AU2013218072B2 - Piperidino-pyrimidine derivatives for the treatment of viral infections - Google Patents
Piperidino-pyrimidine derivatives for the treatment of viral infections Download PDFInfo
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- AU2013218072B2 AU2013218072B2 AU2013218072A AU2013218072A AU2013218072B2 AU 2013218072 B2 AU2013218072 B2 AU 2013218072B2 AU 2013218072 A AU2013218072 A AU 2013218072A AU 2013218072 A AU2013218072 A AU 2013218072A AU 2013218072 B2 AU2013218072 B2 AU 2013218072B2
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- pharmaceutically acceptable
- 6alkyl
- heterocycle
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Classifications
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- A—HUMAN NECESSITIES
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Families Citing this family (165)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI3590928T1 (sl) | 2011-04-08 | 2021-10-29 | Janssen Sciences Ireland Unlimited Co | Derivati pirimidina za zdravljenje virusnih okužb |
| BR112014011162A2 (pt) | 2011-11-09 | 2017-05-09 | Janssen R&D Ireland | derivados purínicos para o tratamento de infecções virais |
| DK2812331T3 (en) | 2012-02-08 | 2019-04-08 | Janssen Sciences Ireland Unlimited Co | PIPERIDINOPYRIMIDINE DERIVATIVES FOR TREATING VIRUS INFECTIONS |
| WO2014009509A1 (en) | 2012-07-13 | 2014-01-16 | Janssen R&D Ireland | Macrocyclic purines for the treatment of viral infections |
| PT2906563T (pt) | 2012-10-10 | 2018-05-23 | Janssen Sciences Ireland Uc | Derivados de pirrolo[3,2-d]pirimidina para o tratamento de infeções virais e outras doenças |
| NZ748345A (en) | 2012-11-16 | 2020-04-24 | Janssen Sciences Ireland Uc | Heterocyclic substituted 2-amino-quinazoline derivatives for the treatment of viral infections |
| EA035174B1 (ru) | 2013-02-21 | 2020-05-12 | Янссен Сайенсиз Айрлэнд Юси | Производные 2-аминопиримидина в качестве модуляторов толл-подобных рецепторов tlr7 и/или tlr8 |
| ES2625456T3 (es) | 2013-03-29 | 2017-07-19 | Janssen Sciences Ireland Uc | Desazapurinonas macrocíclicas para el tratamiento de infecciones víricas |
| AU2014270418B2 (en) | 2013-05-24 | 2017-11-30 | Janssen Sciences Ireland Uc | Pyridone derivatives for the treatment of viral infections and further diseases |
| KR102311234B1 (ko) | 2013-06-27 | 2021-10-12 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 바이러스 감염 및 기타 질환의 치료를 위한 피롤로[3,2-d]피리미딘 유도체 |
| SG11201510736PA (en) | 2013-07-30 | 2016-02-26 | Janssen Sciences Ireland Uc | THIENO[3,2-d]PYRIMIDINES DERIVATIVES FOR THE TREATMENT OF VIRAL INFECTIONS |
| RS56787B1 (sr) | 2015-03-04 | 2018-04-30 | Gilead Sciences Inc | Toll-like receptor koji modulira jedinjenja 4,6-diamino-pirido[3,2-d]pirimidina |
| EP3341373A1 (en) | 2015-08-26 | 2018-07-04 | Gilead Sciences, Inc. | Deuterated toll-like receptor modulators |
| CA2997955A1 (en) | 2015-09-15 | 2017-03-23 | Gilead Sciences, Inc. | Modulators of toll-like receptors for the treatment of hiv |
| AU2016370591C1 (en) | 2015-12-15 | 2020-09-03 | Gilead Sciences, Inc. | Human immunodeficiency virus neutralizing antibodies |
| BR102017010009A2 (pt) | 2016-05-27 | 2017-12-12 | Gilead Sciences, Inc. | Compounds for the treatment of hepatitis b virus infection |
| KR102202984B1 (ko) | 2016-05-27 | 2021-01-13 | 길리애드 사이언시즈, 인코포레이티드 | Ns5a, ns5b 또는 ns3 억제제를 사용하여 b형 간염 바이러스 감염을 치료하는 방법 |
| JP7171444B2 (ja) * | 2016-07-01 | 2022-11-15 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | ウイルス感染治療用のジヒドロピラノピリミジン |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| US10370342B2 (en) * | 2016-09-02 | 2019-08-06 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| CR20190119A (es) | 2016-09-09 | 2019-06-03 | Novartis Ag | Compuestos y composiciones como inhibidores de los receptores endosomales tipo peaje |
| SG10202010317VA (en) | 2016-09-29 | 2020-11-27 | Janssen Sciences Ireland Unlimited Co | Pyrimidine prodrugs for the treatment of viral infections and further diseases |
| CN117402852A (zh) | 2016-10-14 | 2024-01-16 | 精密生物科学公司 | 对乙肝病毒基因组中的识别序列特异性的工程化大范围核酸酶 |
| TWI784370B (zh) | 2017-01-31 | 2022-11-21 | 美商基利科學股份有限公司 | 替諾福韋埃拉酚胺(tenofovir alafenamide)之晶型 |
| JOP20180008A1 (ar) | 2017-02-02 | 2019-01-30 | Gilead Sciences Inc | مركبات لعلاج إصابة بعدوى فيروس الالتهاب الكبدي b |
| JOP20180040A1 (ar) | 2017-04-20 | 2019-01-30 | Gilead Sciences Inc | مثبطات pd-1/pd-l1 |
| AR112412A1 (es) | 2017-08-17 | 2019-10-23 | Gilead Sciences Inc | Formas de sal de colina de un inhibidor de la cápside del vih |
| TW202024061A (zh) | 2017-08-17 | 2020-07-01 | 美商基利科學股份有限公司 | Hiv蛋白質膜抑制劑之固體形式 |
| CN111051305A (zh) | 2017-08-22 | 2020-04-21 | 吉利德科学公司 | 治疗性杂环化合物 |
| TW201915000A (zh) * | 2017-09-22 | 2019-04-16 | 大陸商江蘇恆瑞醫藥股份有限公司 | 稠合雜芳基衍生物、其製備方法及其在醫藥上的應用 |
| WO2019084060A1 (en) | 2017-10-24 | 2019-05-02 | Silverback Therapeutics, Inc. | CONJUGATES AND METHODS OF USE FOR THE SELECTIVE DELIVERY OF IMMUNOMODULATORY AGENTS |
| WO2019118884A1 (en) | 2017-12-15 | 2019-06-20 | Silverback Therapeutics, Inc. | Antibody construct-drug conjugate for the treatment of hepatitis |
| CN111511754B (zh) | 2017-12-20 | 2023-09-12 | 捷克共和国有机化学与生物化学研究所 | 活化sting转接蛋白的具有膦酸酯键的2’3’环状二核苷酸 |
| AU2018392213B2 (en) | 2017-12-20 | 2021-03-04 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3' cyclic dinucleotides with phosphonate bond activating the STING adaptor protein |
| UA126458C2 (uk) | 2018-02-13 | 2022-10-05 | Гіліад Сайєнсіз, Інк. | Інгібітори pd-1/pd-l1 |
