JP2009528389A5 - - Google Patents
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- JP2009528389A5 JP2009528389A5 JP2008557512A JP2008557512A JP2009528389A5 JP 2009528389 A5 JP2009528389 A5 JP 2009528389A5 JP 2008557512 A JP2008557512 A JP 2008557512A JP 2008557512 A JP2008557512 A JP 2008557512A JP 2009528389 A5 JP2009528389 A5 JP 2009528389A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydrothiopheno
- pyrimidine
- dione
- methyl
- ethyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229910052757 nitrogen Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 5
- 239000011593 sulfur Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- -1 1,3-oxazolin-2-yl Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- AYIMIOWWJQTGRR-UHFFFAOYSA-N 1,5-dimethyl-3-(2-methylpropyl)-6-(1,3-oxazol-2-yl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)N(C)C=2SC=1C1=NC=CO1 AYIMIOWWJQTGRR-UHFFFAOYSA-N 0.000 claims 1
- XSACIUDXRIJHPP-UHFFFAOYSA-N 1,5-dimethyl-3-prop-2-ynylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound CN1C(=O)N(CC#C)C(=O)C2=C1SC=C2C XSACIUDXRIJHPP-UHFFFAOYSA-N 0.000 claims 1
- QANGOZVMTSSFBT-VIFPVBQESA-N 1,5-dimethyl-6-[(4s)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]-3-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)N(C)C=2SC=1C1=N[C@@H](C)CO1 QANGOZVMTSSFBT-VIFPVBQESA-N 0.000 claims 1
- RJRSFBWAWVWPSE-SECBINFHSA-N 1,5-dimethyl-6-[(5r)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-3-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)N(C)C=2SC=1C1=NC[C@@H](C)O1 RJRSFBWAWVWPSE-SECBINFHSA-N 0.000 claims 1
- GYKMASORTIXMGF-UHFFFAOYSA-N 1-ethyl-6-(furan-2-yl)-5-methyl-3-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)N(CC)C=2SC=1C1=CC=CO1 GYKMASORTIXMGF-UHFFFAOYSA-N 0.000 claims 1
- RDMCECHQIVHPLV-UHFFFAOYSA-N 3,5-dimethyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound N1C(=O)N(C)C(=O)C2=C1SC=C2C RDMCECHQIVHPLV-UHFFFAOYSA-N 0.000 claims 1
- FXAQLDZSORIKFL-UHFFFAOYSA-N 3,5-dimethyl-6-thiophen-2-yl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound S1C=2NC(=O)N(C)C(=O)C=2C(C)=C1C1=CC=CS1 FXAQLDZSORIKFL-UHFFFAOYSA-N 0.000 claims 1
- DQOIGKIGTHFRPK-UHFFFAOYSA-N 3-(cyclopropylmethyl)-5-methyl-6-thiophen-2-yl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1C=2C(C)=C(C=3SC=CC=3)SC=2NC(=O)N1CC1CC1 DQOIGKIGTHFRPK-UHFFFAOYSA-N 0.000 claims 1
- FLVZBFGCVGNIJI-UHFFFAOYSA-N 3-(cyclopropylmethyl)-6-(furan-2-yl)-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1C=2C(C)=C(C=3OC=CC=3)SC=2NC(=O)N1CC1CC1 FLVZBFGCVGNIJI-UHFFFAOYSA-N 0.000 claims 1
- BGXYXSGIGDBGLB-UHFFFAOYSA-N 3-ethyl-1,5-dimethyl-6-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(C)C=2SC=1C1=NC=CS1 BGXYXSGIGDBGLB-UHFFFAOYSA-N 0.000 claims 1
- SYHSYRHGGSPNBV-UHFFFAOYSA-N 3-ethyl-1,5-dimethyl-6-(1h-pyrrol-2-yl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(C)C=2SC=1C1=CC=CN1 SYHSYRHGGSPNBV-UHFFFAOYSA-N 0.000 claims 1
- MWHXFQLBIPLRHU-UHFFFAOYSA-N 3-ethyl-1,5-dimethyl-6-(4-methylthiophen-2-yl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(C)C=2SC=1C1=CC(C)=CS1 MWHXFQLBIPLRHU-UHFFFAOYSA-N 0.000 claims 1
- LBYZFZDBAAUYAN-UHFFFAOYSA-N 3-ethyl-1,5-dimethyl-6-pyridin-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(C)C=2SC=1C1=CC=CC=N1 LBYZFZDBAAUYAN-UHFFFAOYSA-N 0.000 claims 1
