PL214867B1 - Pochodna pirydoindolonu, sposób jej wytwarzania, srodek farmaceutyczny zawierajacy te pochodna oraz zastosowanie tej pochodnej - Google Patents

Info

Publication number

PL214867B1

PL214867B1 PL376790A PL37679003A PL214867B1 PL 214867 B1 PL214867 B1 PL 214867B1 PL 376790 A PL376790 A PL 376790A PL 37679003 A PL37679003 A PL 37679003A PL 214867 B1 PL214867 B1 PL 214867B1

Authority

PL

Poland

Prior art keywords

ppm

phenyl

compound

formula

nmr

Prior art date

2002-10-23

Links

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• 238000002360 preparation method Methods 0.000 title claims description 28
• YNHGMRWHXVMPEN-UHFFFAOYSA-N pyrrolo[2,3-f]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)C=C3C=CC2=N1 YNHGMRWHXVMPEN-UHFFFAOYSA-N 0.000 title claims description 18
• 230000001225 therapeutic effect Effects 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 231
• -1 (C1-C4)alkanyl Chemical group 0.000 claims abstract description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 49
• 239000001257 hydrogen Substances 0.000 claims abstract description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 28
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
• 150000002367 halogens Chemical class 0.000 claims abstract description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
• 125000001424 substituent group Chemical group 0.000 claims abstract description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 5
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims abstract description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
• 238000000034 method Methods 0.000 claims description 26
• 206010028980 Neoplasm Diseases 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 13
• 238000011282 treatment Methods 0.000 claims description 10
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 8
• 150000002148 esters Chemical class 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
• NDKNXKCTYKUROA-UHFFFAOYSA-N 3-(4-aminophenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=C(N)C=C1 NDKNXKCTYKUROA-UHFFFAOYSA-N 0.000 claims description 4
• WHIUBYFLQYSILN-UHFFFAOYSA-N 3-[3-(hydroxymethyl)phenyl]-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=CC(CO)=C1 WHIUBYFLQYSILN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 238000011321 prophylaxis Methods 0.000 claims description 4
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
• KWNZLDPPJVSTOZ-UHFFFAOYSA-N 3-(1,6-dimethyl-2-oxo-9h-pyrido[2,3-b]indol-3-yl)benzonitrile Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=CC(C#N)=C1 KWNZLDPPJVSTOZ-UHFFFAOYSA-N 0.000 claims description 3
• MHFNCUATIPSVOJ-UHFFFAOYSA-N 3-(3-acetylphenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound CC(=O)C1=CC=CC(C=2C(N(C)C=3NC4=CC=C(C)C=C4C=3C=2)=O)=C1 MHFNCUATIPSVOJ-UHFFFAOYSA-N 0.000 claims description 3
• 230000001394 metastastic effect Effects 0.000 claims description 3
• 206010061289 metastatic neoplasm Diseases 0.000 claims description 3
• OBXBXDREPHLMNM-UHFFFAOYSA-N 1,6-dimethyl-3-[3-(pyridin-2-ylamino)phenyl]-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C(C=1)=CC=CC=1NC1=CC=CC=N1 OBXBXDREPHLMNM-UHFFFAOYSA-N 0.000 claims description 2
• UOPPWPAWPJQPLM-UHFFFAOYSA-N 1,6-dimethyl-3-[3-(pyrimidin-2-ylamino)phenyl]-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C(C=1)=CC=CC=1NC1=NC=CC=N1 UOPPWPAWPJQPLM-UHFFFAOYSA-N 0.000 claims description 2
• BXYOWBPGACEZSO-UHFFFAOYSA-N 1,6-dimethyl-3-[3-(trifluoromethyl)phenyl]-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 BXYOWBPGACEZSO-UHFFFAOYSA-N 0.000 claims description 2
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
• XGALXJUJMUEJPR-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=C(Cl)C=C1Cl XGALXJUJMUEJPR-UHFFFAOYSA-N 0.000 claims description 2
• YVMLHKHLLYTELY-UHFFFAOYSA-N 3-(2,4-dimethoxyphenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound COC1=CC(OC)=CC=C1C(C(N1C)=O)=CC2=C1NC1=CC=C(C)C=C12 YVMLHKHLLYTELY-UHFFFAOYSA-N 0.000 claims description 2
• UOCLWKVLEWVWGN-UHFFFAOYSA-N 3-(2-anilinophenyl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C1=CC=CC=C1NC1=CC=CC=C1 UOCLWKVLEWVWGN-UHFFFAOYSA-N 0.000 claims description 2
• PMWVBWVFGYECTN-UHFFFAOYSA-N 3-(6-chloro-1,3-benzodioxol-5-yl)-1,6-dimethyl-9h-pyrido[2,3-b]indol-2-one Chemical compound C=1C=2C3=CC(C)=CC=C3NC=2N(C)C(=O)C=1C(C(=C1)Cl)=CC2=C1OCO2 PMWVBWVFGYECTN-UHFFFAOYSA-N 0.000 claims description 2
