CA2680796A1 - Inhibitors of the hedgehog pathway - Google Patents

Info

Publication number

CA2680796A1

CA2680796A1 CA002680796A CA2680796A CA2680796A1 CA 2680796 A1 CA2680796 A1 CA 2680796A1 CA 002680796 A CA002680796 A CA 002680796A CA 2680796 A CA2680796 A CA 2680796A CA 2680796 A1 CA2680796 A1 CA 2680796A1

Authority

CA

Canada

Prior art keywords

amino

benzamide

methyl

phenylquinazolin

compound

Prior art date

2007-03-14

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 230000037361 pathway Effects 0.000 title claims description 25
• 239000003112 inhibitor Substances 0.000 title description 3
• 241000289669 Erinaceus europaeus Species 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 765
• 150000003839 salts Chemical class 0.000 claims abstract description 98
• 239000012453 solvate Substances 0.000 claims abstract description 80
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 48
• 238000000034 method Methods 0.000 claims abstract description 39
• 201000011510 cancer Diseases 0.000 claims abstract description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 597
• -1 pyrido[3,2-d]pyrimidinyl Chemical group 0.000 claims description 464
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 360
• 229910052739 hydrogen Inorganic materials 0.000 claims description 322
• 239000001257 hydrogen Substances 0.000 claims description 320
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 291
• 125000001072 heteroaryl group Chemical group 0.000 claims description 181
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 177
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 177
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 130
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 88
• 125000003545 alkoxy group Chemical group 0.000 claims description 85
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 84
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 80
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 75
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 74
• 125000003282 alkyl amino group Chemical group 0.000 claims description 55
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 55
• 125000001188 haloalkyl group Chemical group 0.000 claims description 52
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 47
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 41
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 40
• 239000000203 mixture Substances 0.000 claims description 40
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 36
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 32
• 201000010099 disease Diseases 0.000 claims description 30
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 30
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 27
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 27
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
• 125000005122 aminoalkylamino group Chemical group 0.000 claims description 19
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 18
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 10
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 10
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
• 125000005059 halophenyl group Chemical group 0.000 claims description 9
• 108090000623 proteins and genes Proteins 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000002431 aminoalkoxy group Chemical group 0.000 claims description 6
• ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 102000004169 proteins and genes Human genes 0.000 claims description 6
• 206010004146 Basal cell carcinoma Diseases 0.000 claims description 5
• 208000000172 Medulloblastoma Diseases 0.000 claims description 5
• 208000034578 Multiple myelomas Diseases 0.000 claims description 5
• 206010027191 meningioma Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 4
• 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 4
• 201000001441 melanoma Diseases 0.000 claims description 4
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
• 208000020790 biliary tract neoplasm Diseases 0.000 claims description 3
• 208000029742 colonic neoplasm Diseases 0.000 claims description 3
• YYKJUIOOPHHRFU-UHFFFAOYSA-N cyclohexyl-[4-[(4-phenylquinazolin-2-yl)amino]piperidin-1-yl]methanone Chemical compound C1CC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)CCN1C(=O)C1CCCCC1 YYKJUIOOPHHRFU-UHFFFAOYSA-N 0.000 claims description 3
• 201000004101 esophageal cancer Diseases 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• 210000004498 neuroglial cell Anatomy 0.000 claims description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
• 208000000587 small cell lung carcinoma Diseases 0.000 claims description 3
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
• DTHKCNXTNNJZSX-UHFFFAOYSA-N (2,6-dichlorophenyl)-[4-[(4-phenylquinazolin-2-yl)amino]piperidin-1-yl]methanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)N1CCC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)CC1 DTHKCNXTNNJZSX-UHFFFAOYSA-N 0.000 claims description 2
• YIHKSGNMTOHYDK-UHFFFAOYSA-N 2-phenyl-1-[4-[(4-phenylquinazolin-2-yl)amino]piperidin-1-yl]ethanone Chemical compound C1CC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)CCN1C(=O)CC1=CC=CC=C1 YIHKSGNMTOHYDK-UHFFFAOYSA-N 0.000 claims description 2
• KGTQCIOUFZKURE-UHFFFAOYSA-N 2-phenyl-1-[4-[(4-phenylquinazolin-2-yl)amino]piperidin-1-yl]propan-1-one Chemical compound C=1C=CC=CC=1C(C)C(=O)N(CC1)CCC1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 KGTQCIOUFZKURE-UHFFFAOYSA-N 0.000 claims description 2
• 206010006187 Breast cancer Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 206010017758 gastric cancer Diseases 0.000 claims description 2
• 208000005017 glioblastoma Diseases 0.000 claims description 2
• IQHVMZMNEYKFFM-UHFFFAOYSA-N n-(5-cyano-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C#N)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 IQHVMZMNEYKFFM-UHFFFAOYSA-N 0.000 claims description 2
• BHFUFENWFRFQNX-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-4-[(4-phenylquinazolin-2-yl)amino]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC(=O)N1CCC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)CC1 BHFUFENWFRFQNX-UHFFFAOYSA-N 0.000 claims description 2
• YQPHYWFLVNTVLE-UHFFFAOYSA-N n-[1-(1h-benzimidazol-2-yl)piperidin-4-yl]-4-phenylquinazolin-2-amine Chemical compound C1CN(C=2NC3=CC=CC=C3N=2)CCC1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 YQPHYWFLVNTVLE-UHFFFAOYSA-N 0.000 claims description 2
• LHIVWHGYIADBPC-UHFFFAOYSA-N n-[1-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]piperidin-4-yl]-4-phenylquinazolin-2-amine Chemical compound CC1=NOC(C)=C1S(=O)(=O)N1CCC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)CC1 LHIVWHGYIADBPC-UHFFFAOYSA-N 0.000 claims description 2
• JETGRRZTECZVLO-UHFFFAOYSA-N phenyl-[4-[(4-phenylquinazolin-2-yl)amino]piperidin-1-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)N(CC1)CCC1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 JETGRRZTECZVLO-UHFFFAOYSA-N 0.000 claims description 2
• 230000002062 proliferating effect Effects 0.000 claims description 2
• 201000011549 stomach cancer Diseases 0.000 claims description 2
• NNCJUAGSDYKTHL-UHFFFAOYSA-N tert-butyl 3-[4-[(4-phenylquinazolin-2-yl)amino]piperidine-1-carbonyl]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC1C(=O)N1CCC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)CC1 NNCJUAGSDYKTHL-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 13
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
• 125000001475 halogen functional group Chemical group 0.000 claims 10
• TXBIICIGOXHJDJ-UHFFFAOYSA-N 1-[[4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN1CC(C(O)=O)C1 TXBIICIGOXHJDJ-UHFFFAOYSA-N 0.000 claims 1
• MEVUWLWVJWHWSI-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1-[4-[(4-phenylquinazolin-2-yl)amino]piperidin-1-yl]ethanone Chemical compound ClC1=CC=CC(Cl)=C1CC(=O)N1CCC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)CC1 MEVUWLWVJWHWSI-UHFFFAOYSA-N 0.000 claims 1
• JQBSGSYNHIERKC-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)-5-[(4-phenylquinazolin-2-yl)amino]isoindole-1,3-dione Chemical compound CC1=CC=CC(C)=C1N1C(=O)C2=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=C2C1=O JQBSGSYNHIERKC-UHFFFAOYSA-N 0.000 claims 1
• LWMLQGPYZGOEBL-UHFFFAOYSA-N 3-[2-[4-[(2,6-dimethylphenyl)carbamoyl]anilino]quinazolin-4-yl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2C3=CC=CC=C3N=C(NC=3C=CC(=CC=3)C(=O)NC=3C(=CC=CC=3C)C)N=2)=C1 LWMLQGPYZGOEBL-UHFFFAOYSA-N 0.000 claims 1
• LIBYVTUKKMUDQG-UHFFFAOYSA-N 4-[(4-cyclohexylquinazolin-2-yl)amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C2CCCCC2)=C(C=CC=C2)C2=N1 LIBYVTUKKMUDQG-UHFFFAOYSA-N 0.000 claims 1
• BDBSUESQZJUWIW-UHFFFAOYSA-N 4-[(4-cyclopropylquinazolin-2-yl)amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C2CC2)=C(C=CC=C2)C2=N1 BDBSUESQZJUWIW-UHFFFAOYSA-N 0.000 claims 1
• ULOKRBOEKDPTPV-UHFFFAOYSA-N 4-[(4-cyclopropylquinazolin-2-yl)amino]-n-[2-methyl-5-(morpholin-4-ylmethyl)phenyl]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C4CC4)N=3)=CC=2)C(C)=CC=C1CN1CCOCC1 ULOKRBOEKDPTPV-UHFFFAOYSA-N 0.000 claims 1
• YWBGQMKNURJGNY-UHFFFAOYSA-N 4-[(4-ethylquinazolin-2-yl)amino]-n-[2-methyl-5-(morpholin-4-ylmethyl)phenyl]benzamide Chemical compound N=1C2=CC=CC=C2C(CC)=NC=1NC(C=C1)=CC=C1C(=O)NC(C(=CC=1)C)=CC=1CN1CCOCC1 YWBGQMKNURJGNY-UHFFFAOYSA-N 0.000 claims 1
• ZAFOSXDWAXJBFW-UHFFFAOYSA-N 4-[(4-phenylquinazolin-2-yl)amino]-n-(1,2,3,4-tetrahydroisoquinolin-7-yl)benzamide Chemical compound C=1C=C2CCNCC2=CC=1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 ZAFOSXDWAXJBFW-UHFFFAOYSA-N 0.000 claims 1
• IEZXLMDIDXLUDX-UHFFFAOYSA-N 4-[(4-phenylquinazolin-2-yl)amino]-n-(2,3,3-trimethyl-1,4-dihydroisoquinolin-7-yl)benzamide Chemical compound C=1C=C2CC(C)(C)N(C)CC2=CC=1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 IEZXLMDIDXLUDX-UHFFFAOYSA-N 0.000 claims 1
• PLPAGVXKDBSLOM-UHFFFAOYSA-N 4-[(6-benzyl-4-phenyl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl)amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=2C=CC=CC=2)=NC2=C1CN(CC=1C=CC=CC=1)CC2 PLPAGVXKDBSLOM-UHFFFAOYSA-N 0.000 claims 1
• BOTCSLWADXPEJJ-UHFFFAOYSA-N 4-[(6-chloro-4-phenylquinazolin-2-yl)amino]-n-(2-morpholin-4-ylphenyl)benzamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N=C1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N1CCOCC1 BOTCSLWADXPEJJ-UHFFFAOYSA-N 0.000 claims 1
• LVNOAPFUAQZRQM-UHFFFAOYSA-N 4-[(6-chloro-4-phenylquinazolin-2-yl)amino]-n-(4-methylpyrrolidin-3-yl)benzamide Chemical compound CC1CNCC1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=C(Cl)C=C2)C2=N1 LVNOAPFUAQZRQM-UHFFFAOYSA-N 0.000 claims 1
• HKGJASNKPBHEER-UHFFFAOYSA-N 4-[(6-chloro-4-phenylquinazolin-2-yl)amino]-n-[2-(morpholin-4-ylmethyl)phenyl]benzamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N=C1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1CN1CCOCC1 HKGJASNKPBHEER-UHFFFAOYSA-N 0.000 claims 1
• BSEPGGRIAATCFT-UHFFFAOYSA-N 4-[(6-chloro-4-phenylquinazolin-2-yl)amino]-n-[2-(pyrrolidin-1-ylmethyl)phenyl]benzamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N=C1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1CN1CCCC1 BSEPGGRIAATCFT-UHFFFAOYSA-N 0.000 claims 1
• OCHJDLAABHUPLN-UHFFFAOYSA-N 4-[(6-chloro-4-phenylquinazolin-2-yl)amino]-n-[3-[(dimethylamino)methyl]phenyl]benzamide Chemical compound CN(C)CC1=CC=CC(NC(=O)C=2C=CC(NC=3N=C4C=CC(Cl)=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 OCHJDLAABHUPLN-UHFFFAOYSA-N 0.000 claims 1
• QZZAWWIOPKODSR-UHFFFAOYSA-N 4-[(6-chloro-4-phenylquinazolin-2-yl)amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC(Cl)=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 QZZAWWIOPKODSR-UHFFFAOYSA-N 0.000 claims 1
• ZBYOEABLKWKFJJ-UHFFFAOYSA-N 4-[(6-chloro-4-phenylquinazolin-2-yl)amino]-n-cyclopropylbenzamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N=C1NC(C=C1)=CC=C1C(=O)NC1CC1 ZBYOEABLKWKFJJ-UHFFFAOYSA-N 0.000 claims 1
