CA2663057C - N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase - Google Patents
N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase Download PDFInfo
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- CA2663057C CA2663057C CA2663057A CA2663057A CA2663057C CA 2663057 C CA2663057 C CA 2663057C CA 2663057 A CA2663057 A CA 2663057A CA 2663057 A CA2663057 A CA 2663057A CA 2663057 C CA2663057 C CA 2663057C
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- alkyl
- alkynyl
- alkenyl
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Families Citing this family (159)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003201573B2 (en) * | 2002-01-22 | 2009-02-26 | Biomatera Inc. | Method of drying biodegradable polymers |
| WO2006082030A1 (en) * | 2005-02-04 | 2006-08-10 | Ctg Pharma S.R.L. | New 4-aminoquinoline derivatives as antimalarials |
| DK2559690T3 (en) | 2005-05-10 | 2016-04-25 | Incyte Holdings Corp | Modulators of indoleamine 2,3-dioxygenase and methods of use thereof |
| ES2540561T3 (es) | 2005-12-20 | 2015-07-10 | Incyte Corporation | N-hidroxiamidinoheterociclos como moduladores de indolamina 2,3-dioxigenasa |
| US20080125470A1 (en) | 2006-09-19 | 2008-05-29 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| CL2007002650A1 (es) | 2006-09-19 | 2008-02-08 | Incyte Corp | Compuestos derivados de heterociclo n-hidroxiamino; composicion farmaceutica, util para tratar cancer, infecciones virales y desordenes neurodegenerativos entre otras. |
| WO2008036652A2 (en) * | 2006-09-19 | 2008-03-27 | Incyte Corporation | Amidines as modulators of indoleamine 2,3-dioxygenase |
| US20080182882A1 (en) * | 2006-11-08 | 2008-07-31 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| NZ590268A (en) | 2008-07-08 | 2012-11-30 | Incyte Corp | 1,2,5-oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase |
| KR20150087400A (ko) | 2012-11-20 | 2015-07-29 | 버텍스 파마슈티칼스 인코포레이티드 | 인돌아민 2,3-디옥시게나제의 억제제로서 유용한 화합물 |
| KR102442231B1 (ko) * | 2013-08-30 | 2022-09-13 | 더 보드 오브 리젠츠 오브 더 유니버시티 오브 텍사스 시스템 | 종양 치료를 위한 키누레닌 고갈 효소의 투여 |
| CR20160252A (es) | 2013-11-08 | 2016-09-19 | Incyte Holdings Corp | Proceso para la sintesis de un inhibidor de indolamina 2,3-dioxigenasa |
| EA201990240A1 (ru) | 2013-12-24 | 2019-06-28 | Бристол-Маерс Сквибб Компани | Новые трициклические соединения в качестве противораковых средств |
| ES2901705T3 (es) | 2014-06-06 | 2022-03-23 | Bristol Myers Squibb Co | Anticuerpos contra el receptor del factor de necrosis tumoral inducido por glucocorticoides (GITR) y usos de los mismos |
| JP7080053B2 (ja) | 2014-08-29 | 2022-06-03 | ボード オブ リージェンツ，ザ ユニバーシティ オブ テキサス システム | 腫瘍の治療のための、キヌレニンを枯渇させる酵素の投与 |
| SI3221363T1 (sl) | 2014-11-21 | 2020-09-30 | Bristol-Myers Squibb Company | Protitelesa proti CD73 in njihova uporaba |
| AR103232A1 (es) | 2014-12-22 | 2017-04-26 | Bristol Myers Squibb Co | ANTAGONISTAS DE TGFbR |
| CA2971732A1 (en) | 2014-12-23 | 2016-06-30 | Bristol-Myers Squibb Company | Antibodies to tigit |
| US10983128B2 (en) | 2015-02-05 | 2021-04-20 | Bristol-Myers Squibb Company | CXCL11 and SMICA as predictive biomarkers for efficacy of anti-CTLA4 immunotherapy |
| KR20170122799A (ko) | 2015-03-02 | 2017-11-06 | 리겔 파마슈티칼스, 인크. | TGF-β 억제제 |
| US10399933B2 (en) | 2015-04-03 | 2019-09-03 | Bristol-Myers Squibb Company | Inhibitors of indoleamine-2,3-dioxygenase for the treatment of cancer |
| WO2016162505A1 (en) | 2015-04-08 | 2016-10-13 | F-Star Biotechnology Limited | Her2 binding agent therapies |
| HUE053903T2 (hu) | 2015-04-13 | 2021-07-28 | Five Prime Therapeutics Inc | Kombinációs terápia rák ellen |
| WO2016183114A1 (en) | 2015-05-11 | 2016-11-17 | Bristol-Myers Squibb Company | Tricyclic compounds as anticancer agents |
| US9725449B2 (en) | 2015-05-12 | 2017-08-08 | Bristol-Myers Squibb Company | Tricyclic compounds as anticancer agents |
| WO2016183115A1 (en) | 2015-05-12 | 2016-11-17 | Bristol-Myers Squibb Company | 5h-pyrido[3,2-b]indole compounds as anticancer agents |
| SG10202008304TA (en) | 2015-05-29 | 2020-10-29 | Bristol Myers Squibb Co | Antibodies against ox40 and uses thereof |
| MX2017016502A (es) | 2015-06-29 | 2018-03-12 | Univ Rockefeller | Anticuerpos contra cd40 con actividad agonista mejorada. |
| WO2017019757A1 (en) | 2015-07-28 | 2017-02-02 | Bristol-Myers Squibb Company | Tgf beta receptor antagonists |
| JP2018525415A (ja) | 2015-08-25 | 2018-09-06 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｔｇｆベータ受容体アンタゴニスト |
| JP6936221B2 (ja) | 2015-11-02 | 2021-09-15 | ファイブ プライム セラピューティクス， インコーポレイテッド | Ｃｄ８０細胞外ドメインポリペプチドと、がん治療でのそれらの使用 |
| BR112018010172A2 (pt) | 2015-11-19 | 2018-11-21 | Bristol Myers Squibb Co | anticorpos contra receptor de fator de necrose de tumor induzido por glicocorticoide (gitr) e usos dos mesmos |
| JP7349787B2 (ja) | 2015-11-23 | 2023-09-25 | ファイヴ プライム セラピューティクス インク | 癌治療におけるｆｇｆｒ２阻害剤単独または免疫刺激剤との組み合わせ |
| US10450318B2 (en) | 2015-12-15 | 2019-10-22 | Bristol-Myers Squibb Company | CXCR4 receptor antagonists |
| EP3416725A1 (en) | 2016-02-19 | 2018-12-26 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of obesity |
| US11542486B2 (en) | 2016-03-02 | 2023-01-03 | Board Of Regents, The University Of Texas System | Human kynureninase enzyme variants having improved pharmacological properties |
| KR20230038311A (ko) | 2016-03-04 | 2023-03-17 | 브리스톨-마이어스 스큅 컴퍼니 | 항-cd73 항체와의 조합 요법 |
| SG11201808821WA (en) | 2016-04-18 | 2018-11-29 | Celldex Therapeutics Inc | Agonistic antibodies that bind human cd40 and uses thereof |
| KR20190003687A (ko) | 2016-05-04 | 2019-01-09 | 브리스톨-마이어스 스큅 컴퍼니 | 인돌아민 2,3-디옥시게나제의 억제제 및 그의 사용 방법 |
| KR20190003686A (ko) | 2016-05-04 | 2019-01-09 | 브리스톨-마이어스 스큅 컴퍼니 | 인돌아민 2,3-디옥시게나제의 억제제 및 그의 사용 방법 |
| CN109348714A (zh) | 2016-05-04 | 2019-02-15 | 百时美施贵宝公司 | 吲哚胺2,3-双加氧酶的抑制剂及其使用方法 |
| WO2017192813A1 (en) | 2016-05-04 | 2017-11-09 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| KR20190004743A (ko) | 2016-05-04 | 2019-01-14 | 브리스톨-마이어스 스큅 컴퍼니 | 인돌아민 2,3-디옥시게나제의 억제제 및 그의 사용 방법 |
| AU2017297506A1 (en) | 2016-07-14 | 2019-02-21 | Bristol-Myers Squibb Company | Antibodies against TIM3 and uses thereof |
| WO2018017633A1 (en) | 2016-07-21 | 2018-01-25 | Bristol-Myers Squibb Company | TGF Beta RECEPTOR ANTAGONISTS |
| US11351164B2 (en) | 2016-08-26 | 2022-06-07 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| UY37466A (es) | 2016-11-03 | 2018-01-31 | Phenex Discovery Verwaltungs Gmbh | N-hidroxiamidinheterociclos sustituidos como moduladores de la indolamina 2,3-dioxigenasa |
| PE20191541A1 (es) | 2016-12-22 | 2019-10-23 | Calithera Biosciences Inc | Composiciones y metodos para inhibir la accion de la arginasa |
| US10961239B2 (en) | 2017-01-05 | 2021-03-30 | Bristol-Myers Squibb Company | TGF beta receptor antagonists |
| JP2020506895A (ja) | 2017-01-17 | 2020-03-05 | ボード オブ レジェンツ, ザ ユニバーシティ オブ テキサス システムBoard Of Regents, The University Of Texas System | インドールアミン２，３−ジオキシゲナーゼおよび／またはトリプトファンジオキシゲナーゼの阻害剤として有用な化合物 |
| CN110461326A (zh) * | 2017-03-29 | 2019-11-15 | 默沙东公司 | 作为吲哚胺2,3-双加氧酶(ido)抑制剂的新型经取代n’-羟基甲脒基-1,2,5-噁二唑化合物 |
| CA3057687A1 (en) | 2017-03-31 | 2018-10-04 | Five Prime Therapeutics, Inc. | Combination therapy for cancer using anti-gitr antibodies |
| TWI788340B (zh) | 2017-04-07 | 2023-01-01 | 美商必治妥美雅史谷比公司 | 抗icos促效劑抗體及其用途 |
| SG11201909710XA (en) | 2017-04-21 | 2019-11-28 | Kyn Therapeutics | Indole ahr inhibitors and uses thereof |
| ES2899616T3 (es) | 2017-04-28 | 2022-03-14 | Five Prime Therapeutics Inc | Polipéptidos del dominio extracelular del CD80 para su uso en aumentar los linfocitos T de memoria central |
| WO2018209049A1 (en) | 2017-05-12 | 2018-11-15 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| KR101965348B1 (ko) * | 2017-06-26 | 2019-04-03 | 한국화학연구원 | N'-히드록시인다졸카르복시이미다미드 유도체 화합물, 이의 광학이성질체, 또는 이의 약학적으로 허용가능한 염, 및, 이를 유효성분으로 포함하는 항암용 조성물 |
| US20210078988A1 (en) * | 2017-06-28 | 2021-03-18 | Glaxosmithkline Intellectual Property Development Limited | Modulators of indoleamine 2,3-dioxygenase |
| JP2020525493A (ja) | 2017-06-28 | 2020-08-27 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | インドールアミン２，３−ジオキシゲナーゼのモジュレーター |
| US11236049B2 (en) | 2017-06-30 | 2022-02-01 | Bristol-Myers Squibb Company | Amorphous and crystalline forms of IDO inhibitors |
| KR102709265B1 (ko) | 2017-07-28 | 2024-09-23 | 브리스톨-마이어스 스큅 컴퍼니 | 항암제로서의 시클릭 디뉴클레오티드 |
| CA3073051A1 (en) | 2017-08-17 | 2019-02-21 | Ikena Oncology, Inc. | Ahr inhibitors and uses thereof |
| JP7209697B2 (ja) | 2017-08-31 | 2023-01-20 | ブリストル－マイヤーズ スクイブ カンパニー | 抗癌剤としての環状ジヌクレオチド |
| EP3676279B1 (en) | 2017-08-31 | 2021-12-01 | Bristol-Myers Squibb Company | Cyclic dinucleotides as anticancer agents |
| EP3676277A1 (en) | 2017-08-31 | 2020-07-08 | Bristol-Myers Squibb Company | Cyclic dinucleotides as anticancer agents |
| WO2019043103A1 (en) * | 2017-09-01 | 2019-03-07 | Netherlands Translational Research Center B.V. | 3-HYDROXY-IMIDAZOLIDIN-4-ONE COMPOUNDS AS INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE |
| US11649212B2 (en) | 2017-10-09 | 2023-05-16 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| US11203592B2 (en) | 2017-10-09 | 2021-12-21 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| WO2019075090A1 (en) | 2017-10-10 | 2019-04-18 | Tilos Therapeutics, Inc. | ANTI-LAP ANTIBODIES AND USES THEREOF |
| EP3694867A1 (en) | 2017-10-10 | 2020-08-19 | Bristol-Myers Squibb Company | Cyclic dinucleotides as anticancer agents |
| KR102747388B1 (ko) | 2017-10-16 | 2024-12-26 | 브리스톨-마이어스 스큅 컴퍼니 | 항암제로서의 시클릭 디뉴클레오티드 |
| KR20200074214A (ko) | 2017-11-01 | 2020-06-24 | 브리스톨-마이어스 스큅 컴퍼니 | 암을 치료하는데 사용하기 위한 면역자극 효능작용 항체 |
| US11166959B2 (en) | 2017-11-06 | 2021-11-09 | Bristol-Myers Squibb Company | Isofuranone compounds useful as HPK1 inhibitors |
| US20200352931A1 (en) | 2017-12-12 | 2020-11-12 | Phenex Discovery Verwaltungs-GmbH | Oxalamides as modulators of indoleamine 2,3-dioxygenase |
| US11306149B2 (en) | 2017-12-27 | 2022-04-19 | Bristol-Myers Squibb Company | Anti-CD40 antibodies and uses thereof |
| US11447449B2 (en) | 2018-01-05 | 2022-09-20 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| CN111886255B (zh) | 2018-01-12 | 2025-04-04 | 百时美施贵宝公司 | 抗tim3抗体及其用途 |
| US10519187B2 (en) | 2018-02-13 | 2019-12-31 | Bristol-Myers Squibb Company | Cyclic dinucleotides as anticancer agents |
| KR20200130362A (ko) | 2018-03-08 | 2020-11-18 | 브리스톨-마이어스 스큅 컴퍼니 | 항암제로서의 시클릭 디뉴클레오티드 |
| AU2019239747A1 (en) | 2018-03-21 | 2020-10-08 | Bristol-Myers Squibb Company | Antibodies binding to VISTA at acidic pH |
| EP3768715A1 (en) | 2018-03-23 | 2021-01-27 | Bristol-Myers Squibb Company | Antibodies against mica and/or micb and uses thereof |
| WO2019185870A1 (en) | 2018-03-29 | 2019-10-03 | Phenex Discovery Verwaltungs-GmbH | Spirocyclic compounds as modulators of indoleamine 2,3-dioxygenase |
| CN112218657A (zh) | 2018-04-12 | 2021-01-12 | 百时美施贵宝公司 | Cd73拮抗剂抗体和pd-1/pd-l1轴拮抗剂抗体的抗癌组合疗法 |
| JP2021522211A (ja) | 2018-04-16 | 2021-08-30 | アリーズ セラピューティクス， インコーポレイテッド | Ｅｐ４阻害剤およびその使用 |
| AR115051A1 (es) | 2018-04-16 | 2020-11-25 | Univ Texas | Enzimas quinureninasa humanas y sus usos |
| WO2019206800A1 (en) | 2018-04-24 | 2019-10-31 | Phenex Discovery Verwaltungs-GmbH | Spirocyclic compounds as modulators of indoleamine 2,3-dioxygenase |
| WO2019213340A1 (en) | 2018-05-03 | 2019-11-07 | Bristol-Myers Squibb Company | Uracil derivatives as mer-axl inhibitors |
| ES2950007T3 (es) | 2018-06-27 | 2023-10-04 | Bristol Myers Squibb Co | Compuestos de naftiridinona útiles como activadores de células T |
| BR112020026681A2 (pt) | 2018-06-27 | 2021-04-06 | Bristol-Myers Squibb Company | Compostos naftiridinona substituídos úteis como ativadores de célula t |
| EP3820904A2 (en) | 2018-07-09 | 2021-05-19 | Five Prime Therapeutics, Inc. | Antibodies binding to ilt4 |
| BR112021000303A2 (pt) | 2018-07-11 | 2021-04-13 | Five Prime Therapeutics, Inc. | Anticorpos que se ligam a vista em ph ácido |
| US11046649B2 (en) | 2018-07-17 | 2021-06-29 | Board Of Regents, The University Of Texas System | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
| WO2020023355A1 (en) | 2018-07-23 | 2020-01-30 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| US12145927B2 (en) | 2018-07-23 | 2024-11-19 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| US11253525B2 (en) | 2018-08-29 | 2022-02-22 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| US10959986B2 (en) | 2018-08-29 | 2021-03-30 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase and methods of their use |
| CN113164780A (zh) | 2018-10-10 | 2021-07-23 | 泰洛斯治疗公司 | 抗lap抗体变体及其用途 |
| KR20210092769A (ko) | 2018-11-16 | 2021-07-26 | 브리스톨-마이어스 스큅 컴퍼니 | 항-nkg2a 항체 및 그의 용도 |
| WO2020231713A1 (en) | 2019-05-13 | 2020-11-19 | Bristol-Myers Squibb Company | AGONISTS OF ROR GAMMAt |
| US20230295087A1 (en) | 2019-05-13 | 2023-09-21 | Bristol-Myers Squibb Company | AGONISTS OF ROR GAMMAt |
| US20220306630A1 (en) | 2019-08-06 | 2022-09-29 | Bristol-Myers Squibb Company | AGONISTS OF ROR GAMMAt |
| AR119821A1 (es) | 2019-08-28 | 2022-01-12 | Bristol Myers Squibb Co | Compuestos de piridopirimidinonilo sustituidos útiles como activadores de células t |
| EP4031575A1 (en) | 2019-09-19 | 2022-07-27 | Bristol-Myers Squibb Company | Antibodies binding to vista at acidic ph |
| KR20220103753A (ko) | 2019-11-19 | 2022-07-22 | 브리스톨-마이어스 스큅 컴퍼니 | 헬리오스 단백질의 억제제로서 유용한 화합물 |
| CA3159071A1 (en) | 2019-11-26 | 2021-06-03 | Tamar I. ROSENBAUM | Salts/cocrystals of (r)-n-(4-chlorophenyl)-2-((1s,4s)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide |
| AU2020394424A1 (en) | 2019-11-26 | 2022-06-16 | Ikena Oncology, Inc. | Polymorphic carbazole derivatives and uses thereof |
| IL294269A (en) | 2019-12-23 | 2022-08-01 | Bristol Myers Squibb Co | Substituted quinolinonyl piperazine compounds useful as t cell activators |
| AR120823A1 (es) | 2019-12-23 | 2022-03-23 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos útiles como activadores de células t |
| IL294273A (en) | 2019-12-23 | 2022-08-01 | Bristol Myers Squibb Co | Substituted heteroaryl compounds are useful as t-cell activators |
| ES3038401T3 (en) | 2019-12-23 | 2025-10-13 | Bristol Myers Squibb Co | Substituted quinazolinyl compounds useful as t cell activators |
| BR112022012222A2 (pt) | 2019-12-23 | 2022-09-13 | Bristol Myers Squibb Co | Derivados de piperazina substituídos úteis como ativadores de células t |
| CA3166898A1 (en) | 2020-01-06 | 2021-07-15 | Hifibio (Hk) Limited | Anti-tnfr2 antibody and uses thereof |
| BR112022013494A2 (pt) | 2020-01-07 | 2022-09-13 | Hifibio Hk Ltd | Anticorpo anti-galectina-9 e usos do mesmo |
| EP4090663A1 (en) | 2020-01-15 | 2022-11-23 | Blueprint Medicines Corporation | Map4k1 inhibitors |
| US20230140384A1 (en) | 2020-03-09 | 2023-05-04 | Bristol-Myers Squibb Company | Antibodies to cd40 with enhanced agonist activity |
| TW202140441A (zh) | 2020-03-23 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 經取代之側氧基異吲哚啉化合物 |
| US20230272056A1 (en) | 2020-04-09 | 2023-08-31 | Merck Sharp & Dohme Llc | Affinity matured anti-lap antibodies and uses thereof |
| WO2021231732A1 (en) | 2020-05-15 | 2021-11-18 | Bristol-Myers Squibb Company | Antibodies to garp |
| WO2021258010A1 (en) | 2020-06-19 | 2021-12-23 | Gossamer Bio Services, Inc. | Oxime compounds useful as t cell activators |
| IL300537A (en) | 2020-08-10 | 2023-04-01 | Gv20 Therapeutics Llc | Compositions and methods for treating autoimmune diseases and cancer by targeting IGSF8 |
| US20230416382A1 (en) | 2020-10-14 | 2023-12-28 | Five Prime Therapeutics, Inc. | Anti-c-c chemokine receptor 8 (ccr8) antibodies and methods of use thereof |
| CN116964050A (zh) | 2020-12-16 | 2023-10-27 | 戈萨默生物服务公司 | 可用作t细胞激活剂的化合物 |
| WO2022169921A1 (en) | 2021-02-04 | 2022-08-11 | Bristol-Myers Squibb Company | Benzofuran compounds as sting agonists |
| AU2022221124A1 (en) | 2021-02-12 | 2023-08-03 | F. Hoffmann-La Roche Ag | Bicyclic tetrahydroazepine derivatives for the treatment of cancer |
| JP2024510176A (ja) | 2021-03-08 | 2024-03-06 | ブループリント メディシンズ コーポレイション | Ｍａｐ４ｋ１阻害剤 |
| US11918582B2 (en) | 2021-03-15 | 2024-03-05 | Rapt Therapeutics, Inc. | Pyrazole pyrimidine compounds and uses thereof |
| JP2024514530A (ja) | 2021-04-02 | 2024-04-02 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 切断型ｃｄｃｐ１に対する抗体およびその使用 |
| MX2023011408A (es) | 2021-04-05 | 2024-01-18 | Bristol Myers Squibb Co | Compuestos de oxoisoindolina sustituidos con piridinilo para el tratamiento de cancer. |
| AR125298A1 (es) | 2021-04-06 | 2023-07-05 | Bristol Myers Squibb Co | Compuestos de oxoisoindolina sustituidos con piridinilo |
| AU2022312496A1 (en) | 2021-07-14 | 2024-02-22 | Blueprint Medicines Corporation | Heterocyclic compounds as map4k1 inhibitors |
| TW202321238A (zh) | 2021-07-15 | 2023-06-01 | 美商纜圖藥品公司 | Ｍａｐ４ｋ１抑制劑 |
| WO2023122777A1 (en) | 2021-12-22 | 2023-06-29 | Gossamer Bio Services, Inc. | Oxime derivatives useful as t cell activators |
| WO2023122772A1 (en) | 2021-12-22 | 2023-06-29 | Gossamer Bio Services, Inc. | Oxime derivatives useful as t cell activators |
| WO2023122778A1 (en) | 2021-12-22 | 2023-06-29 | Gossamer Bio Services, Inc. | Pyridazinone derivatives useful as t cell activators |
| JP2025503312A (ja) | 2022-02-01 | 2025-01-30 | アルビナス・オペレーションズ・インコーポレイテッド | Ｄｇｋ標的化化合物およびその使用 |
| WO2024036100A1 (en) | 2022-08-08 | 2024-02-15 | Bristol-Myers Squibb Company | Substituted tetrazolyl compounds useful as t cell activators |
| WO2024036101A1 (en) | 2022-08-09 | 2024-02-15 | Bristol-Myers Squibb Company | Tertiary amine substituted bicyclic compounds useful as t cell activators |
| TW202417439A (zh) | 2022-08-11 | 2024-05-01 | 瑞士商赫孚孟拉羅股份公司 | 雙環四氫噻吖呯衍生物 |
| WO2024033458A1 (en) | 2022-08-11 | 2024-02-15 | F. Hoffmann-La Roche Ag | Bicyclic tetrahydroazepine derivatives |
| JP2025526727A (ja) | 2022-08-11 | 2025-08-15 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | 二環式テトラヒドロチアゼピン誘導体 |
| MA71728A (fr) | 2022-08-11 | 2025-05-30 | F. Hoffmann-La Roche Ag | Dérivés bicycliques de tétrahydrothiazépine |
| WO2024137865A1 (en) | 2022-12-22 | 2024-06-27 | Gossamer Bio Services, Inc. | Compounds useful as t cell activators |
| CN121057732A (zh) | 2023-05-08 | 2025-12-02 | 百时美施贵宝公司 | 经取代的苯基噁唑酮化合物 |
| AU2024269298A1 (en) | 2023-05-10 | 2025-11-27 | Blueprint Medicines Corporation | Gsk3a inhibitors and methods of use thereof |
| WO2024249540A1 (en) | 2023-05-31 | 2024-12-05 | Bristol-Myers Squibb Company | Substituted oxazolone compound for decreasing levels of ikzf1-4 proteins |
| WO2024254227A1 (en) | 2023-06-07 | 2024-12-12 | Bristol-Myers Squibb Company | Spirocyclic substituted oxoisoindolinyl piperidine-2,6-dione compound |
| WO2024263853A1 (en) | 2023-06-23 | 2024-12-26 | Bristol-Myers Squibb Company | Substituted oxoisoindolinyl piperidine-2,6-dione compound as anticancer agent |
| WO2025030002A2 (en) | 2023-08-02 | 2025-02-06 | Arvinas Operations, Inc. | Dgk targeting compounds and uses thereof |
| AR133696A1 (es) | 2023-09-02 | 2025-10-22 | Bristol Myers Squibb Co | Compuestos de fenil oxooxazolil piperidinadiona sustituida |
| WO2025064197A1 (en) | 2023-09-02 | 2025-03-27 | Bristol-Myers Squibb Company | Substituted azetidinyl oxoisoindolinyl piperidine-2,6-dione compounds |
| TW202525792A (zh) | 2023-09-13 | 2025-07-01 | 美商必治妥美雅史谷比公司 | 經取代之側氧異吲哚啉基哌啶－２，６－二酮化合物 |
| WO2025096505A1 (en) | 2023-10-31 | 2025-05-08 | Bristol-Myers Squibb Company | Ubiquitin specific processing protease 1 (usp1) compounds |
| WO2025096490A1 (en) | 2023-10-31 | 2025-05-08 | Bristol-Myers Squibb Company | Ubiquitin specific processing protease 1 (usp1) compounds |
| WO2025096488A1 (en) | 2023-10-31 | 2025-05-08 | Bristol-Myers Squibb Company | Ubiquitin specific processing protease 1 (usp1) compounds |
| WO2025096494A1 (en) | 2023-10-31 | 2025-05-08 | Bristol-Myers Squibb Company | Ubiquitin specific processing protease 1 (usp1) compounds |
| WO2025096487A1 (en) | 2023-10-31 | 2025-05-08 | Bristol-Myers Squibb Company | Ubiquitin specific processing protease 1 (usp1) compounds |
| WO2025096489A1 (en) | 2023-10-31 | 2025-05-08 | Bristol-Myers Squibb Company | Ubiquitin specific processing protease 1 (usp1) compounds |
| US20250145590A1 (en) | 2023-10-31 | 2025-05-08 | Bristol-Myers Squibb Company | Ubiquitin specific processing protease 1 (usp1) compounds |
| WO2025226767A1 (en) | 2024-04-24 | 2025-10-30 | Bristol-Myers Squibb Company | Substituted 3-(5-(6-aminopyridin-2-yl)-4-fluoro-1-oxoisoindolin-2-yl)piperidine-2,6-dione compounds for use in the treatment of cancer |
Family Cites Families (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3354174A (en) | 1964-02-19 | 1967-11-21 | Sterling Drug Inc | 1-and 2-benzimidazolyl-lower-alkylamidoximes, amidines-, and guanidines |
| US3286855A (en) * | 1965-06-01 | 1966-11-22 | Standard Trailer Company | Crane extension and resulting crane assembly |
| US3553228A (en) * | 1967-09-26 | 1971-01-05 | Colgate Palmolive Co | 3-substituted-4h(1)benzopyrano(3,4-d) isoxazoles |
| DE2040628A1 (de) | 1970-08-17 | 1972-02-24 | Fahlberg List Veb | Neue herbizide Mittel |
| US3948928A (en) * | 1972-03-17 | 1976-04-06 | Dainippon Pharmaceutical Co., Ltd. | 3-Substituted-1,2-benzisoxazoles and pharmaceutically acceptable acid addition salts thereof |
| JPS5621033B2 (enExample) * | 1973-09-05 | 1981-05-16 | ||
| FR2323683A1 (fr) | 1975-09-11 | 1977-04-08 | Philagro Sa | Nouveaux derives d'amidoximes, leur preparation et les compositions qui les contiennent |
| DE2640484A1 (de) * | 1975-09-11 | 1977-04-07 | Philagro Sa | Amidoxim-derivate, ihre herstellung und verwendung |
| US4323681A (en) * | 1980-09-29 | 1982-04-06 | American Home Products Corporation | 4-Amino-2-substituted-5-pyrimidinecarboxamidoximes and carbothioamides |
| JPS58208275A (ja) | 1982-05-20 | 1983-12-03 | Lion Corp | ５−アミノ−ピラゾ−ル誘導体及び該化合物を含有する抗腫瘍剤 |
| DE3462259D1 (de) * | 1983-07-22 | 1987-03-05 | Bayer Ag | Substituted furazans |
| JPS60193968A (ja) | 1984-03-13 | 1985-10-02 | Toyo Jozo Co Ltd | シクロペンテン環を有するイミダゾ−ルアミドオキシムおよびその製造法 |
| JPS6259283A (ja) | 1985-09-10 | 1987-03-14 | Kaken Pharmaceut Co Ltd | セフアロスポリン化合物 |
| JP2696342B2 (ja) | 1988-06-27 | 1998-01-14 | 日本曹達株式会社 | アミジン誘導体、その製造方法及び殺ダニ剤・農園芸用殺菌剤 |
| EP0352832B1 (en) | 1988-07-05 | 1992-05-06 | Akzo N.V. | Compounds with bronchodilator activity |
| JPH04297449A (ja) | 1991-03-27 | 1992-10-21 | Hokko Chem Ind Co Ltd | Ｎ−ヒドロキシベンジルグアニジン誘導体および農園芸用殺菌剤 |
| JPH05186458A (ja) | 1991-04-26 | 1993-07-27 | Japan Tobacco Inc | 新規なベンゾピラン誘導体 |
| FR2677019B1 (fr) * | 1991-05-27 | 1994-11-25 | Pf Medicament | Nouvelles piperidines disubstituees-1,4, leur preparation et leur application en therapeutique. |
| JP2709677B2 (ja) | 1992-06-19 | 1998-02-04 | 株式会社大塚製薬工場 | ホスホン酸ジエステル誘導体 |
| FR2720396B1 (fr) * | 1994-05-27 | 1996-06-28 | Adir | Nouveaux N-pyridyl carboxamides et dérivés leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| US5731315A (en) * | 1995-06-07 | 1998-03-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted sulfonic acid n- (aminoiminomethyl)phenylalkyl!-azaheterocyclamide compounds |
| US5883102A (en) | 1995-10-17 | 1999-03-16 | Astra Pharmaceuticals Limited | Pharmaceutically active compounds |
| AU1730497A (en) | 1996-02-17 | 1997-09-02 | Agrevo Uk Limited | Fungicidal 1,2,4-oxadiazoles and analogues |
| US5955495A (en) | 1996-05-03 | 1999-09-21 | Hoffmann-La Roche Inc. | Method of treating diseases of the CNS |
| JPH11171702A (ja) | 1997-09-24 | 1999-06-29 | Takeda Chem Ind Ltd | 害虫防除方法 |
| AU1628699A (en) | 1997-12-05 | 1999-06-28 | Medical College Of Georgia Research Institute, Inc. | High-affinity tryptophan transporter |
| DE69822204T2 (de) | 1997-12-10 | 2005-02-17 | Dainippon Ink And Chemicals, Inc. | Oximderivate und sie enthaltende landwirtschaftliche chemikalien |
| WO1999062903A1 (en) | 1998-06-02 | 1999-12-09 | Takeda Chemical Industries, Ltd. | Oxadiazoline derivatives and their use as insecticides |
| FR2784678B1 (fr) | 1998-09-23 | 2002-11-29 | Sod Conseils Rech Applic | Nouveaux derives de n-(iminomethyl)amines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
| DE60010988T2 (de) | 1999-03-03 | 2005-06-09 | Samjin Pharmaceutical Co., Ltd. | Piperazinderivate und verfahren zu ihrer herstellung |
| SK14222001A3 (sk) | 1999-04-09 | 2002-07-02 | Basf Aktiengesellschaft | Prekurzory trombínových inhibítorov |
| WO2000071517A1 (en) | 1999-05-24 | 2000-11-30 | Mitsubishi Pharma Corporation | Phenoxypropylamine compounds |
| JP2001158786A (ja) | 1999-11-30 | 2001-06-12 | Takeda Chem Ind Ltd | 哺乳動物の外部寄生虫防除剤 |
| JP2001158785A (ja) | 1999-11-30 | 2001-06-12 | Takeda Chem Ind Ltd | 農薬組成物 |
| ATE376996T1 (de) * | 2000-01-13 | 2007-11-15 | Amgen Inc | Antibakterielle mittel |
| PL202623B1 (pl) | 2000-06-28 | 2009-07-31 | Smithkline Beecham Plc | Sposób wytwarzania drobno zmielonego preparatu substancji leczniczej, drobno zmielona substancja lecznicza wytworzona tym sposobem i zawierająca ją kompozycja farmaceutyczna |
| GB0108102D0 (en) | 2001-03-30 | 2001-05-23 | Pfizer Ltd | Compounds |
| US7115639B2 (en) * | 2001-06-18 | 2006-10-03 | Applied Research Systems Ars Holding N.V. | Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists |
| GB0208224D0 (en) | 2002-04-10 | 2002-05-22 | Celltech R&D Ltd | Chemical compounds |
| US20030194803A1 (en) | 2002-04-12 | 2003-10-16 | Mellor Andrew L. | Antigen-presenting cell populations and their use as reagents for enhancing or reducing immune tolerance |
| ZA200408711B (en) | 2002-05-28 | 2006-10-25 | Dimensional Pharamaceuticals I | Novel thiophene amidines, composition thereof, and methods of treating complement-mediated diseases and conditions |
| US7157462B2 (en) | 2002-09-24 | 2007-01-02 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| EP1606285A4 (en) | 2003-03-27 | 2009-03-18 | Lankenau Inst Medical Res | NEW IDO HEMMER AND APPLICATION PROCEDURES |
| US7598287B2 (en) * | 2003-04-01 | 2009-10-06 | Medical College Of Georgia Research Institute, Inc. | Use of inhibitors of indoleamine-2,3-dioxygenase in combination with other therapeutic modalities |
| ATE536353T1 (de) | 2003-08-20 | 2011-12-15 | Vertex Pharma | 2-(4-amino-1,2,5-oxadiazol-4-yl)-imidazol- verbindungen als protein kinase inhibitoren |
| DE10348022A1 (de) | 2003-10-15 | 2005-05-25 | Imtm Gmbh | Neue Dipeptidylpeptidase IV-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
| DE10348023A1 (de) * | 2003-10-15 | 2005-05-19 | Imtm Gmbh | Neue Alanyl-Aminopeptidasen-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
| JP4970946B2 (ja) * | 2004-09-08 | 2012-07-11 | 田辺三菱製薬株式会社 | モルホリン化合物 |
| US8193359B2 (en) | 2004-12-24 | 2012-06-05 | Prosidion Limited | G-protein coupled receptor agonists |
| US7429667B2 (en) * | 2005-01-20 | 2008-09-30 | Ardea Biosciences, Inc. | Phenylamino isothiazole carboxamidines as MEK inhibitors |
| DK2559690T3 (en) | 2005-05-10 | 2016-04-25 | Incyte Holdings Corp | Modulators of indoleamine 2,3-dioxygenase and methods of use thereof |
| WO2006133417A1 (en) | 2005-06-07 | 2006-12-14 | Valeant Pharmaceuticals International | Phenylamino isothiazole carboxamidines as mek inhibitors |
| DE102005060466A1 (de) | 2005-12-17 | 2007-06-28 | Bayer Cropscience Ag | Carboxamide |
| ES2540561T3 (es) | 2005-12-20 | 2015-07-10 | Incyte Corporation | N-hidroxiamidinoheterociclos como moduladores de indolamina 2,3-dioxigenasa |
| WO2007095050A2 (en) * | 2006-02-09 | 2007-08-23 | Incyte Corporation | N-hydroxyguanidines as modulators of indoleamine 2,3-dioxygenase |
| JP4297449B2 (ja) | 2006-05-12 | 2009-07-15 | 株式会社サクラクレパス | 墨汁 |
| WO2008036652A2 (en) | 2006-09-19 | 2008-03-27 | Incyte Corporation | Amidines as modulators of indoleamine 2,3-dioxygenase |
| US20080125470A1 (en) * | 2006-09-19 | 2008-05-29 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| CL2007002650A1 (es) * | 2006-09-19 | 2008-02-08 | Incyte Corp | Compuestos derivados de heterociclo n-hidroxiamino; composicion farmaceutica, util para tratar cancer, infecciones virales y desordenes neurodegenerativos entre otras. |
| US20080119491A1 (en) * | 2006-09-19 | 2008-05-22 | Incyte Corporation | Amidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| US20080182882A1 (en) * | 2006-11-08 | 2008-07-31 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| CN101679297B (zh) | 2006-12-08 | 2012-01-11 | 埃克塞利希斯股份有限公司 | Lxr和fxr调节剂 |
| CL2008000066A1 (es) * | 2007-01-12 | 2008-08-01 | Smithkline Beecham Corp | Compuestos derivados de (5-hidroxi-3-oxo-2,3-dihidropiridazina-4-carbonil)glicina, inhibidores de hif prolil hidroxilasas; procedimiento de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso en el tratamiento de la anem |
| AU2008345225A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| NZ590268A (en) * | 2008-07-08 | 2012-11-30 | Incyte Corp | 1,2,5-oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase |
-
2007
- 2007-09-18 US US11/856,967 patent/US20080125470A1/en not_active Abandoned
- 2007-09-18 WO PCT/US2007/078745 patent/WO2008036642A2/en not_active Ceased
- 2007-09-18 EP EP07814905.1A patent/EP2064207B1/en active Active
- 2007-09-18 JP JP2009529341A patent/JP5319532B2/ja active Active
- 2007-09-18 ES ES07814905.1T patent/ES2444574T3/es active Active
- 2007-09-18 CA CA2663057A patent/CA2663057C/en active Active
-
2011
- 2011-03-23 US US13/070,069 patent/US8377976B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2064207B1 (en) | 2013-11-06 |
| US8377976B2 (en) | 2013-02-19 |
| WO2008036642A2 (en) | 2008-03-27 |
| ES2444574T3 (es) | 2014-02-25 |
| EP2064207A2 (en) | 2009-06-03 |
| CA2663057A1 (en) | 2008-03-27 |
| US20080125470A1 (en) | 2008-05-29 |
| JP2010504346A (ja) | 2010-02-12 |
| US20110172279A1 (en) | 2011-07-14 |
| JP5319532B2 (ja) | 2013-10-16 |
| WO2008036642A3 (en) | 2008-08-07 |
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