ZA200207110B - 5-Alkylpyrido[2,3-d]pyrimidines tyrosine kinase inhibitors. - Google Patents

Info

Publication number

ZA200207110B

ZA200207110B ZA200207110A ZA200207110A ZA200207110B ZA 200207110 B ZA200207110 B ZA 200207110B ZA 200207110 A ZA200207110 A ZA 200207110A ZA 200207110 A ZA200207110 A ZA 200207110A ZA 200207110 B ZA200207110 B ZA 200207110B

Authority

ZA

South Africa

Prior art keywords

compound

methyl

pyrimidin

pyrido

cyclopentyl

Prior art date

2000-03-06

Links

• Espacenet
• Global Dossier
• Discuss

• 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 2
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 2
• 150000003230 pyrimidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 226
• 125000000217 alkyl group Chemical group 0.000 claims description 86
• -1 trifluoromethylalkyl Chemical group 0.000 claims description 82
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
• 125000003545 alkoxy group Chemical group 0.000 claims description 48
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 150000002367 halogens Chemical class 0.000 claims description 48
• 125000002837 carbocyclic group Chemical group 0.000 claims description 44
• 229910052757 nitrogen Chemical group 0.000 claims description 41
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052717 sulfur Inorganic materials 0.000 claims description 33
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 31
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 30
• 150000002431 hydrogen Chemical group 0.000 claims description 29
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
• 239000001301 oxygen Substances 0.000 claims description 26
• 239000011593 sulfur Chemical group 0.000 claims description 25
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 22
• 150000002825 nitriles Chemical class 0.000 claims description 22
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 229910020008 S(O) Inorganic materials 0.000 claims description 18
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 18
• 229960001171 acetohydroxamic acid Drugs 0.000 claims description 17
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 150000001408 amides Chemical class 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 13
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 12
• 150000002148 esters Chemical class 0.000 claims description 12
• 239000003102 growth factor Substances 0.000 claims description 12
• 230000001404 mediated effect Effects 0.000 claims description 12
• RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• 229940002612 prodrug Drugs 0.000 claims description 11
• 239000000651 prodrug Substances 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• 208000037803 restenosis Diseases 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 8
• 150000001450 anions Chemical class 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• 230000004663 cell proliferation Effects 0.000 claims description 7
• 208000035475 disorder Diseases 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 230000002062 proliferating effect Effects 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
• 108091000080 Phosphotransferase Proteins 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
• 102000020233 phosphotransferase Human genes 0.000 claims description 6
• 101100295741 Gallus gallus COR4 gene Proteins 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 5
• 206010057469 Vascular stenosis Diseases 0.000 claims description 5
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
• 125000005936 piperidyl group Chemical group 0.000 claims description 5
• 230000035755 proliferation Effects 0.000 claims description 5
• 210000004509 vascular smooth muscle cell Anatomy 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 241000700605 Viruses Species 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 238000003745 diagnosis Methods 0.000 claims description 3
• 210000002464 muscle smooth vascular Anatomy 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 239000000203 mixture Substances 0.000 claims 28
• 239000000126 substance Substances 0.000 claims 26
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 9
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 9
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 9
• 239000003814 drug Substances 0.000 claims 7
• 238000004519 manufacturing process Methods 0.000 claims 7
• XDUVRXRABZEPSG-UHFFFAOYSA-N 2-(1-benzofuran-5-ylamino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C4C=COC4=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 XDUVRXRABZEPSG-UHFFFAOYSA-N 0.000 claims 6
• MQMVVICIZXNENP-UHFFFAOYSA-N 8-cyclopentyl-2-(1h-indol-5-ylamino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 MQMVVICIZXNENP-UHFFFAOYSA-N 0.000 claims 6
• 102000018233 Fibroblast Growth Factor Human genes 0.000 claims 6
• 108050007372 Fibroblast Growth Factor Proteins 0.000 claims 6
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 claims 6
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 claims 6
• 229940126864 fibroblast growth factor Drugs 0.000 claims 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 5
