ZA200506611B - Thienopyrimidine compounds and use thereof - Google Patents
Thienopyrimidine compounds and use thereof Download PDFInfo
- Publication number
- ZA200506611B ZA200506611B ZA200506611A ZA200506611A ZA200506611B ZA 200506611 B ZA200506611 B ZA 200506611B ZA 200506611 A ZA200506611 A ZA 200506611A ZA 200506611 A ZA200506611 A ZA 200506611A ZA 200506611 B ZA200506611 B ZA 200506611B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- group
- compound
- alkoxy
- methyl
- Prior art date
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- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 129
- -1 (2- methoxyethyl)(methyl)amino Chemical group 0.000 claims description 110
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 claims description 23
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 claims description 22
- 229940035638 gonadotropin-releasing hormone Drugs 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
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- 238000000034 method Methods 0.000 claims description 18
- 230000003042 antagnostic effect Effects 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
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- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- ZDNJMFVISJXAJC-UHFFFAOYSA-N 1-[4-[1-[(2,6-difluorophenyl)methyl]-3-[4-(2-hydroxypropan-2-yl)phenyl]-5-[[2-methoxyethyl(methyl)amino]methyl]-2,4-dioxothieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea Chemical compound O=C1N(C=2C=CC(=CC=2)C(C)(C)O)C(=O)C=2C(CN(C)CCOC)=C(C=3C=CC(NC(=O)NOC)=CC=3)SC=2N1CC1=C(F)C=CC=C1F ZDNJMFVISJXAJC-UHFFFAOYSA-N 0.000 claims 1
- MYVNZIYUALDHCS-UHFFFAOYSA-N 1-[4-[5-[[benzyl(methyl)amino]methyl]-1-[(2,6-difluorophenyl)methyl]-3-[4-(2-hydroxypropan-2-yl)phenyl]-2,4-dioxothieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea Chemical compound C1=CC(NC(=O)NOC)=CC=C1C1=C(CN(C)CC=2C=CC=CC=2)C(C(=O)N(C=2C=CC(=CC=2)C(C)(C)O)C(=O)N2CC=3C(=CC=CC=3F)F)=C2S1 MYVNZIYUALDHCS-UHFFFAOYSA-N 0.000 claims 1
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 8
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| US6828415B2 (en) * | 1993-02-19 | 2004-12-07 | Zentaris Gmbh | Oligopeptide lyophilisate, their preparation and use |
| RU2419435C2 (ru) * | 2005-07-22 | 2011-05-27 | Такеда Фармасьютикал Компани Лимитед | Предотвращающий преждевременную овуляцию агент |
| US20100061976A1 (en) * | 2008-07-24 | 2010-03-11 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Method for treating or preventing osteoporosis by reducing follicle stimulating hormone to cyclic physiological levels in a mammalian subject |
| US20110172249A1 (en) * | 2008-09-03 | 2011-07-14 | Takeda Pharmaceutical Company Limted | Method for improving absorbability of preparation, and preparation having improved absorbability |
| MX2011007326A (es) | 2009-01-08 | 2011-10-19 | Curis Inc | Inhibidores de fosfoinositida 3-quinasa con una porcion de enlace de cinc. |
| US8993634B2 (en) | 2010-06-02 | 2015-03-31 | The Trustees Of The University Of Pennsylvania | Methods and use of compounds that bind to Her2/neu receptor complex |
| US9265739B2 (en) | 2010-06-02 | 2016-02-23 | The Trustees Of The University Of Pennsylvania | Methods and use of compounds that bind to HER2/neu receptor complex |
| PE20141382A1 (es) | 2011-04-01 | 2014-11-04 | Curis Inc | Inhibidor de la fosfoinositida-3-quinasa con un grupo de union a zinc |
| RS57157B1 (sr) * | 2011-11-11 | 2018-07-31 | Gilead Apollo Llc | Acc inhibitori i njihove primene |
| SMT201900255T1 (it) * | 2012-09-28 | 2019-07-11 | Takeda Pharmaceuticals Co | Metodo di produzione di derivato tienopirimidinico |
| US9468681B2 (en) | 2013-03-01 | 2016-10-18 | California Institute Of Technology | Targeted nanoparticles |
| EP2881391A1 (en) | 2013-12-05 | 2015-06-10 | Bayer Pharma Aktiengesellschaft | Spiroindoline carbocycle derivatives and pharmaceutical compositions thereof |
| HUE062269T2 (hu) | 2015-02-26 | 2023-10-28 | Takeda Pharmaceuticals Co | Metoxikarbamid-származékot és mannit részecskéket tartalmazó tabletta |
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| EP3379933B1 (en) | 2015-11-25 | 2023-02-15 | Gilead Apollo, LLC | Fungicidal compositions containing derivatives of 2,4-dioxo-1,4-dihydrothieno[2,3-d]pyrimidine |
| KR20180082557A (ko) | 2015-11-25 | 2018-07-18 | 길리어드 아폴로, 엘엘씨 | 트리아졸 acc 억제제 및 그의 용도 |
| PT3380480T (pt) | 2015-11-25 | 2023-03-14 | Gilead Apollo Llc | Inibidores de pirazol acc e seus usos |
| US20170166583A1 (en) | 2015-11-25 | 2017-06-15 | Gilead Apollo, Llc | Ester acc inhibitors and uses thereof |
| RU2610281C1 (ru) * | 2016-02-26 | 2017-02-08 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | Способ получения 2-фтор-3-метилбут-2-ениламина или его гидрохлорида (Варианты) |
| KR102700008B1 (ko) | 2016-03-02 | 2024-08-29 | 길리어드 아폴로, 엘엘씨 | 티에노피리미딘디온 acc 억제제의 고체 형태 및 그의 제조 방법 |
| MX2019003726A (es) | 2016-09-30 | 2019-09-26 | Myovant Sciences Gmbh | Metodos para tratar fibroides uterinos y endometriosis. |
| BR112019006228A2 (pt) | 2016-09-30 | 2019-06-18 | Myovant Sciences Gmbh | tratamento de câncer de próstata |
| JP6906626B2 (ja) | 2017-03-28 | 2021-07-21 | ギリアード サイエンシーズ， インコーポレイテッド | 肝疾患を処置するための治療的組み合わせ |
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| WO2019178304A1 (en) * | 2018-03-14 | 2019-09-19 | Teva Pharmaceuticals International Gmbh | Solid state forms of relugolix |
| EP3806887A4 (en) | 2018-06-13 | 2022-04-06 | California Institute of Technology | Nanoparticles for crossing the blood brain barrier and methods of treatment using the same |
| BR112021004371A2 (pt) | 2018-09-11 | 2021-05-25 | Curis Inc. | terapia em combinação com um inibidor de fosfoinositídeo 3-quinase com uma porção de ligação a zinco |
| MA54058A (fr) | 2018-10-29 | 2021-09-08 | ObsEva SA | Compositions et méthodes de traitement de l'endométriose interne et de l'endométriose rectovaginale |
| EP3876943A2 (en) | 2018-11-07 | 2021-09-15 | ObsEva S.A. | Compositions and methods for the treatment of estrogen-dependent disorders |
| EP3666776A1 (en) * | 2018-12-11 | 2020-06-17 | Sandoz AG | Hydrate of a gonadotropin-releasing hormone receptor antagonist |
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| US20220267347A1 (en) * | 2019-07-29 | 2022-08-25 | Sunshine Lake Pharma Co., Ltd. | Substituted pyrimidinedione compounds and uses thereof |
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| CN112321602A (zh) * | 2019-08-05 | 2021-02-05 | 苏州鹏旭医药科技有限公司 | 一种瑞卢戈利药物中间体的制备方法 |
| WO2021023877A2 (en) | 2019-08-08 | 2021-02-11 | ObsEva S.A. | Compositions and methods for the treatment of estrogen-dependent disorders |
| AU2020325721A1 (en) | 2019-08-08 | 2022-03-03 | ObsEva S.A. | GnRH antagonists for the treatment of estrogen-dependent disorders |
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| CN111909168B (zh) * | 2020-07-31 | 2022-02-01 | 广东东阳光药业有限公司 | 含氮杂环基取代的嘧啶二酮类化合物及其用途 |
| CN111925379B (zh) * | 2020-07-31 | 2022-02-15 | 广东东阳光药业有限公司 | 含氮杂芳基取代的嘧啶二酮类化合物及其用途 |
| CN112047957B (zh) * | 2020-09-09 | 2022-02-01 | 广东东阳光药业有限公司 | 取代的嘧啶二酮类化合物及其用途 |
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| CN112142757B (zh) * | 2020-09-29 | 2022-02-15 | 广东东阳光药业有限公司 | 五元含氮杂芳基取代的嘧啶二酮类化合物及其用途 |
| WO2022101303A1 (en) | 2020-11-11 | 2022-05-19 | Myovant Sciences Gmbh | Methods of administering relugolix |
| CN112552312B (zh) * | 2020-12-07 | 2022-08-05 | 杭州科巢生物科技有限公司 | 一种瑞卢戈利或其盐的合成方法 |
| CN113620972A (zh) * | 2021-02-02 | 2021-11-09 | 奥锐特药业(天津)有限公司 | 瑞卢戈利新晶型及其制备方法 |
| CN114907370B (zh) | 2021-02-10 | 2023-11-03 | 奥锐特药业(天津)有限公司 | 高纯度的噻吩并嘧啶化合物及其制备方法 |
| CN115073491A (zh) * | 2021-03-12 | 2022-09-20 | 上海医药工业研究院 | 一种瑞卢戈利中间体、其制备方法及其应用 |
| WO2022214645A1 (en) | 2021-04-09 | 2022-10-13 | Farmhispania Group, S.L. | Processes and intermediates for the preparation of relugolix |
| CN113135934A (zh) * | 2021-04-28 | 2021-07-20 | 北京海美源医药科技有限公司 | 用于制备瑞卢戈利的中间体化合物及其制备方法和瑞卢戈利的制备方法 |
| CN115260211B (zh) * | 2021-04-29 | 2024-02-06 | 长春金赛药业有限责任公司 | 含噻吩稠环类衍生物、药物组合物及其制备方法和应用 |
| JP2024540922A (ja) | 2021-10-18 | 2024-11-06 | スミトモ ファーマ スウィッツァーランド ゲーエムベーハー | Ｎ－（４－（１－（２，６－ジフルオロベンジル）－５－（（ジメチルアミノ）メチル）－３－（６－メトキシ－３－ピリダジニル）－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－イル）フェニル）－Ｎ’－メトキシ尿素のエタノール溶媒和物の結晶形 |
| WO2023072284A1 (zh) * | 2021-11-01 | 2023-05-04 | 山东绿叶制药有限公司 | 促性腺素释放激素拮抗剂及其制备方法和应用 |
| CN114230576A (zh) * | 2021-12-21 | 2022-03-25 | 伊诺药物研究(南京)有限公司 | 一种瑞卢戈利的制备方法 |
| CN114989134B (zh) * | 2022-07-14 | 2023-11-14 | 江西同和药业股份有限公司 | 一种噻吩类化合物及其制备方法与应用 |
| CN115417883B (zh) * | 2022-09-16 | 2024-08-27 | 浙江科聚生物医药有限公司 | 一种瑞卢戈利的晶型及其制备方法 |
| WO2024126674A1 (en) | 2022-12-15 | 2024-06-20 | Medichem, S.A. | Process for the preparation of relugolix |
| WO2024222827A1 (zh) * | 2023-04-27 | 2024-10-31 | 山东绿叶制药有限公司 | 一种噻吩并嘧啶类化合物的盐型、晶型及其制备方法和应用 |
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| US6048863A (en) | 1994-04-19 | 2000-04-11 | Takeda Chemical Industries, Ltd. | Condensed-ring thiophene derivatives and thienopyrimidine derivatives, their production and use |
| UY23948A1 (es) | 1995-02-08 | 2001-10-25 | Takeda Chemical Industries Ltd | Derivados de anillos condensados de tiofeno su producción y uso. |
| RU2233284C2 (ru) * | 1999-03-24 | 2004-07-27 | Такеда Кемикал Индастриз, Лтд. | Тиенопиримидиновые производные, способ их получения, фармацевтическая композиция и способ антагонизации гонадотропин-рилизинг гормона |
| TWI225863B (en) * | 1999-03-24 | 2005-01-01 | Takeda Chemical Industries Ltd | Thienopyrimidine compounds, their production and use |
| CA2401379A1 (en) | 2000-02-29 | 2001-09-07 | Junichi Kawakami | Processes for the production of thienopyrimidine derivatives |
| JP2001316391A (ja) * | 2000-02-29 | 2001-11-13 | Takeda Chem Ind Ltd | チエノピリミジン誘導体の製造法 |
| EP1393747A1 (en) | 2000-04-13 | 2004-03-03 | Takeda Chemical Industries, Ltd. | Preventives/remedies for alzheimer's disease |
| JP2001354588A (ja) * | 2000-04-13 | 2001-12-25 | Takeda Chem Ind Ltd | アルツハイマー病予防・治療剤 |
| JP2002068982A (ja) * | 2000-06-14 | 2002-03-08 | Takeda Chem Ind Ltd | 徐放性組成物 |
| AU2001264264A1 (en) | 2000-06-14 | 2001-12-24 | Takeda Chemical Industries Ltd. | Sustained release compositions |
| WO2002002144A1 (en) | 2000-07-05 | 2002-01-10 | Takeda Chemical Industries, Ltd. | Medicinal preparations for treating sex hormone-dependent diseases |
| JP2002080397A (ja) * | 2000-07-05 | 2002-03-19 | Takeda Chem Ind Ltd | 性ホルモン依存性疾患の治療用医薬製剤 |
| JP2002167327A (ja) * | 2000-09-22 | 2002-06-11 | Takeda Chem Ind Ltd | 固形製剤 |
| AU2001288102A1 (en) | 2000-09-22 | 2002-04-02 | Takeda Chemical Industries Ltd. | Solid preparations |
| AU2002218494A1 (en) * | 2000-11-29 | 2002-06-11 | Takeda Chemical Industries Ltd. | Medicinal compositions and process for producing the same |
| AU2002221139A1 (en) * | 2000-12-15 | 2002-06-24 | Takeda Chemical Industries Ltd. | Medicinal compositions of nonpeptidyl gonadotropin-releasing hormone agonist or antagonist, process for producing the same and use thereof |
| JP2004518732A (ja) * | 2001-02-14 | 2004-06-24 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | マトリックスメタロプロテイナーゼ阻害剤としてのチエノ’２，３−ｄピリミジンジオン誘導体 |
| US7569570B2 (en) | 2002-01-30 | 2009-08-04 | Takeda Pharmaceutical Company Limited | Thienopyrimidines, process for preparing the same and use thereof |
| JP5072166B2 (ja) * | 2002-01-30 | 2012-11-14 | 武田薬品工業株式会社 | チエノピリミジン化合物、その製造法および用途 |
| CA2478827A1 (en) | 2002-03-11 | 2003-09-18 | Takeda Chemical Industries, Ltd. | Remedies for sex hormone-dependent disease |
| JP2004002321A (ja) * | 2002-03-11 | 2004-01-08 | Takeda Chem Ind Ltd | 性ホルモン依存性疾患治療剤 |
| JP2004002377A (ja) * | 2002-04-12 | 2004-01-08 | Takeda Chem Ind Ltd | ホットフラッシュ予防・治療剤 |
| WO2003086464A1 (fr) | 2002-04-12 | 2003-10-23 | Takeda Pharmaceutical Company Limited. | Agents pour prevenir/traiter les bouffees de chaleur |
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