RU2003123791A - Способ карбамоилирования спиртов - Google Patents
Способ карбамоилирования спиртов Download PDFInfo
- Publication number
- RU2003123791A RU2003123791A RU2003123791/04A RU2003123791A RU2003123791A RU 2003123791 A RU2003123791 A RU 2003123791A RU 2003123791/04 A RU2003123791/04 A RU 2003123791/04A RU 2003123791 A RU2003123791 A RU 2003123791A RU 2003123791 A RU2003123791 A RU 2003123791A
- Authority
- RU
- Russia
- Prior art keywords
- alcohol
- cyanate
- paragraph
- reaction mixture
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 12
- 150000001298 alcohols Chemical class 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 17
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 10
- 229940098779 methanesulfonic acid Drugs 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 230000021235 carbamoylation Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 2
- IGZGOSZOYWXTLI-UHFFFAOYSA-M cesium;cyanate Chemical compound [Cs+].[O-]C#N IGZGOSZOYWXTLI-UHFFFAOYSA-M 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Claims (11)
1. Способ карбамоилирования спирта, включающий взаимодействие спирта с цианатом натрия в присутствии метансульфокислоты в безводных условиях.
2. Способ по пункту 1, где спирт дополнительно содержит сульфенильную часть и азотсодержащую гетероциклическую часть.
3. Способ по пункту 1, где спиртом является каправиринсульфениловый спирт.
4. Способ карбамоилирования спирта, включающий
смешивание спирта с цианатом в инертном растворителе в безводных условиях, где спирт содержит другие части;
охлаждение образующейся реакционной смеси до температуры от примерно -25 до примерно 40°С;
добавление кислоты к охлажденной реакционной смеси со скоростью, поддерживающей температуру ниже примерно 0°С;
перемешивание реакционной смеси, содержащей метансульфокислоту, при температуре от примерно -10°С до примерно 0°С в течение примерно от 8 до 10 ч; и
гашение реакционной смеси водой.
5. Способ по пункту 4, где спирт содержит сульфенильную часть и азотсодержащую гетероциклическую часть, которая выбрана из имидазолила и пиридила.
6. Способ по пункту 4, где спиртом является каправиринсульфениловый спирт.
7. Способ по пункту 4, где цианат представляет цианат натрия, цианат калия, цианат цезия или их смесь, и кислота представляет метансульфокислоту, уксусную кислоту, серную кислоту или их смесь.
8. Способ по пункту 4, где смешивание предусматривает использование молярного отношения метансульфокислоты и спирта от примерно 5 до примерно 20 и молярного отношения цианата натрия и спирта от примерно 1,5 до примерно 2,0.
9. Способ по пункту 4, где смешивание предусматривает использование молярного отношения метансульфокислоты и спирта от примерно 9 до примерно 10 и молярного отношения цианата натрия и спирта примерно 1,65.
10. Способ по пункту 4, где реакционную смесь цианата и спирта охлаждают до температуры от -10 до примерно 0°С.
11. Способ по пункту 4, дополнительно включающий выделение и очистку карбамоилированного спирта.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26550201P | 2001-01-31 | 2001-01-31 | |
| US60/265,502 | 2001-01-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003123791A true RU2003123791A (ru) | 2005-02-27 |
| RU2256657C2 RU2256657C2 (ru) | 2005-07-20 |
Family
ID=23010706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003123791/04A RU2256657C2 (ru) | 2001-01-31 | 2002-01-11 | Способ карбамоилирования спиртов |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6613908B2 (ru) |
| EP (1) | EP1377568A1 (ru) |
| JP (1) | JP2004518687A (ru) |
| KR (1) | KR100567706B1 (ru) |
| CN (1) | CN1243748C (ru) |
| AR (1) | AR032419A1 (ru) |
| BR (1) | BR0206806A (ru) |
| CA (1) | CA2433364A1 (ru) |
| CZ (1) | CZ20032001A3 (ru) |
| HU (1) | HUP0303028A3 (ru) |
| IL (1) | IL156363A0 (ru) |
| MX (1) | MXPA03005403A (ru) |
| PL (1) | PL363321A1 (ru) |
| RU (1) | RU2256657C2 (ru) |
| TW (1) | TWI228507B (ru) |
| WO (1) | WO2002060893A1 (ru) |
| YU (1) | YU52303A (ru) |
