TWI698435B - 作為吲哚胺２,３-二加氧酶和/或色氨酸２,３-二加氧酶抑制劑之新穎之５或８-取代之咪唑並［１，５－ａ］吡啶 - Google Patents

Info

Publication number

TWI698435B

TWI698435B TW105111144A TW105111144A TWI698435B TW I698435 B TWI698435 B TW I698435B TW 105111144 A TW105111144 A TW 105111144A TW 105111144 A TW105111144 A TW 105111144A TW I698435 B TWI698435 B TW I698435B

Authority

TW

Taiwan

Prior art keywords

alkyl

haloalkyl

compound

aryl

heteroaryl

Prior art date

2015-04-10

Links

• Espacenet
• Global Dossier
• Discuss

• QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 title abstract description 16
• 229960004799 tryptophan Drugs 0.000 title abstract description 10
• QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 title abstract description 7
• 239000006035 Tryptophane Substances 0.000 title abstract 2
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 title 1
• RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 1
• -1 8-substituted imidazo[1,5-a]pyridines Chemical class 0.000 claims abstract description 159
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
• 208000035475 disorder Diseases 0.000 claims abstract description 9
• 238000002360 preparation method Methods 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims description 300
• 125000000217 alkyl group Chemical group 0.000 claims description 180
• 125000003118 aryl group Chemical group 0.000 claims description 128
• 229910052739 hydrogen Inorganic materials 0.000 claims description 118
• 229910052736 halogen Inorganic materials 0.000 claims description 111
• 150000002367 halogens Chemical class 0.000 claims description 111
• 125000001072 heteroaryl group Chemical group 0.000 claims description 111
• 239000001257 hydrogen Substances 0.000 claims description 108
• 125000000623 heterocyclic group Chemical group 0.000 claims description 106
• 150000003839 salts Chemical class 0.000 claims description 106
• 150000002431 hydrogen Chemical class 0.000 claims description 79
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 66
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 52
• 125000003342 alkenyl group Chemical group 0.000 claims description 50
• 125000000304 alkynyl group Chemical group 0.000 claims description 49
• 125000001424 substituent group Chemical group 0.000 claims description 45
• 229920006395 saturated elastomer Polymers 0.000 claims description 39
• 206010028980 Neoplasm Diseases 0.000 claims description 37
• 102100040061 Indoleamine 2,3-dioxygenase 1 Human genes 0.000 claims description 36
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
• 101001037256 Homo sapiens Indoleamine 2,3-dioxygenase 1 Proteins 0.000 claims description 35
• 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 33
• 239000000460 chlorine Substances 0.000 claims description 29
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 28
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 125000005842 heteroatom Chemical group 0.000 claims description 26
• 201000011510 cancer Diseases 0.000 claims description 25
• 238000011282 treatment Methods 0.000 claims description 25
• 125000002619 bicyclic group Chemical group 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
• 229940079593 drug Drugs 0.000 claims description 16
• JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical group C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 claims description 15
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
• 239000004480 active ingredient Substances 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 206010009944 Colon cancer Diseases 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 201000005787 hematologic cancer Diseases 0.000 claims description 10
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 9
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 206010017758 gastric cancer Diseases 0.000 claims description 9
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 9
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 9
• 201000011549 stomach cancer Diseases 0.000 claims description 9
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 239000001301 oxygen Chemical group 0.000 claims description 8
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000002950 monocyclic group Chemical group 0.000 claims description 7
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 7
• 208000030507 AIDS Diseases 0.000 claims description 6
• 230000003463 hyperproliferative effect Effects 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 claims description 5
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 5
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 5
• 206010014733 Endometrial cancer Diseases 0.000 claims description 5
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 5
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 5
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• 206010025323 Lymphomas Diseases 0.000 claims description 5
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
• 206010060862 Prostate cancer Diseases 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 206010038389 Renal cancer Diseases 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 5
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
• 208000009956 adenocarcinoma Diseases 0.000 claims description 5
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 5
• 201000010881 cervical cancer Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 201000004101 esophageal cancer Diseases 0.000 claims description 5
• 201000010536 head and neck cancer Diseases 0.000 claims description 5
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 201000010982 kidney cancer Diseases 0.000 claims description 5
• 201000007270 liver cancer Diseases 0.000 claims description 5
• 208000014018 liver neoplasm Diseases 0.000 claims description 5
• 201000005249 lung adenocarcinoma Diseases 0.000 claims description 5
• 201000005202 lung cancer Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
• 201000002528 pancreatic cancer Diseases 0.000 claims description 5
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
• 239000011593 sulfur Chemical group 0.000 claims description 5
• 201000002510 thyroid cancer Diseases 0.000 claims description 5
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 5
• 208000020790 biliary tract neoplasm Diseases 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 201000009036 biliary tract cancer Diseases 0.000 claims description 3
• 230000002708 enhancing effect Effects 0.000 claims description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 230000004044 response Effects 0.000 claims description 3
• 230000003612 virological effect Effects 0.000 claims description 3
• 230000001747 exhibiting effect Effects 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 150000001350 alkyl halides Chemical class 0.000 claims 1
• 238000010839 reverse transcription Methods 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 38
• 102000006639 indoleamine 2,3-dioxygenase Human genes 0.000 abstract description 36
• 108020004201 indoleamine 2,3-dioxygenase Proteins 0.000 abstract description 36
• 230000002401 inhibitory effect Effects 0.000 abstract description 12
• 201000010099 disease Diseases 0.000 abstract description 9
• 230000001404 mediated effect Effects 0.000 abstract description 3
• 239000000203 mixture Substances 0.000 description 232
• 239000000243 solution Substances 0.000 description 205
• 238000005481 NMR spectroscopy Methods 0.000 description 154
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 130
• 239000011734 sodium Substances 0.000 description 129
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 122
• 239000007787 solid Substances 0.000 description 122
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 112
• 239000012044 organic layer Substances 0.000 description 106
• 239000012043 crude product Substances 0.000 description 103
• 239000000047 product Substances 0.000 description 95
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
• 239000002904 solvent Substances 0.000 description 90
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
• 239000011541 reaction mixture Substances 0.000 description 63
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 63
• 239000012267 brine Substances 0.000 description 55
• 239000004698 Polyethylene Substances 0.000 description 52
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
• 230000002829 reductive effect Effects 0.000 description 48
• 239000003480 eluent Substances 0.000 description 47
• 239000003921 oil Substances 0.000 description 43
• 235000019198 oils Nutrition 0.000 description 43
• 239000000706 filtrate Substances 0.000 description 40
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 39
• 238000000746 purification Methods 0.000 description 38
• 238000002953 preparative HPLC Methods 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
• 235000019439 ethyl acetate Nutrition 0.000 description 34
• 235000019253 formic acid Nutrition 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 30
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
• 101710136122 Tryptophan 2,3-dioxygenase Proteins 0.000 description 25
• 239000000741 silica gel Substances 0.000 description 25
• 229910002027 silica gel Inorganic materials 0.000 description 25
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• 238000004128 high performance liquid chromatography Methods 0.000 description 24
• 238000010898 silica gel chromatography Methods 0.000 description 24
• 102100040653 Tryptophan 2,3-dioxygenase Human genes 0.000 description 23
• 229910052938 sodium sulfate Inorganic materials 0.000 description 23
• 235000011152 sodium sulphate Nutrition 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
• 239000010410 layer Substances 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 238000004440 column chromatography Methods 0.000 description 21
• 238000003756 stirring Methods 0.000 description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
• 108010029485 Protein Isoforms Proteins 0.000 description 18
• 102000001708 Protein Isoforms Human genes 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• 238000001914 filtration Methods 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 17
• 239000003112 inhibitor Substances 0.000 description 17
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 17
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 16
• 239000000284 extract Substances 0.000 description 16
• 239000003208 petroleum Substances 0.000 description 16
• 238000012746 preparative thin layer chromatography Methods 0.000 description 16
• 238000003786 synthesis reaction Methods 0.000 description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
• 239000002244 precipitate Substances 0.000 description 15
• 230000000694 effects Effects 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 13
• 150000004795 grignard reagents Chemical class 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
• WMJMABVHDMRMJA-UHFFFAOYSA-M [Cl-].[Mg+]C1CCCCC1 Chemical compound [Cl-].[Mg+]C1CCCCC1 WMJMABVHDMRMJA-UHFFFAOYSA-M 0.000 description 12
• 239000012299 nitrogen atmosphere Substances 0.000 description 12
• 102000004190 Enzymes Human genes 0.000 description 11
• 108090000790 Enzymes Proteins 0.000 description 11
• 150000001299 aldehydes Chemical class 0.000 description 11
• 239000012141 concentrate Substances 0.000 description 11
• 235000008504 concentrate Nutrition 0.000 description 11
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 10
• 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 239000007864 aqueous solution Substances 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
• 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 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• 238000000926 separation method Methods 0.000 description 9
• 239000002246 antineoplastic agent Substances 0.000 description 8
• 125000002837 carbocyclic group Chemical group 0.000 description 8
• 229940044683 chemotherapy drug Drugs 0.000 description 8
• 125000004122 cyclic group Chemical group 0.000 description 8
• 150000002430 hydrocarbons Chemical group 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• 150000002576 ketones Chemical group 0.000 description 8
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
• ZGONBEYFIRPIIU-UHFFFAOYSA-N 6-chloroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound ClC=1C=CC=2N(C=1C=O)C=NC=2 ZGONBEYFIRPIIU-UHFFFAOYSA-N 0.000 description 7
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 7
• 239000007818 Grignard reagent Substances 0.000 description 7
• 241000725303 Human immunodeficiency virus Species 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 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 6
• 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 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 239000001569 carbon dioxide Substances 0.000 description 6
• 229910002092 carbon dioxide Inorganic materials 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 125000006413 ring segment Chemical group 0.000 description 6
• 238000004809 thin layer chromatography Methods 0.000 description 6
• SQFYMVPHDMIMHU-UHFFFAOYSA-N (4,6-dichloro-5-fluoropyridin-2-yl)methanol Chemical compound ClC1=CC(=NC(=C1F)Cl)CO SQFYMVPHDMIMHU-UHFFFAOYSA-N 0.000 description 5
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 5
• FJXHSIZXJIQTLW-UHFFFAOYSA-N 7-chloroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound ClC1=CC=2N(C(=C1)C=O)C=NC=2 FJXHSIZXJIQTLW-UHFFFAOYSA-N 0.000 description 5
• 241000124008 Mammalia Species 0.000 description 5
• 241000699670 Mus sp. Species 0.000 description 5
• 239000007832 Na2SO4 Substances 0.000 description 5
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
• 210000001744 T-lymphocyte Anatomy 0.000 description 5
• 210000004369 blood Anatomy 0.000 description 5
• 239000008280 blood Substances 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 239000003638 chemical reducing agent Substances 0.000 description 5
• 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 5
• JTPBTUUKUMKNHD-UHFFFAOYSA-N imidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound O=CC1=CC=CC2=CN=CN12 JTPBTUUKUMKNHD-UHFFFAOYSA-N 0.000 description 5
• GFTXWCQFWLOXAT-UHFFFAOYSA-M magnesium;cyclohexane;bromide Chemical compound [Mg+2].[Br-].C1CC[CH-]CC1 GFTXWCQFWLOXAT-UHFFFAOYSA-M 0.000 description 5
• KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 5
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 239000012279 sodium borohydride Substances 0.000 description 5
• 229910000033 sodium borohydride Inorganic materials 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 5
• XTLJJHGQACAZMS-UHFFFAOYSA-N 4-oxo-1h-pyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC(=O)C=C(C(O)=O)N1 XTLJJHGQACAZMS-UHFFFAOYSA-N 0.000 description 4
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
• OSIMIXRUTQYJDD-UHFFFAOYSA-N 6-bromoimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound BrC=1C=CC=2N(C=1C=O)C=NC=2 OSIMIXRUTQYJDD-UHFFFAOYSA-N 0.000 description 4
• ZDALDBZMOVTAHV-UHFFFAOYSA-N 8-chloroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound ClC=1C=2N(C(=CC=1)C=O)C=NC=2 ZDALDBZMOVTAHV-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 4
• 239000007821 HATU Substances 0.000 description 4
• 241000282412 Homo Species 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 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
• 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 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 4
• 102000057288 Tryptophan 2,3-dioxygenases Human genes 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 238000011225 antiretroviral therapy Methods 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• 229940125782 compound 2 Drugs 0.000 description 4
• 229940126214 compound 3 Drugs 0.000 description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• UBRNJYSCVHFYDB-UHFFFAOYSA-N ethyl 6-(chloromethyl)pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC(CCl)=N1 UBRNJYSCVHFYDB-UHFFFAOYSA-N 0.000 description 4
• 239000011737 fluorine Substances 0.000 description 4
