NZ545913A - Quinazoline derivatives - Google Patents

Info

Publication number

NZ545913A

NZ545913A NZ545913A NZ54591304A NZ545913A NZ 545913 A NZ545913 A NZ 545913A NZ 545913 A NZ545913 A NZ 545913A NZ 54591304 A NZ54591304 A NZ 54591304A NZ 545913 A NZ545913 A NZ 545913A

Authority

NZ

New Zealand

Prior art keywords

quinazoline

chloro

piperidin

oxy

methoxy

Prior art date

2003-09-19

Links

• Espacenet
• Global Dossier
• Discuss

• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract description 47
• 150000003839 salts Chemical class 0.000 claims abstract description 74
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 52
• 238000011282 treatment Methods 0.000 claims abstract description 41
• 125000001424 substituent group Chemical group 0.000 claims abstract description 35
• 201000011510 cancer Diseases 0.000 claims abstract description 29
• 238000004519 manufacturing process Methods 0.000 claims abstract description 19
• 239000003814 drug Substances 0.000 claims abstract description 13
• 150000001875 compounds Chemical class 0.000 claims description 198
• -1 cyano, nitro, hydroxy, amino, carboxy, sulfamoyl Chemical group 0.000 claims description 152
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 109
• 238000000034 method Methods 0.000 claims description 106
• 125000000217 alkyl group Chemical group 0.000 claims description 95
• 238000006243 chemical reaction Methods 0.000 claims description 75
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 74
• 230000008569 process Effects 0.000 claims description 71
• 239000001257 hydrogen Substances 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 43
• 125000006239 protecting group Chemical group 0.000 claims description 39
• 125000003545 alkoxy group Chemical group 0.000 claims description 35
• 125000003282 alkyl amino group Chemical group 0.000 claims description 34
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 239000000203 mixture Substances 0.000 claims description 28
• 239000000243 solution Substances 0.000 claims description 28
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 27
• 125000001153 fluoro group Chemical group F* 0.000 claims description 27
• 125000000524 functional group Chemical group 0.000 claims description 27
• 238000002360 preparation method Methods 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 241001465754 Metazoa Species 0.000 claims description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 230000001028 anti-proliverative effect Effects 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 11
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• 238000003776 cleavage reaction Methods 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• YYQGUWHFXVXQOO-GFCCVEGCSA-N 2-chloro-4-[[3-[(2R)-2-hydroxybutyl]-1-methyl-2-oxobenzimidazol-5-yl]amino]pyridine-3-carbonitrile Chemical group ClC1=C(C#N)C(=CC=N1)NC1=CC2=C(N(C(N2C[C@@H](CC)O)=O)C)C=C1 YYQGUWHFXVXQOO-GFCCVEGCSA-N 0.000 claims description 8
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 7
• 125000001589 carboacyl group Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
• 125000004423 acyloxy group Chemical group 0.000 claims description 6
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
• 230000029936 alkylation Effects 0.000 claims description 6
• 238000005804 alkylation reaction Methods 0.000 claims description 6
• 238000005859 coupling reaction Methods 0.000 claims description 6
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 230000007017 scission Effects 0.000 claims description 5
• 239000011593 sulfur Chemical group 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• DFJSJLGUIXFDJP-UHFFFAOYSA-N sapitinib Chemical compound C1CN(CC(=O)NC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(Cl)=C1F DFJSJLGUIXFDJP-UHFFFAOYSA-N 0.000 claims description 4
• 150000003335 secondary amines Chemical class 0.000 claims description 4
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
• QRVGWOQDGHNNOJ-UHFFFAOYSA-N 2-[4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-1-piperazin-1-ylethanone Chemical compound C=12C=C(OC3CCN(CC(=O)N4CCNCC4)CC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F QRVGWOQDGHNNOJ-UHFFFAOYSA-N 0.000 claims description 3
• HJDSISDQNHYQBG-UHFFFAOYSA-N 2-[4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-n,n-dimethylacetamide Chemical compound C=12C=C(OC3CCN(CC(=O)N(C)C)CC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F HJDSISDQNHYQBG-UHFFFAOYSA-N 0.000 claims description 3
• 229910021529 ammonia Inorganic materials 0.000 claims description 3
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 238000006268 reductive amination reaction Methods 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• YAMOXVHULRXADY-UHFFFAOYSA-N 2-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C=12C=C(OC3CCN(CC(=O)N4CCCC4)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 YAMOXVHULRXADY-UHFFFAOYSA-N 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• LJMKDKCKIKTXIO-UHFFFAOYSA-N 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxy-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C=12C=C(OC3CCN(CC3)C(=O)NC(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 LJMKDKCKIKTXIO-UHFFFAOYSA-N 0.000 claims description 2
• 230000008878 coupling Effects 0.000 claims description 2
• 238000010168 coupling process Methods 0.000 claims description 2
• 238000009472 formulation Methods 0.000 claims description 2
• 150000003141 primary amines Chemical class 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 150000003246 quinazolines Chemical class 0.000 claims 41
• SHSMZPYXZURMEE-UHFFFAOYSA-N 2-[4-[4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C=12C=C(OC3CCN(CC(=O)N4CCN(C)CC4)CC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F SHSMZPYXZURMEE-UHFFFAOYSA-N 0.000 claims 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
• 229920002261 Corn starch Polymers 0.000 claims 1
• 229920002785 Croscarmellose sodium Polymers 0.000 claims 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 claims 1
• 235000019759 Maize starch Nutrition 0.000 claims 1
• 241000907681 Morpho Species 0.000 claims 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 claims 1
• 229960001681 croscarmellose sodium Drugs 0.000 claims 1
• 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims 1
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
• 238000002347 injection Methods 0.000 claims 1
• 239000007924 injection Substances 0.000 claims 1
• 239000008101 lactose Substances 0.000 claims 1
• 235000019359 magnesium stearate Nutrition 0.000 claims 1
• 238000002156 mixing Methods 0.000 claims 1
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 1
• 229940068918 polyethylene glycol 400 Drugs 0.000 claims 1
• 239000008215 water for injection Substances 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
• 210000004027 cell Anatomy 0.000 description 44
• 230000000694 effects Effects 0.000 description 28
• 239000002904 solvent Substances 0.000 description 27
• 238000012360 testing method Methods 0.000 description 27
• 239000002585 base Substances 0.000 description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 230000005764 inhibitory process Effects 0.000 description 23
• 238000001819 mass spectrum Methods 0.000 description 23
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 21
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 21
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 21
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
• 239000002953 phosphate buffered saline Substances 0.000 description 18
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 17
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 17
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• 241000282414 Homo sapiens Species 0.000 description 16
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 16
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 16
• 230000035755 proliferation Effects 0.000 description 15
• 210000004881 tumor cell Anatomy 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• 239000012442 inert solvent Substances 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 13
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• 239000003112 inhibitor Substances 0.000 description 13
• 101150041968 CDC13 gene Proteins 0.000 description 12
• 241000699670 Mus sp. Species 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
• 102000001301 EGF receptor Human genes 0.000 description 11
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• 125000003118 aryl group Chemical group 0.000 description 11
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• 239000000047 product Substances 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
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• 108090000623 proteins and genes Proteins 0.000 description 10
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• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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• 125000002252 acyl group Chemical group 0.000 description 9
• 150000001412 amines Chemical class 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
• 230000000259 anti-tumor effect Effects 0.000 description 8
• 239000000010 aprotic solvent Substances 0.000 description 8
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 8
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 102000004169 proteins and genes Human genes 0.000 description 8
• 102000005962 receptors Human genes 0.000 description 8
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
• 238000005481 NMR spectroscopy Methods 0.000 description 7
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
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• DFNJBNWBONZOQL-UHFFFAOYSA-N n-(3-chloro-2-fluorophenyl)-7-methoxy-6-piperidin-4-yloxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCNCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1F DFNJBNWBONZOQL-UHFFFAOYSA-N 0.000 description 7
• 102000020233 phosphotransferase Human genes 0.000 description 7
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 108020003175 receptors Proteins 0.000 description 7
• VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 7
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 6
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• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 6
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