JP2006515604A - Ｐｄｅ７阻害剤としての４−アミノチエノ［２，３−ｄ］ピリミジン−６−カルボニトリル誘導体 - Google Patents
Ｐｄｅ７阻害剤としての４−アミノチエノ［２，３−ｄ］ピリミジン−６−カルボニトリル誘導体 Download PDFInfo
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- JP2006515604A JP2006515604A JP2006500010A JP2006500010A JP2006515604A JP 2006515604 A JP2006515604 A JP 2006515604A JP 2006500010 A JP2006500010 A JP 2006500010A JP 2006500010 A JP2006500010 A JP 2006500010A JP 2006515604 A JP2006515604 A JP 2006515604A
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- Prior art keywords
- methyl
- pyrimidine
- carbonitrile
- thieno
- amino
- 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.)
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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
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 230000005764 inhibitory process Effects 0.000 claims abstract description 13
- 230000001575 pathological effect Effects 0.000 claims abstract description 9
- 230000002265 prevention Effects 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 4
- 101100407335 Dictyostelium discoideum pde7 gene Proteins 0.000 claims abstract 4
- -1 cyano, difluoromethoxy Chemical group 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group 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
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 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 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 229910052717 sulfur 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
- 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
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- BJGIOIKJRNCHMD-UHFFFAOYSA-N thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N1=CN=C2SC(C#N)=CC2=C1 BJGIOIKJRNCHMD-UHFFFAOYSA-N 0.000 claims description 5
- 238000002054 transplantation Methods 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- MXHMNVQEUAIACY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-4-piperazin-1-ylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=NC(N2CCNCC2)=C(C(C)=C(S2)C#N)C2=N1 MXHMNVQEUAIACY-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- AFIJMIAUEXHZJE-UHFFFAOYSA-N 4-(4-ethylpiperazin-1-yl)-2-(4-methoxyphenyl)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1CN(CC)CCN1C1=NC(C=2C=CC(OC)=CC=2)=NC2=C1C(C)=C(C#N)S2 AFIJMIAUEXHZJE-UHFFFAOYSA-N 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 230000001668 ameliorated effect Effects 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 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 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
- CHAUXYGEOWNCBN-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-4-piperidin-1-ylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=NC(N2CCCCC2)=C(C(C)=C(S2)C#N)C2=N1 CHAUXYGEOWNCBN-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
- ABRDCRCBFJXWAV-UHFFFAOYSA-N 4-(2-hydroxyethylamino)-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(NCCO)N=2)C#N)=C1 ABRDCRCBFJXWAV-UHFFFAOYSA-N 0.000 claims description 3
- PQLFSTRYYREDAO-UHFFFAOYSA-N 4-(2-methoxyethylamino)-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(NCCOC)=NC=1C1=CC(OC)=C(OC)C(OC)=C1 PQLFSTRYYREDAO-UHFFFAOYSA-N 0.000 claims description 3
- HBPKWOUXTQAUGM-UHFFFAOYSA-N 4-(2-methoxyethylamino)-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(NCCOC)=NC=1CC1=CC(OC)=C(OC)C(OC)=C1 HBPKWOUXTQAUGM-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
