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
Applications Claiming Priority (2)
| 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 |
|---|---|
| JP2004517898A JP2004517898A (ja) | 2004-06-17 |
| JP2004517898A5 true JP2004517898A5 (enExample) | 2005-06-02 |
Family
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| JP2002557948A Pending JP2004517898A (ja) | 2000-10-23 | 2001-10-23 | Ｓｒｃ族のチエノピリミジン系阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US6503914B1 (enExample) |
| EP (1) | EP1409491A2 (enExample) |
| JP (1) | JP2004517898A (enExample) |
| KR (1) | KR20030040554A (enExample) |
| AU (1) | AU2002246817B2 (enExample) |
| CA (1) | CA2426775A1 (enExample) |
| MX (1) | MXPA03003580A (enExample) |
| WO (1) | WO2002057271A2 (enExample) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6334960B1 (en) * | 1999-03-11 | 2002-01-01 | Board Of Regents, The University Of Texas System | Step and flash imprint lithography |
| WO2003064428A1 (en) * | 2002-01-29 | 2003-08-07 | H. Lundbeck A/S | Furano- and thienopyrimidines as neurokinase inhibitors |
| AU2003216322A1 (en) * | 2002-02-15 | 2003-09-09 | Rigel Pharmaceuticals, Inc. | Inhibitors of tubulin polymerization |
| GB0226434D0 (en) * | 2002-11-13 | 2002-12-18 | Astrazeneca Ab | Combination product |
| US7365103B2 (en) * | 2002-12-12 | 2008-04-29 | Board Of Regents, The University Of Texas System | Compositions for dark-field polymerization and method of using the same for imprint lithography processes |
| US20040112862A1 (en) * | 2002-12-12 | 2004-06-17 | Molecular Imprints, Inc. | Planarization composition and method of patterning a substrate using the same |
| US20040168613A1 (en) * | 2003-02-27 | 2004-09-02 | Molecular Imprints, Inc. | Composition and method to form a release layer |
| US7122079B2 (en) | 2004-02-27 | 2006-10-17 | Molecular Imprints, Inc. | Composition for an etching mask comprising a silicon-containing material |
| US7396475B2 (en) | 2003-04-25 | 2008-07-08 | Molecular Imprints, Inc. | Method of forming stepped structures employing imprint lithography |
| US20050160934A1 (en) * | 2004-01-23 | 2005-07-28 | Molecular Imprints, Inc. | Materials and methods for imprint lithography |
| US20060108710A1 (en) * | 2004-11-24 | 2006-05-25 | Molecular Imprints, Inc. | Method to reduce adhesion between a conformable region and a mold |
| US7157036B2 (en) | 2003-06-17 | 2007-01-02 | Molecular Imprints, Inc | Method to reduce adhesion between a conformable region and a pattern of a mold |
| US7307118B2 (en) * | 2004-11-24 | 2007-12-11 | Molecular Imprints, Inc. | Composition to reduce adhesion between a conformable region and a mold |
| GB0314943D0 (en) * | 2003-06-25 | 2003-07-30 | Proteome Sciences Plc | Screening methods |
| CA2532084A1 (en) * | 2003-07-11 | 2005-02-03 | Oregon Health And Science University | Methods of treatment and diagnosis using modulators of virus-induced cellular gene sequences |
| US20060014165A1 (en) * | 2003-07-14 | 2006-01-19 | Decode Genetics Ehf. | Methods of diagnosis and treatment for asthma and other respiratory diseases based on haplotype association |
| WO2005004824A1 (ja) * | 2003-07-15 | 2005-01-20 | Kao Corporation | 口腔用組成物 |
| US20050084804A1 (en) * | 2003-10-16 | 2005-04-21 | Molecular Imprints, Inc. | Low surface energy templates |
| US7122482B2 (en) * | 2003-10-27 | 2006-10-17 | Molecular Imprints, Inc. | Methods for fabricating patterned features utilizing imprint lithography |
| US20050107386A1 (en) * | 2003-11-19 | 2005-05-19 | Rama Krishna Narla | Methods of treating diseases and disorders by targeting multiple kinases |
