AP976A - Thienopyrimidine and thienopyridine derivatives useful as anticancer agents. - Google Patents

Info

Publication number

AP976A

AP976A APAP/P/1998/001389A AP9801389A AP976A AP 976 A AP976 A AP 976A AP 9801389 A AP9801389 A AP 9801389A AP 976 A AP976 A AP 976A

Authority

AP

ARIPO

Prior art keywords

thieno

phenyl

pyrimidin

amine

ylamino

Prior art date

1997-11-11

Links

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• 239000002246 antineoplastic agent Substances 0.000 title claims description 6
• DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title description 3
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 253
• 150000003839 salts Chemical class 0.000 claims abstract description 41
• 241000124008 Mammalia Species 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 18
• 150000004677 hydrates Chemical class 0.000 claims abstract description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 119
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 98
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 97
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 80
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 77
• -1 trifluoromethyi Chemical group 0.000 claims description 65
• 125000000623 heterocyclic group Chemical group 0.000 claims description 60
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 206010028980 Neoplasm Diseases 0.000 claims description 37
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 150000001412 amines Chemical class 0.000 claims description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 210000004027 cell Anatomy 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 22
• 201000011510 cancer Diseases 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 210000002307 prostate Anatomy 0.000 claims description 14
• 210000000481 breast Anatomy 0.000 claims description 13
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 12
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 210000004072 lung Anatomy 0.000 claims description 11
• 230000002611 ovarian Effects 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 239000003112 inhibitor Substances 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• 150000004985 diamines Chemical class 0.000 claims description 8
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 8
• 102000004190 Enzymes Human genes 0.000 claims description 7
• 108090000790 Enzymes Proteins 0.000 claims description 7
• 230000033115 angiogenesis Effects 0.000 claims description 7
• 210000001072 colon Anatomy 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 230000002496 gastric effect Effects 0.000 claims description 7
• 208000017169 kidney disease Diseases 0.000 claims description 7
• 230000004862 vasculogenesis Effects 0.000 claims description 7
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 6
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 6
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 206010020718 hyperplasia Diseases 0.000 claims description 6
• 238000002513 implantation Methods 0.000 claims description 6
• 229960004063 propylene glycol Drugs 0.000 claims description 6
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 5
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
• 208000032612 Glial tumor Diseases 0.000 claims description 5
• 206010018338 Glioma Diseases 0.000 claims description 5
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 5
• 206010033645 Pancreatitis Diseases 0.000 claims description 5
• 230000000340 anti-metabolite Effects 0.000 claims description 5
• 229940100197 antimetabolite Drugs 0.000 claims description 5
• 239000002256 antimetabolite Substances 0.000 claims description 5
• 210000001109 blastomere Anatomy 0.000 claims description 5
• 210000004556 brain Anatomy 0.000 claims description 5
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 5
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
• 239000003102 growth factor Substances 0.000 claims description 5
• 201000011066 hemangioma Diseases 0.000 claims description 5
• 210000003734 kidney Anatomy 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• GRQDRYCULGMCBY-UHFFFAOYSA-N n-(2-methyl-1,3-benzothiazol-6-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1=C2SC(C)=NC2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 GRQDRYCULGMCBY-UHFFFAOYSA-N 0.000 claims description 5
• 229960003966 nicotinamide Drugs 0.000 claims description 5
• 239000011570 nicotinamide Substances 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• SAGSLTAQOJYUAH-UHFFFAOYSA-N 4-[4-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]anilino]phenol Chemical compound C1=CC(O)=CC=C1NC(C=C1)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 SAGSLTAQOJYUAH-UHFFFAOYSA-N 0.000 claims description 4
