HRP20000286A2 - Thienopyrimidine and thienopyridine derivatives useful as anticancer agents - Google Patents
Thienopyrimidine and thienopyridine derivatives useful as anticancer agents Download PDFInfo
- Publication number
- HRP20000286A2 HRP20000286A2 HR20000286A HRP20000286A HRP20000286A2 HR P20000286 A2 HRP20000286 A2 HR P20000286A2 HR 20000286 A HR20000286 A HR 20000286A HR P20000286 A HRP20000286 A HR P20000286A HR P20000286 A2 HRP20000286 A2 HR P20000286A2
- Authority
- HR
- Croatia
- Prior art keywords
- thieno
- phenyl
- indol
- pyrimidin
- amine
- Prior art date
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- 239000002246 antineoplastic agent Substances 0.000 title claims description 4
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 245
- 238000000034 method Methods 0.000 claims description 126
- -1 (5-phenyl-1H-pyrazol-3-yl)-thieno[3,2-d]pyrimidin-4-yl Chemical group 0.000 claims description 84
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 59
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 50
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 47
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- PTSRNABDORZGGL-UHFFFAOYSA-N 4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 PTSRNABDORZGGL-UHFFFAOYSA-N 0.000 claims description 31
- 206010028980 Neoplasm Diseases 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 241000124008 Mammalia Species 0.000 claims description 27
- 210000004027 cell Anatomy 0.000 claims description 23
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 23
- 208000035475 disorder Diseases 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 230000003463 hyperproliferative effect Effects 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 201000011510 cancer Diseases 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 210000002307 prostate Anatomy 0.000 claims description 14
- 210000000481 breast Anatomy 0.000 claims description 13
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 210000004072 lung Anatomy 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- LWXBFJDTVCQNTF-UHFFFAOYSA-N 2-bromo-n-(1h-indol-5-yl)thieno[3,2-b]pyridin-7-amine Chemical compound C1=C2NC=CC2=CC(NC=2C=CN=C3C=C(SC3=2)Br)=C1 LWXBFJDTVCQNTF-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 9
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- 201000004681 Psoriasis Diseases 0.000 claims description 8
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 7
- 108090000790 Enzymes Proteins 0.000 claims description 7
- 208000024770 Thyroid neoplasm Diseases 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
- 208000017169 kidney disease Diseases 0.000 claims description 7
- 210000000496 pancreas Anatomy 0.000 claims description 7
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 7
- 210000002784 stomach Anatomy 0.000 claims description 7
- 230000004862 vasculogenesis Effects 0.000 claims description 7
- 206010018338 Glioma Diseases 0.000 claims description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
- 206010033128 Ovarian cancer Diseases 0.000 claims description 6
- 206010060862 Prostate cancer Diseases 0.000 claims description 6
- 206010020718 hyperplasia Diseases 0.000 claims description 6
- 210000003734 kidney Anatomy 0.000 claims description 6
- 201000001441 melanoma Diseases 0.000 claims description 6
- 230000002611 ovarian Effects 0.000 claims description 6
- 210000003932 urinary bladder Anatomy 0.000 claims description 6
- XIYNNUPDXDUDNV-UHFFFAOYSA-N 4-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]benzaldehyde Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=C(C=O)C=C1 XIYNNUPDXDUDNV-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
- 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
- 201000008275 breast carcinoma Diseases 0.000 claims description 5
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims description 5
- 210000003128 head Anatomy 0.000 claims description 5
- 201000011066 hemangioma Diseases 0.000 claims description 5
- 201000005296 lung carcinoma Diseases 0.000 claims description 5
- 210000003739 neck Anatomy 0.000 claims description 5
- 210000001672 ovary Anatomy 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 201000001514 prostate carcinoma Diseases 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- FBUITIJPCQYNST-UHFFFAOYSA-N 1-n-(2-methoxyphenyl)-4-n-(6-phenylthieno[3,2-d]pyrimidin-4-yl)benzene-1,4-diamine Chemical compound COC1=CC=CC=C1NC(C=C1)=CC=C1NC1=NC=NC2=C1SC(C=1C=CC=CC=1)=C2 FBUITIJPCQYNST-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- 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
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- 208000007766 Kaposi sarcoma Diseases 0.000 claims description 4
- 206010033645 Pancreatitis Diseases 0.000 claims description 4
- 206010036590 Premature baby Diseases 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- 206010039710 Scleroderma Diseases 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 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
- 208000010668 atopic eczema Diseases 0.000 claims description 4
- 230000000711 cancerogenic effect Effects 0.000 claims description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 208000037976 chronic inflammation Diseases 0.000 claims description 4
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
- 230000007850 degeneration Effects 0.000 claims description 4
- 230000032692 embryo implantation Effects 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 230000000394 mitotic effect Effects 0.000 claims description 4
- 230000003387 muscular Effects 0.000 claims description 4
- CGDLXUGHZUDIDJ-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2NC=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 CGDLXUGHZUDIDJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229960004063 propylene glycol Drugs 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
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- 201000002510 thyroid cancer Diseases 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 230000005747 tumor angiogenesis Effects 0.000 claims description 4
- XQBGNNMVPXUMMH-UHFFFAOYSA-N 1-[3-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methylamino]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCNCC1=CC=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)C=C1 XQBGNNMVPXUMMH-UHFFFAOYSA-N 0.000 claims description 3
- PSRIIUUKNWOHQJ-UHFFFAOYSA-N 1-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1CC1=CC=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)C=C1 PSRIIUUKNWOHQJ-UHFFFAOYSA-N 0.000 claims description 3
- ULUUNYJTTJIXHY-UHFFFAOYSA-N 1-[[4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]phenyl]methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1CC1=CC=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)C=CN=C3C=2)C=C1 ULUUNYJTTJIXHY-UHFFFAOYSA-N 0.000 claims description 3
- QBRPEEWIGUOGKX-UHFFFAOYSA-N 1-n-(4-methoxyphenyl)-4-n-[6-(6-methoxypyridin-3-yl)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=NC(OC)=CC=1)=C2 QBRPEEWIGUOGKX-UHFFFAOYSA-N 0.000 claims description 3
- FTHVRWNSFRDQNV-UHFFFAOYSA-N 2-[2-[[4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]phenyl]methylamino]ethoxy]ethanol Chemical compound C1=CC(CNCCOCCO)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 FTHVRWNSFRDQNV-UHFFFAOYSA-N 0.000 claims description 3