- MJPJPKCTXAWRCA-UHFFFAOYSA-N 4-(4-ethylpiperazin-1-yl)-5-methyl-2-phenylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1CN(CC)CCN1C1=NC(C=2C=CC=CC=2)=NC2=C1C(C)=C(C#N)S2 MJPJPKCTXAWRCA-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- UHGYRGGYFUCGTM-UHFFFAOYSA-N 4-(diethylamino)-5-methyl-2-(3,4,5-trimethoxyphenyl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1C1=CC(OC)=C(OC)C(OC)=C1 UHGYRGGYFUCGTM-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- QBDNAWNFHXEOLA-UHFFFAOYSA-N 4-(diethylamino)-5-methyl-2-phenylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1C1=CC=CC=C1 QBDNAWNFHXEOLA-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- WUFSOXBAZDBOOL-UHFFFAOYSA-N 4-[ethyl(methyl)amino]-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(C)CC)=NC=1CC1=CC(OC)=C(OC)C(OC)=C1 WUFSOXBAZDBOOL-UHFFFAOYSA-N 0.000 claims description 3
- FKOVOQPSMIFBSZ-UHFFFAOYSA-N 4-imidazol-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(N3C=NC=C3)N=2)C#N)=C1 FKOVOQPSMIFBSZ-UHFFFAOYSA-N 0.000 claims description 3
- KSKQKROHYCQRPK-UHFFFAOYSA-N 5-methyl-2-(4-nitrophenyl)-4-piperidin-1-ylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C=12C(C)=C(C#N)SC2=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=NC=1N1CCCCC1 KSKQKROHYCQRPK-UHFFFAOYSA-N 0.000 claims description 3
- CRBOERJSUDKWMU-UHFFFAOYSA-N 5-methyl-2-phenyl-4-piperidin-1-ylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C=12C(C)=C(C#N)SC2=NC(C=2C=CC=CC=2)=NC=1N1CCCCC1 CRBOERJSUDKWMU-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- CNNVNRVXFGKDEH-UHFFFAOYSA-N 5-methyl-4-(4-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(N3CCN(C)CC3)N=2)C#N)=C1 CNNVNRVXFGKDEH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- DYTQOXGIOIAWHB-UHFFFAOYSA-N 5-methyl-4-morpholin-4-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(N3CCOCC3)N=2)C#N)=C1 DYTQOXGIOIAWHB-UHFFFAOYSA-N 0.000 claims description 3
- 229940121359 adenosine receptor antagonist Drugs 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- 229940111134 coxibs Drugs 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 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
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 claims description 3
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 claims description 3
- IKIPDPGMDSDNRL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-(dimethylamino)-5-methylthieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(N(C)C)=C(C(C)=C(S2)C#N)C2=N1 IKIPDPGMDSDNRL-UHFFFAOYSA-N 0.000 claims description 2
- JLNSMBNURYWJIA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-methyl-4-(propylamino)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound N=1C=2SC(C#N)=C(C)C=2C(NCCC)=NC=1C1=CC=C(OC)C(OC)=C1 JLNSMBNURYWJIA-UHFFFAOYSA-N 0.000 claims description 2
- QXVRFMVYBYHJIY-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methyl]-5-methyl-4-(4-methylpiperazin-1-yl)thieno[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC(N2CCN(C)CC2)=C(C(C)=C(S2)C#N)C2=N1 QXVRFMVYBYHJIY-UHFFFAOYSA-N 0.000 claims description 2
- NTFHIQBTKYWJSO-UHFFFAOYSA-N 2-benzyl-4-(diethylamino)-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=CC=C1 NTFHIQBTKYWJSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
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- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- RAPBKOVOVARHKD-UHFFFAOYSA-N methyl 4-[6-cyano-4-(diethylamino)-5-methylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(CC)CC)=NC=1C1=CC=C(C(=O)OC)C=C1 RAPBKOVOVARHKD-UHFFFAOYSA-N 0.000 description 1