• 229960002949 fluorouracil Drugs 0.000 description 4
• 239000007903 gelatin capsule Substances 0.000 description 4
• 230000014509 gene expression Effects 0.000 description 4
• 125000001188 haloalkyl group Chemical group 0.000 description 4
• 230000001506 immunosuppresive effect Effects 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
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 4
• 235000019359 magnesium stearate Nutrition 0.000 description 4
• 230000007246 mechanism Effects 0.000 description 4
• 229960000485 methotrexate Drugs 0.000 description 4
• 238000010172 mouse model Methods 0.000 description 4
• XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 4
• 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 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 239000007921 spray Substances 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 229940126585 therapeutic drug Drugs 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 4
• VKPNOXPHJHZQQR-UHFFFAOYSA-N (6-bromoimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound BrC=1C=CC=2N(C=1C(O)C1CCCCC1)C=NC=2 VKPNOXPHJHZQQR-UHFFFAOYSA-N 0.000 description 3
• PYHZHIKRWMJPAU-UHFFFAOYSA-N (7-chloro-6-fluoroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound ClC1=CC=2N(C(=C1F)CO)C=NC=2 PYHZHIKRWMJPAU-UHFFFAOYSA-N 0.000 description 3
• ZFGSKEMZCQZFMC-QGZVFWFLSA-N (R)-cyclohexyl-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)[C@@H](O)C1=C(C=CC=2N1C=NC=2)C1CC1 ZFGSKEMZCQZFMC-QGZVFWFLSA-N 0.000 description 3
• ZFGSKEMZCQZFMC-KRWDZBQOSA-N (S)-cyclohexyl-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)[C@H](O)C1=C(C=CC=2N1C=NC=2)C1CC1 ZFGSKEMZCQZFMC-KRWDZBQOSA-N 0.000 description 3
• MNUYLABZTVOVKM-UHFFFAOYSA-N 2-bicyclo[2.2.1]heptanyl-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C12C(CC(CC1)C2)C(O)C1=C(C=CC=2N1C=NC=2)C1CC1 MNUYLABZTVOVKM-UHFFFAOYSA-N 0.000 description 3
• LECOUYNLEHRUOU-UHFFFAOYSA-N 5-fluoro-1-oxidopyridin-1-ium-2-carboxylic acid Chemical compound OC(=O)c1ccc(F)c[n+]1[O-] LECOUYNLEHRUOU-UHFFFAOYSA-N 0.000 description 3
• JHFKXHUKNYFWJM-UHFFFAOYSA-N 6-chloro-5-fluoropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(F)C(Cl)=N1 JHFKXHUKNYFWJM-UHFFFAOYSA-N 0.000 description 3
• QNNQXODGAUBZMA-UHFFFAOYSA-N 6-cyclopropylimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound C1(CC1)C=1C=CC=2N(C=1C=O)C=NC=2 QNNQXODGAUBZMA-UHFFFAOYSA-N 0.000 description 3
• RZQKMZPIAQATHI-UHFFFAOYSA-N 7-(trifluoromethyl)imidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound FC(C1=CC=2N(C(=C1)C=O)C=NC=2)(F)F RZQKMZPIAQATHI-UHFFFAOYSA-N 0.000 description 3
• 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 3
• DSYAZWPFDOGOCF-UHFFFAOYSA-N 7-chloro-6-fluoroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound ClC1=CC=2N(C(=C1F)C=O)C=NC=2 DSYAZWPFDOGOCF-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
• MPONAPFARZGDTH-UHFFFAOYSA-N Cl.OS(O)=O Chemical compound Cl.OS(O)=O MPONAPFARZGDTH-UHFFFAOYSA-N 0.000 description 3
• 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 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
• OVBPIULPVIDEAO-LBPRGKRZSA-N Folic acid Natural products 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 3
• 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 3
• 208000031886 HIV Infections Diseases 0.000 description 3
• 208000037357 HIV infectious disease Diseases 0.000 description 3
• 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 3
• 241001465754 Metazoa Species 0.000 description 3
• 229930012538 Paclitaxel Natural products 0.000 description 3
• 241000713311 Simian immunodeficiency virus Species 0.000 description 3
• 241000700605 Viruses Species 0.000 description 3
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
• 239000000443 aerosol Substances 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 230000003042 antagnostic effect Effects 0.000 description 3
• 239000003242 anti bacterial agent Substances 0.000 description 3
• 230000000259 anti-tumor effect Effects 0.000 description 3
• 229940088710 antibiotic agent Drugs 0.000 description 3
• 210000000612 antigen-presenting cell Anatomy 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 229960000397 bevacizumab Drugs 0.000 description 3
• 239000006227 byproduct Substances 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 239000001913 cellulose Chemical class 0.000 description 3
• 229920002678 cellulose Chemical class 0.000 description 3
• 235000010980 cellulose Nutrition 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• SHDPLRDPXGMTPF-UHFFFAOYSA-N cyclohexyl(imidazo[1,5-a]pyridin-5-yl)methanone Chemical compound C1(CCCCC1)C(=O)C1=CC=CC=2N1C=NC=2 SHDPLRDPXGMTPF-UHFFFAOYSA-N 0.000 description 3
• 229960004397 cyclophosphamide Drugs 0.000 description 3
• WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 3
• 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 3
• ZQNBKZRLUKPGCF-UHFFFAOYSA-N diethyl 4-oxo-1h-pyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=CC(O)=CC(C(=O)OCC)=N1 ZQNBKZRLUKPGCF-UHFFFAOYSA-N 0.000 description 3
• VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 3
• LSUPUARVEHMMOM-UHFFFAOYSA-N ethyl 4-chloro-3-fluoro-6-(hydroxymethyl)pyridine-2-carboxylate Chemical compound ClC1=C(C(=NC(=C1)CO)C(=O)OCC)F LSUPUARVEHMMOM-UHFFFAOYSA-N 0.000 description 3
• CNKSDJBCIBYNGI-UHFFFAOYSA-N ethyl 6-(chloromethyl)-4-(trifluoromethyl)pyridine-2-carboxylate Chemical compound ClCC1=CC(=CC(=N1)C(=O)OCC)C(F)(F)F CNKSDJBCIBYNGI-UHFFFAOYSA-N 0.000 description 3
• RZOYFWXEDUBNRT-UHFFFAOYSA-N ethyl 7-chloroimidazo[1,5-a]pyridine-5-carboxylate Chemical compound ClC1=CC=2N(C(=C1)C(=O)OCC)C=NC=2 RZOYFWXEDUBNRT-UHFFFAOYSA-N 0.000 description 3
• 238000000605 extraction Methods 0.000 description 3
• 238000003818 flash chromatography Methods 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 229960003297 gemtuzumab ozogamicin Drugs 0.000 description 3
• 229940088597 hormone Drugs 0.000 description 3
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 3
• JDOXTBZIMSOYMJ-UHFFFAOYSA-N imidazo[1,5-a]pyridin-5-ylmethanol Chemical compound OCC1=CC=CC2=CN=CN12 JDOXTBZIMSOYMJ-UHFFFAOYSA-N 0.000 description 3
• 208000015181 infectious disease Diseases 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound 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 GURKHSYORGJETM-WAQYZQTGSA-N 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
• DEGPIRUPAKWDBU-UHFFFAOYSA-N isoindole-1,3-dione;sodium Chemical compound [Na].C1=CC=C2C(=O)NC(=O)C2=C1 DEGPIRUPAKWDBU-UHFFFAOYSA-N 0.000 description 3
• 239000008101 lactose Substances 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
• 239000008297 liquid dosage form Substances 0.000 description 3
• 239000011777 magnesium Substances 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• 229960004857 mitomycin Drugs 0.000 description 3
• 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 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 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 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 238000007254 oxidation reaction Methods 0.000 description 3
• 125000004430 oxygen atom Chemical group O* 0.000 description 3
• 229960001592 paclitaxel Drugs 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• 229960002087 pertuzumab Drugs 0.000 description 3
• 238000010791 quenching Methods 0.000 description 3
• 229940095743 selective estrogen receptor modulator Drugs 0.000 description 3
• 239000000333 selective estrogen receptor modulator Substances 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
• 239000003381 stabilizer Substances 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
• 229940124597 therapeutic agent Drugs 0.000 description 3
• 229960001196 thiotepa Drugs 0.000 description 3
• 229960003989 tocilizumab Drugs 0.000 description 3
• PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 3
• 210000004881 tumor cell Anatomy 0.000 description 3
• 229960005486 vaccine Drugs 0.000 description 3
• ZNRDASHAVJCWHR-UHFFFAOYSA-N (3-aminocyclohexyl)-(7-chloroimidazo[1,5-a]pyridin-5-yl)methanone Chemical compound NC1CC(CCC1)C(=O)C1=CC(=CC=2N1C=NC=2)Cl ZNRDASHAVJCWHR-UHFFFAOYSA-N 0.000 description 2
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
• SRKLLJCIDUPJMT-UHFFFAOYSA-N (6,7,8-trichloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound ClC=1C(=C(C=2N(C=1CO)C=NC=2)Cl)Cl SRKLLJCIDUPJMT-UHFFFAOYSA-N 0.000 description 2
• YQTKVPDGBGXFPD-UHFFFAOYSA-N (6,7-dichloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound ClC=1C(=CC=2N(C=1CO)C=NC=2)Cl YQTKVPDGBGXFPD-UHFFFAOYSA-N 0.000 description 2
• OEKYAYZOACSPAX-UHFFFAOYSA-N (6-chloro-7-fluoroimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound ClC=1C(=CC=2N(C=1C(O)C1CCCCC1)C=NC=2)F OEKYAYZOACSPAX-UHFFFAOYSA-N 0.000 description 2
• ZRBSTDVHZIFABH-UHFFFAOYSA-N (6-chloroimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound ClC=1C=CC=2N(C=1C(O)C1CCCCC1)C=NC=2 ZRBSTDVHZIFABH-UHFFFAOYSA-N 0.000 description 2
• AXLGWEZDWDQDMC-UHFFFAOYSA-N (6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CC1)C=1C=CC=2N(C=1CO)C=NC=2 AXLGWEZDWDQDMC-UHFFFAOYSA-N 0.000 description 2
• WTCVIQAHWZNUJO-UHFFFAOYSA-N (7-chloro-6-fluoroimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound ClC1=CC=2N(C(=C1F)C(O)C1CCCCC1)C=NC=2 WTCVIQAHWZNUJO-UHFFFAOYSA-N 0.000 description 2
• UULBVLNNOUUOFN-UHFFFAOYSA-N (7-chloroimidazo[1,5-a]pyridin-5-yl)-(4-methylcyclohexyl)methanol Chemical compound ClC1=CC=2N(C(=C1)C(O)C1CCC(CC1)C)C=NC=2 UULBVLNNOUUOFN-UHFFFAOYSA-N 0.000 description 2
• PMPZFWBFBPTVIB-UHFFFAOYSA-N (7-chloroimidazo[1,5-a]pyridin-5-yl)-(4-methylcyclohexyl)methanone Chemical compound ClC1=CC=2N(C(=C1)C(=O)C1CCC(CC1)C)C=NC=2 PMPZFWBFBPTVIB-UHFFFAOYSA-N 0.000 description 2
• AVJCRIIDMDBAQC-UHFFFAOYSA-N (7-chloroimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound ClC1=CC=2N(C(=C1)C(O)C1CCCCC1)C=NC=2 AVJCRIIDMDBAQC-UHFFFAOYSA-N 0.000 description 2
• ZKOSGFYBVUPTPQ-UHFFFAOYSA-N (7-chloroimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanone Chemical compound ClC1=CC=2N(C(=C1)C(=O)C1CCCCC1)C=NC=2 ZKOSGFYBVUPTPQ-UHFFFAOYSA-N 0.000 description 2
• ZAVPEPGQGXRVAD-UHFFFAOYSA-N (7-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CC1)C1=CC=2N(C(=C1)CO)C=NC=2 ZAVPEPGQGXRVAD-UHFFFAOYSA-N 0.000 description 2
• KSSYVHIFUXVVFW-UHFFFAOYSA-N (8-chloro-7-methoxyimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound ClC=1C=2N(C(=CC=1OC)C(O)C1CCCCC1)C=NC=2 KSSYVHIFUXVVFW-UHFFFAOYSA-N 0.000 description 2
• FQTUQYYTFPMBPH-UHFFFAOYSA-N (8-chloro-7-methoxyimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound ClC=1C=2N(C(=CC=1OC)CO)C=NC=2 FQTUQYYTFPMBPH-UHFFFAOYSA-N 0.000 description 2
• IWHORECPTSDDFT-UHFFFAOYSA-N (8-chloroimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound ClC=1C=2N(C(=CC=1)C(O)C1CCCCC1)C=NC=2 IWHORECPTSDDFT-UHFFFAOYSA-N 0.000 description 2
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 2
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
• OHOXMCCFSFSRMD-UHFFFAOYSA-N 1,3-oxathiole Chemical compound C1OC=CS1 OHOXMCCFSFSRMD-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• 125000005960 1,4-diazepanyl group Chemical group 0.000 description 2
• UVRYFDDVYSSVGE-UHFFFAOYSA-N 1-(6-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylpropan-1-ol Chemical compound ClC=1C=CC=2N(C=1C(C(C)C1CCCCC1)O)C=NC=2 UVRYFDDVYSSVGE-UHFFFAOYSA-N 0.000 description 2
• IYMYHZHCOOWPGK-UHFFFAOYSA-N 1-chloro-n,n-dimethylmethanamine Chemical compound CN(C)CCl IYMYHZHCOOWPGK-UHFFFAOYSA-N 0.000 description 2
• FKVXIRJVRIOURS-UHFFFAOYSA-N 1-chloropyrrolidine-2,5-dione Chemical compound ClN1C(=O)CCC1=O.ClN1C(=O)CCC1=O FKVXIRJVRIOURS-UHFFFAOYSA-N 0.000 description 2
• BSIWCSTWBWSRFY-UHFFFAOYSA-N 1-imidazo[1,5-a]pyridin-5-yl-2-methylpropan-1-ol Chemical compound C=1N=CN2C=1C=CC=C2C(C(C)C)O BSIWCSTWBWSRFY-UHFFFAOYSA-N 0.000 description 2
• ZADWXFSZEAPBJS-UHFFFAOYSA-N 1-methyltryptophan Chemical compound C1=CC=C2N(C)C=C(CC(N)C(O)=O)C2=C1 ZADWXFSZEAPBJS-UHFFFAOYSA-N 0.000 description 2
• DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 2
• 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 2
• QCXJFISCRQIYID-IAEPZHFASA-N 2-amino-1-n-[(3s,6s,7r,10s,16s)-3-[(2s)-butan-2-yl]-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-10-propan-2-yl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-4,6-dimethyl-3-oxo-9-n-[(3s,6s,7r,10s,16s)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propa 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=C2C(C(=O)N[C@@H]3C(=O)N[C@H](C(N4CCC[C@H]4C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]3C)=O)[C@@H](C)CC)=C(N)C(=O)C(C)=C2O2)C2=C(C)C=C1 QCXJFISCRQIYID-IAEPZHFASA-N 0.000 description 2
• ODXHXCNWJKXWMW-UHFFFAOYSA-N 2-cyclohexyl-1-(6-iodoimidazo[1,5-a]pyridin-5-yl)ethanol Chemical compound C1(CCCCC1)CC(O)C1=C(C=CC=2N1C=NC=2)I ODXHXCNWJKXWMW-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
• 125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
• XURUUBHSFLXZGI-UHFFFAOYSA-N 3-[(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]benzoic acid Chemical compound C1(CC1)C=1C=CC=2N(C=1C(C=1C=C(C(=O)O)C=CC=1)O)C=NC=2 XURUUBHSFLXZGI-UHFFFAOYSA-N 0.000 description 2
• PUMRSXPCFHVQSD-UHFFFAOYSA-N 3-chloro-N-[3-(7-chloroimidazo[1,5-a]pyridine-5-carbonyl)cyclohexyl]benzamide Chemical compound ClC=1C=C(C(=O)NC2CC(CCC2)C(=O)C2=CC(=CC=3N2C=NC=3)Cl)C=CC=1 PUMRSXPCFHVQSD-UHFFFAOYSA-N 0.000 description 2
• OXUXKUBAFKLBHK-UHFFFAOYSA-N 3-chloro-N-[3-[(7-chloroimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]cyclohexyl]benzamide Chemical compound ClC=1C=C(C(=O)NC2CC(CCC2)C(O)C2=CC(=CC=3N2C=NC=3)Cl)C=CC=1 OXUXKUBAFKLBHK-UHFFFAOYSA-N 0.000 description 2
• WZPVVRDNZMLLFM-UHFFFAOYSA-N 3-cyclopropyl-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridine-2-carboxylic acid Chemical compound C(C)(C)(C)OC(=O)NCC1=CC=C(C(=N1)C(=O)O)C1CC1 WZPVVRDNZMLLFM-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
• 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 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• FTIJEMGBMVTYPY-UHFFFAOYSA-N 4-[(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]cyclohexan-1-ol Chemical compound C1(CC1)C=1C=CC=2N(C=1C(C1CCC(CC1)O)O)C=NC=2 FTIJEMGBMVTYPY-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 2
• 125000001054 5 membered carbocyclic group Chemical group 0.000 description 2
• MBQIMNGUGNWDED-UHFFFAOYSA-N 5-(cyclohexylmethyl)imidazo[1,5-a]pyridine Chemical compound C1(CCCCC1)CC1=CC=CC=2N1C=NC=2 MBQIMNGUGNWDED-UHFFFAOYSA-N 0.000 description 2
• BEDULBGFLDHTSH-UHFFFAOYSA-N 5-chloro-6-(chloromethyl)pyridine-2-carbonitrile Chemical compound ClC=1C=CC(=NC=1CCl)C#N BEDULBGFLDHTSH-UHFFFAOYSA-N 0.000 description 2
• JEBATZXFCROAFT-UHFFFAOYSA-N 5-chloro-6-(hydroxymethyl)pyridine-2-carbonitrile Chemical compound ClC=1C=CC(=NC=1CO)C#N JEBATZXFCROAFT-UHFFFAOYSA-N 0.000 description 2
• 125000004008 6 membered carbocyclic group Chemical group 0.000 description 2
• KRPQPDMWYRDFED-UHFFFAOYSA-N 6,7,8-trichloroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound ClC=1C(=C(C=2N(C=1C=O)C=NC=2)Cl)Cl KRPQPDMWYRDFED-UHFFFAOYSA-N 0.000 description 2
• OGFOIJXFYKHCTD-UHFFFAOYSA-N 6,7-dichloroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound ClC=1C(=CC=2N(C=1C=O)C=NC=2)Cl OGFOIJXFYKHCTD-UHFFFAOYSA-N 0.000 description 2
• SVTOJJZCKVQRIX-UHFFFAOYSA-N 6-(aminomethyl)-5-chloropyridine-2-carbonitrile Chemical compound NCC1=C(C=CC(=N1)C#N)Cl SVTOJJZCKVQRIX-UHFFFAOYSA-N 0.000 description 2
• ANNOSVXLLDXIAC-UHFFFAOYSA-N 6-chloro-5-fluoro-1-oxidopyridin-1-ium-2-carboxylic acid Chemical compound C(=O)(O)C1=CC=C(C(=[N+]1[O-])Cl)F ANNOSVXLLDXIAC-UHFFFAOYSA-N 0.000 description 2
• 229960005538 6-diazo-5-oxo-L-norleucine Drugs 0.000 description 2
• 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 2
• JGBAXSWPULRLCX-UHFFFAOYSA-N 6-iodoimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound IC=1C=CC=2N(C=1C=O)C=NC=2 JGBAXSWPULRLCX-UHFFFAOYSA-N 0.000 description 2
• NTCSRBLWDMZKBJ-UHFFFAOYSA-N 7-chloro-5-(cyclohexylmethyl)imidazo[1,5-a]pyridine Chemical compound ClC1=CC=2N(C(=C1)CC1CCCCC1)C=NC=2 NTCSRBLWDMZKBJ-UHFFFAOYSA-N 0.000 description 2
