C/C=C/CCC)=C\C(=O)OC)[C@H]([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H](O1)C[C@H](OC(C)=O)C(C)(C)[C@]1(O)C[C@@H]1C\C(=C\C(=O)OC)C[C@H]\2O1 MJQUEDHRCUIRLF-TVIXENOKSA-N 0.000 description 1
• MUIWQCKLQMOUAT-AKUNNTHJSA-N bryostatin 20 Natural products COC(=O)C=C1C[C@@]2(C)C[C@]3(O)O[C@](C)(C[C@@H](O)CC(=O)O[C@](C)(C[C@@]4(C)O[C@](O)(CC5=CC(=O)O[C@]45C)C(C)(C)C=C[C@@](C)(C1)O2)[C@@H](C)O)C[C@H](OC(=O)C(C)(C)C)C3(C)C MUIWQCKLQMOUAT-AKUNNTHJSA-N 0.000 description 1
• MBABCNBNDNGODA-LUVUIASKSA-N bullatacin Chemical compound O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@@H]1[C@@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@@H](O)CC=2C(O[C@@H](C)C=2)=O)CC1 MBABCNBNDNGODA-LUVUIASKSA-N 0.000 description 1
• 229960002092 busulfan Drugs 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
• FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 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 1
• 229940127093 camptothecin Drugs 0.000 description 1
• 230000036952 cancer formation Effects 0.000 description 1
• 229960004117 capecitabine Drugs 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• 238000003763 carbonization Methods 0.000 description 1
• YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical compound O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 1
• 229960004562 carboplatin Drugs 0.000 description 1
• 231100000504 carcinogenesis Toxicity 0.000 description 1
• XREUEWVEMYWFFA-CSKJXFQVSA-N carminomycin 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=C(O)C=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XREUEWVEMYWFFA-CSKJXFQVSA-N 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
• 210000000845 cartilage Anatomy 0.000 description 1
• 229950001725 carubicin Drugs 0.000 description 1
• BBZDXMBRAFTCAA-AREMUKBSSA-N carzelesin Chemical compound C1=2NC=C(C)C=2C([C@H](CCl)CN2C(=O)C=3NC4=CC=C(C=C4C=3)NC(=O)C3=CC4=CC=C(C=C4O3)N(CC)CC)=C2C=C1OC(=O)NC1=CC=CC=C1 BBZDXMBRAFTCAA-AREMUKBSSA-N 0.000 description 1
• 229950007509 carzelesin Drugs 0.000 description 1
• 229960002412 cediranib Drugs 0.000 description 1
• 238000000423 cell based assay Methods 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 238000012054 celltiter-glo Methods 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
• DLGJWSVWTWEWBJ-HGGSSLSASA-N chondroitin Chemical compound CC(O)=N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@H](O)C=C(C(O)=O)O1 DLGJWSVWTWEWBJ-HGGSSLSASA-N 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• ZYVSOIYQKUDENJ-WKSBCEQHSA-N chromomycin A3 Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1OC(C)=O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](O[C@@H]3O[C@@H](C)[C@H](OC(C)=O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@@H]1C[C@@H](O)[C@@H](OC)[C@@H](C)O1 ZYVSOIYQKUDENJ-WKSBCEQHSA-N 0.000 description 1
• 229960001265 ciclosporin Drugs 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
• PMMYEEVYMWASQN-QWWZWVQMSA-N cis-4-hydroxy-D-proline Chemical compound O[C@H]1C[NH2+][C@@H](C([O-])=O)C1 PMMYEEVYMWASQN-QWWZWVQMSA-N 0.000 description 1
• 229960004316 cisplatin Drugs 0.000 description 1
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• 238000003776 cleavage reaction Methods 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
• 210000001072 colon Anatomy 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 235000008504 concentrate Nutrition 0.000 description 1
• 230000030944 contact inhibition Effects 0.000 description 1
• 230000009519 contusion Effects 0.000 description 1
• 239000012059 conventional drug carrier Substances 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
• 239000003246 corticosteroid Substances 0.000 description 1
• 229960001334 corticosteroids Drugs 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 150000004292 cyclic ethers Chemical class 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
• 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 1
• 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229930182912 cyclosporin Natural products 0.000 description 1
• 229960000684 cytarabine Drugs 0.000 description 1
• 229940104302 cytosine Drugs 0.000 description 1
• 239000000824 cytostatic agent Substances 0.000 description 1
• 230000001085 cytostatic effect Effects 0.000 description 1
• 229960003901 dacarbazine Drugs 0.000 description 1
• 229960000640 dactinomycin Drugs 0.000 description 1