| JP7083398B2 (ja) | 2018-02-15 | 2022-06-10 | ギリアード サイエンシーズ， インコーポレイテッド | ピリジン誘導体およびｈｉｖ感染を処置するためのその使用 |
| EP3752496B1 (en) | 2018-02-16 | 2023-07-05 | Gilead Sciences, Inc. | Methods and intermediates for preparing a therapeutic compound useful in the treatment of retroviridae viral infection |
| TWI772370B (zh) * | 2018-02-26 | 2022-08-01 | 瑞士商諾華公司 | 作為胞內體類鐸（toll-like）受體抑制劑之化合物及組合物 |
| ES2962605T3 (es) | 2018-02-26 | 2024-03-20 | Gilead Sciences Inc | Compuestos de pirrolizina sustituidos como inhibidores de la replicación del VHB |
| TW201945003A (zh) | 2018-03-01 | 2019-12-01 | 愛爾蘭商健生科學愛爾蘭無限公司 | ２，４－二胺基喹唑啉衍生物及其醫學用途 |
| WO2019195181A1 (en) | 2018-04-05 | 2019-10-10 | Gilead Sciences, Inc. | Antibodies and fragments thereof that bind hepatitis b virus protein x |
| TWI833744B (zh) | 2018-04-06 | 2024-03-01 | 捷克科學院有機化學與生物化學研究所 | 3'3'-環二核苷酸 |
| TW202005654A (zh) | 2018-04-06 | 2020-02-01 | 捷克科學院有機化學與生物化學研究所 | ２，２，─環二核苷酸 |
| TWI818007B (zh) | 2018-04-06 | 2023-10-11 | 捷克科學院有機化學與生物化學研究所 | 2'3'-環二核苷酸 |
| US11142750B2 (en) | 2018-04-12 | 2021-10-12 | Precision Biosciences, Inc. | Optimized engineered meganucleases having specificity for a recognition sequence in the Hepatitis B virus genome |
| US10899735B2 (en) | 2018-04-19 | 2021-01-26 | Gilead Sciences, Inc. | PD-1/PD-L1 inhibitors |
| TW202014193A (zh) | 2018-05-03 | 2020-04-16 | 捷克科學院有機化學與生物化學研究所 | 包含碳環核苷酸之2’3’－環二核苷酸 |
| CA3097312A1 (en) | 2018-05-18 | 2019-11-21 | Novartis Ag | Crystalline forms of a tlr7/tlr8 inhibitor |
| LT4257600T (lt) | 2018-07-03 | 2025-06-10 | Gilead Sciences, Inc. | Antikūnai, nukreipti į gp120, ir jų panaudojimo būdai |
| US11098027B2 (en) | 2018-07-06 | 2021-08-24 | Gilead Sciences, Inc. | Therapeutic heterocyclic compounds |
| CN112384283B (zh) | 2018-07-06 | 2023-08-15 | 吉利德科学公司 | 治疗性的杂环化合物 |
| EP3820572B1 (en) | 2018-07-13 | 2023-08-16 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| AU2019307500B2 (en) | 2018-07-16 | 2022-09-29 | Gilead Sciences, Inc. | Capsid inhibitors for the treatment of HIV |
| 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 |
| KR20210081332A (ko) | 2018-09-12 | 2021-07-01 | 실버백 테라퓨틱스, 인크. | 면역 자극성 접합체를 사용한 질환의 치료를 위한 조성물 |
| US11179397B2 (en) | 2018-10-03 | 2021-11-23 | Gilead Sciences, Inc. | Imidazopyrimidine derivatives |
| AU2019366355B2 (en) | 2018-10-24 | 2022-10-13 | Gilead Sciences, Inc. | PD-1/PD-L1 inhibitors |
| BR112021008255A2 (pt) | 2018-10-31 | 2021-08-03 | Gilead Sciences, Inc. | compostos de 6-azabenzimidazol substituídos como inibidores de hpk1 |
| JP7273172B2 (ja) | 2018-10-31 | 2023-05-12 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｐｋ１阻害活性を有する置換６－アザベンゾイミダゾール化合物 |
| JP7287708B2 (ja) | 2019-02-08 | 2023-06-06 | プロジェニア インコーポレイテッド | Ｔｏｌｌ－ｌｉｋｅ受容体７または８アゴニストとコレステロールの結合体およびその用途 |
