JP2004517898A5 - - Google Patents
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- JP2004517898A5 JP2004517898A5 JP2002557948A JP2002557948A JP2004517898A5 JP 2004517898 A5 JP2004517898 A5 JP 2004517898A5 JP 2002557948 A JP2002557948 A JP 2002557948A JP 2002557948 A JP2002557948 A JP 2002557948A JP 2004517898 A5 JP2004517898 A5 JP 2004517898A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrazone
- pyrimidin
- methylthieno
- phenyl
- hydroxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
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- 150000007857 hydrazones Chemical class 0.000 claims description 125
- -1 4-pyridinyl Chemical group 0.000 claims description 113
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 claims description 53
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 32
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims description 25
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims description 21
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 16
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- AAKJQPDSJSZPEX-UHFFFAOYSA-N 7-methyl-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=CN=C1 AAKJQPDSJSZPEX-UHFFFAOYSA-N 0.000 claims description 4
- ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 claims description 2
- ZPKFAUMSOQNWKC-UHFFFAOYSA-N 2-chloro-4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]phenol Chemical compound Cc1csc2c(NN=Cc3ccc(O)c(Cl)c3)ncnc12 ZPKFAUMSOQNWKC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- NTBXLLOVTLCQGG-UHFFFAOYSA-N 2-ethoxy-4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]phenol Chemical compound CCOc1cc(C=NNc2ncnc3c(C)csc23)ccc1O NTBXLLOVTLCQGG-UHFFFAOYSA-N 0.000 claims description 2
- NXVQGMCWIORHSS-UHFFFAOYSA-N 2-methoxy-5-[(pyrido[2,3]thieno[2,4-d]pyrimidin-4-ylhydrazinylidene)methyl]phenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC1=NC=CC=C12 NXVQGMCWIORHSS-UHFFFAOYSA-N 0.000 claims description 2
- MODSKRFLIXWWRL-UHFFFAOYSA-N 2-methoxy-5-[[(7-methyl-6-thiophen-3-ylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]phenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(C1=CSC=C1)=C2C MODSKRFLIXWWRL-UHFFFAOYSA-N 0.000 claims description 2
- BHDMJEUFJFFWRC-UHFFFAOYSA-N 2-methoxy-5-[[[6-(2-methoxyphenyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]phenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(C=1C(=CC=CC=1)OC)=C2C BHDMJEUFJFFWRC-UHFFFAOYSA-N 0.000 claims description 2
- RFQMTLFTHOBXGU-UHFFFAOYSA-N 2-methoxy-5-[[[6-(4-methoxyphenyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]phenol Chemical compound C1=CC(OC)=CC=C1C1=C(C)C2=NC=NC(NN=CC=3C=C(O)C(OC)=CC=3)=C2S1 RFQMTLFTHOBXGU-UHFFFAOYSA-N 0.000 claims description 2
- JMHRPLQHMKEYAM-UHFFFAOYSA-N 2-methoxy-5-[[[6-(4-methoxyphenyl)thieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]phenol Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=NC(NN=CC=3C=C(O)C(OC)=CC=3)=C2S1 JMHRPLQHMKEYAM-UHFFFAOYSA-N 0.000 claims description 2
- UGVWGYVFGKBEHX-KCOMHNAKSA-N 2-methoxy-5-[[[7-methyl-6-[(e)-2-phenylethenyl]thieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]phenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(\C=C\C=1C=CC=CC=1)=C2C UGVWGYVFGKBEHX-KCOMHNAKSA-N 0.000 claims description 2