• 150000001299 aldehydes Chemical class 0.000 claims 5
• 125000001475 halogen functional group Chemical group 0.000 claims 5
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 4
• LBOFTEHAAWGLCB-UHFFFAOYSA-N 2-[(2-acetyl-1-benzofuran-5-yl)amino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C=C2OC(C(=O)C)=CC2=CC=1NC(N=C12)=NC=C1C(C)=CC(=O)N2C1CCCC1 LBOFTEHAAWGLCB-UHFFFAOYSA-N 0.000 claims 4
• NWFSVKZROQXYRI-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 NWFSVKZROQXYRI-UHFFFAOYSA-N 0.000 claims 4
• DIDKOYSHJAGQQS-UHFFFAOYSA-N 8-cyclohexyl-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=CC(=O)N1C1CCCCC1 DIDKOYSHJAGQQS-UHFFFAOYSA-N 0.000 claims 4
• RMNWLVFFWRBNQK-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 RMNWLVFFWRBNQK-UHFFFAOYSA-N 0.000 claims 4
• ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims 3
• WRFAJWXPENQXQB-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 WRFAJWXPENQXQB-UHFFFAOYSA-N 0.000 claims 3
• JAZAOFQFCQAIQC-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 JAZAOFQFCQAIQC-UHFFFAOYSA-N 0.000 claims 3
• WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 claims 3
• 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims 3
• JJYHQBNSKGWDLY-KRWDZBQOSA-N (2s)-2-amino-3-[4-[(8-cyclopentyl-6-fluoro-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]phenyl]propanoic acid Chemical compound C12=NC(NC=3C=CC(C[C@H](N)C(O)=O)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 JJYHQBNSKGWDLY-KRWDZBQOSA-N 0.000 claims 2
• QCNGGERJGDWDQD-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylanilino)-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCOCC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 QCNGGERJGDWDQD-UHFFFAOYSA-N 0.000 claims 2
• XZYIYZYWEWKEQK-UHFFFAOYSA-N 2-(3-chloro-4-piperazin-1-ylanilino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCNCC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 XZYIYZYWEWKEQK-UHFFFAOYSA-N 0.000 claims 2
• OKJVIDWCJPJGJP-UHFFFAOYSA-N 2-(3-chloro-4-piperazin-1-ylanilino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=C(Cl)C(N4CCNCC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 OKJVIDWCJPJGJP-UHFFFAOYSA-N 0.000 claims 2
• HBKSAUJHTFQTMK-UHFFFAOYSA-N 2-(3-chloro-4-piperazin-1-ylanilino)-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCNCC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 HBKSAUJHTFQTMK-UHFFFAOYSA-N 0.000 claims 2
• PMFXXHFUSDMPRP-UHFFFAOYSA-N 2-(4-fluoro-3-methylanilino)-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(C)C)C2=NC=1NC1=CC=C(F)C(C)=C1 PMFXXHFUSDMPRP-UHFFFAOYSA-N 0.000 claims 2
• FQTDEBGLGLWEQA-UHFFFAOYSA-N 2-(9h-carbazol-3-ylamino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C4C5=CC=CC=C5NC4=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 FQTDEBGLGLWEQA-UHFFFAOYSA-N 0.000 claims 2
• YGPKKACYBUOPFP-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)-3-chloroanilino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=C(Cl)C(N4CC(N)CC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 YGPKKACYBUOPFP-UHFFFAOYSA-N 0.000 claims 2
• VGVLHEVPOLKUTO-UHFFFAOYSA-N 2-[4-(4-acetyl-3,3-dimethylpiperazin-1-yl)anilino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)(C)N(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 VGVLHEVPOLKUTO-UHFFFAOYSA-N 0.000 claims 2
• MUEXYYGLGBJONZ-UHFFFAOYSA-N 2-[4-(4-acetyl-3,3-dimethylpiperazin-1-yl)anilino]-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)(C)N(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(F)C(=O)N2C3CCCC3)C2=N1 MUEXYYGLGBJONZ-UHFFFAOYSA-N 0.000 claims 2
• VEMYILRVAQWCCT-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(F)C(=O)N2C3CCCC3)C2=N1 VEMYILRVAQWCCT-UHFFFAOYSA-N 0.000 claims 2
• DVKBNNLGHOZFCH-UHFFFAOYSA-N 2-anilino-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 DVKBNNLGHOZFCH-UHFFFAOYSA-N 0.000 claims 2
• BRLUAHNVJPJLRS-UHFFFAOYSA-N 5-ethyl-2-(4-piperazin-1-ylanilino)-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(CC)=CC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1N1CCNCC1 BRLUAHNVJPJLRS-UHFFFAOYSA-N 0.000 claims 2
• YABHEJPJDRYFMF-UHFFFAOYSA-N 5-methyl-2-(4-piperazin-1-ylanilino)-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1C=C2C(C)=CC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1N1CCNCC1 YABHEJPJDRYFMF-UHFFFAOYSA-N 0.000 claims 2
• YGNUMNPBRNRSBA-UHFFFAOYSA-N 5-methyl-8-pentan-3-yl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(CC)CC)C2=NC=1NC(C=C1)=CC=C1N1CCNCC1 YGNUMNPBRNRSBA-UHFFFAOYSA-N 0.000 claims 2
• FJTWKJMXWWJNGM-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[4-(3,3,4-trimethylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)(C)N(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(Br)C(=O)N2C3CCCC3)C2=N1 FJTWKJMXWWJNGM-UHFFFAOYSA-N 0.000 claims 2
• IPETVCPCCFDVAD-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[4-(4-methyl-1,4-diazepan-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(Br)C(=O)N2C3CCCC3)C2=N1 IPETVCPCCFDVAD-UHFFFAOYSA-N 0.000 claims 2
• RTFQUOVDUUECBA-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(Br)C(=O)N2C3CCCC3)C2=N1 RTFQUOVDUUECBA-UHFFFAOYSA-N 0.000 claims 2