| WO2020176505A1 (en) | 2019-02-25 | 2020-09-03 | Gilead Sciences, Inc. | Protein kinase c agonists |
| WO2020176510A1 (en) | 2019-02-25 | 2020-09-03 | Gilead Sciences, Inc. | Protein kinase c agonists |
| US11766447B2 (en) | 2019-03-07 | 2023-09-26 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3′3′-cyclic dinucleotide analogue comprising a cyclopentanyl modified nucleotide as sting modulator |
| US12318403B2 (en) | 2019-03-07 | 2025-06-03 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2′3′-cyclic dinucleotides and prodrugs thereof |
| WO2020178770A1 (en) | 2019-03-07 | 2020-09-10 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotides and prodrugs thereof |
| CN113874079B (zh) | 2019-03-22 | 2024-11-08 | 吉利德科学公司 | 桥连三环氨基甲酰基吡啶酮化合物及其药学用途 |
| 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 |
| TWI762925B (zh) | 2019-05-21 | 2022-05-01 | 美商基利科學股份有限公司 | 鑑別對使用gp120 v3聚醣導向之抗體的治療敏感之hiv病患的方法 |
| EP3972695A1 (en) | 2019-05-23 | 2022-03-30 | Gilead Sciences, Inc. | Substituted exo-methylene-oxindoles which are hpk1/map4k1 inhibitors |
| US20220305115A1 (en) | 2019-06-18 | 2022-09-29 | Janssen Sciences Ireland Unlimited Company | Combination of hepatitis b virus (hbv) vaccines and pyridopyrimidine derivatives |
| BR112021025699A2 (pt) | 2019-06-19 | 2022-03-03 | Silverback Therapeutics Inc | Anticorpos anti-mesotelina e imunoconjugados dos mesmos |
| MX2021015452A (es) | 2019-06-25 | 2022-02-11 | Gilead Sciences Inc | Proteinas de fusion flt3l-fc y metodos de uso. |
| TWI879779B (zh) | 2019-06-28 | 2025-04-11 | 美商基利科學股份有限公司 | 類鐸受體調節劑化合物的製備方法 |
| CA3145791A1 (en) | 2019-07-16 | 2021-01-21 | Gilead Sciences, Inc. | Hiv vaccines and methods of making and using |
| WO2021011891A1 (en) | 2019-07-18 | 2021-01-21 | Gilead Sciences, Inc. | Long-acting formulations of tenofovir alafenamide |
| US20220296619A1 (en) | 2019-08-19 | 2022-09-22 | Gilead Sciences, Inc. | Pharmaceutical formulations of tenofovir alafenamide |
| IL315295A (en) | 2019-09-30 | 2024-10-01 | Gilead Sciences Inc | Hbv vaccines and methods treating hbv |
| WO2021067644A1 (en) | 2019-10-01 | 2021-04-08 | Silverback Therapeutics, Inc. | Combination therapy with immune stimulatory conjugates |
| CA3153501A1 (en) | 2019-10-18 | 2021-04-22 | Forty Seven, Inc. | Combination therapies for treating myelodysplastic syndromes and acute myeloid leukemia |
| WO2021087064A1 (en) | 2019-10-31 | 2021-05-06 | Forty Seven, Inc. | Anti-cd47 and anti-cd20 based treatment of blood cancer |
| TWI778443B (zh) | 2019-11-12 | 2022-09-21 | 美商基利科學股份有限公司 | Mcl1抑制劑 |
| KR20220106165A (ko) | 2019-11-26 | 2022-07-28 | 길리애드 사이언시즈, 인코포레이티드 | Hiv의 예방을 위한 캡시드 억제제 |
| WO2021113765A1 (en) | 2019-12-06 | 2021-06-10 | Precision Biosciences, Inc. | Optimized engineered meganucleases having specificity for a recognition sequence in the hepatitis b virus genome |
| EP4445902A3 (en) | 2019-12-24 | 2024-12-18 | Carna Biosciences, Inc. | Diacylglycerol kinase modulating compounds |
| MX2022009947A (es) | 2020-02-14 | 2022-11-07 | Jounce Therapeutics Inc | Anticuerpos y proteinas de fusion que se unen a ccr8 y usos de estos. |
| JP7735291B2 (ja) | 2020-02-21 | 2025-09-08 | エーアールエス ファーマシューティカルズ、インコーポレイテッド | ネクチン－４抗体コンジュゲートおよびその使用 |
| CA3170551A1 (en) | 2020-03-02 | 2021-09-10 | Yong Taik Lim | Live-pathogen-mimetic nanoparticles based on pathogen cell wall skeleton, and production method thereof |
| JP2023518433A (ja) | 2020-03-20 | 2023-05-01 | ギリアード サイエンシーズ， インコーポレイテッド | ４’－ｃ－置換－２－ハロ－２’－デオキシアデノシンヌクレオシドのプロドラッグ並びにその製造法及び使用法 |
| CA3181922A1 (en) | 2020-05-01 | 2021-11-04 | Gilead Sciences, Inc. | Cd73 inhibiting 2,4-dioxopyrimidine compounds |
| BR112022022338A2 (pt) | 2020-05-04 | 2023-01-10 | Amgen Inc | Compostos heterocíclicos como receptor desencadeador expresso em agonistas de células mieloides 2 e métodos de uso |
| TW202208355A (zh) | 2020-05-04 | 2022-03-01 | 美商安進公司 | 作為骨髓細胞觸發受體2促效劑之雜環化合物及使用方法 |
| WO2021236944A1 (en) | 2020-05-21 | 2021-11-25 | Gilead Sciences, Inc. | Pharmaceutical compositions comprising bictegravir |
| KR20230027275A (ko) | 2020-06-25 | 2023-02-27 | 길리애드 사이언시즈, 인코포레이티드 | Hiv 치료용 캡시드 저해제 |
| CA3183993A1 (en) | 2020-07-01 | 2022-01-06 | Peter R. Baum | Anti-asgr1 antibody conjugates and uses thereof |
| EP4194010A4 (en) | 2020-08-04 | 2025-03-26 | Progeneer Inc. | Conjugate of a functional drug and a toll-like receptor 7 or 8 agonist with a temporarily inactivated drug site, and use thereof |
| WO2022031011A1 (ko) | 2020-08-04 | 2022-02-10 | 성균관대학교산학협력단 | 동력학적으로 작용하는 아주번트 앙상블 |
| EP4194006A4 (en) | 2020-08-04 | 2024-12-04 | Progeneer Inc. | mRNA VACCINE WITH AN ADJUVANT CAPABLE OF KINETIC CONTROL |
| EP4192474B1 (en) | 2020-08-07 | 2025-09-10 | Gilead Sciences, Inc. | Prodrugs of phosphonamide nucleotide analogues and their pharmaceutical use |
| TWI815194B (zh) | 2020-10-22 | 2023-09-11 | 美商基利科學股份有限公司 | 介白素2-Fc融合蛋白及使用方法 |
| CN116437958A (zh) | 2020-11-11 | 2023-07-14 | 吉利德科学公司 | 鉴定对采用gp120 CD4结合位点导向的抗体的疗法敏感的HIV患者的方法 |
| CA3215049A1 (en) | 2021-04-10 | 2022-10-13 | Baiteng ZHAO | Folr1 binding agents, conjugates thereof and methods of using the same |
| TW202302145A (zh) | 2021-04-14 | 2023-01-16 | 美商基利科學股份有限公司 | ＣＤ４７／ＳＩＲＰα結合及ＮＥＤＤ８活化酶Ｅ１調節次單元之共抑制以用於治療癌症 |
| AU2022262644A1 (en) | 2021-04-23 | 2023-11-09 | Genmab A/S | Anti-cd70 antibodies, conjugates thereof and methods of using the same |
| TW202310852A (zh) | 2021-05-13 | 2023-03-16 | 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 |
| TW202313094A (zh) | 2021-05-18 | 2023-04-01 | 美商基利科學股份有限公司 | 使用ＦＬＴ３Ｌ—Ｆｃ融合蛋白之方法 |
