RU2015108944A - Способ синтеза ингибиторов е1-активирующего фермента - Google Patents
Способ синтеза ингибиторов е1-активирующего фермента Download PDFInfo
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Abstract
1. Соединение формулы RN-S(O)X,где Rвыбран из -C(O)OCMe, -C(O)OCHPh, -C(O)N(Ph), -C(O)OC(Me)Ph, -C(O)OCH(Me)Ph, C(O)OC(Me)Et, -C(O)OC(Et)Ph, -C(O)OC(octyl)Ph,, и; иX представляет собой(a) третичный амин, выбранный из триметиламина, триэтилендиамина, диазабицикло[5.4.0]ундец-7-ена (DBU), 1,4-диазабицикло[2.2.2]октана, 1,5-диазабицикло[4.3.0]нон-5-ена, спартеина, N,N'-диизопропилэтиламина, трибутиламина, 1-азабицикло[2.2.2]октана, N,N'-диметилпиперазина, N-этилморфолина и трипропиламина; или(в) азотсодержащий гетероарил, выбранный из группы, состоящей из незамещенного или замещенного пиридина, незамещенного или замещенного имидазола или незамещенного или замещенного пиррола.2. Соединение по п. 1, где Rпредставляет собой -C(O)OCMe.3. Соединение по любому из пп. 1 и 2, где X представляет собой триэтилендиамин.4. Комплекс, включающий соединение формулы RN-S(O)Xкак определено по любому из пп. 1-3 и хлористо-водородная соль радикала X.5. Комплекс по п. 4, где соотношение соединения формулы RN-S(O)Xк хлористо-водородной соли X в комплексе составляет менее 1, соотношение соединения формулы RN-S(O)Xк хлористо-водородной соли X в комплексе составляет около 1 или соотношение соединения формулы RN-S(O)Xк хлористо-водородной соли_X в комплексе составляет более 1.6. Способ получения соединения формулы RN-S(O)X, включающий стадии:I-E) обработку (R)(R)C-OH хлорсульфонилизоцианатом;II-E) обработку реакционной смеси, образованной на стадии I-E) X; иIII-E) отделение реагента сульфамоилирования RNS(O) -X;причем Rпредставляет собой метил или фенил; каждый Rнезависимо представляет собой водород, метил, этил, октил или фенил; или один из Rвместе с Rпредставляет собой циклопропил или циклогексил;Rи X определены в пп. 1-3.
Claims (6)
1. Соединение формулы RuN--S(O)2X+,
где Ru выбран из -C(O)OCMe3, -C(O)OCH2Ph, -C(O)N(Ph)2, -C(O)OC(Me)2Ph, -C(O)OCH(Me)Ph, C(O)OC(Me)2Et, -C(O)OC(Et)2Ph, -C(O)OC(octyl)2Ph,
X представляет собой
(a) третичный амин, выбранный из триметиламина, триэтилендиамина, диазабицикло[5.4.0]ундец-7-ена (DBU), 1,4-диазабицикло[2.2.2]октана, 1,5-диазабицикло[4.3.0]нон-5-ена, спартеина, N,N'-диизопропилэтиламина, трибутиламина, 1-азабицикло[2.2.2]октана, N,N'-диметилпиперазина, N-этилморфолина и трипропиламина; или
(в) азотсодержащий гетероарил, выбранный из группы, состоящей из незамещенного или замещенного пиридина, незамещенного или замещенного имидазола или незамещенного или замещенного пиррола.
2. Соединение по п. 1, где Ru представляет собой -C(O)OCMe3.
3. Соединение по любому из пп. 1 и 2, где X представляет собой триэтилендиамин.
4. Комплекс, включающий соединение формулы RuN--S(O)2X+ как определено по любому из пп. 1-3 и хлористо-водородная соль радикала X.
5. Комплекс по п. 4, где соотношение соединения формулы RuN--S(O)2X+ к хлористо-водородной соли X в комплексе составляет менее 1, соотношение соединения формулы RuN--S(O)2X+ к хлористо-водородной соли X в комплексе составляет около 1 или соотношение соединения формулы RuN--S(O)2X+ к хлористо-водородной соли_X в комплексе составляет более 1.
6. Способ получения соединения формулы RuN--S(O)2X+, включающий стадии:
I-E) обработку (Rw)(Rv)2C-OH хлорсульфонилизоцианатом;
II-E) обработку реакционной смеси, образованной на стадии I-E) X; и
III-E) отделение реагента сульфамоилирования RuNS(O)2 --X+;
причем Rw представляет собой метил или фенил; каждый Rv независимо представляет собой водород, метил, этил, октил или фенил; или один из Rv вместе с Rw представляет собой циклопропил или циклогексил;
Ru и X определены в пп. 1-3.