• 229950006418 dactolisib Drugs 0.000 description 1
• JOGKUKXHTYWRGZ-UHFFFAOYSA-N dactolisib Chemical compound O=C1N(C)C2=CN=C3C=CC(C=4C=C5C=CC=CC5=NC=4)=CC3=C2N1C1=CC=C(C(C)(C)C#N)C=C1 JOGKUKXHTYWRGZ-UHFFFAOYSA-N 0.000 description 1
• 229960000975 daunorubicin Drugs 0.000 description 1
• DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
• 230000006240 deamidation Effects 0.000 description 1
• 238000007257 deesterification reaction Methods 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 238000007872 degassing Methods 0.000 description 1
• 230000001934 delay Effects 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• URLVCROWVOSNPT-QTTMQESMSA-N desacetyluvaricin Natural products O=C1C(CCCCCCCCCCCC[C@@H](O)[C@H]2O[C@@H]([C@@H]3O[C@@H]([C@@H](O)CCCCCCCCCC)CC3)CC2)=C[C@H](C)O1 URLVCROWVOSNPT-QTTMQESMSA-N 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 229950003913 detorubicin Drugs 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
• SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
• JMRYOSQOYJBDOI-UHFFFAOYSA-N dilithium;di(propan-2-yl)azanide Chemical compound [Li+].CC(C)[N-]C(C)C.CC(C)N([Li])C(C)C JMRYOSQOYJBDOI-UHFFFAOYSA-N 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• 230000005750 disease progression Effects 0.000 description 1
• 208000037765 diseases and disorders Diseases 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 125000005883 dithianyl group Chemical group 0.000 description 1
• 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
• 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 1
• 239000003534 dna topoisomerase inhibitor Substances 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
• 229960004679 doxorubicin Drugs 0.000 description 1
• 229950004203 droloxifene Drugs 0.000 description 1
• NOTIQUSPUUHHEH-UXOVVSIBSA-N dromostanolone propionate Chemical compound C([C@@H]1CC2)C(=O)[C@H](C)C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](OC(=O)CC)[C@@]2(C)CC1 NOTIQUSPUUHHEH-UXOVVSIBSA-N 0.000 description 1
• 229950004683 drostanolone propionate Drugs 0.000 description 1
• 230000002183 duodenal effect Effects 0.000 description 1
• FSIRXIHZBIXHKT-MHTVFEQDSA-N edatrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CC(CC)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FSIRXIHZBIXHKT-MHTVFEQDSA-N 0.000 description 1
• 229950006700 edatrexate Drugs 0.000 description 1
• 230000002526 effect on cardiovascular system Effects 0.000 description 1
• VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 1
• 238000001962 electrophoresis Methods 0.000 description 1
• XOPYFXBZMVTEJF-PDACKIITSA-N eleutherobin Chemical compound C(/[C@H]1[C@H](C(=CC[C@@H]1C(C)C)C)C[C@@H]([C@@]1(C)O[C@@]2(C=C1)OC)OC(=O)\C=C\C=1N=CN(C)C=1)=C2\CO[C@@H]1OC[C@@H](O)[C@@H](O)[C@@H]1OC(C)=O XOPYFXBZMVTEJF-PDACKIITSA-N 0.000 description 1
• XOPYFXBZMVTEJF-UHFFFAOYSA-N eleutherobin Natural products C1=CC2(OC)OC1(C)C(OC(=O)C=CC=1N=CN(C)C=1)CC(C(=CCC1C(C)C)C)C1C=C2COC1OCC(O)C(O)C1OC(C)=O XOPYFXBZMVTEJF-UHFFFAOYSA-N 0.000 description 1
• 229940120655 eloxatin Drugs 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 201000008184 embryoma Diseases 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 201000003914 endometrial carcinoma Diseases 0.000 description 1
• 230000002357 endometrial effect Effects 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 229960001904 epirubicin Drugs 0.000 description 1
• 229950002973 epitiostanol Drugs 0.000 description 1
• 229960001433 erlotinib Drugs 0.000 description 1
• ITSGNOIFAJAQHJ-BMFNZSJVSA-N esorubicin 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[C@H](C)O1 ITSGNOIFAJAQHJ-BMFNZSJVSA-N 0.000 description 1
• 229950002017 esorubicin Drugs 0.000 description 1
• LJQQFQHBKUKHIS-WJHRIEJJSA-N esperamicin Chemical compound O1CC(NC(C)C)C(OC)CC1OC1C(O)C(NOC2OC(C)C(SC)C(O)C2)C(C)OC1OC1C(\C2=C/CSSSC)=C(NC(=O)OC)C(=O)C(OC3OC(C)C(O)C(OC(=O)C=4C(=CC(OC)=C(OC)C=4)NC(=O)C(=C)OC)C3)C2(O)C#C\C=C/C#C1 LJQQFQHBKUKHIS-WJHRIEJJSA-N 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 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
• 239000000262 estrogen Substances 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• 239000000328 estrogen antagonist Substances 0.000 description 1
• 229960000403 etanercept Drugs 0.000 description 1
• ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