- OKAJGNBYESUAJU-UHFFFAOYSA-N methyl 4-[6-cyano-4-[ethyl(methyl)amino]-5-methylthieno[2,3-d]pyrimidin-2-yl]benzoate Chemical compound N=1C=2SC(C#N)=C(C)C=2C(N(C)CC)=NC=1C1=CC=C(C(=O)OC)C=C1 OKAJGNBYESUAJU-UHFFFAOYSA-N 0.000 description 1
- KKZMIDYKRKGJHG-UHFFFAOYSA-N methyl 4-cyanobenzoate Chemical compound COC(=O)C1=CC=C(C#N)C=C1 KKZMIDYKRKGJHG-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940074355 nitric acid Drugs 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
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- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
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- 239000008188 pellet Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005522 programmed cell death Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- NRAOLILGQIRZBT-UHFFFAOYSA-N thieno[2,3-d]pyrimidin-2-amine Chemical class NC1=NC=C2C=CSC2=N1 NRAOLILGQIRZBT-UHFFFAOYSA-N 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- 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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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Neurology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200300172A ES2217956B1 (es) | 2003-01-23 | 2003-01-23 | Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo. |
| PCT/EP2004/000584 WO2004065391A1 (en) | 2003-01-23 | 2004-01-23 | 4-AMINOTHIENO[2,3-d]PYRIMIDINE-6-CARBONITRILE DERIVATIVES AS PDE7 INHIBITORS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006515604A true JP2006515604A (ja) | 2006-06-01 |
| JP2006515604A5 JP2006515604A5 (enExample) | 2007-01-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006500010A Pending JP2006515604A (ja) | 2003-01-23 | 2004-01-23 | Ｐｄｅ７阻害剤としての４−アミノチエノ［２，３−ｄ］ピリミジン−６−カルボニトリル誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7662814B2 (enExample) |
| EP (1) | EP1590352B1 (enExample) |
| JP (1) | JP2006515604A (enExample) |
| CN (1) | CN100582112C (enExample) |
| AT (1) | ATE365742T1 (enExample) |
| DE (1) | DE602004007239T2 (enExample) |
| ES (2) | ES2217956B1 (enExample) |
| WO (1) | WO2004065391A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006523238A (ja) * | 2003-04-09 | 2006-10-12 | エクセリクシス， インク． | Ｔｉｅ−２モジュレータと使用方法 |
| JP2010512337A (ja) * | 2006-12-07 | 2010-04-22 | ジェネンテック インコーポレイテッド | ホスホイノシチド３−キナーゼ阻害剤化合物及び使用方法 |
| JP2010540458A (ja) * | 2007-09-24 | 2010-12-24 | ジェネンテック， インコーポレイテッド | チアゾロピリミジンｐｉ３ｋ阻害剤化合物および使用方法 |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2006040966A1 (ja) * | 2004-10-08 | 2006-04-20 | Astellas Pharma Inc. | 芳香環縮合ピリミジン誘導体 |
| TW200621257A (en) * | 2004-10-20 | 2006-07-01 | Astellas Pharma Inc | Pyrimidine derivative fused with nonaromatic ring |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| JP2009532375A (ja) * | 2006-03-30 | 2009-09-10 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| AU2007243466B2 (en) | 2006-04-26 | 2012-01-19 | F. Hoffmann-La Roche Ag | Phosphoinositide 3-kinase inhibitor compounds and pharmaceutical compositions containing them |
| PL2041139T3 (pl) | 2006-04-26 | 2012-05-31 | Hoffmann La Roche | Związki farmaceutyczne |
| KR101533461B1 (ko) | 2006-04-26 | 2015-07-02 | 에프. 호프만-라 로슈 아게 | Ｐｉ３ｋ저해제로 유용한 티에노［3,2-ｄ］피리미딘 유도체 |
| GB0608820D0 (en) * | 2006-05-04 | 2006-06-14 | Piramed Ltd | Pharmaceutical compounds |
| EP2043654A2 (en) * | 2006-06-12 | 2009-04-08 | Vertex Pharmaceuticals, Inc. | Thienopyrimidines useful as modulators of ion channels |
| PE20081679A1 (es) * | 2006-12-07 | 2008-12-18 | Hoffmann La Roche | Compuestos del inhibidor de fosfoinositida 3-cinasa y metodos de uso |
