RU2002135596A - Новые триазолопиримидиновые соединения - Google Patents
Новые триазолопиримидиновые соединенияInfo
- Publication number
- RU2002135596A RU2002135596A RU2002135596/04A RU2002135596A RU2002135596A RU 2002135596 A RU2002135596 A RU 2002135596A RU 2002135596/04 A RU2002135596/04 A RU 2002135596/04A RU 2002135596 A RU2002135596 A RU 2002135596A RU 2002135596 A RU2002135596 A RU 2002135596A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- compounds
- iii
- obtaining
- Prior art date
Links
- YWBFPKPWMSWWEA-UHFFFAOYSA-O TRIAZOLOPYRIMIDINE Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 49
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011780 sodium chloride Substances 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 230000003993 interaction Effects 0.000 claims 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N Benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal nitrite Chemical class 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- JQNFPAVZYDALFH-PKPIPKONSA-N N[C@@H](CC1)CC1OCCO Chemical compound N[C@@H](CC1)CC1OCCO JQNFPAVZYDALFH-PKPIPKONSA-N 0.000 description 2
- RACKWKJESSZWBC-HSBZDZAISA-N CC(C)(O)OC(C[C@H](C1)O)C1NC(OCc1ccccc1)=O Chemical compound CC(C)(O)OC(C[C@H](C1)O)C1NC(OCc1ccccc1)=O RACKWKJESSZWBC-HSBZDZAISA-N 0.000 description 1
- VOPKERUBJOMKGX-UHFFFAOYSA-N CCCSc1nc(N=C)c2nn[n](C(CC3)CC3OCCO)c2n1 Chemical compound CCCSc1nc(N=C)c2nn[n](C(CC3)CC3OCCO)c2n1 VOPKERUBJOMKGX-UHFFFAOYSA-N 0.000 description 1
- BAPGQTRADPOZCX-UHFFFAOYSA-N CCCSc1nc([ClH]C)c(C(/C=N/[Al]=C)=C)c([ClH]C)n1 Chemical compound CCCSc1nc([ClH]C)c(C(/C=N/[Al]=C)=C)c([ClH]C)n1 BAPGQTRADPOZCX-UHFFFAOYSA-N 0.000 description 1
- XJXVTLRKVJBWFN-UHFFFAOYSA-N Fc1ccc(C2CC2)cc1F Chemical compound Fc1ccc(C2CC2)cc1F XJXVTLRKVJBWFN-UHFFFAOYSA-N 0.000 description 1
Claims (17)
3. Способ получения соединения формулы (I) по п.2, включающий гидрирование соединения формулы (IV)
в которой Ar представляет фенил, необязательно замещенный галогеном, С1-4алкилом или С1-4алкокси, с получением соединения формулы (II) и взаимодействие соединения формулы (II) с соединением формулы (III), с получением соединения формулы (I).
6. Применение соединения формулы (I) для получения соединения формулы (А)
включающий а) взаимодействие соединения формулы (I) с нитритом щелочного металла в присутствии подходящей кислоты с получением соединения формулы (VII)
b) сочетание соединения формулы (VII) с соединением формулы (VI):
с получением соединения формулы (V)
и
с) снятие защиты с соединения формулы (V) с получением соединения формулы А.
8. Способ получения соли соединения формулы (III)
включающий стадии а) получения соединения формулы (XI)
взаимодействием соединения формулы (XII)
с бензилхлорформиатом;
b) получения соединения формулы (Х)
взаимодействием соединения формулы (XI) с соединением L-CH2CO2R* {где R* представляет С1-4алкил, и L представляет уходящую группу};
с) получения соединения формулы (IX)
восстановлением соединения формулы (Х);
d) получения соединения формулы (III)
снятием защиты с соединения формулы (IX); и
e) получения соли соединения формулы (III) взаимодействием соединения формулы (III) с необходимой кислотой.
