CA2644996A1

CA2644996A1 - A2a adenosine receptor antagonists

A2a adenosine receptor antagonists Download PDF

Info

Publication number: CA2644996A1
Authority: CA; Canada
Prior art keywords: dihydrothiopheno; pyrimidine; methyl; dione; ethyl
Prior art date: 2006-03-02
Legal status : Abandoned

Application number

CA002644996A

Other languages

English (en)

French (fr)

Inventor

Elfatih Elzein

Rao Kalla

Jeff Zablocki

Xiaofen Li

Thao Perry

Tetsuya Kobayashi

Eric Parkhill

Current Assignee

Gilead Palo Alto Inc

Original Assignee

Individual

Priority date

2006-03-02

Filing date

2007-03-02

Publication date

2007-09-13

2007-03-02 Application filed by Individual filed Critical Individual

2007-09-13 Publication of CA2644996A1 publication Critical patent/CA2644996A1/en

Status Abandoned legal-status Critical Current

Links

101150051188 Adora2a gene Proteins 0.000 title abstract description 15
229940121359 adenosine receptor antagonist Drugs 0.000 title abstract description 6
239000000296 purinergic P1 receptor antagonist Substances 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 304
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 75
238000000034 method Methods 0.000 claims abstract description 56
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
201000010099 disease Diseases 0.000 claims abstract description 16
241000124008 Mammalia Species 0.000 claims abstract description 12
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims abstract description 11
229960002715 nicotine Drugs 0.000 claims abstract description 11
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims abstract description 11
208000018737 Parkinson disease Diseases 0.000 claims abstract description 10
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims abstract description 10
206010013663 drug dependence Diseases 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
208000011117 substance-related disease Diseases 0.000 claims abstract description 8
206010008118 cerebral infarction Diseases 0.000 claims abstract description 6
230000003492 excitotoxic effect Effects 0.000 claims abstract description 6
231100000063 excitotoxicity Toxicity 0.000 claims abstract description 6
201000006474 Brain Ischemia Diseases 0.000 claims abstract description 5
206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 5
208000023105 Huntington disease Diseases 0.000 claims abstract description 5
208000008589 Obesity Diseases 0.000 claims abstract description 5
208000015114 central nervous system disease Diseases 0.000 claims abstract description 5
229960003920 cocaine Drugs 0.000 claims abstract description 5
230000001149 cognitive effect Effects 0.000 claims abstract description 5
208000035475 disorder Diseases 0.000 claims abstract description 5
235000020824 obesity Nutrition 0.000 claims abstract description 5
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 4
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 4
208000016285 Movement disease Diseases 0.000 claims abstract description 4
229930003827 cannabinoid Natural products 0.000 claims abstract description 4
239000003557 cannabinoid Substances 0.000 claims abstract description 4
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims abstract description 3
229940025084 amphetamine Drugs 0.000 claims abstract description 3
-1 3-ethyl-5-methyl-2,4-dioxo(1,3-dihydrothiopheno[2,3-d]pyrimidin-6-yl) Chemical group 0.000 claims description 86
125000000217 alkyl group Chemical group 0.000 claims description 68
229910052739 hydrogen Inorganic materials 0.000 claims description 52
125000001072 heteroaryl group Chemical group 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 48
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 46
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
229910052757 nitrogen Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
239000011593 sulfur Chemical group 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
208000009132 Catalepsy Diseases 0.000 claims description 8
206010047853 Waxy flexibility Diseases 0.000 claims description 8
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
150000003857 carboxamides Chemical class 0.000 claims description 7
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 description 6
150000002148 esters Chemical class 0.000 claims description 6
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 description 5
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 description 5
239000000651 prodrug Substances 0.000 claims description 5
229940002612 prodrug Drugs 0.000 claims description 5
230000024883 vasodilation Effects 0.000 claims description 5
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 description 4
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 description 4
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 description 4
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 description 4
NHPPQAUFHRWCMA-UHFFFAOYSA-N 3-ethyl-1-methyl-5-(5-methylfuran-2-yl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(CC)C(=O)N(C)C=2SC=C1C1=CC=C(C)O1 NHPPQAUFHRWCMA-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
XRFUNIUUDSLWKR-UHFFFAOYSA-N 6-(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=1C=2C(=O)N(CC(C)C)C(=O)NC=2SC=1C1=NCCO1 XRFUNIUUDSLWKR-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
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 description 4
229940127600 A2A receptor antagonist Drugs 0.000 claims description 4
FUBLBZQRGREYQE-UHFFFAOYSA-N ethyl 1,5-dimethyl-2,4-dioxo-3-prop-2-ynylthieno[2,3-d]pyrimidine-6-carboxylate Chemical compound CN1C(=O)N(CC#C)C(=O)C2=C1SC(C(=O)OCC)=C2C FUBLBZQRGREYQE-UHFFFAOYSA-N 0.000 claims description 4
125000005156 substituted alkylene group Chemical group 0.000 claims description 4
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
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 description 3
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 description 3
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 description 3
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 description 3
GRUUGEBVNLSZEI-UHFFFAOYSA-N 3-ethyl-5-(5-methylfuran-2-yl)-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(CC)C(=O)NC=2SC=C1C1=CC=C(C)O1 GRUUGEBVNLSZEI-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 2
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