TW201643157A - Ｇｄｆ－８抑制劑 - Google Patents

Info

Publication number

TW201643157A

TW201643157A TW105104992A TW105104992A TW201643157A TW 201643157 A TW201643157 A TW 201643157A TW 105104992 A TW105104992 A TW 105104992A TW 105104992 A TW105104992 A TW 105104992A TW 201643157 A TW201643157 A TW 201643157A

Authority

TW

Taiwan

Prior art keywords

alkyl

haloalkyl

bipyridyl

imidazo

het

Prior art date

2015-02-20

Links

• Espacenet
• Global Dossier
• Discuss

• 108010056852 Myostatin Proteins 0.000 title claims description 56
• 102000004472 Myostatin Human genes 0.000 title claims 5
• 239000003112 inhibitor Substances 0.000 title description 14
• 150000001875 compounds Chemical class 0.000 claims abstract description 490
• 238000000034 method Methods 0.000 claims abstract description 217
• 150000003839 salts Chemical class 0.000 claims abstract description 75
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
• 201000010099 disease Diseases 0.000 claims abstract description 45
• 229940002612 prodrug Drugs 0.000 claims abstract description 40
• 239000000651 prodrug Substances 0.000 claims abstract description 40
• 239000012453 solvate Substances 0.000 claims abstract description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 27
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims abstract description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 178
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 173
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 172
• 229910052736 halogen Inorganic materials 0.000 claims description 143
• 150000002367 halogens Chemical class 0.000 claims description 143
• 229910052739 hydrogen Inorganic materials 0.000 claims description 125
• 239000001257 hydrogen Substances 0.000 claims description 121
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 115
• 150000002431 hydrogen Chemical class 0.000 claims description 93
• 125000001188 haloalkyl group Chemical group 0.000 claims description 55
• 125000003118 aryl group Chemical group 0.000 claims description 42
• 125000002619 bicyclic group Chemical group 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 34
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 31
• 210000003205 muscle Anatomy 0.000 claims description 28
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 24
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 23
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
• ZMBYQTGAXZOMOO-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CC=CN2C(C(=O)N)=CN=C21 ZMBYQTGAXZOMOO-UHFFFAOYSA-N 0.000 claims description 17
• 201000006938 muscular dystrophy Diseases 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 230000002401 inhibitory effect Effects 0.000 claims description 16
• 241000124008 Mammalia Species 0.000 claims description 15
• 239000003085 diluting agent Substances 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 13
• DREUPRFRJOSEAM-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=CC=CN2C(C#N)=CN=C21 DREUPRFRJOSEAM-UHFFFAOYSA-N 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 12
• 208000001132 Osteoporosis Diseases 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical class NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims description 10
• 238000002560 therapeutic procedure Methods 0.000 claims description 10
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 10
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 9
• 210000000988 bone and bone Anatomy 0.000 claims description 9
• 208000011580 syndromic disease Diseases 0.000 claims description 9
• PEKUAWGDFMCYPI-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C=CN=2 PEKUAWGDFMCYPI-UHFFFAOYSA-N 0.000 claims description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
• 208000026062 Tissue disease Diseases 0.000 claims description 7
• 210000000577 adipose tissue Anatomy 0.000 claims description 7
• 208000035475 disorder Diseases 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 6
• 238000000338 in vitro Methods 0.000 claims description 6
• 235000020824 obesity Nutrition 0.000 claims description 6
• 208000001076 sarcopenia Diseases 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• KWJNYONYDWUEKL-UHFFFAOYSA-N CC1=CC=CC(=N1)C1=NC=CC=C1C1=C2C3=CC=CCC3=NC2=CC=C1 Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=C2C3=CC=CCC3=NC2=CC=C1 KWJNYONYDWUEKL-UHFFFAOYSA-N 0.000 claims description 5
• 206010006895 Cachexia Diseases 0.000 claims description 5
• 208000011623 Obstructive Lung disease Diseases 0.000 claims description 5
• 230000037182 bone density Effects 0.000 claims description 5
• 235000019253 formic acid Nutrition 0.000 claims description 5
• 208000018360 neuromuscular disease Diseases 0.000 claims description 5
• 235000005152 nicotinamide Nutrition 0.000 claims description 5
• 239000011570 nicotinamide Substances 0.000 claims description 5
• XBRZTHDHIMYWLN-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N XBRZTHDHIMYWLN-UHFFFAOYSA-N 0.000 claims description 4
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 4
• 206010022489 Insulin Resistance Diseases 0.000 claims description 4
• 208000029578 Muscle disease Diseases 0.000 claims description 4
• 208000021642 Muscular disease Diseases 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 208000014674 injury Diseases 0.000 claims description 4
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 4
• 230000008733 trauma Effects 0.000 claims description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
• PEFYDHOUMOOYOE-UHFFFAOYSA-N 6-(2-pyridin-2-ylpyridin-3-yl)quinazolin-4-amine Chemical compound N1=C(C(=CC=C1)C=1C=C2C(=NC=NC2=CC=1)N)C1=NC=CC=C1 PEFYDHOUMOOYOE-UHFFFAOYSA-N 0.000 claims description 3
• DGFSIJYSSFFQNN-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N DGFSIJYSSFFQNN-UHFFFAOYSA-N 0.000 claims description 3
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 3
• 208000002720 Malnutrition Diseases 0.000 claims description 3
• 206010047626 Vitamin D Deficiency Diseases 0.000 claims description 3
• 239000003098 androgen Substances 0.000 claims description 3
• 230000001684 chronic effect Effects 0.000 claims description 3
• 239000003862 glucocorticoid Substances 0.000 claims description 3
• 208000030159 metabolic disease Diseases 0.000 claims description 3
• 150000002825 nitriles Chemical class 0.000 claims description 3
• 230000002028 premature Effects 0.000 claims description 3
• XMRIUEGHBZTNND-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC=NC2=C(C(=O)N)C=NN21 XMRIUEGHBZTNND-UHFFFAOYSA-N 0.000 claims description 3
• HNYVPKNVKSTVJO-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=NC2=C(C(=O)O)C=NN21 HNYVPKNVKSTVJO-UHFFFAOYSA-N 0.000 claims description 3
• 230000001629 suppression Effects 0.000 claims description 3
• 235000000112 undernutrition Nutrition 0.000 claims description 3
• LVLOTYIMYWLIDK-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-pyridin-4-ylpyrazolo[1,5-a]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=C2N=CC(C=3C=CN=CC=3)=CN2N=C1 LVLOTYIMYWLIDK-UHFFFAOYSA-N 0.000 claims description 2
• GLVMHLFIFCVTSY-UHFFFAOYSA-N 6-[2-(4-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N GLVMHLFIFCVTSY-UHFFFAOYSA-N 0.000 claims description 2
• IPTBQVPQHNXVFY-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N IPTBQVPQHNXVFY-UHFFFAOYSA-N 0.000 claims description 2
• YZIMZSCGXKSDIL-UHFFFAOYSA-N 6-[2-(5-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound CC=1C=CC(=NC=1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N YZIMZSCGXKSDIL-UHFFFAOYSA-N 0.000 claims description 2
• LBHOAKVBSFBSEX-UHFFFAOYSA-N 6-[2-(6-methoxypyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound COC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N LBHOAKVBSFBSEX-UHFFFAOYSA-N 0.000 claims description 2
• ZORXRGAPSQEFGA-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)N=CN=2 ZORXRGAPSQEFGA-UHFFFAOYSA-N 0.000 claims description 2
• XHPVHXBWWXRLEP-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]quinazolin-4-amine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2C(=NC=NC2=CC=1)N XHPVHXBWWXRLEP-UHFFFAOYSA-N 0.000 claims description 2
• LXJVYERTNJFFFB-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N)F LXJVYERTNJFFFB-UHFFFAOYSA-N 0.000 claims description 2
• NFOWFTIOEIHVID-UHFFFAOYSA-N 6-[4-(difluoromethyl)-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC(C1=C(C(=NC=C1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C#N)F NFOWFTIOEIHVID-UHFFFAOYSA-N 0.000 claims description 2
• 230000008901 benefit Effects 0.000 claims description 2
• 239000004202 carbamide Substances 0.000 claims description 2
• 230000003412 degenerative effect Effects 0.000 claims description 2
• 230000002710 gonadal effect Effects 0.000 claims description 2
• YLXWTAXPOOYRSL-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1=CC=NN2C(C#N)=CN=C21 YLXWTAXPOOYRSL-UHFFFAOYSA-N 0.000 claims description 2
• 229960000485 methotrexate Drugs 0.000 claims description 2
• DGXAOSOMFMODCF-UHFFFAOYSA-N pyrido[3,2-d]pyrimidin-4-amine Chemical compound C1=CN=C2C(N)=NC=NC2=C1 DGXAOSOMFMODCF-UHFFFAOYSA-N 0.000 claims 4
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
• 150000001925 cycloalkenes Chemical class 0.000 claims 2
• NBEWMBVUHSPONV-UHFFFAOYSA-N quinazolin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2C(N)=NC=NC2=C1 NBEWMBVUHSPONV-UHFFFAOYSA-N 0.000 claims 2
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
• 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 claims 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
• WRPFUIWJWHZDCJ-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)pyridin-3-yl]quinoline Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=CC=NC2=CC=CC=C12 WRPFUIWJWHZDCJ-UHFFFAOYSA-N 0.000 claims 1
• IYAZEYWWCVJQQK-UHFFFAOYSA-N CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N1)C(=CN2)C(=O)N.CC2=CC=CC(=N2)C2=NC=CC=C2C=2C=CC=1N(N2)C(=CN1)C#N Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N1)C(=CN2)C(=O)N.CC2=CC=CC(=N2)C2=NC=CC=C2C=2C=CC=1N(N2)C(=CN1)C#N IYAZEYWWCVJQQK-UHFFFAOYSA-N 0.000 claims 1
• XSQMJCHSDMZRFE-UHFFFAOYSA-N CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N1)C(=CN2)C(=O)O.CC=2N=C1N(C=C(C=C1)C=1C(=NC=CC1)C1=NC(=CC=C1)C)C2C(=O)N Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N1)C(=CN2)C(=O)O.CC=2N=C1N(C=C(C=C1)C=1C(=NC=CC1)C1=NC(=CC=C1)C)C2C(=O)N XSQMJCHSDMZRFE-UHFFFAOYSA-N 0.000 claims 1
• QOEYIVHGERGLFU-UHFFFAOYSA-N FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C(=O)N)(F)F.COC2=CC=CC(=N2)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C#N Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C(=O)N)(F)F.COC2=CC=CC(=N2)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C#N QOEYIVHGERGLFU-UHFFFAOYSA-N 0.000 claims 1
• VIQUZGMJVPASJF-UHFFFAOYSA-N FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N.FC=2C=CC(=NC2C)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C#N Chemical compound FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N.FC=2C=CC(=NC2C)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C#N VIQUZGMJVPASJF-UHFFFAOYSA-N 0.000 claims 1
• JMSSBXWFEQTNHJ-UHFFFAOYSA-N FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C(=O)N.FC=2C=CC(=NC2)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C(=O)N Chemical compound FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C(=O)N.FC=2C=CC(=NC2)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C(=O)N JMSSBXWFEQTNHJ-UHFFFAOYSA-N 0.000 claims 1
• AGFVFOBJWDIEAV-UHFFFAOYSA-N FC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N.C2(CC2)C2=CC=CC(=N2)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C(=O)N Chemical compound FC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N.C2(CC2)C2=CC=CC(=N2)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C(=O)N AGFVFOBJWDIEAV-UHFFFAOYSA-N 0.000 claims 1
• CICCIAANPRXACT-UHFFFAOYSA-N FC=1C=CC(=NC1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N.FC=2C=CC(=NC2C)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C(=O)N Chemical compound FC=1C=CC(=NC1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N.FC=2C=CC(=NC2C)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C(=O)N CICCIAANPRXACT-UHFFFAOYSA-N 0.000 claims 1
• RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 1
• ZNRNNIUKMCIEAZ-UHFFFAOYSA-N N-(2,2-difluoroethyl)-6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound Cc1cccc(n1)-c1ncccc1-c1ccc2ncc(C(O)=O)n2c1.Cc1cccc(n1)-c1ncccc1-c1ccc2ncc(C(=O)NCC(F)F)n2c1 ZNRNNIUKMCIEAZ-UHFFFAOYSA-N 0.000 claims 1
• OLANRYCHDPJMJQ-UHFFFAOYSA-N N-methyl-5-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)C=1C=NN2C=1N=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C(F)(F)F OLANRYCHDPJMJQ-UHFFFAOYSA-N 0.000 claims 1
• RJALCGMLLASKMR-UHFFFAOYSA-N ethyl 5-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylate 5-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound Cc1nc(ccc1F)-c1ncccc1-c1ccn2ncc(C#N)c2n1.CCOC(=O)c1cnn2ccc(nc12)-c1cccnc1-c1cccc(n1)C(F)(F)F RJALCGMLLASKMR-UHFFFAOYSA-N 0.000 claims 1
• ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 1
• DOGXPDFZEQXZDS-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound C1=CC=CN2C(C(=O)O)=CN=C21 DOGXPDFZEQXZDS-UHFFFAOYSA-N 0.000 claims 1
• 125000003566 oxetanyl group Chemical group 0.000 claims 1
• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims 1
• RRHORVAOECWFPT-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound C1=CC=NC2=C(C#N)C=NN21 RRHORVAOECWFPT-UHFFFAOYSA-N 0.000 claims 1
• GZPHSAQLYPIAIN-DOMIDYPGSA-N pyridine-3-carbonitrile Chemical compound N#[14C]c1cccnc1 GZPHSAQLYPIAIN-DOMIDYPGSA-N 0.000 claims 1
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 1
• 102100039939 Growth/differentiation factor 8 Human genes 0.000 abstract description 58
• 230000011664 signaling Effects 0.000 abstract description 17
• 101000886562 Homo sapiens Growth/differentiation factor 8 Proteins 0.000 abstract description 8
• 150000001204 N-oxides Chemical class 0.000 abstract description 2
• 230000000903 blocking effect Effects 0.000 abstract 1
• 150000004677 hydrates Chemical class 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 228
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 192
• 238000005481 NMR spectroscopy Methods 0.000 description 150
• 238000002474 experimental method Methods 0.000 description 133
• 238000002953 preparative HPLC Methods 0.000 description 105
• 235000019439 ethyl acetate Nutrition 0.000 description 98
• 239000011541 reaction mixture Substances 0.000 description 68
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
• 239000000203 mixture Substances 0.000 description 63
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
• 239000007787 solid Substances 0.000 description 53
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 48
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
• 239000000243 solution Substances 0.000 description 48
• 238000006243 chemical reaction Methods 0.000 description 46
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 38
• 230000008569 process Effects 0.000 description 37
• 230000002829 reductive effect Effects 0.000 description 36
