JP2010511628A5 - - Google Patents
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- Publication number
- JP2010511628A5 JP2010511628A5 JP2009539494A JP2009539494A JP2010511628A5 JP 2010511628 A5 JP2010511628 A5 JP 2010511628A5 JP 2009539494 A JP2009539494 A JP 2009539494A JP 2009539494 A JP2009539494 A JP 2009539494A JP 2010511628 A5 JP2010511628 A5 JP 2010511628A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- dihydrothiopheno
- pyrimidine
- dione
- methyl
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229940002612 prodrug Drugs 0.000 claims description 8
- 239000000651 prodrug Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- JPDDMSDKBBPCEK-CSKARUKUSA-N 6-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-3-ethyl-1,5-dimethylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(C)C=2SC=1\C=C\C1=CC=C(OC)C(OC)=C1 JPDDMSDKBBPCEK-CSKARUKUSA-N 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 2
- VWRJRTRNYFJZAS-VAWYXSNFSA-N 1,3-diethyl-5-methyl-6-[(e)-2-phenylethenyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(CC)C=2SC=1\C=C\C1=CC=CC=C1 VWRJRTRNYFJZAS-VAWYXSNFSA-N 0.000 claims description 2
- WFAMKSGWIMBDLH-ZHACJKMWSA-N 1,5-dimethyl-6-[(e)-2-phenylethenyl]-3-prop-2-ynylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound S1C=2N(C)C(=O)N(CC#C)C(=O)C=2C(C)=C1\C=C\C1=CC=CC=C1 WFAMKSGWIMBDLH-ZHACJKMWSA-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
- ZWQZMOOECQNJRH-ZHACJKMWSA-N 3-ethyl-1,5-dimethyl-6-[(e)-2-phenylethenyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(C)C=2SC=1\C=C\C1=CC=CC=C1 ZWQZMOOECQNJRH-ZHACJKMWSA-N 0.000 claims description 2
- VVTDOAWVBUHYMP-MDZDMXLPSA-N 3-ethyl-1-(2-hydroxyethyl)-5-methyl-6-[(e)-2-phenylethenyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(CCO)C=2SC=1\C=C\C1=CC=CC=C1 VVTDOAWVBUHYMP-MDZDMXLPSA-N 0.000 claims description 2
- PGKMFTICSBOZHW-ZHACJKMWSA-N 3-ethyl-1-(3-hydroxypropyl)-5-methyl-6-[(e)-2-phenylethenyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(CCCO)C=2SC=1\C=C\C1=CC=CC=C1 PGKMFTICSBOZHW-ZHACJKMWSA-N 0.000 claims description 2
- JRJYNEYIILYZEI-MDZDMXLPSA-N 3-ethyl-5-methyl-6-[(e)-2-(4-methylphenyl)ethenyl]-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=C(C)C=C1 JRJYNEYIILYZEI-MDZDMXLPSA-N 0.000 claims description 2
- QGLVDTJLFFMKDQ-SDNWHVSQSA-N 3-ethyl-5-methyl-6-[(e)-2-(4-phenylphenyl)ethenyl]-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C(C=C1)=CC=C1C1=CC=CC=C1 QGLVDTJLFFMKDQ-SDNWHVSQSA-N 0.000 claims description 2
- VPTDBYKUWMMYES-RMKNXTFCSA-N 3-ethyl-5-methyl-6-[(e)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=C(C(F)(F)F)C=C1 VPTDBYKUWMMYES-RMKNXTFCSA-N 0.000 claims description 2
- LHSOGOXUANFNEJ-VOTSOKGWSA-N 3-ethyl-5-methyl-6-[(e)-2-pyridin-3-ylethenyl]-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=CN=C1 LHSOGOXUANFNEJ-VOTSOKGWSA-N 0.000 claims description 2
- BLSAUMXBWNUVHN-CMDGGOBGSA-N 3-ethyl-6-[(e)-2-(2-fluorophenyl)ethenyl]-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=CC=C1F BLSAUMXBWNUVHN-CMDGGOBGSA-N 0.000 claims description 2
- UIOYXSFRGJIAAB-MDZDMXLPSA-N 3-ethyl-6-[(e)-2-(2-methoxyphenyl)ethenyl]-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=CC=C1OC UIOYXSFRGJIAAB-MDZDMXLPSA-N 0.000 claims description 2