- SYPYECJBYHRXAH-UHFFFAOYSA-N 3-ethyl-5,6-dimethyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1N(CC)C(=O)NC2=C1C(C)=C(C)S2 SYPYECJBYHRXAH-UHFFFAOYSA-N 0.000 claims 1
- CNIUKLMBKSPBTK-UHFFFAOYSA-N 3-ethyl-5-(furan-2-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(CC)C(=O)NC=2SC=C1C1=CC=CO1 CNIUKLMBKSPBTK-UHFFFAOYSA-N 0.000 claims 1
- HKDPFHNYMVTSDK-UHFFFAOYSA-N 3-ethyl-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1N(CC)C(=O)NC2=C1C(C)=CS2 HKDPFHNYMVTSDK-UHFFFAOYSA-N 0.000 claims 1
- XFMIKIFGGADBEX-UHFFFAOYSA-N 3-ethyl-5-methyl-6-(1,3-oxazol-2-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=NC=CO1 XFMIKIFGGADBEX-UHFFFAOYSA-N 0.000 claims 1
- FGSSLGCUVFSUQF-UHFFFAOYSA-N 3-ethyl-5-methyl-6-(1,3-thiazol-2-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=NC=CS1 FGSSLGCUVFSUQF-UHFFFAOYSA-N 0.000 claims 1
- VWPYAFLMACTLRC-UHFFFAOYSA-N 3-ethyl-5-methyl-6-(1h-pyrrol-2-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=CC=CN1 VWPYAFLMACTLRC-UHFFFAOYSA-N 0.000 claims 1
- ZAHFSDJSKSJCLX-UHFFFAOYSA-N 3-ethyl-5-methyl-6-(3-methylthiophen-2-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C=1SC=CC=1C ZAHFSDJSKSJCLX-UHFFFAOYSA-N 0.000 claims 1
- ANNNZGGUHBHDRB-UHFFFAOYSA-N 3-ethyl-5-methyl-6-(4-methylthiophen-2-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=CC(C)=CS1 ANNNZGGUHBHDRB-UHFFFAOYSA-N 0.000 claims 1
- JEVQRXBELYXZCN-UHFFFAOYSA-N 3-ethyl-5-methyl-6-pyridin-2-yl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=CC=CC=N1 JEVQRXBELYXZCN-UHFFFAOYSA-N 0.000 claims 1
- BQRWKTYJZMSGRG-UHFFFAOYSA-N 3-ethyl-5-methyl-6-thiophen-2-yl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=CC=CS1 BQRWKTYJZMSGRG-UHFFFAOYSA-N 0.000 claims 1
- USWYIELLUJCANN-UHFFFAOYSA-N 3-ethyl-5-methyl-6-thiophen-3-yl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C=1C=CSC=1 USWYIELLUJCANN-UHFFFAOYSA-N 0.000 claims 1
- QIHGXPWTOIPJBU-UHFFFAOYSA-N 3-ethyl-6-(2-methoxypyridin-3-yl)-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=CC=CN=C1OC QIHGXPWTOIPJBU-UHFFFAOYSA-N 0.000 claims 1
- YGGIDNUCBXJIFW-UHFFFAOYSA-N 3-ethyl-6-(6-methoxypyridin-3-yl)-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=CC=C(OC)N=C1 YGGIDNUCBXJIFW-UHFFFAOYSA-N 0.000 claims 1
- KOVVTTPRNSFLJW-UHFFFAOYSA-N 3-ethyl-6-(furan-2-yl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(C)C=2SC=1C1=CC=CO1 KOVVTTPRNSFLJW-UHFFFAOYSA-N 0.000 claims 1
- VBOJNVFLQMBIKM-UHFFFAOYSA-N 3-ethyl-6-(furan-2-yl)-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=CC=CO1 VBOJNVFLQMBIKM-UHFFFAOYSA-N 0.000 claims 1
- IFHHDEMGUPBEJJ-UHFFFAOYSA-N 3-ethyl-6-(furan-3-yl)-1,5-dimethylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(C)C=2SC=1C=1C=COC=1 IFHHDEMGUPBEJJ-UHFFFAOYSA-N 0.000 claims 1
- FIHCUITWGOZCGQ-UHFFFAOYSA-N 3-ethyl-6-(furan-3-yl)-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C=1C=COC=1 FIHCUITWGOZCGQ-UHFFFAOYSA-N 0.000 claims 1
- SIVMRDWPCWHXHT-UHFFFAOYSA-N 3-ethyl-n,5-dimethyl-2,4-dioxo-1h-thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(CC)C(=O)NC2=C1C(C)=C(C(=O)NC)S2 SIVMRDWPCWHXHT-UHFFFAOYSA-N 0.000 claims 1
