MX9700782A - Metodo para la preparacion de la (+)-calanolida a y sus productos intermedios. - Google Patents
Metodo para la preparacion de la (+)-calanolida a y sus productos intermedios.Info
- Publication number
- MX9700782A MX9700782A MX9700782A MX9700782A MX9700782A MX 9700782 A MX9700782 A MX 9700782A MX 9700782 A MX9700782 A MX 9700782A MX 9700782 A MX9700782 A MX 9700782A MX 9700782 A MX9700782 A MX 9700782A
- Authority
- MX
- Mexico
- Prior art keywords
- calanolide
- chromene
- preparing
- disclosed
- acetaldehyde
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Se da a conocer un método para preparar una (+)-calanolida A, un inhibidor potente de la transcriptasa inversa del HIV, a partir del cromeno (4). También se suministran productos intermedios utiles para preparar la (+)- calanolida A y sus derivados. De acuerdo con el método descrito, el producto intermedio de cromeno (4) se hace reaccionar con el acetaldehído-dietil-acetal o el peraldehído, en la presencia de un catalizador ácido, con calentamiento, o una reaccion de dos etapas, que incluye una reaccion del aldol con el acetaldehído y la ciclizacion o bajo condiciones ácidas o bajo las condiciones neutrales de Mitsunobu, para producir la cromanona (7). La reduccion de la cromanona (7) con el borohidruro de sodio, en la presencia del tricloruro de cerio, produjo la (+)-calanolida A. También se da a conocer un método para resolver la (+)-calanolida A en sus formas activas opticamente, por medio de un sistema de cromatografía HPLC quiral o por la acilacion enzimática e hidrolisis. Finalmente, se suministra un método para tratar o prevenir infecciones virales, con el uso de la (+)-calanolida o la (-)-calanolida.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/285,655 US5489697A (en) | 1994-08-03 | 1994-08-03 | Method for the preparation of (+)-calanolide A and intermediates thereof |
| US285655 | 1994-08-03 | ||
| US285,655 | 1994-08-03 | ||
| PCT/US1995/009804 WO1996004263A1 (en) | 1994-08-03 | 1995-08-02 | Method for the preparation of (±)-calanolide a and intermediates thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX9700782A true MX9700782A (es) | 1997-09-30 |
| MXPA97000782A MXPA97000782A (es) | 1998-07-03 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| EP0775130A1 (en) | 1997-05-28 |
| CA2196656C (en) | 2010-03-23 |
| ATE239008T1 (de) | 2003-05-15 |
| WO1996004263A1 (en) | 1996-02-15 |
| AU3274695A (en) | 1996-03-04 |
| EP1054007A3 (en) | 2000-11-29 |
| JP3043813B2 (ja) | 2000-05-22 |
| JPH09512829A (ja) | 1997-12-22 |
| DE69530592D1 (de) | 2003-06-05 |
| EP0775130B1 (en) | 2003-05-02 |
| EP1308448A1 (en) | 2003-05-07 |
| EP1054007A2 (en) | 2000-11-22 |
| AU704247B2 (en) | 1999-04-15 |
| US5489697A (en) | 1996-02-06 |
| DE69530592T2 (de) | 2004-03-18 |
| CA2196656A1 (en) | 1996-02-15 |
| MY118279A (en) | 2004-09-30 |
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