| KR20240023629A (ko) | 2021-06-23 | 2024-02-22 | 길리애드 사이언시즈, 인코포레이티드 | 디아실글리세롤 키나제 조절 화합물 |
| CR20230585A (es) | 2021-06-23 | 2024-02-19 | Gilead Sciences Inc | Compuestos Moduladores de Diacilglicerol Quinasa. |
| EP4359411A1 (en) | 2021-06-23 | 2024-05-01 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| KR20240005901A (ko) | 2021-06-23 | 2024-01-12 | 길리애드 사이언시즈, 인코포레이티드 | 디아실글리세롤 키나제 조절 화합물 |
| TW202320857A (zh) | 2021-07-06 | 2023-06-01 | 美商普方生物製藥美國公司 | 連接子、藥物連接子及其結合物及其使用方法 |
| TWI857377B (zh) | 2021-10-28 | 2024-10-01 | 美商基利科學股份有限公司 | 嗒-3(2h)-酮衍生物 |
| JP7787991B2 (ja) | 2021-10-29 | 2025-12-17 | ギリアード サイエンシーズ， インコーポレイテッド | Ｃｄ７３化合物 |
| EP4440700A1 (en) | 2021-12-03 | 2024-10-09 | Gilead Sciences, Inc. | Therapeutic compounds for hiv virus infection |
| KR20240113832A (ko) | 2021-12-03 | 2024-07-23 | 길리애드 사이언시즈, 인코포레이티드 | Hiv 바이러스 감염 치료용 화합물 |
| PT4445900T (pt) | 2021-12-03 | 2025-08-13 | Gilead Sciences Inc | Compostos terapêuticos para a infecção pelo vírus do hiv |
| WO2023107956A1 (en) | 2021-12-08 | 2023-06-15 | Dragonfly Therapeutics, Inc. | Proteins binding nkg2d, cd16 and 5t4 |
| US20230220106A1 (en) | 2021-12-08 | 2023-07-13 | Dragonfly Therapeutics, Inc. | Antibodies targeting 5t4 and uses thereof |
| CN118382625A (zh) * | 2021-12-08 | 2024-07-23 | 上海维申医药有限公司 | 作为TLR7/8激动剂的吡啶[4,3-d]嘧啶类化合物 |
| CN118488946A (zh) | 2021-12-22 | 2024-08-13 | 吉利德科学公司 | Ikaros锌指家族降解剂及其用途 |
| CA3237577A1 (en) | 2021-12-22 | 2023-06-29 | Gilead Sciences, Inc. | Ikaros zinc finger family degraders and uses thereof |
| TW202340168A (zh) | 2022-01-28 | 2023-10-16 | 美商基利科學股份有限公司 | Ｐａｒｐ７抑制劑 |
| US12358887B2 (en) | 2022-03-17 | 2025-07-15 | Gilead Sciences, Inc. | IKAROS Zinc Finger Family degraders and uses thereof |
| US20230355796A1 (en) | 2022-03-24 | 2023-11-09 | Gilead Sciences, Inc. | Combination therapy for treating trop-2 expressing cancers |
| TWI876305B (zh) | 2022-04-05 | 2025-03-11 | 美商基利科學股份有限公司 | 用於治療結腸直腸癌之組合療法 |
| TWI843506B (zh) | 2022-04-06 | 2024-05-21 | 美商基利科學股份有限公司 | 橋聯三環胺甲醯基吡啶酮化合物及其用途 |
| JP2025513258A (ja) | 2022-04-21 | 2025-04-24 | ギリアード サイエンシーズ， インコーポレイテッド | Ｋｒａ ｇ１２ｄ調節化合物 |
| TWI867601B (zh) | 2022-07-01 | 2024-12-21 | 美商基利科學股份有限公司 | 可用於ｈｉｖ病毒感染之疾病預防性或治療性治療的治療性化合物 |
| IL317958A (en) | 2022-07-01 | 2025-02-01 | Gilead Sciences Inc | CD73 compounds |
| JP2025523043A (ja) | 2022-07-12 | 2025-07-17 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｉｖ免疫原性ポリペプチド及びワクチン、並びにその使用 |
| CN119768183A (zh) | 2022-08-26 | 2025-04-04 | 吉利德科学公司 | 用于广泛中和抗体的给药和安排方案 |
| WO2024064668A1 (en) | 2022-09-21 | 2024-03-28 | Gilead Sciences, Inc. | FOCAL IONIZING RADIATION AND CD47/SIRPα DISRUPTION ANTICANCER COMBINATION THERAPY |
| WO2024076915A1 (en) | 2022-10-04 | 2024-04-11 | Gilead Sciences, Inc. | 4'-thionucleoside analogues and their pharmaceutical use |