• XCWWUBZSQJFNPD-UHFFFAOYSA-N 7-chloro-N-methoxy-N-methylimidazo[1,5-a]pyridine-5-carboxamide Chemical compound ClC1=CC=2N(C(=C1)C(=O)N(C)OC)C=NC=2 XCWWUBZSQJFNPD-UHFFFAOYSA-N 0.000 description 2
• GUMLZFNJLHIATM-UHFFFAOYSA-N 7-chloroimidazo[1,5-a]pyridine-5-carboxylic acid Chemical compound ClC1=CC=2N(C(=C1)C(=O)O)C=NC=2 GUMLZFNJLHIATM-UHFFFAOYSA-N 0.000 description 2
• AYKKYNJHOQOBTD-UHFFFAOYSA-N 7-cyclopropylimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound C1(CC1)C1=CC=2N(C(=C1)C=O)C=NC=2 AYKKYNJHOQOBTD-UHFFFAOYSA-N 0.000 description 2
• QUMINRSAHMUVHF-UHFFFAOYSA-N 8-chloro-7-methoxyimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound ClC=1C=2N(C(=CC=1OC)C=O)C=NC=2 QUMINRSAHMUVHF-UHFFFAOYSA-N 0.000 description 2
• ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 108020000948 Antisense Oligonucleotides Proteins 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 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
• 208000023275 Autoimmune disease Diseases 0.000 description 2
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-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
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
• 239000004342 Benzoyl peroxide Substances 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
• QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 description 2
• 206010006895 Cachexia Diseases 0.000 description 2
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-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
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
• SHHKQEUPHAENFK-UHFFFAOYSA-N Carboquone Chemical compound O=C1C(C)=C(N2CC2)C(=O)C(C(COC(N)=O)OC)=C1N1CC1 SHHKQEUPHAENFK-UHFFFAOYSA-N 0.000 description 2
• 108090000994 Catalytic RNA Proteins 0.000 description 2
• 102000053642 Catalytic RNA Human genes 0.000 description 2
• 241000282693 Cercopithecidae Species 0.000 description 2
• 229910052684 Cerium Inorganic materials 0.000 description 2
• 206010012289 Dementia Diseases 0.000 description 2
• 206010012735 Diarrhoea Diseases 0.000 description 2
• 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 2
• 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 2
• 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 2
• 206010062016 Immunosuppression Diseases 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 description 2
• 239000005551 L01XE03 - Erlotinib Substances 0.000 description 2
• 239000002147 L01XE04 - Sunitinib Substances 0.000 description 2
• 239000005511 L01XE05 - Sorafenib Substances 0.000 description 2
• 239000002136 L01XE07 - Lapatinib Substances 0.000 description 2
• GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 229930192392 Mitomycin Natural products 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
• VIUAUNHCRHHYNE-JTQLQIEISA-N N-[(2S)-2,3-dihydroxypropyl]-3-(2-fluoro-4-iodoanilino)-4-pyridinecarboxamide Chemical compound OC[C@@H](O)CNC(=O)C1=CC=NC=C1NC1=CC=C(I)C=C1F VIUAUNHCRHHYNE-JTQLQIEISA-N 0.000 description 2
• ZOLIMIKWFYUOSA-UHFFFAOYSA-N N-[(3-chloro-6-cyanopyridin-2-yl)methyl]formamide Chemical compound C(=O)NCC1=NC(=CC=C1Cl)C#N ZOLIMIKWFYUOSA-UHFFFAOYSA-N 0.000 description 2
• PWCKMJUAQKRDLP-UHFFFAOYSA-N N-cyclopropyl-3-[(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]benzamide Chemical compound C1(CC1)NC(C1=CC(=CC=C1)C(O)C1=C(C=CC=2N1C=NC=2)C1CC1)=O PWCKMJUAQKRDLP-UHFFFAOYSA-N 0.000 description 2
• AIWVQLKBFYYHGZ-UHFFFAOYSA-N N-methoxy-N-methylimidazo[1,5-a]pyridine-5-carboxamide Chemical compound CON(C(=O)C1=CC=CC=2N1C=NC=2)C AIWVQLKBFYYHGZ-UHFFFAOYSA-N 0.000 description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• 235000019502 Orange oil Nutrition 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• 229920002472 Starch Chemical class 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
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• 108700016257 Tryptophan 2,3-dioxygenases Proteins 0.000 description 2
• 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 2
• YINLBFRXHPGKRH-DQZJLYPMSA-N [6-(aminomethyl)-3-cyclopropylpyridin-2-yl]-[(1R,4S)-2-bicyclo[2.2.1]heptanyl]methanol hydrochloride Chemical compound Cl.NCc1ccc(C2CC2)c(n1)C(O)C1C[C@H]2CC[C@@H]1C2 YINLBFRXHPGKRH-DQZJLYPMSA-N 0.000 description 2
• HDZQCOSVUAZSFA-UHFFFAOYSA-N [7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound FC(C1=CC=2N(C(=C1)CO)C=NC=2)(F)F HDZQCOSVUAZSFA-UHFFFAOYSA-N 0.000 description 2
• KMAQJJKRGAFLBH-UHFFFAOYSA-M [Br-].[Mg+]C1CCCCCC1 Chemical compound [Br-].[Mg+]C1CCCCCC1 KMAQJJKRGAFLBH-UHFFFAOYSA-M 0.000 description 2
• ZBCIOGFGZRNNEC-UHFFFAOYSA-M [Br-].[Mg+]CC1CCCCC1 Chemical compound [Br-].[Mg+]CC1CCCCC1 ZBCIOGFGZRNNEC-UHFFFAOYSA-M 0.000 description 2
• ZOZKYEHVNDEUCO-XUTVFYLZSA-N aceglatone Chemical compound O1C(=O)[C@H](OC(C)=O)[C@@H]2OC(=O)[C@@H](OC(=O)C)[C@@H]21 ZOZKYEHVNDEUCO-XUTVFYLZSA-N 0.000 description 2
• 229950002684 aceglatone Drugs 0.000 description 2
• CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 229940009456 adriamycin Drugs 0.000 description 2
• 230000001476 alcoholic effect Effects 0.000 description 2
• 229960000548 alemtuzumab Drugs 0.000 description 2
• 125000002355 alkine group Chemical group 0.000 description 2
• 229940100198 alkylating agent Drugs 0.000 description 2
• 239000002168 alkylating agent Substances 0.000 description 2
• 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 2
• 229960000473 altretamine Drugs 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
• 229960002749 aminolevulinic acid Drugs 0.000 description 2
• 229960003896 aminopterin Drugs 0.000 description 2
• 229960001830 amprenavir Drugs 0.000 description 2
• YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 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
• 230000000340 anti-metabolite Effects 0.000 description 2
• 230000000798 anti-retroviral effect Effects 0.000 description 2
• 229940100197 antimetabolite Drugs 0.000 description 2
• 239000002256 antimetabolite Substances 0.000 description 2
• 229940041181 antineoplastic drug Drugs 0.000 description 2
• 239000000074 antisense oligonucleotide Substances 0.000 description 2
• 238000012230 antisense oligonucleotides Methods 0.000 description 2
• 239000012298 atmosphere Substances 0.000 description 2
• 229940120638 avastin Drugs 0.000 description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
• 235000019400 benzoyl peroxide Nutrition 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
• 210000004556 brain Anatomy 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 125000001246 bromo group Chemical group Br* 0.000 description 2
• 229960002092 busulfan Drugs 0.000 description 2
• 108700002839 cactinomycin Proteins 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• 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 2
• 229940127093 camptothecin Drugs 0.000 description 2
• 239000003560 cancer drug Substances 0.000 description 2
• 229960002115 carboquone Drugs 0.000 description 2
• 230000015556 catabolic process Effects 0.000 description 2
• GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 2
• 229960005395 cetuximab Drugs 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 239000008119 colloidal silica Substances 0.000 description 2
• 229940125904 compound 1 Drugs 0.000 description 2
• 239000007891 compressed tablet Substances 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• 239000006071 cream Substances 0.000 description 2
• 239000000287 crude extract Substances 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
• MHPBLJWAAANDQV-UHFFFAOYSA-N cyclohexyl(imidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=CC=CC=2N1C=NC=2 MHPBLJWAAANDQV-UHFFFAOYSA-N 0.000 description 2
• FPESKONNPZTTDS-UHFFFAOYSA-N cyclohexyl-(6,7,8-trichloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C(=C(C=2N1C=NC=2)Cl)Cl)Cl FPESKONNPZTTDS-UHFFFAOYSA-N 0.000 description 2
• QVABKTKOARCFMU-UHFFFAOYSA-N cyclohexyl-(6,7-dichloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C(=CC=2N1C=NC=2)Cl)Cl QVABKTKOARCFMU-UHFFFAOYSA-N 0.000 description 2
• ZFGSKEMZCQZFMC-UHFFFAOYSA-N cyclohexyl-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C1CC1 ZFGSKEMZCQZFMC-UHFFFAOYSA-N 0.000 description 2
• LJKPWGBUHBPLPO-UHFFFAOYSA-N cyclohexyl-(6-ethynylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C#C LJKPWGBUHBPLPO-UHFFFAOYSA-N 0.000 description 2
• VPYJIGSXXIHZIF-UHFFFAOYSA-N cyclohexyl-(6-methoxyimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)OC VPYJIGSXXIHZIF-UHFFFAOYSA-N 0.000 description 2
• IYYZKLHOMUWYNC-UHFFFAOYSA-N cyclohexyl-(6-methylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C IYYZKLHOMUWYNC-UHFFFAOYSA-N 0.000 description 2
• CQRPMHPDEXNZEL-UHFFFAOYSA-N cyclohexyl-(7-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(C1CCCCC1)c1cc(cc2cncn12)C1CC1 CQRPMHPDEXNZEL-UHFFFAOYSA-N 0.000 description 2
• BDUPBGPRKZNLCC-UHFFFAOYSA-N cyclohexyl-(8-fluoroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=CC=C(C=2N1C=NC=2)F BDUPBGPRKZNLCC-UHFFFAOYSA-N 0.000 description 2
• ORHZLQNWHGTNAU-UHFFFAOYSA-N cyclohexyl-[6-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C(F)(F)F ORHZLQNWHGTNAU-UHFFFAOYSA-N 0.000 description 2
• IZRXNSNERORBJM-UHFFFAOYSA-N cyclohexyl-[7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CCCCC1)C(O)C1=CC(=CC=2N1C=NC=2)C(F)(F)F IZRXNSNERORBJM-UHFFFAOYSA-N 0.000 description 2
• 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 2
• ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
• 229960000684 cytarabine Drugs 0.000 description 2
• OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
• 229960003901 dacarbazine Drugs 0.000 description 2
• 229960000975 daunorubicin Drugs 0.000 description 2
• 238000006731 degradation reaction Methods 0.000 description 2
• 210000004443 dendritic cell Anatomy 0.000 description 2
• 229950003913 detorubicin Drugs 0.000 description 2
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• 239000006185 dispersion Substances 0.000 description 2
• 229950010030 dl-alanine Drugs 0.000 description 2
• 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 2
• ZWAOHEXOSAUJHY-ZIYNGMLESA-N doxifluridine Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ZWAOHEXOSAUJHY-ZIYNGMLESA-N 0.000 description 2
• 229950005454 doxifluridine Drugs 0.000 description 2
• 229960004679 doxorubicin Drugs 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 229960002224 eculizumab Drugs 0.000 description 2
• 229960000284 efalizumab Drugs 0.000 description 2
• 150000002085 enols Chemical group 0.000 description 2
• 229960001904 epirubicin Drugs 0.000 description 2
• 229930013356 epothilone Natural products 0.000 description 2
• 150000003883 epothilone derivatives Chemical class 0.000 description 2
• 229950009760 epratuzumab Drugs 0.000 description 2
• 229950004292 erlizumab Drugs 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
• 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 2
• 229950002017 esorubicin Drugs 0.000 description 2
• XJTLIRSTWOKELH-UHFFFAOYSA-N ethyl 3,4,5-trichloro-6-(chloromethyl)pyridine-2-carboxylate Chemical compound ClC=1C(=NC(=C(C=1Cl)Cl)CCl)C(=O)OCC XJTLIRSTWOKELH-UHFFFAOYSA-N 0.000 description 2
• MXRGLEBNKYIPJP-UHFFFAOYSA-N ethyl 3-chloro-6-cyanopyridine-2-carboxylate Chemical compound CCOC(=O)C1=NC(C#N)=CC=C1Cl MXRGLEBNKYIPJP-UHFFFAOYSA-N 0.000 description 2
• KUPKFLRDBIHMMQ-UHFFFAOYSA-N ethyl 3-cyclopropyl-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridine-2-carboxylate Chemical compound C(C)(C)(C)OC(=O)NCC1=CC=C(C(=N1)C(=O)OCC)C1CC1 KUPKFLRDBIHMMQ-UHFFFAOYSA-N 0.000 description 2
• VYTSZQGSTKLWKU-UHFFFAOYSA-N ethyl 4-chloro-6-(chloromethyl)-3-fluoropyridine-2-carboxylate Chemical compound ClC1=C(C(=NC(=C1)CCl)C(=O)OCC)F VYTSZQGSTKLWKU-UHFFFAOYSA-N 0.000 description 2
• PALOQKODXOGXDG-UHFFFAOYSA-N ethyl 4-chloro-6-(chloromethyl)pyridine-2-carboxylate Chemical compound ClC1=CC(=NC(=C1)CCl)C(=O)OCC PALOQKODXOGXDG-UHFFFAOYSA-N 0.000 description 2
• FGDDWTGLRVCRMR-UHFFFAOYSA-N ethyl 4-chloro-6-(hydroxymethyl)pyridine-2-carboxylate Chemical compound ClC1=CC(=NC(=C1)CO)C(=O)OCC FGDDWTGLRVCRMR-UHFFFAOYSA-N 0.000 description 2
• BBWMASBANDIFMV-UHFFFAOYSA-N ethyl 4-phenylpiperidine-4-carboxylate;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C1(C(=O)OCC)CC[NH2+]CC1 BBWMASBANDIFMV-UHFFFAOYSA-N 0.000 description 2
• NQTARJCUVORZPI-UHFFFAOYSA-N ethyl 5-chloro-6-(chloromethyl)-4-methoxypyridine-2-carboxylate Chemical compound ClC=1C(=CC(=NC=1CCl)C(=O)OCC)OC NQTARJCUVORZPI-UHFFFAOYSA-N 0.000 description 2
• OLLDUACCUYKJKB-UHFFFAOYSA-N ethyl 6-(aminomethyl)-3,4-dichloropyridine-2-carboxylate Chemical compound NCC1=CC(=C(C(=N1)C(=O)OCC)Cl)Cl OLLDUACCUYKJKB-UHFFFAOYSA-N 0.000 description 2
• FWGFGSRDFMJNOV-UHFFFAOYSA-N ethyl 6-(aminomethyl)-4-(trifluoromethyl)pyridine-2-carboxylate Chemical compound NCC1=CC(=CC(=N1)C(=O)OCC)C(F)(F)F FWGFGSRDFMJNOV-UHFFFAOYSA-N 0.000 description 2
• NHGVACQSZQKADA-UHFFFAOYSA-N ethyl 6-(aminomethyl)-4-chloro-3-fluoropyridine-2-carboxylate Chemical compound NCC1=CC(=C(C(=N1)C(=O)OCC)F)Cl NHGVACQSZQKADA-UHFFFAOYSA-N 0.000 description 2
• SUKUWPXNWKYGIP-UHFFFAOYSA-N ethyl 6-(aminomethyl)-4-chloropyridine-2-carboxylate Chemical compound NCC1=CC(=CC(=N1)C(=O)OCC)Cl SUKUWPXNWKYGIP-UHFFFAOYSA-N 0.000 description 2
• CUYOZUJLZMYCOX-UHFFFAOYSA-N ethyl 6-(aminomethyl)-5-chloro-4-methoxypyridine-2-carboxylate Chemical compound NCC1=C(C(=CC(=N1)C(=O)OCC)OC)Cl CUYOZUJLZMYCOX-UHFFFAOYSA-N 0.000 description 2
• FUYMGBVFYPKQJL-UHFFFAOYSA-N ethyl 6-(hydroxymethyl)-4-(trifluoromethyl)pyridine-2-carboxylate Chemical compound OCC1=CC(=CC(=N1)C(=O)OCC)C(F)(F)F FUYMGBVFYPKQJL-UHFFFAOYSA-N 0.000 description 2
• CDFOARSBQKJGNL-UHFFFAOYSA-N ethyl 6-(hydroxymethyl)pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC(CO)=N1 CDFOARSBQKJGNL-UHFFFAOYSA-N 0.000 description 2
• HRFKZDICUSLFFK-UHFFFAOYSA-N ethyl 6-chloro-7-fluoroimidazo[1,5-a]pyridine-5-carboxylate Chemical compound ClC=1C(=CC=2N(C=1C(=O)OCC)C=NC=2)F HRFKZDICUSLFFK-UHFFFAOYSA-N 0.000 description 2
• IDNIDMPRTPDZFH-UHFFFAOYSA-N ethyl 7-(trifluoromethyl)imidazo[1,5-a]pyridine-5-carboxylate Chemical compound FC(C1=CC=2N(C(=C1)C(=O)OCC)C=NC=2)(F)F IDNIDMPRTPDZFH-UHFFFAOYSA-N 0.000 description 2
• KPRMOIZQUWXNQJ-UHFFFAOYSA-N ethyl 7-chloro-6-fluoroimidazo[1,5-a]pyridine-5-carboxylate Chemical compound ClC1=CC=2N(C(=C1F)C(=O)OCC)C=NC=2 KPRMOIZQUWXNQJ-UHFFFAOYSA-N 0.000 description 2
• TZKGIBZLPGAGCH-UHFFFAOYSA-N ethyl 7-cyclopropylimidazo[1,5-a]pyridine-5-carboxylate Chemical compound C1(CC1)C1=CC=2N(C(=C1)C(=O)OCC)C=NC=2 TZKGIBZLPGAGCH-UHFFFAOYSA-N 0.000 description 2
• 229940087476 femara Drugs 0.000 description 2
• 239000012065 filter cake Substances 0.000 description 2
• 229960000390 fludarabine Drugs 0.000 description 2
• 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 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
• 239000012458 free base Substances 0.000 description 2
• 229960002258 fulvestrant Drugs 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
• 238000001415 gene therapy Methods 0.000 description 2
• 229930182470 glycoside Natural products 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
• 125000005843 halogen group Chemical group 0.000 description 2
• UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 2
• ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
• 239000005556 hormone Substances 0.000 description 2
• 150000007857 hydrazones Chemical class 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 229960000908 idarubicin Drugs 0.000 description 2
• 229960001101 ifosfamide Drugs 0.000 description 2
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 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
• XJQJTCAEHKHHJM-UHFFFAOYSA-N imidazo[1,5-a]pyridin-5-yl(phenyl)methanol Chemical compound C=1N=CN2C=1C=CC=C2C(O)C1=CC=CC=C1 XJQJTCAEHKHHJM-UHFFFAOYSA-N 0.000 description 2
• AWWQOKTUOLEQGD-UHFFFAOYSA-N imidazo[1,5-a]pyridine-5-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=CN=CN12 AWWQOKTUOLEQGD-UHFFFAOYSA-N 0.000 description 2
• DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 2
• 229950008097 improsulfan Drugs 0.000 description 2
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
• CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 2
• 229960001936 indinavir Drugs 0.000 description 2
• 125000000842 isoxazolyl group Chemical group 0.000 description 2
• 229940043355 kinase inhibitor Drugs 0.000 description 2
• HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 description 2
• YGPSJZOEDVAXAB-UHFFFAOYSA-N kynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-UHFFFAOYSA-N 0.000 description 2
• 150000002596 lactones Chemical class 0.000 description 2
• 229960003881 letrozole Drugs 0.000 description 2
• 229950002950 lintuzumab Drugs 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 229960002247 lomustine Drugs 0.000 description 2
• 229960004525 lopinavir Drugs 0.000 description 2
• 210000002540 macrophage Anatomy 0.000 description 2
• 229960004961 mechlorethamine Drugs 0.000 description 2
• HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 229960004296 megestrol acetate Drugs 0.000 description 2
• 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 2
• RXZGRUWPQKNKEA-UHFFFAOYSA-N methyl 3-[(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]benzoate Chemical compound C1(CC1)C=1C=CC=2N(C=1C(C=1C=C(C(=O)OC)C=CC=1)O)C=NC=2 RXZGRUWPQKNKEA-UHFFFAOYSA-N 0.000 description 2
• FOYANJQYXKGDKP-UHFFFAOYSA-N methyl 6-chloro-5-fluoro-1-oxidopyridin-1-ium-2-carboxylate Chemical compound ClC1=[N+](C(=CC=C1F)C(=O)OC)[O-] FOYANJQYXKGDKP-UHFFFAOYSA-N 0.000 description 2
• LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
• 229960001156 mitoxantrone Drugs 0.000 description 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
• 210000004985 myeloid-derived suppressor cell Anatomy 0.000 description 2
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
• 125000001624 naphthyl group Chemical group 0.000 description 2
• QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 description 2
• 229960000884 nelfinavir Drugs 0.000 description 2
• QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 description 2
• 229950010203 nimotuzumab Drugs 0.000 description 2
• VFEDRRNHLBGPNN-UHFFFAOYSA-N nimustine Chemical compound CC1=NC=C(CNC(=O)N(CCCl)N=O)C(N)=N1 VFEDRRNHLBGPNN-UHFFFAOYSA-N 0.000 description 2
• 229960001420 nimustine Drugs 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• 239000010502 orange oil Substances 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 239000012074 organic phase Substances 0.000 description 2
• 125000003566 oxetanyl group Chemical group 0.000 description 2
• 229940097411 palm acid Drugs 0.000 description 2
• 229960001972 panitumumab Drugs 0.000 description 2
• 238000007911 parenteral administration Methods 0.000 description 2
• 239000003182 parenteral nutrition solution Substances 0.000 description 2
• 239000012071 phase Substances 0.000 description 2
• 229950002592 pimasertib Drugs 0.000 description 2
• NUKCGLDCWQXYOQ-UHFFFAOYSA-N piposulfan Chemical compound CS(=O)(=O)OCCC(=O)N1CCN(C(=O)CCOS(C)(=O)=O)CC1 NUKCGLDCWQXYOQ-UHFFFAOYSA-N 0.000 description 2
• 229950001100 piposulfan Drugs 0.000 description 2
• 210000002826 placenta Anatomy 0.000 description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
• 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 2
• 229950010131 puromycin Drugs 0.000 description 2
• 125000004076 pyridyl 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
• 229930002330 retinoic acid Natural products 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• 108091092562 ribozyme Proteins 0.000 description 2
• 229960004641 rituximab Drugs 0.000 description 2
• 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 2
• CYOHGALHFOKKQC-UHFFFAOYSA-N selumetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1Cl CYOHGALHFOKKQC-UHFFFAOYSA-N 0.000 description 2
• 229950008684 sibrotuzumab Drugs 0.000 description 2
• 239000000377 silicon dioxide Substances 0.000 description 2
• 229960002930 sirolimus Drugs 0.000 description 2
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
• 239000008107 starch Chemical class 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-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
• 229960001052 streptozocin Drugs 0.000 description 2
• 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 2
• 239000000126 substance Substances 0.000 description 2
• 238000013268 sustained release Methods 0.000 description 2
• 239000012730 sustained-release form 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
• WRTRYTOHSPXFGQ-UHFFFAOYSA-N tert-butyl N-[3-(7-chloroimidazo[1,5-a]pyridine-5-carbonyl)cyclohexyl]carbamate Chemical compound ClC1=CC=2N(C(=C1)C(=O)C1CC(CCC1)NC(OC(C)(C)C)=O)C=NC=2 WRTRYTOHSPXFGQ-UHFFFAOYSA-N 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• 238000011200 topical administration Methods 0.000 description 2
• 229960000303 topotecan Drugs 0.000 description 2
• 229950001802 toralizumab Drugs 0.000 description 2
• 229960005267 tositumomab Drugs 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• LIRYPHYGHXZJBZ-UHFFFAOYSA-N trametinib Chemical compound CC(=O)NC1=CC=CC(N2C(N(C3CC3)C(=O)C3=C(NC=4C(=CC(I)=CC=4)F)N(C)C(=O)C(C)=C32)=O)=C1 LIRYPHYGHXZJBZ-UHFFFAOYSA-N 0.000 description 2
• 230000009466 transformation Effects 0.000 description 2
• 238000000844 transformation Methods 0.000 description 2
• 238000002054 transplantation Methods 0.000 description 2
• 229960000575 trastuzumab Drugs 0.000 description 2
• IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 2
• 229950001353 tretamine Drugs 0.000 description 2
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
• NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 2
• 229960001099 trimetrexate Drugs 0.000 description 2
• 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 2
• 230000004614 tumor growth Effects 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
• DNZYTNFLPGMEHH-CQSZACIVSA-N (1R)-1-(6-bromoimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound BrC=1C=CC=2N(C=1[C@@H](CC1CCCCC1)O)C=NC=2 DNZYTNFLPGMEHH-CQSZACIVSA-N 0.000 description 1
• DJRKEAJZPFKVTE-CQSZACIVSA-N (1R)-1-(6-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound ClC=1C=CC=2N(C=1[C@@H](CC1CCCCC1)O)C=NC=2 DJRKEAJZPFKVTE-CQSZACIVSA-N 0.000 description 1
• UKUFLIABWYMYJX-OAHLLOKOSA-N (1R)-1-(7-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound ClC1=CC=2N(C(=C1)[C@@H](CC1CCCCC1)O)C=NC=2 UKUFLIABWYMYJX-OAHLLOKOSA-N 0.000 description 1
• DXJCNDCTIWOTLE-CYBMUJFWSA-N (1R)-2-cyclohexyl-1-(6,7-dichloroimidazo[1,5-a]pyridin-5-yl)ethanol Chemical compound C1(CCCCC1)C[C@@H](O)C1=C(C(=CC=2N1C=NC=2)Cl)Cl DXJCNDCTIWOTLE-CYBMUJFWSA-N 0.000 description 1
• ODXHXCNWJKXWMW-CQSZACIVSA-N (1R)-2-cyclohexyl-1-(6-iodoimidazo[1,5-a]pyridin-5-yl)ethanol Chemical compound C1(CCCCC1)C[C@@H](O)C1=C(C=CC=2N1C=NC=2)I ODXHXCNWJKXWMW-CQSZACIVSA-N 0.000 description 1
• PAXACHHUUASAST-CQSZACIVSA-N (1R)-2-cyclohexyl-1-[6-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]ethanol Chemical compound C1(CCCCC1)C[C@@H](O)C1=C(C=CC=2N1C=NC=2)C(F)(F)F PAXACHHUUASAST-CQSZACIVSA-N 0.000 description 1
• ABMAVJAOLCPYCT-OAHLLOKOSA-N (1R)-2-cyclohexyl-1-[7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]ethanol Chemical compound C1(CCCCC1)C[C@@H](O)C1=CC(=CC=2N1C=NC=2)C(F)(F)F ABMAVJAOLCPYCT-OAHLLOKOSA-N 0.000 description 1
• DJRKEAJZPFKVTE-AWEZNQCLSA-N (1S)-1-(6-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound ClC=1C=CC=2N(C=1[C@H](CC1CCCCC1)O)C=NC=2 DJRKEAJZPFKVTE-AWEZNQCLSA-N 0.000 description 1
• ODXHXCNWJKXWMW-AWEZNQCLSA-N (1S)-2-cyclohexyl-1-(6-iodoimidazo[1,5-a]pyridin-5-yl)ethanol Chemical compound C1(CCCCC1)C[C@H](O)C1=C(C=CC=2N1C=NC=2)I ODXHXCNWJKXWMW-AWEZNQCLSA-N 0.000 description 1
• PAXACHHUUASAST-AWEZNQCLSA-N (1S)-2-cyclohexyl-1-[6-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]ethanol Chemical compound C1(CCCCC1)C[C@H](O)C1=C(C=CC=2N1C=NC=2)C(F)(F)F PAXACHHUUASAST-AWEZNQCLSA-N 0.000 description 1
• ABMAVJAOLCPYCT-HNNXBMFYSA-N (1S)-2-cyclohexyl-1-[7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]ethanol Chemical compound C1(CCCCC1)C[C@H](O)C1=CC(=CC=2N1C=NC=2)C(F)(F)F ABMAVJAOLCPYCT-HNNXBMFYSA-N 0.000 description 1
• FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 1
• XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-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
• FLWWDYNPWOSLEO-HQVZTVAUSA-N (2s)-2-[[4-[1-(2-amino-4-oxo-1h-pteridin-6-yl)ethyl-methylamino]benzoyl]amino]pentanedioic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1C(C)N(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FLWWDYNPWOSLEO-HQVZTVAUSA-N 0.000 description 1
• AWLWPSSHYJQPCH-VIFPVBQESA-N (2s)-2-amino-3-(6-nitro-1h-indol-3-yl)propanoic acid Chemical compound [O-][N+](=O)C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 AWLWPSSHYJQPCH-VIFPVBQESA-N 0.000 description 1
• LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-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
• CSJCEQXZVMIHRX-QZTJIDSGSA-N (2s,3s)-2,3-dibenzyl-2,3-dihydroxybutanedioic acid Chemical compound C([C@@](O)(C(=O)O)[C@@](O)(CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 CSJCEQXZVMIHRX-QZTJIDSGSA-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
• TVIRNGFXQVMMGB-OFWIHYRESA-N (3s,6r,10r,13e,16s)-16-[(2r,3r,4s)-4-chloro-3-hydroxy-4-phenylbutan-2-yl]-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone Chemical compound C1=C(Cl)C(OC)=CC=C1C[C@@H]1C(=O)NC[C@@H](C)C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@H](C)[C@@H](O)[C@@H](Cl)C=2C=CC=CC=2)C/C=C/C(=O)N1 TVIRNGFXQVMMGB-OFWIHYRESA-N 0.000 description 1
• IVXYOWHFESRJBZ-UHFFFAOYSA-N (4-fluorophenyl)-imidazo[1,5-a]pyridin-5-ylmethanol Chemical compound FC1=CC=C(C=C1)C(O)C1=CC=CC=2N1C=NC=2 IVXYOWHFESRJBZ-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
• XFQSTSXYJYVPEX-UHFFFAOYSA-N (6-bromo-3-fluoropyridin-2-yl)methanamine Chemical compound BrC1=CC=C(C(=N1)CN)F XFQSTSXYJYVPEX-UHFFFAOYSA-N 0.000 description 1
• LFHDHPSQCBHHPJ-UHFFFAOYSA-N (6-bromoimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanone Chemical compound BrC=1C=CC=2N(C=1C(=O)C1CCCCC1)C=NC=2 LFHDHPSQCBHHPJ-UHFFFAOYSA-N 0.000 description 1
• QQHSFCFNMKTCET-UHFFFAOYSA-N (6-bromoimidazo[1,5-a]pyridin-5-yl)-cyclopentylmethanol Chemical compound BrC=1C=CC=2N(C=1C(O)C1CCCC1)C=NC=2 QQHSFCFNMKTCET-UHFFFAOYSA-N 0.000 description 1
• YPEGVUSTMDUQLL-UHFFFAOYSA-N (6-bromoimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound BrC=1C=CC=2N(C=1CO)C=NC=2 YPEGVUSTMDUQLL-UHFFFAOYSA-N 0.000 description 1
• YMITYADEUPAEKI-UHFFFAOYSA-N (6-chloro-7-fluoroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound ClC=1C(=CC=2N(C=1CO)C=NC=2)F YMITYADEUPAEKI-UHFFFAOYSA-N 0.000 description 1
• UDHJIFQJWANCAF-UHFFFAOYSA-N (6-chloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound ClC=1C=CC=2N(C=1CO)C=NC=2 UDHJIFQJWANCAF-UHFFFAOYSA-N 0.000 description 1
• SXWQIEVUEFYFJX-UHFFFAOYSA-N (7-bromo-6-chloroimidazo[1,5-a]pyridin-5-yl)-cyclopentylmethanol Chemical compound BrC1=CC=2N(C(=C1Cl)C(O)C1CCCC1)C=NC=2 SXWQIEVUEFYFJX-UHFFFAOYSA-N 0.000 description 1
• QQPPMQFYMPCLER-UHFFFAOYSA-N (7-bromo-6-chloroimidazo[1,5-a]pyridin-5-yl)-cyclopropylmethanol Chemical compound BrC1=CC=2N(C(=C1Cl)C(O)C1CC1)C=NC=2 QQPPMQFYMPCLER-UHFFFAOYSA-N 0.000 description 1
• MPRUPSUKEUKFDT-UHFFFAOYSA-N (7-bromo-6-chloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound BrC1=CC=2N(C(=C1Cl)CO)C=NC=2 MPRUPSUKEUKFDT-UHFFFAOYSA-N 0.000 description 1
• VCAGDYYRAYLVFS-UHFFFAOYSA-N (7-bromoimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound BrC1=CC=2N(C(=C1)C(O)C1CCCCC1)C=NC=2 VCAGDYYRAYLVFS-UHFFFAOYSA-N 0.000 description 1
• KWMGWTOIZUNUNC-UHFFFAOYSA-N (7-bromoimidazo[1,5-a]pyridin-5-yl)-cyclopentylmethanol Chemical compound BrC1=CC=2N(C(=C1)C(O)C1CCCC1)C=NC=2 KWMGWTOIZUNUNC-UHFFFAOYSA-N 0.000 description 1
• VEBMHUVDDLFGPM-UHFFFAOYSA-N (7-chloroimidazo[1,5-a]pyridin-5-yl)-[1-(hydroxymethyl)cyclohexyl]methanol Chemical compound ClC1=CC=2N(C(=C1)C(O)C1(CCCCC1)CO)C=NC=2 VEBMHUVDDLFGPM-UHFFFAOYSA-N 0.000 description 1
• CLMHUBJEVUCKCT-UHFFFAOYSA-N (7-chloroimidazo[1,5-a]pyridin-5-yl)-cyclopentylmethanol Chemical compound ClC1=CC=2N(C(=C1)C(O)C1CCCC1)C=NC=2 CLMHUBJEVUCKCT-UHFFFAOYSA-N 0.000 description 1
• KMRVGHJHHLQQDL-UHFFFAOYSA-N (7-chloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound ClC1=CC=2N(C(=C1)CO)C=NC=2 KMRVGHJHHLQQDL-UHFFFAOYSA-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
• AESVUZLWRXEGEX-DKCAWCKPSA-N (7S,9R)-7-[(2S,4R,5R,6R)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione iron(3+) Chemical compound [Fe+3].COc1cccc2C(=O)c3c(O)c4C[C@@](O)(C[C@H](O[C@@H]5C[C@@H](N)[C@@H](O)[C@@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO AESVUZLWRXEGEX-DKCAWCKPSA-N 0.000 description 1
• JXVAMODRWBNUSF-KZQKBALLSA-N (7s,9r,10r)-7-[(2r,4s,5s,6s)-5-[[(2s,4as,5as,7s,9s,9ar,10ar)-2,9-dimethyl-3-oxo-4,4a,5a,6,7,9,9a,10a-octahydrodipyrano[4,2-a:4',3'-e][1,4]dioxin-7-yl]oxy]-4-(dimethylamino)-6-methyloxan-2-yl]oxy-10-[(2s,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2 Chemical compound O([C@@H]1C2=C(O)C=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C2[C@@H](O[C@@H]2O[C@@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@H]4O[C@@H]5O[C@@H](C)C(=O)C[C@@H]5O[C@H]4C3)[C@H](C2)N(C)C)C[C@]1(O)CC)[C@H]1C[C@H](N(C)C)[C@H](O)[C@H](C)O1 JXVAMODRWBNUSF-KZQKBALLSA-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
• RCFNNLSZHVHCEK-IMHLAKCZSA-N (7s,9s)-7-(4-amino-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound [Cl-].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)C1CC([NH3+])CC(C)O1 RCFNNLSZHVHCEK-IMHLAKCZSA-N 0.000 description 1
• GFNACQAZOKYZGE-UHFFFAOYSA-N (8-bromoimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound BrC=1C=2N(C(=CC=1)C(O)C1CCCCC1)C=NC=2 GFNACQAZOKYZGE-UHFFFAOYSA-N 0.000 description 1
• LCMHLNHMHVZIQA-UHFFFAOYSA-N (8-fluoroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound FC=1C=2N(C(=CC=1)CO)C=NC=2 LCMHLNHMHVZIQA-UHFFFAOYSA-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
• 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 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
• VKPNOXPHJHZQQR-CQSZACIVSA-N (R)-(6-bromoimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound BrC=1C=CC=2N(C=1[C@H](O)C1CCCCC1)C=NC=2 VKPNOXPHJHZQQR-CQSZACIVSA-N 0.000 description 1
• MNUYLABZTVOVKM-SHEGYKQHSA-N (R)-2-bicyclo[2.2.1]heptanyl-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C12C(CC(CC1)C2)[C@@H](O)C1=C(C=CC=2N1C=NC=2)C1CC1 MNUYLABZTVOVKM-SHEGYKQHSA-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
• QVABKTKOARCFMU-CQSZACIVSA-N (R)-cyclohexyl-(6,7-dichloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)[C@@H](O)C1=C(C(=CC=2N1C=NC=2)Cl)Cl QVABKTKOARCFMU-CQSZACIVSA-N 0.000 description 1
• UBUZEVSPQOXVHM-CQSZACIVSA-N (R)-cyclohexyl-(6-iodoimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)[C@@H](O)C1=C(C=CC=2N1C=NC=2)I UBUZEVSPQOXVHM-CQSZACIVSA-N 0.000 description 1
• VKPNOXPHJHZQQR-AWEZNQCLSA-N (S)-(6-bromoimidazo[1,5-a]pyridin-5-yl)-cyclohexylmethanol Chemical compound BrC=1C=CC=2N(C=1[C@@H](O)C1CCCCC1)C=NC=2 VKPNOXPHJHZQQR-AWEZNQCLSA-N 0.000 description 1
• MNUYLABZTVOVKM-TVXJYTNOSA-N (S)-2-bicyclo[2.2.1]heptanyl-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C12C(CC(CC1)C2)[C@H](O)C1=C(C=CC=2N1C=NC=2)C1CC1 MNUYLABZTVOVKM-TVXJYTNOSA-N 0.000 description 1
• QVABKTKOARCFMU-AWEZNQCLSA-N (S)-cyclohexyl-(6,7-dichloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)[C@H](O)C1=C(C(=CC=2N1C=NC=2)Cl)Cl QVABKTKOARCFMU-AWEZNQCLSA-N 0.000 description 1
• UBUZEVSPQOXVHM-AWEZNQCLSA-N (S)-cyclohexyl-(6-iodoimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)[C@H](O)C1=C(C=CC=2N1C=NC=2)I UBUZEVSPQOXVHM-AWEZNQCLSA-N 0.000 description 1
• IZRXNSNERORBJM-AWEZNQCLSA-N (S)-cyclohexyl-[7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CCCCC1)[C@H](O)C1=CC(=CC=2N1C=NC=2)C(F)(F)F IZRXNSNERORBJM-AWEZNQCLSA-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
• 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
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
• 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
• WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 description 1
