TWI455940B - 新穎1,2,3,4-四氫嘧啶并[1,2-a]嘧啶-4-酮衍生物、其製備及其醫藥用途 - Google Patents
新穎1,2,3,4-四氫嘧啶并[1,2-a]嘧啶-4-酮衍生物、其製備及其醫藥用途 Download PDFInfo
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- pyrimidin
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- morpholin
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Claims (33)
- 一種式(I)產物, 其中:R1表示-L-芳基或-L-雜芳基,其中L表示:單鍵,或含有1至6個碳原子且視情況經羥基取代之直鏈或分支鏈烷基,或CO或-CO-烷基-,或L'-X基團,其中L'表示含有1至6個碳原子之直鏈或分支鏈烷基,且X為氧原子或硫原子;該等芳基及雜芳基視情況經一或多個選自以下之可相同或不同的基團取代:鹵素原子,及羥基、CN、硝基、-COOH、-COO烷基、-NRxRy、-CONRxRy、-NRxCORy、-NRxCO2 Rz、-CORy、烷氧基、苯氧基、烷硫基、烷基、環烷基及雜環烷基;該等烷氧基、苯氧基、烷硫基、烷基及雜環烷基本身視情況經一或多個選自鹵素原子及NRvRw之可相同或不同的基團取代;該等雜環烷基及雜芳基可另外含有側氧基(oxo); R2表示氫原子或烷基;R3表示氫原子或視情況經一或多個鹵素原子取代之烷基;R4表示氫原子或鹵素原子;NRxRy如下:Rx表示氫原子或烷基,且Ry表示氫原子或視情況經一或多個選自羥基、烷氧基、NRvRw及雜環烷基之可相同或不同的基團取代之環烷基或烷基;或Rx及Ry與其連接之氮原子一起形成含有3至10個環成員且視情況含有一或多個選自O、S、NH及N-烷基之其他雜原子的環狀基團,此環狀基團視情況經取代;NRvRw如下:Rv表示氫原子或烷基,且Rw表示氫原子或視情況經一或多個選自羥基、烷氧基及雜環烷基之可相同或不同的基團取代之環烷基或烷基;或Rv及Rw與其連接之氮原子一起形成含有3至10個環成員且視情況含有一或多個選自O、S、NH及N-烷基之其他雜原子的環狀基團,此環狀基團視情況經取代;Rx及Ry或Rv及Rw可分別與其連接之氮原子一起形成之該等環狀基團視情況經一或多個選自以下之可相同或不同的基團取代:鹵素原子,及烷基、羥基、側氧基、烷氧基、NH2 、NH烷基及N(烷基)2 ;Rz表示除氫之外的Ry之涵義;該等-NRxCORy、-CORy及NRxCO2 Rz基團中之Rx、Ry及Rz係選自以上針對Rx、Ry及Rz所指示之含義;以上所有該等烷基、烷氧基及烷硫基均為直鏈或分支 鏈基團且含有1至6個碳原子,該等式(I)產物為所有可能之外消旋、對映異構體及非對映異構體形式,以及該等式(I)產物與無機酸及有機酸或與無機鹼及有機鹼形成之加成鹽。
- 如請求項1之式(I)產物,其中:R1表示-L-苯基或-L-雜芳基,其中L表示:單鍵,或含有1至6個碳原子且視情況經羥基取代之直鏈或分支鏈烷基,或CO或-CO-烷基-,或L'-X基團,其中L'表示含有1至6個碳原子之直鏈或分支鏈烷基,且X為氧原子或硫原子;該等苯基及雜芳基視情況經一或多個選自鹵素原子及-NRxRy、烷氧基及烷基之可相同或不同的基團取代;該等烷氧基及烷基本身視情況經一或多個選自鹵素原子之基團取代;R2表示烷基;R3表示氫原子或視情況經一或多個鹵素原子取代之烷基;R4表示氫原子或氟原子;NRxRy如下:Rx表示氫原子或烷基,且Ry表示氫原子或烷基;或Rx及Ry與其連接之氮原子一起形成N-嗎啉基;以上所有該等烷基或烷氧基均為直鏈或分支鏈基團且 含有1至6個碳原子,該等式(I)產物為所有可能之外消旋、對映異構體及非對映異構體形式,以及該等式(I)產物與無機酸及有機酸或與無機鹼及有機鹼形成之加成鹽。
- 如請求項1及2中任一項之式(I)產物,其對應於以下各式:(8S)-9-[2-(4-甲氧基苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮9-[2-(4-甲氧基苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-9-(2-苯乙基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-苄基-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(2S)-2-羥基-2-苯乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(2R)-2-羥基-2-苯乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(2S)-2-羥基-2-(4-甲氧基苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-9-[(1R)-1-苯乙基]-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[1-(4-甲氧基苯基)乙基]-2-(嗎啉-4-基)-8-(三氟 甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(1S)-1-(4-溴苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(1R)-1-(4-溴苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-9-苯基-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(4-氟苯基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(3-氟苯基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(2-氟苯基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(1R)-1-(3-氟苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(4-氟苄基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-9-(苯基羰基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-9-(吡啶-3-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-9-(吡啶-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(4-甲基苯基)-2-(嗎啉-4-基)-8-(三氟甲基)- 