| WO2005072826A2 (en) | 2004-01-21 | 2005-08-11 | Emory University | Compositions and use of tyrosine kinase inhibitors to treat pathogenic infection |
| US8076386B2 (en) | 2004-02-23 | 2011-12-13 | Molecular Imprints, Inc. | Materials for imprint lithography |
| US7906180B2 (en) | 2004-02-27 | 2011-03-15 | Molecular Imprints, Inc. | Composition for an etching mask comprising a silicon-containing material |
| EP2298292A3 (en) | 2004-06-18 | 2011-08-10 | Agennix USA Inc. | Kinase inhibitors for treating cancers |
| US20060004002A1 (en) * | 2004-07-02 | 2006-01-05 | Thomas Thrash | Small molecule thienopyrimidine-based protein tyrosine kinase inhibitors |
| US20060004197A1 (en) * | 2004-07-02 | 2006-01-05 | Thomas Thrash | Sulfonamide-based compounds as protein tyrosine kinase inhibitors |
| US20060003980A1 (en) * | 2004-07-02 | 2006-01-05 | Shamsuddin Shaikh | Cobalt(II) complexes as protein tyrosine kinase inhibitors |
| ATE485300T1 (de) * | 2004-07-16 | 2010-11-15 | Sunesis Pharmaceuticals Inc | Als aurora-kinase-inhibitoren nutzbare thienopyrimidine |
| US7939131B2 (en) | 2004-08-16 | 2011-05-10 | Molecular Imprints, Inc. | Method to provide a layer with uniform etch characteristics |
| US7282550B2 (en) * | 2004-08-16 | 2007-10-16 | Molecular Imprints, Inc. | Composition to provide a layer with uniform etch characteristics |
| CA2579472A1 (en) * | 2004-09-14 | 2006-03-23 | The Genetics Company, Inc. | Hydrazone derivatives and their use as beta secretase inhibitors |
| US20060062922A1 (en) * | 2004-09-23 | 2006-03-23 | Molecular Imprints, Inc. | Polymerization technique to attenuate oxygen inhibition of solidification of liquids and composition therefor |
| US20060081557A1 (en) * | 2004-10-18 | 2006-04-20 | Molecular Imprints, Inc. | Low-k dielectric functional imprinting materials |
| EP1814561A4 (en) | 2004-10-29 | 2012-12-19 | Biocryst Pharm Inc | THEROPUTICAL FUROPYRIMIDINES AND THIENOPYRIMIDINES |
| US7292326B2 (en) | 2004-11-30 | 2007-11-06 | Molecular Imprints, Inc. | Interferometric analysis for the manufacture of nano-scale devices |
| WO2006078942A2 (en) * | 2005-01-21 | 2006-07-27 | President And Fellows Of Harvard College | Regulation of protein synthesis by inhibition of eif4e-eif4g interaction |
| US8808808B2 (en) | 2005-07-22 | 2014-08-19 | Molecular Imprints, Inc. | Method for imprint lithography utilizing an adhesion primer layer |
| US8557351B2 (en) * | 2005-07-22 | 2013-10-15 | Molecular Imprints, Inc. | Method for adhering materials together |
| US7759407B2 (en) * | 2005-07-22 | 2010-07-20 | Molecular Imprints, Inc. | Composition for adhering materials together |
| EP1917528B1 (en) * | 2005-08-24 | 2011-08-17 | Bristol-Myers Squibb Company | Biomarkers and methods for determining sensitivity to epidermal growth factor receptor modulators |
| US8142703B2 (en) * | 2005-10-05 | 2012-03-27 | Molecular Imprints, Inc. | Imprint lithography method |
| US20070099877A1 (en) * | 2005-11-02 | 2007-05-03 | Cytovia, Inc. | N-aryl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| WO2007056208A2 (en) * | 2005-11-02 | 2007-05-18 | Cytovia, Inc. | N-arylalkyl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| WO2007056214A2 (en) * | 2005-11-02 | 2007-05-18 | Cytovia, Inc | N-alkyl-n-aryl-thienopyrimidin-r-amines and uses thereof |
| AU2006323944B2 (en) * | 2005-12-08 | 2012-08-16 | Merck Serono Sa | Antiproliferative pyrimidyl, fused pyrimidyl and pyrimidyl hydrazones |
| WO2007112015A2 (en) * | 2006-03-24 | 2007-10-04 | The Feinstein Institute For Medical Research | Phenolic hydrazone macrophage migration inhibitory factor inhibitors |