- JEBYPEYXNOIEMZ-UHFFFAOYSA-N 2-[2-hydroxyethyl-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]amino]ethanol Chemical compound C1=CC(CN(CCO)CCO)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 JEBYPEYXNOIEMZ-UHFFFAOYSA-N 0.000 claims description 3
- GOTQICHLSRHZSG-UHFFFAOYSA-N 2-[4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 GOTQICHLSRHZSG-UHFFFAOYSA-N 0.000 claims description 3
- KDAVQLPYRSKUDG-UHFFFAOYSA-N 2-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methylamino]propane-1,3-diol Chemical compound C1=CC(CNC(CO)CO)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 KDAVQLPYRSKUDG-UHFFFAOYSA-N 0.000 claims description 3
- MVLNKEXGMMGTDC-UHFFFAOYSA-N 2-[[4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]phenyl]methyl-methylamino]ethanol Chemical compound C1=CC(CN(CCO)C)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 MVLNKEXGMMGTDC-UHFFFAOYSA-N 0.000 claims description 3
- FPSNGXJKXYUNOA-UHFFFAOYSA-N 3-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methylamino]propan-1-ol Chemical compound C1=CC(CNCCCO)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 FPSNGXJKXYUNOA-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- BTOJITJJYQUFRJ-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-n-(1h-indol-5-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 BTOJITJJYQUFRJ-UHFFFAOYSA-N 0.000 claims description 3
- HDWWBCJZHAYOEM-UHFFFAOYSA-N 6-(4-chlorophenyl)-n-(1h-indol-5-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 HDWWBCJZHAYOEM-UHFFFAOYSA-N 0.000 claims description 3
- BBUAFGBOVYCIKV-UHFFFAOYSA-N 6-(4-ethylphenyl)-n-(1h-indol-5-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(CC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 BBUAFGBOVYCIKV-UHFFFAOYSA-N 0.000 claims description 3
- YQBDZGJJXNSZBX-UHFFFAOYSA-N 6-[4-[(cyclopropylamino)methyl]phenyl]-n-(1h-indol-5-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)C=CC=1CNC1CC1 YQBDZGJJXNSZBX-UHFFFAOYSA-N 0.000 claims description 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
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- GYYSMYASTQEYLO-UHFFFAOYSA-N furan-2-yl-[4-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]piperazin-1-yl]methanone Chemical compound C1CN(CC=2C=CC(=CC=2)C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)CCN1C(=O)C1=CC=CO1 GYYSMYASTQEYLO-UHFFFAOYSA-N 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
- HKDUFLWFFUNFBG-UHFFFAOYSA-N n',n'-dimethyl-n-[[4-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]phenyl]methyl]propane-1,3-diamine Chemical compound C1=CC(CNCCCN(C)C)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=C(C)NC4=CC=3)=C2S1 HKDUFLWFFUNFBG-UHFFFAOYSA-N 0.000 claims description 3
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 3
- LYPWGVPKPGHUIQ-UHFFFAOYSA-N n'-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]-n-methylethane-1,2-diamine Chemical compound C1=CC(CNCCNC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 LYPWGVPKPGHUIQ-UHFFFAOYSA-N 0.000 claims description 3
- ZQMSIPOYNNOMBC-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-pyridin-2-ylthieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C2NC=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CC=N1 ZQMSIPOYNNOMBC-UHFFFAOYSA-N 0.000 claims description 3
- YKJMMLPNQSTDLZ-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-thiophen-2-ylthieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C2NC=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CS1 YKJMMLPNQSTDLZ-UHFFFAOYSA-N 0.000 claims description 3