• QSRLNKCNOLVZIR-KRWDZBQOSA-N ethyl (2s)-2-[[2-[4-[bis(2-chloroethyl)amino]phenyl]acetyl]amino]-4-methylsulfanylbutanoate Chemical compound CCOC(=O)[C@H](CCSC)NC(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 QSRLNKCNOLVZIR-KRWDZBQOSA-N 0.000 description 1
• IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
• FSCPCQRXFGBSHG-UHFFFAOYSA-N ethyl 3-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyloxy)furo[2,3-c]pyridine-2-carboxylate Chemical compound N1=CC=C2C(OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=C(C(=O)OCC)OC2=C1 FSCPCQRXFGBSHG-UHFFFAOYSA-N 0.000 description 1
• MXXGKYQXHNGUIW-UHFFFAOYSA-N ethyl 3-(2-ethoxy-2-oxoethoxy)pyridine-4-carboxylate Chemical compound CCOC(=O)COC1=CN=CC=C1C(=O)OCC MXXGKYQXHNGUIW-UHFFFAOYSA-N 0.000 description 1
• JEDCTBFMMSVCRW-UHFFFAOYSA-N ethyl 3-(2-fluoro-4-methylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(C)C=C1F JEDCTBFMMSVCRW-UHFFFAOYSA-N 0.000 description 1
• WPMRIBNCQLGXAB-UHFFFAOYSA-N ethyl 3-(4-bromo-2,6-difluoroanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NC1=C(F)C=C(Br)C=C1F WPMRIBNCQLGXAB-UHFFFAOYSA-N 0.000 description 1
• DYVMPEWSWWQVJK-UHFFFAOYSA-N ethyl 3-[(2-fluoro-4-iodophenyl)methylamino]furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC=NC=C2C=1NCC1=CC=C(I)C=C1F DYVMPEWSWWQVJK-UHFFFAOYSA-N 0.000 description 1
• STYWLPMGYBPSRJ-UHFFFAOYSA-N ethyl 4-chloropyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC=C1Cl STYWLPMGYBPSRJ-UHFFFAOYSA-N 0.000 description 1
• KBWPYYQARSNBDT-UHFFFAOYSA-N ethyl 5-(2-fluoro-4-iodoanilino)furo[2,3-d]pyrimidine-6-carboxylate Chemical compound CCOC(=O)C=1OC2=NC=NC=C2C=1NC1=CC=C(I)C=C1F KBWPYYQARSNBDT-UHFFFAOYSA-N 0.000 description 1
• OBDXMDGKNCKVKP-UHFFFAOYSA-N ethyl 5-(2-fluoro-4-trimethylsilylanilino)furo[2,3-d]pyrimidine-6-carboxylate Chemical compound CCOC(=O)C=1OC2=NC=NC=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F OBDXMDGKNCKVKP-UHFFFAOYSA-N 0.000 description 1
• MJXBCAKBWTXYNI-UHFFFAOYSA-N ethyl 5-hydroxyfuro[2,3-d]pyrimidine-6-carboxylate Chemical compound C1=NC=C2C(O)=C(C(=O)OCC)OC2=N1 MJXBCAKBWTXYNI-UHFFFAOYSA-N 0.000 description 1
• QASSFGFACYVJLC-UHFFFAOYSA-N ethyl 7-chloro-3-(2-fluoro-4-methylsulfanylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(Cl)C=NC=C2C=1NC1=CC=C(SC)C=C1F QASSFGFACYVJLC-UHFFFAOYSA-N 0.000 description 1
• AHJKQNMQKFNSPC-UHFFFAOYSA-N ethyl 7-cyano-3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(C#N)C=NC=C2C=1NC1=CC=C([Si](C)(C)C)C=C1F AHJKQNMQKFNSPC-UHFFFAOYSA-N 0.000 description 1
• CXQWCZYYSDDCRH-UHFFFAOYSA-N ethyl 7-fluoro-3-(2-fluoro-4-methylsulfanylanilino)furo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C=1OC2=C(F)C=NC=C2C=1NC1=CC=C(SC)C=C1F CXQWCZYYSDDCRH-UHFFFAOYSA-N 0.000 description 1
• MSMGXWFHBSCQFB-UHFFFAOYSA-N ethyl cyanoformate Chemical compound CCOC(=O)C#N MSMGXWFHBSCQFB-UHFFFAOYSA-N 0.000 description 1
• 125000005469 ethylenyl group Chemical group 0.000 description 1
• WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
• 229940064982 ethylnicotinate Drugs 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide 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)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 229960000255 exemestane Drugs 0.000 description 1
• 229950011548 fadrozole Drugs 0.000 description 1
• 229940126864 fibroblast growth factor Drugs 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
• 229960004413 flucytosine 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
• IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 1
• 239000007850 fluorescent dye Substances 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
• 239000006260 foam Substances 0.000 description 1
• 150000002224 folic acids Chemical class 0.000 description 1
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
• 235000008191 folinic acid Nutrition 0.000 description 1
• 239000011672 folinic acid Substances 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 230000022244 formylation Effects 0.000 description 1
• 238000006170 formylation reaction Methods 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 229960002258 fulvestrant Drugs 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 229960002598 fumaric acid Drugs 0.000 description 1
• 230000006870 function Effects 0.000 description 1
• ZYXBIOIYWUIXSM-UHFFFAOYSA-N furo[2,3-c]pyridine Chemical class C1=NC=C2OC=CC2=C1 ZYXBIOIYWUIXSM-UHFFFAOYSA-N 0.000 description 1