- PCMWKHAVVPWRIN-UHFFFAOYSA-N 5-methyl-2,4-dioxo-3-propyl-1h-thieno[2,3-d]pyrimidine-6-carboxylic acid Chemical compound O=C1N(CCC)C(=O)NC2=C1C(C)=C(C(O)=O)S2 PCMWKHAVVPWRIN-UHFFFAOYSA-N 0.000 claims 1
- BXBGZNKUNTXGEO-UHFFFAOYSA-N 5-methyl-3-(2-methylpropyl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1N(CC(C)C)C(=O)NC2=C1C(C)=CS2 BXBGZNKUNTXGEO-UHFFFAOYSA-N 0.000 claims 1
- PHDWDSRETAHXQX-UHFFFAOYSA-N 5-methyl-3-(2-methylpropyl)-6-(1,3-oxazol-2-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)NC=2SC=1C1=NC=CO1 PHDWDSRETAHXQX-UHFFFAOYSA-N 0.000 claims 1
- BBTQJFJLGVRVGB-UHFFFAOYSA-N 5-methyl-3-(2-methylpropyl)-6-(1,3-oxazol-4-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)NC=2SC=1C1=COC=N1 BBTQJFJLGVRVGB-UHFFFAOYSA-N 0.000 claims 1
- CODHAALJGOWLRM-UHFFFAOYSA-N 5-methyl-3-prop-2-enyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound N1C(=O)N(CC=C)C(=O)C2=C1SC=C2C CODHAALJGOWLRM-UHFFFAOYSA-N 0.000 claims 1
- CAKRFHARQNNGOH-UHFFFAOYSA-N 5-methyl-3-prop-2-ynyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound N1C(=O)N(CC#C)C(=O)C2=C1SC=C2C CAKRFHARQNNGOH-UHFFFAOYSA-N 0.000 claims 1
- PHRDOZYOYVDPFF-SSDOTTSWSA-N 5-methyl-6-[(4r)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]-3-propyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CCC)C(=O)NC=2SC=1C1=N[C@H](C)CO1 PHRDOZYOYVDPFF-SSDOTTSWSA-N 0.000 claims 1
- HVKXGKCYOSLVRE-QMMMGPOBSA-N 5-methyl-6-[(4s)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]-3-(2-methylpropyl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)NC=2SC=1C1=N[C@@H](C)CO1 HVKXGKCYOSLVRE-QMMMGPOBSA-N 0.000 claims 1
- PHRDOZYOYVDPFF-ZETCQYMHSA-N 5-methyl-6-[(4s)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]-3-propyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CCC)C(=O)NC=2SC=1C1=N[C@@H](C)CO1 PHRDOZYOYVDPFF-ZETCQYMHSA-N 0.000 claims 1
- MPZOAJOWUXAAHQ-MRVPVSSYSA-N 5-methyl-6-[(5r)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-3-(2-methylpropyl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)NC=2SC=1C1=NC[C@@H](C)O1 MPZOAJOWUXAAHQ-MRVPVSSYSA-N 0.000 claims 1
- LDYRNWBGKMWMKV-UHFFFAOYSA-N 6-(1-benzylpyrazol-4-yl)-3-ethyl-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C(=C1)C=NN1CC1=CC=CC=C1 LDYRNWBGKMWMKV-UHFFFAOYSA-N 0.000 claims 1
- QDCJXMUGQRYYGC-UHFFFAOYSA-N 6-(3-benzyl-1,2,4-oxadiazol-5-yl)-3-ethyl-5-methyl-1H-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C(ON=1)=NC=1CC1=CC=CC=C1 QDCJXMUGQRYYGC-UHFFFAOYSA-N 0.000 claims 1
- GVSFJJXEFOKQEW-UHFFFAOYSA-N 6-(4,5-dihydro-1,3-oxazol-2-yl)-3-ethyl-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1C1=NCCO1 GVSFJJXEFOKQEW-UHFFFAOYSA-N 0.000 claims 1
- PHYRLJHGBFFWBA-UHFFFAOYSA-N 6-(furan-2-yl)-3,5-dimethyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound S1C=2NC(=O)N(C)C(=O)C=2C(C)=C1C1=CC=CO1 PHYRLJHGBFFWBA-UHFFFAOYSA-N 0.000 claims 1
- AWAIRQYZSUKKFE-UHFFFAOYSA-N 6-(furan-2-yl)-5-methyl-3-(2-methylpropyl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)NC=2SC=1C1=CC=CO1 AWAIRQYZSUKKFE-UHFFFAOYSA-N 0.000 claims 1
- APOXOOAUNRTWIW-UHFFFAOYSA-N 6-(furan-3-yl)-5-methyl-3-(2-methylpropyl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)NC=2SC=1C=1C=COC=1 APOXOOAUNRTWIW-UHFFFAOYSA-N 0.000 claims 1
- FMGXGQAJAYPVAB-NSHDSACASA-N 6-[(4s)-4-ethyl-4,5-dihydro-1,3-oxazol-2-yl]-1,5-dimethyl-3-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC[C@H]1COC(C2=C(C=3C(=O)N(CC(C)C)C(=O)N(C)C=3S2)C)=N1 FMGXGQAJAYPVAB-NSHDSACASA-N 0.000 claims 1
- JQJTULYLWIREKP-JTQLQIEISA-N 6-[(4s)-4-ethyl-4,5-dihydro-1,3-oxazol-2-yl]-5-methyl-3-(2-methylpropyl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC[C@H]1COC(C2=C(C=3C(=O)N(CC(C)C)C(=O)NC=3S2)C)=N1 JQJTULYLWIREKP-JTQLQIEISA-N 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000029197 Amphetamine-Related disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 208000009132 Catalepsy Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000016285 Movement disease Diseases 0.000 claims 1
- FSTUTPDEYUBTEL-UHFFFAOYSA-N N,3,5-trimethyl-2,4-dioxo-1H-thieno[2,3-d]pyrimidine-6-carboxamide Chemical compound N1C(=O)N(C)C(=O)C2=C1SC(C(=O)NC)=C2C FSTUTPDEYUBTEL-UHFFFAOYSA-N 0.000 claims 1
- RFVOIJHSHNFZIY-UHFFFAOYSA-N N,5-dimethyl-4-oxo-3-(2-oxopropyl)-1,2-dihydrothieno[2,3-d]pyrimidine-6-carboxamide Chemical compound CNC(=O)C1=C(C2=C(NCN(C2=O)CC(C)=O)S1)C RFVOIJHSHNFZIY-UHFFFAOYSA-N 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000026251 Opioid-Related disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- 206010047853 Waxy flexibility Diseases 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 229930003827 cannabinoid Natural products 0.000 claims 1
- 239000003557 cannabinoid Substances 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 201000006145 cocaine dependence Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- HSHDZEONKFFGNS-UHFFFAOYSA-N ethyl 3,5-dimethyl-2,4-dioxo-1h-thieno[2,3-d]pyrimidine-6-carboxylate Chemical compound N1C(=O)N(C)C(=O)C2=C1SC(C(=O)OCC)=C2C HSHDZEONKFFGNS-UHFFFAOYSA-N 0.000 claims 1
- LZYZNQYQLYGALK-UHFFFAOYSA-N ethyl 5-methyl-2,4-dioxo-3-prop-2-ynyl-1h-thieno[2,3-d]pyrimidine-6-carboxylate Chemical compound N1C(=O)N(CC#C)C(=O)C2=C1SC(C(=O)OCC)=C2C LZYZNQYQLYGALK-UHFFFAOYSA-N 0.000 claims 1
- 230000003492 excitotoxic effect Effects 0.000 claims 1
- 231100000063 excitotoxicity Toxicity 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000005040 opiate dependence Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000005156 substituted alkylene group Chemical group 0.000 claims 1
- 230000024883 vasodilation Effects 0.000 claims 1
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| US81574506P | 2006-06-21 | 2006-06-21 | |
| PCT/US2007/063143 WO2007103776A2 (en) | 2006-03-02 | 2007-03-02 | A2a adenosine receptor antagonists |
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| JP2009528389A JP2009528389A (ja) | 2009-08-06 |
| JP2009528389A5 true JP2009528389A5 (https=) | 2011-04-07 |
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| JP (1) | JP2009528389A (https=) |
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| GB0718432D0 (en) * | 2007-09-21 | 2007-10-31 | Vernalis R&D Ltd | New chemical compounds |
| GB0718434D0 (en) * | 2007-09-21 | 2007-10-31 | Vernalis R&D Ltd | New chemical compounds |
| TWI473614B (zh) | 2008-05-29 | 2015-02-21 | Kyowa Hakko Kirin Co Ltd | Anti-analgesic inhibitors |
