RU2001125421A - Способ получения трет-бутил(е)-(6-[2-[4-(4-фторфенил)-6-изопропил-2- [метил(метилсульфонил)амино]пиримидин-5-ил]винил](4r,6s)-2,2- диметил[1,3]диоксан-4-ил]ацетата - Google Patents
Способ получения трет-бутил(е)-(6-[2-[4-(4-фторфенил)-6-изопропил-2- [метил(метилсульфонил)амино]пиримидин-5-ил]винил](4r,6s)-2,2- диметил[1,3]диоксан-4-ил]ацетатаInfo
- Publication number
- RU2001125421A RU2001125421A RU2001125421/04A RU2001125421A RU2001125421A RU 2001125421 A RU2001125421 A RU 2001125421A RU 2001125421/04 A RU2001125421/04 A RU 2001125421/04A RU 2001125421 A RU2001125421 A RU 2001125421A RU 2001125421 A RU2001125421 A RU 2001125421A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- fluorophenyl
- isopropyl
- amino
- butyl
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 title claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 title claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 title claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- CVRDGWDBQZPJJI-UHFFFAOYSA-N N-[5-(diphenylphosphorylmethyl)-4-(4-fluorophenyl)-6-propan-2-ylpyrimidin-2-yl]-N-methylmethanesulfonamide Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)CC=1C(C(C)C)=NC(N(C)S(C)(=O)=O)=NC=1C1=CC=C(F)C=C1 CVRDGWDBQZPJJI-UHFFFAOYSA-N 0.000 claims 3
- 150000001768 cations Chemical class 0.000 claims 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- LXCIHXPVYQKJAG-UHFFFAOYSA-N N-[aziridin-1-yl-(2-methylaziridin-1-yl)phosphoryl]-N-prop-2-enylprop-2-en-1-amine Chemical compound CC1CN1P(=O)(N(CC=C)CC=C)N1CC1 LXCIHXPVYQKJAG-UHFFFAOYSA-N 0.000 claims 2
- 238000003776 cleavage reaction Methods 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- JEFQIIXBSQLRTF-ZJUUUORDSA-N tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate Chemical compound CC(C)(C)OC(=O)C[C@H]1C[C@@H](C=O)OC(C)(C)O1 JEFQIIXBSQLRTF-ZJUUUORDSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 150000000185 1,3-diols Chemical class 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N Sodium bis(trimethylsilyl)amide Chemical group C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims 1
- -1 compound diphenyl [4- (4-fluorophenyl) -6-isopropyl-2- [methyl- (methylsulfonyl) amino] pyrimidin-5-ylmethyl] phosphine oxide Chemical class 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000003472 neutralizing Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 230000001681 protective Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Claims (10)
1. Способ получения трет-бутил(Е)-(6-{2-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил]винил}-(4R,6S)-2,2-диметил[1,3]диоксан-4-ил]ацетата, включающий реакцию дифенил[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)-амино]пиримидин-5-илметил]фосфиноксида с трет-бутил 2-[(4R,6S)-6-формил-2,2-диметил-1,3-диоксан-4-ил]ацетатом в присутствии сильного основания.
2. Способ по п.1, в котором реакцию проводят при температуре -20 ÷ -90°С.
3. Способ по п.1 или 2, в котором сильным основанием является бис(триметилсилил)амид натрия.
4. Способ по п.1, 2 или 3, в котором реакцию проводят в растворителе, выбранном из тетрагидрофурана, диметоксиэтана и толуола и их смесей.
5. Способ по любому из пп.1-4, в котором на эквивалент фосфиноксида используют 1,0-1,2 эквивалента основания.
6. Способ по любому из пп.1-5, в котором на эквивалент фосфиноксида используют 1,0-1,35 эквивалента трет-бутил 2-[(4R,6S)-6-формил-2,2-диметил-1,3-диоксан-4-ил]ацетата.
7. Соединение дифенил[4-(4-фторфенил)-6-изопропил-2-[метил-(метилсульфонил)амино]пиримидин-5-илметил]фосфиноксид.
