JP2001515895A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2001515895A5 JP2001515895A5 JP2000510727A JP2000510727A JP2001515895A5 JP 2001515895 A5 JP2001515895 A5 JP 2001515895A5 JP 2000510727 A JP2000510727 A JP 2000510727A JP 2000510727 A JP2000510727 A JP 2000510727A JP 2001515895 A5 JP2001515895 A5 JP 2001515895A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- cvi
- formula
- hydroxylactone
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002253 acid Substances 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- QUCVMTKZXVHNNT-CQSZACIVSA-N (3r)-3-hydroxy-3-(2-phenylethyl)hexanoic acid Chemical compound CCC[C@](O)(CC(O)=O)CCC1=CC=CC=C1 QUCVMTKZXVHNNT-CQSZACIVSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- -1 3-nitrophenyl Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- DLNKOYKMWOXYQA-VXNVDRBHSA-N (+)-norephedrine Chemical compound C[C@@H](N)[C@@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-VXNVDRBHSA-N 0.000 description 1
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
- IJXJGQCXFSSHNL-MRVPVSSYSA-N (2s)-2-amino-2-phenylethanol Chemical compound OC[C@@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-MRVPVSSYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- IJXJGQCXFSSHNL-UHFFFAOYSA-N 2-amino-2-phenylethanol Chemical compound OCC(N)C1=CC=CC=C1 IJXJGQCXFSSHNL-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5861897P | 1997-09-11 | 1997-09-11 | |
| US60/058,618 | 1997-09-11 | ||
| PCT/US1998/017993 WO1999012919A1 (en) | 1997-09-11 | 1998-09-03 | Process to produce 4-hydroxy-2-oxo-pyrane derivates useful as protease inhibitors |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009022289A Division JP5016621B2 (ja) | 1997-09-11 | 2009-02-03 | プロテアーゼインヒビターとして有用な４−ヒドロキシ−２−オキソ−ピラン誘導体の製法 |
| JP2009280318A Division JP5266194B2 (ja) | 1997-09-11 | 2009-12-10 | プロテアーゼインヒビターとして有用な４−ヒドロキシ−２−オキソ−ピラン誘導体の製法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001515895A JP2001515895A (ja) | 2001-09-25 |
| JP2001515895A5 true JP2001515895A5 (enExample) | 2006-01-05 |
| JP4462760B2 JP4462760B2 (ja) | 2010-05-12 |
Family
ID=22017924
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000510727A Expired - Lifetime JP4462760B2 (ja) | 1997-09-11 | 1998-09-03 | プロテアーゼインヒビターとして有用な４−ヒドロキシ−２−オキソ−ピラン誘導体の製法 |
| JP2009022289A Expired - Lifetime JP5016621B2 (ja) | 1997-09-11 | 2009-02-03 | プロテアーゼインヒビターとして有用な４−ヒドロキシ−２−オキソ−ピラン誘導体の製法 |
| JP2009280318A Expired - Lifetime JP5266194B2 (ja) | 1997-09-11 | 2009-12-10 | プロテアーゼインヒビターとして有用な４−ヒドロキシ−２−オキソ−ピラン誘導体の製法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009022289A Expired - Lifetime JP5016621B2 (ja) | 1997-09-11 | 2009-02-03 | プロテアーゼインヒビターとして有用な４−ヒドロキシ−２−オキソ−ピラン誘導体の製法 |
| JP2009280318A Expired - Lifetime JP5266194B2 (ja) | 1997-09-11 | 2009-12-10 | プロテアーゼインヒビターとして有用な４−ヒドロキシ−２−オキソ−ピラン誘導体の製法 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6077963A (enExample) |
| EP (1) | EP1015441B1 (enExample) |
| JP (3) | JP4462760B2 (enExample) |
| KR (1) | KR100569771B1 (enExample) |
| CN (3) | CN1284763C (enExample) |
| AT (1) | ATE266654T1 (enExample) |
| CA (1) | CA2300204C (enExample) |
| CZ (1) | CZ298847B6 (enExample) |
| DE (1) | DE69823844T2 (enExample) |
| DK (1) | DK1015441T3 (enExample) |
| ES (1) | ES2221199T3 (enExample) |
| FI (1) | FI120973B (enExample) |
| HU (1) | HU228986B1 (enExample) |
| NO (1) | NO321835B1 (enExample) |
| NZ (1) | NZ503338A (enExample) |
| PL (1) | PL193240B1 (enExample) |
| PT (1) | PT1015441E (enExample) |
| RU (2) | RU2223958C2 (enExample) |
| SK (1) | SK284974B6 (enExample) |