9. Промежуточное соединение следующей формулы:
где оба R’ одновременно представляют собой Cl, а X означает группу H2N- или Ar-N=N-, причем Ar является фенилом, который необязательно замещен галогеном, C1-4-алкилом или C1-4-алкокси; или оба R’ одновременно представляют собой OH, а X означает группу Ar-N=N-, где Ar определен как указано выше.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0013488.2 | 2000-06-02 | ||
GBGB0013488.2A GB0013488D0 (en) | 2000-06-02 | 2000-06-02 | Chemical compound |
SE0002102A SE0002102D0 (sv) | 2000-06-02 | 2000-06-06 | Chemical compound |
SE0002102-2 | 2000-06-06 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2002135596A true RU2002135596A (ru) | 2004-06-27 |
RU2295526C2 RU2295526C2 (ru) | 2007-03-20 |
Family
ID=26244413
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2002135596/04A RU2295526C2 (ru) | 2000-06-02 | 2001-05-31 | Пиримидиновые соединения, способ их получения (варианты), промежуточные продукты (варианты) и способы их получения (варианты), способ получения триазолопиримидиновых соединений |
Country Status (36)
Country | Link |
---|---|
US (6) | US7067663B2 (ru) |
EP (1) | EP1299390B1 (ru) |
JP (1) | JP4947870B2 (ru) |
KR (2) | KR100814229B1 (ru) |
CN (3) | CN101143864A (ru) |
AR (1) | AR028605A1 (ru) |
AT (1) | ATE386039T1 (ru) |
AU (4) | AU2001262876B2 (ru) |
BG (1) | BG65866B1 (ru) |
BR (1) | BR0111319A (ru) |
CA (1) | CA2408914C (ru) |
CY (1) | CY1108101T1 (ru) |
CZ (3) | CZ302645B6 (ru) |
DE (1) | DE60132776T2 (ru) |
DK (1) | DK1299390T3 (ru) |
EE (1) | EE05223B1 (ru) |
ES (1) | ES2299487T3 (ru) |
GB (1) | GB0013488D0 (ru) |
HK (1) | HK1053122A1 (ru) |
HU (1) | HU229281B1 (ru) |
IL (3) | IL152776A0 (ru) |
IS (1) | IS2600B (ru) |
MX (2) | MXPA02011793A (ru) |
MY (1) | MY131942A (ru) |
NO (1) | NO324266B1 (ru) |
NZ (1) | NZ522637A (ru) |
PL (3) | PL212128B1 (ru) |
PT (1) | PT1299390E (ru) |
RU (1) | RU2295526C2 (ru) |
SE (1) | SE0002102D0 (ru) |
SI (1) | SI1299390T1 (ru) |
SK (1) | SK286845B6 (ru) |
TW (1) | TWI285203B (ru) |
UA (1) | UA73182C2 (ru) |
WO (1) | WO2001092263A1 (ru) |
ZA (1) | ZA200209068B (ru) |
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SE0400873D0 (sv) * | 2004-03-31 | 2004-03-31 | Astrazeneca Ab | Chemical process |
SE0401001D0 (sv) * | 2004-03-31 | 2004-03-31 | Astrazeneca Ab | Chemical process |
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CN112457316B (zh) * | 2020-11-05 | 2022-04-12 | 南通常佑药业科技有限公司 | 一种应用连续流反应技术制备替卡格雷高级中间体的方法 |
CN112724119B (zh) * | 2020-12-30 | 2022-05-03 | 江苏恒沛药物科技有限公司 | 一种替卡格雷关键中间体的合成方法 |
CN115160320B (zh) * | 2022-06-27 | 2024-05-07 | 南通常佑药业科技有限公司 | 一种手性嘧啶并三唑类替格瑞洛的制备方法 |
CN115785058B (zh) * | 2022-12-09 | 2024-05-03 | 广州康瑞泰药业有限公司 | 一种合成替格瑞洛五元环中间体的方法 |
CN116535384A (zh) * | 2023-04-17 | 2023-08-04 | 重庆普佑生物医药有限公司 | 替卡格雷中间体的制备方法 |
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DE3040406A1 (de) * | 1980-10-27 | 1982-05-27 | Degussa Ag, 6000 Frankfurt | Verfahren zur gewinnung von n-tert-alkylaminen und ameisensaeureestern |
GB8916477D0 (en) | 1989-07-19 | 1989-09-06 | Glaxo Group Ltd | Chemical process |
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US5654285A (en) | 1991-04-06 | 1997-08-05 | Astra Pharmaceuticals Limited | ADP and ATP analogues, process for making and administration to inhibit ADP-induced platelet aggregation |
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EP0946561B1 (en) * | 1996-12-20 | 2002-02-13 | AstraZeneca AB | Triazolo(4,5-d)pyrimidinyl derivatives and their use as medicaments |
SE9702773D0 (sv) * | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
TW530058B (en) * | 1997-07-22 | 2003-05-01 | Astra Pharma Prod | Triazolo [4,5-d]pyrimidine compounos and their use and process for preparation |
NZ505250A (en) | 1998-02-17 | 2002-10-25 | Astrazeneca Uk Ltd | Novel triazolo(4,5-d) pyrimidine compounds and pharmaceuticals thereof. |
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 |
CZ20002947A3 (cs) * | 1999-02-05 | 2000-11-15 | Astrazeneca Uk Limited | Nové triazolo(4,5-d)pyrimidiny, způsob jejich přípravy a farmaceutický prostředek, který je obsahuje |
SE9904129D0 (sv) | 1999-11-15 | 1999-11-15 | Astra Pharma Prod | Novel compounds |
GB0013407D0 (en) * | 2000-06-02 | 2000-07-26 | Astrazeneca Ab | Forms of a chemical compound |
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