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• 239000000460 chlorine Substances 0.000 description 31
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
• 238000010898 silica gel chromatography Methods 0.000 description 29
• 238000011282 treatment Methods 0.000 description 29
• 239000012044 organic layer Substances 0.000 description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• 239000003208 petroleum Substances 0.000 description 25
• 206010028980 Neoplasm Diseases 0.000 description 24
• 238000002360 preparation method Methods 0.000 description 24
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 23
• 239000000047 product Substances 0.000 description 23
• 206010057190 Respiratory tract infections Diseases 0.000 description 22
• 210000004027 cell Anatomy 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• 239000002253 acid Substances 0.000 description 21
• 229910052757 nitrogen Inorganic materials 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• 229910052786 argon Inorganic materials 0.000 description 19
• 239000011734 sodium Substances 0.000 description 18
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
• 201000011510 cancer Diseases 0.000 description 16
• 239000012043 crude product Substances 0.000 description 16
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 16
• 230000014759 maintenance of location Effects 0.000 description 16
• 125000000753 cycloalkyl group Chemical group 0.000 description 15
• 230000005764 inhibitory process Effects 0.000 description 15
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
• USKQYZHWJZDNCM-UHFFFAOYSA-N tributyl-(6-methylpyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC(C)=N1 USKQYZHWJZDNCM-UHFFFAOYSA-N 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 238000004458 analytical method Methods 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• 238000000746 purification Methods 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• BFQONZCQHGIKIY-UHFFFAOYSA-N 6-bromo-3-fluoro-2-methylpyridine Chemical compound CC1=NC(Br)=CC=C1F BFQONZCQHGIKIY-UHFFFAOYSA-N 0.000 description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 12
• 229910052717 sulfur Inorganic materials 0.000 description 12
• 238000003786 synthesis reaction Methods 0.000 description 12
• 230000001225 therapeutic effect Effects 0.000 description 12
• 239000004480 active ingredient Substances 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 108090000623 proteins and genes Proteins 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• BCIZTVUZIPWHOT-UHFFFAOYSA-N N-(2,2-difluoroethyl)-6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC(CNC(=O)C1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C)F BCIZTVUZIPWHOT-UHFFFAOYSA-N 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
• 229910052799 carbon Inorganic materials 0.000 description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
• 102000004169 proteins and genes Human genes 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• ZTBGDNNRDRISQZ-UHFFFAOYSA-N 2-bromo-6-(difluoromethyl)pyridine Chemical compound FC(F)C1=CC=CC(Br)=N1 ZTBGDNNRDRISQZ-UHFFFAOYSA-N 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 102000046299 Transforming Growth Factor beta1 Human genes 0.000 description 9
• 101800002279 Transforming growth factor beta-1 Proteins 0.000 description 9
• 239000000872 buffer Substances 0.000 description 9
• SADFDFDVVYTIAV-UHFFFAOYSA-N ethyl 5-(2-chloropyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound N=1C2=C(C(=O)OCC)C=NN2C=CC=1C1=CC=CN=C1Cl SADFDFDVVYTIAV-UHFFFAOYSA-N 0.000 description 9
• 238000001727 in vivo Methods 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 208000024891 symptom Diseases 0.000 description 9
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 8
• DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 8
• VPTKKRSNMHQWEN-UHFFFAOYSA-N 5-(2-chloropyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C1=NC2=C(C#N)C=NN2C=C1 VPTKKRSNMHQWEN-UHFFFAOYSA-N 0.000 description 8
• UFYNPYSBFUFLET-UHFFFAOYSA-N 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)O UFYNPYSBFUFLET-UHFFFAOYSA-N 0.000 description 8
• PJSBOEVNEUCHIG-UHFFFAOYSA-N 6-bromoimidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=C(Br)C=CC2=NC=C(C#N)N21 PJSBOEVNEUCHIG-UHFFFAOYSA-N 0.000 description 8
• CSXFALIKHGXFNG-UHFFFAOYSA-N ClC1=NC=CC=C1C1=NC2=CC=NN2C=C1 Chemical compound ClC1=NC=CC=C1C1=NC2=CC=NN2C=C1 CSXFALIKHGXFNG-UHFFFAOYSA-N 0.000 description 8
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
• 230000004913 activation Effects 0.000 description 8
• 239000002246 antineoplastic agent Substances 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 239000012141 concentrate Substances 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• XSALNTVCPDIVQL-UHFFFAOYSA-N ethyl 6-(2-chloropyridin-3-yl)imidazo[1,2-a]pyridine-2-carboxylate Chemical compound ClC1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)C(=O)OCC XSALNTVCPDIVQL-UHFFFAOYSA-N 0.000 description 8
• 229910052731 fluorine Inorganic materials 0.000 description 8
• 150000002500 ions Chemical class 0.000 description 8
• GCRPZQJTCLRZHM-UHFFFAOYSA-N 6-(2-chloro-5-fluoropyridin-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound ClC1=NC=C(C=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)F GCRPZQJTCLRZHM-UHFFFAOYSA-N 0.000 description 7
• QNXVRAQRKVCDJG-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N QNXVRAQRKVCDJG-UHFFFAOYSA-N 0.000 description 7
• HIWNRWJGMZGEBC-UHFFFAOYSA-N 6-[2-(5-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound CC=1C=CC(=NC=1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N HIWNRWJGMZGEBC-UHFFFAOYSA-N 0.000 description 7
• DDLRSTPDXCUOSI-UHFFFAOYSA-N 6-[2-(6-methoxypyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound COC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N DDLRSTPDXCUOSI-UHFFFAOYSA-N 0.000 description 7
• TYADPDFBGMXEES-UHFFFAOYSA-N 6-[2-(6-methoxypyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound COC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N TYADPDFBGMXEES-UHFFFAOYSA-N 0.000 description 7
• HWKJOTIADMVNGT-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N HWKJOTIADMVNGT-UHFFFAOYSA-N 0.000 description 7
• 108010059616 Activins Proteins 0.000 description 7
• 102000004127 Cytokines Human genes 0.000 description 7
• 108090000695 Cytokines Proteins 0.000 description 7
• 102000004190 Enzymes Human genes 0.000 description 7
• 108090000790 Enzymes Proteins 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
• LNYFKIMKJCFZGW-UHFFFAOYSA-N N-(5-bromo-6-chloropyridin-2-yl)acetamide Chemical compound BrC=1C=CC(=NC=1Cl)NC(C)=O LNYFKIMKJCFZGW-UHFFFAOYSA-N 0.000 description 7
• RPSSZGUTFLZTKP-UHFFFAOYSA-N N-[6-(2-chloropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl]acetamide Chemical compound ClC1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)NC(C)=O RPSSZGUTFLZTKP-UHFFFAOYSA-N 0.000 description 7
• BFSRDMCDMBWICA-UHFFFAOYSA-N N-tert-butyl-6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-amine Chemical compound C(C)(C)(C)NC1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C BFSRDMCDMBWICA-UHFFFAOYSA-N 0.000 description 7
• 108091000080 Phosphotransferase Proteins 0.000 description 7
• 239000000488 activin Substances 0.000 description 7
• 238000003016 alphascreen Methods 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 235000008504 concentrate Nutrition 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• QQPSMBSRIMQOSV-UHFFFAOYSA-N ethyl 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-2-carboxylate Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)C(=O)OCC QQPSMBSRIMQOSV-UHFFFAOYSA-N 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 125000005842 heteroatom Chemical group 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 229910052760 oxygen Inorganic materials 0.000 description 7
• 102000020233 phosphotransferase Human genes 0.000 description 7
• 125000000168 pyrrolyl group Chemical group 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• LQUPKVMEAATBSL-UHFFFAOYSA-L zinc;2,3,4-trichlorophenolate Chemical compound [Zn+2].[O-]C1=CC=C(Cl)C(Cl)=C1Cl.[O-]C1=CC=C(Cl)C(Cl)=C1Cl LQUPKVMEAATBSL-UHFFFAOYSA-L 0.000 description 7
• DOWNSQADAFSSAR-UHFFFAOYSA-N 2-bromo-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC(Br)=N1 DOWNSQADAFSSAR-UHFFFAOYSA-N 0.000 description 6
• BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 6
• BUTBOALODZMXJV-UHFFFAOYSA-N 5-bromo-6-chloropyridin-2-amine Chemical compound NC1=CC=C(Br)C(Cl)=N1 BUTBOALODZMXJV-UHFFFAOYSA-N 0.000 description 6
• VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 6
• QEEXHURNWUCAMA-UHFFFAOYSA-N 6-[2-(5-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC=1C=CC(=NC=1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N QEEXHURNWUCAMA-UHFFFAOYSA-N 0.000 description 6
• AFJWJMZWZKJRHX-UHFFFAOYSA-N 6-[2-(6-chloropyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound ClC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N AFJWJMZWZKJRHX-UHFFFAOYSA-N 0.000 description 6
• NDSLJYBNARFCFA-UHFFFAOYSA-N 6-[2-(6-ethylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N NDSLJYBNARFCFA-UHFFFAOYSA-N 0.000 description 6
• YTQLKYUMURCZOM-UHFFFAOYSA-N 6-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound ClC1=NC(=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)C(F)(F)F YTQLKYUMURCZOM-UHFFFAOYSA-N 0.000 description 6
• PZOYBOHXXXDAMU-UHFFFAOYSA-N ClC1=NC=CC=C1C1=CN2C(C#N)=CN=C2C=C1 Chemical compound ClC1=NC=CC=C1C1=CN2C(C#N)=CN=C2C=C1 PZOYBOHXXXDAMU-UHFFFAOYSA-N 0.000 description 6
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
• PDKQPFBMCBYZSC-UHFFFAOYSA-N N-(5-bromo-6-chloropyridin-3-yl)acetamide Chemical compound C(C)(=O)NC=1C=NC(=C(C=1)Br)Cl PDKQPFBMCBYZSC-UHFFFAOYSA-N 0.000 description 6
• 102000004887 Transforming Growth Factor beta Human genes 0.000 description 6
• 108090001012 Transforming Growth Factor beta Proteins 0.000 description 6
• 239000011324 bead Substances 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 238000002648 combination therapy Methods 0.000 description 6
• 238000001514 detection method Methods 0.000 description 6
• 239000000796 flavoring agent Substances 0.000 description 6
• 239000011737 fluorine Substances 0.000 description 6
• 239000002609 medium Substances 0.000 description 6
• XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 6
• 231100000252 nontoxic Toxicity 0.000 description 6
• 230000003000 nontoxic effect Effects 0.000 description 6
• 230000007170 pathology Effects 0.000 description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
• 239000002002 slurry Substances 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 239000003765 sweetening agent Substances 0.000 description 6
• UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 6
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 5
• POSVEUQJMIKKGF-UHFFFAOYSA-N 5-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)O POSVEUQJMIKKGF-UHFFFAOYSA-N 0.000 description 5
• YCRXUCWREMOUMS-UHFFFAOYSA-N 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C#N YCRXUCWREMOUMS-UHFFFAOYSA-N 0.000 description 5
• 241000282412 Homo Species 0.000 description 5
• 102100026818 Inhibin beta E chain Human genes 0.000 description 5
• ICBNLDGOFYONAK-UHFFFAOYSA-N N-[3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-2-(6-methylpyridin-2-yl)pyridin-4-yl]acetamide Chemical compound C(#N)C1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1NC(C)=O)C1=NC(=CC=C1)C ICBNLDGOFYONAK-UHFFFAOYSA-N 0.000 description 5
• PNBAQXQLLRURKK-UHFFFAOYSA-N N-[6-chloro-5-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridin-3-yl]acetamide Chemical compound ClC1=C(C=C(C=N1)NC(C)=O)C=1C=CC=2N(C=1)C(=CN=2)C#N PNBAQXQLLRURKK-UHFFFAOYSA-N 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 229940125758 compound 15 Drugs 0.000 description 5
• 239000007859 condensation product Substances 0.000 description 5
• 239000013058 crude material Substances 0.000 description 5
• 229940127089 cytotoxic agent Drugs 0.000 description 5
• 238000007872 degassing Methods 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• WFQBACJZFNFDAD-UHFFFAOYSA-N ethyl 5-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)OCC WFQBACJZFNFDAD-UHFFFAOYSA-N 0.000 description 5
• FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• 239000012065 filter cake Substances 0.000 description 5
• 235000003599 food sweetener Nutrition 0.000 description 5
• 238000004128 high performance liquid chromatography Methods 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• 150000002460 imidazoles Chemical class 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 235000019198 oils Nutrition 0.000 description 5
• 125000002971 oxazolyl group Chemical group 0.000 description 5
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 5
• 239000003755 preservative agent Substances 0.000 description 5
• 230000002265 prevention Effects 0.000 description 5
• PJESVVYWPFAJCS-UHFFFAOYSA-N pyridazine-3-carbonitrile Chemical compound N#CC1=CC=CN=N1 PJESVVYWPFAJCS-UHFFFAOYSA-N 0.000 description 5
• 125000004076 pyridyl group Chemical group 0.000 description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 210000002027 skeletal muscle Anatomy 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 5
• 125000001544 thienyl group Chemical group 0.000 description 5
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 5
• 125000004953 trihalomethyl group Chemical group 0.000 description 5
• 239000003981 vehicle Substances 0.000 description 5
• UZKRYDHOEMBIPL-UHFFFAOYSA-N 2,2,2-trifluoro-N-[6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]acetamide Chemical compound FC(C(=O)NC1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C)(F)F UZKRYDHOEMBIPL-UHFFFAOYSA-N 0.000 description 4
• UODINHBLNPPDPD-UHFFFAOYSA-N 2-bromo-5-fluoropyridine Chemical compound FC1=CC=C(Br)N=C1 UODINHBLNPPDPD-UHFFFAOYSA-N 0.000 description 4
• KTWAUKYSQFZIET-UHFFFAOYSA-N 3-bromo-2-chloropyridin-4-amine Chemical compound NC1=CC=NC(Cl)=C1Br KTWAUKYSQFZIET-UHFFFAOYSA-N 0.000 description 4
• JANOYUBMAIISDE-UHFFFAOYSA-N 5-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2 JANOYUBMAIISDE-UHFFFAOYSA-N 0.000 description 4
• YVGRBVRWQJAYOX-UHFFFAOYSA-N 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2 YVGRBVRWQJAYOX-UHFFFAOYSA-N 0.000 description 4
• WOWFGKMSMRXUJK-UHFFFAOYSA-N 5-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2)(F)F WOWFGKMSMRXUJK-UHFFFAOYSA-N 0.000 description 4
• DMDDVWCMVDTQTD-UHFFFAOYSA-N 5-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C#N)(F)F DMDDVWCMVDTQTD-UHFFFAOYSA-N 0.000 description 4
• FGDDJMSOVWYXMH-UHFFFAOYSA-N 6-[2-(4-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N FGDDJMSOVWYXMH-UHFFFAOYSA-N 0.000 description 4
• MYBPGHUWEGPRFF-UHFFFAOYSA-N 6-[2-(5-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC=1C=CC(=NC=1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N MYBPGHUWEGPRFF-UHFFFAOYSA-N 0.000 description 4
• YCBKRCCFJLNHQE-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrido[3,2-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N=CN=C(C=2N=1)N YCBKRCCFJLNHQE-UHFFFAOYSA-N 0.000 description 4