| WO (1) | WO1999012919A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1161427B1 (en) * | 1999-03-18 | 2002-10-23 | PHARMACIA & UPJOHN COMPANY | Improved process for asymmetric hydrogenation |
| US6552204B1 (en) * | 2000-02-04 | 2003-04-22 | Roche Colorado Corporation | Synthesis of 3,6-dialkyl-5,6-dihydro-4-hydroxy-pyran-2-one |
| DE10108470A1 (de) * | 2001-02-22 | 2002-09-05 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung optisch aktiver Dihydropyrone |
| US6500963B2 (en) | 2001-02-22 | 2002-12-31 | Boehringer Ingelheim Pharma Kg | Process for preparing optically active dihydropyrones |
| US6987123B2 (en) | 2001-07-26 | 2006-01-17 | Cadila Healthcare Limited | Heterocyclic compounds, their preparation, pharmaceutical compositions containing them and their use in medicine |
| AU2002344438B2 (en) | 2002-02-07 | 2008-09-11 | Sumitomo Chemical Company, Limited | Process for producing (R)-3-hydroxy-3-(2-phenylethyl)hexanoic acid and its intermediate |
| DE10313118A1 (de) | 2003-03-24 | 2004-10-07 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Enantioselektive Hydrierung von Intermediaten bei der Tipranavir-Synthese |
| US7512945B2 (en) * | 2003-12-29 | 2009-03-31 | Intel Corporation | Method and apparatus for scheduling the processing of commands for execution by cryptographic algorithm cores in a programmable network processor |
| CN100448836C (zh) * | 2005-06-03 | 2009-01-07 | 浙江中贝化工有限公司 | 一种抗艾滋病药物关键中间体的制备方法 |
| BRPI0615016A2 (pt) * | 2005-08-24 | 2011-05-03 | Pfizer | compostos inibidores de hcv polimerase, métodos para prepará-los e forma cristalina |
| CN103996798B (zh) * | 2007-11-30 | 2017-09-08 | 株式会社半导体能源研究所 | 发光元件、发光装置以及电子装置 |
| US8853393B2 (en) * | 2011-07-29 | 2014-10-07 | Anhui New Star Pharmaceutical Development Co., Ltd. | Intermediate for preparing tapentadol or analogues thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1355668A (fr) * | 1963-02-05 | 1964-03-20 | Moteur rotatif à combustion interne perfectionné | |
| FR1355667A (fr) * | 1963-02-05 | 1964-03-20 | Meci Materiel Elect Contr | Gaine tubulaire pour électrode servant à la mesure du ph |
| FR2096877B1 (enExample) * | 1970-07-09 | 1973-08-10 | Hexachimie | |
| JPH0665657B2 (ja) * | 1984-11-08 | 1994-08-24 | 日本化薬株式会社 | 光学活性マンデル酸の製法 |
| JPH072677B2 (ja) * | 1988-02-19 | 1995-01-18 | 株式会社クラレ | （±）―２―ヒドロキシ―４―フェニルブタン酸の光学分割法 |
| JPH01221345A (ja) * | 1988-02-27 | 1989-09-04 | Ajinomoto Co Inc | マンデル酸誘導体の光学分割方法 |
| JP3084577B2 (ja) * | 1991-09-27 | 2000-09-04 | 山川薬品工業株式会社 | 光学活性なアトロラクチン酸の製造方法および製造の中間体 |
| JP3178086B2 (ja) * | 1992-06-17 | 2001-06-18 | 山川薬品工業株式会社 | 光学活性α−メチルベンジルアミンの製造方法 |
| ZA938019B (en) * | 1992-11-13 | 1995-04-28 | Upjohn Co | Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating HIV and other retroviruses |
| PT1142887E (pt) * | 1993-11-19 | 2004-08-31 | Parke Davis & Co | Derivados de 5,6-di-hidropirona como inibidores de protease e agentes antivirais |
| IL129871A (en) * | 1994-05-06 | 2003-11-23 | Pharmacia & Upjohn Inc | Process for preparing 4-phenyl-substituted octanoyl-oxazolidin-2-one intermediates that are useful for preparing pyran-2-ones useful for treating retroviral infections |
| RU2074169C1 (ru) * | 1995-05-10 | 1997-02-27 | Акционерное общество открытого типа "Химпром" | Способ получения этилового эфира п-нитробензойной кислоты |
-
1998
- 1998-09-03 CN CNB031594735A patent/CN1284763C/zh not_active Expired - Lifetime
- 1998-09-03 PL PL339138A patent/PL193240B1/pl unknown
- 1998-09-03 KR KR1020007002546A patent/KR100569771B1/ko not_active Expired - Lifetime