- KEEWLMMJOKFRET-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-(3-methoxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)=C1 KEEWLMMJOKFRET-UHFFFAOYSA-N 0.000 claims description 3
- OKWONSLXKMFQOE-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-(4-methoxyphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 OKWONSLXKMFQOE-UHFFFAOYSA-N 0.000 claims description 3
- MDKUCHKNRBJPNN-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-(4-methylphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 MDKUCHKNRBJPNN-UHFFFAOYSA-N 0.000 claims description 3
- NCIHQVBGGIVCOS-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-(4-methylsulfanylphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(SC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 NCIHQVBGGIVCOS-UHFFFAOYSA-N 0.000 claims description 3
- MKBWQNWYJYTUHA-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-(methylaminomethyl)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(CNC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 MKBWQNWYJYTUHA-UHFFFAOYSA-N 0.000 claims description 3
- QEPFMZHZBPLSDW-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-(propylaminomethyl)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(CNCCC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 QEPFMZHZBPLSDW-UHFFFAOYSA-N 0.000 claims description 3
- ODNIFRPGKIKSLI-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-(trifluoromethyl)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 ODNIFRPGKIKSLI-UHFFFAOYSA-N 0.000 claims description 3
- OLSGAYIXWNZSOQ-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-[(2-methoxyethylamino)methyl]phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(CNCCOC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 OLSGAYIXWNZSOQ-UHFFFAOYSA-N 0.000 claims description 3
- JUYHZXWAGRMAEC-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-[(3-methoxypropylamino)methyl]phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(CNCCCOC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 JUYHZXWAGRMAEC-UHFFFAOYSA-N 0.000 claims description 3
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- DOMXOSVEFJHSFI-UHFFFAOYSA-N methyl 2-[[5-[(6-phenylthieno[3,2-d]pyrimidin-4-yl)amino]-1h-indol-3-yl]methylamino]acetate Chemical compound C1=C2C(CNCC(=O)OC)=CNC2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 DOMXOSVEFJHSFI-UHFFFAOYSA-N 0.000 claims description 2
- XURQBGLINHOJMK-UHFFFAOYSA-N methyl 2-amino-3-[3-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methyl]imidazol-4-yl]propanoate Chemical compound COC(=O)C(N)CC1=CN=CN1CC1=CC=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)C=C1 XURQBGLINHOJMK-UHFFFAOYSA-N 0.000 claims description 2
- VBFUVOHTQLKUFA-UHFFFAOYSA-N methyl 3-hydroxy-2-[[4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]phenyl]methylamino]propanoate Chemical compound C1=CC(CNC(CO)C(=O)OC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 VBFUVOHTQLKUFA-UHFFFAOYSA-N 0.000 claims description 2
- BOLQWGPMBGIUTM-UHFFFAOYSA-N methyl 4-[3-(thieno[3,2-d]pyrimidin-4-ylamino)-1h-pyrazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NNC(NC=2C=3SC=CC=3N=CN=2)=C1 BOLQWGPMBGIUTM-UHFFFAOYSA-N 0.000 claims description 2
- KEDFYXDEJZSZOT-UHFFFAOYSA-N methyl 4-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 KEDFYXDEJZSZOT-UHFFFAOYSA-N 0.000 claims description 2
- NCHMPYABNOWLAX-UHFFFAOYSA-N n',n'-diethyl-n-[[4-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]phenyl]methyl]propane-1,3-diamine Chemical compound C1=CC(CNCCCN(CC)CC)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=C(C)NC4=CC=3)=C2S1 NCHMPYABNOWLAX-UHFFFAOYSA-N 0.000 claims description 2