• PONAXVAFSSUYFZ-UHFFFAOYSA-N furo[2,3-d]pyridazine Chemical class N1=NC=C2OC=CC2=C1 PONAXVAFSSUYFZ-UHFFFAOYSA-N 0.000 description 1
• KQGXYVJZOMKLSA-UHFFFAOYSA-N furo[2,3-d]pyrimidine Chemical class N1=CN=C2OC=CC2=C1 KQGXYVJZOMKLSA-UHFFFAOYSA-N 0.000 description 1
• KXDJPLSALUSYNT-UHFFFAOYSA-N furo[3,2-c]pyridazine Chemical class N1=CC=C2OC=CC2=N1 KXDJPLSALUSYNT-UHFFFAOYSA-N 0.000 description 1
• WJDMEHCIRPKRRQ-UHFFFAOYSA-N furo[3,2-c]pyridine Chemical class N1=CC=C2OC=CC2=C1 WJDMEHCIRPKRRQ-UHFFFAOYSA-N 0.000 description 1
• 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 229940044658 gallium nitrate Drugs 0.000 description 1
• 206010017758 gastric cancer Diseases 0.000 description 1
• 229960002584 gefitinib Drugs 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
• 229960005277 gemcitabine Drugs 0.000 description 1
• 229940020967 gemzar Drugs 0.000 description 1
• 238000001415 gene therapy Methods 0.000 description 1
• 229940114119 gentisate Drugs 0.000 description 1
• 210000004907 gland Anatomy 0.000 description 1
• 229940080856 gleevec Drugs 0.000 description 1
• 208000005017 glioblastoma Diseases 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 229940097042 glucuronate Drugs 0.000 description 1
• 229940097043 glucuronic acid Drugs 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 229960004275 glycolic acid Drugs 0.000 description 1
• 229930182470 glycoside Natural products 0.000 description 1
• 229960002913 goserelin Drugs 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 230000026030 halogenation Effects 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 208000014829 head and neck neoplasm Diseases 0.000 description 1
• 230000002440 hepatic effect Effects 0.000 description 1
• 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
• 150000002391 heterocyclic compounds Chemical class 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
• 230000003054 hormonal effect Effects 0.000 description 1
• 231100000508 hormonal effect Toxicity 0.000 description 1
• 229940048921 humira Drugs 0.000 description 1
• 229920002674 hyaluronan Polymers 0.000 description 1
• 229960003160 hyaluronic acid Drugs 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 229960001330 hydroxycarbamide Drugs 0.000 description 1
• 230000033444 hydroxylation Effects 0.000 description 1
• 238000005805 hydroxylation reaction Methods 0.000 description 1
• 208000003532 hypothyroidism Diseases 0.000 description 1
• 230000002989 hypothyroidism 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
• 229960003685 imatinib mesylate Drugs 0.000 description 1
• 150000002460 imidazoles Chemical class 0.000 description 1
• 150000002461 imidazolidines Chemical class 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 239000000367 immunologic factor Substances 0.000 description 1
• 239000002955 immunomodulating agent Substances 0.000 description 1
• 229940121354 immunomodulator Drugs 0.000 description 1
• DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 1
• 229950008097 improsulfan Drugs 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-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
• 125000001041 indolyl group Chemical group 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 229960000598 infliximab Drugs 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000003999 initiator Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 229910017053 inorganic salt Inorganic materials 0.000 description 1
• 229940030980 inova Drugs 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 230000009545 invasion Effects 0.000 description 1
• 229940084651 iressa Drugs 0.000 description 1
• KLEAIHJJLUAXIQ-JDRGBKBRSA-N irinotecan hydrochloride hydrate Chemical compound O.O.O.Cl.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 KLEAIHJJLUAXIQ-JDRGBKBRSA-N 0.000 description 1
• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
• TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 230000002147 killing effect Effects 0.000 description 1
• 229940054136 kineret Drugs 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
• 150000002596 lactones Chemical class 0.000 description 1
• 229960004891 lapatinib Drugs 0.000 description 1
• 229960000681 leflunomide Drugs 0.000 description 1
• 229940115286 lentinan Drugs 0.000 description 1
• 229960001691 leucovorin Drugs 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 1
• 229960004338 leuprorelin Drugs 0.000 description 1
• QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
• 238000011542 limb amputation Methods 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 208000014018 liver neoplasm Diseases 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• RVFGKBWWUQOIOU-NDEPHWFRSA-N lurtotecan Chemical compound O=C([C@]1(O)CC)OCC(C(N2CC3=4)=O)=C1C=C2C3=NC1=CC=2OCCOC=2C=C1C=4CN1CCN(C)CC1 RVFGKBWWUQOIOU-NDEPHWFRSA-N 0.000 description 1
• 229950002654 lurtotecan Drugs 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 229940098895 maleic acid Drugs 0.000 description 1
• 208000026037 malignant tumor of neck Diseases 0.000 description 1
• 229960002510 mandelic acid Drugs 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
• MQXVYODZCMMZEM-ZYUZMQFOSA-N mannomustine Chemical compound ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl MQXVYODZCMMZEM-ZYUZMQFOSA-N 0.000 description 1
• 229950008612 mannomustine Drugs 0.000 description 1
• 238000004519 manufacturing process 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
• 229960004961 mechlorethamine Drugs 0.000 description 1
• HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
• RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
• 229960004296 megestrol acetate Drugs 0.000 description 1
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
• 229960001924 melphalan Drugs 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
• KBOPZPXVLCULAV-UHFFFAOYSA-M mesalaminate(1-) Chemical compound NC1=CC=C(O)C(C([O-])=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-M 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 0.000 description 1
• 239000003475 metalloproteinase inhibitor Substances 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• VJRAUFKOOPNFIQ-TVEKBUMESA-N methyl (1r,2r,4s)-4-[(2r,4s,5s,6s)-5-[(2s,4s,5s,6s)-5-[(2s,4s,5s,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylat Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1C[C@H](O)[C@H](O)[C@H](C)O1 VJRAUFKOOPNFIQ-TVEKBUMESA-N 0.000 description 1
• QRMNENFZDDYDEF-GOSISDBHSA-N methyl (8s)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-7,8-dihydro-3h-pyrrolo[3,2-e]indole-1-carboxylate Chemical compound C1([C@H](CBr)CN(C1=C1)C(=O)C=2NC3=C(OC)C(OC)=C(OC)C=C3C=2)=C2C(C(=O)OC)=C(C)NC2=C1OC(=O)N1CCN(C)CC1 QRMNENFZDDYDEF-GOSISDBHSA-N 0.000 description 1
• NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (ne)-n-methoxycarbonyliminocarbamate Chemical compound COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-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
• HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
• 239000003226 mitogen Substances 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
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 239000003068 molecular probe Substances 0.000 description 1
• 125000001620 monocyclic carbocycle group Chemical group 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 description 1
• 229960000951 mycophenolic acid Drugs 0.000 description 1
• PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
• WGUGGOZTNXDBHS-UHFFFAOYSA-N n-(cyclopropylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.ONCC1CC1 WGUGGOZTNXDBHS-UHFFFAOYSA-N 0.000 description 1
• GZCHEVXYDGQDCP-UHFFFAOYSA-N n-[2-(1,3-dioxoisoindol-2-yl)oxyethyl]ethanesulfonamide Chemical compound C1=CC=C2C(=O)N(OCCNS(=O)(=O)CC)C(=O)C2=C1 GZCHEVXYDGQDCP-UHFFFAOYSA-N 0.000 description 1
• VTDDWQZUNUVJNH-UHFFFAOYSA-N n-[2-(1,3-dioxoisoindol-2-yl)oxyethyl]methanesulfonamide Chemical compound C1=CC=C2C(=O)N(OCCNS(=O)(=O)C)C(=O)C2=C1 VTDDWQZUNUVJNH-UHFFFAOYSA-N 0.000 description 1
• WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
• MGNPLIACIXIYJE-UHFFFAOYSA-N n-fluoroaniline Chemical compound FNC1=CC=CC=C1 MGNPLIACIXIYJE-UHFFFAOYSA-N 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 239000002105 nanoparticle Substances 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 229930014626 natural product Natural products 0.000 description 1
• 230000008764 nerve damage Effects 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
• 238000006396 nitration reaction Methods 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 229940085033 nolvadex Drugs 0.000 description 1
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
• 230000025308 nuclear transport Effects 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
• 239000002777 nucleoside Substances 0.000 description 1