6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(2-氯苄基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(3-氟苄基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[2-(2-甲氧基苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[2-(3-甲氧基苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(3-甲氧基苄基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(4-甲氧基苯基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(2-氟苯基)羰基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(3,5-二氟苄基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(2,4-二氟苄基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-9-(2,3,4-三氟苄基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(5-氯-1-苯并噻吩-3-基)甲基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(1R或1S)-1-(4-氟苯基)乙基]-2-(嗎啉-4-基)-8- (三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(1R或1S)-1-(4-氟苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(3-甲基苯基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(4-氯苯基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-8-(三氟甲基)-9-[4-(三氟甲基)苯基]-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(1R或1S)-1-(2-氟苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(1R或1S)-1-(2-氟苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[2-(3-氟苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-苄基-3-氟-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-(3,5-二氟苯基)-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(2,6-二氟苯基)羰基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[(2,4-二氟苯基)羰基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-2-(嗎啉-4-基)-9-(苯基乙醯基)-8-(三氟甲基)- 6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮(8S)-9-[2-(3-氯苯基)乙基]-2-(嗎啉-4-基)-8-(三氟甲基)-6,7,8,9-四氫-4H-嘧啶并[1,2-a]嘧啶-4-酮9-((R)-2-苯并[b]噻吩-2-基-2-羥乙基)-2-嗎啉-4-基-8-(S)-三氟甲基-6,7,8,9-四氫嘧啶并[1,2-a]嘧啶-4-酮9-[(S)-2-羥基-2-(3-羥基苯基)乙基]-2-嗎啉-4-基-8-(S)-三氟甲基-6,7,8,9-四氫嘧啶并[1,2-a]嘧啶-4-酮2-二甲胺基-N-{3-[(S)-1-羥基-2-((S)-8-嗎啉-4-基-6-側氧基-2-三氟甲基-3,4-二氫-2H,6H-嘧啶并[1,2-a]嘧啶-1-基)乙基]苯基}乙醯胺9-[(S)-2-羥基-2-(2-甲氧基苯基)乙基]-2-嗎啉-4-基-8-(S)-三氟甲基-6,7,8,9-四氫嘧啶并[1,2-a]嘧啶-4-酮9-[(S)-2-(4-氟-2-甲氧基苯基)-2-羥乙基]-2-嗎啉-4-基-8-(S)-三氟甲基-6,7,8,9-四氫嘧啶并[1,2-a]嘧啶-4-酮9-[(S)-2-(4-氯-2-甲氧基苯基)-2-羥乙基]-2-嗎啉-4-基-8-(S)-三氟甲基-6,7,8,9-四氫嘧啶并[1,2-a]嘧啶-4-酮9-[(S)-2-(2-氯-4-甲氧基苯基)-2-羥乙基]-2-嗎啉-4-基-8-(S)-三氟甲基-6,7,8,9-四氫嘧啶并[1,2-a]嘧啶-4-酮9-(2-羥基-3-苯丙基)-2-嗎啉-4-基-8-(S)-三氟甲基-6,7,8,9-四氫嘧啶并[1,2-a]嘧啶-4-酮9-[2-(4-羥基苯基)乙基]-2-嗎啉-4-基-8-(S)-三氟甲基-6,7,8,9-四氫嘧啶并[1,2-a]嘧啶-4-酮以及該等式(I)產物與無機酸及有機酸或與無機鹼及有機鹼形成之加成鹽。
- 一種製備如請求項1至3中任一項之式(I)產物之方法,其係根據如下文定義之流程1製備, 其中取代基R1、R2、R3及R4具有如請求項1及2中任一項所指示之含義,且其中R表示烷基,且X表示氯原子、溴原子或碘原子,或磺醯氧基。
- 一種製備如請求項1至3中任一項之式(I)產物之方法,其係根據如下文定義之流程2製備,流程2: 其中取代基R1、R2、R3及R4具有如請求項1及2中任一項所指示之含義,且X表示氯原子、溴原子或碘原子,或磺醯氧基。
- 如請求項1或2之式(I)產物,以及該式(I)產物與無機酸及有機酸或與無機鹼及有機鹼形成之醫藥學上可接受之加成鹽,其係用作藥劑。
- 如請求項3之式(I)產物,以及該式(I)產物與無機酸及有機酸或與無機鹼及有機鹼形成之醫藥學上可接受之加成鹽,其係用作藥劑。
- 一種醫藥組合物,其含有至少一種如請求項1至3中任一項之式(I)產物或該產物之醫藥學上可接受之鹽作為活性成份,及醫藥學上可接受之載劑。
- 一種如請求項1至3中任一項之式(I)產物之用途,其用於製備供治療癌症之藥劑。
- 如請求項9之用途,其中該藥劑係用於治療固體或液體腫瘤。
- 如請求項9或10之用途,其中該藥劑係用於治療對細胞毒性劑具有抗性之癌症。
- 如請求項9或10之用途,其中該藥劑係用於治療原發性腫瘤及/或轉移。
- 如請求項12之用途,其中該藥劑係用於治療胃癌、肝癌、腎癌、卵巢癌、結腸癌、***癌、子宮內膜癌及肺癌、神經膠母細胞瘤、甲狀腺癌、膀胱癌及乳癌、黑色素瘤、淋巴或骨髓造血腫瘤、肉瘤、腦癌、喉癌及淋巴系統癌、骨癌及胰腺癌、及錯構瘤。
- 一種如請求項1至3中任一項之式(I)產物之用途,其用於製備供癌症化學療法中用之藥劑。
- 一種如請求項1至3中任一項之式(I)產物之用途,其用於製備單獨或組合供癌症化學療法中用之藥劑。
- 如請求項1或2之式(I)產物,其用作AKT磷酸化抑制劑。
- 一種選自以下式C、D、E及J的合成中間物: 其中R1、R2、R3及R4具有如請求項1或2所指示之定義。
- 如請求項1或2之式(I)產物,其用於治療癌症。
- 如請求項1或2之式(I)產物,其用於治療固體或液體腫瘤。
- 如請求項1或2之式(I)產物,其用於治療對細胞毒性劑具有抗性之癌症。
- 如請求項1或2之式(I)產物,其用於治療原發性腫瘤及/或轉移。
- 如請求項21之式(I)產物,其用於治療胃癌、肝癌、腎癌、卵巢癌、結腸癌、***癌、子宮內膜癌及肺癌、神經膠母細胞瘤、甲狀腺癌、膀胱癌及乳癌、黑色素瘤、淋巴或骨髓造血腫瘤、肉瘤、腦癌、喉癌及淋巴系統癌、骨癌及胰腺癌、及錯構瘤。
- 如請求項1或2之式(I)產物,其用於癌症化學療法中。
- 如請求項1或2之式(I)產物,其單獨或組合用於癌症化學療法中。
- 如請求項1或2之式(I)產物,其用於預防或治療溶酶體病。
- 如請求項25之式(I)產物,其用於預防或治療第II型肝糖貯積症或龐培氏症(Pompe disease)。
- 一種如請求項1或2之式(I)產物之用途,其用於製備供預防或治療溶酶體病的藥劑。
- 如請求項27之用途,其用於製備供預防或治療第II型肝糖貯積症或龐培氏症的藥劑。
- 如請求項27之用途,其中該式(I)產物單獨或組合使用。
- 如請求項1或2之式(I)產物,其用於治療寄生蟲病。
- 如請求項30之產物,其用於治療瘧疾、昏睡病、恰加斯氏症(Chagas disease)或利什曼病(leishmaniasis)。
- 一種如請求項1或2之式(I)產物之用途,其用於製備供治療寄生蟲病的藥劑。
- 如請求項32之用途,其用於製備供治療瘧疾、昏睡病、恰加斯氏症或利什曼病的藥劑。
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FR0903237A FR2947551B1 (fr) | 2009-07-02 | 2009-07-02 | Nouveaux derives de 1,2,3,4-tetrahydro-pyrimido{1,2-a)pyrimidin-6-one, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de phosphorylation d'akt (pkb) |
US24109809P | 2009-09-10 | 2009-09-10 | |
FR0957069A FR2951174B1 (fr) | 2009-10-09 | 2009-10-09 | Nouveaux derives de 1,2,3,4-tetrahydro-pyrimido{1,2-a}pyrimidin-6-one, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de phosphorylation d'akt(pkb) |
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TWI455940B true TWI455940B (zh) | 2014-10-11 |
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TW099121933A TWI455940B (zh) | 2009-07-02 | 2010-07-02 | 新穎1,2,3,4-四氫嘧啶并[1,2-a]嘧啶-4-酮衍生物、其製備及其醫藥用途 |
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US (1) | US8846670B2 (zh) |
EP (1) | EP2448940B1 (zh) |
JP (1) | JP5655070B2 (zh) |
KR (1) | KR20120103553A (zh) |
CN (1) | CN102482286B (zh) |
AR (1) | AR077363A1 (zh) |
AU (1) | AU2010267815B2 (zh) |
BR (1) | BRPI1015943A8 (zh) |
CA (1) | CA2766909C (zh) |
DK (1) | DK2448940T3 (zh) |
ES (1) | ES2487623T3 (zh) |
HK (1) | HK1169388A1 (zh) |