• MSXZBEHSDIOJQX-UHFFFAOYSA-N 6-chloro-8-cyclopentyl-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(Cl)C(=O)N1C1CCCC1 MSXZBEHSDIOJQX-UHFFFAOYSA-N 0.000 claims 2
• TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 2
• KQIZFKGVLJBJFR-UHFFFAOYSA-N 8-cyclopentyl-2-(1h-indazol-5-ylamino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C4C=NNC4=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 KQIZFKGVLJBJFR-UHFFFAOYSA-N 0.000 claims 2
• UAQYOQLPVWALBE-UHFFFAOYSA-N 8-cyclopentyl-2-(3,4-dichloroanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(Cl)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 UAQYOQLPVWALBE-UHFFFAOYSA-N 0.000 claims 2
• SVAQWRWKZMHRHE-UHFFFAOYSA-N 8-cyclopentyl-2-(4-hydroxy-3,5-dimethylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=C(O)C(C)=CC(NC=2N=C3N(C4CCCC4)C(=O)C=C(C)C3=CN=2)=C1 SVAQWRWKZMHRHE-UHFFFAOYSA-N 0.000 claims 2
• IZCQBCIFVPXHCQ-UHFFFAOYSA-N 8-cyclopentyl-2-(4-piperazin-1-ylanilino)-5-(trifluoromethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C(F)(F)F)=CC(=O)N1C1CCCC1 IZCQBCIFVPXHCQ-UHFFFAOYSA-N 0.000 claims 2
• APNAVIIJIKHXNQ-UHFFFAOYSA-N 8-cyclopentyl-2-[(2,3-dimethyl-1h-indol-5-yl)amino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(N=C12)=NC=C1C(C)=CC(=O)N2C1CCCC1 APNAVIIJIKHXNQ-UHFFFAOYSA-N 0.000 claims 2
• UCRGEQPRUAWQGL-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(1,4-diazepan-1-yl)anilino]-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.C12=NC(NC=3C=CC(=CC=3)N3CCNCCC3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 UCRGEQPRUAWQGL-UHFFFAOYSA-N 0.000 claims 2
• KOHCENFNOCYUTH-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(2-hydroxyethyl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(CCO)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 KOHCENFNOCYUTH-UHFFFAOYSA-N 0.000 claims 2
• NVJIDXANVKQKBS-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(2-hydroxyethylamino)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(NCCO)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 NVJIDXANVKQKBS-UHFFFAOYSA-N 0.000 claims 2
• NTGNTTDNUQRUSW-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(2-methoxyethoxy)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCOC)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 NTGNTTDNUQRUSW-UHFFFAOYSA-N 0.000 claims 2
• KQCSRBKMYHPKNE-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(3,3-dimethylpiperazin-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CC(C)(C)NCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 KQCSRBKMYHPKNE-UHFFFAOYSA-N 0.000 claims 2
• NBQXGCYGWSWENM-HDICACEKSA-N 8-cyclopentyl-2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 NBQXGCYGWSWENM-HDICACEKSA-N 0.000 claims 2
• HVLGMASKQOZOKV-UHFFFAOYSA-N 8-cyclopentyl-2-[4-[4-(3-hydroxypropyl)piperidin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCO)CC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 HVLGMASKQOZOKV-UHFFFAOYSA-N 0.000 claims 2
• FXFIUDXEHWHQFN-UHFFFAOYSA-N 8-cyclopentyl-5-ethyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(CC)=CC(=O)N1C1CCCC1 FXFIUDXEHWHQFN-UHFFFAOYSA-N 0.000 claims 2
• LRSMFTYPNCRAQC-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 LRSMFTYPNCRAQC-UHFFFAOYSA-N 0.000 claims 2
• HPCNYSQWPMYYEH-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-(2h-triazol-4-ylsulfanylmethyl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(CSC4=NNN=C4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 HPCNYSQWPMYYEH-UHFFFAOYSA-N 0.000 claims 2
• MEYPITNZSIAJCW-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-(4-methyl-1,4-diazepan-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 MEYPITNZSIAJCW-UHFFFAOYSA-N 0.000 claims 2
• KROKICGNSBBBTA-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 KROKICGNSBBBTA-UHFFFAOYSA-N 0.000 claims 2
• PTMSMMPWISTCTF-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-[2-(2h-triazol-4-ylsulfanyl)ethyl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(CCSC4=NNN=C4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 PTMSMMPWISTCTF-UHFFFAOYSA-N 0.000 claims 2
• IHXUDADJFMLFMW-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-[3-(1h-1,2,4-triazol-5-ylsulfanyl)pyrrolidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CC(CC3)SC=3NN=CN=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 IHXUDADJFMLFMW-UHFFFAOYSA-N 0.000 claims 2
• RGEVGNHGNXZSOR-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-[3-(2h-triazol-4-ylsulfanyl)pyrrolidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CC(CC3)SC3=NNN=C3)=NC=C2C(C)=CC(=O)N1C1CCCC1 RGEVGNHGNXZSOR-UHFFFAOYSA-N 0.000 claims 2
• VXDMOKSBZKCVKI-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-[4-(1h-1,2,4-triazol-5-ylsulfanyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CC3)SC=3NN=CN=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 VXDMOKSBZKCVKI-UHFFFAOYSA-N 0.000 claims 2
• VAOIKEAHXLZAEU-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-(4-hydroxy-3,5-dimethylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=C(O)C(C)=CC(NC=2N=C3N(C4CCCC4)C(=O)C(F)=C(C)C3=CN=2)=C1 VAOIKEAHXLZAEU-UHFFFAOYSA-N 0.000 claims 2