• UJMYAPWFJFMELB-UHFFFAOYSA-N 4-[(7-benzyl-4-phenyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=2C=CC=CC=2)=NC2=C1CCN(CC=1C=CC=CC=1)C2 UJMYAPWFJFMELB-UHFFFAOYSA-N 0.000 claims 1
• XQFZHCMYWTTWRF-UHFFFAOYSA-N 4-[2-[4-[(2,6-dimethylphenyl)carbamoyl]anilino]quinazolin-4-yl]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC(=CC=2)C(N)=O)=C(C=CC=C2)C2=N1 XQFZHCMYWTTWRF-UHFFFAOYSA-N 0.000 claims 1
• LIVWRSLWMPOFSZ-UHFFFAOYSA-N 4-[[4-(2,3-dichlorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=C(Cl)C=CC=4)Cl)N=3)=CC=2)=C1 LIVWRSLWMPOFSZ-UHFFFAOYSA-N 0.000 claims 1
• LPOHHCSPAPHMGS-UHFFFAOYSA-N 4-[[4-(2,4-dichlorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=CC(Cl)=CC=4)Cl)N=3)=CC=2)=C1 LPOHHCSPAPHMGS-UHFFFAOYSA-N 0.000 claims 1
• IMXPOXAFXXFFPH-UHFFFAOYSA-N 4-[[4-(2,4-difluorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=CC(F)=CC=4)F)N=3)=CC=2)=C1 IMXPOXAFXXFFPH-UHFFFAOYSA-N 0.000 claims 1
• SOKNUGNTNYXFMK-UHFFFAOYSA-N 4-[[4-(2,5-dichlorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=CC=C(Cl)C=4)Cl)N=3)=CC=2)=C1 SOKNUGNTNYXFMK-UHFFFAOYSA-N 0.000 claims 1
• BTVPDLCWTJMKPF-UHFFFAOYSA-N 4-[[4-(2,6-difluorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=CC=CC=4F)F)N=3)=CC=2)=C1 BTVPDLCWTJMKPF-UHFFFAOYSA-N 0.000 claims 1
• GRKMSJMXZGBOAQ-UHFFFAOYSA-N 4-[[4-(2-bromophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=CC=CC=4)Br)N=3)=CC=2)=C1 GRKMSJMXZGBOAQ-UHFFFAOYSA-N 0.000 claims 1
• ROZSOIKMONYZMZ-UHFFFAOYSA-N 4-[[4-(2-chlorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=CC=CC=4)Cl)N=3)=CC=2)=C1 ROZSOIKMONYZMZ-UHFFFAOYSA-N 0.000 claims 1
• BERKIVZHBBLWKK-UHFFFAOYSA-N 4-[[4-(3,4-dichlorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=C(Cl)C(Cl)=CC=4)N=3)=CC=2)=C1 BERKIVZHBBLWKK-UHFFFAOYSA-N 0.000 claims 1
• SCCOJJAPLYZION-UHFFFAOYSA-N 4-[[4-(3,5-dichlorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=C(Cl)C=C(Cl)C=4)N=3)=CC=2)=C1 SCCOJJAPLYZION-UHFFFAOYSA-N 0.000 claims 1
• XYXBZADWVBHTTJ-UHFFFAOYSA-N 4-[[4-(3,5-difluorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=C(F)C=C(F)C=4)N=3)=CC=2)=C1 XYXBZADWVBHTTJ-UHFFFAOYSA-N 0.000 claims 1
• BSYBCKFQWPCBQB-UHFFFAOYSA-N 4-[[4-(3,5-dimethyl-1,2-oxazol-4-yl)quinazolin-2-yl]amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound CC1=NOC(C)=C1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 BSYBCKFQWPCBQB-UHFFFAOYSA-N 0.000 claims 1
• XDGGFASCQSRGRY-UHFFFAOYSA-N 4-[[4-(3-bromophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=C(Br)C=CC=4)N=3)=CC=2)=C1 XDGGFASCQSRGRY-UHFFFAOYSA-N 0.000 claims 1
• YWXLRSVVGUDTDV-UHFFFAOYSA-N 4-[[4-(3-chlorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=C(Cl)C=CC=4)N=3)=CC=2)=C1 YWXLRSVVGUDTDV-UHFFFAOYSA-N 0.000 claims 1
• QRGQGYNVGTXUJG-UHFFFAOYSA-N 4-[[4-(4-chlorophenyl)quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC(Cl)=CC=4)N=3)=CC=2)=C1 QRGQGYNVGTXUJG-UHFFFAOYSA-N 0.000 claims 1
• ZEOZBWRNSURZPG-UHFFFAOYSA-N 4-[[4-(4-fluorophenyl)quinazolin-2-yl]amino]-n-[2-methyl-5-(morpholin-4-ylmethyl)phenyl]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC(F)=CC=4)N=3)=CC=2)C(C)=CC=C1CN1CCOCC1 ZEOZBWRNSURZPG-UHFFFAOYSA-N 0.000 claims 1
• LAZWQSPJOCPSMR-UHFFFAOYSA-N 4-[[4-[2-(2-bromophenyl)phenyl]quinazolin-2-yl]amino]-n-[5-[(dimethylamino)methyl]-2-methylphenyl]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=CC=CC=4)C=4C(=CC=CC=4)Br)N=3)=CC=2)=C1 LAZWQSPJOCPSMR-UHFFFAOYSA-N 0.000 claims 1
• KVZMAARHXUJCMN-UHFFFAOYSA-N 4-[[4-[3-[(dimethylamino)methyl]phenyl]quinazolin-2-yl]amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound CN(C)CC1=CC=CC(C=2C3=CC=CC=C3N=C(NC=3C=CC(=CC=3)C(=O)NC=3C(=CC=CC=3C)C)N=2)=C1 KVZMAARHXUJCMN-UHFFFAOYSA-N 0.000 claims 1
• ROXGFAMMWYDFHM-UHFFFAOYSA-N 4-[[4-[4-(dimethylamino)phenyl]quinazolin-2-yl]amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 ROXGFAMMWYDFHM-UHFFFAOYSA-N 0.000 claims 1
• RBDOFLWTMUCABZ-UHFFFAOYSA-N 4-[[4-[4-[(dimethylamino)methyl]phenyl]quinazolin-2-yl]amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 RBDOFLWTMUCABZ-UHFFFAOYSA-N 0.000 claims 1
• ZWGRDEFHHCUTPC-UHFFFAOYSA-N 4-[[4-[4-[3-(dimethylamino)propylamino]phenyl]quinazolin-2-yl]amino]-n-(2,6-dimethylphenyl)benzamide Chemical compound C1=CC(NCCCN(C)C)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 ZWGRDEFHHCUTPC-UHFFFAOYSA-N 0.000 claims 1
• QYWYKIUHIXVOPX-UHFFFAOYSA-N 4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]-n-(2h-tetrazol-5-yl)benzamide Chemical compound CC1=CC=C(C(=O)NC=2NN=NN=2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 QYWYKIUHIXVOPX-UHFFFAOYSA-N 0.000 claims 1
• LDGSWOVXBURIQE-UHFFFAOYSA-N 4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(N)=O)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 LDGSWOVXBURIQE-UHFFFAOYSA-N 0.000 claims 1
• YYQYARCBWCOUOV-UHFFFAOYSA-N 4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 YYQYARCBWCOUOV-UHFFFAOYSA-N 0.000 claims 1
• JHJXIDKCAOPBOF-UHFFFAOYSA-N 4-methyl-n-(2-methyl-1-morpholin-4-ylpropan-2-yl)-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC(C)(C)CN2CCOCC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 JHJXIDKCAOPBOF-UHFFFAOYSA-N 0.000 claims 1
• ZSBRTTAYPGQCOZ-UHFFFAOYSA-N 4-methyl-n-(2-morpholin-4-ylethyl)-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NCCN2CCOCC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 ZSBRTTAYPGQCOZ-UHFFFAOYSA-N 0.000 claims 1
• OOZQACZSHDFDCV-UHFFFAOYSA-N 4-methyl-n-(3-morpholin-4-ylpropyl)-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NCCCN2CCOCC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 OOZQACZSHDFDCV-UHFFFAOYSA-N 0.000 claims 1
• FSKMWVWJHXVJNO-UHFFFAOYSA-N 4-methyl-n-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CN1C(C2)CCC1CC2NC(=O)C(C=1)=CC=C(C)C=1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 FSKMWVWJHXVJNO-UHFFFAOYSA-N 0.000 claims 1
• GDCPFQUYIMYQNG-UHFFFAOYSA-N 5-chloro-n-(2,6-dimethylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]thiophene-2-carboxamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1=CC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)=C(Cl)S1 GDCPFQUYIMYQNG-UHFFFAOYSA-N 0.000 claims 1
• 206010009944 Colon cancer Diseases 0.000 claims 1
• 241000027355 Ferocactus setispinus Species 0.000 claims 1
• 206010060862 Prostate cancer Diseases 0.000 claims 1
• 201000009036 biliary tract cancer Diseases 0.000 claims 1
• 201000008275 breast carcinoma Diseases 0.000 claims 1
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
• UAHTZQXNNCJGQG-UHFFFAOYSA-N methyl 4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzenecarboximidate Chemical compound COC(=N)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 UAHTZQXNNCJGQG-UHFFFAOYSA-N 0.000 claims 1
• QABDLBLINHQPQS-UHFFFAOYSA-N n,n,4-trimethyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CN(C)C(=O)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 QABDLBLINHQPQS-UHFFFAOYSA-N 0.000 claims 1
• WIKYTIJCMHWVCP-UHFFFAOYSA-N n-(2,6-dimethyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C2CN(C)CCC2=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 WIKYTIJCMHWVCP-UHFFFAOYSA-N 0.000 claims 1
• POTKKZLMOHWHIE-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-methyl-4-[(4-phenylquinazolin-2-yl)amino]imidazole-2-carboxamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1=NC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)=CN1C POTKKZLMOHWHIE-UHFFFAOYSA-N 0.000 claims 1
• BBQATBJCIBQRNS-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-(2-morpholin-4-ylethoxy)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C(=C1)OCCN2CCOCC2)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 BBQATBJCIBQRNS-UHFFFAOYSA-N 0.000 claims 1
• LOCIDPDWLYLRHN-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-(4-methylpiperazin-1-yl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1CN(C)CCN1C1=CC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)=CC=C1C(=O)NC1=C(C)C=CC=C1C LOCIDPDWLYLRHN-UHFFFAOYSA-N 0.000 claims 1
• NHAYUSBYURWTLM-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[(1-methylpiperidin-4-yl)amino]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1CN(C)CCC1NC1=CC(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)=CC=C1C(=O)NC1=C(C)C=CC=C1C NHAYUSBYURWTLM-UHFFFAOYSA-N 0.000 claims 1
• VXSQXJKHFBPMGB-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-(2-morpholin-4-ylethoxy)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1OCCN2CCOCC2)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 VXSQXJKHFBPMGB-UHFFFAOYSA-N 0.000 claims 1
• UQPRWJUMIYOPRM-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-methylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C)=C(C=CC=C2)C2=N1 UQPRWJUMIYOPRM-UHFFFAOYSA-N 0.000 claims 1
• GIJMQEGEZXATFV-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-morpholin-4-ylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(N2CCOCC2)=C(C=CC=C2)C2=N1 GIJMQEGEZXATFV-UHFFFAOYSA-N 0.000 claims 1
• HMHLNLASQSJIKK-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=2C=CC=CC=2)=NC2=C1CCNC2 HMHLNLASQSJIKK-UHFFFAOYSA-N 0.000 claims 1
• WXMFJHDPWRXCLV-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=2C=CC=CC=2)=NC2=C1CNCC2 WXMFJHDPWRXCLV-UHFFFAOYSA-N 0.000 claims 1
• MERMDERGCWGOOJ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-phenyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl)amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=2C=CC=CC=2)=NC2=C1CCC2 MERMDERGCWGOOJ-UHFFFAOYSA-N 0.000 claims 1
• TXSXINTUVJDFKS-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-phenylpyrido[2,3-d]pyrimidin-2-yl)amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=N2)C2=N1 TXSXINTUVJDFKS-UHFFFAOYSA-N 0.000 claims 1
• QIARDPWWNLKVDW-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]-2-(2-pyrrolidin-1-ylethoxy)benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C(=C1)OCCN2CCCC2)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 QIARDPWWNLKVDW-UHFFFAOYSA-N 0.000 claims 1
• VKMISIDEIGIQTF-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]-3-(2-pyrrolidin-1-ylethoxy)benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1OCCN2CCCC2)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 VKMISIDEIGIQTF-UHFFFAOYSA-N 0.000 claims 1
• KABICBHONCGBFO-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[(4-propan-2-ylquinazolin-2-yl)amino]benzamide Chemical compound N=1C2=CC=CC=C2C(C(C)C)=NC=1NC(C=C1)=CC=C1C(=O)NC1=C(C)C=CC=C1C KABICBHONCGBFO-UHFFFAOYSA-N 0.000 claims 1
• YEIXZODJZCQCOA-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-(1-methylpiperidin-4-yl)quinazolin-2-yl]amino]benzamide Chemical compound C1CN(C)CCC1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 YEIXZODJZCQCOA-UHFFFAOYSA-N 0.000 claims 1
• LDXCWDBUYKBXGF-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-(1-methylpyrazol-4-yl)quinazolin-2-yl]amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C2=CN(C)N=C2)=C(C=CC=C2)C2=N1 LDXCWDBUYKBXGF-UHFFFAOYSA-N 0.000 claims 1
• RYKCDTVNVSFOPE-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-(1h-indol-5-yl)quinazolin-2-yl]amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=C3C=CNC3=CC=2)=C(C=CC=C2)C2=N1 RYKCDTVNVSFOPE-UHFFFAOYSA-N 0.000 claims 1
• VBQSJLVVINEONW-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-(1h-pyrazol-4-yl)quinazolin-2-yl]amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C2=CNN=C2)=C(C=CC=C2)C2=N1 VBQSJLVVINEONW-UHFFFAOYSA-N 0.000 claims 1
• RTPTZFVGABNTGV-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-(furan-3-yl)quinazolin-2-yl]amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C2=COC=C2)=C(C=CC=C2)C2=N1 RTPTZFVGABNTGV-UHFFFAOYSA-N 0.000 claims 1
• BMZWINXBBPROJD-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-[3-(morpholin-4-ylmethyl)phenyl]quinazolin-2-yl]amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=C(CN3CCOCC3)C=CC=2)=C(C=CC=C2)C2=N1 BMZWINXBBPROJD-UHFFFAOYSA-N 0.000 claims 1