| US20100093723A1 (en) * | 2008-10-13 | 2010-04-15 | Barbay J Kent | HETEROCYCLYL AND CYCLOALKYL SUBSTITUTED THIENO[2,3 d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| US20100093721A1 (en) * | 2008-10-13 | 2010-04-15 | Barbay J Kent | PHENYL AND HETEROARYL SUBSTITUTED THIENO[2,3-d]PYRIMIDINES AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| US20100093722A1 (en) * | 2008-10-13 | 2010-04-15 | Barbay J Kent | HETEROARYL AND PHENYL SUBSTITUTED THIENO[2,3-d]PYRIMIDINES AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| WO2011061754A1 (en) * | 2009-11-18 | 2011-05-26 | Council Of Scientific & Industrial Research | A novel 3-substituted 7-imino-2-thioxo-3, 7-dihydro-2h-thiazolo [4,5-di pyrimidin-6-yl - and process for preparation thereof |
| LT2776038T (lt) * | 2011-11-11 | 2018-04-25 | Gilead Apollo, Llc | Acc inhibitoriai ir jų panaudojimas |
| EA201591959A1 (ru) * | 2013-05-10 | 2016-03-31 | Нимбус Аполло, Инк. | Ингибиторы акк и их применение |
| CA2911818A1 (en) | 2013-05-10 | 2014-11-13 | Nimbus Apollo, Inc. | Acc inhibitors and uses thereof |
| AU2014262547A1 (en) | 2013-05-10 | 2015-11-26 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| MX2015015422A (es) | 2013-05-10 | 2016-06-21 | Nimbus Apollo Inc | Inhibidores de acetil-coa carboxilasa (acc) y usos de los mismos. |
| CN105793267B (zh) * | 2013-10-07 | 2018-02-06 | 拜耳制药股份公司 | 环状噻吩并尿嘧啶甲酰胺类及其用途 |
| US20150301030A1 (en) | 2014-04-22 | 2015-10-22 | Q-State Biosciences, Inc. | Models for parkinson's disease studies |
| EP3180345B1 (en) * | 2014-08-11 | 2018-10-10 | Hydra Biosciences, Inc. | Thieno- and furo[2,3-d]pyrimidine-2,4[1h,3h]-dione derivatives as trpc5 modulators for the treatment of neuropsychiatric disorders |
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| UY36586A (es) | 2015-03-26 | 2016-10-31 | Bayer Pharma AG | Heterociclilmetiltienouracilos y uso de los mismos |
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| HUE053175T2 (hu) | 2015-11-25 | 2021-06-28 | Gilead Apollo Llc | ACC-gátló észterek és azok alkalmazása |
| CA3004796C (en) | 2015-11-25 | 2023-11-14 | Gilead Apollo, Llc | Pyrazole acc inhibitors and uses thereof |
| EP3380479B1 (en) | 2015-11-25 | 2022-12-07 | Gilead Apollo, LLC | Triazole acc inhibitors and uses thereof |
| BR112018009212B1 (pt) | 2015-11-25 | 2022-06-14 | Gilead Apollo, Llc | Método para controlar patógenos fúngicos agrícolas |
| CN119977993A (zh) | 2016-03-02 | 2025-05-13 | 吉利德阿波罗公司 | 噻吩并嘧啶二酮acc抑制剂的固体形式及其制备方法 |
| WO2018041771A1 (de) | 2016-09-02 | 2018-03-08 | Bayer Pharma Aktiengesellschaft | (1-methylcyclopropyl)methyl-substituierte thienouracile und ihre verwendung |
| WO2018054846A1 (de) | 2016-09-23 | 2018-03-29 | Bayer Aktiengesellschaft | N3-cyclisch substituierte thienouracile und ihre verwendung |
| CN108341830B (zh) | 2017-01-22 | 2021-03-02 | 广东东阳光药业有限公司 | 噻吩并嘧啶衍生物及其在药物中的应用 |
| PT3600309T (pt) | 2017-03-28 | 2022-10-03 | Gilead Sciences Inc | Combinações terapêuticas para o tratamento de doenças hepáticas |
| AU2018277241B2 (en) * | 2017-05-31 | 2021-03-04 | Novartis Ag | Crystalline forms of 5-bromo-2,6-di(1H-pyrazol-1- yl)pyrimidin-4-amine and new salts |
| WO2019020041A1 (zh) * | 2017-07-26 | 2019-01-31 | 南京圣和药业股份有限公司 | 作为acc抑制剂的化合物及其应用 |