| EP4638436A1 (en) | 2022-12-22 | 2025-10-29 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| CN120882725A (zh) | 2023-04-11 | 2025-10-31 | 吉利德科学公司 | Kras调节化合物 |
| TW202444363A (zh) | 2023-04-19 | 2024-11-16 | 美商基利科學股份有限公司 | 殼體抑制劑之給藥方案 |
| AU2024259556A1 (en) | 2023-04-21 | 2025-10-23 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| US20250011352A1 (en) | 2023-05-31 | 2025-01-09 | Gilead Sciences, Inc. | Solid forms |
| US20250042926A1 (en) | 2023-05-31 | 2025-02-06 | Gilead Sciences, Inc. | Therapeutic compounds for hiv |
| US20250042922A1 (en) | 2023-06-30 | 2025-02-06 | Gilead Sciences, Inc. | Kras modulating compounds |
| US20250100998A1 (en) | 2023-07-26 | 2025-03-27 | Gilead Sciences, Inc. | Parp7 inhibitors |
| WO2025024663A1 (en) | 2023-07-26 | 2025-01-30 | Gilead Sciences, Inc. | Parp7 inhibitors |
| WO2025029247A1 (en) | 2023-07-28 | 2025-02-06 | Gilead Sciences, Inc. | Weekly regimen of lenacapavir for the treatment and prevention of hiv |
| WO2025042394A1 (en) | 2023-08-23 | 2025-02-27 | Gilead Sciences, Inc. | Dosing regimen of hiv capsid inhibitor |
| WO2025054347A1 (en) | 2023-09-08 | 2025-03-13 | Gilead Sciences, Inc. | Kras g12d modulating compounds |
| US20250109147A1 (en) | 2023-09-08 | 2025-04-03 | Gilead Sciences, Inc. | Kras g12d modulating compounds |
| WO2025072406A1 (en) | 2023-09-26 | 2025-04-03 | Profoundbio Us Co. | Ptk7 binding agents, conjugates thereof and methods of using the same |
| US20250127801A1 (en) | 2023-10-11 | 2025-04-24 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| US20250120989A1 (en) | 2023-10-11 | 2025-04-17 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| TW202530227A (zh) | 2023-10-11 | 2025-08-01 | 美商基利科學股份有限公司 | 橋聯三環胺甲醯基吡啶酮化合物及其用途 |
| US20250154172A1 (en) | 2023-11-03 | 2025-05-15 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
| WO2025137245A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Solid forms of hiv integrase inhibitors |
| WO2025149661A1 (en) | 2024-01-10 | 2025-07-17 | Genmab A/S | Slitrk6 binding agents, conjugates thereof and methods of using the same |
| US20250381289A1 (en) | 2024-02-29 | 2025-12-18 | Genmab A/S | Egfr and c-met bispecific binding agents, conjugates thereof and methods of using the same |
| WO2025184447A1 (en) | 2024-03-01 | 2025-09-04 | Gilead Sciences, Inc. | Pharmaceutical compositions comprising hiv integrase inhibitors |
| WO2025184609A1 (en) | 2024-03-01 | 2025-09-04 | Gilead Sciences, Inc. | Antiviral compounds |
| US20250289822A1 (en) | 2024-03-01 | 2025-09-18 | Gilead Sciences, Inc. | Solid forms of hiv integrase inhibitors |
| US20250345389A1 (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 |