• USJIWFDUHVYNIM-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]quinazolin-2-yl]amino]benzamide Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2C3=CC=CC=C3N=C(NC=3C=CC(=CC=3)C(=O)NC=3C(=CC=CC=3C)C)N=2)=C1 USJIWFDUHVYNIM-UHFFFAOYSA-N 0.000 claims 1
• YQDCSHOUQBHFLM-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-[4-(2-methylpropylamino)phenyl]quinazolin-2-yl]amino]benzamide Chemical compound C1=CC(NCC(C)C)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 YQDCSHOUQBHFLM-UHFFFAOYSA-N 0.000 claims 1
• QUILSPXYKYNTDH-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-[4-(3-ethoxypropylamino)phenyl]quinazolin-2-yl]amino]benzamide Chemical compound C1=CC(NCCCOCC)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 QUILSPXYKYNTDH-UHFFFAOYSA-N 0.000 claims 1
• WDXFZBLZJVGQFL-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-[4-(methylamino)phenyl]quinazolin-2-yl]amino]benzamide Chemical compound C1=CC(NC)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 WDXFZBLZJVGQFL-UHFFFAOYSA-N 0.000 claims 1
• JTTGAFBJKQUEFE-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-[4-(morpholin-4-ylmethyl)phenyl]quinazolin-2-yl]amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC(CN3CCOCC3)=CC=2)=C(C=CC=C2)C2=N1 JTTGAFBJKQUEFE-UHFFFAOYSA-N 0.000 claims 1
• JDZFPMORHGSCKL-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-[4-(propan-2-ylamino)phenyl]quinazolin-2-yl]amino]benzamide Chemical compound C1=CC(NC(C)C)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2C)C)=NC2=CC=CC=C12 JDZFPMORHGSCKL-UHFFFAOYSA-N 0.000 claims 1
• ZHBWNOKXEWCDSD-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[4-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]quinazolin-2-yl]amino]benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C3=CC=CC=C3N=C(NC=3C=CC(=CC=3)C(=O)NC=3C(=CC=CC=3C)C)N=2)C=C1 ZHBWNOKXEWCDSD-UHFFFAOYSA-N 0.000 claims 1
• PGSCSBSMJKQMLQ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-4-[[7-(3-morpholin-4-ylpropoxy)-4-phenylquinazolin-2-yl]amino]benzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC(OCCCN2CCOCC2)=C2)C2=N1 PGSCSBSMJKQMLQ-UHFFFAOYSA-N 0.000 claims 1
• ZFLWMVOIRUWXEO-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(6-chloro-4-phenylquinazolin-2-yl)amino]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=C(Cl)C=C2)C2=N1 ZFLWMVOIRUWXEO-UHFFFAOYSA-N 0.000 claims 1
• YQPHOHGZDJWQRK-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 YQPHOHGZDJWQRK-UHFFFAOYSA-N 0.000 claims 1
• NIKRIEGSZQXILP-UHFFFAOYSA-N n-(2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1N(C)CCC2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 NIKRIEGSZQXILP-UHFFFAOYSA-N 0.000 claims 1
• NIKJMHMVJKTMLN-UHFFFAOYSA-N n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 NIKJMHMVJKTMLN-UHFFFAOYSA-N 0.000 claims 1
• YERMMDUJYCFJRN-UHFFFAOYSA-N n-(2-methyl-4-pyrazol-1-ylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC(N2N=CC=C2)=CC=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 YERMMDUJYCFJRN-UHFFFAOYSA-N 0.000 claims 1
• PTZUFUBSRPZOQD-UHFFFAOYSA-N n-(2-methyl-5-nitrophenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C([N+]([O-])=O)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 PTZUFUBSRPZOQD-UHFFFAOYSA-N 0.000 claims 1
• VVGRUCJJNRISDK-UHFFFAOYSA-N n-(4-imidazol-1-yl-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC(N2C=NC=C2)=CC=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 VVGRUCJJNRISDK-UHFFFAOYSA-N 0.000 claims 1
• ITAVLRAJBVESSW-UHFFFAOYSA-N n-(4-methyl-3,5-dihydro-2h-1,4-benzoxazepin-7-yl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C2CN(C)CCOC2=CC=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 ITAVLRAJBVESSW-UHFFFAOYSA-N 0.000 claims 1
• YSLOWGUVSSSJSD-UHFFFAOYSA-N n-(4-methylpyrrolidin-3-yl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1CNCC1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 YSLOWGUVSSSJSD-UHFFFAOYSA-N 0.000 claims 1
• WCUMSVQNIBQEAE-UHFFFAOYSA-N n-(5-amino-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(N)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 WCUMSVQNIBQEAE-UHFFFAOYSA-N 0.000 claims 1
• YMJXHUCJRHRRBQ-UHFFFAOYSA-N n-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=C(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)C=CC=1C(=O)NC(S1)=NN=C1C1CC1 YMJXHUCJRHRRBQ-UHFFFAOYSA-N 0.000 claims 1
• PSDMJHWSZKFBJG-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=C(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)C=CC=1C(=O)NC(NN=1)=CC=1C1CC1 PSDMJHWSZKFBJG-UHFFFAOYSA-N 0.000 claims 1
• FWEOJCWWBCJRRZ-UHFFFAOYSA-N n-(5-imidazol-1-yl-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(N2C=NC=C2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 FWEOJCWWBCJRRZ-UHFFFAOYSA-N 0.000 claims 1
• WWOIJOPBCXWYJE-UHFFFAOYSA-N n-[2,5-bis(hydroxymethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound OCC1=CC=C(CO)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 WWOIJOPBCXWYJE-UHFFFAOYSA-N 0.000 claims 1
• KQHQHMLMEPXFCR-UHFFFAOYSA-N n-[2-(2-hydroxyethyl)-3,4-dihydro-1h-isoquinolin-5-yl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1N(CCO)CCC2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 KQHQHMLMEPXFCR-UHFFFAOYSA-N 0.000 claims 1
• OTFKGCFEAKXVFD-UHFFFAOYSA-N n-[2-(2-phenylmethoxyethyl)-3,4-dihydro-1h-isoquinolin-5-yl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=C(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)C=CC=1C(=O)NC(C=1CC2)=CC=CC=1CN2CCOCC1=CC=CC=C1 OTFKGCFEAKXVFD-UHFFFAOYSA-N 0.000 claims 1
• IFIDXPPWBVVFMA-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 IFIDXPPWBVVFMA-UHFFFAOYSA-N 0.000 claims 1
• RONFLPDTCHTAAP-UHFFFAOYSA-N n-[2-(hydroxymethyl)-5-(morpholin-4-ylmethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(CO)=CC=C1CN1CCOCC1 RONFLPDTCHTAAP-UHFFFAOYSA-N 0.000 claims 1
• FFVUFBVIFKQIEQ-UHFFFAOYSA-N n-[2-methyl-3-(morpholin-4-ylmethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=CC=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=C1CN1CCOCC1 FFVUFBVIFKQIEQ-UHFFFAOYSA-N 0.000 claims 1
• URQYKPOCUMNXHE-UHFFFAOYSA-N n-[2-methyl-4-(morpholin-4-ylmethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=1CN1CCOCC1 URQYKPOCUMNXHE-UHFFFAOYSA-N 0.000 claims 1
• FEIQPSDIXOHHGM-UHFFFAOYSA-N n-[2-methyl-5-(1-methyltetrazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C=2N(N=NN=2)C)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 FEIQPSDIXOHHGM-UHFFFAOYSA-N 0.000 claims 1
• YTYIXENBFITJDP-UHFFFAOYSA-N n-[2-methyl-5-(1-morpholin-4-ylethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=CC=1C(C)N1CCOCC1 YTYIXENBFITJDP-UHFFFAOYSA-N 0.000 claims 1
• FHEQCYDTGHESFE-UHFFFAOYSA-N n-[2-methyl-5-(1h-1,2,4-triazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C=2NN=CN=2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 FHEQCYDTGHESFE-UHFFFAOYSA-N 0.000 claims 1
• WRMFNSRMXUQETP-UHFFFAOYSA-N n-[2-methyl-5-(1h-pyrazol-4-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C2=CNN=C2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 WRMFNSRMXUQETP-UHFFFAOYSA-N 0.000 claims 1
• JREWIIFAIAKUBD-UHFFFAOYSA-N n-[2-methyl-5-(1h-pyrazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C=2NN=CC=2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 JREWIIFAIAKUBD-UHFFFAOYSA-N 0.000 claims 1
• PJDSZSMIRMUDPC-UHFFFAOYSA-N n-[2-methyl-5-(2-methyltetrazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C2=NN(C)N=N2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 PJDSZSMIRMUDPC-UHFFFAOYSA-N 0.000 claims 1
• SYIXNKNFWDZPAN-UHFFFAOYSA-N n-[2-methyl-5-(2-morpholin-4-ylacetyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)CN2CCOCC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 SYIXNKNFWDZPAN-UHFFFAOYSA-N 0.000 claims 1
• UFHFBIDMNVCTBC-UHFFFAOYSA-N n-[2-methyl-5-(2-morpholin-4-ylethoxy)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1OCCN1CCOCC1 UFHFBIDMNVCTBC-UHFFFAOYSA-N 0.000 claims 1
• RPNREFNNZKDZJB-UHFFFAOYSA-N n-[2-methyl-5-(2h-tetrazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C=2NN=NN=2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 RPNREFNNZKDZJB-UHFFFAOYSA-N 0.000 claims 1
• RCYPZGXYYQYSSI-UHFFFAOYSA-N n-[2-methyl-5-(3-morpholin-4-ylpropoxy)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1OCCCN1CCOCC1 RCYPZGXYYQYSSI-UHFFFAOYSA-N 0.000 claims 1
• GIRUMELIYUNUHU-UHFFFAOYSA-N n-[2-methyl-5-(4-methylpiperazin-1-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1CN(C)CCN1C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 GIRUMELIYUNUHU-UHFFFAOYSA-N 0.000 claims 1
• KLRRGBHZCJLIEL-UHFFFAOYSA-N n-[2-methyl-5-(methylaminomethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CNCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 KLRRGBHZCJLIEL-UHFFFAOYSA-N 0.000 claims 1
• LDRCXCKPEAILRT-UHFFFAOYSA-N n-[2-methyl-5-(morpholin-4-ylmethyl)phenyl]-4-[(4-methylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C)N=3)=CC=2)C(C)=CC=C1CN1CCOCC1 LDRCXCKPEAILRT-UHFFFAOYSA-N 0.000 claims 1
• VWVNEVNBFBKBAS-UHFFFAOYSA-N n-[2-methyl-5-(morpholin-4-ylmethyl)phenyl]-4-[(4-morpholin-4-ylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(N4CCOCC4)N=3)=CC=2)C(C)=CC=C1CN1CCOCC1 VWVNEVNBFBKBAS-UHFFFAOYSA-N 0.000 claims 1
• YDQROWJJXAJHKS-UHFFFAOYSA-N n-[2-methyl-5-(morpholin-4-ylmethyl)phenyl]-4-[(4-phenylpyrido[2,3-d]pyrimidin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4N=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN1CCOCC1 YDQROWJJXAJHKS-UHFFFAOYSA-N 0.000 claims 1
• SNQWXWNQJJRRDI-UHFFFAOYSA-N n-[2-methyl-5-(morpholin-4-ylmethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN1CCOCC1 SNQWXWNQJJRRDI-UHFFFAOYSA-N 0.000 claims 1
• OSIIZSQOBLRTDA-UHFFFAOYSA-N n-[2-methyl-5-(morpholin-4-ylmethyl)phenyl]-4-[(4-propan-2-ylquinazolin-2-yl)amino]benzamide Chemical compound N=1C2=CC=CC=C2C(C(C)C)=NC=1NC(C=C1)=CC=C1C(=O)NC(C(=CC=1)C)=CC=1CN1CCOCC1 OSIIZSQOBLRTDA-UHFFFAOYSA-N 0.000 claims 1
• GKXIZITVQSMXKJ-UHFFFAOYSA-N n-[2-methyl-5-(piperazine-1-carbonyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCNCC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 GKXIZITVQSMXKJ-UHFFFAOYSA-N 0.000 claims 1
• PEOVIIGPGKJNRJ-UHFFFAOYSA-N n-[2-methyl-5-(piperidin-1-ylmethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN1CCCCC1 PEOVIIGPGKJNRJ-UHFFFAOYSA-N 0.000 claims 1
• DSFZWIMNYDFWFW-UHFFFAOYSA-N n-[2-methyl-5-(propylaminomethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCCNCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 DSFZWIMNYDFWFW-UHFFFAOYSA-N 0.000 claims 1
• AONGBJCHPPIXGI-UHFFFAOYSA-N n-[2-methyl-5-(pyrrolidin-1-ylmethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN1CCCC1 AONGBJCHPPIXGI-UHFFFAOYSA-N 0.000 claims 1
• KYSJJKJFMFWNGB-UHFFFAOYSA-N n-[2-methyl-5-[(1-phenylethylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=CC=CC=1C(C)NCC(C=1)=CC=C(C)C=1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 KYSJJKJFMFWNGB-UHFFFAOYSA-N 0.000 claims 1
• MAWMWLZXAGGMNT-UHFFFAOYSA-N n-[2-methyl-5-[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN1C(C)(C)CCCC1(C)C MAWMWLZXAGGMNT-UHFFFAOYSA-N 0.000 claims 1
• VUCSTLLKOKWAJS-UHFFFAOYSA-N n-[2-methyl-5-[(2,4,4-trimethylpentan-2-ylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CNC(C)(C)CC(C)(C)C)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 VUCSTLLKOKWAJS-UHFFFAOYSA-N 0.000 claims 1
• XJOPTFLHWRUCHN-UHFFFAOYSA-N n-[2-methyl-5-[(2-methylpropylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC(C)CNCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 XJOPTFLHWRUCHN-UHFFFAOYSA-N 0.000 claims 1
• RAGLLHVFNRCVJE-UHFFFAOYSA-N n-[2-methyl-5-[(2-morpholin-4-ylacetyl)amino]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1NC(=O)CN1CCOCC1 RAGLLHVFNRCVJE-UHFFFAOYSA-N 0.000 claims 1
• SKVLCMYLZMPQTA-UHFFFAOYSA-N n-[2-methyl-5-[(3-methylbutan-2-ylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC(C)C(C)NCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 SKVLCMYLZMPQTA-UHFFFAOYSA-N 0.000 claims 1