- DNAWLGURDUWARK-BQYQJAHWSA-N 3-ethyl-6-[(e)-2-(3-fluorophenyl)ethenyl]-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=CC(F)=C1 DNAWLGURDUWARK-BQYQJAHWSA-N 0.000 claims description 2
- XDAYENCKGPZWCY-CMDGGOBGSA-N 3-ethyl-6-[(e)-2-(3-methoxyphenyl)ethenyl]-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=CC(OC)=C1 XDAYENCKGPZWCY-CMDGGOBGSA-N 0.000 claims description 2
- BMLNLXDZFDTYAY-RMKNXTFCSA-N 3-ethyl-6-[(e)-2-(4-fluorophenyl)ethenyl]-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=C(F)C=C1 BMLNLXDZFDTYAY-RMKNXTFCSA-N 0.000 claims description 2
- ZRJQUNQLJKVWET-JXMROGBWSA-N 3-ethyl-6-[(e)-2-(4-methoxyphenyl)ethenyl]-5-methyl-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)NC=2SC=1\C=C\C1=CC=C(OC)C=C1 ZRJQUNQLJKVWET-JXMROGBWSA-N 0.000 claims description 2
- GZVSGFUGESSPEP-MDZDMXLPSA-N 5-methyl-3-(2-methylpropyl)-6-[(e)-2-phenylethenyl]-1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC(C)C)C(=O)NC=2SC=1\C=C\C1=CC=CC=C1 GZVSGFUGESSPEP-MDZDMXLPSA-N 0.000 claims description 2
- ZYRNLFPSWWUWDQ-WYMLVPIESA-N 6-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-3-ethyl-5-methyl-1-(phenylmethoxymethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2SC(\C=C\C=3C=C(OC)C(OC)=CC=3)=C(C)C=2C(=O)N(CC)C(=O)N1COCC1=CC=CC=C1 ZYRNLFPSWWUWDQ-WYMLVPIESA-N 0.000 claims description 2
- OFJVDOIYGSHIBE-VQHVLOKHSA-N 6-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-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=1\C=C\C1=CC=C(OC)C(OC)=C1 OFJVDOIYGSHIBE-VQHVLOKHSA-N 0.000 claims description 2
- BDWPDJBPUQVUCM-RMKNXTFCSA-N 6-[(e)-2-(4-chlorophenyl)ethenyl]-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=1\C=C\C1=CC=C(Cl)C=C1 BDWPDJBPUQVUCM-RMKNXTFCSA-N 0.000 claims description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 2
- 201000006474 Brain Ischemia Diseases 0.000 claims description 2
- 208000009132 Catalepsy Diseases 0.000 claims description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 208000016285 Movement disease Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010047853 Waxy flexibility Diseases 0.000 claims description 2
- 229940121359 adenosine receptor antagonist Drugs 0.000 claims description 2
- 229940025084 amphetamine Drugs 0.000 claims description 2
- 229930003827 cannabinoid Natural products 0.000 claims description 2
- 239000003557 cannabinoid Substances 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 229960003920 cocaine Drugs 0.000 claims description 2
- 230000001149 cognitive effect Effects 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- 230000003492 excitotoxic effect Effects 0.000 claims description 2
- 231100000063 excitotoxicity Toxicity 0.000 claims description 2
- 230000028993 immune response Effects 0.000 claims description 2
- 229960002715 nicotine Drugs 0.000 claims description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 5
- -1 3,5-dimethoxyphenyl Chemical group 0.000 claims 1
- VVTDOAWVBUHYMP-KTKRTIGZSA-N 3-ethyl-1-(2-hydroxyethyl)-5-methyl-6-[(z)-2-phenylethenyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC=1C=2C(=O)N(CC)C(=O)N(CCO)C=2SC=1\C=C/C1=CC=CC=C1 VVTDOAWVBUHYMP-KTKRTIGZSA-N 0.000 claims 1
- 206010019668 Hepatic fibrosis Diseases 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 0 *C(*)=C(*)c1c(*)c(C(N(*)C(N2*)=O)=O)c2[s]1 Chemical compound *C(*)=C(*)c1c(*)c(C(N(*)C(N2*)=O)=O)c2[s]1 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- IYNDDQQFQKDYFH-VOTSOKGWSA-N 6-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]-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=1\C=C\C1=CC(OC)=CC(OC)=C1 IYNDDQQFQKDYFH-VOTSOKGWSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87225406P | 2006-12-01 | 2006-12-01 | |
| PCT/US2007/085978 WO2008070529A2 (en) | 2006-12-01 | 2007-11-29 | A2a adenosine receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010511628A JP2010511628A (ja) | 2010-04-15 |
| JP2010511628A5 true JP2010511628A5 (OSRAM) | 2012-01-05 |
Family
ID=39298223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009539494A Pending JP2010511628A (ja) | 2006-12-01 | 2007-11-29 | Ａ２ａアデノシン受容体アンタゴニスト |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7776868B2 (OSRAM) |
| EP (1) | EP2121705A2 (OSRAM) |
| JP (1) | JP2010511628A (OSRAM) |
| CA (1) | CA2670788A1 (OSRAM) |
| WO (1) | WO2008070529A2 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070208040A1 (en) * | 2006-03-02 | 2007-09-06 | Elfatih Elzein | A2a adenosine receptor antagonists |
| TWI473614B (zh) | 2008-05-29 | 2015-02-21 | Kyowa Hakko Kirin Co Ltd | Anti-analgesic inhibitors |
| WO2011101861A1 (en) | 2010-01-29 | 2011-08-25 | Msn Laboratories Limited | Process for preparation of dpp-iv inhibitors |
| 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 |
| 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 |
| UY36586A (es) | 2015-03-26 | 2016-10-31 | Bayer Pharma AG | Heterociclilmetiltienouracilos y uso de los mismos |
| WO2018041771A1 (de) | 2016-09-02 | 2018-03-08 | Bayer Pharma Aktiengesellschaft | (1-methylcyclopropyl)methyl-substituierte thienouracile und ihre verwendung |
| KR20190053242A (ko) | 2016-09-23 | 2019-05-17 | 바이엘 악티엔게젤샤프트 | N3-시클릭 치환된 티에노우라실 및 그의 용도 |
| KR101709307B1 (ko) * | 2016-10-31 | 2017-02-23 | 퓨쳐메디신 주식회사 | 아데노신 유도체를 포함하는 비알콜성 지방간염, 간섬유증 및 간경변증 예방 및 치료용 약학적 조성물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US4326525A (en) | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US5364620A (en) | 1983-12-22 | 1994-11-15 | Elan Corporation, Plc | Controlled absorption diltiazem formulation for once daily administration |
| US4902514A (en) | 1988-07-21 | 1990-02-20 | Alza Corporation | Dosage form for administering nilvadipine for treating cardiovascular symptoms |
| CA2094270C (en) * | 1990-10-18 | 1997-01-21 | Fumio Suzuki | Xanthine derivatives |
| SE9702001D0 (sv) * | 1997-05-28 | 1997-05-28 | Astra Pharma Prod | Novel compounds |
| WO2002064598A1 (en) * | 2001-02-14 | 2002-08-22 | Warner-Lambert Company Llc | Thieno'2,3-d pyrimidindione derivatives as matrix metalloproteinase inhibitors |
| US20070208040A1 (en) * | 2006-03-02 | 2007-09-06 | Elfatih Elzein | A2a adenosine receptor antagonists |
-
2007
- 2007-11-29 WO PCT/US2007/085978 patent/WO2008070529A2/en not_active Ceased
- 2007-11-29 US US11/947,690 patent/US7776868B2/en active Active
- 2007-11-29 JP JP2009539494A patent/JP2010511628A/ja active Pending
- 2007-11-29 CA CA002670788A patent/CA2670788A1/en not_active Abandoned
- 2007-11-29 EP EP07864929A patent/EP2121705A2/en not_active Withdrawn
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