| MX2009010450A (es) | 2007-03-27 | 2009-11-23 | Omeros Corp | El uso de inhibidores de la fosfodiesterasa 7 para el tratamiento transtornos del movimiento. |
| US8637528B2 (en) * | 2007-03-27 | 2014-01-28 | Omeros Corporation | Use of PDE7 inhibitors for the treatment of movement disorders |
| BRPI0816769A2 (pt) | 2007-09-12 | 2016-11-29 | Hoffmann La Roche | combinações de compostos inibidores de fosfoinositida 3-cinase e agentes quimioterapêuticos, e métodos de uso |
| WO2009055730A1 (en) | 2007-10-25 | 2009-04-30 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| GB0721095D0 (en) | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| US20100093702A1 (en) * | 2008-10-13 | 2010-04-15 | Barbay J Kent | METHYLENE AMINES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| US20100093714A1 (en) * | 2008-10-13 | 2010-04-15 | Devraj Chakravarty | AMIDES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| EP2923734B1 (en) * | 2009-03-13 | 2018-01-10 | Katholieke Universiteit Leuven, K.U. Leuven R&D | Purine analogues and their use as immunosuppressive agents |
| SG182247A1 (en) * | 2009-05-27 | 2012-08-30 | Hoffmann La Roche | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| MX2011012520A (es) | 2009-05-27 | 2011-12-12 | Hoffmann La Roche | Compuestos inhibidores de pi3k de pirimidina biciclicos selectivos para p110 delta y metodos de uso de los mismos. |
| CN103119047B (zh) | 2010-07-23 | 2016-06-15 | 哈佛大学校长及研究员协会 | 三环类蛋白酶体活性增强化合物 |
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- 2004-01-23 AT AT04704579T patent/ATE365742T1/de not_active IP Right Cessation
- 2004-01-23 JP JP2006500010A patent/JP2006515604A/ja active Pending
- 2004-01-23 CN CN200480007362A patent/CN100582112C/zh not_active Expired - Fee Related
- 2004-01-23 WO PCT/EP2004/000584 patent/WO2004065391A1/en not_active Ceased
- 2004-01-23 ES ES04704579T patent/ES2289475T3/es not_active Expired - Lifetime
- 2004-01-23 DE DE602004007239T patent/DE602004007239T2/de not_active Expired - Lifetime
- 2004-01-23 EP EP04704579A patent/EP1590352B1/en not_active Expired - Lifetime
- 2004-01-23 US US10/542,940 patent/US7662814B2/en not_active Expired - Fee Related
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| US6133271A (en) * | 1998-11-19 | 2000-10-17 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives |
| WO2002026745A1 (en) * | 2000-09-29 | 2002-04-04 | Nippon Soda Co., Ltd. | Thienopyrimidine compounds and their salts and process for preparation of both |
| WO2002088138A1 (en) * | 2001-04-30 | 2002-11-07 | Bayer Corporation | Novel 4-amino-5,6-substituted thiopheno[2,3-d]pyrimidines |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2006523238A (ja) * | 2003-04-09 | 2006-10-12 | エクセリクシス， インク． | Ｔｉｅ−２モジュレータと使用方法 |
| JP4895806B2 (ja) * | 2003-04-09 | 2012-03-14 | エクセリクシス， インク． | Ｔｉｅ−２モジュレータと使用方法 |
| JP2010512337A (ja) * | 2006-12-07 | 2010-04-22 | ジェネンテック インコーポレイテッド | ホスホイノシチド３−キナーゼ阻害剤化合物及び使用方法 |
| JP2010540458A (ja) * | 2007-09-24 | 2010-12-24 | ジェネンテック， インコーポレイテッド | チアゾロピリミジンｐｉ３ｋ阻害剤化合物および使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20060229306A1 (en) | 2006-10-12 |
| DE602004007239D1 (de) | 2007-08-09 |
| CN100582112C (zh) | 2010-01-20 |
| US7662814B2 (en) | 2010-02-16 |
| EP1590352B1 (en) | 2007-06-27 |
| ES2217956B1 (es) | 2006-04-01 |
| ATE365742T1 (de) | 2007-07-15 |
| EP1590352A1 (en) | 2005-11-02 |
| CN1761671A (zh) | 2006-04-19 |
| ES2289475T3 (es) | 2008-02-01 |
| ES2217956A1 (es) | 2004-11-01 |
| DE602004007239T2 (de) | 2008-02-28 |
| WO2004065391A1 (en) | 2004-08-05 |
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