- FHVYYJDMXKZQCR-UHFFFAOYSA-N n',n'-dimethyl-n-[[4-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]phenyl]methyl]ethane-1,2-diamine Chemical compound C1=CC(CNCCN(C)C)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=C(C)NC4=CC=3)=C2S1 FHVYYJDMXKZQCR-UHFFFAOYSA-N 0.000 claims description 2
- BTZAXAXZZYOIJL-UHFFFAOYSA-N n'-[2-[[4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]phenyl]methylamino]ethyl]ethane-1,2-diamine Chemical compound C1=CC(CNCCNCCN)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 BTZAXAXZZYOIJL-UHFFFAOYSA-N 0.000 claims description 2
- MLKBKEXHMCNOID-UHFFFAOYSA-N n'-[2-[[4-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]phenyl]methylamino]ethyl]ethane-1,2-diamine Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=C(CNCCNCCN)C=C1 MLKBKEXHMCNOID-UHFFFAOYSA-N 0.000 claims description 2
- YBWHIJINFDHCDN-UHFFFAOYSA-N n'-[[4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]phenyl]methyl]ethane-1,2-diamine Chemical compound C1=CC(CNCCN)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 YBWHIJINFDHCDN-UHFFFAOYSA-N 0.000 claims description 2
- FJQLWVVVJGISHN-UHFFFAOYSA-N n'-[[4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]phenyl]methyl]hexane-1,6-diamine Chemical compound C1=CC(CNCCCCCCN)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 FJQLWVVVJGISHN-UHFFFAOYSA-N 0.000 claims description 2
- ANYALWSJIHQWHD-UHFFFAOYSA-N n'-[[4-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]phenyl]methyl]ethane-1,2-diamine Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=C(CNCCN)C=C1 ANYALWSJIHQWHD-UHFFFAOYSA-N 0.000 claims description 2
- NQFSLYXTAUCVMI-UHFFFAOYSA-N n'-[[5-[4-(1h-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl]thiophen-2-yl]methyl]-n-methylethane-1,2-diamine Chemical compound S1C(CNCCNC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 NQFSLYXTAUCVMI-UHFFFAOYSA-N 0.000 claims description 2
- SABFFOIBEUQYRT-UHFFFAOYSA-N n,n-dimethyl-5-[(2-pyridin-2-ylthieno[3,2-b]pyridin-7-yl)amino]-1h-indole-2-carboxamide Chemical compound C=1C=C2NC(C(=O)N(C)C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CC=N1 SABFFOIBEUQYRT-UHFFFAOYSA-N 0.000 claims description 2
- UXFCLAXHWACQTJ-UHFFFAOYSA-N n-(1,2,3-benzothiadiazol-6-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2N=NSC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 UXFCLAXHWACQTJ-UHFFFAOYSA-N 0.000 claims description 2
- HOMNAFIQTODDNN-UHFFFAOYSA-N n-(1,3-benzothiazol-6-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2N=CSC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 HOMNAFIQTODDNN-UHFFFAOYSA-N 0.000 claims description 2
- OYIXENLZOUZSFR-UHFFFAOYSA-N n-(1,3-dibromoindol-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1=C2C(Br)=CN(Br)C2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 OYIXENLZOUZSFR-UHFFFAOYSA-N 0.000 claims description 2
- NJQRDDIVETYXMA-UHFFFAOYSA-N n-(1-benzothiophen-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2SC=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 NJQRDDIVETYXMA-UHFFFAOYSA-N 0.000 claims description 2
- YADYTZSPBHCXQS-UHFFFAOYSA-N n-(1-methylindol-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2N(C)C=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 YADYTZSPBHCXQS-UHFFFAOYSA-N 0.000 claims description 2
- DVHQLHFIAMSFGW-UHFFFAOYSA-N n-(1h-indazol-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2NN=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 DVHQLHFIAMSFGW-UHFFFAOYSA-N 0.000 claims description 2
- OPCHDLXLEPSAID-UHFFFAOYSA-N n-(1h-indazol-6-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2C=NNC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 OPCHDLXLEPSAID-UHFFFAOYSA-N 0.000 claims description 2
