DE602004007239T2 - 4-AMINOTHIENO[2,3-d] PYRIMIDIN -6-CARBONITRIL-DERIVATIVE ZUR VERWENDUNG ALS PDE7-INHIBITOREN - Google Patents

Info

Publication number

DE602004007239T2

DE602004007239T2 DE602004007239T DE602004007239T DE602004007239T2 DE 602004007239 T2 DE602004007239 T2 DE 602004007239T2 DE 602004007239 T DE602004007239 T DE 602004007239T DE 602004007239 T DE602004007239 T DE 602004007239T DE 602004007239 T2 DE602004007239 T2 DE 602004007239T2

Authority

DE

Germany

Prior art keywords

methyl

pyrimidine

carbonitrile

thieno

amino

Prior art date

2003-01-23

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.)

Expired - Lifetime

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• MLXWQNSUOXNSER-UHFFFAOYSA-N 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile Chemical class NC1=NC=NC2=C1C=C(C#N)S2 MLXWQNSUOXNSER-UHFFFAOYSA-N 0.000 title abstract description 4
• 229940123304 Phosphodiesterase 7 inhibitor Drugs 0.000 title description 6
• 239000002606 phosphodiesterase VII inhibitor Substances 0.000 title description 6
• 238000002360 preparation method Methods 0.000 claims abstract description 26
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 238000000034 method Methods 0.000 claims abstract description 15
• 230000005764 inhibitory process Effects 0.000 claims abstract description 12
• 150000003839 salts Chemical class 0.000 claims abstract description 12
• 230000001575 pathological effect Effects 0.000 claims abstract description 9
• 230000002265 prevention Effects 0.000 claims abstract description 8
• 230000008569 process Effects 0.000 claims abstract description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 101100407335 Dictyostelium discoideum pde7 gene Proteins 0.000 claims abstract 3
• -1 acyl radical Chemical class 0.000 claims description 193
• 125000001424 substituent group Chemical group 0.000 claims description 64
• 150000001875 compounds Chemical class 0.000 claims description 61
• 125000000217 alkyl group Chemical group 0.000 claims description 49
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• 125000004432 carbon atom Chemical group C* 0.000 claims description 37
• 125000005843 halogen group Chemical group 0.000 claims description 37
• 239000000203 mixture Substances 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 150000003254 radicals Chemical class 0.000 claims description 28
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• 125000002252 acyl group Chemical group 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 239000001301 oxygen Chemical group 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000004414 alkyl thio group Chemical group 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000004104 aryloxy group Chemical group 0.000 claims description 14
• 238000006243 chemical reaction Methods 0.000 claims description 14
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• 229910052717 sulfur Chemical group 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 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
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 238000001816 cooling Methods 0.000 claims description 8
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• GFZLEUSLQORNJJ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine 5-oxide Chemical compound C1=NC=C2S(=O)C=CC2=N1 GFZLEUSLQORNJJ-UHFFFAOYSA-N 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• 125000004442 acylamino group Chemical group 0.000 claims description 7
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000011593 sulfur Chemical group 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 230000006872 improvement Effects 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 150000005840 aryl radicals Chemical class 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000003367 polycyclic group Chemical group 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• QKRVOGZPQVCVPZ-UHFFFAOYSA-N 2-chlorothieno[3,2-d]pyrimidine Chemical compound ClC1=NC=C2SC=CC2=N1 QKRVOGZPQVCVPZ-UHFFFAOYSA-N 0.000 claims description 4
• YXTLFUJDTXUANL-UHFFFAOYSA-N 5-methyl-4-(4-methylpiperazin-1-yl)-2-[4-(trifluoromethyl)phenyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1CN(C)CCN1C1=NC(C=2C=CC(=CC=2)C(F)(F)F)=NC2=C1C(C)=C(C#N)S2 YXTLFUJDTXUANL-UHFFFAOYSA-N 0.000 claims description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• 208000011231 Crohn disease Diseases 0.000 claims description 4
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