• NYNBCLKVLOSIHL-UHFFFAOYSA-N n-[2-methyl-5-[(4-methylpentan-2-ylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC(C)CC(C)NCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 NYNBCLKVLOSIHL-UHFFFAOYSA-N 0.000 claims 1
• LQPYQJOTHBWXKN-UHFFFAOYSA-N n-[2-methyl-5-[(4-methylpiperazin-1-yl)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 LQPYQJOTHBWXKN-UHFFFAOYSA-N 0.000 claims 1
• FWWJAUAWSDJQBU-PPOKSSTKSA-N n-[2-methyl-5-[(e)-morpholin-4-yliminomethyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1\C=N\N1CCOCC1 FWWJAUAWSDJQBU-PPOKSSTKSA-N 0.000 claims 1
• DPXYLKSVGQNVIT-UHFFFAOYSA-N n-[2-methyl-5-[(propan-2-ylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC(C)NCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 DPXYLKSVGQNVIT-UHFFFAOYSA-N 0.000 claims 1
• UQOBKWDTTGMXQR-UHFFFAOYSA-N n-[2-methyl-5-[2-(2-methylimidazol-1-yl)acetyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=NC=CN1CC(=O)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 UQOBKWDTTGMXQR-UHFFFAOYSA-N 0.000 claims 1
• WJCNATUPJBNCEL-UHFFFAOYSA-N n-[2-methyl-5-[4-(pyridin-3-ylmethyl)piperazine-1-carbonyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCN(CC=3C=NC=CC=3)CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 WJCNATUPJBNCEL-UHFFFAOYSA-N 0.000 claims 1
• OTDVVMFRLOQFPD-UHFFFAOYSA-N n-[2-methyl-5-[4-(pyridin-4-ylmethyl)piperazine-1-carbonyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCN(CC=3C=CN=CC=3)CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 OTDVVMFRLOQFPD-UHFFFAOYSA-N 0.000 claims 1
• NUFHNAPQMVEKSB-UHFFFAOYSA-N n-[2-methyl-5-[4-[(1-methylimidazol-2-yl)methyl]piperazine-1-carbonyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCN(CC=3N(C=CN=3)C)CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 NUFHNAPQMVEKSB-UHFFFAOYSA-N 0.000 claims 1
• DRPTXLNWDABLMT-UHFFFAOYSA-N n-[2-methyl-5-[[methyl(propan-2-yl)amino]methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC(C)N(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 DRPTXLNWDABLMT-UHFFFAOYSA-N 0.000 claims 1
• KGMZVEXWCHZPGE-UHFFFAOYSA-N n-[3-(azepan-1-ylmethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=CC=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=C1CN1CCCCCC1 KGMZVEXWCHZPGE-UHFFFAOYSA-N 0.000 claims 1
• XYMWWSHDNQBJKA-UHFFFAOYSA-N n-[3-(diethylaminomethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCN(CC)CC1=CC=CC(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1C XYMWWSHDNQBJKA-UHFFFAOYSA-N 0.000 claims 1
• DKQDLAQOFYVYSX-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 DKQDLAQOFYVYSX-UHFFFAOYSA-N 0.000 claims 1
• WWYGEUICRXRWNI-UHFFFAOYSA-N n-[3-(morpholin-4-ylmethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=C(NC=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)C=CC=1C(=O)NC(C=1)=CC=CC=1CN1CCOCC1 WWYGEUICRXRWNI-UHFFFAOYSA-N 0.000 claims 1
• OSNIBHGOBXLOPI-UHFFFAOYSA-N n-[3-[(dimethylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC1=CC=CC(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1C OSNIBHGOBXLOPI-UHFFFAOYSA-N 0.000 claims 1
• NNUMAPVWRCYJDV-UHFFFAOYSA-N n-[3-[(dimethylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC1=CC=CC(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 NNUMAPVWRCYJDV-UHFFFAOYSA-N 0.000 claims 1
• LUKCOYJNQANVHH-UHFFFAOYSA-N n-[3-[2-(dimethylamino)ethoxy]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CCOC1=CC=CC(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1C LUKCOYJNQANVHH-UHFFFAOYSA-N 0.000 claims 1
• JPVGACJNIDCWJA-UHFFFAOYSA-N n-[4-(diethylaminomethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC(CN(CC)CC)=CC=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 JPVGACJNIDCWJA-UHFFFAOYSA-N 0.000 claims 1
• IQOXEKPZSCTWRQ-UHFFFAOYSA-N n-[4-[(2-hydroxyethylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC(CNCCO)=CC=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 IQOXEKPZSCTWRQ-UHFFFAOYSA-N 0.000 claims 1
• DJACOSKMIKIWCU-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC(CN(C)C)=CC=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 DJACOSKMIKIWCU-UHFFFAOYSA-N 0.000 claims 1
• XWJBCGPICMVRDJ-UHFFFAOYSA-N n-[4-[[benzyl(methyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=1CN(C)CC1=CC=CC=C1 XWJBCGPICMVRDJ-UHFFFAOYSA-N 0.000 claims 1
• MDAIZJWABQGGRX-UHFFFAOYSA-N n-[4-[[ethyl(2-hydroxyethyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC(CN(CCO)CC)=CC=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 MDAIZJWABQGGRX-UHFFFAOYSA-N 0.000 claims 1
• CHMROFQVUGLEGU-UHFFFAOYSA-N n-[4-[[ethyl(propan-2-yl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC(CN(CC)C(C)C)=CC=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 CHMROFQVUGLEGU-UHFFFAOYSA-N 0.000 claims 1
• ARHBPFMQADPXDZ-UHFFFAOYSA-N n-[5-(2,5-diazabicyclo[2.2.1]heptane-2-carbonyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2C3CC(NC3)C2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 ARHBPFMQADPXDZ-UHFFFAOYSA-N 0.000 claims 1
• FEXORTYBOBXEOL-UHFFFAOYSA-N n-[5-(3,4-dihydro-1h-isoquinolin-2-ylmethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CN2CC3=CC=CC=C3CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 FEXORTYBOBXEOL-UHFFFAOYSA-N 0.000 claims 1
• NDTZJYIHPHSDPN-UHFFFAOYSA-N n-[5-(3,4-dihydro-2h-quinolin-1-ylmethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CN2C3=CC=CC=C3CCC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 NDTZJYIHPHSDPN-UHFFFAOYSA-N 0.000 claims 1
• HOEMTXUMOFRQIB-UHFFFAOYSA-N n-[5-(4-benzylpiperazine-1-carbonyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCN(CC=3C=CC=CC=3)CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 HOEMTXUMOFRQIB-UHFFFAOYSA-N 0.000 claims 1
• QAIAAMADQXGHLI-UHFFFAOYSA-N n-[5-(4-ethylpiperazine-1-carbonyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 QAIAAMADQXGHLI-UHFFFAOYSA-N 0.000 claims 1
• SFUWLBMEXWGHBK-UHFFFAOYSA-N n-[5-(7-azabicyclo[2.2.1]heptan-7-ylmethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CN2C3CCC2CC3)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 SFUWLBMEXWGHBK-UHFFFAOYSA-N 0.000 claims 1
• USQWXDFTGIUMMS-UHFFFAOYSA-N n-[5-(aminomethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CN)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 USQWXDFTGIUMMS-UHFFFAOYSA-N 0.000 claims 1
• HGJYTBNKMXLCRK-UHFFFAOYSA-N n-[5-(azepan-1-ylmethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN1CCCCCC1 HGJYTBNKMXLCRK-UHFFFAOYSA-N 0.000 claims 1
• ASMNILRGTXPIGR-UHFFFAOYSA-N n-[5-(diethylaminomethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCN(CC)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 ASMNILRGTXPIGR-UHFFFAOYSA-N 0.000 claims 1
• QULPVEKQAQFBGQ-UHFFFAOYSA-N n-[5-(ethylaminomethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCNCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 QULPVEKQAQFBGQ-UHFFFAOYSA-N 0.000 claims 1
• PMILYZUSCUQVEW-UHFFFAOYSA-N n-[5-(hydroxymethyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CO)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 PMILYZUSCUQVEW-UHFFFAOYSA-N 0.000 claims 1
• OXMSGIIGGNZDMV-UHFFFAOYSA-N n-[5-(n,n-diethylcarbamimidoyl)-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCN(CC)C(=N)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 OXMSGIIGGNZDMV-UHFFFAOYSA-N 0.000 claims 1
• GQHHTMCZAVVPSD-UHFFFAOYSA-N n-[5-[(1,3-dihydroxypropan-2-ylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CNC(CO)CO)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 GQHHTMCZAVVPSD-UHFFFAOYSA-N 0.000 claims 1
• BWBIVHMGPPJRJN-UHFFFAOYSA-N n-[5-[(2,6-dimethylpiperidin-1-yl)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1CCCC(C)N1CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 BWBIVHMGPPJRJN-UHFFFAOYSA-N 0.000 claims 1
• AQMHKLCIOGULDY-UHFFFAOYSA-N n-[5-[(2-amino-2-methylpropanoyl)amino]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(NC(=O)C(C)(C)N)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 AQMHKLCIOGULDY-UHFFFAOYSA-N 0.000 claims 1
• HEYXAHMCDGBREZ-UHFFFAOYSA-N n-[5-[(2-hydroxyethylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CNCCO)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 HEYXAHMCDGBREZ-UHFFFAOYSA-N 0.000 claims 1
• DKHBYLJXZHOXSO-UHFFFAOYSA-N n-[5-[(2-methoxyethylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound COCCNCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 DKHBYLJXZHOXSO-UHFFFAOYSA-N 0.000 claims 1
• RGVBFDOJJYXXJU-UHFFFAOYSA-N n-[5-[(4-acetylpiperazin-1-yl)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1CN(C(=O)C)CCN1CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 RGVBFDOJJYXXJU-UHFFFAOYSA-N 0.000 claims 1
• OJXUNAMLCPJUBM-UHFFFAOYSA-N n-[5-[(4-benzoylpiperazin-1-yl)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN(CC1)CCN1C(=O)C1=CC=CC=C1 OJXUNAMLCPJUBM-UHFFFAOYSA-N 0.000 claims 1
• KTYSXELTVIWNTR-GDLZYMKVSA-N n-[5-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2C[C@H]3CCCN3CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 KTYSXELTVIWNTR-GDLZYMKVSA-N 0.000 claims 1
• KTYSXELTVIWNTR-LJAQVGFWSA-N n-[5-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2C[C@@H]3CCCN3CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 KTYSXELTVIWNTR-LJAQVGFWSA-N 0.000 claims 1
• QWJKWSFJISONOO-UHFFFAOYSA-N n-[5-[(benzylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CNCC1=CC=CC=C1 QWJKWSFJISONOO-UHFFFAOYSA-N 0.000 claims 1
• OJWWTCDBAORAGZ-UHFFFAOYSA-N n-[5-[(butan-2-ylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCC(C)NCC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 OJWWTCDBAORAGZ-UHFFFAOYSA-N 0.000 claims 1
• MUUQQJCYXFFKIJ-UHFFFAOYSA-N n-[5-[(cyclopentylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CNC1CCCC1 MUUQQJCYXFFKIJ-UHFFFAOYSA-N 0.000 claims 1
• WLVYWYLHJVTAIL-UHFFFAOYSA-N n-[5-[(cyclopropylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CNC1CC1 WLVYWYLHJVTAIL-UHFFFAOYSA-N 0.000 claims 1
• MXCYPBOMBCPTNK-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 MXCYPBOMBCPTNK-UHFFFAOYSA-N 0.000 claims 1
• UCNRPSPLERZSQR-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-4-[(4-propan-2-ylquinazolin-2-yl)amino]benzamide Chemical compound N=1C2=CC=CC=C2C(C(C)C)=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC(CN(C)C)=CC=C1C UCNRPSPLERZSQR-UHFFFAOYSA-N 0.000 claims 1
• YXGKDIIISPMVJD-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-4-[(4-pyridin-2-ylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4N=CC=CC=4)N=3)=CC=2)=C1 YXGKDIIISPMVJD-UHFFFAOYSA-N 0.000 claims 1
• JYTNEEABXBCAJC-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-4-[(4-thiophen-2-ylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4SC=CC=4)N=3)=CC=2)=C1 JYTNEEABXBCAJC-UHFFFAOYSA-N 0.000 claims 1
• FFNGTCFUIXIMOM-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-4-[[4-(1-methylpyrrol-2-yl)quinazolin-2-yl]amino]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4N(C=CC=4)C)N=3)=CC=2)=C1 FFNGTCFUIXIMOM-UHFFFAOYSA-N 0.000 claims 1
• PGUCCZFJGXTXNS-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-4-[[4-(2-fluorophenyl)quinazolin-2-yl]amino]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C(=CC=CC=4)F)N=3)=CC=2)=C1 PGUCCZFJGXTXNS-UHFFFAOYSA-N 0.000 claims 1
• FHHOSLXXKWGBTO-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-4-[[4-(4-fluorophenyl)quinazolin-2-yl]amino]benzamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC(F)=CC=4)N=3)=CC=2)=C1 FHHOSLXXKWGBTO-UHFFFAOYSA-N 0.000 claims 1
• YQNGNJLBSHFLKX-UHFFFAOYSA-N n-[5-[(dimethylamino)methyl]-2-methylphenyl]-5-[(4-phenylquinazolin-2-yl)amino]pyridine-2-carboxamide Chemical compound CN(C)CC1=CC=C(C)C(NC(=O)C=2N=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 YQNGNJLBSHFLKX-UHFFFAOYSA-N 0.000 claims 1
• ZVVYPBJOOCOJIT-UHFFFAOYSA-N n-[5-[(tert-butylamino)methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CNC(C)(C)C)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 ZVVYPBJOOCOJIT-UHFFFAOYSA-N 0.000 claims 1
• RWVKLLAQUGFTJT-UHFFFAOYSA-N n-[5-[1-(dimethylamino)ethyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)C(C)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 RWVKLLAQUGFTJT-UHFFFAOYSA-N 0.000 claims 1