• DNZYTNFLPGMEHH-UHFFFAOYSA-N 1-(6-bromoimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound BrC=1C=CC=2N(C=1C(CC1CCCCC1)O)C=NC=2 DNZYTNFLPGMEHH-UHFFFAOYSA-N 0.000 description 1
• PXBRSQZDZJJUTP-UHFFFAOYSA-N 1-(6-chloro-7-fluoroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound ClC=1C(=CC=2N(C=1C(CC1CCCCC1)O)C=NC=2)F PXBRSQZDZJJUTP-UHFFFAOYSA-N 0.000 description 1
• DJRKEAJZPFKVTE-UHFFFAOYSA-N 1-(6-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound ClC=1C=CC=2N(C=1C(CC1CCCCC1)O)C=NC=2 DJRKEAJZPFKVTE-UHFFFAOYSA-N 0.000 description 1
• YDYMKODOJNNTHG-UHFFFAOYSA-N 1-(6-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylpropan-1-one Chemical compound ClC=1C=CC=2N(C=1C(C(C)C1CCCCC1)=O)C=NC=2 YDYMKODOJNNTHG-UHFFFAOYSA-N 0.000 description 1
• DFTLVULYPNPECI-UHFFFAOYSA-N 1-(6-chloroimidazo[1,5-a]pyridin-5-yl)-3-cyclohexylpropan-1-ol Chemical compound ClC=1C=CC=2N(C=1C(CCC1CCCCC1)O)C=NC=2 DFTLVULYPNPECI-UHFFFAOYSA-N 0.000 description 1
• WQVYNSCPHMKCFC-UHFFFAOYSA-N 1-(7-bromo-6-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound BrC1=CC=2N(C(=C1Cl)C(CC1CCCCC1)O)C=NC=2 WQVYNSCPHMKCFC-UHFFFAOYSA-N 0.000 description 1
• QZKIPNLVCMCZGA-UHFFFAOYSA-N 1-(7-bromo-8-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound BrC1=C(C=2N(C(=C1)C(CC1CCCCC1)O)C=NC=2)Cl QZKIPNLVCMCZGA-UHFFFAOYSA-N 0.000 description 1
• UKUFLIABWYMYJX-UHFFFAOYSA-N 1-(7-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound ClC1=CC=2N(C(=C1)C(CC1CCCCC1)O)C=NC=2 UKUFLIABWYMYJX-UHFFFAOYSA-N 0.000 description 1
• RECCYMGLRDXRGN-UHFFFAOYSA-N 1-(7-chloroimidazo[1,5-a]pyridin-5-yl)-3-cyclohexylpropan-1-ol Chemical compound ClC1=CC=2N(C(=C1)C(CCC1CCCCC1)O)C=NC=2 RECCYMGLRDXRGN-UHFFFAOYSA-N 0.000 description 1
• JSKSLBXNJGQGEP-UHFFFAOYSA-N 1-(8-chloroimidazo[1,5-a]pyridin-5-yl)-2-cyclohexylethanol Chemical compound ClC=1C=2N(C(=CC=1)C(CC1CCCCC1)O)C=NC=2 JSKSLBXNJGQGEP-UHFFFAOYSA-N 0.000 description 1
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
• KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 1
• JKTIOVWDWUVDNX-UHFFFAOYSA-N 1-cyclohexyl-1-imidazo[1,5-a]pyridin-5-ylethanol Chemical compound C1(CCCCC1)C(C)(O)C1=CC=CC=2N1C=NC=2 JKTIOVWDWUVDNX-UHFFFAOYSA-N 0.000 description 1
• UEAOJUXMVYYKEI-UHFFFAOYSA-N 1-imidazo[1,5-a]pyridin-5-yl-2,2-dimethylpropan-1-ol Chemical compound C=1N=CN2C=1C=CC=C2C(C(C)(C)C)O UEAOJUXMVYYKEI-UHFFFAOYSA-N 0.000 description 1
• VDNBUOHUSJLKBG-UHFFFAOYSA-N 1-imidazo[1,5-a]pyridin-5-yl-2-phenylethanol Chemical compound C=1N=CN2C=1C=CC=C2C(CC1=CC=CC=C1)O VDNBUOHUSJLKBG-UHFFFAOYSA-N 0.000 description 1
• QFHQBYHVWODQKP-UHFFFAOYSA-N 1-imidazo[1,5-a]pyridin-5-ylethanol Chemical compound C=1N=CN2C=1C=CC=C2C(C)O QFHQBYHVWODQKP-UHFFFAOYSA-N 0.000 description 1
• QSOZCYDBRRARTG-UHFFFAOYSA-N 1-imidazo[1,5-a]pyridin-5-ylprop-2-yn-1-ol Chemical compound C=1N=CN2C=1C=CC=C2C(C#C)O QSOZCYDBRRARTG-UHFFFAOYSA-N 0.000 description 1
• LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical group C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• BOMZMNZEXMAQQW-UHFFFAOYSA-N 2,5,11-trimethyl-6h-pyrido[4,3-b]carbazol-2-ium-9-ol;acetate Chemical compound CC([O-])=O.C[N+]1=CC=C2C(C)=C(NC=3C4=CC(O)=CC=3)C4=C(C)C2=C1 BOMZMNZEXMAQQW-UHFFFAOYSA-N 0.000 description 1
• ZPJPELHYQLLABP-UHFFFAOYSA-N 2-(1-adamantyl)-1-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)ethanol Chemical compound C12(CC3CC(CC(C1)C3)C2)CC(O)C1=C(C=CC=2N1C=NC=2)C1CC1 ZPJPELHYQLLABP-UHFFFAOYSA-N 0.000 description 1
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
• WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
• DGUXELQFYSAPFG-UHFFFAOYSA-N 2-[(6-bromo-3-fluoropyridin-2-yl)methyl]-3a,4-dihydroisoindole-1,3-dione Chemical compound BrC1=CC=C(C(=N1)CN1C(C2=CC=CCC2C1=O)=O)F DGUXELQFYSAPFG-UHFFFAOYSA-N 0.000 description 1
• YEPOVKUBWABWHU-UHFFFAOYSA-N 2-[(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]cyclohexan-1-ol Chemical compound C1(CC1)C=1C=CC=2N(C=1C(C1C(CCCC1)O)O)C=NC=2 YEPOVKUBWABWHU-UHFFFAOYSA-N 0.000 description 1
• XNAMZBCMLZQBIC-UHFFFAOYSA-N 2-[2-[4-[5-[(1-ethylpyrazol-3-yl)amino]triazolo[4,5-d]pyrimidin-1-yl]phenyl]propan-2-yloxy]ethanol Chemical compound CCN1C=CC(NC=2N=C3N=NN(C3=CN=2)C=2C=CC(=CC=2)C(C)(C)OCCO)=N1 XNAMZBCMLZQBIC-UHFFFAOYSA-N 0.000 description 1
• ALHXTYGCVYTWIY-UHFFFAOYSA-N 2-amino-3,7-dihydropurine-6-thione Chemical compound N1C(N)=NC(=S)C2=C1N=CN2.N1C(N)=NC(=S)C2=C1N=CN2 ALHXTYGCVYTWIY-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• 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
• DXJCNDCTIWOTLE-UHFFFAOYSA-N 2-cyclohexyl-1-(6,7-dichloroimidazo[1,5-a]pyridin-5-yl)ethanol Chemical compound C1(CCCCC1)CC(O)C1=C(C(=CC=2N1C=NC=2)Cl)Cl DXJCNDCTIWOTLE-UHFFFAOYSA-N 0.000 description 1
• XXQLKBPZCCGREZ-UHFFFAOYSA-N 2-cyclohexyl-1-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)ethanol Chemical compound C1(CCCCC1)CC(O)C1=C(C=CC=2N1C=NC=2)C1CC1 XXQLKBPZCCGREZ-UHFFFAOYSA-N 0.000 description 1
• PAXACHHUUASAST-UHFFFAOYSA-N 2-cyclohexyl-1-[6-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]ethanol Chemical compound C1(CCCCC1)CC(O)C1=C(C=CC=2N1C=NC=2)C(F)(F)F PAXACHHUUASAST-UHFFFAOYSA-N 0.000 description 1
• ABMAVJAOLCPYCT-UHFFFAOYSA-N 2-cyclohexyl-1-[7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]ethanol Chemical compound C1(CCCCC1)CC(O)C1=CC(=CC=2N1C=NC=2)C(F)(F)F ABMAVJAOLCPYCT-UHFFFAOYSA-N 0.000 description 1
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 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
• ZVUCBEXIOXKLHH-UHFFFAOYSA-N 3,4,5-trichloropyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=NC(C(O)=O)=C(Cl)C(Cl)=C1Cl ZVUCBEXIOXKLHH-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
• KWYLVDGOCQSPDM-UHFFFAOYSA-N 3,7-dihydropurine-6-thione Chemical compound SC1=NC=NC2=C1NC=N2.S=C1N=CNC2=C1NC=N2 KWYLVDGOCQSPDM-UHFFFAOYSA-N 0.000 description 1
• HLBOAQSKBNNHMW-UHFFFAOYSA-N 3-(3-methoxyphenyl)pyridine Chemical compound COC1=CC=CC(C=2C=NC=CC=2)=C1 HLBOAQSKBNNHMW-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
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
• DMWLBOPLZYJGPT-UHFFFAOYSA-N 3-(trifluoromethyl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=C1C(F)(F)F DMWLBOPLZYJGPT-UHFFFAOYSA-N 0.000 description 1
• VOSACOUHLDWXSM-UHFFFAOYSA-N 3-[(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]bicyclo[2.2.1]heptan-2-one Chemical compound C1(CC1)C=1C=CC=2N(C=1C(C1C(C3CCC1C3)=O)O)C=NC=2 VOSACOUHLDWXSM-UHFFFAOYSA-N 0.000 description 1
• YGMYEEHFBYSLJI-UHFFFAOYSA-N 3-[(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]cyclohexan-1-ol Chemical compound C1(CC1)C=1C=CC=2N(C=1C(C1CC(CCC1)O)O)C=NC=2 YGMYEEHFBYSLJI-UHFFFAOYSA-N 0.000 description 1
• TUJVGHCSNXCAFE-UHFFFAOYSA-N 3-bromo-2,6-dimethylpyridine Chemical compound CC1=CC=C(Br)C(C)=N1 TUJVGHCSNXCAFE-UHFFFAOYSA-N 0.000 description 1
• IKHJUSWVJKICAT-UHFFFAOYSA-N 3-bromopyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(Br)C(C(O)=O)=N1 IKHJUSWVJKICAT-UHFFFAOYSA-N 0.000 description 1
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
• FUMODQYXPKTVOU-UHFFFAOYSA-N 4,5,6,7-tetrahydrooxazepine Chemical compound C1CCC=NOC1 FUMODQYXPKTVOU-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
• HRSFQRARJWEZQA-UHFFFAOYSA-N 4-[(7-chloroimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]cyclohexan-1-one Chemical compound ClC1=CC=2N(C(=C1)C(C1CCC(CC1)=O)O)C=NC=2 HRSFQRARJWEZQA-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
• IYUMNONNHYADBU-UHFFFAOYSA-N 4-chloropyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CC(C(O)=O)=N1 IYUMNONNHYADBU-UHFFFAOYSA-N 0.000 description 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
• CIYYPWOUZPEAHS-UHFFFAOYSA-N 4-iodopyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC(I)=CC(C(O)=O)=N1 CIYYPWOUZPEAHS-UHFFFAOYSA-N 0.000 description 1
• VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
• HTMGQIXFZMZZKD-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinoline Chemical compound N1=CC=C2CCCCC2=C1 HTMGQIXFZMZZKD-UHFFFAOYSA-N 0.000 description 1
• VSLZVMINAUVQMM-UHFFFAOYSA-N 5-[(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)-hydroxymethyl]bicyclo[2.2.1]heptan-2-ol Chemical compound C1(CC1)C=1C=CC=2N(C=1C(C1C3CC(C(C1)C3)O)O)C=NC=2 VSLZVMINAUVQMM-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
• QXMLPUZUNQKXJV-UHFFFAOYSA-N 5-bromo-8-fluoroimidazo[1,5-a]pyridine Chemical compound BrC1=CC=C(C=2N1C=NC=2)F QXMLPUZUNQKXJV-UHFFFAOYSA-N 0.000 description 1
• JTKFIIQGMVKDNZ-UHFFFAOYSA-N 5-fluoropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(F)C=N1 JTKFIIQGMVKDNZ-UHFFFAOYSA-N 0.000 description 1
• UBMTZODMRPHSBC-UHFFFAOYSA-N 6,6-dimethyl-8-[7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CC1(C)CN(CCC11NC(=O)NC1=O)C1=CC(=CC2=CN=CN12)C(F)(F)F UBMTZODMRPHSBC-UHFFFAOYSA-N 0.000 description 1
• CHLHVJSRJYYPGI-UHFFFAOYSA-N 6-(trifluoromethyl)imidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound FC(C=1C=CC=2N(C=1C=O)C=NC=2)(F)F CHLHVJSRJYYPGI-UHFFFAOYSA-N 0.000 description 1
• WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-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
• AUBAFPZVFLTWNE-UHFFFAOYSA-N 6-bromo-2-(bromomethyl)-3-fluoropyridine Chemical compound FC1=CC=C(Br)N=C1CBr AUBAFPZVFLTWNE-UHFFFAOYSA-N 0.000 description 1
• BFQONZCQHGIKIY-UHFFFAOYSA-N 6-bromo-3-fluoro-2-methylpyridine Chemical compound CC1=NC(Br)=CC=C1F BFQONZCQHGIKIY-UHFFFAOYSA-N 0.000 description 1
• XHCKZJRQCAXBIZ-UHFFFAOYSA-N 6-chloro-7-fluoroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound ClC=1C(=CC=2N(C=1C=O)C=NC=2)F XHCKZJRQCAXBIZ-UHFFFAOYSA-N 0.000 description 1
• USDUIFDYXWFZBI-UHFFFAOYSA-N 6-methoxyimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound COC=1C=CC=2N(C=1C=O)C=NC=2 USDUIFDYXWFZBI-UHFFFAOYSA-N 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
• RIPXGTOMHRHBJA-UHFFFAOYSA-N 7-bromo-6-chloroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound BrC1=CC=2N(C(=C1Cl)C=O)C=NC=2 RIPXGTOMHRHBJA-UHFFFAOYSA-N 0.000 description 1
• GHLDYJTYKZIFBY-UHFFFAOYSA-N 7-chloro-5-[(4,4-difluorocyclohexyl)-fluoromethyl]imidazo[1,5-a]pyridine Chemical compound ClC1=CC=2N(C(=C1)C(F)C1CCC(CC1)(F)F)C=NC=2 GHLDYJTYKZIFBY-UHFFFAOYSA-N 0.000 description 1
• ODOBUNALJCOXIN-UHFFFAOYSA-N 7-chloro-5-[cyclohexyl(fluoro)methyl]imidazo[1,5-a]pyridine Chemical compound ClC1=CC=2N(C(=C1)C(F)C1CCCCC1)C=NC=2 ODOBUNALJCOXIN-UHFFFAOYSA-N 0.000 description 1
• YPWFNLSXQIGJCK-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1O2 YPWFNLSXQIGJCK-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• ITHXWBZYZNXQIX-UHFFFAOYSA-N 8-chloro-N-methoxy-N-methylimidazo[1,5-a]pyridine-5-carboxamide Chemical compound ClC=1C=2N(C(=CC=1)C(=O)N(C)OC)C=NC=2 ITHXWBZYZNXQIX-UHFFFAOYSA-N 0.000 description 1
• SQSGKVDFIKBQLL-UHFFFAOYSA-N 8-chloroimidazo[1,5-a]pyridine-5-carbonitrile Chemical compound ClC=1C=2N(C(=CC=1)C#N)C=NC=2 SQSGKVDFIKBQLL-UHFFFAOYSA-N 0.000 description 1
• CNRZTBJIOKNKDI-UHFFFAOYSA-N 8-chloroimidazo[1,5-a]pyridine-5-carboxylic acid Chemical compound ClC=1C=2N(C(=CC=1)C(=O)O)C=NC=2 CNRZTBJIOKNKDI-UHFFFAOYSA-N 0.000 description 1
• OHZPDKJFYCCVBA-UHFFFAOYSA-N 8-fluoroimidazo[1,5-a]pyridine-5-carbaldehyde Chemical compound FC=1C=2N(C(=CC=1)C=O)C=NC=2 OHZPDKJFYCCVBA-UHFFFAOYSA-N 0.000 description 1
• PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
• PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 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
• 108090000644 Angiozyme Proteins 0.000 description 1
• 102100029361 Aromatase Human genes 0.000 description 1
• 108010078554 Aromatase Proteins 0.000 description 1
• AXRYRYVKAWYZBR-UHFFFAOYSA-N Atazanavir Natural products C=1C=C(C=2N=CC=CC=2)C=CC=1CN(NC(=O)C(NC(=O)OC)C(C)(C)C)CC(O)C(NC(=O)C(NC(=O)OC)C(C)(C)C)CC1=CC=CC=C1 AXRYRYVKAWYZBR-UHFFFAOYSA-N 0.000 description 1
• 108010019625 Atazanavir Sulfate Proteins 0.000 description 1
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 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
• 206010004593 Bile duct cancer Diseases 0.000 description 1
• 229940122361 Bisphosphonate Drugs 0.000 description 1
• 206010005003 Bladder cancer Diseases 0.000 description 1
• 108010006654 Bleomycin Proteins 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
• NEBSFJAJVJCJPN-UHFFFAOYSA-N C(CCCCC)C(C)(O)C1=C(C(=CC=2N1C=NC2)Cl)Cl Chemical compound C(CCCCC)C(C)(O)C1=C(C(=CC=2N1C=NC2)Cl)Cl NEBSFJAJVJCJPN-UHFFFAOYSA-N 0.000 description 1
• FFLYFQJOZPJJNF-UHFFFAOYSA-N C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C#C[Si](C)(C)C Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C#C[Si](C)(C)C FFLYFQJOZPJJNF-UHFFFAOYSA-N 0.000 description 1
• GCTDVURLGBYOKW-UHFFFAOYSA-N CC(C)(C)OC(=O)NCc1ccc(Cl)c(n1)C(O)=O Chemical compound CC(C)(C)OC(=O)NCc1ccc(Cl)c(n1)C(O)=O GCTDVURLGBYOKW-UHFFFAOYSA-N 0.000 description 1
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
• 229940045513 CTLA4 antagonist Drugs 0.000 description 1
• JKEUJIRGLNNJEF-UHFFFAOYSA-N C[Si](C)(C)C#CC=1C=CC=2N(C=1C=O)C=NC=2 Chemical compound C[Si](C)(C)C#CC=1C=CC=2N(C=1C=O)C=NC=2 JKEUJIRGLNNJEF-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
• 201000009030 Carcinoma 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
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
• JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 1
• MKQWTWSXVILIKJ-LXGUWJNJSA-N Chlorozotocin Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NC(=O)N(N=O)CCCl MKQWTWSXVILIKJ-LXGUWJNJSA-N 0.000 description 1
• 101150065749 Churc1 gene Proteins 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• RWYJXXJFNOVJPG-UHFFFAOYSA-N ClC=1C(=NC(=CC1Cl)C(=O)O)C(=O)O Chemical compound ClC=1C(=NC(=CC1Cl)C(=O)O)C(=O)O RWYJXXJFNOVJPG-UHFFFAOYSA-N 0.000 description 1
• FRNGEIOFXXIUKG-UHFFFAOYSA-N ClC=1C(=NC(=CC1OC)C(=O)O)C(=O)O Chemical compound ClC=1C(=NC(=CC1OC)C(=O)O)C(=O)O FRNGEIOFXXIUKG-UHFFFAOYSA-N 0.000 description 1
• 208000016998 Conn syndrome Diseases 0.000 description 1
• 229930188224 Cryptophycin Natural products 0.000 description 1
• 101710095468 Cyclase Proteins 0.000 description 1
• 229920000858 Cyclodextrin Polymers 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
• 102100024329 Cytochrome P450 11B2, mitochondrial Human genes 0.000 description 1
• 101710170719 Cytochrome P450 11B2, mitochondrial Proteins 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• 108010092160 Dactinomycin Proteins 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
• NNJPGOLRFBJNIW-UHFFFAOYSA-N Demecolcine Natural products C1=C(OC)C(=O)C=C2C(NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-UHFFFAOYSA-N 0.000 description 1
• 108010002156 Depsipeptides Proteins 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
• 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
• 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 1
• 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 1
• 229930193152 Dynemicin Natural products 0.000 description 1
• AFMYMMXSQGUCBK-UHFFFAOYSA-N Endynamicin A Natural products C1#CC=CC#CC2NC(C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C3)=C3C34OC32C(C)C(C(O)=O)=C(OC)C41 AFMYMMXSQGUCBK-UHFFFAOYSA-N 0.000 description 1
• SAMRUMKYXPVKPA-VFKOLLTISA-N Enocitabine Chemical compound O=C1N=C(NC(=O)CCCCCCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 SAMRUMKYXPVKPA-VFKOLLTISA-N 0.000 description 1
• 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
• XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 206010018338 Glioma Diseases 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
• 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
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010020772 Hypertension 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
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 101710120843 Indoleamine 2,3-dioxygenase 1 Proteins 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 102000006992 Interferon-alpha Human genes 0.000 description 1
• 108010047761 Interferon-alpha Proteins 0.000 description 1
• 108010074328 Interferon-gamma Proteins 0.000 description 1
• 102000008070 Interferon-gamma Human genes 0.000 description 1
• 108010050904 Interferons Proteins 0.000 description 1
• 102000014150 Interferons Human genes 0.000 description 1