- HEXFFYQBBGRUKE-UHFFFAOYSA-N 3-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]benzoic acid Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=CC(C(O)=O)=C1 HEXFFYQBBGRUKE-UHFFFAOYSA-N 0.000 claims description 2
- OOMHDBWVLZZETG-UHFFFAOYSA-N 3-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]benzonitrile Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=CC(C#N)=C1 OOMHDBWVLZZETG-UHFFFAOYSA-N 0.000 claims description 2
- LOPRJHOLWKJBAP-UHFFFAOYSA-N 3-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]phenol Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=CC(O)=C1 LOPRJHOLWKJBAP-UHFFFAOYSA-N 0.000 claims description 2
- DDXMNTHLLKWVSW-UHFFFAOYSA-N 4-[4-[2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazinyl]-7-methylthieno[3,2-d]pyrimidin-6-yl]benzoic acid Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(C=1C=CC(=CC=1)C(O)=O)=C2C DDXMNTHLLKWVSW-UHFFFAOYSA-N 0.000 claims description 2
- BQSAMTVYGQCLKQ-UHFFFAOYSA-N 4-[7-methyl-4-[2-(pyridin-3-ylmethylidene)hydrazinyl]thieno[3,2-d]pyrimidin-6-yl]benzoic acid Chemical compound N1=CN=C2C(C)=C(C=3C=CC(=CC=3)C(O)=O)SC2=C1NN=CC1=CC=CN=C1 BQSAMTVYGQCLKQ-UHFFFAOYSA-N 0.000 claims description 2
- XOXLRHOUBGXBSI-UHFFFAOYSA-N 4-[[(6-iodo-7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]benzoic acid Chemical compound N1=CN=C2C(C)=C(I)SC2=C1NN=CC1=CC=C(C(O)=O)C=C1 XOXLRHOUBGXBSI-UHFFFAOYSA-N 0.000 claims description 2
- SJZHHRGQDXFPID-UHFFFAOYSA-N 4-[[(7-methyl-6-phenylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]benzoic acid Chemical compound N1=CN=C2C(C)=C(C=3C=CC=CC=3)SC2=C1NN=CC1=CC=C(C(O)=O)C=C1 SJZHHRGQDXFPID-UHFFFAOYSA-N 0.000 claims description 2
- ZMAQUBYUBYLLAP-UHFFFAOYSA-N 4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]benzonitrile Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=C(C#N)C=C1 ZMAQUBYUBYLLAP-UHFFFAOYSA-N 0.000 claims description 2
- IOPNIWISFBVLOA-UHFFFAOYSA-N 4-[[[6-(2-chlorophenyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]benzoic acid Chemical compound N1=CN=C2C(C)=C(C=3C(=CC=CC=3)Cl)SC2=C1NN=CC1=CC=C(C(O)=O)C=C1 IOPNIWISFBVLOA-UHFFFAOYSA-N 0.000 claims description 2
- JDEBTANWVSAEPC-UHFFFAOYSA-N 4-[[[6-(2-methoxyphenyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]benzoic acid Chemical compound COC1=CC=CC=C1C1=C(C)C2=NC=NC(NN=CC=3C=CC(=CC=3)C(O)=O)=C2S1 JDEBTANWVSAEPC-UHFFFAOYSA-N 0.000 claims description 2
- DEMILDCEFWLMKF-UHFFFAOYSA-N 4-[[[6-(hydroxymethyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]benzoic acid Chemical compound N1=CN=C2C(C)=C(CO)SC2=C1NN=CC1=CC=C(C(O)=O)C=C1 DEMILDCEFWLMKF-UHFFFAOYSA-N 0.000 claims description 2
- BYVQLNHZHWGMOR-QGRJAXEJSA-N 4-[[[7-methyl-6-[(E)-2-phenylethenyl]thieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]benzoic acid Chemical compound S1C2=C(NN=CC=3C=CC(=CC=3)C(O)=O)N=CN=C2C(C)=C1\C=C\C1=CC=CC=C1 BYVQLNHZHWGMOR-QGRJAXEJSA-N 0.000 claims description 2
- YTHJCZRFJGXPTL-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1[N+]([O-])=O YTHJCZRFJGXPTL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- RNXUJXQDDPFKPD-UHFFFAOYSA-N 5-[[(6-iodo-7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(I)=C2C RNXUJXQDDPFKPD-UHFFFAOYSA-N 0.000 claims description 2