• 208000028018 Lymphocytic leukaemia Diseases 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 201000008937 atopic dermatitis Diseases 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 239000012320 chlorinating reagent Substances 0.000 claims description 4
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 208000003747 lymphoid leukemia Diseases 0.000 claims description 4
• 210000000056 organ Anatomy 0.000 claims description 4
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 4
• ZIEWSZYVEDTXGH-UHFFFAOYSA-N pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC=N1 ZIEWSZYVEDTXGH-UHFFFAOYSA-N 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 238000002054 transplantation Methods 0.000 claims description 4
• IKCMMPOWDCWWJS-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-[ethyl(methyl)amino]-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(C)CC)=NC=1C1=CC=C(OC)C(OC)=C1 IKCMMPOWDCWWJS-UHFFFAOYSA-N 0.000 claims description 3
• SMMQAGYVPPXWAV-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-4-[2-hydroxyethyl(methyl)amino]-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=CC(OC)=CC(C=2N=C3SC(=C(C)C3=C(N(C)CCO)N=2)C#N)=C1 SMMQAGYVPPXWAV-UHFFFAOYSA-N 0.000 claims description 3
• BVBKUCXOVHVRKF-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-methyl-4-(4-methylpiperazin-1-yl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1CN(C)CCN1C1=NC(C=2C=CC(Cl)=CC=2)=NC2=C1C(C)=C(C#N)S2 BVBKUCXOVHVRKF-UHFFFAOYSA-N 0.000 claims description 3
• QRVVYGXZCAJWNO-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methyl]-4-(2-hydroxyethylamino)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC(NCCO)=C(C(C)=C(S2)C#N)C2=N1 QRVVYGXZCAJWNO-UHFFFAOYSA-N 0.000 claims description 3
• 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
• HFPPGJOHOAMLPW-UHFFFAOYSA-N 4-(3,5-dimethylpiperazin-1-yl)-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(N3CC(C)NC(C)C3)N=2)C#N)=C1 HFPPGJOHOAMLPW-UHFFFAOYSA-N 0.000 claims description 3
• IZOQYLTWGDRQIZ-UHFFFAOYSA-N 4-(4-acetylpiperazin-1-yl)-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(N3CCN(CC3)C(C)=O)N=2)C#N)=C1 IZOQYLTWGDRQIZ-UHFFFAOYSA-N 0.000 claims description 3
• AWXXKHKQDQFYMW-UHFFFAOYSA-N 4-(diethylamino)-5-methyl-2-[4-(trifluoromethyl)phenyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1C1=CC=C(C(F)(F)F)C=C1 AWXXKHKQDQFYMW-UHFFFAOYSA-N 0.000 claims description 3
• MYJKZQFEQHKVMG-UHFFFAOYSA-N 4-[2-hydroxyethyl(methyl)amino]-2-(4-methoxyphenyl)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=NC(N(C)CCO)=C(C(C)=C(S2)C#N)C2=N1 MYJKZQFEQHKVMG-UHFFFAOYSA-N 0.000 claims description 3
• WCQOHGSGYPEMRV-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)-4-(4-methylpiperazin-1-yl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1CN(C)CCN1C1=NC(C=2C=CC(C)=CC=2)=NC2=C1C(C)=C(C#N)S2 WCQOHGSGYPEMRV-UHFFFAOYSA-N 0.000 claims description 3
• KGCTYTHVLIWNQH-UHFFFAOYSA-N 5-methyl-4-(pentan-3-ylamino)-2-[(3,4,5-trimethoxyphenyl)methyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(NC(CC)CC)=NC=1CC1=CC(OC)=C(OC)C(OC)=C1 KGCTYTHVLIWNQH-UHFFFAOYSA-N 0.000 claims description 3
• KUOGGIYPIJQDBQ-UHFFFAOYSA-N 5-methyl-4-morpholin-4-yl-2-phenylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C=12C(C)=C(C#N)SC2=NC(C=2C=CC=CC=2)=NC=1N1CCOCC1 KUOGGIYPIJQDBQ-UHFFFAOYSA-N 0.000 claims description 3
• 229940121359 adenosine receptor antagonist Drugs 0.000 claims description 3
• 229940111134 coxibs Drugs 0.000 claims description 3
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 3
• 208000026278 immune system disease Diseases 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 3
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 3
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 3
• 150000003431 steroids Chemical class 0.000 claims description 3
• 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 claims description 3
• 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 claims description 3
• INMGGJUXBXMTPH-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-4-[2-hydroxyethyl(methyl)amino]-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=C2OCOC2=CC(C=2N=C(C=3C(C)=C(C#N)SC=3N=2)N(CCO)C)=C1 INMGGJUXBXMTPH-UHFFFAOYSA-N 0.000 claims description 2
• XMYYFMNNKDVTDK-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-methyl-4-(4-methylpiperazin-1-yl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1CN(C)CCN1C1=NC(C=2C=C3OCOC3=CC=2)=NC2=C1C(C)=C(C#N)S2 XMYYFMNNKDVTDK-UHFFFAOYSA-N 0.000 claims description 2