• RVGIAPWTDZWMLT-UHFFFAOYSA-N 6-[2-(6-phenylmethoxypyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C(C1=CC=CC=C1)OC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N RVGIAPWTDZWMLT-UHFFFAOYSA-N 0.000 description 4
• ISFLACUTKWVCAC-UHFFFAOYSA-N 6-[2-[6-(2-hydroxypropan-2-yl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound OC(C)(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N ISFLACUTKWVCAC-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
• CMYQHWZVQCDSPL-UHFFFAOYSA-N N-[6-[3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]pyridin-2-yl]methanesulfonamide Chemical compound C(#N)C1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)NS(=O)(=O)C CMYQHWZVQCDSPL-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 4
• 239000007900 aqueous suspension Substances 0.000 description 4
• 125000003710 aryl alkyl group Chemical group 0.000 description 4
• 238000003556 assay Methods 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• 230000004071 biological effect Effects 0.000 description 4
• 230000003197 catalytic effect Effects 0.000 description 4
• 239000003086 colorant Substances 0.000 description 4
• 125000004122 cyclic group Chemical group 0.000 description 4
• 230000004069 differentiation Effects 0.000 description 4
• 239000012895 dilution Substances 0.000 description 4
• 238000010790 dilution Methods 0.000 description 4
• 239000002270 dispersing agent Substances 0.000 description 4
• CBBYQFOUGMXCSO-UHFFFAOYSA-N ethyl 5-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)OCC)(F)F CBBYQFOUGMXCSO-UHFFFAOYSA-N 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 125000003709 fluoroalkyl group Chemical group 0.000 description 4
• 235000013355 food flavoring agent Nutrition 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• 125000000524 functional group Chemical group 0.000 description 4
• 125000002541 furyl group Chemical group 0.000 description 4
• 239000008241 heterogeneous mixture Substances 0.000 description 4
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
• 239000012139 lysis buffer Substances 0.000 description 4
• 125000006574 non-aromatic ring group Chemical group 0.000 description 4
• 230000036961 partial effect Effects 0.000 description 4
• 108090000765 processed proteins & peptides Proteins 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 125000002098 pyridazinyl group Chemical group 0.000 description 4
• 239000011535 reaction buffer Substances 0.000 description 4
• 108020003175 receptors Proteins 0.000 description 4
• 102000005962 receptors Human genes 0.000 description 4
• 239000000523 sample Substances 0.000 description 4
• 235000011121 sodium hydroxide Nutrition 0.000 description 4
• 239000000375 suspending agent Substances 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 125000003831 tetrazolyl group Chemical group 0.000 description 4
• 229940124597 therapeutic agent Drugs 0.000 description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 description 4
• 125000000335 thiazolyl group Chemical group 0.000 description 4
• 125000001425 triazolyl group Chemical group 0.000 description 4
• 239000003643 water by type Substances 0.000 description 4
• JSTYQZIXEXOPBT-UHFFFAOYSA-M zinc;6-methyl-2h-pyridin-2-ide;bromide Chemical compound Br[Zn+].CC1=CC=C[C-]=N1 JSTYQZIXEXOPBT-UHFFFAOYSA-M 0.000 description 4
• GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 3
• VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 3
• FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 3
• HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 3
• QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 3
• ZVQSZDKUCGKHQL-UHFFFAOYSA-N 2-bromo-6-cyclopropylpyridine Chemical compound BrC1=CC=CC(C2CC2)=N1 ZVQSZDKUCGKHQL-UHFFFAOYSA-N 0.000 description 3
• GNBUFPXDJYBELS-UHFFFAOYSA-N 2-bromo-6-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CC(Br)=N1 GNBUFPXDJYBELS-UHFFFAOYSA-N 0.000 description 3
• DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
• GYJCRNGOIVXMOZ-UHFFFAOYSA-N 3-bromo-2-chloro-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Br)C(Cl)=N1 GYJCRNGOIVXMOZ-UHFFFAOYSA-N 0.000 description 3
• VYVFQWCUFJMVFL-UHFFFAOYSA-N 5-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C#N VYVFQWCUFJMVFL-UHFFFAOYSA-N 0.000 description 3
• ZCRNNAKWJKIYPJ-UHFFFAOYSA-N 6-(2-chloropyridin-3-yl)-4-methoxypyrido[3,2-d]pyrimidine Chemical compound N1=C2C(OC)=NC=NC2=CC=C1C1=CC=CN=C1Cl ZCRNNAKWJKIYPJ-UHFFFAOYSA-N 0.000 description 3
• UWUQLGVBJRWMKC-UHFFFAOYSA-N 6-(2-chloropyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound ClC1=NC=CC=C1C1=CN2N=CN=C2C=C1 UWUQLGVBJRWMKC-UHFFFAOYSA-N 0.000 description 3
• MLQWBUIJGQCCMK-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N MLQWBUIJGQCCMK-UHFFFAOYSA-N 0.000 description 3
• QADKUNMXABEZML-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N QADKUNMXABEZML-UHFFFAOYSA-N 0.000 description 3
• ZIJNFTAGWWLARB-UHFFFAOYSA-N 6-[4-(difluoromethyl)-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC(C1=C(C(=NC=C1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C(=O)N)F ZIJNFTAGWWLARB-UHFFFAOYSA-N 0.000 description 3
• XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 241000283690 Bos taurus Species 0.000 description 3
• UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 3
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
• 241000699670 Mus sp. Species 0.000 description 3
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 3
• CQEUXRPEMFBFGF-UHFFFAOYSA-N N-[6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridin-2-yl]acetamide Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)NC(C)=O CQEUXRPEMFBFGF-UHFFFAOYSA-N 0.000 description 3
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 239000000370 acceptor Substances 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• 125000002947 alkylene group Chemical group 0.000 description 3
• 230000000259 anti-tumor effect Effects 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
• 229910052801 chlorine Inorganic materials 0.000 description 3
• HODHLQXRQOHAAZ-UHFFFAOYSA-M chloropalladium(1+);dicyclohexyl-[2-(2,6-dimethoxyphenyl)phenyl]phosphane;2-phenylaniline Chemical compound [Pd+]Cl.NC1=CC=CC=C1C1=CC=CC=[C-]1.COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 HODHLQXRQOHAAZ-UHFFFAOYSA-M 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• 229940126086 compound 21 Drugs 0.000 description 3
• 229940125900 compound 59 Drugs 0.000 description 3
• 229940126179 compound 72 Drugs 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 238000003745 diagnosis Methods 0.000 description 3
• 229920001971 elastomer Polymers 0.000 description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
• 239000003102 growth factor Substances 0.000 description 3
• 125000004404 heteroalkyl group Chemical group 0.000 description 3
• 239000012456 homogeneous solution Substances 0.000 description 3
• 239000005457 ice water Substances 0.000 description 3
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
• 238000002955 isolation Methods 0.000 description 3
• 125000000842 isoxazolyl group Chemical group 0.000 description 3
• 208000017169 kidney disease Diseases 0.000 description 3
• 239000007937 lozenge Substances 0.000 description 3
• YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 3
• 208000015122 neurodegenerative disease Diseases 0.000 description 3
• 108010003099 nodulin Proteins 0.000 description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 description 3
• 239000001301 oxygen Substances 0.000 description 3
• 239000006187 pill Substances 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 125000003373 pyrazinyl group Chemical group 0.000 description 3
• 125000003226 pyrazolyl group Chemical group 0.000 description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
• 125000005493 quinolyl group Chemical group 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 150000003384 small molecules Chemical class 0.000 description 3
• KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 3
• 210000000130 stem cell Anatomy 0.000 description 3
• 210000002784 stomach Anatomy 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
• 235000020357 syrup Nutrition 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 238000012360 testing method Methods 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
• 239000003039 volatile agent Substances 0.000 description 3
• 239000000080 wetting agent Substances 0.000 description 3
• ZQJYTTPJYLKTTI-UHFFFAOYSA-M zinc;2h-pyridin-2-ide;bromide Chemical compound Br[Zn+].C1=CC=N[C-]=C1 ZQJYTTPJYLKTTI-UHFFFAOYSA-M 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• UBWXUGDQUBIEIZ-UHFFFAOYSA-N (13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl) 3-phenylpropanoate Chemical compound CC12CCC(C3CCC(=O)C=C3CC3)C3C1CCC2OC(=O)CCC1=CC=CC=C1 UBWXUGDQUBIEIZ-UHFFFAOYSA-N 0.000 description 2
• ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
• UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
• YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
• WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-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
• UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
• OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 2
• MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
• YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 2
• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 2
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
• IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
• DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-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
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 2
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
• FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 2
• VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 2
• QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 2
• PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
• FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 2
• PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 2
• VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 2
• AIEATTRZKVGMBO-UHFFFAOYSA-N 2-bromo-4-fluoropyridine Chemical compound FC1=CC=NC(Br)=C1 AIEATTRZKVGMBO-UHFFFAOYSA-N 0.000 description 2
• TYOSQEKDQKYBLX-UHFFFAOYSA-N 2-bromo-6-ethylpyridine Chemical compound CCC1=CC=CC(Br)=N1 TYOSQEKDQKYBLX-UHFFFAOYSA-N 0.000 description 2
• ZIDIKYIZXMYHAW-UHFFFAOYSA-N 2-bromo-6-fluoropyridine Chemical compound FC1=CC=CC(Br)=N1 ZIDIKYIZXMYHAW-UHFFFAOYSA-N 0.000 description 2
• IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
• LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 2
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
• QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 2
• WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 2
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
• UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 2
• ZMUYXIARCDSXIP-UHFFFAOYSA-N 4-(2-chloropyridin-3-yl)quinoline Chemical compound ClC1=NC=CC=C1C1=CC=NC2=CC=CC=C12 ZMUYXIARCDSXIP-UHFFFAOYSA-N 0.000 description 2
• BLBDTBCGPHPIJK-UHFFFAOYSA-N 4-Amino-2-chloropyridine Chemical compound NC1=CC=NC(Cl)=C1 BLBDTBCGPHPIJK-UHFFFAOYSA-N 0.000 description 2
• UIADWSXPNFQQCZ-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenyl)-5-phenyl-1,3-oxazol-2-yl]butanoic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(OC=1C1=CC=CC=C1)CCCC(=O)O UIADWSXPNFQQCZ-UHFFFAOYSA-N 0.000 description 2
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 2
• GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 description 2
• XNAFDRAIDDXATH-UHFFFAOYSA-N 4-fluoropyridine Chemical compound FC1=C[C]=NC=C1 XNAFDRAIDDXATH-UHFFFAOYSA-N 0.000 description 2
• AEZROPWGTRMEKL-UHFFFAOYSA-N 4-methoxy-6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrido[3,2-d]pyrimidine Chemical compound COC=1C2=C(N=CN=1)C=CC(=N2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C AEZROPWGTRMEKL-UHFFFAOYSA-N 0.000 description 2
• DZJRFXMKJLTMAB-UHFFFAOYSA-N 5-(2-chloropyridin-3-yl)-1h-indazole Chemical compound ClC1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 DZJRFXMKJLTMAB-UHFFFAOYSA-N 0.000 description 2
• YEIBAOLXVWAPOS-UHFFFAOYSA-N 5-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)O)(F)F YEIBAOLXVWAPOS-UHFFFAOYSA-N 0.000 description 2
• VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 2
• ISKBXMMELYRESC-UHFFFAOYSA-N 5-bromo-6-chloropyridin-3-amine Chemical compound NC1=CN=C(Cl)C(Br)=C1 ISKBXMMELYRESC-UHFFFAOYSA-N 0.000 description 2
• XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 2
• VHGGWLBXAAHMCY-UHFFFAOYSA-N 6-(2-pyridin-2-ylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound N1=C(C(=CC=C1)C=1C=CC=2N(C=1)C(=CN=2)C#N)C1=NC=CC=C1 VHGGWLBXAAHMCY-UHFFFAOYSA-N 0.000 description 2
• FNBFSOZBVWJNPB-UHFFFAOYSA-N 6-(2-pyridin-2-ylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1=C(C(=CC=C1)C=1C=CC=2N(C=1)C(=CN=2)C(=O)N)C1=NC=CC=C1 FNBFSOZBVWJNPB-UHFFFAOYSA-N 0.000 description 2
• RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
• KXEWGWPRQSUZMJ-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-3H-pyrido[3,2-d]pyrimidin-4-one hydrochloride Chemical compound Cl.Cc1cccc(n1)-c1ncccc1-c1ccc2[nH]cnc(=O)c2n1 KXEWGWPRQSUZMJ-UHFFFAOYSA-N 0.000 description 2
• JLVQFBHNJXRJTL-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]quinoxaline Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2N=CC=NC2=CC=1 JLVQFBHNJXRJTL-UHFFFAOYSA-N 0.000 description 2
• KHANTGZDTRDFNQ-UHFFFAOYSA-N 6-[2-(6-propan-2-ylpyridin-2-yl)pyridin-3-yl]quinazolin-4-amine Chemical compound C(C)(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2C(=NC=NC2=CC=1)N KHANTGZDTRDFNQ-UHFFFAOYSA-N 0.000 description 2
• PNRLXHVPYLGZKU-UHFFFAOYSA-N 6-[5-amino-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound NC=1C=C(C(=NC=1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C(=O)O PNRLXHVPYLGZKU-UHFFFAOYSA-N 0.000 description 2
• MSPZFXKELDKRLD-UHFFFAOYSA-N 6-[6-methyl-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound CC1=CC=C(C(=N1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C#N MSPZFXKELDKRLD-UHFFFAOYSA-N 0.000 description 2
• GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 2
• WFOOPRMCWIUPKS-UHFFFAOYSA-N 7-(2-chloropyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound ClC1=NC=CC=C1C1=CC2=NC=NN2C=C1 WFOOPRMCWIUPKS-UHFFFAOYSA-N 0.000 description 2
• IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 2
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
• 102100034134 Activin receptor type-1B Human genes 0.000 description 2
• 102000005606 Activins Human genes 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• 241000416162 Astragalus gummifer Species 0.000 description 2
• 239000012664 BCL-2-inhibitor Substances 0.000 description 2
• 229940123711 Bcl2 inhibitor Drugs 0.000 description 2
• 206010065687 Bone loss Diseases 0.000 description 2
• UIDOBGOJLVDHRJ-UHFFFAOYSA-N BrC1=CC=C(C(=N1)C(F)F)F Chemical compound BrC1=CC=C(C(=N1)C(F)F)F UIDOBGOJLVDHRJ-UHFFFAOYSA-N 0.000 description 2
• 206010006187 Breast cancer Diseases 0.000 description 2