| ZA (1) | ZA200304687B (ru) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL1628685T3 (pl) | 2003-04-25 | 2011-05-31 | Gilead Sciences Inc | Przeciwwirusowe analogi fosfonianowe |
| EP1656387A2 (en) * | 2003-07-30 | 2006-05-17 | Gilead Sciences, Inc. | Nucleobase phosphonate analogs for antiviral treatment |
| WO2005016912A1 (en) * | 2003-08-19 | 2005-02-24 | Pfizer Inc. | An efficient microbial preparation of capravirine metabolites m4 and m5 |
| US20050080268A1 (en) * | 2003-10-08 | 2005-04-14 | Yong-Moon Choi | Process of preparing O-carbamoyl compounds in the presence of active amine group |
| DK1778702T3 (da) * | 2004-07-16 | 2011-10-17 | Gilead Sciences Inc | Antivirale forbindelser |
| EP1778251B1 (en) | 2004-07-27 | 2011-04-13 | Gilead Sciences, Inc. | Nucleoside phosphonate conjugates as anti hiv agents |
| TW200738742A (en) * | 2005-07-14 | 2007-10-16 | Gilead Sciences Inc | Antiviral compounds |
| TWI389908B (zh) * | 2005-07-14 | 2013-03-21 | Gilead Sciences Inc | 抗病毒化合物類 |
| US20080076740A1 (en) * | 2005-07-27 | 2008-03-27 | Gilead Sciences, Inc. | Antiviral compounds |
| WO2008005542A2 (en) * | 2006-07-07 | 2008-01-10 | Gilead Sciences, Inc., | Antiviral phosphinate compounds |
| AU2009268681B2 (en) * | 2008-07-08 | 2014-10-02 | Gilead Sciences, Inc. | Salts of HIV inhibitor compounds |
| US8810796B2 (en) | 2009-04-21 | 2014-08-19 | Michigan Aerospace Corporation | Light processing system and method |
| EP3661937B1 (en) | 2017-08-01 | 2021-07-28 | Gilead Sciences, Inc. | Crystalline forms of ethyl ((s)-((((2r,5r)-5-(6-amino-9h-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl)oxy)methyl)(phenoxy)phosphoryl)-l-alaninate (gs-9131) for treating viral infections |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2611695A1 (de) * | 1976-03-19 | 1977-09-29 | Hoechst Ag | Herbizide mittel |
| DE69532245T2 (de) | 1994-09-26 | 2004-09-16 | Shionogi & Co., Ltd. | Imidazolderivat |
-
2002
- 2002-01-11 KR KR1020037010036A patent/KR100567706B1/ko not_active Expired - Fee Related
- 2002-01-11 PL PL02363321A patent/PL363321A1/xx not_active Application Discontinuation
- 2002-01-11 YU YU52303A patent/YU52303A/sh unknown
- 2002-01-11 EP EP02737611A patent/EP1377568A1/en not_active Withdrawn
- 2002-01-11 BR BR0206806-0A patent/BR0206806A/pt not_active IP Right Cessation
- 2002-01-11 MX MXPA03005403A patent/MXPA03005403A/es not_active Application Discontinuation
- 2002-01-11 WO PCT/IB2002/000082 patent/WO2002060893A1/en not_active Ceased
- 2002-01-11 RU RU2003123791/04A patent/RU2256657C2/ru not_active IP Right Cessation
- 2002-01-11 JP JP2002561042A patent/JP2004518687A/ja active Pending
- 2002-01-11 CZ CZ20032001A patent/CZ20032001A3/cs unknown
- 2002-01-11 CN CNB028042816A patent/CN1243748C/zh not_active Expired - Fee Related
- 2002-01-11 CA CA002433364A patent/CA2433364A1/en not_active Abandoned
- 2002-01-11 IL IL15636302A patent/IL156363A0/xx unknown
- 2002-01-11 HU HU0303028A patent/HUP0303028A3/hu unknown
- 2002-01-25 TW TW091101284A patent/TWI228507B/zh not_active IP Right Cessation
- 2002-01-25 US US10/056,268 patent/US6613908B2/en not_active Expired - Fee Related
- 2002-01-29 AR ARP020100312A patent/AR032419A1/es unknown
-
2003
- 2003-06-17 ZA ZA200304687A patent/ZA200304687B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0303028A3 (en) | 2005-10-28 |
| CN1243748C (zh) | 2006-03-01 |
| CN1489584A (zh) | 2004-04-14 |
| PL363321A1 (en) | 2004-11-15 |
| CZ20032001A3 (en) | 2004-06-16 |
| IL156363A0 (en) | 2004-01-04 |
| HUP0303028A2 (hu) | 2003-12-29 |
| BR0206806A (pt) | 2004-02-03 |
| US6613908B2 (en) | 2003-09-02 |
| US20020103378A1 (en) | 2002-08-01 |
| AR032419A1 (es) | 2003-11-05 |
| KR100567706B1 (ko) | 2006-04-05 |
| WO2002060893A1 (en) | 2002-08-08 |
| KR20030069227A (ko) | 2003-08-25 |
| RU2256657C2 (ru) | 2005-07-20 |
| MXPA03005403A (es) | 2003-09-25 |
| HK1060573A1 (en) | 2004-08-13 |
| YU52303A (sh) | 2006-05-25 |
| EP1377568A1 (en) | 2004-01-07 |
| CA2433364A1 (en) | 2002-08-08 |
| TWI228507B (en) | 2005-03-01 |
| ZA200304687B (en) | 2004-08-10 |
| JP2004518687A (ja) | 2004-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20070112 |