| WO2020139803A1 (en) * | 2018-12-24 | 2020-07-02 | Dcb-Usa Llc | Benzothiadiazine derivatives and compositions comprising the same for treating disorders mediated by adenosine |
| EP3995498A4 (en) | 2019-07-02 | 2023-03-01 | Sunshine Lake Pharma Co., Ltd. | THIENOPYRIMIDI DERIVATIVES WITH STEREO CONFIGURATION AND THEIR USE IN MEDICINE |
| CN119173276A (zh) | 2022-04-13 | 2024-12-20 | 吉利德科学公司 | 用于治疗表达Trop-2的癌症的组合疗法 |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
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| US5023252A (en) * | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4992445A (en) * | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
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| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| SE9702001D0 (sv) * | 1997-05-28 | 1997-05-28 | Astra Pharma Prod | Novel compounds |
| ATE253580T1 (de) * | 1998-08-28 | 2003-11-15 | Astrazeneca Ab | Neue thieno(2,3-d)pyrimidindione, verfahren für ihre herstellung und ihre verwendung in der therapie |
| MXPA02004795A (es) * | 1999-11-12 | 2005-07-01 | Biogen Inc | Antagonistas del receptor de adenosina y los metodos para producir y utilizar los mismos. |
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| GB0100620D0 (en) * | 2001-01-10 | 2001-02-21 | Vernalis Res Ltd | Chemical cokpounds V |
| CA2433778A1 (en) * | 2001-02-14 | 2002-08-22 | William Glen Harter | Thieno'2,3-d pyrimidindione derivatives as matrix metalloproteinase inhibitors |
| EP1465634B1 (en) * | 2001-12-12 | 2014-10-22 | The Government of the United States of America, as represented by the Secretary Department of Health and Human Services | Methods for using adenosine receptor inhibitors to enhance immune response and inflammation |
| ES2208063B1 (es) * | 2002-04-01 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de la 4-(pirrolopirimidin-6-il)bencenosulfonamida. |
| BR0312943A (pt) * | 2002-07-17 | 2005-07-12 | Warner Lambert Co | Combinação de um inibidor alostérico de matriz metaloproteinase-13 com um inibidor seletivo de ciclooxigenase-2 que não é celecoxib ou valdecoxib |
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| DE60322748D1 (de) * | 2003-05-06 | 2008-09-18 | Cv Therapeutics Inc | Xanthinderivate als a2b-adenosinrezeptorantagonisten |
| PL1628662T3 (pl) * | 2003-05-21 | 2007-07-31 | Hoffmann La Roche | Pochodne benzotiazolu i ich zastosowanie w leczeniu chorób związanych z receptorem adenozynowym A2A |
| CA2544193C (en) * | 2003-10-31 | 2012-03-27 | Cv Therapeutics, Inc. | A2b adenosine receptor antagonists |
| US7523193B2 (en) * | 2004-05-18 | 2009-04-21 | International Business Machines Corporation | Method and apparatus for DNS pre-fetching for multiple clients |
| EP2121705A2 (en) * | 2006-12-01 | 2009-11-25 | Cv Therapeutics, Inc. | A2a adenosine receptor antagonists |
-
2007
- 2007-03-02 CA CA002644996A patent/CA2644996A1/en not_active Abandoned
- 2007-03-02 US US11/681,378 patent/US20070208040A1/en not_active Abandoned
- 2007-03-02 EP EP07757782A patent/EP1989210A2/en not_active Ceased
- 2007-03-02 JP JP2008557512A patent/JP2009528389A/ja active Pending
- 2007-03-02 WO PCT/US2007/063143 patent/WO2007103776A2/en not_active Ceased
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