• WBQACJQSIIUNKB-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-[4-(2-hydroxyethyl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(CCO)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 WBQACJQSIIUNKB-UHFFFAOYSA-N 0.000 claims 2
• GUIYQLKQLJBFIL-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-[4-(2-methoxyethylamino)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(NCCOC)=CC=C1NC1=NC=C(C(C)=C(F)C(=O)N2C3CCCC3)C2=N1 GUIYQLKQLJBFIL-UHFFFAOYSA-N 0.000 claims 2
• RRAUZMBIVYQADH-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-5-methyl-2-[4-(3,3,4-trimethylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)(C)N(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(F)C(=O)N2C3CCCC3)C2=N1 RRAUZMBIVYQADH-UHFFFAOYSA-N 0.000 claims 2
• ULHVYNKVPKBACF-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-5-methyl-2-[4-(4-methyl-1,4-diazepan-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(F)C(=O)N2C3CCCC3)C2=N1 ULHVYNKVPKBACF-UHFFFAOYSA-N 0.000 claims 2
• XDIGYIOQAKKGOG-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(F)C(=O)N2C3CCCC3)C2=N1 XDIGYIOQAKKGOG-UHFFFAOYSA-N 0.000 claims 2
• IWZCMDRLECKMHI-UHFFFAOYSA-N CC1CN(CC(C)N1)c1ccc(Nc2ncc3c(C)c(Cl)c(=O)n(C4CCCC4)c3n2)cc1 Chemical compound CC1CN(CC(C)N1)c1ccc(Nc2ncc3c(C)c(Cl)c(=O)n(C4CCCC4)c3n2)cc1 IWZCMDRLECKMHI-UHFFFAOYSA-N 0.000 claims 2
• ZGYUAHGVIXLJOA-UHFFFAOYSA-N CC1CN(CC(C)N1)c1ccc(Nc2ncc3c(cc(=O)n(C4CCCC4)c3n2)C(F)(F)F)cc1 Chemical compound CC1CN(CC(C)N1)c1ccc(Nc2ncc3c(cc(=O)n(C4CCCC4)c3n2)C(F)(F)F)cc1 ZGYUAHGVIXLJOA-UHFFFAOYSA-N 0.000 claims 2
• 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 2
• 101100533888 Hypocrea jecorina (strain QM6a) sor4 gene Proteins 0.000 claims 2
• 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
• 125000004001 thioalkyl group Chemical group 0.000 claims 2
• ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
• UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
• GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims 1
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims 1
• YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims 1
• VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims 1
• WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
• ABYZSYDGJGVCHS-ZETCQYMHSA-N (2s)-2-acetamido-n-(4-nitrophenyl)propanamide Chemical compound CC(=O)N[C@@H](C)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 ABYZSYDGJGVCHS-ZETCQYMHSA-N 0.000 claims 1
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims 1
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
• FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 claims 1
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
• UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims 1
• OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims 1
• HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims 1
• MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims 1
• OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 claims 1
• YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims 1
• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 claims 1
• OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims 1
• DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims 1
• KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 claims 1
• MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 claims 1
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
• WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims 1
• FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 claims 1
• VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 claims 1
• QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 claims 1
• BJPYBSQNPHNFMK-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylanilino)-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(C)C)C2=NC=1NC(C=C1Cl)=CC=C1N1CCOCC1 BJPYBSQNPHNFMK-UHFFFAOYSA-N 0.000 claims 1
• FSEAJWDJTQNCKC-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylanilino)-8-cyclohexyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCOCC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCCC1 FSEAJWDJTQNCKC-UHFFFAOYSA-N 0.000 claims 1
• RVQOPSIZOKQQQJ-UHFFFAOYSA-N 2-(3-chloro-4-piperazin-1-ylanilino)-8-cyclohexyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCNCC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCCC1 RVQOPSIZOKQQQJ-UHFFFAOYSA-N 0.000 claims 1
• QTMAZYGAVHCKKX-UHFFFAOYSA-N 2-[(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]propane-1,3-diol Chemical compound NC1=NC=NC2=C1C(Br)=CN2COC(CO)CO QTMAZYGAVHCKKX-UHFFFAOYSA-N 0.000 claims 1
• ZMHQYNZUFRWYBH-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)-3-chloroanilino]-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CC(N)CC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 ZMHQYNZUFRWYBH-UHFFFAOYSA-N 0.000 claims 1
• ZRHATDJOALGBMT-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)-3-fluoroanilino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CC(N)CC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 ZRHATDJOALGBMT-UHFFFAOYSA-N 0.000 claims 1