- QKVBIEXWIKAORK-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-(6-methoxypyridin-3-yl)thieno[3,2-b]pyridin-7-amine Chemical compound C1=NC(OC)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 QKVBIEXWIKAORK-UHFFFAOYSA-N 0.000 claims description 2
- NWXHFVURZLIPKL-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-[4-(2-methoxyethoxy)phenyl]thieno[3,2-b]pyridin-7-amine Chemical compound C1=CC(OCCOC)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 NWXHFVURZLIPKL-UHFFFAOYSA-N 0.000 claims description 2
- SEDJHDRQDFAQHZ-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-[4-(2-morpholin-4-ylethoxy)phenyl]thieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)C=CN=C3C=2)C=CC=1OCCN1CCOCC1 SEDJHDRQDFAQHZ-UHFFFAOYSA-N 0.000 claims description 2
- KOYOJTYOEQWGGE-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-[4-(methylaminomethyl)phenyl]thieno[3,2-b]pyridin-7-amine Chemical compound C1=CC(CNC)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 KOYOJTYOEQWGGE-UHFFFAOYSA-N 0.000 claims description 2
- JCKSFAJUCQVQOF-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-[4-(morpholin-4-ylmethyl)phenyl]thieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)C=CN=C3C=2)C=CC=1CN1CCOCC1 JCKSFAJUCQVQOF-UHFFFAOYSA-N 0.000 claims description 2
- SOFDTSDGMYKGPE-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-[4-[(2-methoxyethylamino)methyl]phenyl]thieno[3,2-b]pyridin-7-amine Chemical compound C1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 SOFDTSDGMYKGPE-UHFFFAOYSA-N 0.000 claims description 2
- IRHHEJHLAHBRGF-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-[4-[(2-methylsulfanylethylamino)methyl]phenyl]thieno[3,2-b]pyridin-7-amine Chemical compound C1=CC(CNCCSC)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 IRHHEJHLAHBRGF-UHFFFAOYSA-N 0.000 claims description 2
- TVQBWKYSCASCCH-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-methyl-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C2=NC(C)=NC(NC=3C=C4C=CNC4=CC=3)=C2SC=1C1=CC=CC=C1 TVQBWKYSCASCCH-UHFFFAOYSA-N 0.000 claims description 2
- VUOACWHJBYSHPV-UHFFFAOYSA-N n-(1h-indol-5-yl)-2-pyridin-3-ylthieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C2NC=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CN=C1 VUOACWHJBYSHPV-UHFFFAOYSA-N 0.000 claims description 2
- BRDILUHLQPABHS-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-(3-methylsulfanylphenyl)thieno[3,2-d]pyrimidin-4-amine Chemical compound CSC1=CC=CC(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)=C1 BRDILUHLQPABHS-UHFFFAOYSA-N 0.000 claims description 2
- PZBWFOSTPYTBLF-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-(5-methylthiophen-2-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound S1C(C)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 PZBWFOSTPYTBLF-UHFFFAOYSA-N 0.000 claims description 2
- OPMNEHPWSJFTOB-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-(2-methoxyethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(OCCOC)=CC=C1C1=CC2=NC=NC(NC=3C=C4C=CNC4=CC=3)=C2S1 OPMNEHPWSJFTOB-UHFFFAOYSA-N 0.000 claims description 2
- REVKOTLECOQXLS-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-(2-morpholin-4-ylethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)C=CC=1OCCN1CCOCC1 REVKOTLECOQXLS-UHFFFAOYSA-N 0.000 claims description 2
- SLGJULOXVDFGRX-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-(2-pyrrolidin-1-ylethoxy)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)C=CC=1OCCN1CCCC1 SLGJULOXVDFGRX-UHFFFAOYSA-N 0.000 claims description 2
- OJZNTUIVQACYBD-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-(morpholin-4-ylmethyl)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)C=CC=1CN1CCOCC1 OJZNTUIVQACYBD-UHFFFAOYSA-N 0.000 claims description 2