• 208000026310 Breast neoplasm Diseases 0.000 description 2
• JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 2
• GJNLNUWPEQQQQB-UHFFFAOYSA-N C1C=CC=C2C1=NC3=CC=CC(=C23)C4=C(N=CC=C4)Cl Chemical compound C1C=CC=C2C1=NC3=CC=CC(=C23)C4=C(N=CC=C4)Cl GJNLNUWPEQQQQB-UHFFFAOYSA-N 0.000 description 2
• BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 2
• 229910052684 Cerium Inorganic materials 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 229940126657 Compound 17 Drugs 0.000 description 2
• 229940126639 Compound 33 Drugs 0.000 description 2
• 229940127007 Compound 39 Drugs 0.000 description 2
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
• 108010092160 Dactinomycin Proteins 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
• 241000283073 Equus caballus Species 0.000 description 2
• 241000282326 Felis catus Species 0.000 description 2
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 101001059984 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 4 Proteins 0.000 description 2
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
• 240000007472 Leucaena leucocephala Species 0.000 description 2
• GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 2
• 208000001145 Metabolic Syndrome Diseases 0.000 description 2
• 208000029725 Metabolic bone disease Diseases 0.000 description 2
• 102100028194 Mitogen-activated protein kinase kinase kinase kinase 4 Human genes 0.000 description 2
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
• QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
• POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 2
• QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• 239000005642 Oleic acid Substances 0.000 description 2
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
• 241000283973 Oryctolagus cuniculus Species 0.000 description 2
• 101150003085 Pdcl gene Proteins 0.000 description 2
• 235000019483 Peanut oil Nutrition 0.000 description 2
• 241001494479 Pecora Species 0.000 description 2
• 241000288906 Primates Species 0.000 description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
• 241000700159 Rattus Species 0.000 description 2
• 241000283984 Rodentia Species 0.000 description 2
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• 235000021355 Stearic acid Nutrition 0.000 description 2
• 208000005718 Stomach Neoplasms Diseases 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 241000282898 Sus scrofa Species 0.000 description 2
• 102100033456 TGF-beta receptor type-1 Human genes 0.000 description 2
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
• CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 description 2
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
• 229920001615 Tragacanth Polymers 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 2
• SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 2
• SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 2
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical class C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 2
• 239000011149 active material Substances 0.000 description 2
• 108010023082 activin A Proteins 0.000 description 2
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
• 210000001789 adipocyte Anatomy 0.000 description 2
• QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
• 125000000539 amino acid group Chemical group 0.000 description 2
• 125000003277 amino group Chemical group 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
• 235000010323 ascorbic acid Nutrition 0.000 description 2
• 239000011668 ascorbic acid Substances 0.000 description 2
• 229960005070 ascorbic acid Drugs 0.000 description 2
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
• 125000002393 azetidinyl group Chemical group 0.000 description 2
• 230000009286 beneficial effect Effects 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
• 230000031018 biological processes and functions Effects 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 description 2
• 239000001506 calcium phosphate Substances 0.000 description 2
• 229910000389 calcium phosphate Inorganic materials 0.000 description 2
• 235000011010 calcium phosphates Nutrition 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 125000002837 carbocyclic group Chemical group 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 2
• 229960000541 cetyl alcohol Drugs 0.000 description 2
• 238000012512 characterization method Methods 0.000 description 2
• 208000020832 chronic kidney disease Diseases 0.000 description 2
• 208000019425 cirrhosis of liver Diseases 0.000 description 2
• 235000015165 citric acid Nutrition 0.000 description 2
• 238000003776 cleavage reaction Methods 0.000 description 2
• 229940125797 compound 12 Drugs 0.000 description 2
• 229940126543 compound 14 Drugs 0.000 description 2
• 229940125782 compound 2 Drugs 0.000 description 2
• 229940125810 compound 20 Drugs 0.000 description 2
• 229940126208 compound 22 Drugs 0.000 description 2
• 229940125833 compound 23 Drugs 0.000 description 2
• 229940125961 compound 24 Drugs 0.000 description 2
• 229940125846 compound 25 Drugs 0.000 description 2
• 229940127204 compound 29 Drugs 0.000 description 2
• 229940126214 compound 3 Drugs 0.000 description 2
• 229940125877 compound 31 Drugs 0.000 description 2
• 229940125878 compound 36 Drugs 0.000 description 2
• 229940125807 compound 37 Drugs 0.000 description 2
• 229940127573 compound 38 Drugs 0.000 description 2
• 229940125936 compound 42 Drugs 0.000 description 2
• 229940125844 compound 46 Drugs 0.000 description 2
• 229940127271 compound 49 Drugs 0.000 description 2
• 229940125898 compound 5 Drugs 0.000 description 2
• 229940126545 compound 53 Drugs 0.000 description 2
• 229940127113 compound 57 Drugs 0.000 description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
• 230000010250 cytokine signaling pathway Effects 0.000 description 2
• 229960000640 dactinomycin Drugs 0.000 description 2
• 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 2
• 229910052805 deuterium Inorganic materials 0.000 description 2
• JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
• 239000013024 dilution buffer Substances 0.000 description 2
• 239000000539 dimer Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
• 231100000673 dose–response relationship Toxicity 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 239000012055 enteric layer Substances 0.000 description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
• GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 2
• 230000003176 fibrotic effect Effects 0.000 description 2
• 238000003818 flash chromatography Methods 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 229960002949 fluorouracil Drugs 0.000 description 2
• 239000013022 formulation composition Substances 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 206010017758 gastric cancer Diseases 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 239000007903 gelatin capsule Substances 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 229960005277 gemcitabine Drugs 0.000 description 2
• 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 2
• 239000008103 glucose Substances 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 2
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 2
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
• 239000000710 homodimer Substances 0.000 description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
• 229940071870 hydroiodic acid Drugs 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• 125000001041 indolyl group Chemical group 0.000 description 2
• 238000001802 infusion Methods 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
• 125000001786 isothiazolyl group Chemical group 0.000 description 2
• 230000000155 isotopic effect Effects 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000000787 lecithin Substances 0.000 description 2
• 235000010445 lecithin Nutrition 0.000 description 2
• 229940067606 lecithin Drugs 0.000 description 2
• 208000032839 leukemia Diseases 0.000 description 2
• 229940057995 liquid paraffin Drugs 0.000 description 2
• 229960002247 lomustine Drugs 0.000 description 2
• 239000006166 lysate Substances 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 239000011976 maleic acid Substances 0.000 description 2
• 230000000873 masking effect Effects 0.000 description 2
• 229960001924 melphalan Drugs 0.000 description 2
• 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 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• 239000002480 mineral oil Substances 0.000 description 2
• 235000010446 mineral oil Nutrition 0.000 description 2
• 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• 230000001002 morphogenetic effect Effects 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• YCJZWBZJSYLMPB-UHFFFAOYSA-N n-(2-chloropyrimidin-4-yl)-2,5-dimethyl-1-phenylimidazole-4-carboxamide Chemical compound CC=1N(C=2C=CC=CC=2)C(C)=NC=1C(=O)NC1=CC=NC(Cl)=N1 YCJZWBZJSYLMPB-UHFFFAOYSA-N 0.000 description 2
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 2
• 235000001968 nicotinic acid Nutrition 0.000 description 2
• 239000011664 nicotinic acid Substances 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 239000012299 nitrogen atmosphere Substances 0.000 description 2
• BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
• 239000000346 nonvolatile oil Substances 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
• 239000004006 olive oil Substances 0.000 description 2
• 235000008390 olive oil Nutrition 0.000 description 2
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 2
• PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
• 239000000312 peanut oil Substances 0.000 description 2
• 239000008177 pharmaceutical agent Substances 0.000 description 2
• 229940124531 pharmaceutical excipient Drugs 0.000 description 2
• 150000003904 phospholipids Chemical class 0.000 description 2
• 125000004193 piperazinyl group Chemical group 0.000 description 2
• 125000003386 piperidinyl group Chemical group 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
• 229920000053 polysorbate 80 Polymers 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 239000002243 precursor Substances 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
• 208000005069 pulmonary fibrosis Diseases 0.000 description 2
• 208000002815 pulmonary hypertension Diseases 0.000 description 2
• DMYLUKNFEYWGCH-UHFFFAOYSA-N pyridazine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=N1 DMYLUKNFEYWGCH-UHFFFAOYSA-N 0.000 description 2
• BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-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
• 230000026267 regulation of growth Effects 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 230000002441 reversible effect Effects 0.000 description 2
• 125000006413 ring segment Chemical group 0.000 description 2
• 229960004641 rituximab Drugs 0.000 description 2
• 229910052707 ruthenium Inorganic materials 0.000 description 2
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
• 229940081974 saccharin Drugs 0.000 description 2
• 235000019204 saccharin Nutrition 0.000 description 2
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 230000007017 scission Effects 0.000 description 2
• 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 2
• 229960002930 sirolimus Drugs 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 239000008117 stearic acid Substances 0.000 description 2
• 201000011549 stomach cancer Diseases 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 239000011975 tartaric acid Substances 0.000 description 2
• 235000002906 tartaric acid Nutrition 0.000 description 2
• 229960000235 temsirolimus Drugs 0.000 description 2
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
• GTNJYSHYBCIFTF-UHFFFAOYSA-N tert-butyl 5-bromo-1h-indazole-3-carboxylate Chemical compound C1=C(Br)C=C2C(C(=O)OC(C)(C)C)=NNC2=C1 GTNJYSHYBCIFTF-UHFFFAOYSA-N 0.000 description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
• 235000010487 tragacanth Nutrition 0.000 description 2
• 239000000196 tragacanth Substances 0.000 description 2
• 229940116362 tragacanth Drugs 0.000 description 2
• REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 2
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
• 238000004704 ultra performance liquid chromatography Methods 0.000 description 2
• 229950005972 urelumab Drugs 0.000 description 2
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
• 235000015112 vegetable and seed oil Nutrition 0.000 description 2
• 239000008158 vegetable oil Substances 0.000 description 2
• 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 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
• BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
• 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 1
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
• KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 description 1
• HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
• CDKIEBFIMCSCBB-UHFFFAOYSA-N 1-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-3-(1-methyl-2-phenylpyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one;hydrochloride Chemical compound Cl.C1C=2C=C(OC)C(OC)=CC=2CCN1C(=O)C=CC(C1=CC=CN=C1N1C)=C1C1=CC=CC=C1 CDKIEBFIMCSCBB-UHFFFAOYSA-N 0.000 description 1
• RUJTWTUYVOEEFW-UHFFFAOYSA-N 1-(6-bromopyridin-2-yl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=N1 RUJTWTUYVOEEFW-UHFFFAOYSA-N 0.000 description 1
• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
• MYZIJBJPIHILLG-UHFFFAOYSA-N 1-chloro-9h-fluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2Cl MYZIJBJPIHILLG-UHFFFAOYSA-N 0.000 description 1
• PDAXFOUMAUGMCQ-UHFFFAOYSA-N 1-ethoxyhexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCC(O)OCC PDAXFOUMAUGMCQ-UHFFFAOYSA-N 0.000 description 1
• SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• KKVYYGGCHJGEFJ-UHFFFAOYSA-N 1-n-(4-chlorophenyl)-6-methyl-5-n-[3-(7h-purin-6-yl)pyridin-2-yl]isoquinoline-1,5-diamine Chemical compound N=1C=CC2=C(NC=3C(=CC=CN=3)C=3C=4N=CNC=4N=CN=3)C(C)=CC=C2C=1NC1=CC=C(Cl)C=C1 KKVYYGGCHJGEFJ-UHFFFAOYSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• OARGFWQSVACNCO-UHFFFAOYSA-N 1-oxidoquinoxalin-1-ium Chemical compound C1=CC=C2[N+]([O-])=CC=NC2=C1 OARGFWQSVACNCO-UHFFFAOYSA-N 0.000 description 1
• FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
• PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• FSKYZRCACCHDGR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-4-one Chemical compound C1=CN=C2C(=O)N=CNC2=C1 FSKYZRCACCHDGR-UHFFFAOYSA-N 0.000 description 1
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
• KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 1
• WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
• UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
• IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
• IRTOCXBLUOPRFT-UHFFFAOYSA-N 2-bromo-4,6-dimethylpyridine Chemical compound CC1=CC(C)=NC(Br)=C1 IRTOCXBLUOPRFT-UHFFFAOYSA-N 0.000 description 1
• YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical compound CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 1
