CN1545508B - 1,2,4-三噁茂烷抗疟药 - Google Patents

1,2,4-三噁茂烷抗疟药 Download PDF

Info

Publication number
CN1545508B
CN1545508B CN028164539A CN02816453A CN1545508B CN 1545508 B CN1545508 B CN 1545508B CN 028164539 A CN028164539 A CN 028164539A CN 02816453 A CN02816453 A CN 02816453A CN 1545508 B CN1545508 B CN 1545508B
Authority
CN
China
Prior art keywords
nmr
mmol
cdcl
trioxa
spiro
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
Application number
CN028164539A
Other languages
English (en)
Chinese (zh)
Other versions
CN1545508A (zh
Inventor
乔纳森·L·文纳斯特罗姆
雅克·肖莱
董玉湘
于格·马蒂勒
马尼扬·帕德马尼拉炎
唐元清
威廉·N·查曼
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MMV Medicines for Malaria Venture
Original Assignee
MMV Medicines for Malaria Venture
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.)
Filing date
Publication date
Application filed by MMV Medicines for Malaria Venture filed Critical MMV Medicines for Malaria Venture
Publication of CN1545508A publication Critical patent/CN1545508A/zh
Application granted granted Critical
Publication of CN1545508B publication Critical patent/CN1545508B/zh
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A61P33/12—Schistosomicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
    • C07D323/02—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • 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
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
  • Dental Preparations (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CN028164539A 2001-06-21 2002-06-21 1,2,4-三噁茂烷抗疟药 Expired - Lifetime CN1545508B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/886,666 US6486199B1 (en) 2001-06-21 2001-06-21 Spiro and dispiro 1,2,4-trioxolane antimalarials
US09/886,666 2001-06-21
PCT/US2002/019767 WO2003000676A1 (en) 2001-06-21 2002-06-21 1,2,4-trioxolane antimalarials

Publications (2)

Publication Number Publication Date
CN1545508A CN1545508A (zh) 2004-11-10
CN1545508B true CN1545508B (zh) 2012-06-06

Family

ID=25389491

Family Applications (1)

Application Number Title Priority Date Filing Date
CN028164539A Expired - Lifetime CN1545508B (zh) 2001-06-21 2002-06-21 1,2,4-三噁茂烷抗疟药

Country Status (24)