- NCDFGXCIRWPDBX-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-[4-(thiomorpholin-4-ylmethyl)phenyl]thieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)N=CN=C3C=2)C=CC=1CN1CCSCC1 NCDFGXCIRWPDBX-UHFFFAOYSA-N 0.000 claims description 2
- URJCJYDZWBSKQH-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-pyridin-3-ylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2NC=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CN=C1 URJCJYDZWBSKQH-UHFFFAOYSA-N 0.000 claims description 2
- YXIIIHIHDBMOTL-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-thiophen-2-ylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2NC=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CS1 YXIIIHIHDBMOTL-UHFFFAOYSA-N 0.000 claims description 2
- LPDYCPCNPDEKIJ-UHFFFAOYSA-N n-(2,3-dihydro-1h-indol-5-yl)-2-pyridin-2-ylthieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C2NCCC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CC=N1 LPDYCPCNPDEKIJ-UHFFFAOYSA-N 0.000 claims description 2
- KPAIGABWHROLSV-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 KPAIGABWHROLSV-UHFFFAOYSA-N 0.000 claims description 2
- HBHCNRIMPXUQLV-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]benzamide Chemical compound C1=CC(C(=O)NCCO)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 HBHCNRIMPXUQLV-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- NWVUSUJOHOVKNG-UHFFFAOYSA-N n-(2-methyl-1h-indol-5-yl)-2-[4-(morpholin-4-ylmethyl)phenyl]thieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C(C=C1)=CC=C1CN1CCOCC1 NWVUSUJOHOVKNG-UHFFFAOYSA-N 0.000 claims description 2
- FLNDTWNDKMYWGZ-UHFFFAOYSA-N n-(2-methyl-1h-indol-5-yl)-2-pyridin-2-ylthieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CC=N1 FLNDTWNDKMYWGZ-UHFFFAOYSA-N 0.000 claims description 2
- BHQDAUJABYYOCH-UHFFFAOYSA-N n-(2-methyl-1h-indol-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 BHQDAUJABYYOCH-UHFFFAOYSA-N 0.000 claims description 2
- DMWLNBDXYXXOBU-UHFFFAOYSA-N n-(2h-benzotriazol-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2NN=NC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 DMWLNBDXYXXOBU-UHFFFAOYSA-N 0.000 claims description 2
- NSPSNNVGZURUHB-UHFFFAOYSA-N n-(3-bromo-1h-indol-5-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1=C2C(Br)=CNC2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 NSPSNNVGZURUHB-UHFFFAOYSA-N 0.000 claims description 2
- SHLAPZOGZCKFQQ-UHFFFAOYSA-N n-(3-ethynylphenyl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C#CC1=CC=CC(NC=2C=3SC(=CC=3N=CN=2)C=2C=CC=CC=2)=C1 SHLAPZOGZCKFQQ-UHFFFAOYSA-N 0.000 claims description 2
- ADAOHTJVVQLGQH-UHFFFAOYSA-N n-(3-hydroxypropyl)-6-[7-[(2-methyl-1h-indol-5-yl)amino]thieno[3,2-b]pyridin-2-yl]pyridine-3-carboxamide Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=C(C(=O)NCCCO)C=N1 ADAOHTJVVQLGQH-UHFFFAOYSA-N 0.000 claims description 2
- TYVRPJLWUMKEEC-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]pyridine-3-carboxamide Chemical compound C=1C=C(C=2SC3=C(NC=4C=C5C=CNC5=CC=4)C=CN=C3C=2)N=CC=1C(=O)NCCCN1C=CN=C1 TYVRPJLWUMKEEC-UHFFFAOYSA-N 0.000 claims description 2
- IIVNLRSCSPFOLN-UHFFFAOYSA-N n-(3h-benzimidazol-5-yl)-2-phenylthieno[3,2-b]pyridin-7-amine Chemical compound C=1C=C2NC=NC2=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CC=C1 IIVNLRSCSPFOLN-UHFFFAOYSA-N 0.000 claims description 2
- QTCZITGEMAFIJG-UHFFFAOYSA-N n-(7-methoxy-1h-indol-5-yl)-2-phenylthieno[3,2-b]pyridin-7-amine Chemical compound C=1C=2C=CNC=2C(OC)=CC=1NC(C=1S2)=CC=NC=1C=C2C1=CC=CC=C1 QTCZITGEMAFIJG-UHFFFAOYSA-N 0.000 claims description 2