HR (1) | HRP20140786T1 (zh) |
IL (1) | IL217293A (zh) |
MX (1) | MX2012000103A (zh) |
MY (1) | MY155661A (zh) |
PL (1) | PL2448940T3 (zh) |
PT (1) | PT2448940E (zh) |
RU (1) | RU2561130C2 (zh) |
SG (2) | SG177464A1 (zh) |
SI (1) | SI2448940T1 (zh) |
TW (1) | TWI455940B (zh) |
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FR2969613B1 (fr) * | 2010-12-23 | 2013-02-08 | Sanofi Aventis | Nouveaux derives de 1,2,3,4-tetrahydro-pyrimido{1,2-a}pyrimidin-6-one, leur preparation et leur utilisation pharmaceutique |
EP2655375B1 (fr) * | 2010-12-23 | 2014-12-03 | Sanofi | Derives de pyrimidinone, leur preparation et leur utilisation pharmaceutique |
MX351530B (es) | 2011-12-15 | 2017-10-18 | Novartis Ag | Uso de inhibidores de la actividad o fundicion de la pi3k. |
FR2992316A1 (fr) * | 2012-06-22 | 2013-12-27 | Sanofi Sa | Derives de pyrimidinones, leur preparation et leur application en therapeutique |
FR2992314B1 (fr) * | 2012-06-22 | 2015-10-16 | Sanofi Sa | Nouveaux derives de 2,3-dihydro-1h-imidazo{1,2-a}pyrimidin-5-one et 1,2,3,4-tetrahydro-pyrimido{1,2-a}pyrimidin-6-one comportant une morpholine substituee, leur preparation et leur utilisation pharmaceutique |
EP3828269B1 (en) | 2015-03-06 | 2023-05-03 | Korea Advanced Institute Of Science And Technology | Composition for prevention or treatment of intractable epilepsy comprising mtor inhibitor |
CN108698996B (zh) | 2016-02-19 | 2021-10-01 | 思普瑞特生物科学公司 | 可用于治疗癌症和糖尿病的6-芳基-4-吗啉-1-基吡啶酮化合物 |
CA3015005A1 (en) * | 2016-02-19 | 2017-08-24 | Sprint Bioscience Ab | 6-heterocyclyl-4-morpholin-4-ylpyridine-2-one compounds useful for the treatment of cancer and diabetes |
AU2021264512A1 (en) * | 2020-04-27 | 2022-11-17 | Aruna Bio, Inc. | Binding agents and uses thereof for central nervous system delivery |
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DE2703712A1 (de) * | 1977-01-29 | 1978-08-03 | Bayer Ag | Substituierte pyrimidinon eckige klammer auf (di)-thio eckige klammer zu -phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
MY125533A (en) * | 1999-12-06 | 2006-08-30 | Bristol Myers Squibb Co | Heterocyclic dihydropyrimidine compounds |
PT1257537E (pt) | 2000-01-24 | 2007-08-03 | Astrazeneca Ab | Compostos terapêuticos morfolino-substituídos. |
CN1267432C (zh) | 2000-09-01 | 2006-08-02 | 赛诺菲-安万特 | 2-吡啶基-6,7,8,9-四氢嘧啶并[1,2-a]嘧啶-4-酮和7-吡啶基-2,3-二氢咪唑并[1,2-a]嘧啶-5(1H)酮衍生物 |
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NZ538420A (en) | 2002-08-16 | 2007-06-29 | Kinacia Pty Ltd | Inhibition of phosphoinositide 3-kinase beta |
BR0317749A (pt) * | 2002-12-27 | 2005-11-22 | Angeletti P Ist Richerche Bio | Composto, composição farmacêutica, e, uso de um composto |
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