• HKPXHAZGINRUQI-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)anilino]-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1N1CCC(N)C1 HKPXHAZGINRUQI-UHFFFAOYSA-N 0.000 claims 1
• CRUMKUJDWYSRLV-UHFFFAOYSA-N 2-[4-[3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]anilino]-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CC(C(CN)C3)C(F)(F)F)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 CRUMKUJDWYSRLV-UHFFFAOYSA-N 0.000 claims 1
• PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims 1
• FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 claims 1
• PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims 1
• VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims 1
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims 1
• LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 1
• DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 claims 1
• QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
• WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims 1
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims 1
• MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 claims 1
• GVCLNACSYKYUHP-UHFFFAOYSA-N 4-amino-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine-5-carbothioamide Chemical compound C1=NC(N)=C2C(C(=S)N)=CN(COCCO)C2=N1 GVCLNACSYKYUHP-UHFFFAOYSA-N 0.000 claims 1
• GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims 1
• VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 claims 1
• XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 claims 1
• WSFIXAIGIFEPMZ-UHFFFAOYSA-N 5-methyl-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=NC=C2C(C)=CC(=O)NC2=N1 WSFIXAIGIFEPMZ-UHFFFAOYSA-N 0.000 claims 1
• IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 claims 1
• RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 claims 1
• GCMUGFPWXCJFKF-UHFFFAOYSA-N 6-bromo-2-(3-chloro-4-morpholin-4-ylanilino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCOCC4)=CC=3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 GCMUGFPWXCJFKF-UHFFFAOYSA-N 0.000 claims 1
• GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 claims 1
• BXVYIIIRWVJNNI-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-(3-fluoro-4-morpholin-4-ylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCOCC4)=CC=3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 BXVYIIIRWVJNNI-UHFFFAOYSA-N 0.000 claims 1
• JHKFPBYWRHLHJH-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[3-fluoro-4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCC(CCCN5CCOCC5)CC4)=CC=3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 JHKFPBYWRHLHJH-UHFFFAOYSA-N 0.000 claims 1
• BOWHNYMSOQBIQZ-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[4-(1,4-diazepan-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCCC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 BOWHNYMSOQBIQZ-UHFFFAOYSA-N 0.000 claims 1
• KXTCHKYAHFGEOC-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[4-(3,5-dimethylpiperazin-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.C1C(C)NC(C)CN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(Br)C(=O)N2C3CCCC3)C2=N1 KXTCHKYAHFGEOC-UHFFFAOYSA-N 0.000 claims 1
• HGMKBECZLAWUAP-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 HGMKBECZLAWUAP-UHFFFAOYSA-N 0.000 claims 1
• WGHAHMLSCBKLAY-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCN4CCOCC4)CC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 WGHAHMLSCBKLAY-UHFFFAOYSA-N 0.000 claims 1
• NJIAKNWTIVDSDA-FQEVSTJZSA-N 7-[4-(1-methylsulfonylpiperidin-4-yl)phenyl]-n-[[(2s)-morpholin-2-yl]methyl]pyrido[3,4-b]pyrazin-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=CC=C(C=2N=C(NC[C@H]3OCCNC3)C3=NC=CN=C3C=2)C=C1 NJIAKNWTIVDSDA-FQEVSTJZSA-N 0.000 claims 1
• QQUQXPKWFZNPIX-UHFFFAOYSA-N 8-cyclohexyl-2-(4-fluoro-3-methylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(F)C(C)=CC(NC=2N=C3N(C4CCCCC4)C(=O)C=C(C)C3=CN=2)=C1 QQUQXPKWFZNPIX-UHFFFAOYSA-N 0.000 claims 1
• GRFRMCJEAKRJOB-UHFFFAOYSA-N 8-cyclopentyl-2-(3-fluoro-4-morpholin-4-ylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCOCC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 GRFRMCJEAKRJOB-UHFFFAOYSA-N 0.000 claims 1
• FQJIWPYNTJKOGG-UHFFFAOYSA-N 8-cyclopentyl-2-(4-fluoro-3-methylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(F)C(C)=CC(NC=2N=C3N(C4CCCC4)C(=O)C=C(C)C3=CN=2)=C1 FQJIWPYNTJKOGG-UHFFFAOYSA-N 0.000 claims 1
• PLGJGWGEGIDLLL-UHFFFAOYSA-N 8-cyclopentyl-2-(4-fluoroanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(F)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 PLGJGWGEGIDLLL-UHFFFAOYSA-N 0.000 claims 1
• OBFPRRIGMVIJMW-UHFFFAOYSA-N 8-cyclopentyl-2-[3-fluoro-4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCC(CCCN5CCOCC5)CC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 OBFPRRIGMVIJMW-UHFFFAOYSA-N 0.000 claims 1
• PEWUFFDKJRWEEF-UHFFFAOYSA-N 8-cyclopentyl-2-[3-fluoro-4-[4-(3-piperazin-1-ylpropyl)piperidin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCC(CCCN5CCNCC5)CC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 PEWUFFDKJRWEEF-UHFFFAOYSA-N 0.000 claims 1