• 210000001623 nucleosome Anatomy 0.000 description 1
• 238000011580 nude mouse model Methods 0.000 description 1
• MFJWCIKWSBBOOV-UHFFFAOYSA-N o-(1-phenylethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOC(C)C1=CC=CC=C1 MFJWCIKWSBBOOV-UHFFFAOYSA-N 0.000 description 1
• DCIKEGMDLASJHI-RXMQYKEDSA-N o-[[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]hydroxylamine Chemical compound CC1(C)OC[C@H](CON)O1 DCIKEGMDLASJHI-RXMQYKEDSA-N 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• CZDBNBLGZNWKMC-MWQNXGTOSA-N olivomycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1)O[C@H]1O[C@@H](C)[C@H](O)[C@@H](OC2O[C@@H](C)[C@H](O)[C@@H](O)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@H](O)[C@H](OC)[C@H](C)O1 CZDBNBLGZNWKMC-MWQNXGTOSA-N 0.000 description 1
• 229950005848 olivomycin Drugs 0.000 description 1
• 229950011093 onapristone Drugs 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
• 201000008482 osteoarthritis Diseases 0.000 description 1
• 230000002611 ovarian Effects 0.000 description 1
• 229940116315 oxalic acid Drugs 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 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 1
• 229960001756 oxaliplatin Drugs 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003551 oxepanyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• VREZDOWOLGNDPW-UHFFFAOYSA-N pancratistatine Natural products C1=C2C3C(O)C(O)C(O)C(O)C3NC(=O)C2=C(O)C2=C1OCO2 VREZDOWOLGNDPW-UHFFFAOYSA-N 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 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
• 239000006201 parenteral dosage form Substances 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 208000030940 penile carcinoma Diseases 0.000 description 1
• 201000008174 penis carcinoma Diseases 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
• QIMGFXOHTOXMQP-GFAGFCTOSA-N peplomycin Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCCN[C@@H](C)C=1C=CC=CC=1)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C QIMGFXOHTOXMQP-GFAGFCTOSA-N 0.000 description 1
• 229950003180 peplomycin Drugs 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 201000002628 peritoneum cancer Diseases 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
• 238000003566 phosphorylation assay Methods 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
• 230000004962 physiological condition Effects 0.000 description 1
• 239000000049 pigment Substances 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 229960001221 pirarubicin Drugs 0.000 description 1
• 150000003057 platinum Chemical class 0.000 description 1
• 239000008389 polyethoxylated castor oil Substances 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920001282 polysaccharide Polymers 0.000 description 1
• 239000005017 polysaccharide Substances 0.000 description 1
• 150000004804 polysaccharides Chemical class 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
• 229910000105 potassium hydride Inorganic materials 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 150000003138 primary alcohols Chemical class 0.000 description 1
• 238000002810 primary assay Methods 0.000 description 1
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
• 229960000624 procarbazine Drugs 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• 229940087463 proleukin Drugs 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 239000011814 protection agent Substances 0.000 description 1
• 239000003909 protein kinase inhibitor Substances 0.000 description 1
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
• WOLQREOUPKZMEX-UHFFFAOYSA-N pteroyltriglutamic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)C=C1 WOLQREOUPKZMEX-UHFFFAOYSA-N 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 229950010131 puromycin Drugs 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 150000003217 pyrazoles Chemical class 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 150000003219 pyrazolines Chemical class 0.000 description 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 150000003233 pyrroles Chemical class 0.000 description 1
• 150000003235 pyrrolidines Chemical class 0.000 description 1