• SOHDPICLICFSOP-UHFFFAOYSA-N 2-bromo-6-methylpyridine Chemical compound CC1=CC=CC(Br)=N1 SOHDPICLICFSOP-UHFFFAOYSA-N 0.000 description 1
• WEMPEMXDSUATEK-UHFFFAOYSA-N 2-bromo-6-phenylmethoxypyridine Chemical compound BrC1=CC=CC(OCC=2C=CC=CC=2)=N1 WEMPEMXDSUATEK-UHFFFAOYSA-N 0.000 description 1
• PMTPFBWHUOWTNN-UHFFFAOYSA-N 2-chloro-4-methoxypyridine Chemical compound COC1=CC=NC(Cl)=C1 PMTPFBWHUOWTNN-UHFFFAOYSA-N 0.000 description 1
• RVHOBHMAPRVOLO-UHFFFAOYSA-N 2-ethylbutanedioic acid Chemical compound CCC(C(O)=O)CC(O)=O RVHOBHMAPRVOLO-UHFFFAOYSA-N 0.000 description 1
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
• QBWKSTKKUCFZCL-UHFFFAOYSA-N 2-methyl-6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC=1N=C2N(C=C(C=C2)C=2C(=NC=CC=2)C2=NC(=CC=C2)C)C=1C(=O)N QBWKSTKKUCFZCL-UHFFFAOYSA-N 0.000 description 1
• CTRPRMNBTVRDFH-UHFFFAOYSA-N 2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CNC1=NC(N)=NC(N)=N1 CTRPRMNBTVRDFH-UHFFFAOYSA-N 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 1
• VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 1
• XVTAQSGZOGYIEY-UHFFFAOYSA-N 3,4-dihydroisocoumarin Chemical compound C1=CC=C2C(=O)OCCC2=C1 XVTAQSGZOGYIEY-UHFFFAOYSA-N 0.000 description 1
• CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
• HDBQZGJWHMCXIL-UHFFFAOYSA-N 3,7-dihydropurine-2-thione Chemical compound SC1=NC=C2NC=NC2=N1 HDBQZGJWHMCXIL-UHFFFAOYSA-N 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
• CBDQVZVCRLQAOD-UHFFFAOYSA-N 3-bromo-2-chloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(Cl)=C1Br CBDQVZVCRLQAOD-UHFFFAOYSA-N 0.000 description 1
• UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
• 125000006041 3-hexenyl group Chemical group 0.000 description 1
• FCNJEINFWXOLQY-UHFFFAOYSA-N 4,6-dichloropyrido[3,2-d]pyrimidine Chemical compound N1=CN=C(Cl)C2=NC(Cl)=CC=C21 FCNJEINFWXOLQY-UHFFFAOYSA-N 0.000 description 1
• RXGPUHMQDJHDPW-UHFFFAOYSA-N 4-(2-chloropyridin-3-yl)-1H-quinolin-2-one Chemical compound ClC1=NC=CC=C1C1=CC(NC2=CC=CC=C12)=O RXGPUHMQDJHDPW-UHFFFAOYSA-N 0.000 description 1
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
• XXJWYDDUDKYVKI-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 XXJWYDDUDKYVKI-UHFFFAOYSA-N 0.000 description 1
• IXRKKRSAYDICNA-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-1H-quinolin-2-one Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=CC(NC2=CC=CC=C12)=O IXRKKRSAYDICNA-UHFFFAOYSA-N 0.000 description 1
• PTPTZLXZHPPVKG-UHFFFAOYSA-N 4-bromo-2-fluoropyridine Chemical compound FC1=CC(Br)=CC=N1 PTPTZLXZHPPVKG-UHFFFAOYSA-N 0.000 description 1
• MOCRCEBISJMOGG-UHFFFAOYSA-N 4-bromo-3-fluoro-2-methylpyridine Chemical compound BrC1=C(C(=NC=C1)C)F MOCRCEBISJMOGG-UHFFFAOYSA-N 0.000 description 1
• GYUAOSJIGMDMNJ-UHFFFAOYSA-N 4-bromo-3-methylpyridine Chemical compound CC1=CN=CC=C1Br GYUAOSJIGMDMNJ-UHFFFAOYSA-N 0.000 description 1
• SUXIPCHEUMEUSV-UHFFFAOYSA-N 4-bromoquinoline Chemical compound C1=CC=C2C(Br)=CC=NC2=C1 SUXIPCHEUMEUSV-UHFFFAOYSA-N 0.000 description 1
• BEENLLJNAIVCCL-UHFFFAOYSA-N 4-chloro-6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrido[3,2-d]pyrimidine Chemical compound ClC=1C2=C(N=CN=1)C=CC(=N2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C BEENLLJNAIVCCL-UHFFFAOYSA-N 0.000 description 1
• RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
• VOPNAHNLWOLODK-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;phenylmethanesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.OS(=O)(=O)CC1=CC=CC=C1 VOPNAHNLWOLODK-UHFFFAOYSA-N 0.000 description 1
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
• FRGXNJWEDDQLFH-UHFFFAOYSA-N 4-propan-2-ylpyridine Chemical compound CC(C)C1=CC=NC=C1 FRGXNJWEDDQLFH-UHFFFAOYSA-N 0.000 description 1
• OPOSZCCQNDXOBP-UHFFFAOYSA-N 5-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]-N-(oxetan-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)NC1COC1 OPOSZCCQNDXOBP-UHFFFAOYSA-N 0.000 description 1
• AZFAJDPMNWNYRF-UHFFFAOYSA-N 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-1h-indazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=N1 AZFAJDPMNWNYRF-UHFFFAOYSA-N 0.000 description 1
• HKNCTBCYPOKHHS-UHFFFAOYSA-N 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)N HKNCTBCYPOKHHS-UHFFFAOYSA-N 0.000 description 1
• WDIWOWWQGBVXOA-UHFFFAOYSA-N 5-[2-[6-(difluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)O)F WDIWOWWQGBVXOA-UHFFFAOYSA-N 0.000 description 1
• QPCXCVCWVDKSNY-UHFFFAOYSA-N 5-bromo-1H-carbazole Chemical compound BrC1=C2C3=CC=CCC3=NC2=CC=C1 QPCXCVCWVDKSNY-UHFFFAOYSA-N 0.000 description 1
• STVHMYNPQCLUNJ-UHFFFAOYSA-N 5-bromo-1h-indazole Chemical compound BrC1=CC=C2NN=CC2=C1 STVHMYNPQCLUNJ-UHFFFAOYSA-N 0.000 description 1
• ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
• CHAVAGQWWVQXQJ-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound ClC1=NC(=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)C CHAVAGQWWVQXQJ-UHFFFAOYSA-N 0.000 description 1
• PUOAIUQPZPXAKC-UHFFFAOYSA-N 6-(2-chloropyridin-3-yl)pyrido[3,2-d]pyrimidin-4-amine Chemical compound ClC1=NC=CC=C1C=1C=CC=2N=CN=C(C=2N=1)N PUOAIUQPZPXAKC-UHFFFAOYSA-N 0.000 description 1
• CGRFIXQPFPDSHI-UHFFFAOYSA-N 6-(2-chloropyridin-3-yl)quinazolin-4-amine Chemical compound ClC1=NC=CC=C1C=1C=C2C(=NC=NC2=CC=1)N CGRFIXQPFPDSHI-UHFFFAOYSA-N 0.000 description 1
• RYBZXNLZNBCOHO-UHFFFAOYSA-N 6-(2-chloropyridin-3-yl)quinoxaline Chemical compound ClC1=NC=CC=C1C1=CC=C(N=CC=N2)C2=C1 RYBZXNLZNBCOHO-UHFFFAOYSA-N 0.000 description 1
• RMHXAAARAOIMIT-UHFFFAOYSA-N 6-(2-pyridin-2-ylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N1=C(C(=CC=C1)C=1C=CC=2N(C=1)N=CN=2)C1=NC=CC=C1 RMHXAAARAOIMIT-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
• HJSBGWUOAXOQJX-UHFFFAOYSA-N 6-[2-(4,6-dimethylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC(=NC(=C1)C)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N HJSBGWUOAXOQJX-UHFFFAOYSA-N 0.000 description 1
• CZPUNBHOFCWYIE-UHFFFAOYSA-N 6-[2-(4-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N CZPUNBHOFCWYIE-UHFFFAOYSA-N 0.000 description 1
• BGBHTSCOHQVULI-UHFFFAOYSA-N 6-[2-(4-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N BGBHTSCOHQVULI-UHFFFAOYSA-N 0.000 description 1
• GTAUYLFXXWWULC-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-2-carboxamide Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)C(=O)N GTAUYLFXXWWULC-UHFFFAOYSA-N 0.000 description 1
• GAMFQISAYKUQHQ-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N GAMFQISAYKUQHQ-UHFFFAOYSA-N 0.000 description 1
• XVBKGEJGVAOOOM-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]pyrido[3,2-d]pyrimidin-4-amine Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=CC=2N=CN=C(C=2N=1)N XVBKGEJGVAOOOM-UHFFFAOYSA-N 0.000 description 1
• WXWZYJQUMVBFPH-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]quinazolin-4-amine Chemical compound CC1=C(F)C=CC(=N1)C1=NC=CC=C1C1=CC2=C(C=C1)N=CN=C2N WXWZYJQUMVBFPH-UHFFFAOYSA-N 0.000 description 1
• QJVYVPBFPPDGEP-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]quinoxaline Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=C2N=CC=NC2=CC=1 QJVYVPBFPPDGEP-UHFFFAOYSA-N 0.000 description 1
• FPVRMHCAYQMFQU-UHFFFAOYSA-N 6-[2-(5-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC=1C=CC(=NC=1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N FPVRMHCAYQMFQU-UHFFFAOYSA-N 0.000 description 1
• CQWCBSZWDFCRPI-UHFFFAOYSA-N 6-[2-(5-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound FC=1C=CC(=NC=1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N CQWCBSZWDFCRPI-UHFFFAOYSA-N 0.000 description 1
• ITYLODYDBTVSQE-UHFFFAOYSA-N 6-[2-(5-fluoropyridin-2-yl)pyridin-3-yl]pyrido[3,2-d]pyrimidin-4-amine Chemical compound FC=1C=CC(=NC=1)C1=NC=CC=C1C=1C=CC=2N=CN=C(C=2N=1)N ITYLODYDBTVSQE-UHFFFAOYSA-N 0.000 description 1
• HNHOOWUAJZGFKM-UHFFFAOYSA-N 6-[2-(6-chloropyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound ClC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N HNHOOWUAJZGFKM-UHFFFAOYSA-N 0.000 description 1
• SQRDZIYOMSMQCQ-UHFFFAOYSA-N 6-[2-(6-cyclopropylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1(CC1)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N SQRDZIYOMSMQCQ-UHFFFAOYSA-N 0.000 description 1
• PLOZBMIFSPZBGR-UHFFFAOYSA-N 6-[2-(6-cyclopropylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1(CC1)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N PLOZBMIFSPZBGR-UHFFFAOYSA-N 0.000 description 1
• GPLZWPMCSPAMIE-UHFFFAOYSA-N 6-[2-(6-cyclopropylpyridin-2-yl)pyridin-3-yl]pyrido[3,2-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N=CN=C(C=2N=1)N GPLZWPMCSPAMIE-UHFFFAOYSA-N 0.000 description 1
• BUUAALLSZRZRDH-UHFFFAOYSA-N 6-[2-(6-ethylpyridin-2-yl)pyridin-3-yl]quinazolin-4-amine Chemical compound C(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2C(=NC=NC2=CC=1)N BUUAALLSZRZRDH-UHFFFAOYSA-N 0.000 description 1
• YCTLDUVPFOJWML-UHFFFAOYSA-N 6-[2-(6-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N YCTLDUVPFOJWML-UHFFFAOYSA-N 0.000 description 1
• PDLOIKWMTHAUIQ-UHFFFAOYSA-N 6-[2-(6-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N PDLOIKWMTHAUIQ-UHFFFAOYSA-N 0.000 description 1
• HKCBAKPETUOBIQ-UHFFFAOYSA-N 6-[2-(6-fluoropyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N HKCBAKPETUOBIQ-UHFFFAOYSA-N 0.000 description 1
• RUNNKSXKWNXOAY-UHFFFAOYSA-N 6-[2-(6-fluoropyridin-2-yl)pyridin-3-yl]quinazolin-4-amine Chemical compound FC1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2C(=NC=NC2=CC=1)N RUNNKSXKWNXOAY-UHFFFAOYSA-N 0.000 description 1
• FFMBLMKLOOJUDW-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)-6-(trifluoromethyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound CC1=CC=CC(=N1)C1=NC(=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)C(F)(F)F FFMBLMKLOOJUDW-UHFFFAOYSA-N 0.000 description 1
• YAANUPWQSUVVRF-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-2-carboxamide Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)C(=O)N YAANUPWQSUVVRF-UHFFFAOYSA-N 0.000 description 1
• QQFLQHVUKANAAG-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)O QQFLQHVUKANAAG-UHFFFAOYSA-N 0.000 description 1
• CBDGDYMIVDQRMA-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carboxylic acid Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)O CBDGDYMIVDQRMA-UHFFFAOYSA-N 0.000 description 1
• LBWMWCOTROJRHX-UHFFFAOYSA-N 6-[2-(6-propan-2-ylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C(C)(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N LBWMWCOTROJRHX-UHFFFAOYSA-N 0.000 description 1
• LXHXQQKOOGGSPE-UHFFFAOYSA-N 6-[2-(6-propan-2-ylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C(C)(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N LXHXQQKOOGGSPE-UHFFFAOYSA-N 0.000 description 1
• HEADPVLOZICIIU-UHFFFAOYSA-N 6-[2-(6-propan-2-ylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C(C)(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N HEADPVLOZICIIU-UHFFFAOYSA-N 0.000 description 1
• HOOPMLRDDAPJFG-UHFFFAOYSA-N 6-[2-(6-propan-2-ylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound C(C)(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N HOOPMLRDDAPJFG-UHFFFAOYSA-N 0.000 description 1
• XTHRTJZJMVTMBP-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)-5-fluoropyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound FC(C1=C(C=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C=CN=2)F)F XTHRTJZJMVTMBP-UHFFFAOYSA-N 0.000 description 1
• UEZOTQITRBOACI-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)-5-fluoropyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC(C1=C(C=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)F)F UEZOTQITRBOACI-UHFFFAOYSA-N 0.000 description 1
• MYODWXWMABYIDR-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)pyridin-2-yl]-5-fluoropyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC(C1=CC=CC(=N1)C1=NC=C(C=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)F)F MYODWXWMABYIDR-UHFFFAOYSA-N 0.000 description 1
• YKRXQSOZJKVUAG-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)pyridin-2-yl]-5-fluoropyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NC=C(C=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N)F)F YKRXQSOZJKVUAG-UHFFFAOYSA-N 0.000 description 1
• RMQUGDMQZURTHV-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)F RMQUGDMQZURTHV-UHFFFAOYSA-N 0.000 description 1
• KRPVXXDLIIJKSE-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N)F KRPVXXDLIIJKSE-UHFFFAOYSA-N 0.000 description 1
• YWYJPKWUKLAPJF-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)F YWYJPKWUKLAPJF-UHFFFAOYSA-N 0.000 description 1
• DBWHTIBDVVUYEM-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrido[3,2-d]pyrimidin-4-amine Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N=CN=C(C=2N=1)N)F DBWHTIBDVVUYEM-UHFFFAOYSA-N 0.000 description 1
• VOZYQUZWOHRZRX-UHFFFAOYSA-N 6-[2-[6-(difluoromethyl)pyridin-2-yl]pyridin-3-yl]quinazolin-4-amine Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2C(=NC=NC2=CC=1)N)F VOZYQUZWOHRZRX-UHFFFAOYSA-N 0.000 description 1
• UDYJICCXTYHZST-UHFFFAOYSA-N 6-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine-2-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)C(=O)N)(F)F UDYJICCXTYHZST-UHFFFAOYSA-N 0.000 description 1
• DZHODFRRHHTDML-UHFFFAOYSA-N 6-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)(F)F DZHODFRRHHTDML-UHFFFAOYSA-N 0.000 description 1
• RHNTUJVVSYIKDD-UHFFFAOYSA-N 6-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N)(F)F RHNTUJVVSYIKDD-UHFFFAOYSA-N 0.000 description 1
• MQNBKVRVTGHUOO-UHFFFAOYSA-N 6-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]quinoxaline Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2N=CC=NC2=CC=1)(F)F MQNBKVRVTGHUOO-UHFFFAOYSA-N 0.000 description 1
• RSZIJRFZWKINKF-UHFFFAOYSA-N 6-[4-(hydroxymethyl)-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound OCC1=C(C(=NC=C1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C#N RSZIJRFZWKINKF-UHFFFAOYSA-N 0.000 description 1
• YZKQBBUNVBRNLC-UHFFFAOYSA-N 6-[4-amino-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound NC1=C(C(=NC=C1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C(=O)N YZKQBBUNVBRNLC-UHFFFAOYSA-N 0.000 description 1
• IRDIFSAZOXFGSK-UHFFFAOYSA-N 6-[5-amino-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound NC=1C=C(C(=NC=1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C(=O)N IRDIFSAZOXFGSK-UHFFFAOYSA-N 0.000 description 1
• YNEYPWVDECTXGL-UHFFFAOYSA-N 6-[5-fluoro-2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC=1C=C(C(=NC=1)C1=NC(=C(C=C1)F)C)C=1C=CC=2N(C=1)C(=CN=2)C(=O)N YNEYPWVDECTXGL-UHFFFAOYSA-N 0.000 description 1
• CLWHNLGCPYGPJJ-UHFFFAOYSA-N 6-[5-fluoro-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC=1C=C(C(=NC=1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C#N CLWHNLGCPYGPJJ-UHFFFAOYSA-N 0.000 description 1
• CQLQGUXSQXPNBF-UHFFFAOYSA-N 6-[5-fluoro-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC=1C=C(C(=NC=1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C(=O)N CQLQGUXSQXPNBF-UHFFFAOYSA-N 0.000 description 1
• CXRXKDSDRWLKTK-UHFFFAOYSA-N 6-bromo-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(Br)C=CC2=NC=NN21 CXRXKDSDRWLKTK-UHFFFAOYSA-N 0.000 description 1