• DFPYAQAEAOTHOA-UHFFFAOYSA-N n-[5-[1-[bis(3,3,3-trifluoropropyl)amino]ethyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound FC(F)(F)CCN(CCC(F)(F)F)C(C)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 DFPYAQAEAOTHOA-UHFFFAOYSA-N 0.000 claims 1
• KSCCVKRYPABLMZ-UHFFFAOYSA-N n-[5-[1-[ethyl(3,3,3-trifluoropropyl)amino]ethyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound FC(F)(F)CCN(CC)C(C)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 KSCCVKRYPABLMZ-UHFFFAOYSA-N 0.000 claims 1
• KJGZQXJCUOSYHL-UHFFFAOYSA-N n-[5-[2-(dimethylamino)ethoxy]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CCOC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 KJGZQXJCUOSYHL-UHFFFAOYSA-N 0.000 claims 1
• FOPUMYXTYSBGDX-UHFFFAOYSA-N n-[5-[2-(dimethylamino)ethylsulfamoyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CCNS(=O)(=O)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 FOPUMYXTYSBGDX-UHFFFAOYSA-N 0.000 claims 1
• YPHGYJUUVKCAPG-UHFFFAOYSA-N n-[5-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCN(CCO)CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 YPHGYJUUVKCAPG-UHFFFAOYSA-N 0.000 claims 1
• QLIVOHBIEJKRPV-UHFFFAOYSA-N n-[5-[4-(cyclopropylmethyl)piperazine-1-carbonyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCN(CC3CC3)CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 QLIVOHBIEJKRPV-UHFFFAOYSA-N 0.000 claims 1
• NSPMHFABTPMNHQ-UHFFFAOYSA-N n-[5-[4-(furan-2-ylmethyl)piperazine-1-carbonyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCN(CC=3OC=CC=3)CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 NSPMHFABTPMNHQ-UHFFFAOYSA-N 0.000 claims 1
• FIMYSEIQVZZRHV-UHFFFAOYSA-N n-[5-[4-[(4-fluorophenyl)methyl]piperazine-1-carbonyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)N2CCN(CC=3C=CC(F)=CC=3)CC2)C=C1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 FIMYSEIQVZZRHV-UHFFFAOYSA-N 0.000 claims 1
• ZOCZPKSIOABOGO-UHFFFAOYSA-N n-[5-[[(1-hydroxy-2-methylpropan-2-yl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CNC(C)(C)CO)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 ZOCZPKSIOABOGO-UHFFFAOYSA-N 0.000 claims 1
• IMEQVQWGTSPUNW-UHFFFAOYSA-N n-[5-[[2-(diethylamino)acetyl]amino]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCN(CC)CC(=O)NC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 IMEQVQWGTSPUNW-UHFFFAOYSA-N 0.000 claims 1
• WJVKMAVLTKOVCZ-UHFFFAOYSA-N n-[5-[[2-(dimethylamino)acetyl]amino]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CN(C)CC(=O)NC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 WJVKMAVLTKOVCZ-UHFFFAOYSA-N 0.000 claims 1
• WGNREIBKBUTPQV-UHFFFAOYSA-N n-[5-[[2-hydroxyethyl(methyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound OCCN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 WGNREIBKBUTPQV-UHFFFAOYSA-N 0.000 claims 1
• DUCCNPAWIOYEBT-UHFFFAOYSA-N n-[5-[[4-(2,2-dimethylpropanoyl)piperazin-1-yl]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN1CCN(C(=O)C(C)(C)C)CC1 DUCCNPAWIOYEBT-UHFFFAOYSA-N 0.000 claims 1
• IZNRLJBHSICBJZ-UHFFFAOYSA-N n-[5-[[4-(cyclopentanecarbonyl)piperazin-1-yl]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN(CC1)CCN1C(=O)C1CCCC1 IZNRLJBHSICBJZ-UHFFFAOYSA-N 0.000 claims 1
• MCEPERZKVFBBAU-UHFFFAOYSA-N n-[5-[[4-(cyclopropanecarbonyl)piperazin-1-yl]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)C(C)=CC=C1CN(CC1)CCN1C(=O)C1CC1 MCEPERZKVFBBAU-UHFFFAOYSA-N 0.000 claims 1
• ASMNKAVXAIEYHP-UHFFFAOYSA-N n-[5-[[benzyl(methyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C=1C=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=CC=1CN(C)CC1=CC=CC=C1 ASMNKAVXAIEYHP-UHFFFAOYSA-N 0.000 claims 1
• CULKOPOEQXFXAF-UHFFFAOYSA-N n-[5-[[benzyl(methyl)amino]methyl]-2-methylphenyl]-4-[(4-propan-2-ylquinazolin-2-yl)amino]benzamide Chemical compound N=1C2=CC=CC=C2C(C(C)C)=NC=1NC(C=C1)=CC=C1C(=O)NC(C(=CC=1)C)=CC=1CN(C)CC1=CC=CC=C1 CULKOPOEQXFXAF-UHFFFAOYSA-N 0.000 claims 1
• QVFXZEPYTNEYRV-UHFFFAOYSA-N n-[5-[[bis(2-hydroxyethyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC1=CC=C(CN(CCO)CCO)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 QVFXZEPYTNEYRV-UHFFFAOYSA-N 0.000 claims 1
• WFRBPRJVTIBEQO-UHFFFAOYSA-N n-[5-[[bis(2-methoxyethyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound COCCN(CCOC)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 WFRBPRJVTIBEQO-UHFFFAOYSA-N 0.000 claims 1
• WZEBOLAOPXUTHP-UHFFFAOYSA-N n-[5-[[cyclohexyl(methyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1CCCCC1N(C)CC(C=1)=CC=C(C)C=1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 WZEBOLAOPXUTHP-UHFFFAOYSA-N 0.000 claims 1
• WJHPFXZFNBJBGS-UHFFFAOYSA-N n-[5-[[cyclopropyl(methyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound C1CC1N(C)CC(C=1)=CC=C(C)C=1NC(=O)C(C=C1)=CC=C1NC(N=C1C=CC=CC1=1)=NC=1C1=CC=CC=C1 WJHPFXZFNBJBGS-UHFFFAOYSA-N 0.000 claims 1
• DARJFFTXAKAKSI-UHFFFAOYSA-N n-[5-[[di(propan-2-yl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CC(C)N(C(C)C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 DARJFFTXAKAKSI-UHFFFAOYSA-N 0.000 claims 1
• KNSBQCJOONDBEV-UHFFFAOYSA-N n-[5-[[ethyl(2,2,2-trifluoroethyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound FC(F)(F)CN(CC)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 KNSBQCJOONDBEV-UHFFFAOYSA-N 0.000 claims 1
• JVPVVOREIIPMFY-UHFFFAOYSA-N n-[5-[[ethyl(2-hydroxyethyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound OCCN(CC)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 JVPVVOREIIPMFY-UHFFFAOYSA-N 0.000 claims 1
• JSPWWAOAPVYARG-UHFFFAOYSA-N n-[5-[[ethyl(methyl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCN(C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 JSPWWAOAPVYARG-UHFFFAOYSA-N 0.000 claims 1
• ODSBCFCOFPWUKD-UHFFFAOYSA-N n-[5-[[ethyl(propan-2-yl)amino]methyl]-2-methylphenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide Chemical compound CCN(C(C)C)CC1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 ODSBCFCOFPWUKD-UHFFFAOYSA-N 0.000 claims 1
• LRQWKRSDCMNBOS-UHFFFAOYSA-N n-hydroxy-4-methyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NO)C=C1NC(=O)C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 LRQWKRSDCMNBOS-UHFFFAOYSA-N 0.000 claims 1
• RBLOJETWIAVFPB-UHFFFAOYSA-N n-methoxy-n,4-dimethyl-3-[[4-[(4-phenylquinazolin-2-yl)amino]benzoyl]amino]benzamide Chemical compound CON(C)C(=O)C1=CC=C(C)C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=C(C=4C=CC=CC=4)N=3)=CC=2)=C1 RBLOJETWIAVFPB-UHFFFAOYSA-N 0.000 claims 1
• 201000002528 pancreatic cancer Diseases 0.000 claims 1
• 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 423
• 239000000543 intermediate Substances 0.000 description 113
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 108
• 125000005843 halogen group Chemical group 0.000 description 102
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 58
• 239000002904 solvent Substances 0.000 description 53
• 125000003944 tolyl group Chemical group 0.000 description 38
• 125000003118 aryl group Chemical group 0.000 description 32
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 31
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
• 239000002585 base Substances 0.000 description 25
• 125000004076 pyridyl group Chemical group 0.000 description 25
• 239000000243 solution Substances 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• 239000007787 solid Substances 0.000 description 16
• 125000003342 alkenyl group Chemical group 0.000 description 14
• 244000060234 Gmelina philippensis Species 0.000 description 13
• 239000003795 chemical substances by application Substances 0.000 description 13
• 239000011541 reaction mixture Substances 0.000 description 13
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
• 239000000651 prodrug Substances 0.000 description 11
• 229940002612 prodrug Drugs 0.000 description 11
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 10
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
• 239000007821 HATU Substances 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 10
• 235000019441 ethanol Nutrition 0.000 description 10
• 239000008194 pharmaceutical composition Substances 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
• 125000000304 alkynyl group Chemical group 0.000 description 9
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
• 239000012320 chlorinating reagent Substances 0.000 description 9
• 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 9
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 208000009956 adenocarcinoma Diseases 0.000 description 8
• 125000003302 alkenyloxy group Chemical group 0.000 description 8
• 125000003710 aryl alkyl group Chemical group 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
• 125000004122 cyclic group Chemical group 0.000 description 8
• 208000035475 disorder Diseases 0.000 description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 125000003226 pyrazolyl group Chemical group 0.000 description 8
• 208000011580 syndromic disease Diseases 0.000 description 8
• 125000001544 thienyl group Chemical group 0.000 description 8
• 206010025323 Lymphomas Diseases 0.000 description 7
• 206010039491 Sarcoma Diseases 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 238000006243 chemical reaction Methods 0.000 description 7
• 125000002541 furyl group Chemical group 0.000 description 7
• 125000002757 morpholinyl group Chemical group 0.000 description 7
• 125000002971 oxazolyl group Chemical group 0.000 description 7
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 125000000168 pyrrolyl group Chemical group 0.000 description 7
• 150000003254 radicals Chemical class 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 125000006413 ring segment Chemical group 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 6
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 6
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
• 150000001204 N-oxides Chemical class 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 150000001408 amides Chemical group 0.000 description 6
• 125000002619 bicyclic group Chemical group 0.000 description 6
• 239000007822 coupling agent Substances 0.000 description 6
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 6
• 125000004188 dichlorophenyl group Chemical group 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 6
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 6
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
• TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical group OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 6
• FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
• 229960004889 salicylic acid Drugs 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
• 238000011282 treatment Methods 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 201000009030 Carcinoma Diseases 0.000 description 5
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
• YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 230000037396 body weight Effects 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 238000002512 chemotherapy Methods 0.000 description 5
• 239000002552 dosage form Substances 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 239000002207 metabolite Substances 0.000 description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 description 5
• 125000004193 piperazinyl group Chemical group 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 235000018102 proteins Nutrition 0.000 description 5
• 206010041823 squamous cell carcinoma Diseases 0.000 description 5
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
• 239000005711 Benzoic acid Substances 0.000 description 4
• 101150041968 CDC13 gene Proteins 0.000 description 4
• 239000004215 Carbon black (E152) Substances 0.000 description 4
• 206010024612 Lipoma Diseases 0.000 description 4
• 241001465754 Metazoa Species 0.000 description 4
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 4
• 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 4