• YOCRZATXEAWCOM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-methyl-4-(4-methylpiperazin-1-yl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(N2CCN(C)CC2)=C(C(C)=C(S2)C#N)C2=N1 YOCRZATXEAWCOM-UHFFFAOYSA-N 0.000 claims description 2
• SGPGVVRRKMMOBF-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-4-[ethyl(methyl)amino]-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(C)CC)=NC=1C1=CC(OC)=CC(OC)=C1 SGPGVVRRKMMOBF-UHFFFAOYSA-N 0.000 claims description 2
• PYBSHIOPUAQAFH-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methyl]-4-(2-methoxyethylamino)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(NCCOC)=NC=1CC1=CC=C(OC)C(OC)=C1 PYBSHIOPUAQAFH-UHFFFAOYSA-N 0.000 claims description 2
• JAQNKJVLSPGYPD-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methyl]-4-[2-hydroxyethyl(methyl)amino]-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC(N(C)CCO)=C(C(C)=C(S2)C#N)C2=N1 JAQNKJVLSPGYPD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• HZSIPQBOEAQXKM-UHFFFAOYSA-N 4-(2-hydroxyethylamino)-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(NCCO)N=2)C#N)=C1 HZSIPQBOEAQXKM-UHFFFAOYSA-N 0.000 claims description 2
• GGJGQGPSISDQPB-UHFFFAOYSA-N 4-(butan-2-ylamino)-5-methyl-2-[(3,4,5-trimethoxyphenyl)methyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(NC(C)CC)=NC=1CC1=CC(OC)=C(OC)C(OC)=C1 GGJGQGPSISDQPB-UHFFFAOYSA-N 0.000 claims description 2
• TVWVAYRXDFCMRD-UHFFFAOYSA-N 4-(cyclobutylamino)-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(NC3CCC3)N=2)C#N)=C1 TVWVAYRXDFCMRD-UHFFFAOYSA-N 0.000 claims description 2
• KVBZAWKMFWCFQW-UHFFFAOYSA-N 4-(cyclopentylamino)-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(NC3CCCC3)N=2)C#N)=C1 KVBZAWKMFWCFQW-UHFFFAOYSA-N 0.000 claims description 2
• BNLFDSPSMZJSQB-UHFFFAOYSA-N 4-(cyclopropylamino)-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(NC3CC3)N=2)C#N)=C1 BNLFDSPSMZJSQB-UHFFFAOYSA-N 0.000 claims description 2
• JUGJHAOQZFVRKX-UHFFFAOYSA-N 4-(diethylamino)-2-[(3,4-dimethoxyphenyl)methyl]-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1CC1=CC=C(OC)C(OC)=C1 JUGJHAOQZFVRKX-UHFFFAOYSA-N 0.000 claims description 2
• FPYPVYUQMBQLCF-UHFFFAOYSA-N 4-(diethylamino)-5-methyl-2-(4-methylphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1C1=CC=C(C)C=C1 FPYPVYUQMBQLCF-UHFFFAOYSA-N 0.000 claims description 2
• YQDLVYQTNPKBIZ-UHFFFAOYSA-N 4-(diethylamino)-5-methyl-2-[(3,4,5-trimethoxyphenyl)methyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1CC1=CC(OC)=C(OC)C(OC)=C1 YQDLVYQTNPKBIZ-UHFFFAOYSA-N 0.000 claims description 2
• QMHDGVJYDHFMGR-UHFFFAOYSA-N 4-(tert-butylamino)-5-methyl-2-[(3,4,5-trimethoxyphenyl)methyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(CC=2N=C3SC(=C(C)C3=C(NC(C)(C)C)N=2)C#N)=C1 QMHDGVJYDHFMGR-UHFFFAOYSA-N 0.000 claims description 2
• BQYJVJMQMUMTDD-UHFFFAOYSA-N 4-[2-aminoethyl(methyl)amino]-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(N(C)CCN)N=2)C#N)=C1 BQYJVJMQMUMTDD-UHFFFAOYSA-N 0.000 claims description 2
• SEVFMCGNVGIXRV-UHFFFAOYSA-N 4-[2-hydroxyethyl(methyl)amino]-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(N(C)CCO)N=2)C#N)=C1 SEVFMCGNVGIXRV-UHFFFAOYSA-N 0.000 claims description 2
• SRVAMEUZJOSGMF-UHFFFAOYSA-N 5-methyl-4-(1,2,4-triazol-1-yl)-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(N3N=CN=C3)N=2)C#N)=C1 SRVAMEUZJOSGMF-UHFFFAOYSA-N 0.000 claims description 2
• UFJVXHFPPKRMFY-UHFFFAOYSA-N 5-methyl-4-(2-methylpropylamino)-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(NCC(C)C)N=2)C#N)=C1 UFJVXHFPPKRMFY-UHFFFAOYSA-N 0.000 claims description 2
• AJLGLYHJZPRUSR-UHFFFAOYSA-N 5-methyl-4-(2-methylpropylamino)-2-[(3,4,5-trimethoxyphenyl)methyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(CC=2N=C3SC(=C(C)C3=C(NCC(C)C)N=2)C#N)=C1 AJLGLYHJZPRUSR-UHFFFAOYSA-N 0.000 claims description 2
• DZSLMOWBMHVNAW-UHFFFAOYSA-N 5-methyl-4-(3-methylpiperazin-1-yl)-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(N3CC(C)NCC3)N=2)C#N)=C1 DZSLMOWBMHVNAW-UHFFFAOYSA-N 0.000 claims description 2
• NYJOYVZSRCHFLE-UHFFFAOYSA-N 5-methyl-4-(4-methylpiperazin-1-yl)-2-[(3,4,5-trimethoxyphenyl)methyl]thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(CC=2N=C3SC(=C(C)C3=C(N3CCN(C)CC3)N=2)C#N)=C1 NYJOYVZSRCHFLE-UHFFFAOYSA-N 0.000 claims description 2
• ZMUVFWXJPDQXSC-UHFFFAOYSA-N 5-methyl-4-(triazol-2-yl)-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3SC(=C(C)C3=C(N3N=CC=N3)N=2)C#N)=C1 ZMUVFWXJPDQXSC-UHFFFAOYSA-N 0.000 claims description 2
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