| US20080110557A1 (en) * | 2006-11-15 | 2008-05-15 | Molecular Imprints, Inc. | Methods and Compositions for Providing Preferential Adhesion and Release of Adjacent Surfaces |
| CA2680330A1 (en) * | 2007-03-13 | 2008-09-18 | Alberto Bardelli | K-ras and b-raf mutations and anti-egfr antibody therapy |
| EP2121989B2 (en) | 2007-03-13 | 2022-03-09 | Amgen Inc. | K-ras mutations and anti-egfr antibody therapy |
| WO2008124066A1 (en) | 2007-04-05 | 2008-10-16 | The J. David Gladstone Institutes | Agents that reduce neuronal overexcitation |
| US20100109195A1 (en) | 2008-11-05 | 2010-05-06 | Molecular Imprints, Inc. | Release agent partition control in imprint lithography |
| SG182361A1 (en) | 2010-01-29 | 2012-08-30 | Hanmi Science Co Ltd | THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY ON PROTEIN KINASES |
| SI2540728T1 (sl) | 2010-02-17 | 2019-06-28 | Takeda Pharmaceutical Company Limited | Heterociklična spojina |
| CN102250112A (zh) * | 2010-05-18 | 2011-11-23 | 上海再启生物技术有限公司 | 7-溴-4-氨基噻吩并嘧啶的制备方法 |
| TW201204733A (en) | 2010-06-25 | 2012-02-01 | Kowa Co | Novel condensed pyridine or condensed pyrimidine derivative, and medicinal agent comprising same |
| EP2601519B1 (en) * | 2010-07-30 | 2017-12-06 | Expression Pathology, Inc. | C-src selected reaction monitoring assay |
| SG11201408679XA (en) | 2012-06-26 | 2015-01-29 | Del Mar Pharmaceuticals | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
| JP6120311B2 (ja) * | 2013-02-12 | 2017-04-26 | 学校法人銀杏学園 | ポリフェノール化合物 |
| JP6936221B2 (ja) | 2015-11-02 | 2021-09-15 | ファイブ プライム セラピューティクス， インコーポレイテッド | Ｃｄ８０細胞外ドメインポリペプチドと、がん治療でのそれらの使用 |
| CA3007110C (en) * | 2015-12-03 | 2025-07-08 | Shanghai Aeon Biotech Co Ltd | HETEROCYCLIC COMPOUNDS AND THEIR USES |
| WO2017096095A1 (en) * | 2015-12-03 | 2017-06-08 | Shanghai Aeon Biotech Co., Ltd. | Thieno-pyrimidine derivatives and uses thereof |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| US12390467B2 (en) * | 2018-04-13 | 2025-08-19 | The University Of Toledo | Necroptosis inducers or autophagy inhibitors or a combination thereof |
| WO2022099284A1 (en) * | 2020-11-05 | 2022-05-12 | Young Biopharma, Llc | Novel capsaicin analogs and uses thereof |
| WO2025140721A1 (zh) * | 2023-12-28 | 2025-07-03 | 粤港澳大湾区精准医学研究院(广州) | 腙类化合物、其药物组合物及其应用 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1057612B (de) | 1955-08-26 | 1959-05-21 | Bodo Lehmann | Kraftmaschine zur Erzeugung einer Drehbewegung durch ein Gas-, Dampf- oder Fluessigkeits-Druckmedium oder fuer den umgekehrten Prozess |
| DE1470356A1 (de) | 1964-01-15 | 1970-04-30 | Thomae Gmbh Dr K | Neue Thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
| GB1570494A (en) | 1975-11-28 | 1980-07-02 | Ici Ltd | Thienopyrimidine derivatives and their use as pesticides |
| ZA782648B (en) * | 1977-05-23 | 1979-06-27 | Ici Australia Ltd | The prevention,control or eradication of infestations of ixodid ticks |
| FR2447494A1 (fr) | 1979-01-24 | 1980-08-22 | Mecanismes Comp Ind De | Dispositif de reglage de la position d'un element deplacable dans un vehicule, tel que le siege de celui-ci |
| CH635167A5 (de) | 1979-01-25 | 1983-03-15 | Sulzer Ag | Einspritzeinrichtung eines dieselmotorzylinders. |
| GB2043061B (en) * | 1979-03-05 | 1983-05-11 | Ici Ltd | Thienopyrimidine and quinazoline derivatives |
| JPS5942387A (ja) | 1982-07-21 | 1984-03-08 | Sankyo Co Ltd | チエノピリミジン誘導体および殺虫、殺ダニ剤 |
| HU200330B (en) | 1985-03-14 | 1990-05-28 | Sankyo Co | Acaricides, ovicides, larvicides and aphicides and process for producing the new phenoxyalkyl-aminopyrimidine derivative active ingredients |