• PIHGRAZSVAZLER-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(3,3-dimethylpiperazin-1-yl)anilino]-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CC(C)(C)NCC3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 PIHGRAZSVAZLER-UHFFFAOYSA-N 0.000 claims 1
• DIOIXWOQGCFLPW-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 DIOIXWOQGCFLPW-UHFFFAOYSA-N 0.000 claims 1
• LXDMIRGXKQLPBP-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(n-pyridin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(N(C=3C=CC=CC=3)C=3C=CN=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 LXDMIRGXKQLPBP-UHFFFAOYSA-N 0.000 claims 1
• CKVPVLIOQUJSJF-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(CC(F)(F)F)CC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 CKVPVLIOQUJSJF-UHFFFAOYSA-N 0.000 claims 1
• OROMIMNQBQPPPG-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCN4CCOCC4)CC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 OROMIMNQBQPPPG-UHFFFAOYSA-N 0.000 claims 1
• KWDVAAVQCVTJMB-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-[4-(3-piperazin-1-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCN4CCNCC4)CC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 KWDVAAVQCVTJMB-UHFFFAOYSA-N 0.000 claims 1
• WGXBYOLLZVPZLI-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-(3-fluoro-4-piperazin-1-ylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCNCC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 WGXBYOLLZVPZLI-UHFFFAOYSA-N 0.000 claims 1
• ZICFXTBHQRUEHN-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-5-methyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 ZICFXTBHQRUEHN-UHFFFAOYSA-N 0.000 claims 1
• XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 claims 1
• IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims 1
• IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 claims 1
• 239000005711 Benzoic acid Substances 0.000 claims 1
• JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 claims 1
• ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 claims 1
• BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 claims 1
• KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 claims 1
• UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 claims 1
• BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 claims 1
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 claims 1
• 206010007134 Candida infections Diseases 0.000 claims 1
• 229940126657 Compound 17 Drugs 0.000 claims 1
• 229940126639 Compound 33 Drugs 0.000 claims 1
• 229940127007 Compound 39 Drugs 0.000 claims 1
• 108010093488 His-His-His-His-His-His Proteins 0.000 claims 1
• 101000995674 Homo sapiens Nutritionally-regulated adipose and cardiac enriched protein homolog Proteins 0.000 claims 1
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 claims 1
• LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 claims 1
• AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 claims 1
• POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 claims 1
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
• QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 claims 1
• 102100034570 Nutritionally-regulated adipose and cardiac enriched protein homolog Human genes 0.000 claims 1
• 241000036848 Porzana carolina Species 0.000 claims 1
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims 1
• SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 claims 1
• DRBWRJPFNOBNIO-KOLCDFICSA-N [(2r)-1-[(2r)-2-(pyridine-4-carbonylamino)propanoyl]pyrrolidin-2-yl]boronic acid Chemical compound N([C@H](C)C(=O)N1[C@@H](CCC1)B(O)O)C(=O)C1=CC=NC=C1 DRBWRJPFNOBNIO-KOLCDFICSA-N 0.000 claims 1
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
• PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims 1
• SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims 1
• QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims 1
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims 1
• 229940125904 compound 1 Drugs 0.000 claims 1
• 229940125773 compound 10 Drugs 0.000 claims 1
• 229940125797 compound 12 Drugs 0.000 claims 1
• 229940126543 compound 14 Drugs 0.000 claims 1
• 229940125758 compound 15 Drugs 0.000 claims 1
• 229940126142 compound 16 Drugs 0.000 claims 1
• 229940125782 compound 2 Drugs 0.000 claims 1
• 229940125810 compound 20 Drugs 0.000 claims 1
• 229940126086 compound 21 Drugs 0.000 claims 1
• 229940126208 compound 22 Drugs 0.000 claims 1
• 229940125833 compound 23 Drugs 0.000 claims 1
• 229940125961 compound 24 Drugs 0.000 claims 1
• 229940125846 compound 25 Drugs 0.000 claims 1
• 229940125851 compound 27 Drugs 0.000 claims 1
• 229940127204 compound 29 Drugs 0.000 claims 1
• 229940126214 compound 3 Drugs 0.000 claims 1
• 229940125877 compound 31 Drugs 0.000 claims 1
• 229940125878 compound 36 Drugs 0.000 claims 1
• 229940125807 compound 37 Drugs 0.000 claims 1
• 229940127573 compound 38 Drugs 0.000 claims 1
• 229940126540 compound 41 Drugs 0.000 claims 1
• 229940125936 compound 42 Drugs 0.000 claims 1
• 229940125844 compound 46 Drugs 0.000 claims 1
• 229940127271 compound 49 Drugs 0.000 claims 1
