HRP20151328T1 - POSTUPAK ZA PRIPRAVU BENZIL[(3aS,4R,6S,6aR)-6-HIDROKSI-2,2- DIMETILTETRAHIDRO-3aH-CIKLOPENTA[d][1,3]DIOKSOL]-4-IL]KARBAMATA I INTERMEDIJERI U POSTUPKU - Google Patents
POSTUPAK ZA PRIPRAVU BENZIL[(3aS,4R,6S,6aR)-6-HIDROKSI-2,2- DIMETILTETRAHIDRO-3aH-CIKLOPENTA[d][1,3]DIOKSOL]-4-IL]KARBAMATA I INTERMEDIJERI U POSTUPKU Download PDFInfo
- Publication number
- HRP20151328T1 HRP20151328T1 HRP20151328TT HRP20151328T HRP20151328T1 HR P20151328 T1 HRP20151328 T1 HR P20151328T1 HR P20151328T T HRP20151328T T HR P20151328TT HR P20151328 T HRP20151328 T HR P20151328T HR P20151328 T1 HRP20151328 T1 HR P20151328T1
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- HR
- Croatia
- Prior art keywords
- solvent
- image
- amino acid
- dimethyltetrahydro
- cyclopenta
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (10)
1. Postupak za pripravu benzil [(3aS,4R,6S,6aR)-6-hidroksi-2,2-dimetiltetrahidro-3aH-ciklopenta[d][1,3]dioksol-4-il]karbamata (VI),
[image]
naznačen time da sadrži korake
(a) miješanje spoja s formulom (III),
[image]
s 0.5 do 0.8 ekvivalenata enantiomerno čiste zaštićene amino kiseline odabrane od L-Boc-fenilalanina ili L-Boc-leucina da se dobije diastereoizomerna sol;
(b) kristalizaciju navedene soli da nastane zaštićena sol amino kiseline spoja s formulom (IV),
[image]
(c) obradu zaštićene soli amino kiseline spoja s formulom (IV) s kiselinom; i
(d) reakciju produkta iz koraka c) s benzil kloroformatom u prisutnosti prikladne baze, kao što je kalijev karbonat.
2. Postupak prema zahtjevu 1, naznačen time da je otapalo iz koraka (a) odabrano od alifatskih alkohola, alifatskih estera, alifatskih ketona, aromatskih otapala i njihovih smjesa.
3. Postupak prema zahtjevu 2, naznačen time da je otapalo iz koraka (a) smjesa izo-propanola i toluena.
4. Postupak prema zahtjevu 2, naznačen time da je otapalo iz koraka (a) izo-propanol.
5. Postupak prema zahtjevu 2, naznačen time da je otapalo iz koraka (a) smjesa metil izo-butil ketona i toluena.
6. Postupak prema zahtjevu 2, naznačen time da je otapalo iz koraka (a) metil izo-butil keton.
7. Postupak prema bilo kojem od zahtjeva 1-6 naznačen time da je enantiomerno čista zaštićena amino kiselina L-Boc-fenilalanin.
8. Postupak prema bilo kojem od zahtjeva 1-6 naznačen time da je enantiomerno čista zaštićena amino kiselina L-Boc-leucin.
9. Intermedijerni spoj naznačen time da je (3aS,4R,6S,6aR)-6-hidroksi-2,2-dimetiltetrahidro-3aH-ciklopenta[d][1,3]dioksol-4-aminij (2S)-2-[(tert-butoksikarbonil)amino]-3-fenilpropanoat (Va),
[image]
10. Intermedijerni spoj naznačen time da je (3aS,4R,6S,6aR)-6-hidroksi-2,2-dimetiltetrahidro-3aH-ciklopenta[d][1,3]dioksol-4-aminij (2S)-2-[(tert-butoksikarbonil)amino]-4-metilpentanoat (Vb),
[image]
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161485691P | 2011-05-13 | 2011-05-13 | |
| US201161540084P | 2011-09-28 | 2011-09-28 | |
| EP12785416.4A EP2707363B1 (en) | 2011-05-13 | 2012-05-11 | A process for the preparation of benzyl [(3as,4r,6s,6ar)-6-hydroxy-2,2- dimethyltetrahydro-3ah-cyclopenta[d][1,3]dioxol]-4-yl]carbamate and intermediates in the process |
| PCT/SE2012/050498 WO2012158099A1 (en) | 2011-05-13 | 2012-05-11 | A process for the preparation of benzyl [(3as,4r,6s,6ar)-6-hydroxy-2,2- dimethyltetrahydro-3ah-cyclopenta[d][1,3]dioxol]-4-yl]carbamate and intermediates in the process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20151328T1 true HRP20151328T1 (hr) | 2016-01-01 |
Family
ID=47177189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20151328TT HRP20151328T1 (hr) | 2011-05-13 | 2012-05-11 | POSTUPAK ZA PRIPRAVU BENZIL[(3aS,4R,6S,6aR)-6-HIDROKSI-2,2- DIMETILTETRAHIDRO-3aH-CIKLOPENTA[d][1,3]DIOKSOL]-4-IL]KARBAMATA I INTERMEDIJERI U POSTUPKU |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US9079873B2 (hr) |
| EP (1) | EP2707363B1 (hr) |
| JP (1) | JP6023795B2 (hr) |
| KR (1) | KR20140028070A (hr) |
| CN (1) | CN103534245B (hr) |
| AR (1) | AR086351A1 (hr) |