• ZMFBDTFWPZMXGY-UHFFFAOYSA-N 4-n-(6-bromothieno[3,2-d]pyrimidin-4-yl)-1-n-(4-methoxyphenyl)benzene-1,4-diamine Chemical compound C1=CC(OC)=CC=C1NC(C=C1)=CC=C1NC1=NC=NC2=C1SC(Br)=C2 ZMFBDTFWPZMXGY-UHFFFAOYSA-N 0.000 claims description 4
• QRNGUNZTCURWQE-UHFFFAOYSA-N 4-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 QRNGUNZTCURWQE-UHFFFAOYSA-N 0.000 claims description 4
• OJJXAJROABVQGC-UHFFFAOYSA-N 6-(4-fluorophenyl)-n-(1h-indol-5-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(F)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 OJJXAJROABVQGC-UHFFFAOYSA-N 0.000 claims description 4
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 239000004146 Propane-1,2-diol Substances 0.000 claims description 4
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 4
• 206010039710 Scleroderma Diseases 0.000 claims description 4
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 239000002168 alkylating agent Substances 0.000 claims description 4
• 229940100198 alkylating agent Drugs 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 230000002280 anti-androgenic effect Effects 0.000 claims description 4
• 230000003388 anti-hormonal effect Effects 0.000 claims description 4
• 239000000051 antiandrogen Substances 0.000 claims description 4
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 4
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
• 239000012444 intercalating antibiotic Substances 0.000 claims description 4
• 208000002780 macular degeneration Diseases 0.000 claims description 4
• 230000000394 mitotic effect Effects 0.000 claims description 4
• YKJYSYWXBZWFJT-UHFFFAOYSA-N n-[1-(benzenesulfonyl)indol-5-yl]-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC2=CC(NC=3C=4SC(=CC=4N=CN=3)C=3C=CC=CC=3)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 YKJYSYWXBZWFJT-UHFFFAOYSA-N 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 208000017520 skin disease Diseases 0.000 claims description 4
• 201000002510 thyroid cancer Diseases 0.000 claims description 4
• 230000005747 tumor angiogenesis Effects 0.000 claims description 4
• IBJPRZJQQYQEGL-UHFFFAOYSA-N 1-ethyl-5-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]-3h-indol-2-one Chemical compound C=1C=C2N(CC)C(=O)CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 IBJPRZJQQYQEGL-UHFFFAOYSA-N 0.000 claims description 3
• DGVXXORAMMNCNL-UHFFFAOYSA-N 1-n-(4-methoxyphenyl)-4-n-thieno[3,2-d]pyrimidin-4-ylbenzene-1,4-diamine Chemical compound C1=CC(OC)=CC=C1NC(C=C1)=CC=C1NC1=NC=NC2=C1SC=C2 DGVXXORAMMNCNL-UHFFFAOYSA-N 0.000 claims description 3
• LZCNEECGDAOLCK-UHFFFAOYSA-N 3-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2C=3SC(=CC=3N=CN=2)C=2C=CC=CC=2)=C1 LZCNEECGDAOLCK-UHFFFAOYSA-N 0.000 claims description 3
• BXCQYJJWFMRGTA-UHFFFAOYSA-N 3-methyl-2-[4-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]phenyl]-1h-pyrazol-5-one Chemical compound CC1=CC(=O)NN1C(C=C1)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 BXCQYJJWFMRGTA-UHFFFAOYSA-N 0.000 claims description 3
• LBYZEYWQBWUPAI-UHFFFAOYSA-N 6-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]-3h-1,3-benzothiazole-2-thione Chemical compound C1=C2SC(S)=NC2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 LBYZEYWQBWUPAI-UHFFFAOYSA-N 0.000 claims description 3
• DDJGLMHFWNIVBN-UHFFFAOYSA-N 6-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 DDJGLMHFWNIVBN-UHFFFAOYSA-N 0.000 claims description 3
• RZBCSBPUQURGNR-UHFFFAOYSA-N 6-phenyl-n-(4-pyridin-2-yloxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound N=1C=NC=2C=C(C=3C=CC=CC=3)SC=2C=1NC(C=C1)=CC=C1OC1=CC=CC=N1 RZBCSBPUQURGNR-UHFFFAOYSA-N 0.000 claims description 3
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
• 229940123587 Cell cycle inhibitor Drugs 0.000 claims description 3
• 206010009944 Colon cancer Diseases 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 3
• 229940088598 enzyme Drugs 0.000 claims description 3
• 239000000367 immunologic factor Substances 0.000 claims description 3
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 3
• SLSBYLHSERKNPS-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 SLSBYLHSERKNPS-UHFFFAOYSA-N 0.000 claims description 3
• QXKDQOAACLBWER-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 QXKDQOAACLBWER-UHFFFAOYSA-N 0.000 claims description 3
• ODHAPDGNWNRLSG-UHFFFAOYSA-N n-[4-(4-methylpiperidin-1-yl)phenyl]-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1CC(C)CCN1C(C=C1)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 ODHAPDGNWNRLSG-UHFFFAOYSA-N 0.000 claims description 3
• 235000005152 nicotinamide Nutrition 0.000 claims description 3
• 229940044693 topoisomerase inhibitor Drugs 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• DLQIVYUBJDYVFM-UHFFFAOYSA-N 1-[3-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]phenyl]-2h-tetrazole-5-thione Chemical compound SC1=NN=NN1C1=CC=CC(NC=2C=3SC(=CC=3N=CN=2)C=2C=CC=CC=2)=C1 DLQIVYUBJDYVFM-UHFFFAOYSA-N 0.000 claims description 2