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US96300807P | 2007-08-02 | 2007-08-02 | |
US60/963,008 | 2007-08-02 | ||
US6237808P | 2008-01-25 | 2008-01-25 | |
US61/062,378 | 2008-01-25 |
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RU2010107471/04A Division RU2553476C2 (ru) | 2007-08-02 | 2008-08-01 | Способ синтеза ингибиторов е1-активирующего фермента |
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RU2010107471/04A RU2553476C2 (ru) | 2007-08-02 | 2008-08-01 | Способ синтеза ингибиторов е1-активирующего фермента |
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US (3) | US8933225B2 (ru) |
EP (4) | EP2540727B1 (ru) |
JP (3) | JP5479336B2 (ru) |
KR (2) | KR101925902B1 (ru) |
CN (3) | CN101868461B (ru) |
AU (1) | AU2008305767B2 (ru) |
CA (2) | CA2949336C (ru) |
ES (4) | ES2655028T3 (ru) |
IL (2) | IL203590A (ru) |
MX (1) | MX2010001126A (ru) |
RU (2) | RU2015108944A (ru) |
TW (2) | TW201434851A (ru) |
WO (1) | WO2009042013A1 (ru) |
ZA (1) | ZA201000482B (ru) |
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CN101868461B (zh) | 2007-08-02 | 2013-09-25 | 米伦纽姆医药公司 | 合成e1活化酶抑制剂的方法 |
CN104016987A (zh) | 2009-05-14 | 2014-09-03 | 米伦纽姆医药公司 | 氨基磺酸((1s,2s,4r)-4-{4-[(1s)-2,3-二氢-1h-茚-1-基氨基]-7h-吡咯并[2,3-d]嘧啶-7-基}-2-羟基环戊基)甲酯盐酸盐 |
JP2013541587A (ja) * | 2010-11-05 | 2013-11-14 | ミレニアム ファーマシューティカルズ, インコーポレイテッド | Nedd8活性化酵素阻害剤の投与 |
SG11201404757WA (en) | 2012-02-17 | 2014-09-26 | Millennium Pharm Inc | Pyrazolopyrimidinyl inhibitors of ubiquitin-activating enzyme |
CN104072381B (zh) * | 2013-03-26 | 2017-04-12 | 安徽贝克联合制药有限公司 | 光学纯氨基醇盐酸盐的制备方法 |
WO2014186388A2 (en) | 2013-05-14 | 2014-11-20 | Millennium Pharmaceutcals, Inc. | Administration of nedd8-activating enzyme inhibitor and chemotherapeutic agents |
CN106999479B (zh) | 2014-07-01 | 2021-07-16 | 米伦纽姆医药公司 | 可用作sumo活化酶抑制剂的杂芳基化合物 |
EP3212651B1 (en) | 2014-10-29 | 2021-02-24 | Millennium Pharmaceuticals, Inc. | Administration of ubiquitin-activating enzyme inhibitor and radiation |
CN104974051A (zh) * | 2015-06-30 | 2015-10-14 | 苏州开元民生科技股份有限公司 | (1S,4R)-cis-4-氨基-2-环戊烯-1-甲醇盐酸盐的合成方法 |
CN106854208B (zh) * | 2016-11-25 | 2019-04-09 | 成都柏睿泰生物科技有限公司 | 肿瘤抑制剂mln4924的合成方法 |
WO2019060536A1 (en) | 2017-09-21 | 2019-03-28 | Millennium Pharmaceuticals, Inc. | CO-CRYSTALLINE FORMS OF ((1S, 2S, 4R) -4- {4 - [(1S) -2,3-DIHYDRO-1H-INDEN-1-YLAMINO] -7H-PYRROLO [2,3-D] PYRIMIDIN -7-YL} -2-HYDROXYCYCLOPENTYL) METHYLSULFAMATE, THEIR FORMULATIONS AND USES |
KR102018341B1 (ko) * | 2018-06-21 | 2019-09-04 | 성균관대학교산학협력단 | RNF170 및 pUL50을 유효성분으로 포함하는 암 예방 또는 치료용 약학적 조성물 |
JP2022522534A (ja) | 2019-04-02 | 2022-04-19 | アリゴス セラピューティクス インコーポレイテッド | Prmt5を標的にする化合物 |
WO2022112951A1 (en) | 2020-11-25 | 2022-06-02 | Takeda Pharmaceutical Company Limited | Solid state forms of hydrochloride salt of ((1s,2s,4r)-4-{4-[(1s)-2,3-dihydro-1h-inden-1-ylamino]-7h-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl sulfamate |
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