• SJSABZBUTDSWMJ-UHFFFAOYSA-N pyrrolo[3,4-c]pyridine-1,3-dione Chemical compound N1=CC=C2C(=O)NC(=O)C2=C1 SJSABZBUTDSWMJ-UHFFFAOYSA-N 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• UOWVMDUEMSNCAV-WYENRQIDSA-N rachelmycin Chemical compound C1([C@]23C[C@@H]2CN1C(=O)C=1NC=2C(OC)=C(O)C4=C(C=2C=1)CCN4C(=O)C1=CC=2C=4CCN(C=4C(O)=C(C=2N1)OC)C(N)=O)=CC(=O)C1=C3C(C)=CN1 UOWVMDUEMSNCAV-WYENRQIDSA-N 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 102000009929 raf Kinases Human genes 0.000 description 1
• 108010077182 raf Kinases Proteins 0.000 description 1
• 229960002185 ranimustine Drugs 0.000 description 1
• 229940099538 rapamune Drugs 0.000 description 1
• 230000009257 reactivity Effects 0.000 description 1
• 206010038038 rectal cancer Diseases 0.000 description 1
• 201000001275 rectum cancer Diseases 0.000 description 1
• 238000005932 reductive alkylation reaction Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000008844 regulatory mechanism Effects 0.000 description 1
• 230000008521 reorganization Effects 0.000 description 1
• 230000000717 retained effect Effects 0.000 description 1
• 229930002330 retinoic acid Natural products 0.000 description 1
• OWPCHSCAPHNHAV-LMONGJCWSA-N rhizoxin Chemical compound C/C([C@H](OC)[C@@H](C)[C@@H]1C[C@H](O)[C@]2(C)O[C@@H]2/C=C/[C@@H](C)[C@]2([H])OC(=O)C[C@@](C2)(C[C@@H]2O[C@H]2C(=O)O1)[H])=C\C=C\C(\C)=C\C1=COC(C)=N1 OWPCHSCAPHNHAV-LMONGJCWSA-N 0.000 description 1
• 108091092562 ribozyme Proteins 0.000 description 1
• MBABCNBNDNGODA-WPZDJQSSSA-N rolliniastatin 1 Natural products O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@H]1[C@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@@H](O)CC=2C(O[C@@H](C)C=2)=O)CC1 MBABCNBNDNGODA-WPZDJQSSSA-N 0.000 description 1
• IMUQLZLGWJSVMV-UOBFQKKOSA-N roridin A Natural products CC(O)C1OCCC(C)C(O)C(=O)OCC2CC(=CC3OC4CC(OC(=O)C=C/C=C/1)C(C)(C23)C45CO5)C IMUQLZLGWJSVMV-UOBFQKKOSA-N 0.000 description 1
• 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 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 201000003804 salivary gland carcinoma Diseases 0.000 description 1
• 239000000523 sample Substances 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 150000003333 secondary alcohols Chemical class 0.000 description 1
• 238000002805 secondary assay Methods 0.000 description 1
• 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 208000000587 small cell lung carcinoma Diseases 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 235000015096 spirit Nutrition 0.000 description 1
• 125000003003 spiro group Chemical group 0.000 description 1
• 229950006315 spirogermanium Drugs 0.000 description 1
• 208000017572 squamous cell neoplasm Diseases 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 230000003068 static effect Effects 0.000 description 1
• 239000008174 sterile solution Substances 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 201000011549 stomach cancer Diseases 0.000 description 1
• ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
• 229960001052 streptozocin Drugs 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
• NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
• 229960001940 sulfasalazine Drugs 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 150000003871 sulfonates Chemical class 0.000 description 1
• 230000006103 sulfonylation Effects 0.000 description 1
• 238000005694 sulfonylation reaction Methods 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• 229960001796 sunitinib Drugs 0.000 description 1
• 239000013589 supplement Substances 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 230000008961 swelling Effects 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229960001603 tamoxifen Drugs 0.000 description 1
• 229960003454 tamoxifen citrate Drugs 0.000 description 1
• 229940120982 tarceva Drugs 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• RCINICONZNJXQF-XAZOAEDWSA-N taxol® Chemical compound O([C@@H]1[C@@]2(CC(C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3(C21)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-XAZOAEDWSA-N 0.000 description 1
• 229940063683 taxotere 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
• GIIDZEBNRLNGMS-HTQZYQBOSA-N tert-butyl (2r,3r)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](O)[C@H]1CO GIIDZEBNRLNGMS-HTQZYQBOSA-N 0.000 description 1
• APCBTRDHCDOPNY-SSDOTTSWSA-N tert-butyl (3r)-3-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](O)C1 APCBTRDHCDOPNY-SSDOTTSWSA-N 0.000 description 1
• MOZOQDNRVPHFOO-RNFRBKRXSA-N tert-butyl (3r,4r)-3-amino-4-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](N)[C@H](O)C1 MOZOQDNRVPHFOO-RNFRBKRXSA-N 0.000 description 1