8. Соединение трет-бутил(Е)-(6-{2-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил]винил}-(4R,6S)-2,2-диметил[1,3]диоксан-4-ил]ацетат.
9. Способ получения соединения формулы IV
в которой R1 обозначает водород или фармацевтически приемлемый катион, который включает: (1) реакцию дифенил [4-(4-фторфенил)-6-изопропил-2-[метил(метил-сульфонил)амино]пиримидин-5-илметил]фосфиноксида с трет-бутил 2-[(4R,6S)-6-формил-2,2-диметил-1,3-диоксан-4-ил]ацетатом в присутствии сильного основания с получением трет-бутил(Е)-(6-{2-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-ил]винил}(4R,6S)-2,2-диметил[1,3]диоксан-4-ил]ацетата формулы I; (2) отщепление от продукта стадии (1) дигидрокси-защитной группы; (3) отщепление от продукта стадии (2) трет-бутильной сложноэфирной группы в условиях основной среды с образованием соединения формулы IV, в которой R1 является фармацевтически приемлемым катионом, с последующей необязательной нейтрализацией с образованием соединения формулы IV, в которой R1 обозначает водород, и/или с последующим необязательным превращением в другое соединение формулы IV, в которой R1 обозначает фармацевтически приемлемый катион.
10. Способ получения соединения формулы VI
включающий реакцию дифенил[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)амино]пиримидин-5-илметил]фосфиноксида с соединением формулы V
в присутствии сильного основания,
где Р1 и Р2 обозначают гидрозащитные группы спирта или, взятые вместе, Р1 и Р2 представляют защитную группу 1,3-диола;
Р3 обозначает защитную группу карбоновой кислоты.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9903472.0 | 1999-02-17 | ||
| GBGB9903472.0A GB9903472D0 (en) | 1999-02-17 | 1999-02-17 | Chemical process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2001125421A true RU2001125421A (ru) | 2003-06-27 |
| RU2243969C2 RU2243969C2 (ru) | 2005-01-10 |
Family
ID=10847843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2001125421/04A RU2243969C2 (ru) | 1999-02-17 | 2000-02-15 | Трет-бутил(е)-(6-{2-[4-(4-фторфенил)-6-изопропил-2-[метил(метилсульфонил)а мино]пири мидин-5-ил]винил}-(4r,6s)-2,2-диметил[1,3]диоксан-4-ил]ацетат и его способ получения, дифенил[4-(4-фторфенил)-6-изопропил-2-[метил-(метилсульфонил)амино]пиримидин-5-илме тил]фосф фонил)амино]пиримидин-5 -ил]-(3r,5s)-3,5-дигидроксигепт-6-еновой кислоты и ее производных |
Country Status (34)
| Country | Link |
|---|---|
| US (2) | US6844437B1 (ru) |
| EP (1) | EP1155015B1 (ru) |
| JP (3) | JP2003518474A (ru) |
| KR (1) | KR100648160B1 (ru) |
| CN (1) | CN1145625C (ru) |
| AR (1) | AR022600A1 (ru) |
| AT (1) | ATE415398T1 (ru) |
| AU (1) | AU760145B2 (ru) |
| BR (1) | BRPI0008301B8 (ru) |
| CA (1) | CA2362594C (ru) |
| CL (1) | CL2003002336A1 (ru) |
| CY (1) | CY1108733T1 (ru) |
| CZ (1) | CZ299844B6 (ru) |
