ATE282033T1 - Synthese von beta-lapachone und entsprechender zwischenprodukte - Google Patents

Synthese von beta-lapachone und entsprechender zwischenprodukte

Info

Publication number: ATE282033T1
Authority: AT; Austria
Prior art keywords: lapachone; beta; synthesis; intermediate products; corresponding intermediate
Prior art date: 2001-01-25

Application number

AT02707586T

Other languages

English (en)

Inventor

Zhiwei Jiang

Jane Hogeland

Original Assignee

Arqule Inc

Priority date (The priority date 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 date listed.)

2001-01-25

Filing date

2002-01-23

Publication date

2004-11-15

2002-01-23 Application filed by Arqule Inc filed Critical Arqule Inc

2004-11-15 Application granted granted Critical

2004-11-15 Publication of ATE282033T1 publication Critical patent/ATE282033T1/de

Links

QZPQTZZNNJUOLS-UHFFFAOYSA-N beta-lapachone Chemical compound C12=CC=CC=C2C(=O)C(=O)C2=C1OC(C)(C)CC2 QZPQTZZNNJUOLS-UHFFFAOYSA-N 0.000 title abstract 12
230000015572 biosynthetic process Effects 0.000 title 1
239000013067 intermediate product Substances 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1
238000000034 method Methods 0.000 abstract 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
MEPSBMMZQBMKHM-UHFFFAOYSA-N Lomatiol Natural products CC(=C/CC1=C(O)C(=O)c2ccccc2C1=O)CO MEPSBMMZQBMKHM-UHFFFAOYSA-N 0.000 abstract 2
CIEYTVIYYGTCCI-UHFFFAOYSA-N SJ000286565 Natural products C1=CC=C2C(=O)C(CC=C(C)C)=C(O)C(=O)C2=C1 CIEYTVIYYGTCCI-UHFFFAOYSA-N 0.000 abstract 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
KNOSIOWNDGUGFJ-UHFFFAOYSA-N hydroxysesamone Natural products C1=CC(O)=C2C(=O)C(CC=C(C)C)=C(O)C(=O)C2=C1O KNOSIOWNDGUGFJ-UHFFFAOYSA-N 0.000 abstract 2
CWPGNVFCJOPXFB-UHFFFAOYSA-N lapachol Chemical compound C1=CC=C2C(=O)C(=O)C(CC=C(C)C)=C(O)C2=C1 CWPGNVFCJOPXFB-UHFFFAOYSA-N 0.000 abstract 2
SIUGQQMOYSVTAT-UHFFFAOYSA-N lapachol Natural products CC(=CCC1C(O)C(=O)c2ccccc2C1=O)C SIUGQQMOYSVTAT-UHFFFAOYSA-N 0.000 abstract 2
206010028980 Neoplasm Diseases 0.000 abstract 1
230000000118 anti-neoplastic effect Effects 0.000 abstract 1
201000011510 cancer Diseases 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
238000001953 recrystallisation Methods 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
230000002194 synthesizing effect Effects 0.000 abstract 1

Classifications

- 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
- C07D311/78—Ring systems having three or more relevant rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyrane Compounds (AREA)
Steroid Compounds (AREA)
Catalysts (AREA)

AT02707586T 2001-01-25 2002-01-23 Synthese von beta-lapachone und entsprechender zwischenprodukte ATE282033T1 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US26411601P	2001-01-25	2001-01-25
US09/957,260 US6458974B1 (en)	2001-01-25	2001-09-19	Synthesis of β-lapachone and its intermediates
PCT/US2002/002359 WO2002059103A1 (en)	2001-01-25	2002-01-23	Synthesis of beta-lapachone and its intermediates

Publications (1)

Publication Number	Publication Date
ATE282033T1 true ATE282033T1 (de)	2004-11-15

Family

ID=26950263

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT02707586T ATE282033T1 (de)	2001-01-25	2002-01-23	Synthese von beta-lapachone und entsprechender zwischenprodukte

Country Status (9)