• 108010002350 Interleukin-2 Proteins 0.000 description 1
• 108010002386 Interleukin-3 Proteins 0.000 description 1
• 102100039064 Interleukin-3 Human genes 0.000 description 1
• 108010063738 Interleukins Proteins 0.000 description 1
• 102000015696 Interleukins Human genes 0.000 description 1
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
• 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
• JLERVPBPJHKRBJ-UHFFFAOYSA-N LY 117018 Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(O)C=C2S1 JLERVPBPJHKRBJ-UHFFFAOYSA-N 0.000 description 1
• 229920001491 Lentinan Polymers 0.000 description 1
• 108010000817 Leuprolide Proteins 0.000 description 1
• 229940124647 MEK inhibitor Drugs 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 229930126263 Maytansine Natural products 0.000 description 1
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
• IVDYZAAPOLNZKG-KWHRADDSSA-N Mepitiostane Chemical compound O([C@@H]1[C@]2(CC[C@@H]3[C@@]4(C)C[C@H]5S[C@H]5C[C@@H]4CC[C@H]3[C@@H]2CC1)C)C1(OC)CCCC1 IVDYZAAPOLNZKG-KWHRADDSSA-N 0.000 description 1
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• VFKZTMPDYBFSTM-KVTDHHQDSA-N Mitobronitol Chemical compound BrC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-KVTDHHQDSA-N 0.000 description 1
• HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Natural products O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• SUFFVZIXDJAYAX-UHFFFAOYSA-N N-[(6-bromo-3-fluoropyridin-2-yl)methyl]formamide Chemical compound C(=O)NCC1=NC(=CC=C1F)Br SUFFVZIXDJAYAX-UHFFFAOYSA-N 0.000 description 1
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 1
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
• SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 1
• KGTDRFCXGRULNK-UHFFFAOYSA-N Nogalamycin Natural products COC1C(OC)(C)C(OC)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=C4C5(C)OC(C(C(C5O)N(C)C)O)OC4=C3C3=O)=C3C=C2C(C(=O)OC)C(C)(O)C1 KGTDRFCXGRULNK-UHFFFAOYSA-N 0.000 description 1
• 229930187135 Olivomycin Natural products 0.000 description 1
• 108700020796 Oncogene Proteins 0.000 description 1
• 208000001388 Opportunistic Infections Diseases 0.000 description 1
• 229910019213 POCl3 Inorganic materials 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
• 208000037581 Persistent Infection Diseases 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
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
• 102100038239 Protein Churchill Human genes 0.000 description 1
• 102100024924 Protein kinase C alpha type Human genes 0.000 description 1
• 101710109947 Protein kinase C alpha type Proteins 0.000 description 1
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
• 108090000783 Renin Proteins 0.000 description 1
• 102100028255 Renin Human genes 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
• 206010039808 Secondary aldosteronism Diseases 0.000 description 1
• 229920000519 Sizofiran Polymers 0.000 description 1
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 230000024932 T cell mediated immunity Effects 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
• 229940126624 Tacatuzumab tetraxetan Drugs 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
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
• 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
• IWEQQRMGNVVKQW-OQKDUQJOSA-N Toremifene citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 IWEQQRMGNVVKQW-OQKDUQJOSA-N 0.000 description 1
• UMILHIMHKXVDGH-UHFFFAOYSA-N Triethylene glycol diglycidyl ether Chemical compound C1OC1COCCOCCOCCOCC1CO1 UMILHIMHKXVDGH-UHFFFAOYSA-N 0.000 description 1
• 239000007983 Tris buffer Substances 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
• 208000007097 Urinary Bladder 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
• 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
• 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
• IFJUINDAXYAPTO-UUBSBJJBSA-N [(8r,9s,13s,14s,17s)-17-[2-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyloxy]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4OC(=O)COC(=O)CCCC=1C=CC(=CC=1)N(CCCl)CCCl)C)CC2=CC=3OC(=O)C1=CC=CC=C1 IFJUINDAXYAPTO-UUBSBJJBSA-N 0.000 description 1
• IHGLINDYFMDHJG-UHFFFAOYSA-N [2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 IHGLINDYFMDHJG-UHFFFAOYSA-N 0.000 description 1
• YINLBFRXHPGKRH-UHFFFAOYSA-N [6-(aminomethyl)-3-cyclopropylpyridin-2-yl]-(2-bicyclo[2.2.1]heptanyl)methanol hydrochloride Chemical compound Cl.NCc1ccc(C2CC2)c(n1)C(O)C1CC2CCC1C2 YINLBFRXHPGKRH-UHFFFAOYSA-N 0.000 description 1
• XVGGUXTUYHSRDE-UHFFFAOYSA-N [6-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound FC(C=1C=CC=2N(C=1CO)C=NC=2)(F)F XVGGUXTUYHSRDE-UHFFFAOYSA-N 0.000 description 1
• QZYAQEJILIKKOM-UHFFFAOYSA-N [6-chloro-7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]-cyclohexylmethanol Chemical compound ClC=1C(=CC=2N(C=1C(O)C1CCCCC1)C=NC=2)C(F)(F)F QZYAQEJILIKKOM-UHFFFAOYSA-N 0.000 description 1
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
• OJZYKXVZJOFMSZ-UHFFFAOYSA-M [Cl-].[Mg+]CC1CCCCC1 Chemical compound [Cl-].[Mg+]CC1CCCCC1 OJZYKXVZJOFMSZ-UHFFFAOYSA-M 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
• 230000002159 abnormal effect Effects 0.000 description 1
• 229940028652 abraxane Drugs 0.000 description 1
• 238000010521 absorption reaction Methods 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
• 229960000583 acetic acid Drugs 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 229930183665 actinomycin Natural products 0.000 description 1
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Chemical compound 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 1
• 230000033289 adaptive immune response Effects 0.000 description 1
• 229950004955 adozelesin Drugs 0.000 description 1
• BYRVKDUQDLJUBX-JJCDCTGGSA-N adozelesin Chemical compound C1=CC=C2OC(C(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C[C@H]4C[C@]44C5=C(C(C=C43)=O)NC=C5C)=CC2=C1 BYRVKDUQDLJUBX-JJCDCTGGSA-N 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 108700025316 aldesleukin Proteins 0.000 description 1
• 229960002478 aldosterone Drugs 0.000 description 1
• 230000003113 alkalizing effect Effects 0.000 description 1
• 229930013930 alkaloid Natural products 0.000 description 1
• 125000002009 alkene group Chemical group 0.000 description 1
• 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
• 150000008052 alkyl sulfonates Chemical class 0.000 description 1
• 230000000735 allogeneic effect Effects 0.000 description 1
• 125000006242 amine protecting group Chemical group 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 229940024606 amino acid Drugs 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229960001220 amsacrine Drugs 0.000 description 1
• XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
• 238000012435 analytical chromatography Methods 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
• 239000004037 angiogenesis inhibitor Substances 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 239000003817 anthracycline antibiotic agent Substances 0.000 description 1
• 230000002280 anti-androgenic effect Effects 0.000 description 1
• 229940124650 anti-cancer therapies Drugs 0.000 description 1
• 229940046836 anti-estrogen Drugs 0.000 description 1
• 230000001833 anti-estrogenic effect Effects 0.000 description 1
• 230000003388 anti-hormonal effect Effects 0.000 description 1
• 230000000692 anti-sense effect Effects 0.000 description 1
• 239000000051 antiandrogen Substances 0.000 description 1
• 239000000611 antibody drug conjugate Substances 0.000 description 1
• 229940049595 antibody-drug conjugate Drugs 0.000 description 1
• 238000011319 anticancer therapy Methods 0.000 description 1
• 229940045686 antimetabolites antineoplastic purine analogs Drugs 0.000 description 1
• 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• 230000005975 antitumor immune response Effects 0.000 description 1
• 229950003145 apolizumab Drugs 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• 150000008209 arabinosides Chemical class 0.000 description 1
• 229910052786 argon Inorganic materials 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
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 229950002882 aselizumab Drugs 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 description 1
• 229960003277 atazanavir Drugs 0.000 description 1
• 230000005784 autoimmunity Effects 0.000 description 1
• 229960002756 azacitidine Drugs 0.000 description 1
• 229950011321 azaserine Drugs 0.000 description 1
• 125000003725 azepanyl group Chemical group 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 150000001541 aziridines Chemical class 0.000 description 1
• 125000004069 aziridinyl group Chemical group 0.000 description 1
• 229950001863 bapineuzumab Drugs 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 229960000686 benzalkonium chloride Drugs 0.000 description 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
• 150000001555 benzenes Chemical class 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
• CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
• 229960000997 bicalutamide Drugs 0.000 description 1
• ACWZRVQXLIRSDF-UHFFFAOYSA-N binimetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1F ACWZRVQXLIRSDF-UHFFFAOYSA-N 0.000 description 1
• 238000004166 bioassay Methods 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 230000008033 biological extinction Effects 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 230000005540 biological transmission Effects 0.000 description 1
• 229950008548 bisantrene Drugs 0.000 description 1
• 150000004663 bisphosphonates Chemical class 0.000 description 1
• 229960005522 bivatuzumab mertansine Drugs 0.000 description 1
• 229950006844 bizelesin Drugs 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
• 210000004204 blood vessel Anatomy 0.000 description 1
• 229910000085 borane Inorganic materials 0.000 description 1
• MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
• 229960001467 bortezomib Drugs 0.000 description 1
• IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
• LOXORFRCPXUORP-UHFFFAOYSA-N bromo-Cycloheptane Chemical compound BrC1CCCCCC1 LOXORFRCPXUORP-UHFFFAOYSA-N 0.000 description 1
• AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
• HELISQMWNRMVDD-UHFFFAOYSA-N bromocyclohexane;magnesium Chemical compound [Mg].BrC1CCCCC1 HELISQMWNRMVDD-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
• 239000012928 buffer substance Substances 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
• OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229950009908 cactinomycin Drugs 0.000 description 1
• 229930195731 calicheamicin Natural products 0.000 description 1
• IVFYLRMMHVYGJH-PVPPCFLZSA-N calusterone Chemical compound C1C[C@]2(C)[C@](O)(C)CC[C@H]2[C@@H]2[C@@H](C)CC3=CC(=O)CC[C@]3(C)[C@H]21 IVFYLRMMHVYGJH-PVPPCFLZSA-N 0.000 description 1
• 229950009823 calusterone Drugs 0.000 description 1
• 229940112129 campath Drugs 0.000 description 1
• 229940088954 camptosar Drugs 0.000 description 1
• 229950007296 cantuzumab mertansine Drugs 0.000 description 1
• 229960004117 capecitabine Drugs 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
• 239000001768 carboxy methyl cellulose Substances 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
• 229960005243 carmustine Drugs 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
• 108010047060 carzinophilin Proteins 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 229950006754 cedelizumab Drugs 0.000 description 1
• 230000030833 cell death Effects 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 229960003115 certolizumab pegol Drugs 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 229960004630 chlorambucil Drugs 0.000 description 1
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
• 150000001805 chlorine compounds Chemical group 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 229960001480 chlorozotocin Drugs 0.000 description 1
• 208000037976 chronic inflammation Diseases 0.000 description 1
• 230000006020 chronic inflammation Effects 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• 229960004316 cisplatin Drugs 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
• 238000011260 co-administration Methods 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 229960002271 cobimetinib Drugs 0.000 description 1
• BSMCAPRUBJMWDF-KRWDZBQOSA-N cobimetinib Chemical compound C1C(O)([C@H]2NCCCC2)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F BSMCAPRUBJMWDF-KRWDZBQOSA-N 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000012230 colorless oil Substances 0.000 description 1
• 229940000425 combination drug Drugs 0.000 description 1
• 229940125773 compound 10 Drugs 0.000 description 1
• 229940125898 compound 5 Drugs 0.000 description 1
• 229940125890 compound Ia Drugs 0.000 description 1
• 238000011254 conventional chemotherapy Methods 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 210000004087 cornea Anatomy 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 108010089438 cryptophycin 1 Proteins 0.000 description 1
• PSNOPSMXOBPNNV-VVCTWANISA-N cryptophycin 1 Chemical compound C1=C(Cl)C(OC)=CC=C1C[C@@H]1C(=O)NC[C@@H](C)C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@H](C)[C@@H]2[C@H](O2)C=2C=CC=CC=2)C/C=C/C(=O)N1 PSNOPSMXOBPNNV-VVCTWANISA-N 0.000 description 1
• 108010090203 cryptophycin 8 Proteins 0.000 description 1
• PSNOPSMXOBPNNV-UHFFFAOYSA-N cryptophycin-327 Natural products C1=C(Cl)C(OC)=CC=C1CC1C(=O)NCC(C)C(=O)OC(CC(C)C)C(=O)OC(C(C)C2C(O2)C=2C=CC=CC=2)CC=CC(=O)N1 PSNOPSMXOBPNNV-UHFFFAOYSA-N 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• GANIPOXJWFKFKE-UHFFFAOYSA-N cyclobutyl(imidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCC1)C(O)C1=CC=CC=2N1C=NC=2 GANIPOXJWFKFKE-UHFFFAOYSA-N 0.000 description 1
• 229940097362 cyclodextrins Drugs 0.000 description 1
• GZNUVFQHEZQTOJ-UHFFFAOYSA-N cycloheptyl(imidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCCC1)C(O)C1=CC=CC=2N1C=NC=2 GZNUVFQHEZQTOJ-UHFFFAOYSA-N 0.000 description 1
• PTEKRBUIHVDJDE-UHFFFAOYSA-N cycloheptyl-[7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CCCCCC1)C(O)C1=CC(=CC=2N1C=NC=2)C(F)(F)F PTEKRBUIHVDJDE-UHFFFAOYSA-N 0.000 description 1
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
• UBUZEVSPQOXVHM-UHFFFAOYSA-N cyclohexyl-(6-iodoimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)I UBUZEVSPQOXVHM-UHFFFAOYSA-N 0.000 description 1
• LVHCVOBBACPOTO-UHFFFAOYSA-N cyclohexyl-(6-methylimidazo[1,5-a]pyridin-5-yl)methanone Chemical compound C1(CCCCC1)C(=O)C1=C(C=CC=2N1C=NC=2)C LVHCVOBBACPOTO-UHFFFAOYSA-N 0.000 description 1
• ZMSQVLKPRVEREW-UHFFFAOYSA-N cyclohexyl-(6-phenylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C1=CC=CC=C1 ZMSQVLKPRVEREW-UHFFFAOYSA-N 0.000 description 1
• TZOMMEYXUZEXCF-UHFFFAOYSA-N cyclohexyl-(6-prop-1-en-2-ylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C(=C)C TZOMMEYXUZEXCF-UHFFFAOYSA-N 0.000 description 1
• OINWFSLVXWVRCB-UHFFFAOYSA-N cyclohexyl-(6-propan-2-ylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C(C)C OINWFSLVXWVRCB-UHFFFAOYSA-N 0.000 description 1
• LKJPXULERNECRH-UHFFFAOYSA-N cyclohexyl-(7,8-dichloroimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCCC1)C(O)C1=CC(=C(C=2N1C=NC=2)Cl)Cl LKJPXULERNECRH-UHFFFAOYSA-N 0.000 description 1
• OVTRWVWDAZUCHL-UHFFFAOYSA-N cyclohexyl-(7-iodoimidazo[1,5-a]pyridin-5-yl)methanol 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(C1CCCCC1)c1cc(I)cc2cncn12 OVTRWVWDAZUCHL-UHFFFAOYSA-N 0.000 description 1
• QTCKRLAHFLTKRZ-UHFFFAOYSA-N cyclohexyl-[6-(3,5-dimethyl-1,2-oxazol-4-yl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C=1C(=NOC=1C)C QTCKRLAHFLTKRZ-UHFFFAOYSA-N 0.000 description 1
• GYUZGPKWLGKREF-UHFFFAOYSA-N cyclohexyl-[6-(cyclopenten-1-yl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CCCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C1=CCCC1 GYUZGPKWLGKREF-UHFFFAOYSA-N 0.000 description 1
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([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
• XUNKHNWDKFQQGW-UHFFFAOYSA-N cyclopenta-1,4-dien-1-yloxy(trimethyl)silane Chemical compound C[Si](C)(C)OC1=CCC=C1 XUNKHNWDKFQQGW-UHFFFAOYSA-N 0.000 description 1
• JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 1
• CEHHOLNSHWUWFB-UHFFFAOYSA-N cyclopentyl(imidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCC1)C(O)C1=CC=CC=2N1C=NC=2 CEHHOLNSHWUWFB-UHFFFAOYSA-N 0.000 description 1
• GTSIAADADQVKKG-UHFFFAOYSA-N cyclopentyl-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C1CC1 GTSIAADADQVKKG-UHFFFAOYSA-N 0.000 description 1
• FOSFOTQAMGSGNQ-UHFFFAOYSA-N cyclopentyl-[6-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CCCC1)C(O)C1=C(C=CC=2N1C=NC=2)C(F)(F)F FOSFOTQAMGSGNQ-UHFFFAOYSA-N 0.000 description 1
• OUFVEPJJMFWNAQ-UHFFFAOYSA-N cyclopentyl-[7-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CCCC1)C(O)C1=CC(=CC=2N1C=NC=2)C(F)(F)F OUFVEPJJMFWNAQ-UHFFFAOYSA-N 0.000 description 1
• LBLBYSGVLROOAF-UHFFFAOYSA-N cyclopropyl(imidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CC1)C(O)C1=CC=CC=2N1C=NC=2 LBLBYSGVLROOAF-UHFFFAOYSA-N 0.000 description 1
• ZCAPZNCLBDIBDN-UHFFFAOYSA-N cyclopropyl-(6-cyclopropylimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CC1)C(O)C1=C(C=CC=2N1C=NC=2)C1CC1 ZCAPZNCLBDIBDN-UHFFFAOYSA-N 0.000 description 1
• XALSLYAVTOMVPM-UHFFFAOYSA-N cyclopropyl-(6-iodoimidazo[1,5-a]pyridin-5-yl)methanol Chemical compound C1(CC1)C(O)C1=C(C=CC=2N1C=NC=2)I XALSLYAVTOMVPM-UHFFFAOYSA-N 0.000 description 1
• MDWGQIFRXYOUIB-UHFFFAOYSA-N cyclopropyl-[6-(trifluoromethyl)imidazo[1,5-a]pyridin-5-yl]methanol Chemical compound C1(CC1)C(O)C1=C(C=CC=2N1C=NC=2)C(F)(F)F MDWGQIFRXYOUIB-UHFFFAOYSA-N 0.000 description 1
• 229940104302 cytosine Drugs 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• 229960002806 daclizumab Drugs 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 229960005107 darunavir Drugs 0.000 description 1
• CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 description 1
• 229960005052 demecolcine Drugs 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
• WVYXNIXAMZOZFK-UHFFFAOYSA-N diaziquone Chemical compound O=C1C(NC(=O)OCC)=C(N2CC2)C(=O)C(NC(=O)OCC)=C1N1CC1 WVYXNIXAMZOZFK-UHFFFAOYSA-N 0.000 description 1
• 229950002389 diaziquone Drugs 0.000 description 1
• WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
• KNVYGLXGRDZGQX-UHFFFAOYSA-N diethyl 3,4,5-trichloropyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=C(Cl)C(Cl)=C1Cl KNVYGLXGRDZGQX-UHFFFAOYSA-N 0.000 description 1
• QZLXQMMCUFDAEL-UHFFFAOYSA-N diethyl 3,4-dichloropyridine-2,6-dicarboxylate Chemical compound ClC=1C(=NC(=CC=1Cl)C(=O)OCC)C(=O)OCC QZLXQMMCUFDAEL-UHFFFAOYSA-N 0.000 description 1
• YDJPOPXOEABYGO-UHFFFAOYSA-N diethyl 3-bromopyridine-2,6-dicarboxylate Chemical compound BrC=1C(=NC(=CC=1)C(=O)OCC)C(=O)OCC YDJPOPXOEABYGO-UHFFFAOYSA-N 0.000 description 1
• YFLQRCUJTJTIMO-UHFFFAOYSA-N diethyl 3-chloro-4-methoxypyridine-2,6-dicarboxylate Chemical compound ClC=1C(=NC(=CC=1OC)C(=O)OCC)C(=O)OCC YFLQRCUJTJTIMO-UHFFFAOYSA-N 0.000 description 1
• QLTGCKFJAYYKLX-UHFFFAOYSA-N diethyl 3-chloro-4-oxo-1H-pyridine-2,6-dicarboxylate Chemical compound ClC=1C(=NC(=CC=1O)C(=O)OCC)C(=O)OCC QLTGCKFJAYYKLX-UHFFFAOYSA-N 0.000 description 1
• YFMCNLZLAKGYDA-UHFFFAOYSA-N diethyl 4-(trifluoromethyl)pyridine-2,6-dicarboxylate Chemical compound FC(C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC)(F)F YFMCNLZLAKGYDA-UHFFFAOYSA-N 0.000 description 1
• OQMSUUFFXOJVGT-UHFFFAOYSA-N diethyl 4-bromo-3-chloropyridine-2,6-dicarboxylate Chemical compound BrC1=C(C(=NC(=C1)C(=O)OCC)C(=O)OCC)Cl OQMSUUFFXOJVGT-UHFFFAOYSA-N 0.000 description 1
• XQVRVZXJZVVBLW-UHFFFAOYSA-N diethyl 4-chloropyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=CC(Cl)=CC(C(=O)OCC)=N1 XQVRVZXJZVVBLW-UHFFFAOYSA-N 0.000 description 1
• OPCIHVVDMSLUOK-UHFFFAOYSA-N diethyl 4-iodopyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=CC(I)=CC(C(=O)OCC)=N1 OPCIHVVDMSLUOK-UHFFFAOYSA-N 0.000 description 1
• KTOBUCHVPBPHMK-UHFFFAOYSA-N diethyl pyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=N1 KTOBUCHVPBPHMK-UHFFFAOYSA-N 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
• 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
• MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
• 150000002009 diols Chemical class 0.000 description 1
• 150000002013 dioxins Chemical class 0.000 description 1
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
• 238000006073 displacement reaction Methods 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 125000005883 dithianyl group Chemical group 0.000 description 1
• 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
• 239000003534 dna topoisomerase inhibitor Substances 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
• 239000008298 dragée Substances 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
• 239000006196 drop Substances 0.000 description 1
• 229950004683 drostanolone propionate Drugs 0.000 description 1
• 230000009977 dual effect Effects 0.000 description 1
• 229960005501 duocarmycin Drugs 0.000 description 1
• 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 1
• 229930184221 duocarmycin Natural products 0.000 description 1
• 229950009791 durvalumab Drugs 0.000 description 1
• AFMYMMXSQGUCBK-AKMKHHNQSA-N dynemicin a Chemical compound C1#C\C=C/C#C[C@@H]2NC(C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C3)=C3[C@@]34O[C@]32[C@@H](C)C(C(O)=O)=C(OC)[C@H]41 AFMYMMXSQGUCBK-AKMKHHNQSA-N 0.000 description 1
• 239000008157 edible vegetable oil Substances 0.000 description 1
• 210000003162 effector t lymphocyte Anatomy 0.000 description 1
• 229960002759 eflornithine Drugs 0.000 description 1
• 229920001971 elastomer Polymers 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
• 229950000549 elliptinium acetate Drugs 0.000 description 1
• 229960004137 elotuzumab Drugs 0.000 description 1
• 229940120655 eloxatin Drugs 0.000 description 1
• 210000002257 embryonic structure Anatomy 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• JOZGNYDSEBIJDH-UHFFFAOYSA-N eniluracil Chemical compound O=C1NC=C(C#C)C(=O)N1 JOZGNYDSEBIJDH-UHFFFAOYSA-N 0.000 description 1
• 229950010213 eniluracil Drugs 0.000 description 1
• 229950011487 enocitabine Drugs 0.000 description 1
• 229950002973 epitiostanol Drugs 0.000 description 1
• 229940082789 erbitux Drugs 0.000 description 1
• 229960001433 erlotinib 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
• 229960001842 estramustine Drugs 0.000 description 1
• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• 239000000328 estrogen antagonist Substances 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
• FNUNIWIBVLIJNN-UHFFFAOYSA-N ethyl 1-oxido-3-(trifluoromethyl)pyridin-1-ium-2-carboxylate Chemical compound C(C)OC(=O)C1=[N+](C=CC=C1C(F)(F)F)[O-] FNUNIWIBVLIJNN-UHFFFAOYSA-N 0.000 description 1
• JODGHBVIIRXXFM-UHFFFAOYSA-N ethyl 3,4-dichloro-6-(chloromethyl)pyridine-2-carboxylate Chemical compound ClC=1C(=NC(=CC=1Cl)CCl)C(=O)OCC JODGHBVIIRXXFM-UHFFFAOYSA-N 0.000 description 1
• YWFCLGHVIXWPPZ-UHFFFAOYSA-N ethyl 3,6-dichloropyridine-2-carboxylate Chemical compound CCOC(=O)C1=NC(Cl)=CC=C1Cl YWFCLGHVIXWPPZ-UHFFFAOYSA-N 0.000 description 1
• CNITUJQBBIMJBR-UHFFFAOYSA-N ethyl 3-(trifluoromethyl)pyridine-2-carboxylate Chemical compound CCOC(=O)C1=NC=CC=C1C(F)(F)F CNITUJQBBIMJBR-UHFFFAOYSA-N 0.000 description 1
• UNANXYFMPBJRNQ-UHFFFAOYSA-N ethyl 3-bromo-6-(chloromethyl)pyridine-2-carboxylate Chemical compound BrC=1C(=NC(=CC=1)CCl)C(=O)OCC UNANXYFMPBJRNQ-UHFFFAOYSA-N 0.000 description 1
• XWZSKERCKMSMNO-UHFFFAOYSA-N ethyl 3-bromo-6-(hydroxymethyl)pyridine-2-carboxylate Chemical compound BrC=1C(=NC(=CC=1)CO)C(=O)OCC XWZSKERCKMSMNO-UHFFFAOYSA-N 0.000 description 1
• GGCOCQFUAVKWIA-UHFFFAOYSA-N ethyl 3-chloro-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridine-2-carboxylate Chemical compound CCOC(=O)C1=NC(CNC(=O)OC(C)(C)C)=CC=C1Cl GGCOCQFUAVKWIA-UHFFFAOYSA-N 0.000 description 1
• PKODMFVQYYTXNS-UHFFFAOYSA-N ethyl 4,5-dichloro-6-(chloromethyl)pyridine-2-carboxylate Chemical compound ClC1=CC(=NC(=C1Cl)CCl)C(=O)OCC PKODMFVQYYTXNS-UHFFFAOYSA-N 0.000 description 1
• WWRNKLRLHPEBBD-UHFFFAOYSA-N ethyl 4-bromo-3-chloro-6-[(4-methylphenyl)sulfonyloxymethyl]pyridine-2-carboxylate Chemical compound BrC1=C(C(=NC(=C1)COS(=O)(=O)C1=CC=C(C)C=C1)C(=O)OCC)Cl WWRNKLRLHPEBBD-UHFFFAOYSA-N 0.000 description 1
• CSPLFNAKKCSVKM-UHFFFAOYSA-N ethyl 5-bromo-6-(hydroxymethyl)pyridine-2-carboxylate Chemical compound BrC=1C=CC(=NC=1CO)C(=O)OCC CSPLFNAKKCSVKM-UHFFFAOYSA-N 0.000 description 1
• SXEVJTBXOINDIO-UHFFFAOYSA-N ethyl 5-chloro-6-(hydroxymethyl)-4-methoxypyridine-2-carboxylate Chemical compound ClC=1C(=CC(=NC=1CO)C(=O)OCC)OC SXEVJTBXOINDIO-UHFFFAOYSA-N 0.000 description 1
• OANVECSJKLDDMR-UHFFFAOYSA-N ethyl 6,7,8-trichloroimidazo[1,5-a]pyridine-5-carboxylate Chemical compound ClC=1C(=C(C=2N(C=1C(=O)OCC)C=NC=2)Cl)Cl OANVECSJKLDDMR-UHFFFAOYSA-N 0.000 description 1
• BSFOYUQVKSUTEY-UHFFFAOYSA-N ethyl 6-(aminomethyl)-3-(trifluoromethyl)pyridine-2-carboxylate Chemical compound NCC1=CC=C(C(=N1)C(=O)OCC)C(F)(F)F BSFOYUQVKSUTEY-UHFFFAOYSA-N 0.000 description 1
• BKXPDTCKPNXZHK-UHFFFAOYSA-N ethyl 6-(aminomethyl)-3-bromopyridine-2-carboxylate Chemical compound NCC1=CC=C(C(=N1)C(=O)OCC)Br BKXPDTCKPNXZHK-UHFFFAOYSA-N 0.000 description 1
• YLKZTUXIRZUOSF-UHFFFAOYSA-N ethyl 6-(aminomethyl)-3-chloropyridine-2-carboxylate Chemical compound NCC1=CC=C(C(=N1)C(=O)OCC)Cl YLKZTUXIRZUOSF-UHFFFAOYSA-N 0.000 description 1
• PZIUSTKLITYGCN-UHFFFAOYSA-N ethyl 6-(aminomethyl)-4,5-dichloropyridine-2-carboxylate Chemical compound NCC1=C(C(=CC(=N1)C(=O)OCC)Cl)Cl PZIUSTKLITYGCN-UHFFFAOYSA-N 0.000 description 1
• SAHOZFWRWQZFCH-UHFFFAOYSA-N ethyl 6-(aminomethyl)pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC(CN)=N1 SAHOZFWRWQZFCH-UHFFFAOYSA-N 0.000 description 1
• BIQUYZVRWQMJIO-UHFFFAOYSA-N ethyl 6-(trifluoromethyl)imidazo[1,5-a]pyridine-5-carboxylate Chemical compound FC(C=1C=CC=2N(C=1C(=O)OCC)C=NC=2)(F)F BIQUYZVRWQMJIO-UHFFFAOYSA-N 0.000 description 1
• BULZWVVERHLQFT-UHFFFAOYSA-N ethyl 6-bromoimidazo[1,5-a]pyridine-5-carboxylate Chemical compound BrC=1C=CC=2N(C=1C(=O)OCC)C=NC=2 BULZWVVERHLQFT-UHFFFAOYSA-N 0.000 description 1
• RFOLYKBIRFWGQK-UHFFFAOYSA-N ethyl 6-chloroimidazo[1,5-a]pyridine-5-carboxylate Chemical compound ClC=1C=CC=2N(C=1C(=O)OCC)C=NC=2 RFOLYKBIRFWGQK-UHFFFAOYSA-N 0.000 description 1
• ZNNCGIHXRXAFOS-UHFFFAOYSA-N ethyl 6-cyano-3-(trifluoromethyl)pyridine-2-carboxylate Chemical compound C(#N)C1=CC=C(C(=N1)C(=O)OCC)C(F)(F)F ZNNCGIHXRXAFOS-UHFFFAOYSA-N 0.000 description 1
• IBRCIOCIKUITOR-UHFFFAOYSA-N ethyl 7-bromo-6-chloroimidazo[1,5-a]pyridine-5-carboxylate Chemical compound BrC1=CC=2N(C(=C1Cl)C(=O)OCC)C=NC=2 IBRCIOCIKUITOR-UHFFFAOYSA-N 0.000 description 1
• SXCRXYRXIZZQBG-UHFFFAOYSA-N ethyl 7-bromo-8-chloroimidazo[1,5-a]pyridine-5-carboxylate Chemical compound BrC1=C(C=2N(C(=C1)C(=O)OCC)C=NC=2)Cl SXCRXYRXIZZQBG-UHFFFAOYSA-N 0.000 description 1
• WTUJJRJPOCETAE-UHFFFAOYSA-N ethyl 8-chloro-7-methoxyimidazo[1,5-a]pyridine-5-carboxylate Chemical compound ClC=1C=2N(C(=CC=1OC)C(=O)OCC)C=NC=2 WTUJJRJPOCETAE-UHFFFAOYSA-N 0.000 description 1
• AREBVRIHBMCAHY-UHFFFAOYSA-N ethyl 8-fluoroimidazo[1,5-a]pyridine-5-carboxylate Chemical compound FC=1C=2N(C(=CC=1)C(=O)OCC)C=NC=2 AREBVRIHBMCAHY-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 1
• 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
• WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
• NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
• 229960005237 etoglucid Drugs 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
• 230000005496 eutectics Effects 0.000 description 1
• 229960000255 exemestane Drugs 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• 229950011548 fadrozole Drugs 0.000 description 1
• 229940043168 fareston Drugs 0.000 description 1
• 229940087861 faslodex Drugs 0.000 description 1
• 229950001563 felvizumab Drugs 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 229960000961 floxuridine Drugs 0.000 description 1
• ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
• 125000001153 fluoro group Chemical group F* 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
• 229960002074 flutamide Drugs 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
• 229950004923 fontolizumab Drugs 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 229960004783 fotemustine Drugs 0.000 description 1
• YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 238000005194 fractionation Methods 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 229940044658 gallium nitrate Drugs 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 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
• 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
• 238000007429 general method Methods 0.000 description 1
• 229940080856 gleevec Drugs 0.000 description 1
• ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
• 150000004676 glycans Chemical class 0.000 description 1
• 150000002334 glycols Chemical class 0.000 description 1
• 229960002913 goserelin Drugs 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
• 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
• 229940022353 herceptin Drugs 0.000 description 1
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 208000029824 high grade glioma Diseases 0.000 description 1
• 210000005260 human cell Anatomy 0.000 description 1
• 230000036571 hydration Effects 0.000 description 1
• 238000006703 hydration reaction Methods 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• 229960001330 hydroxycarbamide Drugs 0.000 description 1
• 229940015872 ibandronate Drugs 0.000 description 1
• 229960003685 imatinib mesylate Drugs 0.000 description 1
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
• RMMORMAEHMEACD-UHFFFAOYSA-N imidazo[1,5-a]pyridin-5-yl(oxan-4-yl)methanol Chemical compound C=1N=CN2C=1C=CC=C2C(O)C1CCOCC1 RMMORMAEHMEACD-UHFFFAOYSA-N 0.000 description 1
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000005945 imidazopyridyl group Chemical group 0.000 description 1
• 230000002519 immonomodulatory effect Effects 0.000 description 1
• 230000028993 immune response Effects 0.000 description 1
• 230000037451 immune surveillance Effects 0.000 description 1
• 210000000987 immune system Anatomy 0.000 description 1
• 230000006058 immune tolerance Effects 0.000 description 1
• 230000002163 immunogen Effects 0.000 description 1
• 239000000367 immunologic factor Substances 0.000 description 1
• 238000009169 immunotherapy Methods 0.000 description 1
• 238000005462 in vivo assay Methods 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 230000001965 increasing effect Effects 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 230000015788 innate immune response Effects 0.000 description 1
• 229950004101 inotuzumab ozogamicin Drugs 0.000 description 1
• 229960003130 interferon gamma Drugs 0.000 description 1
• 229940047124 interferons Drugs 0.000 description 1
• 229940047122 interleukins Drugs 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007917 intracranial administration Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007919 intrasynovial administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
• 238000004255 ion exchange chromatography Methods 0.000 description 1
• 229960005386 ipilimumab Drugs 0.000 description 1
• 229940084651 iressa Drugs 0.000 description 1
• 229960004768 irinotecan Drugs 0.000 description 1
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 229950000518 labetuzumab Drugs 0.000 description 1
• 229960004891 lapatinib Drugs 0.000 description 1
• 229940115286 lentinan Drugs 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 229960001691 leucovorin Drugs 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
• 230000000670 limiting effect Effects 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• DHMTURDWPRKSOA-RUZDIDTESA-N lonafarnib Chemical compound C1CN(C(=O)N)CCC1CC(=O)N1CCC([C@@H]2C3=C(Br)C=C(Cl)C=C3CCC3=CC(Br)=CN=C32)CC1 DHMTURDWPRKSOA-RUZDIDTESA-N 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• YROQEQPFUCPDCP-UHFFFAOYSA-N losoxantrone Chemical compound OCCNCCN1N=C2C3=CC=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCNCCO YROQEQPFUCPDCP-UHFFFAOYSA-N 0.000 description 1