- IDYJQGNYZPATLU-UHFFFAOYSA-N 5-[[(6-iodothieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(I)=C2 IDYJQGNYZPATLU-UHFFFAOYSA-N 0.000 claims description 2
- GRLNUSATVWDHKJ-UHFFFAOYSA-N 5-[[[6-(2-chlorophenyl)thieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(C=1C(=CC=CC=1)Cl)=C2 GRLNUSATVWDHKJ-UHFFFAOYSA-N 0.000 claims description 2
- LGHZTFVKQYWWNK-UHFFFAOYSA-N 5-[[[6-(hydroxymethyl)-7-methylthieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(CO)=C2C LGHZTFVKQYWWNK-UHFFFAOYSA-N 0.000 claims description 2
- YSRUOIZBMRHERS-UHFFFAOYSA-N 5-[[[6-[3-(hydroxymethyl)phenyl]-7-methylthieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(C=1C=C(CO)C=CC=1)=C2C YSRUOIZBMRHERS-UHFFFAOYSA-N 0.000 claims description 2
- UMYATDVIQDDJQT-UHFFFAOYSA-N 5-[[[6-[4-(hydroxymethyl)phenyl]-7-methylthieno[3,2-d]pyrimidin-4-yl]hydrazinylidene]methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C=NNC1=NC=NC2=C1SC(C=1C=CC(CO)=CC=1)=C2C UMYATDVIQDDJQT-UHFFFAOYSA-N 0.000 claims description 2
- YSBSULUTNRFRDS-UHFFFAOYSA-N 6-(2-chlorophenyl)-7-methyl-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=C(C=3C(=CC=CC=3)Cl)SC2=C1NN=CC1=CC=CN=C1 YSBSULUTNRFRDS-UHFFFAOYSA-N 0.000 claims description 2
- KQVCTZKXQKGMSR-UHFFFAOYSA-N 6-(2-chlorophenyl)-N-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC=C1C1=CC2=NC=NC(NN=CC=3C=NC=CC=3)=C2S1 KQVCTZKXQKGMSR-UHFFFAOYSA-N 0.000 claims description 2
- HXQRLCJCCBCOBK-UHFFFAOYSA-N 6-(2-chlorophenyl)-n-(thiophen-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC=C1C1=CC2=NC=NC(NN=CC=3SC=CC=3)=C2S1 HXQRLCJCCBCOBK-UHFFFAOYSA-N 0.000 claims description 2
- AIGMDHJUCHBRAJ-UHFFFAOYSA-N 6-(2-methoxyphenyl)-7-methyl-n-(thiophen-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=C(C)C2=NC=NC(NN=CC=3SC=CC=3)=C2S1 AIGMDHJUCHBRAJ-UHFFFAOYSA-N 0.000 claims description 2
- SUJLGOHFQPKHEQ-UHFFFAOYSA-N 6-(3-chlorophenyl)-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(C=2SC3=C(NN=CC=4C=NC=CC=4)N=CN=C3C=2)=C1 SUJLGOHFQPKHEQ-UHFFFAOYSA-N 0.000 claims description 2
- RTGCKDILDNHURS-UHFFFAOYSA-N 6-(3-methoxyphenyl)-7-methyl-n-(thiophen-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(C2=C(C3=NC=NC(NN=CC=4SC=CC=4)=C3S2)C)=C1 RTGCKDILDNHURS-UHFFFAOYSA-N 0.000 claims description 2
- LMTIEPZWMXXDBK-UHFFFAOYSA-N 6-(4-chlorophenyl)-N-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C1=CC2=NC=NC(NN=CC=3C=NC=CC=3)=C2S1 LMTIEPZWMXXDBK-UHFFFAOYSA-N 0.000 claims description 2
- GJZAPLCUXASPAA-UHFFFAOYSA-N 6-(4-fluorophenyl)-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(F)=CC=C1C1=CC2=NC=NC(NN=CC=3C=NC=CC=3)=C2S1 GJZAPLCUXASPAA-UHFFFAOYSA-N 0.000 claims description 2
- KKTUDZCYMNIYTO-UHFFFAOYSA-N 6-(4-methoxyphenyl)-N-(thiophen-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=NC(NN=CC=3SC=CC=3)=C2S1 KKTUDZCYMNIYTO-UHFFFAOYSA-N 0.000 claims description 2
- KSXMWOQBGYYRMY-UHFFFAOYSA-N 6-(4-methoxyphenyl)-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=NC(NN=CC=3C=NC=CC=3)=C2S1 KSXMWOQBGYYRMY-UHFFFAOYSA-N 0.000 claims description 2