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
• 235000010233 benzoic acid Nutrition 0.000 description 4
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
• 150000003857 carboxamides Chemical class 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 125000001309 chloro group Chemical group Cl* 0.000 description 4
• 235000015165 citric acid Nutrition 0.000 description 4
• 238000007796 conventional method Methods 0.000 description 4
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
• 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
• 239000003814 drug Substances 0.000 description 4
• 125000001153 fluoro group Chemical group F* 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 235000011187 glycerol Nutrition 0.000 description 4
• 229930195733 hydrocarbon Natural products 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 4
• 125000002950 monocyclic group Chemical group 0.000 description 4
• 239000002245 particle Substances 0.000 description 4
• 239000006187 pill Substances 0.000 description 4
• 229920001223 polyethylene glycol Polymers 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 102200084288 rs375181336 Human genes 0.000 description 4
• 102220171501 rs541476418 Human genes 0.000 description 4
• 125000004426 substituted alkynyl group Chemical group 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
• 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 3
• 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 3
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
• SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 3
• UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical group C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 3
• XLZYKTYMLBOINK-UHFFFAOYSA-N 3-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC(O)=CC=2)=C1 XLZYKTYMLBOINK-UHFFFAOYSA-N 0.000 description 3
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
• ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 3
• GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 description 3
• RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 3
• FHUBTSLLILWICW-UHFFFAOYSA-N 4-phenyl-1h-quinazolin-2-one Chemical compound C12=CC=CC=C2NC(=O)N=C1C1=CC=CC=C1 FHUBTSLLILWICW-UHFFFAOYSA-N 0.000 description 3
• VEFDQCSIVBIYFQ-UHFFFAOYSA-N 4-phenylquinazoline Chemical compound C1=CC=CC=C1C1=NC=NC2=CC=CC=C12 VEFDQCSIVBIYFQ-UHFFFAOYSA-N 0.000 description 3
• WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Chemical group OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 3
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
• 201000008808 Fibrosarcoma Diseases 0.000 description 3
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Chemical group OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical group OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
• TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Chemical group OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 3
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
• 108700020796 Oncogene Proteins 0.000 description 3
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
• 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 3
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
• 229920002472 Starch Polymers 0.000 description 3
• 235000021355 Stearic acid Nutrition 0.000 description 3
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
• 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 3
• BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 3
• 206010043276 Teratoma Diseases 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 239000013543 active substance Substances 0.000 description 3
• 125000005090 alkenylcarbonyl group Chemical group 0.000 description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 3
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
• 229940092714 benzenesulfonic acid Drugs 0.000 description 3
• GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 3
• 230000036983 biotransformation Effects 0.000 description 3
• 210000000481 breast Anatomy 0.000 description 3
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 239000004202 carbamide Substances 0.000 description 3
• 150000001721 carbon Chemical group 0.000 description 3
• 230000001413 cellular effect Effects 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• 235000013985 cinnamic acid Nutrition 0.000 description 3
• 229930016911 cinnamic acid Natural products 0.000 description 3
• 238000003776 cleavage reaction Methods 0.000 description 3
• 238000002425 crystallisation Methods 0.000 description 3
• 230000008025 crystallization Effects 0.000 description 3
• 125000004966 cyanoalkyl group Chemical group 0.000 description 3
• 238000011161 development Methods 0.000 description 3
• 230000018109 developmental process Effects 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical group CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 3
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 3
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 3
• 206010016629 fibroma Diseases 0.000 description 3
• 238000003818 flash chromatography Methods 0.000 description 3
• 239000001530 fumaric acid Substances 0.000 description 3
• 235000011087 fumaric acid Nutrition 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 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 3
• 229960005277 gemcitabine Drugs 0.000 description 3
• 239000000174 gluconic acid Chemical group 0.000 description 3
• 235000012208 gluconic acid Nutrition 0.000 description 3
• 239000004220 glutamic acid Chemical group 0.000 description 3
• 235000013922 glutamic acid Nutrition 0.000 description 3
• 229910052736 halogen Inorganic materials 0.000 description 3
• 201000011066 hemangioma Diseases 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• 150000004677 hydrates Chemical class 0.000 description 3
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 239000004310 lactic acid Substances 0.000 description 3
• 235000014655 lactic acid Nutrition 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
• 239000011976 maleic acid Substances 0.000 description 3
• 229960002510 mandelic acid Drugs 0.000 description 3
• 229940098779 methanesulfonic acid Drugs 0.000 description 3
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 229910017604 nitric acid Inorganic materials 0.000 description 3
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 235000019198 oils Nutrition 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 235000005985 organic acids Nutrition 0.000 description 3
• 239000012044 organic layer Substances 0.000 description 3
• 235000006408 oxalic acid Nutrition 0.000 description 3
• 125000004043 oxo group Chemical group O=* 0.000 description 3
• 210000000496 pancreas Anatomy 0.000 description 3
• 230000000144 pharmacologic effect Effects 0.000 description 3
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 3
• 235000019260 propionic acid Nutrition 0.000 description 3
• 210000002307 prostate Anatomy 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• 229940107700 pyruvic acid Drugs 0.000 description 3
• CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 description 3
• 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 description 3
• 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 3
• 230000009467 reduction Effects 0.000 description 3
• 238000006722 reduction reaction Methods 0.000 description 3
• 230000007017 scission Effects 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 239000007909 solid dosage form Substances 0.000 description 3
• 235000019698 starch Nutrition 0.000 description 3
• 239000008117 stearic acid Chemical group 0.000 description 3
• 125000001424 substituent group Chemical group 0.000 description 3
• 125000005017 substituted alkenyl group Chemical group 0.000 description 3
• 125000000547 substituted alkyl group Chemical group 0.000 description 3
• 125000003107 substituted aryl group Chemical group 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• 239000000829 suppository Substances 0.000 description 3
• 208000024891 symptom Diseases 0.000 description 3
• 239000011975 tartaric acid Substances 0.000 description 3
• 235000002906 tartaric acid Nutrition 0.000 description 3
• 229960004964 temozolomide Drugs 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
• 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
• ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• QJJRVFAVKDCJBV-UHFFFAOYSA-N 4-phenyl-n-piperidin-4-ylquinazolin-2-amine Chemical compound C1CNCCC1NC1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 QJJRVFAVKDCJBV-UHFFFAOYSA-N 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• 201000003076 Angiosarcoma Diseases 0.000 description 2
• 208000003174 Brain Neoplasms Diseases 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 241000206672 Gelidium Species 0.000 description 2
• 208000032612 Glial tumor Diseases 0.000 description 2
• 206010018338 Glioma Diseases 0.000 description 2
• 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 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• 208000001258 Hemangiosarcoma Diseases 0.000 description 2
• 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 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
• 208000018142 Leiomyosarcoma Diseases 0.000 description 2
• 206010027476 Metastases Diseases 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
• 229910003827 NRaRb Inorganic materials 0.000 description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
• 229930006000 Sucrose Natural products 0.000 description 2
• 208000008383 Wilms tumor Diseases 0.000 description 2
• 230000001594 aberrant effect Effects 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 239000008186 active pharmaceutical agent Substances 0.000 description 2
• 125000002252 acyl group Chemical group 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 235000010419 agar Nutrition 0.000 description 2
• 125000003158 alcohol group Chemical group 0.000 description 2
• 125000005193 alkenylcarbonyloxy group Chemical group 0.000 description 2
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 2
• 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 description 2
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 description 2
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 2
• 125000002947 alkylene group Chemical group 0.000 description 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
• 239000002246 antineoplastic agent Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 238000003556 assay Methods 0.000 description 2
• 239000012298 atmosphere Substances 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 235000012216 bentonite Nutrition 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
• 210000004556 brain Anatomy 0.000 description 2
• 125000001246 bromo group Chemical group Br* 0.000 description 2
• 210000004899 c-terminal region Anatomy 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• 229960001948 caffeine Drugs 0.000 description 2
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 231100000504 carcinogenesis Toxicity 0.000 description 2
• 208000002458 carcinoid tumor Diseases 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical group C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
• 229960001231 choline Drugs 0.000 description 2
• 238000000576 coating method Methods 0.000 description 2
• 238000004440 column chromatography Methods 0.000 description 2
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
• 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 description 2
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 2
• 235000005911 diet Nutrition 0.000 description 2
• 230000037213 diet Effects 0.000 description 2
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
• 125000004212 difluorophenyl group Chemical group 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• 238000009510 drug design Methods 0.000 description 2
