PE20130043A1 - Proceso para preparar voriconazol utilizando nuevos intermediarios - Google Patents
Proceso para preparar voriconazol utilizando nuevos intermediariosInfo
- Publication number
- PE20130043A1 PE20130043A1 PE2012001163A PE2012001163A PE20130043A1 PE 20130043 A1 PE20130043 A1 PE 20130043A1 PE 2012001163 A PE2012001163 A PE 2012001163A PE 2012001163 A PE2012001163 A PE 2012001163A PE 20130043 A1 PE20130043 A1 PE 20130043A1
- Authority
- PE
- Peru
- Prior art keywords
- formula
- compound
- iii
- voriconazole
- substituted
- Prior art date
Links
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 title abstract 3
- 229960004740 voriconazole Drugs 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YXFVVABEGXRONW-CNRUNOGKSA-N tritiomethylbenzene Chemical compound [3H]CC1=CC=CC=C1 YXFVVABEGXRONW-CNRUNOGKSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE REFIERE A UN PROCESO PARA PREPARAR VORICONAZOL DE FORMULA (I) QUE COMPRENDE: 1) UNA REACCION DE ACOPLAMIENTO DEL TIPO REFORMATSKY ENTRE UN COMPUESTO DERIVADO DE CETONA DE FORMULA (IV) Y UN COMPUESTO DERIVADO DE PIRIMIDINA DE FORMULA (V) PARA OBTENER UN COMPUESTO DE FORMULA (III), A UNA TEMPERATURA ENTRE -15 ºC A 0 ºC; 2) RETIRAR LOS SUSTITUYENTES X1, X2 Y OSO2R DEL COMPUESTO DE FORMULA (III) PARA OBTENER VORICONAZOL RACEMICO DE FORMULA (II), A CONDICION DE QUE NO SE ELIMINEN X1 NI X2 CUANDO AMBOS SON H; USANDO Pd/C, NIQUEL RANEY O ZINC COMO CATALIZADOR, CON UNA CANTIDAD DE Pd/C DE 2 A 30 % EN PESO CON BASE EN LA CANTIDAD DEL COMPUESTO DE FORMULA (III); COMO SOLVENTE, TOLUENO, BENCENO, XILENO O UNA MEZCLA DE ELLOS, Y COMO DONADOR DE HIDROGENO, FORMIATO DE AMONIO O H; Y 3) SEPARAR LOS ISOMEROS DEL COMPUESTO DE FORMULA (II) CON UN ACIDO OPTICAMENTE ACTIVO; X1 Y X2 SON INDEPENDIENTEMENTE H O HALOGENO, R ES ALQUILO C1-4 O FENILO NO SUSTITUIDO O SUSTITUIDO POR NITRO, OXO ENTRE OTROS
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020100010467A KR100971371B1 (ko) | 2010-02-04 | 2010-02-04 | 신규한 중간체를 이용한 보리코나졸의 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20130043A1 true PE20130043A1 (es) | 2013-02-04 |
Family
ID=42645839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2012001163A PE20130043A1 (es) | 2010-02-04 | 2011-02-01 | Proceso para preparar voriconazol utilizando nuevos intermediarios |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8575344B2 (es) |
| EP (1) | EP2531499B1 (es) |
| JP (1) | JP5553911B2 (es) |
| KR (1) | KR100971371B1 (es) |
| BR (1) | BR112012019620A2 (es) |
| ES (1) | ES2518892T3 (es) |
| MX (1) | MX2012008152A (es) |
| PE (1) | PE20130043A1 (es) |
| WO (1) | WO2011096697A2 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101435741B1 (ko) * | 2013-01-17 | 2014-08-29 | (주) 에프엔지리서치 | 신규한 보리코나졸 중간체 및 이를 이용한 보리코나졸의 제조 방법 |
| KR101709543B1 (ko) * | 2014-12-09 | 2017-02-23 | (주) 에프엔지리서치 | 신규한 보리코나졸 중간체 및 이를 이용한 보리코나졸의 제조 방법 |
| CN114829354A (zh) * | 2019-12-24 | 2022-07-29 | 刘杰 | 一种伏立康唑对映异构体的回收方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0069442B1 (en) | 1981-06-06 | 1985-02-20 | Pfizer Limited | Antifungal agents, processes for their preparation, and pharmaceutical compositions containing them |
| GB9002375D0 (en) * | 1990-02-02 | 1990-04-04 | Pfizer Ltd | Triazole antifungal agents |
| GB9516121D0 (en) | 1995-08-05 | 1995-10-04 | Pfizer Ltd | Organometallic addition to ketones |
| EP1899327A1 (en) | 2005-06-30 | 2008-03-19 | MSN Laboratories Limited | Improved process for the preparation of 2r, 3s-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl) butan-2-ol (voriconazole) |
| CA2640922A1 (en) * | 2006-02-01 | 2007-11-22 | Medichem, S.A. | Process for preparing voriconazole, new polymorphic form of intermediate thereof, and uses thereof |
| KR100889937B1 (ko) * | 2007-08-06 | 2009-03-20 | 한미약품 주식회사 | 보리코나졸의 제조방법 |
| GB2452049A (en) | 2007-08-21 | 2009-02-25 | Alpharma Aps | Process for the preparation of voriconazole |
| WO2009084029A2 (en) | 2007-12-03 | 2009-07-09 | Neuland Laboratories Ltd | Improved process for the preparation of (2r,3s)-2-(2,4- difluqrophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl) butan-2-ol |
-
2010
- 2010-02-04 KR KR1020100010467A patent/KR100971371B1/ko not_active Expired - Fee Related
-
2011
- 2011-02-01 WO PCT/KR2011/000689 patent/WO2011096697A2/en not_active Ceased
- 2011-02-01 US US13/577,055 patent/US8575344B2/en not_active Expired - Fee Related
- 2011-02-01 MX MX2012008152A patent/MX2012008152A/es active IP Right Grant
- 2011-02-01 PE PE2012001163A patent/PE20130043A1/es active IP Right Grant
- 2011-02-01 ES ES11739993.1T patent/ES2518892T3/es active Active
- 2011-02-01 BR BR112012019620A patent/BR112012019620A2/pt not_active Application Discontinuation
- 2011-02-01 JP JP2012551915A patent/JP5553911B2/ja not_active Expired - Fee Related
- 2011-02-01 EP EP11739993.1A patent/EP2531499B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012019620A2 (pt) | 2022-05-10 |
| JP2013518876A (ja) | 2013-05-23 |
| EP2531499A2 (en) | 2012-12-12 |
| US20130005973A1 (en) | 2013-01-03 |
| WO2011096697A2 (en) | 2011-08-11 |
| WO2011096697A3 (en) | 2011-12-15 |
| KR100971371B1 (ko) | 2010-07-20 |
| ES2518892T3 (es) | 2014-11-05 |
| US8575344B2 (en) | 2013-11-05 |
| MX2012008152A (es) | 2012-08-23 |
| JP5553911B2 (ja) | 2014-07-23 |
| EP2531499B1 (en) | 2014-07-23 |
| EP2531499A4 (en) | 2013-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration |