ES2112151B1 - Nuevos compuestos homoquirales para la preparacion de ketoconazol, terconazol y antifungicos relacionados, procedimiento para su fabricacion y utilizacion de los mismos. - Google Patents
Nuevos compuestos homoquirales para la preparacion de ketoconazol, terconazol y antifungicos relacionados, procedimiento para su fabricacion y utilizacion de los mismos.Info
- Publication number
- ES2112151B1 ES2112151B1 ES9500553A ES9500553A ES2112151B1 ES 2112151 B1 ES2112151 B1 ES 2112151B1 ES 9500553 A ES9500553 A ES 9500553A ES 9500553 A ES9500553 A ES 9500553A ES 2112151 B1 ES2112151 B1 ES 2112151B1
- Authority
- ES
- Spain
- Prior art keywords
- compounds
- homoquiral
- preparation
- new
- theronazole
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title abstract 5
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 title abstract 2
- 229960004125 ketoconazole Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 229940121375 antifungal agent Drugs 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
NUEVOS COMPUESTOS HOMOQUIRALES PARA LA PREPARACION DE KETOCONAZOL, TERCONAZOL Y ANTIFUNGICOS RELACIONADOS, PROCEDIMIENTO PARA SU FABRICACION Y UTILIZACION DE LOS MISMOS. LA PRESENTE INVENCION SE REFIERE A NUEVOS COMPUESTOS HOMOQUIRALES QUE SON INTERMEDIOS EN LA PREPARACION DE DIVERSOS ANTIFUNGICOS AZOLICOS DE FORMULA V EN FORMA ENANTIOMERICAMENTE PURA, DONDE AR ES UN GRUPO FENILO O FENILO SUSTITUIDO, DE MODO QUE EL GRUPO FENILO SUSTITUIDO PUEDE CONTENER DE UNO A TRES SUSTITUYENTES, CADA UNO DE LOS CUALES INDEPENDIENTEMENTE PUEDE SER FLUOR, CLORO, BROMO, (C1-C4)-ALQUILO O (C1-C4)-ALQUILOXI; Y ES UNA AGRUPACION CH O UN ATOMO DE NITROGENO; Z ES UN GRUPO COCH3, CH(CH3)2 O DE IGUAL MODO LA PRESENTE INVENCION SE REFIERE A LOS PROPIOS COMPUESTOS (+)- TERCONAZOL Y (-)-TERCONAZOL. DICHOS COMPUESTOS PRESENTAN ACTIVIDAD ANTIFUNGICA Y ANTIBACTERIANA, PUDIENDO SER UTILIZADOS EN TERAPIA HUMANA Y EN VETERINARIA.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9500553A ES2112151B1 (es) | 1995-03-17 | 1995-03-17 | Nuevos compuestos homoquirales para la preparacion de ketoconazol, terconazol y antifungicos relacionados, procedimiento para su fabricacion y utilizacion de los mismos. |
| AU50039/96A AU5003996A (en) | 1995-03-17 | 1996-03-07 | Homochiral compounds for the preparation of ketoconazole, terconazole and related antifungal drugs |
| PCT/EP1996/000972 WO1996029325A1 (en) | 1995-03-17 | 1996-03-07 | Homochiral compounds for the preparation of ketoconazole, terconazole and related antifungal drugs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9500553A ES2112151B1 (es) | 1995-03-17 | 1995-03-17 | Nuevos compuestos homoquirales para la preparacion de ketoconazol, terconazol y antifungicos relacionados, procedimiento para su fabricacion y utilizacion de los mismos. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2112151A1 ES2112151A1 (es) | 1998-03-16 |
| ES2112151B1 true ES2112151B1 (es) | 1999-09-16 |
Family
ID=8289834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9500553A Expired - Lifetime ES2112151B1 (es) | 1995-03-17 | 1995-03-17 | Nuevos compuestos homoquirales para la preparacion de ketoconazol, terconazol y antifungicos relacionados, procedimiento para su fabricacion y utilizacion de los mismos. |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU5003996A (es) |
| ES (1) | ES2112151B1 (es) |
| WO (1) | WO1996029325A1 (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998021204A1 (en) | 1996-11-12 | 1998-05-22 | Sepracor, Inc. | 2r,4s,s,s- and 2s,4r,s,s-hydroxyitraconazole |
| CN1237174A (zh) * | 1996-11-12 | 1999-12-01 | 塞普拉科公司 | 2r,4s,s,r-和2s,4r,s,r-羟基伊曲康唑 |
| AU5251398A (en) * | 1996-11-12 | 1998-06-03 | Sepracor, Inc. | (2r,4s,r,r-) and (2s,4r,r,r-)hydroxyitraconazole |
| EP2803357B1 (en) | 2004-06-25 | 2020-11-18 | The Johns-Hopkins University | Angiogenesis inhibitors |
| MX2009012739A (es) * | 2007-05-25 | 2009-12-10 | Janssen Pharmaceutica Nv | Sintesis mejorada del metansulfonato(ester) de (2s-cis)-2-(bromometil)-2-(4-clorofenil)-1,3-dioxolan-4-metanol. |
| WO2010013510A1 (ja) * | 2008-08-01 | 2010-02-04 | ダイソー株式会社 | 光学活性化合物の製造方法 |
| EP3858357A1 (en) | 2020-01-28 | 2021-08-04 | Diaccurate | Use of azole compounds to stimulate the immune system and as inhibitors for s-pla2gib |
| WO2024105519A1 (en) * | 2022-11-14 | 2024-05-23 | Piramal Pharma Limited | A process for the preparation of levoketoconazole |
| CN116854657A (zh) * | 2023-07-04 | 2023-10-10 | 浙江东亚药业股份有限公司 | 一种酮康唑中间体顺式溴代酯的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3039087A1 (de) * | 1980-10-16 | 1982-05-19 | Hoechst Ag, 6000 Frankfurt | 1-(1,3-dioxolan-2-ylmethyl)-azole, ihre salze, verfahren zu ihrer herstellung und ihre verwendung |
| EP0052905B1 (en) * | 1980-11-24 | 1984-10-03 | Janssen Pharmaceutica N.V. | Novel (2-aryl-4-phenylthioalkyl-1,3-dioxolan-2-yl-methyl)azole derivatives |
| CA2117651C (en) * | 1992-03-18 | 2006-01-03 | Jan Heeres | Itraconazole and saperconazole stereoisomers |
| US5208331A (en) * | 1992-06-18 | 1993-05-04 | Syntex (U.S.A.) Inc. | Process for preparing 1,3-dioxolane derivatives |
| US5403937A (en) * | 1993-04-30 | 1995-04-04 | Schering Corporation | Process for preparing intermediates for the synthesis of antifungal agents |
-
1995
- 1995-03-17 ES ES9500553A patent/ES2112151B1/es not_active Expired - Lifetime
-
1996
- 1996-03-07 WO PCT/EP1996/000972 patent/WO1996029325A1/en not_active Ceased
- 1996-03-07 AU AU50039/96A patent/AU5003996A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO1996029325A1 (en) | 1996-09-26 |
| ES2112151A1 (es) | 1998-03-16 |
| AU5003996A (en) | 1996-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 19980316 Kind code of ref document: A1 Effective date: 19980316 |
|
| FA2A | Application withdrawn |
Effective date: 20001102 |