• 229950008745 losoxantrone Drugs 0.000 description 1
• 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
• 239000007937 lozenge Substances 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
• 210000003563 lymphoid tissue Anatomy 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
• 229910001623 magnesium bromide Inorganic materials 0.000 description 1
• IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
• RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
• IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
• 201000011614 malignant glioma Diseases 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
• 230000008774 maternal effect Effects 0.000 description 1
• 229950008001 matuzumab Drugs 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
• 230000010534 mechanism of action Effects 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
• 229950009246 mepitiostane Drugs 0.000 description 1
• 229960005108 mepolizumab Drugs 0.000 description 1
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
• 229960001428 mercaptopurine Drugs 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• GQJCAQADCPTHKN-UHFFFAOYSA-N methyl 2,2-difluoro-2-fluorosulfonylacetate Chemical compound COC(=O)C(F)(F)S(F)(=O)=O GQJCAQADCPTHKN-UHFFFAOYSA-N 0.000 description 1
• NPXOIGSBRLCOSD-UHFFFAOYSA-N methyl 3-iodobenzoate Chemical compound COC(=O)C1=CC=CC(I)=C1 NPXOIGSBRLCOSD-UHFFFAOYSA-N 0.000 description 1
• LZGCVVSRZHFYPF-UHFFFAOYSA-N methyl 6-chloro-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(F)C(Cl)=N1 LZGCVVSRZHFYPF-UHFFFAOYSA-N 0.000 description 1
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
• DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
• HRHKSTOGXBBQCB-VFWICMBZSA-N methylmitomycin Chemical compound O=C1C(N)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N(C)[C@H]3CN12 HRHKSTOGXBBQCB-VFWICMBZSA-N 0.000 description 1
• 229960002216 methylparaben Drugs 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
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229960005485 mitobronitol Drugs 0.000 description 1
• 229960003539 mitoguazone Drugs 0.000 description 1
• MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 description 1
• VFKZTMPDYBFSTM-GUCUJZIJSA-N mitolactol Chemical compound BrC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-GUCUJZIJSA-N 0.000 description 1
• 229950010913 mitolactol Drugs 0.000 description 1
• 229960000350 mitotane Drugs 0.000 description 1
• 239000000178 monomer Substances 0.000 description 1
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
• 229960001521 motavizumab Drugs 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 210000004877 mucosa Anatomy 0.000 description 1
• 229960000951 mycophenolic acid Drugs 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
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
• NJSMWLQOCQIOPE-OCHFTUDZSA-N n-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1N\N=C\C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1\C=N\NC1=NCCN1 NJSMWLQOCQIOPE-OCHFTUDZSA-N 0.000 description 1
• LBWFXVZLPYTWQI-IPOVEDGCSA-N n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C LBWFXVZLPYTWQI-IPOVEDGCSA-N 0.000 description 1
• OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 1
• 239000002105 nanoparticle Substances 0.000 description 1
• 125000004957 naphthylene group Chemical group 0.000 description 1
• 229960005027 natalizumab Drugs 0.000 description 1
• 210000000822 natural killer cell Anatomy 0.000 description 1
• 229930014626 natural product Natural products 0.000 description 1
• 229940086322 navelbine Drugs 0.000 description 1
• 239000006199 nebulizer Substances 0.000 description 1
• 230000001537 neural effect Effects 0.000 description 1
• 230000000926 neurological effect Effects 0.000 description 1
• 229940080607 nexavar Drugs 0.000 description 1
• XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
• 229960002653 nilutamide Drugs 0.000 description 1
• KGTDRFCXGRULNK-JYOBTZKQSA-N nogalamycin Chemical compound CO[C@@H]1[C@@](OC)(C)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=C4[C@@]5(C)O[C@H]([C@H]([C@@H]([C@H]5O)N(C)C)O)OC4=C3C3=O)=C3C=C2[C@@H](C(=O)OC)[C@@](C)(O)C1 KGTDRFCXGRULNK-JYOBTZKQSA-N 0.000 description 1
• 229950009266 nogalamycin Drugs 0.000 description 1
• 229940085033 nolvadex Drugs 0.000 description 1
• GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
• ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• KPMKEVXVVHNIEY-RITPCOANSA-N norcamphor Chemical compound C1C[C@@H]2C(=O)C[C@H]1C2 KPMKEVXVVHNIEY-RITPCOANSA-N 0.000 description 1
• BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
• 239000002777 nucleoside Substances 0.000 description 1
• 239000002773 nucleotide Substances 0.000 description 1
• 125000003729 nucleotide group Chemical group 0.000 description 1
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
• 229950005751 ocrelizumab Drugs 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
• 239000004006 olive oil Substances 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• CZDBNBLGZNWKMC-MWQNXGTOSA-N olivomycin Chemical class 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
• 229960000470 omalizumab Drugs 0.000 description 1
• 229950011093 onapristone Drugs 0.000 description 1
• 239000002997 ophthalmic solution Substances 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 238000000643 oven drying Methods 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
• SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003551 oxepanyl group Chemical group 0.000 description 1
• 235000019629 palatability Nutrition 0.000 description 1
• 229960000402 palivizumab Drugs 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-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
• 229950011485 pascolizumab Drugs 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 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
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
• 229950003203 pexelizumab Drugs 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
• 239000000049 pigment Substances 0.000 description 1
• 229960000952 pipobroman Drugs 0.000 description 1
• NJBFOOCLYDNZJN-UHFFFAOYSA-N pipobroman Chemical compound BrCCC(=O)N1CCN(C(=O)CCBr)CC1 NJBFOOCLYDNZJN-UHFFFAOYSA-N 0.000 description 1
• 229960001221 pirarubicin Drugs 0.000 description 1
• 150000003057 platinum Chemical class 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 150000003058 platinum compounds Chemical class 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 108091033319 polynucleotide Proteins 0.000 description 1
• 102000040430 polynucleotide Human genes 0.000 description 1
• 239000002157 polynucleotide Substances 0.000 description 1
• 229920001184 polypeptide Polymers 0.000 description 1
• 229920001282 polysaccharide Polymers 0.000 description 1
• 239000005017 polysaccharide Substances 0.000 description 1
• 238000010837 poor prognosis Methods 0.000 description 1
• 229950004406 porfiromycin Drugs 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 229960004694 prednimustine Drugs 0.000 description 1
• 230000035935 pregnancy Effects 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 150000003138 primary alcohols Chemical class 0.000 description 1
• 208000013846 primary aldosteronism Diseases 0.000 description 1
• 150000003141 primary amines Chemical class 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
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 230000000770 proinflammatory effect Effects 0.000 description 1
• 229940087463 proleukin Drugs 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• UINFICGYFFOSMB-UHFFFAOYSA-N propanoate;pyridin-1-ium Chemical compound CCC(O)=O.C1=CC=NC=C1 UINFICGYFFOSMB-UHFFFAOYSA-N 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• 230000001681 protective effect Effects 0.000 description 1
• 239000003909 protein kinase inhibitor Substances 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• NVZLBPXTJTXPDC-UHFFFAOYSA-N pyrrolo[3,4-e]benzimidazole Chemical class C1=CC2=NC=NC2=C2C=NC=C21 NVZLBPXTJTXPDC-UHFFFAOYSA-N 0.000 description 1
• 125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 230000000171 quenching effect Effects 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 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
• 229960003876 ranibizumab Drugs 0.000 description 1
• 229940099538 rapamune Drugs 0.000 description 1
• BMKDZUISNHGIBY-UHFFFAOYSA-N razoxane Chemical compound C1C(=O)NC(=O)CN1C(C)CN1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-UHFFFAOYSA-N 0.000 description 1
• 229960000460 razoxane Drugs 0.000 description 1
• 210000003289 regulatory T cell Anatomy 0.000 description 1
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 239000013557 residual solvent Substances 0.000 description 1
• 229960003254 reslizumab Drugs 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 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
• 238000007363 ring formation reaction Methods 0.000 description 1
• 229950004892 rodorubicin Drugs 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
• 229950009092 rovelizumab Drugs 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
• 229950005374 ruplizumab Drugs 0.000 description 1
• 229930182947 sarcodictyin Natural products 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• 229950010746 selumetinib Drugs 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• 229950003804 siplizumab Drugs 0.000 description 1
• 238000001542 size-exclusion chromatography Methods 0.000 description 1
• 229950001403 sizofiran Drugs 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
• 239000004299 sodium benzoate Substances 0.000 description 1
• 235000010234 sodium benzoate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• 239000007909 solid dosage form Substances 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 229960003787 sorafenib Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 239000003549 soybean oil Substances 0.000 description 1
• 235000012424 soybean oil Nutrition 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 229950006315 spirogermanium Drugs 0.000 description 1
• ICXJVZHDZFXYQC-UHFFFAOYSA-N spongistatin 1 Natural products OC1C(O2)(O)CC(O)C(C)C2CCCC=CC(O2)CC(O)CC2(O2)CC(OC)CC2CC(=O)C(C)C(OC(C)=O)C(C)C(=C)CC(O2)CC(C)(O)CC2(O2)CC(OC(C)=O)CC2CC(=O)OC2C(O)C(CC(=C)CC(O)C=CC(Cl)=C)OC1C2C ICXJVZHDZFXYQC-UHFFFAOYSA-N 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000000859 sublimation Methods 0.000 description 1
• 230000008022 sublimation Effects 0.000 description 1
• 125000005650 substituted phenylene group Chemical group 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 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 1
• 229960001796 sunitinib Drugs 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 229940034785 sutent Drugs 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 229950001072 tadocizumab Drugs 0.000 description 1
• 229950004218 talizumab Drugs 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
• 238000002626 targeted therapy Methods 0.000 description 1
• 238000003419 tautomerization reaction Methods 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
• 229950001788 tefibazumab 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
• XTDXZSGSIMLARD-UHFFFAOYSA-N tert-butyl 2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC=CC=C1 XTDXZSGSIMLARD-UHFFFAOYSA-N 0.000 description 1
• OFTNEEKVMCCHHQ-UHFFFAOYSA-N tert-butyl 4-(imidazo[1,5-a]pyridine-5-carbonyl)piperidine-1-carboxylate Chemical compound C=1N=CN2C=1C=CC=C2C(=O)C1CCN(CC1)C(=O)OC(C)(C)C OFTNEEKVMCCHHQ-UHFFFAOYSA-N 0.000 description 1
• SYPHEXWHEBYCKR-UHFFFAOYSA-N tert-butyl 4-[2-(4-methylphenyl)sulfonylhydrazinyl]piperidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)NNS(=O)(=O)C1=CC=C(C)C=C1 SYPHEXWHEBYCKR-UHFFFAOYSA-N 0.000 description 1
• KNUVECYIBRFEPS-UHFFFAOYSA-N tert-butyl 4-[hydroxy(imidazo[1,5-a]pyridin-5-yl)methyl]piperidine-1-carboxylate Chemical compound OC(C1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=CC=2N1C=NC=2 KNUVECYIBRFEPS-UHFFFAOYSA-N 0.000 description 1
• XTKKEHQRBTVXBL-UHFFFAOYSA-N tert-butyl N-[[6-(bicyclo[2.2.1]heptane-2-carbonyl)-5-cyclopropylpyridin-2-yl]methyl]carbamate Chemical compound C12C(CC(CC1)C2)C(=O)C1=C(C=CC(=N1)CNC(OC(C)(C)C)=O)C1CC1 XTKKEHQRBTVXBL-UHFFFAOYSA-N 0.000 description 1
• VGDCXKATFLOEHF-UHFFFAOYSA-N tert-butyl n-(3-oxocyclohexyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCCC(=O)C1 VGDCXKATFLOEHF-UHFFFAOYSA-N 0.000 description 1
• XCAQIUOFDMREBA-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(=O)OC(C)(C)C XCAQIUOFDMREBA-UHFFFAOYSA-N 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• BPEWUONYVDABNZ-DZBHQSCQSA-N testolactone Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(OC(=O)CC4)[C@@H]4[C@@H]3CCC2=C1 BPEWUONYVDABNZ-DZBHQSCQSA-N 0.000 description 1
• 229960005353 testolactone Drugs 0.000 description 1
• 229960003604 testosterone Drugs 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical group S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• 239000003768 thromboxane synthase inhibitor Substances 0.000 description 1
• YFTWHEBLORWGNI-UHFFFAOYSA-N tiamiprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC(N)=NC2=C1NC=N2 YFTWHEBLORWGNI-UHFFFAOYSA-N 0.000 description 1
• 229950011457 tiamiprine Drugs 0.000 description 1
• 229960003087 tioguanine Drugs 0.000 description 1
• MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
• 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin Toxicity 0.000 description 1
• 108700012359 toxins Proteins 0.000 description 1
• 229960004066 trametinib Drugs 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 229960001727 tretinoin Drugs 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• PXSOHRWMIRDKMP-UHFFFAOYSA-N triaziquone Chemical compound O=C1C(N2CC2)=C(N2CC2)C(=O)C=C1N1CC1 PXSOHRWMIRDKMP-UHFFFAOYSA-N 0.000 description 1
• 229960004560 triaziquone Drugs 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 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
• WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• 229950000212 trioxifene 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
• 229950010147 troxacitabine Drugs 0.000 description 1
• RXRGZNYSEHTMHC-BQBZGAKWSA-N troxacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)OC1 RXRGZNYSEHTMHC-BQBZGAKWSA-N 0.000 description 1
• 229950003364 tucotuzumab celmoleukin Drugs 0.000 description 1
• 108700008509 tucotuzumab celmoleukin Proteins 0.000 description 1
• 230000005740 tumor formation Effects 0.000 description 1
• 229940094060 tykerb Drugs 0.000 description 1
• 229950009811 ubenimex Drugs 0.000 description 1
• 229960001055 uracil mustard Drugs 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 229950004362 urtoxazumab Drugs 0.000 description 1
• 238000002255 vaccination Methods 0.000 description 1
• FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
• 235000012141 vanillin Nutrition 0.000 description 1
• MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 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
• 239000003981 vehicle Substances 0.000 description 1
• 229940099039 velcade Drugs 0.000 description 1
• 229960003048 vinblastine Drugs 0.000 description 1
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
• 229960004528 vincristine Drugs 0.000 description 1
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
• 229960004355 vindesine Drugs 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
• GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 1
• 229960002066 vinorelbine Drugs 0.000 description 1
• CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 229950004393 visilizumab Drugs 0.000 description 1
• 229960001771 vorozole Drugs 0.000 description 1
• XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1
• 239000008215 water for injection Substances 0.000 description 1
• 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 1
• 229940053867 xeloda Drugs 0.000 description 1
• 229950009268 zinostatin Drugs 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