- FDRBQMIHMUDVRI-UHFFFAOYSA-N 6-(4-methylsulfonylphenyl)-N-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC2=NC=NC(NN=CC=3C=NC=CC=3)=C2S1 FDRBQMIHMUDVRI-UHFFFAOYSA-N 0.000 claims description 2
- VVNOGCPUDPDRAQ-UHFFFAOYSA-N 6-iodo-7-methyl-N-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=C(I)SC2=C1NN=CC1=CC=CN=C1 VVNOGCPUDPDRAQ-UHFFFAOYSA-N 0.000 claims description 2
- ZVJGVGZVJOQTAY-UHFFFAOYSA-N 6-iodo-7-methyl-n-(thiophen-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=C(I)SC2=C1NN=CC1=CC=CS1 ZVJGVGZVJOQTAY-UHFFFAOYSA-N 0.000 claims description 2
- OCKGNHJJOXBMSU-UHFFFAOYSA-N 6-iodo-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound C=12SC(I)=CC2=NC=NC=1NN=CC1=CC=CN=C1 OCKGNHJJOXBMSU-UHFFFAOYSA-N 0.000 claims description 2
- RFQLOANFLWFATP-UHFFFAOYSA-N 6-iodo-n-(thiophen-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound C=12SC(I)=CC2=NC=NC=1NN=CC1=CC=CS1 RFQLOANFLWFATP-UHFFFAOYSA-N 0.000 claims description 2
- AVPJUEOAFHTBQK-UHFFFAOYSA-N 6-phenyl-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N=1C=NC=2C=C(C=3C=CC=CC=3)SC=2C=1NN=CC1=CC=CN=C1 AVPJUEOAFHTBQK-UHFFFAOYSA-N 0.000 claims description 2
- HSWCWWGRZFYCJM-UHFFFAOYSA-N 7-ethyl-N-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(CC)=CSC2=C1NN=CC1=CC=CN=C1 HSWCWWGRZFYCJM-UHFFFAOYSA-N 0.000 claims description 2
- WHSBSHLMDWFBMF-UHFFFAOYSA-N 7-methyl-4-[2-(pyridin-3-ylmethylidene)hydrazinyl]thieno[3,2-d]pyrimidine-6-carboxylic acid Chemical compound N1=CN=C2C(C)=C(C(O)=O)SC2=C1NN=CC1=CC=CN=C1 WHSBSHLMDWFBMF-UHFFFAOYSA-N 0.000 claims description 2
- AXRYWHGOVYOUOF-UHFFFAOYSA-N 7-methyl-4-[2-(thiophen-2-ylmethylidene)hydrazinyl]thieno[3,2-d]pyrimidine-6-carboxylic acid Chemical compound N1=CN=C2C(C)=C(C(O)=O)SC2=C1NN=CC1=CC=CS1 AXRYWHGOVYOUOF-UHFFFAOYSA-N 0.000 claims description 2
- KREPHSVZIMYUBD-UHFFFAOYSA-N 7-methyl-6-phenyl-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=C(C=3C=CC=CC=3)SC2=C1NN=CC1=CC=CN=C1 KREPHSVZIMYUBD-UHFFFAOYSA-N 0.000 claims description 2
- LDTPEFMJGGTDAB-UHFFFAOYSA-N 7-methyl-6-phenyl-n-(thiophen-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=C(C=3C=CC=CC=3)SC2=C1NN=CC1=CC=CS1 LDTPEFMJGGTDAB-UHFFFAOYSA-N 0.000 claims description 2
- QTXNOOCJAQCWAD-UHFFFAOYSA-N 7-methyl-6-thiophen-3-yl-N-(thiophen-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=C(C3=CSC=C3)SC2=C1NN=CC1=CC=CS1 QTXNOOCJAQCWAD-UHFFFAOYSA-N 0.000 claims description 2
- WBJXLFDJYNROBG-UHFFFAOYSA-N 7-methyl-N-[(5-methyl-1H-imidazol-4-yl)methylideneamino]thieno[3,2-d]pyrimidin-4-amine Chemical compound Cc1csc2c(NN=Cc3nc[nH]c3C)ncnc12 WBJXLFDJYNROBG-UHFFFAOYSA-N 0.000 claims description 2
- PJTITAAFFRJHGM-UHFFFAOYSA-N 7-methyl-n-(1,3-thiazol-2-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=NC=CS1 PJTITAAFFRJHGM-UHFFFAOYSA-N 0.000 claims description 2
- UERNGGHFXRMXJD-UHFFFAOYSA-N 7-methyl-n-(1-pyridin-3-ylethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N=1C=NC=2C(C)=CSC=2C=1NN=C(C)C1=CC=CN=C1 UERNGGHFXRMXJD-UHFFFAOYSA-N 0.000 claims description 2
- LTOUZBGGZPFVCR-UHFFFAOYSA-N 7-methyl-n-(oxolan-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1CCOC1 LTOUZBGGZPFVCR-UHFFFAOYSA-N 0.000 claims description 2
