JP2015526411A5 - - Google Patents
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- Publication number
- JP2015526411A5 JP2015526411A5 JP2015521942A JP2015521942A JP2015526411A5 JP 2015526411 A5 JP2015526411 A5 JP 2015526411A5 JP 2015521942 A JP2015521942 A JP 2015521942A JP 2015521942 A JP2015521942 A JP 2015521942A JP 2015526411 A5 JP2015526411 A5 JP 2015526411A5
- Authority
- JP
- Japan
- Prior art keywords
- alkoxy
- aliphatic
- alkyl
- aryl
- heteroaryl
- 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.)
- Granted
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- 125000003545 alkoxy group Chemical group 0.000 claims description 440
- 125000001931 aliphatic group Chemical group 0.000 claims description 279
- 125000000217 alkyl group Chemical group 0.000 claims description 273
- 125000000623 heterocyclic group Chemical group 0.000 claims description 180
- 125000003118 aryl group Chemical group 0.000 claims description 173
- 125000001072 heteroaryl group Chemical group 0.000 claims description 166
- -1 hydroxy, amino Chemical group 0.000 claims description 112
- 229910052731 fluorine Inorganic materials 0.000 claims description 94
- 229910052740 iodine Inorganic materials 0.000 claims description 89
- 229910052801 chlorine Inorganic materials 0.000 claims description 84
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 229910052794 bromium Inorganic materials 0.000 claims description 66
- 229910052717 sulfur Inorganic materials 0.000 claims description 66
- 229910052760 oxygen Inorganic materials 0.000 claims description 65
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 64
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 61
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 48
- 125000004104 aryloxy group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 36
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 34
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
- 206010016654 Fibrosis Diseases 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 230000004761 fibrosis Effects 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 10
- 210000000056 organ Anatomy 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 210000001519 tissue Anatomy 0.000 claims description 9
- 206010060932 Postoperative adhesion Diseases 0.000 claims description 8
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 8
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 7
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 7
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 7
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 4
- 206010048654 Muscle fibrosis Diseases 0.000 claims description 4
- 206010028594 Myocardial fibrosis Diseases 0.000 claims description 4
- 201000004404 Neurofibroma Diseases 0.000 claims description 4
- 206010034665 Peritoneal fibrosis Diseases 0.000 claims description 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
- 206010039710 Scleroderma Diseases 0.000 claims description 4
- 206010050207 Skin fibrosis Diseases 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 4
- 230000035876 healing Effects 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 231100000241 scar Toxicity 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000002207 metabolite Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims 4
- 238000007069 methylation reaction Methods 0.000 claims 4
- 230000005494 condensation Effects 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 230000003510 anti-fibrotic effect Effects 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 230000003176 fibrotic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 0 B**N(*=*CC)C(C(C)C=*)=* Chemical compound B**N(*=*CC)C(C(C)C=*)=* 0.000 description 101
- 125000004438 haloalkoxy group Chemical class 0.000 description 10
- 241000239366 Euphausiacea Species 0.000 description 5
- 125000003418 alkyl amino alkoxy group Chemical class 0.000 description 5
- 125000005241 heteroarylamino group Chemical group 0.000 description 5
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- 238000000034 method Methods 0.000 description 4
- 206010061692 Benign muscle neoplasm Diseases 0.000 description 3
- 201000004458 Myoma Diseases 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 description 3
- 229960003073 pirfenidone Drugs 0.000 description 3
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Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2635581C (en) | 2005-12-28 | 2017-02-28 | Vertex Pharmaceuticals Incorporated | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| US9902712B2 (en) | 2013-12-19 | 2018-02-27 | Sunshine Lake Pharma Co., Ltd. | Nitrogenous heterocyclic derivatives and their application in drugs |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
| RU2749213C2 (ru) | 2014-10-07 | 2021-06-07 | Вертекс Фармасьютикалз Инкорпорейтед | Сокристаллы модуляторов регулятора трансмембранной проводимости при кистозном фиброзе |
| CN106397408B (zh) * | 2015-07-30 | 2019-04-02 | 四川大学 | 5-甲基-2(1h)吡啶酮衍生物及其制备方法和用途 |
| FR3046793B1 (fr) * | 2016-01-14 | 2018-01-05 | Les Laboratoires Servier | Nouveaux derives de phosphinanes et azaphosphinanes, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN106083817B (zh) * | 2016-06-14 | 2019-01-18 | 四川大学 | 吡非尼酮衍生物及其制备方法 |
| CN106045971B (zh) * | 2016-06-16 | 2018-12-21 | 杨若一 | 吡非尼酮衍生物及其制备方法 |
| CN107663177B (zh) * | 2016-07-27 | 2022-07-08 | 广东东阳光药业有限公司 | 2,6-二甲基嘧啶酮衍生物的盐及其用途 |
| WO2018019244A1 (zh) * | 2016-07-27 | 2018-02-01 | 广东东阳光药业有限公司 | 2,6-二甲基嘧啶酮衍生物的盐及其用途 |
| EP3652158B1 (en) * | 2017-07-14 | 2024-05-29 | Sunshine Lake Pharma Co., Ltd. | Method for preparing pyrimidone compound |
| CN112770757B (zh) * | 2018-10-19 | 2024-01-16 | 广东东阳光药业股份有限公司 | 一种治疗纤维化疾病的药物组合或药物组合物 |
| US20230065740A1 (en) | 2018-12-28 | 2023-03-02 | Spv Therapeutics Inc. | Cyclin-dependent kinase inhibitors |
| MX2021008661A (es) | 2019-01-18 | 2021-08-19 | Astrazeneca Ab | Inhibidores de la pcsk9 y metodos de uso de los mismos. |
| CN109734618B (zh) * | 2019-02-27 | 2021-08-17 | 宜春学院 | 一种苯氧乙酰胺类化合物的制备方法和苯氧乙酰胺类化合物 |
| CN109942497A (zh) * | 2019-05-06 | 2019-06-28 | 南京工业大学 | 一种多取代嘧啶酮化合物及其制备方法 |
| WO2021198191A1 (en) | 2020-03-30 | 2021-10-07 | Enyo Pharma | Quinazolinone derivatives and uses thereof for treating a cancer |
| IL307258A (en) | 2021-04-05 | 2023-11-01 | Halia Therapeutics Inc | NEK7 inhibitors |
| US20250177382A1 (en) | 2021-04-22 | 2025-06-05 | Halia Therapeutics, Inc. | Nek7 inhibitors |
| WO2023056935A1 (zh) | 2021-10-09 | 2023-04-13 | 广东东阳光药业有限公司 | 抗纤维化组合物 |
| KR102762725B1 (ko) * | 2022-03-24 | 2025-02-06 | 주식회사 케이에스비튜젠 | 레보드로프로피진을 유효성분으로 포함하는 근육질환의 예방, 치료 또는 개선용 조성물 |
Family Cites Families (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185689A (en) | 1965-05-25 | Tolyl-x-(jh)-pyrimidones | ||
| DE2808193A1 (de) | 1978-02-25 | 1979-09-06 | Basf Ag | Pyridazon-verbindungen |
| DE3202678A1 (de) | 1982-01-28 | 1983-08-04 | Basf Ag, 6700 Ludwigshafen | Substituierte 4,5-dimethoxy-pyridazone, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
| US5149810A (en) | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
| GB8818560D0 (en) | 1988-08-04 | 1988-09-07 | Ici Plc | Novel compounds |
| JPH02215719A (ja) | 1989-02-15 | 1990-08-28 | Yamauchi Akitomo | 線維化病変組織の修復並びに線維化病変の阻止剤 |
| GB8908638D0 (en) | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
| GB8915962D0 (en) | 1989-07-12 | 1989-08-31 | Ici Plc | Novel compounds |
| AU627906B2 (en) * | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| IE912114A1 (en) | 1990-07-02 | 1992-01-15 | Union Pharma Scient Appl | Novel pyrimidine derivatives which are angiotensin ii¹receptor antagonists, their methods of preparation and¹pharmaceutical compositions in which they are present |
| GB9022445D0 (en) | 1990-10-16 | 1990-11-28 | Ici Plc | Heterocyclic compounds |
| US5470975A (en) | 1990-10-16 | 1995-11-28 | E.R. Squibb & Sons, Inc. | Dihydropyrimidine derivatives |
| TW229142B (OSRAM) | 1992-04-15 | 1994-09-01 | Nissan Detrochem Corp | |
| CA2094949A1 (en) | 1992-04-28 | 1993-10-29 | Eiki Nagano | Pyrimidone derivatives and their use |
| EP0724573A1 (en) | 1993-10-20 | 1996-08-07 | PHARMACIA & UPJOHN COMPANY | Pyrimidinones as antiarthritic and anti-inflammatories |
| DE4343528A1 (de) | 1993-12-16 | 1995-06-22 | Schering Ag | Zweifach heterocyclisch substituierte Benzole und Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| DE4431218A1 (de) | 1994-09-02 | 1996-03-07 | Bayer Ag | Substituierte Pyrimidin(thi)one |
| DE4432888A1 (de) | 1994-09-15 | 1996-03-21 | Bayer Ag | Verwendung von Aryluracilen im semi- und nicht-selektiven Bereich der Unkrautbekämpfung |
| KR100300566B1 (ko) | 1994-09-17 | 2001-11-22 | 조생현 | 피리미디논유도체와그의제조방법및용도 |
| DE19520613A1 (de) | 1995-06-06 | 1996-12-12 | Bayer Ag | Phenylpyridazinone |
| US6369067B1 (en) | 1997-10-27 | 2002-04-09 | Dr. Reddy's Research Foundation | Monocyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them |
| CN1305466A (zh) | 1998-04-09 | 2001-07-25 | 拜尔公司 | 取代的苯基哒嗪酮类化合物 |
| NZ522773A (en) * | 2000-06-12 | 2005-06-24 | Eisai Co Ltd | 1,2-dihydropyridine compounds, manufacturing method thereof and use thereof |
| WO2002053156A1 (en) | 2000-12-29 | 2002-07-11 | Alteon, Inc. | Method for treating glaucoma ii b |
| JP2005510508A (ja) * | 2001-11-08 | 2005-04-21 | 藤沢薬品工業株式会社 | アデノシンアンタゴニストとしてのチアゾールピリダジノン類 |
| US7030141B2 (en) * | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| EP1470112A1 (en) | 2002-01-18 | 2004-10-27 | Pharmacia Corporation | Substituted pyridazinones as inhibitors of p38 |
| SI1490064T1 (sl) | 2002-02-14 | 2010-01-29 | Pharmacia Corp | Substituirani piridinoni kot modulatorji p38 MAP kinaze |
| TW200307667A (en) | 2002-05-06 | 2003-12-16 | Bristol Myers Squibb Co | Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors |
| CN1218942C (zh) | 2002-06-11 | 2005-09-14 | 中南大学湘雅医学院 | 抗纤维化吡啶酮化合物及其生产工艺方法 |
| US7183287B2 (en) * | 2003-04-03 | 2007-02-27 | Pharmacia Corporation | Substituted pyrimidinones |
| CA2529790A1 (en) * | 2003-06-27 | 2005-01-27 | Banyu Pharmaceutical Co., Ltd. | Heteroaryloxy nitrogenous saturated heterocyclic derivative |
| NL1026826C2 (nl) | 2003-08-13 | 2007-01-04 | Pharmacia Corp | Gesubstitueerde pyridinonen. |
| US7790736B2 (en) | 2003-08-13 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7790734B2 (en) | 2003-09-08 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| CA2545813C (en) | 2003-11-14 | 2011-01-04 | Shanghai Genomics, Inc. | The derivatives of pyridone and use thereof |
| CA2558272C (en) | 2004-03-05 | 2011-02-15 | Banyu Pharmaceutical Co., Ltd. | Pyridone derivative |
| CA2565437A1 (en) * | 2004-06-18 | 2006-01-05 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| CN1308028C (zh) | 2004-09-10 | 2007-04-04 | 石药集团中奇制药技术（石家庄）有限公司 | 一种治疗肝纤维化的药物及其制备方法 |
| US20070270446A1 (en) | 2004-10-06 | 2007-11-22 | Smithkline Beecham Corporation | Reversed Pyrimidinone Compounds as Calcilytics |
| MX2007004514A (es) * | 2004-10-13 | 2007-05-09 | Pharmacia & Upjohn Co Llc | Formas cristalinas de 3-[5-cloro-4-[(2,4-difluorobencil)oxi]-6 oxopirimidin-1(6h)-il]-n-(2-hidroxetil)-4-metilbenzamida. |
| JP4912314B2 (ja) * | 2004-10-26 | 2012-04-11 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 因子Ｘａ化合物 |
| CN1846699A (zh) * | 2005-04-13 | 2006-10-18 | 中南大学湘雅医院 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
| KR20080080136A (ko) | 2005-11-22 | 2008-09-02 | 스미스클라인 비참 코포레이션 | 칼실리틱 화합물 |
| US20070129379A1 (en) | 2005-12-01 | 2007-06-07 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| EA015942B1 (ru) | 2006-05-05 | 2011-12-30 | Милленниум Фамэсьютикэлс, Инк. | Замещенные имидазолы, композиция на их основе, способ профилактики или лечения нежелательного тромбообразования с их помощью и способ ингибирования коагуляции образцов крови |
| PE20080150A1 (es) | 2006-06-02 | 2008-04-11 | Janssen Pharmaceutica Nv | Derivados de piridinona n-aril y n-heteroaril sustituidos como antagonistas del receptor de la hormona concentradora de melanina (mch) |
| WO2007142217A1 (ja) | 2006-06-07 | 2007-12-13 | Banyu Pharmaceutical Co., Ltd. | １－フェニルピリドン誘導体 |
| EP2079724B1 (en) * | 2006-07-20 | 2010-05-26 | Amgen Inc. | Substituted pyridone compounds and methods of use |
| BRPI0716579A2 (pt) | 2006-08-25 | 2013-10-08 | Boehringer Ingelheim Int | Derivados de piridona com atividade antagonista ao mch e medicamentos que compreendem estes compostos |
| WO2008041090A1 (en) | 2006-10-06 | 2008-04-10 | Pfizer Limited | Malanin concentrating hormone receptor-1 antagonist pyridinones |
| ES2483866T3 (es) | 2006-12-05 | 2014-08-08 | Janssen Pharmaceutica Nv | Derivados de diaza-espiro-piridinona sustituidos novedosos para uso en enfermedades mediadas por MCH-1 |
| WO2008086226A2 (en) * | 2007-01-05 | 2008-07-17 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| US8198276B2 (en) | 2007-06-06 | 2012-06-12 | Xcovery Holding Company Llc | Kinase inhibitor compounds |
| WO2008156607A1 (en) | 2007-06-12 | 2008-12-24 | Neurogen Corporation | Substituted pyrimidinones |
| DE102007028320A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| BRPI0813244B8 (pt) | 2007-06-27 | 2021-05-25 | Astrazeneca Ab | compostos derivados de pirazinona, composições compreendendo ditos compostos, uso dos compostos no tratamento de doenças de pulmão e composto intermediário |
| EP2188288A1 (en) * | 2007-09-11 | 2010-05-26 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole n-oxides |
| US8329711B2 (en) | 2007-10-23 | 2012-12-11 | Msd K.K. | Pyridone-substituted-dihydropyrazolopyrimidinone derivative |
| GB0724342D0 (en) * | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
| US8153813B2 (en) * | 2007-12-20 | 2012-04-10 | Abbott Laboratories | Benzothiazole and benzooxazole derivatives and methods of use |
| JP5276676B2 (ja) * | 2008-02-21 | 2013-08-28 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｅｒｋ阻害剤である化合物 |
| CN101235013A (zh) * | 2008-03-10 | 2008-08-06 | 广东东阳光药业有限公司 | 结晶型1-（3-氟苯基）-5-甲基-2-（1h）吡啶酮、其制备方法、及其组合物和应用 |
| JP5627574B2 (ja) | 2008-06-03 | 2014-11-19 | インターミューン， インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
| US20100190731A1 (en) * | 2009-01-26 | 2010-07-29 | Jeff Olgin | Methods for treating acute myocardial infarctions and associated disorders |
| US9006454B2 (en) | 2009-04-02 | 2015-04-14 | Merck Serono S.A. | Dihydroorotate dehydrogenase inhibitors |
| JP5722883B2 (ja) | 2009-05-25 | 2015-05-27 | 中南大学Ｃｅｎｔｒａｌ Ｓｏｕｔｈ Ｕｎｉｖｅｒｓｉｔｙ | １−（置換ベンジル）−５−トリフルオロメチル−２−（１ｈ）ピリドン化合物及びその塩、並びにその製造方法及びその用途 |
| JP5583758B2 (ja) | 2009-05-25 | 2014-09-03 | 中南大学 | １−（置換アリール）−５−トリフルオロメチル−２−（１ｈ）ピリドン化合物及びその塩、並びにその製造方法及びその用途 |
| CN101921225B (zh) | 2009-06-11 | 2013-04-03 | 北京凯得尔森生物技术有限公司 | 吡啡尼酮类化合物、其制备方法和应用 |
| PL2542084T3 (pl) | 2010-03-04 | 2018-05-30 | Merck Sharp & Dohme Corp. | Inhibitory katecholo-O-metylotransferazy i ich zastosowanie w leczeniu zaburzeń psychotycznych |
| WO2012011592A1 (ja) | 2010-07-23 | 2012-01-26 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| JP2014515345A (ja) * | 2011-01-10 | 2014-06-30 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | 脂肪酸シンターゼ阻害剤としてのピリミジノン誘導体 |
| US9056110B2 (en) | 2011-12-06 | 2015-06-16 | Confluence Life Sciences, Inc. | Substituted pyrimidinone-phenyl-pyrimidinyl compounds |
| US8859559B2 (en) * | 2011-12-20 | 2014-10-14 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
-
2013
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- 2013-07-18 JP JP2015521942A patent/JP6186434B2/ja active Active
- 2013-07-18 WO PCT/CN2013/000860 patent/WO2014012360A1/en not_active Ceased
- 2013-07-18 EP EP13819193.7A patent/EP2875001B1/en active Active
- 2013-07-18 AU AU2013292950A patent/AU2013292950C1/en active Active
- 2013-07-18 KR KR1020157002193A patent/KR102057877B1/ko active Active
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