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

Thienopyrimidine and thienopyridine derivatives useful as anticancer agents. Download PDF

Info

Publication number: AP976A
Authority: AP; ARIPO
Prior art keywords: thieno; phenyl; pyrimidin; amine; ylamino
Prior art date: 1997-11-11

Application number

APAP/P/1998/001389A

Other languages

English (en)

Other versions

AP9801389A0 (en

Inventor

Michael John Munchhof

Susan Beth Sobolov-Jaynes

Original Assignee

Pfizer Prod Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-11-11

Filing date

1998-11-05

Publication date

2001-06-12

1998-11-05 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

1998-12-31 Publication of AP9801389A0 publication Critical patent/AP9801389A0/xx

2001-06-12 Application granted granted Critical

2001-06-12 Publication of AP976A publication Critical patent/AP976A/en

Links

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
PWLLWKGBEDBYHY-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-n-(1h-indol-5-yl)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=C2NC=CC2=CC(NC=2N=CN=C3C=C(SC3=2)C2=CC=C3OCOC3=C2)=C1 PWLLWKGBEDBYHY-UHFFFAOYSA-N 0.000 claims description 2
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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Classifications

- 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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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

APAP/P/1998/001389A 1997-11-11 1998-11-05 Thienopyrimidine and thienopyridine derivatives useful as anticancer agents. AP976A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US6509797P	1997-11-11	1997-11-11

Publications (2)

Publication Number	Publication Date
AP9801389A0 AP9801389A0 (en)	1998-12-31
AP976A true AP976A (en)	2001-06-12

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APAP/P/1998/001389A AP976A (en)	1997-11-11	1998-11-05	Thienopyrimidine and thienopyridine derivatives useful as anticancer agents.

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US (1)	US6492383B1 (fr)
EP (1)	EP1028964A1 (fr)
JP (1)	JP2001522853A (fr)
KR (1)	KR100446363B1 (fr)
CN (2)	CN1280580A (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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DE69838172T2 (de)	1997-08-22	2008-04-10	Astrazeneca Ab	Oxindolylchinazolinderivate als angiogenesehemmer
EP1006113A1 (fr)	1998-12-02	2000-06-07	Pfizer Products Inc.	Dérivés de 2-(2-oxo-éthylidène)-imidazolidin-4-one et leur utilisation pour inhiber la croissance anormale des cellules
UA71945C2 (en)	1999-01-27	2005-01-17	Pfizer Prod Inc	Substituted bicyclic derivatives being used as anticancer agents
GB9918057D0 (en) *	1999-07-30	1999-10-06	Univ Bristol	Therapeutic agents
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Publication number	Publication date
US6492383B1 (en)	2002-12-10
ZA9810253B (en)	2000-05-10
CA2309690A1 (fr)	1999-05-20
NO20002162L (no)	2000-07-10
EP1028964A1 (fr)	2000-08-23
SK6652000A3 (en)	2002-05-09
PA8462401A1 (es)	2000-05-24
NO20002162D0 (no)	2000-04-27
PE129099A1 (es)	1999-12-16
TW593321B (en)	2004-06-21
CN101328186A (zh)	2008-12-24
GT199800180A (es)	2000-05-02
HN1998000168A (es)	1999-01-08
HUP0100287A3 (en)	2003-04-28
UY25344A1 (es)	1999-09-27
EA200000391A1 (ru)	2000-12-25
CO4990956A1 (es)	2000-12-26
MY132073A (en)	2007-09-28
CZ20001709A3 (cs)	2001-12-12
HUP0100287A2 (hu)	2001-09-28
WO1999024440A1 (fr)	1999-05-20
NZ520093A (en)	2004-03-26
PL340589A1 (en)	2001-02-12
ID23978A (id)	2000-06-14
KR100446363B1 (ko)	2004-09-01
KR20010031908A (ko)	2001-04-16
UY25238A1 (es)	2000-12-29
TNSN98203A1 (fr)	2005-03-15
AU9454198A (en)	1999-05-31
EA005889B1 (ru)	2005-06-30
HRP20000286A2 (en)	2000-12-31
JP2001522853A (ja)	2001-11-20
AR018517A1 (es)	2001-11-28
AP9801389A0 (en)	1998-12-31
IS5464A (is)	2000-04-19
DZ2646A1 (fr)	2003-03-15
MA24694A1 (fr)	1999-07-01
BG104412A (en)	2001-02-28
BG65180B1 (bg)	2007-05-31
CN1280580A (zh)	2001-01-17
BR9814018A (pt)	2000-09-26
IL135636A0 (en)	2001-05-20
OA11376A (en)	2004-01-28
UA72881C2 (uk)	2005-05-16

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US6413971B1 (en)	2002-07-02	Fused bicyclic pyrimidine derivatives
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