• 229940125898 compound 5 Drugs 0.000 claims 1
• 229940126545 compound 53 Drugs 0.000 claims 1
• 229940127113 compound 57 Drugs 0.000 claims 1
• 229940125900 compound 59 Drugs 0.000 claims 1
• 229940126179 compound 72 Drugs 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 claims 1
• GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 claims 1
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
• ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 claims 1
• IHCHOVVAJBADAH-UHFFFAOYSA-N n-[2-hydroxy-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1C2=CC(OC)=CC=C2OCC1C(=O)NC(C(=C1)O)=CC=C1C=1C=NNC=1 IHCHOVVAJBADAH-UHFFFAOYSA-N 0.000 claims 1
• YCSBXKMTXDZGCG-UHFFFAOYSA-N n-[4-[(8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]phenyl]-n-methylacetamide Chemical compound C1=CC(N(C(C)=O)C)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 YCSBXKMTXDZGCG-UHFFFAOYSA-N 0.000 claims 1
• YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 claims 1
• LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 claims 1
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 claims 1
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims 1
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
• 229940080818 propionamide Drugs 0.000 claims 1
• FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 claims 1
• KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 claims 1
• 239000000460 chlorine Substances 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 description 4
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 125000005843 halogen group Chemical group 0.000 description 4
• 125000000623 heterocyclic group Chemical group 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• 108091007914 CDKs Proteins 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 125000002252 acyl group Chemical group 0.000 description 3
• 208000009956 adenocarcinoma Diseases 0.000 description 3
• 125000001589 carboacyl group Chemical group 0.000 description 3
• 125000004432 carbon atom Chemical group C* 0.000 description 3
• 101150073031 cdk2 gene Proteins 0.000 description 3
• 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 3
• 229910052731 fluorine Inorganic materials 0.000 description 3
• 239000003112 inhibitor Substances 0.000 description 3
• 230000003389 potentiating effect Effects 0.000 description 3
• 125000000547 substituted alkyl group Chemical group 0.000 description 3
• 125000001054 5 membered carbocyclic group Chemical group 0.000 description 2
• 125000004008 6 membered carbocyclic group Chemical group 0.000 description 2
• 208000024827 Alzheimer disease Diseases 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• 239000004215 Carbon black (E152) Substances 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 206010061218 Inflammation Diseases 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 125000005907 alkyl ester group Chemical group 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
• 210000000481 breast Anatomy 0.000 description 2
• 230000001413 cellular effect Effects 0.000 description 2
• 238000007796 conventional method Methods 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
• 229930195733 hydrocarbon Natural products 0.000 description 2
• 230000004054 inflammatory process Effects 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 230000004770 neurodegeneration Effects 0.000 description 2
• 208000015122 neurodegenerative disease Diseases 0.000 description 2
• 150000002829 nitrogen Chemical class 0.000 description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 description 2
• 210000003800 pharynx Anatomy 0.000 description 2
• 230000001105 regulatory effect Effects 0.000 description 2
• 150000003335 secondary amines Chemical class 0.000 description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• 125000005925 3-methylpentyloxy group Chemical group 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 208000003200 Adenoma Diseases 0.000 description 1
• 206010001233 Adenoma benign Diseases 0.000 description 1
• 206010005003 Bladder cancer Diseases 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 101150012716 CDK1 gene Proteins 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 201000009030 Carcinoma Diseases 0.000 description 1
• 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 description 1
• 208000024172 Cardiovascular disease Diseases 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 102000016736 Cyclin Human genes 0.000 description 1
• 108050006400 Cyclin Proteins 0.000 description 1
• 102000013717 Cyclin-Dependent Kinase 5 Human genes 0.000 description 1
• 108010025454 Cyclin-Dependent Kinase 5 Proteins 0.000 description 1
• 241000450599 DNA viruses Species 0.000 description 1
• 102100030011 Endoribonuclease Human genes 0.000 description 1
• 101710199605 Endoribonuclease Proteins 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 206010073069 Hepatic cancer Diseases 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 206010023347 Keratoacanthoma Diseases 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 206010029260 Neuroblastoma Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 102000001253 Protein Kinase Human genes 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• 201000010208 Seminoma Diseases 0.000 description 1
