ATE393158T1 - Herstellung eines trans- calanolidketonzwischenprodukts und chirale trennung von calanolidalkoholen, die razemisches calanolid a liefert - Google Patents
Herstellung eines trans- calanolidketonzwischenprodukts und chirale trennung von calanolidalkoholen, die razemisches calanolid a liefertInfo
- Publication number
- ATE393158T1 ATE393158T1 AT04705591T AT04705591T ATE393158T1 AT E393158 T1 ATE393158 T1 AT E393158T1 AT 04705591 T AT04705591 T AT 04705591T AT 04705591 T AT04705591 T AT 04705591T AT E393158 T1 ATE393158 T1 AT E393158T1
- Authority
- AT
- Austria
- Prior art keywords
- calanolide
- trans
- preparation
- chiral separation
- ketone intermediate
- Prior art date
Links
- NIDRYBLTWYFCFV-FMTVUPSXSA-N (+)-calanolide A Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-FMTVUPSXSA-N 0.000 title abstract 3
- -1 CALANOLIDE ALCOHOLS Chemical class 0.000 title 1
- 229930184135 calanolide Natural products 0.000 title 1
- 238000000926 separation method Methods 0.000 title 1
- NIDRYBLTWYFCFV-SEDUGSJDSA-N (+)-calanolide b Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-SEDUGSJDSA-N 0.000 abstract 4
- NIDRYBLTWYFCFV-UHFFFAOYSA-N calanolide F Natural products C1=CC(C)(C)OC2=C1C(OC(C)C(C)C1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-UHFFFAOYSA-N 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 3
- NIDRYBLTWYFCFV-IUUKEHGRSA-N Calanolide A Natural products C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-IUUKEHGRSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/369,984 US6777562B1 (en) | 2003-02-19 | 2003-02-19 | Preparation of a trans-calanolide ketone intermediate and chiral separation of calanolide alcohols to give racemic calanolide A |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE393158T1 true ATE393158T1 (de) | 2008-05-15 |
Family
ID=32850367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT04705591T ATE393158T1 (de) | 2003-02-19 | 2004-01-27 | Herstellung eines trans- calanolidketonzwischenprodukts und chirale trennung von calanolidalkoholen, die razemisches calanolid a liefert |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6777562B1 (de) |
| EP (1) | EP1597263B1 (de) |
| JP (2) | JP4719830B2 (de) |
| CN (2) | CN101255166B (de) |
| AT (1) | ATE393158T1 (de) |
| DE (1) | DE602004013282T2 (de) |
| WO (1) | WO2004074294A1 (de) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5489697A (en) * | 1994-08-03 | 1996-02-06 | Medichem Research, Inc. | Method for the preparation of (+)-calanolide A and intermediates thereof |
| US6277879B1 (en) | 1994-08-03 | 2001-08-21 | Sarawak Medichem Pharmaceuticals, Inc. | Calanolide analogues and methods of their use |
| AU4491800A (en) * | 1999-04-26 | 2000-11-10 | Sarawak Medichem Pharmaceuticals, Inc. | Methods for preparing antiviral calanolide compounds |
| JP2002193969A (ja) * | 2000-12-23 | 2002-07-10 | Japan Science & Technology Corp | クロマノン環化合物の不斉合成方法とカロフィラムクマリン化合物の合成方法 |
-
2003
- 2003-02-19 US US10/369,984 patent/US6777562B1/en not_active Expired - Fee Related
-
2004
- 2004-01-27 CN CN2007101418753A patent/CN101255166B/zh not_active Expired - Fee Related
- 2004-01-27 WO PCT/US2004/002068 patent/WO2004074294A1/en not_active Ceased
- 2004-01-27 EP EP04705591A patent/EP1597263B1/de not_active Expired - Lifetime
- 2004-01-27 CN CN2004800074565A patent/CN1761669B/zh not_active Expired - Fee Related
- 2004-01-27 JP JP2006503009A patent/JP4719830B2/ja not_active Expired - Fee Related
- 2004-01-27 AT AT04705591T patent/ATE393158T1/de not_active IP Right Cessation
- 2004-01-27 DE DE602004013282T patent/DE602004013282T2/de not_active Expired - Lifetime
-
2010
- 2010-11-10 JP JP2010251696A patent/JP2011026353A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP4719830B2 (ja) | 2011-07-06 |
| JP2006518735A (ja) | 2006-08-17 |
| DE602004013282T2 (de) | 2009-07-16 |
| CN1761669A (zh) | 2006-04-19 |
| EP1597263A1 (de) | 2005-11-23 |
| CN1761669B (zh) | 2010-05-26 |
| WO2004074294A1 (en) | 2004-09-02 |
| JP2011026353A (ja) | 2011-02-10 |
| EP1597263B1 (de) | 2008-04-23 |
| CN101255166A (zh) | 2008-09-03 |
| DE602004013282D1 (de) | 2008-06-05 |
| US6777562B1 (en) | 2004-08-17 |
| CN101255166B (zh) | 2011-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |