TW201815764A - 作為免疫調節劑之化合物 - Google Patents
作為免疫調節劑之化合物 Download PDFInfo
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- TW201815764A TW201815764A TW106129492A TW106129492A TW201815764A TW 201815764 A TW201815764 A TW 201815764A TW 106129492 A TW106129492 A TW 106129492A TW 106129492 A TW106129492 A TW 106129492A TW 201815764 A TW201815764 A TW 201815764A
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- bis
- oxy
- biphenyl
- dimethyl
- diyl
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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| TWI826492B (zh) | 2018-07-27 | 2023-12-21 | 加拿大商愛彼特生物製藥公司 | 經取代四氫環戊[c]吡咯、經取代二氫吡咯,其類似物及使用其之方法 |
| WO2020028097A1 (en) | 2018-08-01 | 2020-02-06 | Gilead Sciences, Inc. | Solid forms of (r)-11-(methoxymethyl)-12-(3-methoxypropoxy)-3,3-dimethyl-8-0x0-2,3,8,13b-tetrahydro-1h-pyrido[2,1-a]pyrrolo[1,2-c] phthalazine-7-c arboxylic acid |
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| CN117105933A (zh) | 2018-10-31 | 2023-11-24 | 吉利德科学公司 | 具有hpk1抑制活性的取代的6-氮杂苯并咪唑化合物 |
| CN113227089B (zh) | 2018-10-31 | 2024-07-05 | 吉利德科学公司 | 作为hpk1抑制剂的取代的6-氮杂苯并咪唑化合物 |
| AU2019373702A1 (en) | 2018-11-02 | 2021-06-24 | Shanghai Maxinovel Pharmaceuticals Co., Ltd. | Diphenyl-like compound, intermediate thereof, preparation method therefor, pharmaceutical composition thereof and uses thereof |
| TWI827760B (zh) | 2018-12-12 | 2024-01-01 | 加拿大商愛彼特生物製藥公司 | 經取代之芳基甲基脲類及雜芳基甲基脲類、其類似物及其使用方法 |
| WO2020144332A1 (en) * | 2019-01-11 | 2020-07-16 | Fundació Institut D'investigació Biomèdica De Bellvitge (Idibell) | Fusion protein with immunosuppressive activity |
| EP3935065A1 (en) | 2019-03-07 | 2022-01-12 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 3'3'-cyclic dinucleotide analogue comprising a cyclopentanyl modified nucleotide as sting modulator |
| US20220143061A1 (en) | 2019-03-07 | 2022-05-12 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotides and prodrugs thereof |
| EP3934757B1 (en) | 2019-03-07 | 2023-02-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 2'3'-cyclic dinucleotides and prodrugs thereof |
| JP2022526960A (ja) | 2019-03-28 | 2022-05-27 | ブリストル-マイヤーズ スクイブ カンパニー | 腫瘍を処置する方法 |
| EP3946625A1 (en) | 2019-03-28 | 2022-02-09 | Bristol-Myers Squibb Company | Methods of treating tumor |
| TWI751517B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TWI751516B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| MX2021013819A (es) | 2019-05-15 | 2022-02-10 | Chemocentryx Inc | Compuestos de triarilo para el tratamiento de enfermedades asociadas a pd-l1. |
| KR20220010535A (ko) * | 2019-05-21 | 2022-01-25 | 브리스톨-마이어스 스큅 컴퍼니 | 면역조정제 |
| EP3972695A1 (en) | 2019-05-23 | 2022-03-30 | Gilead Sciences, Inc. | Substituted exo-methylene-oxindoles which are hpk1/map4k1 inhibitors |
| CN114174538A (zh) | 2019-05-30 | 2022-03-11 | 百时美施贵宝公司 | 适合于免疫肿瘤学疗法的多肿瘤基因特征 |
| KR20220016155A (ko) | 2019-05-30 | 2022-02-08 | 브리스톨-마이어스 스큅 컴퍼니 | 면역-종양학 (i-o) 요법에 적합한 대상체를 확인하는 방법 |
| EP3977132A1 (en) | 2019-05-30 | 2022-04-06 | Bristol-Myers Squibb Company | Cell localization signature and combination therapy |
| CN112028870B (zh) * | 2019-06-04 | 2021-11-05 | 中国科学院上海药物研究所 | 一种具有苄氧基芳环结构的化合物,其制备方法和用途 |
| BR112021023750A2 (pt) | 2019-06-20 | 2022-01-11 | Chemocentryx Inc | Compostos para tratamento de doenças pd-l1 |
| MX2022000318A (es) | 2019-07-10 | 2022-02-10 | Chemocentryx Inc | Indanos como inhibidores de pd-l1. |
| WO2021011891A1 (en) | 2019-07-18 | 2021-01-21 | Gilead Sciences, Inc. | Long-acting formulations of tenofovir alafenamide |
| EP4017476A1 (en) | 2019-08-19 | 2022-06-29 | Gilead Sciences, Inc. | Pharmaceutical formulations of tenofovir alafenamide |
| CN111909108B (zh) * | 2019-09-02 | 2023-05-02 | 中国药科大学 | 联苯类化合物及其制备方法和医药用途 |
| BR112022004316A2 (pt) | 2019-09-22 | 2022-06-21 | Bristol Myers Squibb Co | Caracterização espacial quantitativa para terapia de antagonista lag-3 |
| HRP20241379T1 (hr) | 2019-09-30 | 2024-12-20 | Gilead Sciences, Inc. | Cjepiva za hbv i postupci za liječenje hbv |
| EP4037776A1 (en) * | 2019-10-04 | 2022-08-10 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| MX2022004450A (es) | 2019-10-16 | 2022-05-03 | Chemocentryx Inc | Aminas de heteroaril-bifenilo para el tratamiento de enfermedades pd-l1. |
| CN114585359B (zh) | 2019-10-16 | 2025-08-12 | 凯莫森特里克斯股份有限公司 | 用于治疗pd-l1疾病的杂芳基联苯酰胺 |
| KR20220093349A (ko) | 2019-11-08 | 2022-07-05 | 브리스톨-마이어스 스큅 컴퍼니 | 흑색종에 대한 lag-3 길항제 요법 |
| ES3022990T3 (en) | 2019-12-06 | 2025-05-29 | Prec Biosciences Inc | Optimized engineered meganucleases having specificity for a recognition sequence in the hepatitis b virus genome |
| TWI845826B (zh) | 2020-03-20 | 2024-06-21 | 美商基利科學股份有限公司 | 4'-c-經取代-2-鹵基-2'-去氧腺苷核苷之前藥及其製造與使用方法 |
| IL297908A (en) | 2020-05-05 | 2023-01-01 | Teon Therapeutics Inc | Cannabinoid receptor type 2 (cb2) modulators and uses thereof |
| MX2023002332A (es) | 2020-08-28 | 2023-03-21 | Bristol Myers Squibb Co | Terapia con antagonistas del gen 3 de activacion de linfocitos (lag-3) para carcinoma hepatocelular. |
| CA3190660A1 (en) | 2020-08-31 | 2022-03-03 | George C. Lee | Cell localization signature and immunotherapy |
| WO2022052926A1 (zh) | 2020-09-09 | 2022-03-17 | 广州再极医药科技有限公司 | 芳香乙烯类化合物、其制备方法、中间体、药物组合物及其应用 |
| WO2022055542A1 (en) | 2020-09-10 | 2022-03-17 | Nammi Therapeutics, Inc. | Formulated and/or co-formulated liposome compositions containing pd-1 antagonist prodrugs useful in the treatment of cancer and methods thereof |
| CA3196496A1 (en) | 2020-10-23 | 2022-04-28 | Laurence David TOMS | Lag-3 antagonist therapy for lung cancer |
| WO2022120179A1 (en) | 2020-12-03 | 2022-06-09 | Bristol-Myers Squibb Company | Multi-tumor gene signatures and uses thereof |
| JP2024514245A (ja) | 2021-03-29 | 2024-03-29 | ジュノー セラピューティクス インコーポレイテッド | チェックポイント阻害剤療法とcar t細胞療法との組合せを用いた投薬および処置のための方法 |
| CN113135895A (zh) * | 2021-04-30 | 2021-07-20 | 中国药科大学 | 一种新型联苯类衍生物及其制备方法与医药用途 |
| TW202348237A (zh) | 2021-05-13 | 2023-12-16 | 美商基利科學股份有限公司 | TLR8調節化合物及抗HBV siRNA療法之組合 |
| EP4351657A1 (en) | 2021-06-11 | 2024-04-17 | Gilead Sciences, Inc. | Combination mcl-1 inhibitors with anti-body drug conjugates |
| AU2022291381B2 (en) | 2021-06-11 | 2025-04-24 | Gilead Sciences, Inc. | Combination mcl-1 inhibitors with anti-cancer agents |
| JP7686091B2 (ja) | 2021-06-23 | 2025-05-30 | ギリアード サイエンシーズ, インコーポレイテッド | ジアシルグリセロールキナーゼ調節化合物 |
| CN117480155A (zh) | 2021-06-23 | 2024-01-30 | 吉利德科学公司 | 二酰基甘油激酶调节化合物 |
| EP4359415A1 (en) | 2021-06-23 | 2024-05-01 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| CN117377671A (zh) | 2021-06-23 | 2024-01-09 | 吉利德科学公司 | 二酰基甘油激酶调节化合物 |
| CN115677665B (zh) * | 2021-07-26 | 2024-04-19 | 中国药科大学 | 含联苯类衍生物及其医药用途 |
| TW202325306A (zh) | 2021-09-02 | 2023-07-01 | 美商天恩治療有限公司 | 改良免疫細胞之生長及功能的方法 |
| CN118176214A (zh) | 2021-10-29 | 2024-06-11 | 百时美施贵宝公司 | 血液癌症的lag-3拮抗剂疗法 |
| WO2023081730A1 (en) | 2021-11-03 | 2023-05-11 | Teon Therapeutics, Inc. | 4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide derivatives as cannabinoid cb2 receptor modulators for the treatment of cancer |
| WO2023097211A1 (en) | 2021-11-24 | 2023-06-01 | The University Of Southern California | Methods for enhancing immune checkpoint inhibitor therapy |
| MX2024008831A (es) | 2022-01-26 | 2024-07-25 | Bristol Myers Squibb Co | Terapia combinada para carcinoma hepatocelular. |
| CN119731651A (zh) | 2022-04-08 | 2025-03-28 | 百时美施贵宝公司 | 三级淋巴结构的机器学习标识、分类和量化 |
| EP4554943A1 (en) | 2022-07-14 | 2025-05-21 | Teon Therapeutics, Inc. | Adenosine receptor antagonists and uses thereof |
| WO2024137776A1 (en) | 2022-12-21 | 2024-06-27 | Bristol-Myers Squibb Company | Combination therapy for lung cancer |
| AU2024224371A1 (en) | 2023-02-23 | 2025-08-07 | Sunshine Lake Pharma Co., Ltd. | Pyridopyrimidine derivative and use thereof |
| WO2024196952A1 (en) | 2023-03-20 | 2024-09-26 | Bristol-Myers Squibb Company | Tumor subtype assessment for cancer therapy |
| US20250345389A1 (en) | 2024-05-13 | 2025-11-13 | Gilead Sciences, Inc. | Combination therapies |
| WO2025240246A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| US20250345390A1 (en) | 2024-05-13 | 2025-11-13 | Gilead Sciences, Inc. | Combination therapies |
| WO2025240242A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025245489A1 (en) | 2024-05-24 | 2025-11-27 | Bristol-Myers Squibb Company | Treatment of tumors in subjects having fgl-1 positive samples |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU75628A1 (enExample) | 1976-08-19 | 1978-04-13 | ||
| CH654286A5 (de) * | 1981-11-04 | 1986-02-14 | Ciba Geigy Ag | Verfahren zur pd-katalysierten arylierung von olefinen mit arylhalogeniden. |
| US6410690B1 (en) | 1995-06-07 | 2002-06-25 | Medarex, Inc. | Therapeutic compounds comprised of anti-Fc receptor antibodies |
| US5811097A (en) | 1995-07-25 | 1998-09-22 | The Regents Of The University Of California | Blockade of T lymphocyte down-regulation associated with CTLA-4 signaling |
| US5977117A (en) | 1996-01-05 | 1999-11-02 | Texas Biotechnology Corporation | Substituted phenyl compounds and derivatives thereof that modulate the activity of endothelin |
| US5922845A (en) | 1996-07-11 | 1999-07-13 | Medarex, Inc. | Therapeutic multispecific compounds comprised of anti-Fcα receptor antibodies |
| JPWO2004007439A1 (ja) | 2002-07-10 | 2005-11-10 | 住友製薬株式会社 | ビアリール誘導体 |
| EP1603858A2 (en) | 2003-03-11 | 2005-12-14 | NeuroSearch A/S | Kcnq channel modulating compounds and their pharmaceutical use |
| JP2005179281A (ja) | 2003-12-19 | 2005-07-07 | Sumitomo Pharmaceut Co Ltd | ビフェニル化合物 |
| WO2005080367A1 (en) | 2004-02-12 | 2005-09-01 | Pharmagene Laboratories Limited | Ep2 receptor agonists |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| EP1951701A2 (en) | 2005-08-09 | 2008-08-06 | Asterand Uk Limited | Ep2 receptor agonists |
| TW200815377A (en) | 2006-04-24 | 2008-04-01 | Astellas Pharma Inc | Oxadiazolidinedione compound |
| JP2010524932A (ja) | 2007-04-16 | 2010-07-22 | アムジエン・インコーポレーテツド | 置換ビフェニルフェノキシ−、チオフェニル−及びアミノフェニルプロパン酸gpr40調節物質 |
| TW200932219A (en) * | 2007-10-24 | 2009-08-01 | Astellas Pharma Inc | Oxadiazolidinedione compound |
| TWI444467B (zh) * | 2010-05-27 | 2014-07-11 | Angus Chemical | 用於液體碳氫化合物及其他燃料與油之標記物化合物 |
| AU2014315457B2 (en) * | 2013-09-04 | 2018-05-10 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| US9850225B2 (en) * | 2014-04-14 | 2017-12-26 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| JP6876632B2 (ja) * | 2015-06-29 | 2021-05-26 | バンダービルト・ユニバーシティVanderbilt University | 手術中のシトルリン静脈内投与 |
| US10745382B2 (en) | 2015-10-15 | 2020-08-18 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| AU2017292758A1 (en) | 2016-07-08 | 2019-02-21 | Bristol-Myers Squibb Company | 1,3-dihydroxy-phenyl derivatives useful as immunomodulators |
| EP3493804A1 (en) * | 2016-08-03 | 2019-06-12 | Arising International, Inc. | Symmetric or semi-symmetric compounds useful as immunomodulators |
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| EP3507284A1 (en) | 2019-07-10 |
| US20180057455A1 (en) | 2018-03-01 |
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