• KPTNWOAYEABEHN-UHFFFAOYSA-N 1-[5-[(2-pyridin-2-ylthieno[3,2-b]pyridin-7-yl)amino]-2,3-dihydroindol-1-yl]ethanone Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CC=N1 KPTNWOAYEABEHN-UHFFFAOYSA-N 0.000 claims description 2
• NUPSEKKGBUFLQY-UHFFFAOYSA-N 1-n-(2-phenylmethoxyethyl)-4-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)benzene-1,4-diamine Chemical compound C=1C=C(NC=2C=3SC(=CC=3N=CN=2)C=2C=CC=CC=2)C=CC=1NCCOCC1=CC=CC=C1 NUPSEKKGBUFLQY-UHFFFAOYSA-N 0.000 claims description 2
• LLIRAAASJOTEJI-UHFFFAOYSA-N 1-n-(3-methoxyphenyl)-4-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)benzene-1,4-diamine Chemical compound COC1=CC=CC(NC=2C=CC(NC=3C=4SC(=CC=4N=CN=3)C=3C=CC=CC=3)=CC=2)=C1 LLIRAAASJOTEJI-UHFFFAOYSA-N 0.000 claims description 2
• SVVUNFIUTCPYMO-UHFFFAOYSA-N 1-n-(3-methylphenyl)-4-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)benzene-1,4-diamine Chemical compound CC1=CC=CC(NC=2C=CC(NC=3C=4SC(=CC=4N=CN=3)C=3C=CC=CC=3)=CC=2)=C1 SVVUNFIUTCPYMO-UHFFFAOYSA-N 0.000 claims description 2
• FFXIDFXLLWEQTR-UHFFFAOYSA-N 1-n-(4-methoxyphenyl)-4-n-[6-(4-methoxyphenyl)thieno[3,2-d]pyrimidin-4-yl]benzene-1,4-diamine Chemical compound C1=CC(OC)=CC=C1NC(C=C1)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC(OC)=CC=1)=C2 FFXIDFXLLWEQTR-UHFFFAOYSA-N 0.000 claims description 2
• KNPZZHLWNXUFIA-UHFFFAOYSA-N 1-n-(4-methylphenyl)-2-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)benzene-1,2-diamine Chemical compound C1=CC(C)=CC=C1NC1=CC=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 KNPZZHLWNXUFIA-UHFFFAOYSA-N 0.000 claims description 2
• NLLYLSZIWQMFHU-UHFFFAOYSA-N 1-n-[4-(dimethylamino)phenyl]-4-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC(C=C1)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 NLLYLSZIWQMFHU-UHFFFAOYSA-N 0.000 claims description 2
• XDDVGCYWWYNCIZ-UHFFFAOYSA-N 2-(3-aminophenyl)-n-(1h-indol-5-yl)thieno[3,2-b]pyridin-7-amine Chemical compound NC1=CC=CC(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)C=CN=C3C=2)=C1 XDDVGCYWWYNCIZ-UHFFFAOYSA-N 0.000 claims description 2
• KCWAFYAMKNXBBW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(1h-indol-5-yl)thieno[3,2-b]pyridin-7-amine Chemical compound C1=CC(F)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 KCWAFYAMKNXBBW-UHFFFAOYSA-N 0.000 claims description 2
• FARWQILVZSOTOZ-UHFFFAOYSA-N 2-(diethylaminomethyl)-4-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]phenol Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C=3SC(=CC=3N=CN=2)C=2C=CC=CC=2)=C1 FARWQILVZSOTOZ-UHFFFAOYSA-N 0.000 claims description 2
• MYHDPPSRSQEVPE-UHFFFAOYSA-N 2-[2-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]-1,3-thiazol-5-yl]propan-2-ol Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=NC=C(C(C)(C)O)S1 MYHDPPSRSQEVPE-UHFFFAOYSA-N 0.000 claims description 2
• LQPOTGIAGBBCKH-UHFFFAOYSA-N 2-[[4-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]phenyl]methylamino]butan-1-ol Chemical compound C1=CC(CNC(CO)CC)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=C(C)NC4=CC=3)=C2S1 LQPOTGIAGBBCKH-UHFFFAOYSA-N 0.000 claims description 2
• HYCVSTDTGXTMOG-UHFFFAOYSA-N 2-[[5-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]-1h-indol-3-yl]methylamino]ethanol Chemical compound C1=C2C(CNCCO)=CNC2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 HYCVSTDTGXTMOG-UHFFFAOYSA-N 0.000 claims description 2
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 2
• GRTJNZLGVKRZLD-UHFFFAOYSA-N 3-[[4-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]phenyl]methylamino]propane-1,2-diol Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=C(CNCC(O)CO)C=C1 GRTJNZLGVKRZLD-UHFFFAOYSA-N 0.000 claims description 2
• LLIYQYBRIIJGLS-UHFFFAOYSA-N 4-[3-(thieno[3,2-d]pyrimidin-4-ylamino)-1h-pyrazol-5-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NNC(NC=2C=3SC=CC=3N=CN=2)=C1 LLIYQYBRIIJGLS-UHFFFAOYSA-N 0.000 claims description 2
• ASLAQNLSYGJKNM-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 ASLAQNLSYGJKNM-UHFFFAOYSA-N 0.000 claims description 2
• RMMSHPWKTDGOEG-UHFFFAOYSA-N 4-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)-1-n-(3,4,5-trimethoxyphenyl)benzene-1,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(NC=2C=CC(NC=3C=4SC(=CC=4N=CN=3)C=3C=CC=CC=3)=CC=2)=C1 RMMSHPWKTDGOEG-UHFFFAOYSA-N 0.000 claims description 2
• MFDVHTHRAGETJC-UHFFFAOYSA-N 5-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]-1-benzothiophene-2-carbonitrile Chemical compound C=1C=C2SC(C#N)=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 MFDVHTHRAGETJC-UHFFFAOYSA-N 0.000 claims description 2
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• CHBFWGRNNWGCMY-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-n-(1h-indol-5-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 CHBFWGRNNWGCMY-UHFFFAOYSA-N 0.000 claims description 2
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