• 101710113029 Serine/threonine-protein kinase Proteins 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 229940022663 acetate Drugs 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000004414 alkyl thio group Chemical group 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• BIIVYFLTOXDAOV-YVEFUNNKSA-N alvocidib Chemical compound O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O BIIVYFLTOXDAOV-YVEFUNNKSA-N 0.000 description 1
• 229950010817 alvocidib Drugs 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 230000006229 amino acid addition Effects 0.000 description 1
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
• 230000000259 anti-tumor effect Effects 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 201000001531 bladder carcinoma Diseases 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 210000000133 brain stem Anatomy 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 230000032823 cell division Effects 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 210000003679 cervix uteri Anatomy 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 125000005265 dialkylamine group Chemical group 0.000 description 1
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
• POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 241001493065 dsRNA viruses Species 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 210000003238 esophagus Anatomy 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 229930003935 flavonoid Natural products 0.000 description 1
• 150000002215 flavonoids Chemical class 0.000 description 1
• 235000017173 flavonoids Nutrition 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 208000005017 glioblastoma Diseases 0.000 description 1
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
• 125000001183 hydrocarbyl group Chemical group 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 230000000415 inactivating effect Effects 0.000 description 1
• 239000012678 infectious agent Substances 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• JYTUSYBCFIZPBE-AMTLMPIISA-M lactobionate Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-M 0.000 description 1
• 229940099584 lactobionate Drugs 0.000 description 1
• 208000003849 large cell carcinoma Diseases 0.000 description 1
• 210000002429 large intestine Anatomy 0.000 description 1
• 229940070765 laurate Drugs 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 210000000088 lip Anatomy 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 201000002250 liver carcinoma Diseases 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 210000000214 mouth Anatomy 0.000 description 1
• 125000005487 naphthalate group Chemical group 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
• 125000004433 nitrogen atom Chemical group N* 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• GTVPOLSIJWJJNY-UHFFFAOYSA-N olomoucine Chemical compound N1=C(NCCO)N=C2N(C)C=NC2=C1NCC1=CC=CC=C1 GTVPOLSIJWJJNY-UHFFFAOYSA-N 0.000 description 1
• 238000011275 oncology therapy Methods 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• 229940039748 oxalate Drugs 0.000 description 1
• 125000004316 oxathiadiazolyl group Chemical group O1SNN=C1* 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 201000010198 papillary carcinoma Diseases 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000005561 phenanthryl group Chemical group 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 125000005545 phthalimidyl group Chemical group 0.000 description 1
• 125000003367 polycyclic group Chemical group 0.000 description 1
• 229920000570 polyether Polymers 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 108060006633 protein kinase Proteins 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 201000010174 renal carcinoma Diseases 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 210000003491 skin Anatomy 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 206010041823 squamous cell carcinoma Diseases 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 125000005415 substituted alkoxy group Chemical group 0.000 description 1
• 125000004426 substituted alkynyl group Chemical group 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 210000001550 testis Anatomy 0.000 description 1
• QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 210000001685 thyroid gland Anatomy 0.000 description 1
• 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 210000002105 tongue Anatomy 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• 231100000588 tumorigenic Toxicity 0.000 description 1
• 230000000381 tumorigenic effect Effects 0.000 description 1
• 208000010576 undifferentiated carcinoma Diseases 0.000 description 1
• 241001529453 unidentified herpesvirus Species 0.000 description 1
• 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
• 229940070710 valerate Drugs 0.000 description 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1