| DE3716131A1 (de) | 1987-05-14 | 1988-12-01 | Forsch Borstel Inst Fuer Exper | Substituierte 2-acylpyridin-(alpha)-(n)-hetarylhydrazone sowie diese enthaltende arzneimittel |
| JPH0720943B2 (ja) | 1988-08-19 | 1995-03-08 | 宇部興産株式会社 | アミノピリミジン誘導体、その製法及び殺虫・殺菌剤 |
| DE4008726A1 (de) | 1990-03-19 | 1991-09-26 | Basf Ag | Thieno(2,3-d)pyrimidinderivate |
| AU651337B2 (en) | 1990-03-30 | 1994-07-21 | Dowelanco | Thienopyrimidine derivatives |
| US5877178A (en) * | 1991-04-08 | 1999-03-02 | Duquesne University Of The Holy Ghost | Pyrimidine derivatives and methods of making and using these derivatives |
| EP0519211A1 (de) | 1991-05-17 | 1992-12-23 | Hoechst Schering AgrEvo GmbH | Substituierte 4-Aminopyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| IL112249A (en) * | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
| ATE159257T1 (de) * | 1994-05-03 | 1997-11-15 | Ciba Geigy Ag | Pyrrolopyrimidinderivate mit antiproliferativer wirkung |
| FI971974L (fi) | 1994-11-08 | 1997-06-18 | Takeda Chemical Industries Ltd | Tienopyridiini- tai tienopyrimidiinijohdannaiset ja niiden käyttö |
| US5639757A (en) * | 1995-05-23 | 1997-06-17 | Pfizer Inc. | 4-aminopyrrolo[2,3-d]pyrimidines as tyrosine kinase inhibitors |
| US5593997A (en) * | 1995-05-23 | 1997-01-14 | Pfizer Inc. | 4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase inhibitors |
| WO1997009878A1 (en) | 1995-09-15 | 1997-03-20 | Scriptgen Pharmaceuticals, Inc. | Arylhydrazone derivatives useful as antibacterial agents |
| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| ATE208395T1 (de) * | 1996-02-07 | 2001-11-15 | Janssen Pharmaceutica Nv | Thiophenopyrimidine |
| WO1999024440A1 (en) | 1997-11-11 | 1999-05-20 | Pfizer Products Inc. | Thienopyrimidine and thienopyridine derivatives useful as anticancer agents |
| US6451792B1 (en) | 1998-09-22 | 2002-09-17 | Ishihara Sangyo Kaisha Ltd. | Medical composition containing nitroetheneamine derivative or salt thereof as active constituent |
| US5948911A (en) * | 1998-11-20 | 1999-09-07 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to thienopyrimidine derivatives |
| DE60036812T2 (de) | 1999-07-07 | 2008-07-17 | Astrazeneca Uk Ltd. | Chinazolin derivate |
| US6313168B1 (en) * | 1999-12-15 | 2001-11-06 | Allergan Sales, Inc. | Use of retinoid receptor antagonists in the treatment of cartilage and bone pathologies |
| US6276782B1 (en) | 2000-01-11 | 2001-08-21 | Eastman Kodak Company | Assisted drop-on-demand inkjet printer |
| US7498335B2 (en) | 2000-03-06 | 2009-03-03 | Astrazeneca Ab | Method of producing an antiangiogenic or vascular permeability reducing effect |
| US20060004002A1 (en) * | 2004-07-02 | 2006-01-05 | Thomas Thrash | Small molecule thienopyrimidine-based protein tyrosine kinase inhibitors |
-
2000
- 2000-10-23 US US09/694,145 patent/US6503914B1/en not_active Ceased
-
2001
- 2001-10-23 AU AU2002246817A patent/AU2002246817B2/en not_active Ceased
- 2001-10-23 CA CA002426775A patent/CA2426775A1/en not_active Abandoned
- 2001-10-23 WO PCT/US2001/050198 patent/WO2002057271A2/en not_active Ceased
- 2001-10-23 KR KR10-2003-7005566A patent/KR20030040554A/ko not_active Abandoned
- 2001-10-23 EP EP01994425A patent/EP1409491A2/en not_active Withdrawn
- 2001-10-23 MX MXPA03003580A patent/MXPA03003580A/es not_active Application Discontinuation
- 2001-10-23 US US10/399,816 patent/US7285556B2/en not_active Expired - Fee Related
- 2001-10-23 JP JP2002557948A patent/JP2004517898A/ja active Pending
-
2004
- 2004-06-28 US US10/878,140 patent/USRE39267E1/en not_active Expired - Fee Related
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