| AU (1) | AU2012256439B2 (hr) |
| BR (1) | BR112013028936B1 (hr) |
| CA (1) | CA2834935A1 (hr) |
| CY (1) | CY1117592T1 (hr) |
| DK (1) | DK2707363T3 (hr) |
| ES (1) | ES2556833T3 (hr) |
| HR (1) | HRP20151328T1 (hr) |
| HU (1) | HUE027145T2 (hr) |
| IL (1) | IL229075A (hr) |
| MX (1) | MX2013013221A (hr) |
| MY (1) | MY163203A (hr) |
| PL (1) | PL2707363T3 (hr) |
| PT (1) | PT2707363E (hr) |
| RS (1) | RS54443B1 (hr) |
| RU (1) | RU2588673C2 (hr) |
| SG (1) | SG194585A1 (hr) |
| SI (1) | SI2707363T1 (hr) |
| SM (1) | SMT201500309B (hr) |
| TW (1) | TWI537256B (hr) |
| WO (1) | WO2012158099A1 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104513221A (zh) * | 2013-09-26 | 2015-04-15 | 上海科胜药物研发有限公司 | 一种制备光学活性的替卡格雷中间体的方法 |
| CN108484566A (zh) * | 2018-02-26 | 2018-09-04 | 苏州楚凯药业有限公司 | 一种替格瑞洛关键中间体的制备方法 |
| CN117551071A (zh) * | 2023-10-13 | 2024-02-13 | 重庆普佑生物医药有限公司 | 替卡格雷中间体及其制备方法和应用该中间体的合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9702772D0 (sv) * | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
| US6316671B1 (en) * | 1997-11-28 | 2001-11-13 | Universite De Rouen | Method for splitting 1-amino-alkan-2-ol compounds |
| TWI229674B (en) * | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
| JP4406483B2 (ja) * | 1999-11-17 | 2010-01-27 | 株式会社デ・ウエスタン・セラピテクス研究所 | 光学活性２−アミノシクロヘキサノール誘導体の製造方法 |
| GB0013488D0 (en) * | 2000-06-02 | 2000-07-26 | Astrazeneca Ab | Chemical compound |
| JP2005104874A (ja) * | 2003-09-29 | 2005-04-21 | Yamakawa Yakuhin Kogyo Kk | 光学活性なα−アミノ−ε−カプロラクタムまたはその塩の製造方法および製造の中間体 |
| JPWO2007055180A1 (ja) * | 2005-11-09 | 2009-04-30 | 東レ・ファインケミカル株式会社 | 光学活性トランス−２−アミノシクロヘキサノールおよびその誘導体の製造方法 |
| JP2009023978A (ja) * | 2007-07-23 | 2009-02-05 | Kaneka Corp | トランス−２−ベンジロキシシクロヘキシルアミンの製造法 |
| TWI496776B (zh) * | 2007-11-15 | 2015-08-21 | Astrazeneca Ab | 製備(3aR,4S,6R,6aS)-6-胺基-2,2-二甲基四氫-3aH-環戊并[d][1,3]二氧雜環戊烯-4-醇之純非對映異構性之二苯甲醯-L-酒石酸鹽之方法 |
| RU2400478C1 (ru) * | 2009-02-24 | 2010-09-27 | Учреждение Российской академии наук Институт органической химии Уфимского научного центра РАН | Способ получения (4s,5s)-4,5-о-изопропилиденциклопент-2-ен-1-она |
| JP2013500347A (ja) * | 2009-07-27 | 2013-01-07 | オースペックス ファーマシューティカルズ，インク． | Ｐ２ｙ１２受容体のシクロプロピルモジュレーター |
-
2012
- 2012-05-11 CA CA2834935A patent/CA2834935A1/en not_active Abandoned
- 2012-05-11 HU HUE12785416A patent/HUE027145T2/en unknown
- 2012-05-11 SI SI201230397T patent/SI2707363T1/sl unknown
- 2012-05-11 JP JP2014510277A patent/JP6023795B2/ja active Active
- 2012-05-11 WO PCT/SE2012/050498 patent/WO2012158099A1/en active Application Filing
- 2012-05-11 TW TW101116976A patent/TWI537256B/zh active
- 2012-05-11 PT PT127854164T patent/PT2707363E/pt unknown
- 2012-05-11 AU AU2012256439A patent/AU2012256439B2/en active Active
- 2012-05-11 US US14/117,077 patent/US9079873B2/en active Active
- 2012-05-11 KR KR1020137032916A patent/KR20140028070A/ko not_active Withdrawn
- 2012-05-11 DK DK12785416.4T patent/DK2707363T3/en active
- 2012-05-11 CN CN201280023753.3A patent/CN103534245B/zh active Active
- 2012-05-11 RS RS20150821A patent/RS54443B1/en unknown
- 2012-05-11 PL PL12785416T patent/PL2707363T3/pl unknown
- 2012-05-11 MY MYPI2013702133A patent/MY163203A/en unknown
- 2012-05-11 BR BR112013028936-8A patent/BR112013028936B1/pt active IP Right Grant
- 2012-05-11 RU RU2013150325/04A patent/RU2588673C2/ru active
- 2012-05-11 EP EP12785416.4A patent/EP2707363B1/en active Active
- 2012-05-11 ES ES12785416.4T patent/ES2556833T3/es active Active
- 2012-05-11 MX MX2013013221A patent/MX2013013221A/es unknown
- 2012-05-11 HR HRP20151328TT patent/HRP20151328T1/hr unknown
- 2012-05-11 AR ARP120101663A patent/AR086351A1/es active IP Right Grant
- 2012-05-11 SG SG2013078621A patent/SG194585A1/en unknown
-
2013
- 2013-10-24 IL IL229075A patent/IL229075A/en active IP Right Grant
-
2015
- 2015-12-09 SM SM201500309T patent/SMT201500309B/it unknown
- 2015-12-15 CY CY20151101145T patent/CY1117592T1/el unknown
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