• VUNSVSBURVCQKV-UHFFFAOYSA-N 6-chloro-4-methoxypyrido[3,2-d]pyrimidine Chemical compound C1=C(Cl)N=C2C(OC)=NC=NC2=C1 VUNSVSBURVCQKV-UHFFFAOYSA-N 0.000 description 1
• OBYJTLDIQBWBHM-UHFFFAOYSA-N 6-chloropyridin-2-amine Chemical compound NC1=CC=CC(Cl)=N1 OBYJTLDIQBWBHM-UHFFFAOYSA-N 0.000 description 1
• 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 1
• NDKQYMPVBHCEOS-UHFFFAOYSA-N 7-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=CC=2N(C=C1)N=CN=2 NDKQYMPVBHCEOS-UHFFFAOYSA-N 0.000 description 1
• VGJYOOVSVQHZPL-UHFFFAOYSA-N 7-bromo-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(Br)C=CN2N=CN=C21 VGJYOOVSVQHZPL-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 102100034111 Activin receptor type-1 Human genes 0.000 description 1
• 101710173011 Activin receptor type-1B Proteins 0.000 description 1
• 102100034135 Activin receptor type-1C Human genes 0.000 description 1
• 102100021886 Activin receptor type-2A Human genes 0.000 description 1
• 102100027647 Activin receptor type-2B Human genes 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
• MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 1
• 229940125565 BMS-986016 Drugs 0.000 description 1
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 1
• 208000033222 Biliary cirrhosis primary Diseases 0.000 description 1
• 206010005003 Bladder cancer Diseases 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• 102000007350 Bone Morphogenetic Proteins Human genes 0.000 description 1
• 108010007726 Bone Morphogenetic Proteins Proteins 0.000 description 1
• 208000006386 Bone Resorption Diseases 0.000 description 1
• 102100025423 Bone morphogenetic protein receptor type-1A Human genes 0.000 description 1
• 102100027052 Bone morphogenetic protein receptor type-1B Human genes 0.000 description 1
• 102100025422 Bone morphogenetic protein receptor type-2 Human genes 0.000 description 1
• 208000003174 Brain Neoplasms Diseases 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• POXSQGDWTKWLQK-UHFFFAOYSA-N CC(CCCCCCCCCCCOCCl)(C)C Chemical compound CC(CCCCCCCCCCCOCCl)(C)C POXSQGDWTKWLQK-UHFFFAOYSA-N 0.000 description 1
• 102000008203 CTLA-4 Antigen Human genes 0.000 description 1
• 108010021064 CTLA-4 Antigen Proteins 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 1
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 206010007559 Cardiac failure congestive Diseases 0.000 description 1
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 239000004380 Cholic acid Substances 0.000 description 1
• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 1
• 102000008186 Collagen Human genes 0.000 description 1
• 108010035532 Collagen Proteins 0.000 description 1
• 206010048832 Colon adenoma Diseases 0.000 description 1
• 206010009944 Colon cancer Diseases 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 102000004420 Creatine Kinase Human genes 0.000 description 1
• 108010042126 Creatine kinase Proteins 0.000 description 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• 230000000970 DNA cross-linking effect Effects 0.000 description 1
• 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
• 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
• ZBNZXTGUTAYRHI-UHFFFAOYSA-N Dasatinib Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1Cl ZBNZXTGUTAYRHI-UHFFFAOYSA-N 0.000 description 1
• 102000009058 Death Domain Receptors Human genes 0.000 description 1
• 108010049207 Death Domain Receptors Proteins 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• 101710162371 Dihydroxy-acid dehydratase 1 Proteins 0.000 description 1
• 101710162370 Dihydroxy-acid dehydratase 2 Proteins 0.000 description 1
• 101710178850 Dolichyl-diphosphooligosaccharide-protein glycosyltransferase subunit DAD1 Proteins 0.000 description 1
• 102100039104 Dolichyl-diphosphooligosaccharide-protein glycosyltransferase subunit DAD1 Human genes 0.000 description 1
• 101710178846 Dolichyl-diphosphooligosaccharide-protein glycosyltransferase subunit DAD2 Proteins 0.000 description 1
• 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 description 1
• 201000009273 Endometriosis Diseases 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical group CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 102000001690 Factor VIII Human genes 0.000 description 1
• 108010054218 Factor VIII Proteins 0.000 description 1
• 102000016970 Follistatin Human genes 0.000 description 1
• 108010014612 Follistatin Proteins 0.000 description 1
• 102000019203 Follistatin-Related Proteins Human genes 0.000 description 1
• 108010012820 Follistatin-Related Proteins Proteins 0.000 description 1
• 230000005526 G1 to G0 transition Effects 0.000 description 1
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
• XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 description 1
• 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
• 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
• 108010009202 Growth Factor Receptors Proteins 0.000 description 1
• 102000009465 Growth Factor Receptors Human genes 0.000 description 1
• 102100040898 Growth/differentiation factor 11 Human genes 0.000 description 1
• 101710194452 Growth/differentiation factor 11 Proteins 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 208000031886 HIV Infections Diseases 0.000 description 1
• 208000037357 HIV infectious disease Diseases 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 208000018565 Hemochromatosis Diseases 0.000 description 1
• 208000005176 Hepatitis C Diseases 0.000 description 1
• 101000799140 Homo sapiens Activin receptor type-1 Proteins 0.000 description 1
• 101000799189 Homo sapiens Activin receptor type-1B Proteins 0.000 description 1
• 101000799193 Homo sapiens Activin receptor type-1C Proteins 0.000 description 1
• 101000970954 Homo sapiens Activin receptor type-2A Proteins 0.000 description 1
• 101000937269 Homo sapiens Activin receptor type-2B Proteins 0.000 description 1
• 101000934638 Homo sapiens Bone morphogenetic protein receptor type-1A Proteins 0.000 description 1
• 101000984546 Homo sapiens Bone morphogenetic protein receptor type-1B Proteins 0.000 description 1
• 101000934635 Homo sapiens Bone morphogenetic protein receptor type-2 Proteins 0.000 description 1
• 101000934338 Homo sapiens Myeloid cell surface antigen CD33 Proteins 0.000 description 1
• 101000799194 Homo sapiens Serine/threonine-protein kinase receptor R3 Proteins 0.000 description 1
• 101000712674 Homo sapiens TGF-beta receptor type-1 Proteins 0.000 description 1
• 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
• DOMWKUIIPQCAJU-LJHIYBGHSA-N Hydroxyprogesterone caproate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)CCCCC)[C@@]1(C)CC2 DOMWKUIIPQCAJU-LJHIYBGHSA-N 0.000 description 1
• 206010020850 Hyperthyroidism Diseases 0.000 description 1
• 206010020880 Hypertrophy Diseases 0.000 description 1
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 1
• 208000014919 IgG4-related retroperitoneal fibrosis Diseases 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
• 229940076838 Immune checkpoint inhibitor Drugs 0.000 description 1
• 102000002746 Inhibins Human genes 0.000 description 1
• 108010004250 Inhibins Proteins 0.000 description 1
• 102000006992 Interferon-alpha Human genes 0.000 description 1
• 108010047761 Interferon-alpha Proteins 0.000 description 1
• 102000008070 Interferon-gamma Human genes 0.000 description 1
• 108010074328 Interferon-gamma Proteins 0.000 description 1
• 102000000588 Interleukin-2 Human genes 0.000 description 1
• 108010002350 Interleukin-2 Proteins 0.000 description 1
• 208000002260 Keloid Diseases 0.000 description 1
• 206010023330 Keloid scar Diseases 0.000 description 1
• 208000008839 Kidney Neoplasms Diseases 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• 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 1
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
• 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
• 239000005551 L01XE03 - Erlotinib Substances 0.000 description 1
• 239000002147 L01XE04 - Sunitinib Substances 0.000 description 1
• 239000005511 L01XE05 - Sorafenib Substances 0.000 description 1
• 239000002067 L01XE06 - Dasatinib Substances 0.000 description 1
• 239000002136 L01XE07 - Lapatinib Substances 0.000 description 1
• 239000005536 L01XE08 - Nilotinib Substances 0.000 description 1
• 239000003798 L01XE11 - Pazopanib Substances 0.000 description 1
• 239000002118 L01XE12 - Vandetanib Substances 0.000 description 1
• 239000002145 L01XE14 - Bosutinib Substances 0.000 description 1
• 239000002146 L01XE16 - Crizotinib Substances 0.000 description 1
• 239000002144 L01XE18 - Ruxolitinib Substances 0.000 description 1
• 239000002138 L01XE21 - Regorafenib Substances 0.000 description 1
• 239000002176 L01XE26 - Cabozantinib Substances 0.000 description 1
• 239000002177 L01XE27 - Ibrutinib Substances 0.000 description 1
• UIARLYUEJFELEN-LROUJFHJSA-N LSM-1231 Chemical compound C12=C3N4C5=CC=CC=C5C3=C3C(=O)NCC3=C2C2=CC=CC=C2N1[C@]1(C)[C@](CO)(O)C[C@H]4O1 UIARLYUEJFELEN-LROUJFHJSA-N 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 239000005639 Lauric acid Substances 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• 229940124647 MEK inhibitor Drugs 0.000 description 1
• 206010027398 Mesenteric fibrosis Diseases 0.000 description 1
• 101710143111 Mothers against decapentaplegic homolog 3 Proteins 0.000 description 1
• 208000034578 Multiple myelomas Diseases 0.000 description 1
• 241001529936 Murinae Species 0.000 description 1
• 241000699660 Mus musculus Species 0.000 description 1
• 101100381978 Mus musculus Braf gene Proteins 0.000 description 1
• 206010028289 Muscle atrophy Diseases 0.000 description 1
• 102100025243 Myeloid cell surface antigen CD33 Human genes 0.000 description 1
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
• HRNLUBSXIHFDHP-UHFFFAOYSA-N N-(2-aminophenyl)-4-[[[4-(3-pyridinyl)-2-pyrimidinyl]amino]methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC1=NC=CC(C=2C=NC=CC=2)=N1 HRNLUBSXIHFDHP-UHFFFAOYSA-N 0.000 description 1
• FQFNSCABOQPBJN-UHFFFAOYSA-N N-(3-bromo-2-chloropyridin-4-yl)acetamide Chemical compound BrC=1C(=NC=CC=1NC(C)=O)Cl FQFNSCABOQPBJN-UHFFFAOYSA-N 0.000 description 1
• SUKXKLNDBLNTSW-UHFFFAOYSA-N N-(4-hydroxycyclohexyl)-6-phenylhexanamide Chemical compound OC1CCC(CC1)NC(CCCCCC1=CC=CC=C1)=O SUKXKLNDBLNTSW-UHFFFAOYSA-N 0.000 description 1
• FISDJHXLTJPLAG-UHFFFAOYSA-N N-[2-chloro-3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridin-4-yl]acetamide Chemical compound ClC1=NC=CC(=C1C=1C=CC=2N(C=1)C(=CN=2)C#N)NC(C)=O FISDJHXLTJPLAG-UHFFFAOYSA-N 0.000 description 1
• AHIHHHDVKREJBC-UHFFFAOYSA-N N-[5-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-6-(6-methylpyridin-2-yl)pyridin-3-yl]acetamide Chemical compound C(#N)C1=CN=C2N1C=C(C=C2)C=1C(=NC=C(C=1)NC(C)=O)C1=NC(=CC=C1)C AHIHHHDVKREJBC-UHFFFAOYSA-N 0.000 description 1
• HSUXLMSGKDVTIT-UHFFFAOYSA-N N-[6-[3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]pyridin-2-yl]acetamide Chemical compound C(#N)C1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)NC(C)=O HSUXLMSGKDVTIT-UHFFFAOYSA-N 0.000 description 1
• ZRGNLZYIHYFMQD-UHFFFAOYSA-N N-[6-chloro-5-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]acetamide Chemical compound ClC1=C(C=CC(=N1)NC(C)=O)C=1C=CC=2N(C=1)C(=CN=2)C#N ZRGNLZYIHYFMQD-UHFFFAOYSA-N 0.000 description 1
• AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
• OFZIOLOVTPXWRT-UHFFFAOYSA-N N-cyclopropyl-5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1(CC1)NC(=O)C=1C=NN2C=1N=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C OFZIOLOVTPXWRT-UHFFFAOYSA-N 0.000 description 1
• CWXWDPPYKNSCCP-UHFFFAOYSA-N N-cyclopropyl-5-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1(CC1)NC(=O)C=1C=NN2C=1N=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C(F)(F)F CWXWDPPYKNSCCP-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
• QTYWTUBOKDSNSV-UHFFFAOYSA-N N-methyl-5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CNC(=O)C=1C=NN2C=1N=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C QTYWTUBOKDSNSV-UHFFFAOYSA-N 0.000 description 1
• FMPGYEQOFMRWOU-UHFFFAOYSA-N N-tert-butyl-6-(2-chloropyridin-3-yl)imidazo[1,2-a]pyridin-3-amine Chemical compound C(C)(C)(C)NC1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)Cl FMPGYEQOFMRWOU-UHFFFAOYSA-N 0.000 description 1
• 208000012902 Nervous system disease Diseases 0.000 description 1
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
• 206010030247 Oestrogen deficiency Diseases 0.000 description 1
• 206010049088 Osteopenia Diseases 0.000 description 1
• 206010033128 Ovarian cancer Diseases 0.000 description 1
• 206010061535 Ovarian neoplasm Diseases 0.000 description 1
• 239000012270 PD-1 inhibitor Substances 0.000 description 1
• 239000012668 PD-1-inhibitor Substances 0.000 description 1
• 239000012271 PD-L1 inhibitor Substances 0.000 description 1
• 108091007960 PI3Ks Proteins 0.000 description 1
• 102000038030 PI3Ks Human genes 0.000 description 1
• 229930012538 Paclitaxel Natural products 0.000 description 1
• 235000021314 Palmitic acid Nutrition 0.000 description 1
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
• 241000009328 Perro Species 0.000 description 1
• 235000014676 Phragmites communis Nutrition 0.000 description 1
• 206010035226 Plasma cell myeloma Diseases 0.000 description 1
• 239000004698 Polyethylene Substances 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
• 208000012654 Primary biliary cholangitis Diseases 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
• 229940079156 Proteasome inhibitor Drugs 0.000 description 1
• 102000001253 Protein Kinase Human genes 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 208000015634 Rectal Neoplasms Diseases 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 206010038979 Retroperitoneal fibrosis Diseases 0.000 description 1
• 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
• 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
• 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 206010039580 Scar Diseases 0.000 description 1
• 102100034136 Serine/threonine-protein kinase receptor R3 Human genes 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• 102000049939 Smad3 Human genes 0.000 description 1
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
• 235000014459 Sorbus Nutrition 0.000 description 1
• 241001092391 Sorbus Species 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 238000006619 Stille reaction Methods 0.000 description 1
• 108091005735 TGF-beta receptors Proteins 0.000 description 1
• 229940123237 Taxane Drugs 0.000 description 1
• 239000004809 Teflon Substances 0.000 description 1
• 229920006362 Teflon® Polymers 0.000 description 1
• BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
• 208000024770 Thyroid neoplasm Diseases 0.000 description 1
• 102000016715 Transforming Growth Factor beta Receptors Human genes 0.000 description 1
• 102000011117 Transforming Growth Factor beta2 Human genes 0.000 description 1
• 108010011702 Transforming Growth Factor-beta Type I Receptor Proteins 0.000 description 1
• 101800000304 Transforming growth factor beta-2 Proteins 0.000 description 1