- 1998-09-03 HU HU0003593A patent/HU228986B1/hu unknown
- 1998-09-03 EP EP98945806A patent/EP1015441B1/en not_active Expired - Lifetime
- 1998-09-03 ES ES98945806T patent/ES2221199T3/es not_active Expired - Lifetime
- 1998-09-03 CN CNB988087111A patent/CN1298714C/zh not_active Expired - Lifetime
- 1998-09-03 DE DE69823844T patent/DE69823844T2/de not_active Expired - Lifetime
- 1998-09-03 NZ NZ503338A patent/NZ503338A/en not_active IP Right Cessation
- 1998-09-03 CZ CZ20000804A patent/CZ298847B6/cs not_active IP Right Cessation
- 1998-09-03 WO PCT/US1998/017993 patent/WO1999012919A1/en not_active Ceased
- 1998-09-03 DK DK98945806T patent/DK1015441T3/da active
- 1998-09-03 PT PT98945806T patent/PT1015441E/pt unknown
- 1998-09-03 JP JP2000510727A patent/JP4462760B2/ja not_active Expired - Lifetime
- 1998-09-03 AT AT98945806T patent/ATE266654T1/de active
- 1998-09-03 CA CA002300204A patent/CA2300204C/en not_active Expired - Lifetime
- 1998-09-03 CN CNB2007100079776A patent/CN100471832C/zh not_active Expired - Lifetime
- 1998-09-03 RU RU2000109277/04A patent/RU2223958C2/ru active
- 1998-09-03 SK SK226-2000A patent/SK284974B6/sk not_active IP Right Cessation
- 1998-12-17 US US09/213,887 patent/US6077963A/en not_active Expired - Lifetime
-
2000
- 2000-02-28 US US09/514,087 patent/US6265604B1/en not_active Expired - Lifetime
- 2000-03-10 NO NO20001274A patent/NO321835B1/no not_active IP Right Cessation
- 2000-03-10 FI FI20000553A patent/FI120973B/fi not_active IP Right Cessation
-
2003
- 2003-10-21 RU RU2003131081/04A patent/RU2263106C2/ru active
-
2009
- 2009-02-03 JP JP2009022289A patent/JP5016621B2/ja not_active Expired - Lifetime
- 2009-12-10 JP JP2009280318A patent/JP5266194B2/ja not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5800834B2 (ja) | ハリコンドリンｂ類似体の合成において有用なフロ［３，２−ｂ］ピラン誘導体 | |
| JP2001515895A5 (enExample) | ||
| EP1200384B1 (de) | 2-alkyl-5-halogen-pent-4-encarbonsäuren und deren herstellung | |
| CN1113485A (zh) | 含取代的吡啶基二羟基庚烯酸或其盐的药物的制法 | |
| JP2012503621A5 (enExample) | ||
| JP2010532340A5 (enExample) | ||
| EP2785687A1 (en) | Process for preparation of (3r)-2,4-di-leaving group-3-methylbut-1-ene | |
| CS236484B2 (en) | Method of 9-fluorprostaglandine derivatives production | |
| WO2009125841A1 (ja) | ５－メチルウリジンを出発原料とするエチニルチミジン化合物の製造方法 | |
| RU2000109277A (ru) | Новый способ получения ингибитора протеазы | |
| JP2004529172A5 (enExample) | ||
| RU2223958C2 (ru) | Новый способ получения ингибитора протеазы | |
| DE69920906T2 (de) | Zwischenprodukte in der synthese von epothilonen und verfahren zu deren herstellung | |
| JP2008509896A (ja) | 保護化アミノチアゾールのフッ素化方法 | |
| JP2003055368A (ja) | ケミカルプロセス | |
| JP2006505567A5 (enExample) | ||
| KR20100102107A (ko) | β-뉴클레오시드의 새로운 합성 방법 | |
| DE69715417T2 (de) | Oxazolidinester | |
| DE10138347A1 (de) | Geschützte 3,5-Dihydroxy-2,2-dimethyl-valeronitrile für die Synthese von Epothilonen- und Derivaten und Verfahren zur Herstellung | |
| EP3360866B1 (en) | Mirabegron prodrugs | |
| JP7109056B2 (ja) | Ｓ－ｉｃａリボシルホモシステインの製造方法 | |
| Drag et al. | Synthesis of α1-(Cbz-aminoalkyl)-α2-(hydroxyalkyl) phosphinic esters | |
| FR2551436A1 (fr) | 16-fluoro-16,17-dideshydro-prostanoides, procede pour leur preparation, produits intermediaires de leur preparation et leurs utilisations therapeutiques, notamment dans les indications des prostaglandines naturelles | |
| CA2261591A1 (en) | Adenosine deaminase inhibitors | |
| DE10138348A1 (de) | Geschützte 3,5-Dihydroxy-2,2-dimethyl-valeroamide für die Synthese von Epothilonen und Derivaten und Verfahren zur Herstellung und die Verwendung |