• KJBZXISVZRELEI-UHFFFAOYSA-N 6-bromo-3-(3,5-dimethylphenyl)-1-methyl-9h-pyrido[2,3-b]indol-2-one Chemical compound CC1=CC(C)=CC(C=2C(N(C)C=3NC4=CC=C(Br)C=C4C=3C=2)=O)=C1 KJBZXISVZRELEI-UHFFFAOYSA-N 0.000 claims description 2
• HICQTMQGDQCZEM-UHFFFAOYSA-N C12=CC(C)=CC=C2N2CCCN(C3=O)C2=C1C=C3C1=CC=C(Cl)C=C1Cl Chemical compound C12=CC(C)=CC=C2N2CCCN(C3=O)C2=C1C=C3C1=CC=C(Cl)C=C1Cl HICQTMQGDQCZEM-UHFFFAOYSA-N 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 102100030500 Heparin cofactor 2 Human genes 0.000 claims 1
• 101710153650 Heparin cofactor 2 Proteins 0.000 claims 1
• 230000001093 anti-cancer Effects 0.000 abstract description 4
• 125000005843 halogen group Chemical group 0.000 abstract description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 3
• 125000004414 alkyl thio group Chemical group 0.000 abstract 2
• 125000003396 thiol group Chemical class [H]S* 0.000 abstract 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 270
• 238000005481 NMR spectroscopy Methods 0.000 description 188
• 239000000203 mixture Substances 0.000 description 130
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 108
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 87
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
• 239000000243 solution Substances 0.000 description 65
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 29
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 239000002244 precipitate Substances 0.000 description 24
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 21
• 239000000843 powder Substances 0.000 description 21
• 239000000377 silicon dioxide Substances 0.000 description 21
• 239000012074 organic phase Substances 0.000 description 20
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
• 235000019341 magnesium sulphate Nutrition 0.000 description 18
• 239000003208 petroleum Substances 0.000 description 18
• 229910000104 sodium hydride Inorganic materials 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 125000001246 bromo group Chemical group Br* 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 239000000047 product Substances 0.000 description 13
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
• 238000004440 column chromatography Methods 0.000 description 12
• 238000000746 purification Methods 0.000 description 12
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
• 150000002431 hydrogen Chemical group 0.000 description 7
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
• 235000015320 potassium carbonate Nutrition 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
• ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• 229910019213 POCl3 Inorganic materials 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
• 239000008346 aqueous phase Substances 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• CYGNCRNNVLLDET-UHFFFAOYSA-N methyl 2-(3,5-difluorophenyl)-3-(dimethylamino)prop-2-enoate Chemical compound COC(=O)C(=CN(C)C)C1=CC(F)=CC(F)=C1 CYGNCRNNVLLDET-UHFFFAOYSA-N 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 6
• YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 5
• 230000000259 anti-tumor effect Effects 0.000 description 5
• 229940125844 compound 46 Drugs 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 5
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
• HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 4
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 201000011510 cancer Diseases 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
• 239000002552 dosage form Substances 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 239000007789 gas Substances 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
• HMHWNJGOHUYVMD-UHFFFAOYSA-N (4-methylanilino)azanium;chloride Chemical compound Cl.CC1=CC=C(NN)C=C1 HMHWNJGOHUYVMD-UHFFFAOYSA-N 0.000 description 3
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• 206010006187 Breast cancer Diseases 0.000 description 3
• 208000026310 Breast neoplasm Diseases 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
• 210000004027 cell Anatomy 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
• 238000000605 extraction Methods 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 230000000699 topical effect Effects 0.000 description 3
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