• 108090000097 Transforming growth factor beta-3 Proteins 0.000 description 1
• 102000056172 Transforming growth factor beta-3 Human genes 0.000 description 1
• 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
• 240000001717 Vaccinium macrocarpon Species 0.000 description 1
• 235000012545 Vaccinium macrocarpon Nutrition 0.000 description 1
• 235000002118 Vaccinium oxycoccus Nutrition 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
• 229940122803 Vinca alkaloid Drugs 0.000 description 1
• 206010052428 Wound Diseases 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[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@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
• PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
• DACWQSNZECJJGG-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CN=C21 DACWQSNZECJJGG-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• 229940081735 acetylcellulose Drugs 0.000 description 1
• ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
• 239000003929 acidic solution Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 230000001464 adherent effect Effects 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 230000001070 adhesive effect Effects 0.000 description 1
• 239000001361 adipic acid Substances 0.000 description 1
• 235000011037 adipic acid Nutrition 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 201000005188 adrenal gland cancer Diseases 0.000 description 1
• 208000024447 adrenal gland neoplasm Diseases 0.000 description 1
• 229960001686 afatinib Drugs 0.000 description 1
• ULXXDDBFHOBEHA-CWDCEQMOSA-N afatinib Chemical compound N1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 ULXXDDBFHOBEHA-CWDCEQMOSA-N 0.000 description 1
• 238000013019 agitation Methods 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• 229960000548 alemtuzumab Drugs 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910001413 alkali metal ion Inorganic materials 0.000 description 1
• 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
• 150000001336 alkenes Chemical class 0.000 description 1
• 125000003342 alkenyl group Chemical group 0.000 description 1
• 150000001345 alkine derivatives Chemical class 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 150000001413 amino acids Chemical group 0.000 description 1
• ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 1
• 229960003437 aminoglutethimide Drugs 0.000 description 1
• 235000011114 ammonium hydroxide Nutrition 0.000 description 1
• 150000003863 ammonium salts Chemical class 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
• 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 1
• 229960002932 anastrozole Drugs 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 229940121363 anti-inflammatory agent Drugs 0.000 description 1
• 239000002260 anti-inflammatory agent Substances 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 230000001028 anti-proliverative effect Effects 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 229940034982 antineoplastic agent Drugs 0.000 description 1
• 229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 description 1
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000003078 antioxidant effect Effects 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• 229940124522 antiretrovirals Drugs 0.000 description 1
• 239000003903 antiretrovirus agent Substances 0.000 description 1
• 239000003443 antiviral agent Substances 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 239000003886 aromatase inhibitor Substances 0.000 description 1
• 229940046844 aromatase inhibitors Drugs 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 239000012131 assay buffer Substances 0.000 description 1
• 229960003005 axitinib Drugs 0.000 description 1
• RITAVMQDGBJQJZ-FMIVXFBMSA-N axitinib Chemical compound CNC(=O)C1=CC=CC=C1SC1=CC=C(C(\C=C\C=2N=CC=CC=2)=NN2)C2=C1 RITAVMQDGBJQJZ-FMIVXFBMSA-N 0.000 description 1
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
• 229960002170 azathioprine Drugs 0.000 description 1
• LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
• 235000013871 bee wax Nutrition 0.000 description 1
• 239000012166 beeswax Substances 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 229960000397 bevacizumab Drugs 0.000 description 1
• 239000011230 binding agent Substances 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
• 230000003115 biocidal effect Effects 0.000 description 1
• 230000033228 biological regulation Effects 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
• 238000006664 bond formation reaction Methods 0.000 description 1
• 229940112869 bone morphogenetic protein Drugs 0.000 description 1
• 230000024279 bone resorption Effects 0.000 description 1
• 229960001467 bortezomib Drugs 0.000 description 1
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 1
• 229960003736 bosutinib Drugs 0.000 description 1
• UBPYILGKFZZVDX-UHFFFAOYSA-N bosutinib Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl UBPYILGKFZZVDX-UHFFFAOYSA-N 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229940045348 brown mixture Drugs 0.000 description 1
• 239000007853 buffer solution Substances 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 229960002092 busulfan Drugs 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229960001292 cabozantinib Drugs 0.000 description 1
• ONIQOQHATWINJY-UHFFFAOYSA-N cabozantinib Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 ONIQOQHATWINJY-UHFFFAOYSA-N 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
• 229940127093 camptothecin Drugs 0.000 description 1
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
• 229960004117 capecitabine Drugs 0.000 description 1
• KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 229960004562 carboplatin Drugs 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 229960002438 carfilzomib Drugs 0.000 description 1
• BLMPQMFVWMYDKT-NZTKNTHTSA-N carfilzomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(C)OC1)NC(=O)CN1CCOCC1)CC1=CC=CC=C1 BLMPQMFVWMYDKT-NZTKNTHTSA-N 0.000 description 1
• 108010021331 carfilzomib Proteins 0.000 description 1
• 229960005243 carmustine Drugs 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 229960002412 cediranib Drugs 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 239000013592 cell lysate Substances 0.000 description 1
• 239000002458 cell surface marker Substances 0.000 description 1
• 229920002301 cellulose acetate Polymers 0.000 description 1
• 229960001602 ceritinib Drugs 0.000 description 1
• WRXDGGCKOUEOPW-UHFFFAOYSA-N ceritinib Chemical compound CC=1C=C(NC=2N=C(NC=3C(=CC=CC=3)NS(=O)(=O)C(C)C)C(Cl)=CN=2)C(OC(C)C)=CC=1C1CCNCC1 WRXDGGCKOUEOPW-UHFFFAOYSA-N 0.000 description 1
• 229960005395 cetuximab Drugs 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 229940044683 chemotherapy drug Drugs 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
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
• 235000019416 cholic acid Nutrition 0.000 description 1
• 229960002471 cholic acid Drugs 0.000 description 1
• 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 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
• 229960002436 cladribine Drugs 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• 229960001338 colchicine Drugs 0.000 description 1
• 229920001436 collagen Polymers 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• 201000002758 colorectal adenoma Diseases 0.000 description 1
• 239000002131 composite material Substances 0.000 description 1
• 229940125904 compound 1 Drugs 0.000 description 1
• 229940125773 compound 10 Drugs 0.000 description 1
• 229940126142 compound 16 Drugs 0.000 description 1
• 229940126540 compound 41 Drugs 0.000 description 1
• 230000037011 constitutive activity Effects 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 235000004634 cranberry Nutrition 0.000 description 1
• 229960005061 crizotinib Drugs 0.000 description 1
• KTEIFNKAUNYNJU-GFCCVEGCSA-N crizotinib Chemical compound O([C@H](C)C=1C(=C(F)C=CC=1Cl)Cl)C(C(=NC=1)N)=CC=1C(=C1)C=NN1C1CCNCC1 KTEIFNKAUNYNJU-GFCCVEGCSA-N 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229960000684 cytarabine Drugs 0.000 description 1
• 229960002465 dabrafenib Drugs 0.000 description 1
• BFSMGDJOXZAERB-UHFFFAOYSA-N dabrafenib Chemical compound S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 BFSMGDJOXZAERB-UHFFFAOYSA-N 0.000 description 1
• 229960003901 dacarbazine Drugs 0.000 description 1
• 229960002448 dasatinib Drugs 0.000 description 1
• 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 1
• 229960000975 daunorubicin Drugs 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000007850 degeneration Effects 0.000 description 1
• KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
• 150000001975 deuterium Chemical group 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
• 229960003957 dexamethasone Drugs 0.000 description 1
• 229960005215 dichloroacetic acid Drugs 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 125000005992 dihydrobenzisothiazinyl group Chemical group 0.000 description 1
• DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 description 1
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
• 125000005046 dihydronaphthyl group Chemical group 0.000 description 1
• 125000005051 dihydropyrazinyl group Chemical group N1(CC=NC=C1)* 0.000 description 1
• 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 description 1
• 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
• 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 description 1
• 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
• 229960003668 docetaxel Drugs 0.000 description 1
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 230000009977 dual effect Effects 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 229950009791 durvalumab Drugs 0.000 description 1
• 125000006575 electron-withdrawing group Chemical group 0.000 description 1
• 229960004137 elotuzumab Drugs 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 239000003974 emollient agent Substances 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 230000007613 environmental effect Effects 0.000 description 1
• 229940088598 enzyme Drugs 0.000 description 1
• 239000002532 enzyme inhibitor Substances 0.000 description 1
• 230000036566 epidermal hyperplasia Effects 0.000 description 1
• 210000002919 epithelial cell Anatomy 0.000 description 1
• 229960001433 erlotinib Drugs 0.000 description 1
• 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 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• MKYGSVYREJKOER-UHFFFAOYSA-N ethyl 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C(=O)OCC MKYGSVYREJKOER-UHFFFAOYSA-N 0.000 description 1
• CLCQZYFKDJIJLM-UHFFFAOYSA-N ethyl 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-2-carboxylate Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)C(=O)OCC CLCQZYFKDJIJLM-UHFFFAOYSA-N 0.000 description 1
• VLMBQPTXLCQBHA-UHFFFAOYSA-N ethyl 6-[2-[6-(trifluoromethyl)pyridin-2-yl]pyridin-3-yl]imidazo[1,2-a]pyridine-2-carboxylate Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C=C(N=2)C(=O)OCC)(F)F VLMBQPTXLCQBHA-UHFFFAOYSA-N 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
• JEMAMNBFHPIPCR-UHFFFAOYSA-N ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound C1=CC=NC2=C(C(=O)OCC)C=NN21 JEMAMNBFHPIPCR-UHFFFAOYSA-N 0.000 description 1
• 229940043351 ethyl-p-hydroxybenzoate Drugs 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
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000004299 exfoliation Methods 0.000 description 1
• 210000002744 extracellular matrix Anatomy 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 229960000390 fludarabine Drugs 0.000 description 1
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 239000011888 foil Substances 0.000 description 1
• OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
• 229960004421 formestane Drugs 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 230000009760 functional impairment Effects 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 229960002584 gefitinib Drugs 0.000 description 1
• 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 1
• 239000000499 gel Substances 0.000 description 1
• 229960000578 gemtuzumab Drugs 0.000 description 1
• 229960005219 gentisic acid Drugs 0.000 description 1
• 208000005017 glioblastoma Diseases 0.000 description 1
• 201000003617 glucocorticoid-induced osteoporosis Diseases 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 229950006191 gluconic acid Drugs 0.000 description 1
• 229940074045 glyceryl distearate Drugs 0.000 description 1
• 229940075507 glyceryl monostearate Drugs 0.000 description 1
• 210000002149 gonad Anatomy 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 239000007902 hard capsule Substances 0.000 description 1
• 230000035876 healing Effects 0.000 description 1
• 239000003481 heat shock protein 90 inhibitor Substances 0.000 description 1
• 239000001307 helium Substances 0.000 description 1
• 229910052734 helium Inorganic materials 0.000 description 1
• SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
• 208000006454 hepatitis Diseases 0.000 description 1
• 231100000283 hepatitis Toxicity 0.000 description 1
• 208000002672 hepatitis B Diseases 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
• FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
• 239000003906 humectant Substances 0.000 description 1
• 229960000443 hydrochloric acid Drugs 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 229950000801 hydroxyprogesterone caproate Drugs 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 206010020718 hyperplasia Diseases 0.000 description 1
• 229960001507 ibrutinib Drugs 0.000 description 1
• XYFPWWZEPKGCCK-GOSISDBHSA-N ibrutinib Chemical compound C1=2C(N)=NC=NC=2N([C@H]2CN(CCC2)C(=O)C=C)N=C1C(C=C1)=CC=C1OC1=CC=CC=C1 XYFPWWZEPKGCCK-GOSISDBHSA-N 0.000 description 1
• 229960001101 ifosfamide Drugs 0.000 description 1
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
• 229960002411 imatinib Drugs 0.000 description 1
• KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound 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 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 1
• RTOFMMILZZGGNS-UHFFFAOYSA-N imidazo[1,2-a]pyridin-3-amine Chemical compound C1=CC=CN2C(N)=CN=C21 RTOFMMILZZGGNS-UHFFFAOYSA-N 0.000 description 1
• SGRMUAZFOWNSGE-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carboxylic acid Chemical compound C1=CC=NN2C(C(=O)O)=CN=C21 SGRMUAZFOWNSGE-UHFFFAOYSA-N 0.000 description 1
• 125000005945 imidazopyridyl group Chemical group 0.000 description 1
• 150000002466 imines Chemical group 0.000 description 1
• 239000012274 immune-checkpoint protein inhibitor Substances 0.000 description 1
• 230000000091 immunopotentiator Effects 0.000 description 1
• 229960003444 immunosuppressant agent Drugs 0.000 description 1
• 239000003018 immunosuppressive agent Substances 0.000 description 1
• 238000010874 in vitro model Methods 0.000 description 1