Country	Link
US (1)	US6458974B1 (de)
EP (1)	EP1363896B1 (de)
JP (1)	JP4434585B2 (de)
AT (1)	ATE282033T1 (de)
AU (1)	AU2002241985B2 (de)
CA (1)	CA2436125C (de)
DE (1)	DE60201890T2 (de)
ES (1)	ES2230471T3 (de)
WO (1)	WO2002059103A1 (de)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050222246A1 (en) *	1999-04-14	2005-10-06	Li Chiang J	Beta-lapachone is a broad spectrum anti-cancer agent
US20050192360A1 (en) *	1999-04-14	2005-09-01	Li Chiang J.	Method of treatment of pancreatic cancer
US20040209942A1 (en) *	2002-07-17	2004-10-21	Li Chiang J.	Activated checkpoint therapy and methods of use thereof
US20050197405A1 (en) *	2000-11-07	2005-09-08	Li Chiang J.	Treatment of hematologic tumors and cancers with beta-lapachone, a broad spectrum anti-cancer agent
US6816571B2 (en) *	2002-02-06	2004-11-09	L-3 Communications Security And Detection Systems Corporation Delaware	Method and apparatus for transmitting information about a target object between a prescanner and a CT scanner
US7361691B2 (en) *	2002-12-02	2008-04-22	Arqule, Inc.	Method of treating cancers using β-lapachone or analogs or derivatives thereof
US20050187288A1 (en) *	2004-02-20	2005-08-25	Chiang Li	Beta-lapachone and methods of treating cancer
CA2555950A1 (en)	2004-02-20	2005-09-09	Arqule, Inc.	Use of beta-lapachone for the treatment of pancreatic cancer
WO2005082355A2 (en)	2004-02-20	2005-09-09	Arqule, Inc.	Use of beta-lapachone for treatment of colon cancer
CA2556823A1 (en)	2004-02-20	2005-09-09	Arqule, Inc.	Use of beta-lapachone for the treatment of lung cancer
US20050192247A1 (en) *	2004-02-23	2005-09-01	Li Chiang J.	Method of treating cancers
WO2006020719A2 (en) *	2004-08-11	2006-02-23	Arqule, Inc.	Aminoacid conjugates of beta - lapachone for tumor targeting
US8614228B2 (en) *	2004-08-11	2013-12-24	Arqule, Inc.	Quinone prodrug compositions and methods of use
WO2006078503A2 (en)	2005-01-07	2006-07-27	Arqule, Inc.	Compositions for modulation of parp and methods for screening for same
BRPI0810717A2 (pt) *	2007-04-30	2016-05-24	Arqule Inc	sulfonato hidroxi de composto de quinona e seus usos
CN103239430B (zh) *	2013-05-08	2015-01-07	首都医科大学	拉帕醇在制备预防和/或治疗恶性胶质瘤的产品中的应用
CN105294638A (zh) *	2015-10-30	2016-02-03	成都科创佳思科技有限公司	一种去氢α-拉帕醌的催化合成方法
US11013673B2 (en)	2016-11-03	2021-05-25	Repairogen Corp.	Cosmetic compositions containing quinones and their topical use on skin and hair
US10780034B2 (en)	2016-11-03	2020-09-22	Repairogen Corp.	Cosmetic compositions containing quinones and their topical use on skin and hair
WO2019213494A1 (en)	2018-05-03	2019-11-07	Repairogen Corp	Cosmetic compositions containing quinones and their topical use on skin and hair
CN113372298B (zh) *	2021-05-21	2022-04-19	温州医科大学	一种2-碘-3-胺基萘醌化合物的制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5824700A (en) *	1996-02-20	1998-10-20	Wisconsin Alumni Research Foundation	Ortho-quinone derivatives novel synthesis therefor and their use in the inhibition of neoplastic cell growth

2001
- 2001-09-19 US US09/957,260 patent/US6458974B1/en not_active Expired - Lifetime
2002
- 2002-01-23 AT AT02707586T patent/ATE282033T1/de active
- 2002-01-23 JP JP2002559405A patent/JP4434585B2/ja not_active Expired - Fee Related
- 2002-01-23 DE DE60201890T patent/DE60201890T2/de not_active Expired - Lifetime
- 2002-01-23 WO PCT/US2002/002359 patent/WO2002059103A1/en not_active Ceased
- 2002-01-23 CA CA002436125A patent/CA2436125C/en not_active Expired - Fee Related
- 2002-01-23 EP EP02707586A patent/EP1363896B1/de not_active Expired - Lifetime
- 2002-01-23 ES ES02707586T patent/ES2230471T3/es not_active Expired - Lifetime
- 2002-01-23 AU AU2002241985A patent/AU2002241985B2/en not_active Ceased

Also Published As

Publication number	Publication date
DE60201890T2 (de)	2005-12-08
US6458974B1 (en)	2002-10-01
WO2002059103A1 (en)	2002-08-01
EP1363896B1 (de)	2004-11-10
CA2436125C (en)	2009-03-31
JP2004520378A (ja)	2004-07-08
JP4434585B2 (ja)	2010-03-17
EP1363896A1 (de)	2003-11-26
CA2436125A1 (en)	2002-08-01
DE60201890D1 (de)	2004-12-16
US20020137952A1 (en)	2002-09-26
WO2002059103A9 (en)	2003-01-03
ES2230471T3 (es)	2005-05-01
AU2002241985B2 (en)	2006-01-19

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