• 229940088679 drug related substance Drugs 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
• 239000000284 extract Substances 0.000 description 2
• 125000001207 fluorophenyl group Chemical group 0.000 description 2
• 210000001035 gastrointestinal tract Anatomy 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 125000004992 haloalkylamino group Chemical group 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
• 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 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
• 125000005191 hydroxyalkylamino group Chemical group 0.000 description 2
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
• 230000006872 improvement Effects 0.000 description 2
• 238000000099 in vitro assay Methods 0.000 description 2
• 125000001041 indolyl group Chemical group 0.000 description 2
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
• 201000010260 leiomyoma Diseases 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 239000008297 liquid dosage form Substances 0.000 description 2
• 230000004777 loss-of-function mutation Effects 0.000 description 2
• 210000004072 lung Anatomy 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 230000036210 malignancy Effects 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 230000002503 metabolic effect Effects 0.000 description 2
• 230000004060 metabolic process Effects 0.000 description 2
• 230000009401 metastasis Effects 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• 239000003607 modifier Substances 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 239000004006 olive oil Substances 0.000 description 2
• 235000008390 olive oil Nutrition 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• 201000008968 osteosarcoma Diseases 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 230000007170 pathology Effects 0.000 description 2
• 229940124531 pharmaceutical excipient Drugs 0.000 description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
• 125000003386 piperidinyl group Chemical group 0.000 description 2
• 229940068917 polyethylene glycols Drugs 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 230000035755 proliferation Effects 0.000 description 2
• 229960004063 propylene glycol Drugs 0.000 description 2
• 235000013772 propylene glycol Nutrition 0.000 description 2
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 2
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 238000004007 reversed phase HPLC Methods 0.000 description 2
• 201000009410 rhabdomyosarcoma Diseases 0.000 description 2
• 229910052701 rubidium Inorganic materials 0.000 description 2
• 230000011664 signaling Effects 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 229940032147 starch Drugs 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 210000000130 stem cell Anatomy 0.000 description 2
• 239000012258 stirred mixture Substances 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
• 230000009466 transformation Effects 0.000 description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
• 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• 238000009736 wetting Methods 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
• ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
• XLOVPKCQAPHUKK-UHFFFAOYSA-N 1,2,3,4,4a,5,8,8a-octahydronaphthalene Chemical compound C1C=CCC2CCCCC21 XLOVPKCQAPHUKK-UHFFFAOYSA-N 0.000 description 1
• 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• 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 1
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
• ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• NMIZONYLXCOHEF-UHFFFAOYSA-N 1h-imidazole-2-carboxamide Chemical compound NC(=O)C1=NC=CN1 NMIZONYLXCOHEF-UHFFFAOYSA-N 0.000 description 1
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
• UZURTQHPMXADGG-UHFFFAOYSA-N 2,3,3a,4,7,7a-hexahydro-1h-indene Chemical compound C1C=CCC2CCCC21 UZURTQHPMXADGG-UHFFFAOYSA-N 0.000 description 1
• PHXGAJLBHUUAKB-UHFFFAOYSA-N 2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound O1CCC2OCCC21 PHXGAJLBHUUAKB-UHFFFAOYSA-N 0.000 description 1
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
• MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
• HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 1
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
• BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
• 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
• 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• BSUOONHBHIRXRO-UHFFFAOYSA-N 2-phenylpyrido[2,3-d]pyrimidine Chemical compound C1=CC=CC=C1C1=NC=C(C=CC=N2)C2=N1 BSUOONHBHIRXRO-UHFFFAOYSA-N 0.000 description 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
• TXPOSODBCCBORG-UHFFFAOYSA-N 4-phenylquinazolin-2-amine Chemical compound C=12C=CC=CC2=NC(N)=NC=1C1=CC=CC=C1 TXPOSODBCCBORG-UHFFFAOYSA-N 0.000 description 1
• 125000005986 4-piperidonyl group Chemical group 0.000 description 1
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
• XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
• SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 235000006491 Acacia senegal Nutrition 0.000 description 1
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
• 206010001233 Adenoma benign Diseases 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
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
• 206010073106 Bone giant cell tumour malignant Diseases 0.000 description 1
• 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 description 1
• 208000005623 Carcinogenesis Diseases 0.000 description 1
• 208000009458 Carcinoma in Situ Diseases 0.000 description 1
• 206010008263 Cervical dysplasia Diseases 0.000 description 1
• 201000005262 Chondroma Diseases 0.000 description 1
• 208000005243 Chondrosarcoma Diseases 0.000 description 1
• 201000009047 Chordoma Diseases 0.000 description 1
• 208000006332 Choriocarcinoma Diseases 0.000 description 1
• 206010048832 Colon adenoma Diseases 0.000 description 1
• 206010010356 Congenital anomaly Diseases 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 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-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-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
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• 206010013710 Drug interaction Diseases 0.000 description 1
• 208000007033 Dysgerminoma Diseases 0.000 description 1
• 208000000471 Dysplastic Nevus Syndrome Diseases 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 201000009051 Embryonal Carcinoma Diseases 0.000 description 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 0.000 description 1
• 206010014967 Ependymoma Diseases 0.000 description 1
• DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 241000206602 Eukaryota Species 0.000 description 1
• 208000006168 Ewing Sarcoma Diseases 0.000 description 1
• 208000007659 Fibroadenoma Diseases 0.000 description 1
• 206010053717 Fibrous histiocytoma Diseases 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• 208000000527 Germinoma Diseases 0.000 description 1
• 208000007569 Giant Cell Tumors Diseases 0.000 description 1
• 201000005409 Gliomatosis cerebri Diseases 0.000 description 1
• 206010018404 Glucagonoma Diseases 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 206010018691 Granuloma Diseases 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 229910004373 HOAc Inorganic materials 0.000 description 1
• 208000002927 Hamartoma Diseases 0.000 description 1
• 102000003693 Hedgehog Proteins Human genes 0.000 description 1
• 108090000031 Hedgehog Proteins Proteins 0.000 description 1
• 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
• 206010019629 Hepatic adenoma Diseases 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 208000005045 Interdigitating dendritic cell sarcoma Diseases 0.000 description 1
• 241000764238 Isis Species 0.000 description 1
• 208000002260 Keloid Diseases 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-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
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 208000002404 Liver Cell Adenoma Diseases 0.000 description 1
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
• 208000014767 Myeloproliferative disease Diseases 0.000 description 1
• KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• 206010029260 Neuroblastoma Diseases 0.000 description 1
• 201000004404 Neurofibroma Diseases 0.000 description 1
• 201000010133 Oligodendroglioma Diseases 0.000 description 1
• 206010031149 Osteitis Diseases 0.000 description 1
• 208000000035 Osteochondroma Diseases 0.000 description 1
• 206010033128 Ovarian cancer Diseases 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 208000007641 Pinealoma Diseases 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
• 108010076504 Protein Sorting Signals Proteins 0.000 description 1
• 101710158727 Protein smoothened Proteins 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 201000000582 Retinoblastoma Diseases 0.000 description 1
• 208000005678 Rhabdomyoma Diseases 0.000 description 1
• 201000010208 Seminoma Diseases 0.000 description 1
• 208000000097 Sertoli-Leydig cell tumor Diseases 0.000 description 1
• 229910008066 SnC12 Inorganic materials 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 241000009298 Trigla lyra Species 0.000 description 1
• 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 description 1
• 208000009311 VIPoma Diseases 0.000 description 1
• 206010048214 Xanthoma Diseases 0.000 description 1
• 206010048215 Xanthomatosis Diseases 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 108010016200 Zinc Finger Protein GLI1 Proteins 0.000 description 1
• 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 239000003655 absorption accelerator Substances 0.000 description 1
• 235000010489 acacia gum Nutrition 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
• 230000003213 activating effect Effects 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000011149 active material Substances 0.000 description 1
• 239000012042 active reagent Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 208000002718 adenomatoid tumor Diseases 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 239000003463 adsorbent Substances 0.000 description 1
• 150000001299 aldehydes Chemical class 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
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229960004050 aminobenzoic acid Drugs 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 238000003782 apoptosis assay Methods 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 238000007080 aromatic substitution reaction Methods 0.000 description 1
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
• 125000005129 aryl carbonyl group Chemical group 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 125000004104 aryloxy group Chemical group 0.000 description 1
• 238000011914 asymmetric synthesis Methods 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 208000001119 benign fibrous histiocytoma Diseases 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 229960004217 benzyl alcohol Drugs 0.000 description 1
• 229960002903 benzyl benzoate Drugs 0.000 description 1
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
• 229960003237 betaine Drugs 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000031018 biological processes and functions Effects 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 230000036760 body temperature Effects 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 208000018339 bone inflammation disease Diseases 0.000 description 1
• 201000009480 botryoid rhabdomyosarcoma Diseases 0.000 description 1
• 201000003149 breast fibroadenoma Diseases 0.000 description 1
• 125000004799 bromophenyl group Chemical group 0.000 description 1
• 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
• 201000002143 bronchus adenoma Diseases 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 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
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 230000036952 cancer formation Effects 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 150000001722 carbon compounds Chemical class 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 150000007942 carboxylates Chemical class 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 235000019438 castor oil Nutrition 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 208000019065 cervical carcinoma Diseases 0.000 description 1
• 210000003679 cervix uteri Anatomy 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 150000005829 chemical entities Chemical class 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 229940044683 chemotherapy drug Drugs 0.000 description 1
• 239000012069 chiral reagent Substances 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 125000000068 chlorophenyl group Chemical group 0.000 description 1
• 208000006990 cholangiocarcinoma Diseases 0.000 description 1
• 235000012000 cholesterol Nutrition 0.000 description 1
• 201000005217 chondroblastoma Diseases 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229960004106 citric acid Drugs 0.000 description 1
• 208000009060 clear cell adenocarcinoma Diseases 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 239000012059 conventional drug carrier Substances 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 238000005859 coupling reaction Methods 0.000 description 1
• 229960001681 croscarmellose sodium Drugs 0.000 description 1
• 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
• 201000010305 cutaneous fibrous histiocytoma Diseases 0.000 description 1
• 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
• UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
• XBILPYQIGZIQEK-UHFFFAOYSA-N cyclohexyl(piperidin-1-yl)methanone Chemical compound C1CCCCN1C(=O)C1CCCCC1 XBILPYQIGZIQEK-UHFFFAOYSA-N 0.000 description 1
• 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000006638 cyclopentyl carbonyl group Chemical group 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
• 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
• 125000005507 decahydroisoquinolyl group Chemical group 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 239000002274 desiccant Substances 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• XOJNEFQLMRCOMS-UHFFFAOYSA-N ditert-butyl(phenyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1 XOJNEFQLMRCOMS-UHFFFAOYSA-N 0.000 description 1
• 238000001647 drug administration Methods 0.000 description 1
• 239000000890 drug combination Substances 0.000 description 1
• 230000008482 dysregulation Effects 0.000 description 1
• 230000013020 embryo development Effects 0.000 description 1
• 201000009409 embryonal rhabdomyosarcoma Diseases 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 150000002081 enamines Chemical class 0.000 description 1
• 201000003914 endometrial carcinoma Diseases 0.000 description 1
• 125000002587 enol group Chemical group 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 210000003238 esophagus Anatomy 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• 229940093499 ethyl acetate Drugs 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
• 229940012017 ethylenediamine Drugs 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 239000003885 eye ointment Substances 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 238000004817 gas chromatography Methods 0.000 description 1
• 238000001030 gas--liquid chromatography Methods 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 description 1
• 201000000052 gastrinoma Diseases 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 201000003115 germ cell cancer Diseases 0.000 description 1
• 229940084910 gliadel Drugs 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 235000001727 glucose Nutrition 0.000 description 1
• YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
• SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 1
• 125000000262 haloalkenyl group Chemical group 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 230000002489 hematologic effect Effects 0.000 description 1
• 208000006359 hepatoblastoma Diseases 0.000 description 1
• 201000002735 hepatocellular adenoma Diseases 0.000 description 1
• 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• 229960002885 histidine Drugs 0.000 description 1
• 239000003906 humectant Substances 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
• 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 125000001841 imino group Chemical group [H]N=* 0.000 description 1
• 201000004933 in situ carcinoma Diseases 0.000 description 1
• 238000005462 in vivo assay Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 239000011261 inert gas Substances 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 206010022498 insulinoma Diseases 0.000 description 1
• 238000012739 integrated shape imaging system Methods 0.000 description 1
• 210000002570 interstitial cell Anatomy 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 230000009545 invasion Effects 0.000 description 1
• 201000010985 invasive ductal carcinoma Diseases 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 229910052742 iron Inorganic materials 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
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 125000003965 isoxazolidinyl group Chemical group 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
• 210000003734 kidney Anatomy 0.000 description 1
• 208000022013 kidney Wilms tumor Diseases 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 206010024627 liposarcoma Diseases 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000008176 lyophilized powder Substances 0.000 description 1
• 229960003646 lysine Drugs 0.000 description 1
• 229920002521 macromolecule Polymers 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 201000004593 malignant giant cell tumor Diseases 0.000 description 1
• 201000000289 malignant teratoma Diseases 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 210000002418 meninge Anatomy 0.000 description 1
• 208000030159 metabolic disease Diseases 0.000 description 1
• 229910021645 metal ion Inorganic materials 0.000 description 1
• TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 230000005012 migration Effects 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 208000010492 mucinous cystadenocarcinoma Diseases 0.000 description 1
• 208000025113 myeloid leukemia Diseases 0.000 description 1
• 208000009091 myxoma Diseases 0.000 description 1
• ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 1
• NSDKDLAEYFSRJC-UHFFFAOYSA-N n-(2-ethylphenyl)benzamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC=CC=C1 NSDKDLAEYFSRJC-UHFFFAOYSA-N 0.000 description 1
• UZPGWRCSQTZJAB-UHFFFAOYSA-N n-(2-fluorophenyl)benzamide Chemical compound FC1=CC=CC=C1NC(=O)C1=CC=CC=C1 UZPGWRCSQTZJAB-UHFFFAOYSA-N 0.000 description 1
• IASIJDXUZOLTAH-UHFFFAOYSA-N n-cyclopropylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CC1 IASIJDXUZOLTAH-UHFFFAOYSA-N 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• AHLKSOXEVRYIRD-UHFFFAOYSA-N n-phenylquinazolin-2-amine Chemical compound N=1C=C2C=CC=CC2=NC=1NC1=CC=CC=C1 AHLKSOXEVRYIRD-UHFFFAOYSA-N 0.000 description 1
• 239000002105 nanoparticle Substances 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 201000008026 nephroblastoma Diseases 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 208000007538 neurilemmoma Diseases 0.000 description 1
• 201000004662 neurofibroma of spinal cord Diseases 0.000 description 1
• 210000002569 neuron Anatomy 0.000 description 1
• 208000004649 neutrophil actin dysfunction Diseases 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 1
• 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
• 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 208000003388 osteoid osteoma Diseases 0.000 description 1
• 208000008798 osteoma Diseases 0.000 description 1
• 229940127084 other anti-cancer agent Drugs 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• 210000003101 oviduct Anatomy 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000005968 oxazolinyl group Chemical group 0.000 description 1
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
• 239000006179 pH buffering agent Substances 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• 208000021255 pancreatic insulinoma Diseases 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1
• 238000002733 pharmacodynamic assay Methods 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
• 125000005545 phthalimidyl group Chemical group 0.000 description 1
• 208000024724 pineal body neoplasm Diseases 0.000 description 1
• 201000004123 pineal gland cancer Diseases 0.000 description 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
• 229920000768 polyamine Polymers 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 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
• WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 150000003140 primary amides Chemical class 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• 230000005522 programmed cell death Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 125000006308 propyl amino group Chemical group 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 238000001959 radiotherapy Methods 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 238000006268 reductive amination reaction Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 208000029922 reticulum cell sarcoma Diseases 0.000 description 1
• 206010039667 schwannoma Diseases 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 208000004548 serous cystadenocarcinoma Diseases 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 210000003625 skull Anatomy 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 229940035044 sorbitan monolaurate Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 238000010183 spectrum analysis Methods 0.000 description 1
• 125000003003 spiro group Chemical group 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 238000000967 suction filtration Methods 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 230000000153 supplemental effect Effects 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 230000004083 survival effect Effects 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 230000009897 systematic effect Effects 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 208000001608 teratocarcinoma Diseases 0.000 description 1
• LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
• 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 210000001550 testis Anatomy 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 229960004559 theobromine Drugs 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000002769 thiazolinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 150000003573 thiols Chemical group 0.000 description 1
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 206010044412 transitional cell carcinoma Diseases 0.000 description 1
• 229940117013 triethanolamine oleate Drugs 0.000 description 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 208000022271 tubular adenoma Diseases 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• 210000003708 urethra Anatomy 0.000 description 1
• 125000005500 uronium group Chemical group 0.000 description 1
• 210000004291 uterus Anatomy 0.000 description 1
• 238000003828 vacuum filtration Methods 0.000 description 1
• 210000001215 vagina Anatomy 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 208000009540 villous adenoma Diseases 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 239000003039 volatile agent Substances 0.000 description 1
• 210000003905 vulva Anatomy 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1