• 230000000415 inactivating effect Effects 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 230000004968 inflammatory condition Effects 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 239000000893 inhibin Substances 0.000 description 1
• 229940102223 injectable solution Drugs 0.000 description 1
• 229940102213 injectable suspension Drugs 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 229960003130 interferon gamma Drugs 0.000 description 1
• 208000036971 interstitial lung disease 2 Diseases 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• 238000007918 intramuscular 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
• 238000004255 ion exchange chromatography Methods 0.000 description 1
• 229960005386 ipilimumab Drugs 0.000 description 1
• 229910052741 iridium Inorganic materials 0.000 description 1
• GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
• 229960004768 irinotecan Drugs 0.000 description 1
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
• 229940045996 isethionic acid Drugs 0.000 description 1
• 125000005994 isobenzotetrahydrofuranyl group Chemical group 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 210000001117 keloid Anatomy 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229940099563 lactobionic acid Drugs 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229960004891 lapatinib Drugs 0.000 description 1
• 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 1
• 229960004942 lenalidomide Drugs 0.000 description 1
• GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 description 1
• 229950001845 lestaurtinib Drugs 0.000 description 1
• CMJCXYNUCSMDBY-ZDUSSCGKSA-N lgx818 Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=C(Cl)C=2)F)=N1 CMJCXYNUCSMDBY-ZDUSSCGKSA-N 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 125000005647 linker group Chemical group 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 229950011263 lirilumab Drugs 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 208000014018 liver neoplasm Diseases 0.000 description 1
• RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
• 239000003589 local anesthetic agent Substances 0.000 description 1
• 229960005015 local anesthetics Drugs 0.000 description 1
• 230000005923 long-lasting effect Effects 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 229940124302 mTOR inhibitor Drugs 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
• 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 229960004616 medroxyprogesterone Drugs 0.000 description 1
• FRQMUZJSZHZSGN-HBNHAYAOSA-N medroxyprogesterone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FRQMUZJSZHZSGN-HBNHAYAOSA-N 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 230000037353 metabolic pathway Effects 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• IAHBCNYZHANKLZ-UHFFFAOYSA-N methyl 2-chloro-3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridine-4-carboxylate Chemical compound ClC=1C(=C(C(=O)OC)C=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C#N IAHBCNYZHANKLZ-UHFFFAOYSA-N 0.000 description 1
• OAIGGGNSCWNWCA-UHFFFAOYSA-N methyl 3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-2-(6-methylpyridin-2-yl)pyridine-4-carboxylate Chemical compound C(#N)C1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1C(=O)OC)C1=NC(=CC=C1)C OAIGGGNSCWNWCA-UHFFFAOYSA-N 0.000 description 1
• ORLGXFJJEPIDMQ-UHFFFAOYSA-N methyl 3-bromo-2-chloropyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(Cl)=C1Br ORLGXFJJEPIDMQ-UHFFFAOYSA-N 0.000 description 1
• GMNQJDRCBDRXLA-UHFFFAOYSA-N methyl 6-[3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]pyridine-3-carboxylate Chemical compound C(#N)C1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)C1=NC=C(C=C1)C(=O)OC GMNQJDRCBDRXLA-UHFFFAOYSA-N 0.000 description 1
• NFLROFLPSNZIAH-UHFFFAOYSA-N methyl 6-bromopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(Br)N=C1 NFLROFLPSNZIAH-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
• 229960001156 mitoxantrone Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 150000002772 monosaccharides Chemical class 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 238000010172 mouse model Methods 0.000 description 1
• 230000020763 muscle atrophy Effects 0.000 description 1
• 201000000585 muscular atrophy Diseases 0.000 description 1
• 210000000107 myocyte Anatomy 0.000 description 1
• BHDACNOAMZZZHQ-UHFFFAOYSA-N n-(6-bromopyridin-2-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(Br)=N1 BHDACNOAMZZZHQ-UHFFFAOYSA-N 0.000 description 1
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
• WGLUNLJVYNJMBU-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-n-[(3-methyl-1-oxo-2,4-dihydroisoquinolin-3-yl)methyl]decanamide Chemical compound C1=CC=C2C(=O)NC(CN(CCN(C)C)C(=O)CCCCCCCCC)(C)CC2=C1 WGLUNLJVYNJMBU-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 229910052754 neon Inorganic materials 0.000 description 1
• GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
• 230000002232 neuromuscular Effects 0.000 description 1
• 230000003472 neutralizing effect Effects 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• 229960001346 nilotinib Drugs 0.000 description 1
• HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 description 1
• 229940074355 nitric acid Drugs 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 229960003301 nivolumab Drugs 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
• 239000007764 o/w emulsion Substances 0.000 description 1
• 230000000414 obstructive effect Effects 0.000 description 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
• 229960002969 oleic acid Drugs 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 229960005010 orotic acid Drugs 0.000 description 1
• 229910052762 osmium Inorganic materials 0.000 description 1
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
• 230000011164 ossification Effects 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 229940116315 oxalic acid Drugs 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
• OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 0.000 description 1
• 229960001592 paclitaxel Drugs 0.000 description 1
• 229960004390 palbociclib Drugs 0.000 description 1
• AHJRHEGDXFFMBM-UHFFFAOYSA-N palbociclib Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 AHJRHEGDXFFMBM-UHFFFAOYSA-N 0.000 description 1
• UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• 201000002528 pancreatic cancer Diseases 0.000 description 1
• 208000008443 pancreatic carcinoma Diseases 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 229960000639 pazopanib Drugs 0.000 description 1
• CUIHSIWYWATEQL-UHFFFAOYSA-N pazopanib Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CUIHSIWYWATEQL-UHFFFAOYSA-N 0.000 description 1
• 229940121655 pd-1 inhibitor Drugs 0.000 description 1
• 229940121656 pd-l1 inhibitor Drugs 0.000 description 1
• 229960002621 pembrolizumab Drugs 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 230000002085 persistent effect Effects 0.000 description 1
• XOVFEHTVWFQNOW-UHFFFAOYSA-N phenyl(phosphanyl)phosphane Chemical group PPC1=CC=CC=C1 XOVFEHTVWFQNOW-UHFFFAOYSA-N 0.000 description 1
• 230000026731 phosphorylation Effects 0.000 description 1
• 238000006366 phosphorylation reaction Methods 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
• 230000035479 physiological effects, processes and functions Effects 0.000 description 1
• 230000035790 physiological processes and functions Effects 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical group O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
• 150000003057 platinum Chemical class 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 238000002600 positron emission tomography Methods 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
• 201000007271 pre-malignant neoplasm Diseases 0.000 description 1
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
• 229960004618 prednisone Drugs 0.000 description 1
• 238000012746 preparative thin layer chromatography Methods 0.000 description 1
• 230000002335 preservative effect Effects 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
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• 230000002062 proliferating effect Effects 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000003207 proteasome inhibitor Substances 0.000 description 1
• 108060006633 protein kinase Proteins 0.000 description 1
• 239000003909 protein kinase inhibitor Substances 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• UMLDUMMLRZFROX-UHFFFAOYSA-N pyridin-2-ylboronic acid Chemical compound OB(O)C1=CC=CC=N1 UMLDUMMLRZFROX-UHFFFAOYSA-N 0.000 description 1
• 125000004590 pyridopyridyl group Chemical group N1=C(C=CC2=C1C=CC=N2)* 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000004620 quinolinyl-N-oxide group Chemical group 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 206010038038 rectal cancer Diseases 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 201000001275 rectum cancer Diseases 0.000 description 1
• 230000008929 regeneration Effects 0.000 description 1
• 238000011069 regeneration method Methods 0.000 description 1
• 229960004836 regorafenib Drugs 0.000 description 1
• FNHKPVJBJVTLMP-UHFFFAOYSA-N regorafenib Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=C(F)C(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 FNHKPVJBJVTLMP-UHFFFAOYSA-N 0.000 description 1
• 238000000611 regression analysis Methods 0.000 description 1
• 201000002793 renal fibrosis Diseases 0.000 description 1
• 230000008439 repair process Effects 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 208000023504 respiratory system disease Diseases 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• HFNKQEVNSGCOJV-OAHLLOKOSA-N ruxolitinib Chemical compound C1([C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCCC1 HFNKQEVNSGCOJV-OAHLLOKOSA-N 0.000 description 1
• 229960000215 ruxolitinib Drugs 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 229950003647 semaxanib Drugs 0.000 description 1
• WUWDLXZGHZSWQZ-WQLSENKSSA-N semaxanib Chemical compound N1C(C)=CC(C)=C1\C=C/1C2=CC=CC=C2NC\1=O WUWDLXZGHZSWQZ-WQLSENKSSA-N 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 230000007781 signaling event Effects 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000001488 sodium phosphate Substances 0.000 description 1
• 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 239000007901 soft capsule Substances 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 229960003787 sorafenib Drugs 0.000 description 1
• 239000001593 sorbitan monooleate Substances 0.000 description 1
• 235000011069 sorbitan monooleate Nutrition 0.000 description 1
• 229940035049 sorbitan monooleate Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 230000006641 stabilisation Effects 0.000 description 1
• 238000011105 stabilization Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000004659 sterilization and disinfection Methods 0.000 description 1
• 230000000638 stimulation Effects 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 150000005846 sugar alcohols Chemical class 0.000 description 1
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
• BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 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
• 230000004083 survival effect Effects 0.000 description 1
• 230000002459 sustained effect Effects 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 229960001603 tamoxifen Drugs 0.000 description 1
• 229950007866 tanespimycin Drugs 0.000 description 1
• AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 description 1
• 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 1
• 229960004964 temozolomide Drugs 0.000 description 1
• QFJCIRLUMZQUOT-UHFFFAOYSA-N temsirolimus Natural products C1CC(O)C(OC)CC1CC(C)C1OC(=O)C2CCCCN2C(=O)C(=O)C(O)(O2)C(C)CCC2CC(OC)C(C)=CC=CC=CC(C)CC(C)C(=O)C(OC)C(O)C(C)=CC(C)C(=O)C1 QFJCIRLUMZQUOT-UHFFFAOYSA-N 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
• 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 229960003433 thalidomide Drugs 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 150000007970 thio esters Chemical class 0.000 description 1
• 125000003396 thiol group Chemical group [H]S* 0.000 description 1
• 201000002510 thyroid cancer Diseases 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
• 229960003989 tocilizumab Drugs 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 229960000303 topotecan Drugs 0.000 description 1
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
• 229960005267 tositumomab Drugs 0.000 description 1
• 229960004066 trametinib Drugs 0.000 description 1
• 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 1
• 238000012546 transfer Methods 0.000 description 1
• 238000011830 transgenic mouse model Methods 0.000 description 1
• 229960000575 trastuzumab Drugs 0.000 description 1
• 229960001612 trastuzumab emtansine Drugs 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
• UNEPXPMBVGDXGH-UHFFFAOYSA-N tributyl(pyridin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NC=C1 UNEPXPMBVGDXGH-UHFFFAOYSA-N 0.000 description 1
• SRBYIFPGENOZFS-UHFFFAOYSA-N tributyl-(6-chloropyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC(Cl)=N1 SRBYIFPGENOZFS-UHFFFAOYSA-N 0.000 description 1
• BAVYZALUXZFZLV-FIBGUPNXSA-N trideuteriomethanamine Chemical compound [2H]C([2H])([2H])N BAVYZALUXZFZLV-FIBGUPNXSA-N 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
• 229950002929 trinitrophenol Drugs 0.000 description 1
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
• 231100000397 ulcer Toxicity 0.000 description 1
• 229960002703 undecylenic acid Drugs 0.000 description 1
• 238000011144 upstream manufacturing Methods 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 229960005486 vaccine Drugs 0.000 description 1
• 206010046885 vaginal cancer Diseases 0.000 description 1
• 208000013139 vaginal neoplasm Diseases 0.000 description 1
• 229940005605 valeric acid Drugs 0.000 description 1
• 229960000241 vandetanib Drugs 0.000 description 1
• UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 description 1
• 208000019553 vascular disease Diseases 0.000 description 1
• 229950000578 vatalanib Drugs 0.000 description 1
• YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 description 1
• 229960003862 vemurafenib Drugs 0.000 description 1
• GPXBXXGIAQBQNI-UHFFFAOYSA-N vemurafenib Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(Cl)=CC=2)=C1F GPXBXXGIAQBQNI-UHFFFAOYSA-N 0.000 description 1
• LQBVNQSMGBZMKD-UHFFFAOYSA-N venetoclax Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C3C=CNC3=NC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 LQBVNQSMGBZMKD-UHFFFAOYSA-N 0.000 description 1
• 229960001183 venetoclax 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
• 229960004528 vincristine Drugs 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
• 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
• 230000003612 virological effect Effects 0.000 description 1
• WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
• 229960000237 vorinostat Drugs 0.000 description 1
• 230000029663 wound healing Effects 0.000 description 1
• 229940055760 yervoy Drugs 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1