- QMXUPIZDBQIKEN-UHFFFAOYSA-N 7-methyl-n-(pentylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound CCCCC=NNC1=NC=NC2=C1SC=C2C QMXUPIZDBQIKEN-UHFFFAOYSA-N 0.000 claims description 2
- IFLMJJYIAMHRAU-UHFFFAOYSA-N 7-methyl-n-(propylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound CCC=NNC1=NC=NC2=C1SC=C2C IFLMJJYIAMHRAU-UHFFFAOYSA-N 0.000 claims description 2
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- XZTNTINIFUGGQF-UHFFFAOYSA-N 7-methyl-n-(thiophen-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC=1C=CSC=1 XZTNTINIFUGGQF-UHFFFAOYSA-N 0.000 description 1
- HOYOXFMCPFYSFM-UHFFFAOYSA-N 7-methyl-n-[(1-methylimidazol-2-yl)methylideneamino]thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=NC=CN1C HOYOXFMCPFYSFM-UHFFFAOYSA-N 0.000 description 1
- PPUURJPPXYCJCZ-UHFFFAOYSA-N [3-[7-methyl-4-[2-(thiophen-2-ylmethylidene)hydrazinyl]thieno[3,2-d]pyrimidin-6-yl]phenyl]methanol Chemical compound N1=CN=C2C(C)=C(C=3C=C(CO)C=CC=3)SC2=C1NN=CC1=CC=CS1 PPUURJPPXYCJCZ-UHFFFAOYSA-N 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- INKDEWPCMLQGGZ-UHFFFAOYSA-N n-[(3-bromophenyl)methylideneamino]-7-methylthieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=CC(Br)=C1 INKDEWPCMLQGGZ-UHFFFAOYSA-N 0.000 description 1
- UZHUXNKHWASHQS-UHFFFAOYSA-N n-[(3-chlorophenyl)methylideneamino]-7-methylthieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=CC(Cl)=C1 UZHUXNKHWASHQS-UHFFFAOYSA-N 0.000 description 1
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/694,145 US6503914B1 (en) | 2000-10-23 | 2000-10-23 | Thienopyrimidine-based inhibitors of the Src family |
| PCT/US2001/050198 WO2002057271A2 (en) | 2000-10-23 | 2001-10-23 | Thienopyrimidine-based inhibitors of the src family |
Publications (2)
| Publication Number | Publication Date |
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| EP (1) | EP1409491A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2004517898A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20030040554A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2002246817B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2426775A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA03003580A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002057271A2 (cg-RX-API-DMAC7.html) |
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-
2000
- 2000-10-23 US US09/694,145 patent/US6503914B1/en not_active Ceased
-
2001
- 2001-10-23 JP JP2002557948A patent/JP2004517898A/ja active Pending
- 2001-10-23 CA CA002426775A patent/CA2426775A1/en not_active Abandoned
- 2001-10-23 US US10/399,816 patent/US7285556B2/en not_active Expired - Fee Related
- 2001-10-23 KR KR10-2003-7005566A patent/KR20030040554A/ko not_active Abandoned
- 2001-10-23 MX MXPA03003580A patent/MXPA03003580A/es not_active Application Discontinuation
- 2001-10-23 AU AU2002246817A patent/AU2002246817B2/en not_active Ceased
- 2001-10-23 EP EP01994425A patent/EP1409491A2/en not_active Withdrawn
- 2001-10-23 WO PCT/US2001/050198 patent/WO2002057271A2/en not_active Ceased
-
2004
- 2004-06-28 US US10/878,140 patent/USRE39267E1/en not_active Expired - Fee Related
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