| DE (1) | DE60040905D1 (ru) |
| DK (1) | DK1155015T3 (ru) |
| EE (2) | EE05531B1 (ru) |
| ES (1) | ES2316349T3 (ru) |
| GB (1) | GB9903472D0 (ru) |
| HK (1) | HK1041265B (ru) |
| HU (1) | HU229835B1 (ru) |
| IL (2) | IL144793A0 (ru) |
| IS (1) | IS2709B3 (ru) |
| MX (1) | MXPA01008235A (ru) |
| NO (1) | NO320739B1 (ru) |
| NZ (1) | NZ513261A (ru) |
| PL (1) | PL218518B1 (ru) |
| PT (1) | PT1155015E (ru) |
| RU (1) | RU2243969C2 (ru) |
| SI (1) | SI1155015T1 (ru) |
| SK (1) | SK286988B6 (ru) |
| TR (2) | TR200102360T2 (ru) |
| TW (1) | TWI285202B (ru) |
| WO (1) | WO2000049014A1 (ru) |
| ZA (1) | ZA200106370B (ru) |
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| KR20130087153A (ko) * | 2012-01-27 | 2013-08-06 | 코오롱생명과학 주식회사 | 로수바스타틴의 제조방법 및 이에 사용되는 중간체 화합물 |
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| KR101292743B1 (ko) * | 2012-05-17 | 2013-08-02 | (주) 에프엔지리서치 | 신규한 스타틴 중간체 및 이를 이용한 피타바스타틴, 로수바스타틴, 세리바스타틴 및 플루바스타틴의 제조 방법 |
| CN103864697A (zh) * | 2012-12-11 | 2014-06-18 | 润泽制药(苏州)有限公司 | 瑞舒伐中间体主链醇的制备方法 |
| WO2014108795A2 (en) | 2013-01-10 | 2014-07-17 | Aurobindo Pharma Limited | An improved process for the preparation of chiral diol sulfones and statins |
| CN103420919B (zh) * | 2013-08-22 | 2015-07-08 | 南京欧信医药技术有限公司 | 一种嘧啶类衍生物的合成方法 |
| WO2015037018A1 (en) * | 2013-09-14 | 2015-03-19 | Ind-Swift Laboratories Limited | Process for the preparation of rosuvastatin via novel intermediates |
| JP6240346B2 (ja) * | 2014-03-07 | 2017-11-29 | ▲凱▼菜英医▲薬▼集▲団▼（天津）股▲フン▼有限公司 | ロスバスタチンカルシウムを製造するための中間体化合物、及びそれを用いてロスバスタチンカルシウムを製造する方法 |
| CN103936680B (zh) * | 2014-04-18 | 2016-08-24 | 润泽制药(苏州)有限公司 | 瑞舒伐他汀钙已知杂质的制备方法 |
| CN104788387A (zh) * | 2015-04-17 | 2015-07-22 | 浙江海森药业有限公司 | 高纯度瑞舒伐他汀钙的制备方法 |
| KR20160126700A (ko) | 2015-04-24 | 2016-11-02 | 미래파인켐 주식회사 | 스타틴의 중간체, 이의 제조방법 및 이를 이용한 로수바스타틴의 제조방법 |
| CN105461636A (zh) * | 2015-12-30 | 2016-04-06 | 安徽美诺华药物化学有限公司 | 一种瑞舒伐他汀甲酯的合成方法 |
| CN106478518A (zh) * | 2016-09-27 | 2017-03-08 | 南通常佑药业科技有限公司 | 一种庚烯酸环戊酯衍生物的制备方法 |
| KR101953575B1 (ko) | 2016-10-24 | 2019-05-24 | 한양대학교 에리카산학협력단 | 스타틴계 고지혈증 치료제 합성을 위한 새로운 중간체 합성 및 이를 이용한 로수바스타틴 합성 공정 개발 |
| CN108997324A (zh) * | 2018-08-21 | 2018-12-14 | 南京欧信医药技术有限公司 | 瑞舒伐他汀钙中间体的制备方法 |
| CN109651259B (zh) * | 2018-12-29 | 2020-05-19 | 浙江永太科技股份有限公司 | 一种瑞舒伐他汀钙关键中间体的纯化方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3741509A1 (de) | 1987-12-08 | 1989-06-22 | Hoechst Ag | Verfahren zur herstellung optisch aktiver 3-desmethylmevalonsaeurederivate sowie zwischenprodukte |
| JP2648897B2 (ja) * | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
| FR2741620B1 (fr) * | 1995-11-28 | 1997-12-26 | Oreal | Procede de preparation de composes a groupement beta-hydroxy -delta-lactone analogues de la (+) compactine et de la (+) mevinoline |
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