- QYXHTCKXBXNPOT-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 QYXHTCKXBXNPOT-UHFFFAOYSA-N 0.000 claims description 2
- QVJSBJPXYOCUGE-UHFFFAOYSA-N n-(9h-carbazol-3-yl)-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2NC3=CC=CC=C3C2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 QVJSBJPXYOCUGE-UHFFFAOYSA-N 0.000 claims description 2
- BTADWVOQTFCGDU-UHFFFAOYSA-N n-[1-[3-(diethylamino)propyl]indol-5-yl]-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C=1C=C2N(CCCN(CC)CC)C=CC2=CC=1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 BTADWVOQTFCGDU-UHFFFAOYSA-N 0.000 claims description 2
- UGWUUDYHNSCFBW-UHFFFAOYSA-N n-[2-[[4-[7-(1h-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl]phenyl]methylamino]ethyl]acetamide Chemical compound C1=CC(CNCCNC(=O)C)=CC=C1C1=CC2=NC=CC(NC=3C=C4C=CNC4=CC=3)=C2S1 UGWUUDYHNSCFBW-UHFFFAOYSA-N 0.000 claims description 2
- FDTAIGVRQIIAOS-UHFFFAOYSA-N n-[3-(2-nitroethenyl)-1h-indol-5-yl]-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1=C2C(C=C[N+](=O)[O-])=CNC2=CC=C1NC(C=1S2)=NC=NC=1C=C2C1=CC=CC=C1 FDTAIGVRQIIAOS-UHFFFAOYSA-N 0.000 claims description 2
- YAOAWGJONUVDSB-UHFFFAOYSA-N n-[3-(5-methyl-3,4-dihydropyrazol-2-yl)phenyl]-6-phenylthieno[3,2-d]pyrimidin-4-amine Chemical compound C1CC(C)=NN1C1=CC=CC(NC=2C=3SC(=CC=3N=CN=2)C=2C=CC=CC=2)=C1 YAOAWGJONUVDSB-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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US6509797P | 1997-11-11 | 1997-11-11 | |
PCT/IB1998/001691 WO1999024440A1 (fr) | 1997-11-11 | 1998-10-22 | Derives de thienopyrimidine et thienopyridine utiles comme agents anticancereux |
Publications (1)
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HRP20000286A2 true HRP20000286A2 (en) | 2000-12-31 |
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HR20000286A HRP20000286A2 (en) | 1997-11-11 | 2000-05-10 | Thienopyrimidine and thienopyridine derivatives useful as anticancer agents |
Country Status (37)
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US (1) | US6492383B1 (fr) |
EP (1) | EP1028964A1 (fr) |
JP (1) | JP2001522853A (fr) |
KR (1) | KR100446363B1 (fr) |
CN (2) | CN101328186A (fr) |
AP (1) | AP976A (fr) |
AR (1) | AR018517A1 (fr) |
AU (1) | AU9454198A (fr) |
BG (1) | BG65180B1 (fr) |
BR (1) | BR9814018A (fr) |
CA (1) | CA2309690A1 (fr) |
CO (1) | CO4990956A1 (fr) |
CZ (1) | CZ20001709A3 (fr) |
DZ (1) | DZ2646A1 (fr) |
EA (1) | EA005889B1 (fr) |
GT (1) | GT199800180A (fr) |
HN (1) | HN1998000168A (fr) |
HR (1) | HRP20000286A2 (fr) |
HU (1) | HUP0100287A3 (fr) |
ID (1) | ID23978A (fr) |
IL (1) | IL135636A0 (fr) |
IS (1) | IS5464A (fr) |
MA (1) | MA24694A1 (fr) |
MY (1) | MY132073A (fr) |
NO (1) | NO20002162L (fr) |
NZ (1) | NZ520093A (fr) |
OA (1) | OA11376A (fr) |
PA (1) | PA8462401A1 (fr) |
PE (1) | PE129099A1 (fr) |
PL (1) | PL340589A1 (fr) |
SK (1) | SK6652000A3 (fr) |
TN (1) | TNSN98203A1 (fr) |
TW (1) | TW593321B (fr) |
UA (1) | UA72881C2 (fr) |
UY (2) | UY25238A1 (fr) |
WO (1) | WO1999024440A1 (fr) |
ZA (1) | ZA9810253B (fr) |
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JP3290666B2 (ja) * | 1995-06-07 | 2002-06-10 | ファイザー・インコーポレーテッド | 複素環式の縮合環ピリミジン誘導体 |
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HRP970371A2 (en) | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
ID19430A (id) | 1996-07-13 | 1998-07-09 | Glaxo Group Ltd | Senyawa senyawa heterosiklik |
US6187777B1 (en) | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
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1998
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1999
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2000
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