| US20250345390A1 (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 |
| WO2025245003A1 (en) | 2024-05-21 | 2025-11-27 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| WO2025260028A1 (en) | 2024-06-14 | 2025-12-18 | Gilead Sciences, Inc. | Pharmaceutical compositions comprising hiv integrase inhibitors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009067081A1 (en) * | 2007-11-22 | 2009-05-28 | Astrazeneca Ab | Pyrimidine derivatives for the treatment of asthma, copd, allergic rhinitis, allergic conjunctivitis, atopic dermatitis, cancer, hepatitis b, hepatitis c, hiv, hpv, bacterial infections and dermatosis |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ329798A (en) | 1996-07-03 | 1999-04-29 | Japan Energy Corp | Purine derivatives their tautomers and salts thereof and interferon secretion inducers, antiviral agents and anticancer drugs containing the same |
| ATE247654T1 (de) | 1997-11-28 | 2003-09-15 | Sumitomo Pharma | Neue heterozyklische verbindungen |
| WO2000012487A1 (en) * | 1998-08-27 | 2000-03-09 | Sumitomo Pharmaceuticals Co., Ltd. | Pyrimidine derivatives |
| WO2002088079A2 (en) * | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| WO2003104230A1 (ja) * | 2002-06-07 | 2003-12-18 | 協和醱酵工業株式会社 | 二環性ピリミジン誘導体 |
| US7498409B2 (en) | 2005-03-24 | 2009-03-03 | Schering Corporation | Screening assay for TLR7, TLR8 and TLR9 agonists and antagonists |
| JP2008540396A (ja) | 2005-05-04 | 2008-11-20 | ファイザー・リミテッド | 癌およびｃ型肝炎などのウイルス感染を治療するためのトール様受容体調節薬としての２−アミド−６−アミノ−８−オキソプリン誘導体 |
| BRPI0907907A2 (pt) | 2008-02-07 | 2015-07-28 | Univ California | Método para inibir ou trata câncer de bexiga superficial em um mamífero, e, uso de um agonista de tlr 7 |
| CN102482233A (zh) * | 2009-05-21 | 2012-05-30 | 阿斯利康(瑞典)有限公司 | 新颖的嘧啶衍生物和它们在治疗癌症和其它疾病中的用途 |
| US8637525B2 (en) * | 2009-07-31 | 2014-01-28 | Bristol-Myers Squibb Company | Compounds for the reduction of beta-amyloid production |
| TWI468402B (zh) * | 2009-07-31 | 2015-01-11 | 必治妥美雅史谷比公司 | 降低β－類澱粉生成之化合物 |
| JP2013032290A (ja) * | 2009-11-20 | 2013-02-14 | Dainippon Sumitomo Pharma Co Ltd | 新規縮合ピリミジン誘導体 |
| DK2812331T3 (en) * | 2012-02-08 | 2019-04-08 | Janssen Sciences Ireland Unlimited Co | PIPERIDINOPYRIMIDINE DERIVATIVES FOR TREATING VIRUS INFECTIONS |
-
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- 2013-02-07 DK DK13703055.7T patent/DK2812331T3/en active
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009067081A1 (en) * | 2007-11-22 | 2009-05-28 | Astrazeneca Ab | Pyrimidine derivatives for the treatment of asthma, copd, allergic rhinitis, allergic conjunctivitis, atopic dermatitis, cancer, hepatitis b, hepatitis c, hiv, hpv, bacterial infections and dermatosis |
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