• XJMZVQVTRJUZNV-NSHDSACASA-N tert-butyl (3s)-3-(1,3-dioxoisoindol-2-yl)oxypyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@@H]1ON1C(=O)C2=CC=CC=C2C1=O XJMZVQVTRJUZNV-NSHDSACASA-N 0.000 description 1
• JSOMVCDXPUXKIC-UHFFFAOYSA-N tert-butyl 3-oxopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)C1 JSOMVCDXPUXKIC-UHFFFAOYSA-N 0.000 description 1
• GPTXCAZYUMDUMN-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCO GPTXCAZYUMDUMN-UHFFFAOYSA-N 0.000 description 1
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
• VRBDOANIUGZPKN-UHFFFAOYSA-N tert-butyl-dimethyl-(1,2-oxazolidin-4-yloxy)silane Chemical compound CC(C)(C)[Si](C)(C)OC1CNOC1 VRBDOANIUGZPKN-UHFFFAOYSA-N 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
• 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000001583 thiepanyl group Chemical group 0.000 description 1
• 125000002053 thietanyl group Chemical group 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
• 201000002510 thyroid cancer Diseases 0.000 description 1
• 208000037816 tissue injury Diseases 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
• 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
• 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 1
• 229960000303 topotecan Drugs 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000013519 translation Methods 0.000 description 1
• 230000005945 translocation Effects 0.000 description 1
• IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
• 229950001353 tretamine Drugs 0.000 description 1
• 229960001727 tretinoin Drugs 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• LZAJKCZTKKKZNT-PMNGPLLRSA-N trichothecene Chemical compound C12([C@@]3(CC[C@H]2OC2C=C(CCC23C)C)C)CO1 LZAJKCZTKKKZNT-PMNGPLLRSA-N 0.000 description 1
• 229930013292 trichothecene Natural products 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
• 206010044652 trigeminal neuralgia Diseases 0.000 description 1
• KVJXBPDAXMEYOA-CXANFOAXSA-N trilostane Chemical compound OC1=C(C#N)C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@@]32O[C@@H]31 KVJXBPDAXMEYOA-CXANFOAXSA-N 0.000 description 1
• 229960001670 trilostane Drugs 0.000 description 1
• 229960000875 trofosfamide Drugs 0.000 description 1
• UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 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
• 229950010147 troxacitabine Drugs 0.000 description 1
• HDZZVAMISRMYHH-LITAXDCLSA-N tubercidin Chemical compound C1=CC=2C(N)=NC=NC=2N1[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O HDZZVAMISRMYHH-LITAXDCLSA-N 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
• 231100000588 tumorigenic Toxicity 0.000 description 1
• 230000000381 tumorigenic effect Effects 0.000 description 1
• 229940094060 tykerb Drugs 0.000 description 1
• GFNNBHLJANVSQV-UHFFFAOYSA-N tyrphostin AG 1478 Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1 GFNNBHLJANVSQV-UHFFFAOYSA-N 0.000 description 1
• 229950009811 ubenimex Drugs 0.000 description 1
• 229960001055 uracil mustard Drugs 0.000 description 1
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
• SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
• 229950006929 uredepa Drugs 0.000 description 1
• 208000009852 uremia Diseases 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 208000012991 uterine carcinoma Diseases 0.000 description 1
• 229960000241 vandetanib Drugs 0.000 description 1
• LLDWLPRYLVPDTG-UHFFFAOYSA-N vatalanib succinate Chemical compound OC(=O)CCC(O)=O.C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 LLDWLPRYLVPDTG-UHFFFAOYSA-N 0.000 description 1
• 229940099039 velcade Drugs 0.000 description 1
• 238000009423 ventilation Methods 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
• UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
• 229960004355 vindesine Drugs 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 208000030401 vitamin deficiency disease Diseases 0.000 description 1
• 201000005102 vulva cancer Diseases 0.000 description 1
• 229940053867 xeloda Drugs 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
• FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin 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)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
• 229960000641 zorubicin Drugs 0.000 description 1
• 150000003952 β-lactams Chemical class 0.000 description 1