Country Link
US (1) US6486199B1 (https=)
EP (1) EP1414813B1 (https=)
JP (1) JP4303585B2 (https=)
KR (1) KR100759144B1 (https=)
CN (1) CN1545508B (https=)
AT (1) ATE339411T1 (https=)
AU (1) AU2002327183B2 (https=)
BR (1) BRPI0210549B8 (https=)
CA (1) CA2451006C (https=)
CY (1) CY1106214T1 (https=)
DE (1) DE60214733T8 (https=)
DK (1) DK1414813T3 (https=)
ES (1) ES2271323T3 (https=)
HU (1) HUP0400246A3 (https=)
IL (1) IL159474A0 (https=)
MX (1) MXPA03011915A (https=)
NO (1) NO20035721L (https=)
PL (1) PL226418B1 (https=)
PT (1) PT1414813E (https=)
RU (1) RU2271357C2 (https=)
SI (1) SI1414813T1 (https=)
UA (1) UA78709C2 (https=)
WO (1) WO2003000676A1 (https=)
YU (1) YU100703A (https=)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003103592A2 (en) * 2002-06-06 2003-12-18 University Of Washington Covalent conjugates between artemisinin-related endoperoxides and iron-carrying proteins and methods of use
US6825230B2 (en) * 2002-06-21 2004-11-30 Medicines For Malaria Venture Mmv Spiro and dispiro 1,2,4-trixolane antimalarials
US7371778B2 (en) * 2002-06-21 2008-05-13 Medicines For Malaria Venture Mmv Spiro and dispiro 1,2,4-trioxolane antimalarials
US20080125441A1 (en) * 2002-06-21 2008-05-29 Medicines For Malaria Venture Mmv Spiro and dispiro 1,2,4-trioxolane antimalarials
US6906205B2 (en) * 2002-06-21 2005-06-14 Medicines For Malaria Venture Mmv Spiro and dispiro 1,2,4-trioxolane antimalarials
FR2862304A1 (fr) * 2003-11-14 2005-05-20 Centre Nat Rech Scient Molecules duales racemiques ou achirales contenant un derive peroxydique, leur synthese et leurs applications therapeutiques
EP1789380A1 (de) * 2004-07-23 2007-05-30 Justus-Liebig-Universität Giessen Aminoadamantan-derivate, verfahren zu ihrer herstellung und ihre verwendung
US20060040761A1 (en) * 2004-08-23 2006-02-23 Sam-Kyu Shin Scale mark mat for putting practice
US8067620B2 (en) 2005-05-04 2011-11-29 Medicines For Malaria Venture Mmv Dispiro 1,2,4-trioxolane antimalarials
WO2006123314A2 (en) * 2005-05-18 2006-11-23 Ranbaxy Laboratories Limited Stable dosage forms of spiro and dispiro 1,2,4-trioxolane antimalarials
WO2007036947A1 (en) * 2005-09-30 2007-04-05 Ipca Laboratories Limited Delayed release anti-malarial composition
WO2007039915A1 (en) 2005-10-04 2007-04-12 The Director General, Defence Research And Development Organisation Anti-malarial compound isolated from gomphostema niveum
US20070231300A1 (en) * 2006-03-28 2007-10-04 Washington, University Of Covalent conjugates between endoperoxides and transferrin and lactoferrin receptor-binding agents
JP2009533368A (ja) 2006-04-11 2009-09-17 ノバルティス アクチエンゲゼルシャフト 有機化合物
WO2007132438A2 (en) * 2006-05-17 2007-11-22 Ranbaxy Laboratories Limited Antimalarial therapy using a combination of synthetic artemisinin derivative and bisquinoline derivative
SI2029569T1 (sl) * 2006-05-24 2013-03-29 Ranbaxy Laboratories Limited Postopek za pripravo dispiro-1,2,4-trioksolanskega protimalarijskega sredstva (OZ277 soli)
FR2902100A1 (fr) * 2006-06-13 2007-12-14 Sanofi Aventis Sa Molecules duales contenant un derive peroxydique, leur synthese et leurs applications en therapeutique
GB0619333D0 (en) * 2006-09-30 2006-11-08 Univ Liverpool Dispiro tetraoxane compounds
WO2008046109A2 (en) * 2006-10-13 2008-04-17 University Of Washington Conjugates of artemisinin-related endoperoxides and hydrazone derivatives for the treatment of cancer
FR2924343A1 (fr) * 2007-12-04 2009-06-05 Palumed Sa Nouvelles utilisations therapeutiques de molecules duales contenant un derive peroxydique.
EP2340829B1 (en) * 2008-07-01 2015-08-05 National University Corporation Okayama University Novel antischistosomal agent
US8618096B2 (en) 2008-07-21 2013-12-31 The Regents Of The University Of California Prodrug compositions and methods for using the same in treating cancer and malaria
KR20140053169A (ko) 2011-07-14 2014-05-07 랜박시 래보러터리스 리미티드 아르테롤란 및 피페라퀸의 안정한 제형
WO2015123595A1 (en) 2014-02-14 2015-08-20 The Regents Of The University Of California Cyclic peroxides as prodrugs for selective delivery of agents
JP6787899B2 (ja) 2014-12-23 2020-11-18 ベルゲンビオ アーエスアー 医薬的活性化合物
RU2601315C1 (ru) * 2015-06-10 2016-11-10 Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук Способ получения пентаоксаспироалканов
WO2019005977A1 (en) 2017-06-27 2019-01-03 The Regents Of The University Of California Trioxolane agents
CN108424371B (zh) * 2018-01-19 2021-07-16 北京理工大学 2-(4-氨基环己基)-乙酸乙酯的制备方法
US20210386814A1 (en) * 2020-05-20 2021-12-16 Amanuel Tesfazion Methods and compound for the treatment of malaria
WO2022161490A1 (en) * 2021-02-01 2022-08-04 Dan Yang Targeted delivery of 1, 2, 4, 5-tetraoxane compounds and their uses
CN117085004A (zh) * 2023-09-27 2023-11-21 赣南师范大学 一种2,6-二苯亚甲基环己酮类似物在制备抗血吸虫药物中的应用

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3621062A (en) 1966-10-25 1971-11-16 Sterling Drug Inc 2-(8-cyclohexyloctanoyl or 7-cyclohexylheptanoyl)-1-naphthol
US3673222A (en) 1969-11-26 1972-06-27 Sydney Archer 2-(8-cyclohexyloctyl or 7-cyclohexylheptyl)-1,4-naphthoquinone and process for preparation and use thereof
US3682991A (en) 1970-10-19 1972-08-08 Sterling Drug Inc 3,3,5-trimethylcyclohexyl-alkyl-carboxylic acids
SU1421743A1 (ru) * 1987-02-18 1988-09-07 Физико-химический институт им.А.В.Богатского Способ получени 11-нитро-12- @ (2-метокси)-этокси @ -бензо-9-краун-3
US4916204A (en) 1987-07-31 1990-04-10 Massachusetts Institute Of Technology Pure polyanhydride from dicarboxylic acid and coupling agent
US4816478A (en) 1987-08-24 1989-03-28 Thornfeldt Carl R Treatment of acquired immunodeficiency syndrome
US5053342A (en) 1987-12-24 1991-10-01 Litmus Concepts, Inc. Fecal occult blood test reagents
US5559145A (en) 1988-06-01 1996-09-24 Oxaco S.A. 1,2,4-trioxane derivatives
US5270344A (en) 1988-06-24 1993-12-14 Stephen Herman Method of treating a systemic disorder using trioxolane and diperoxide compounds
JP2867529B2 (ja) 1990-01-22 1999-03-08 三菱電機株式会社 投写型表示装置
US5216175A (en) 1990-03-23 1993-06-01 Sri International Antimalarial analogs of artemisinin
US5219880A (en) 1991-03-29 1993-06-15 Dermatologic Research Corporation Treatment of viral tumors and hemorrhoids with artemisinin and derivatives
DE4125201C1 (https=) * 1991-07-30 1992-10-01 Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung Ev, 8000 Muenchen, De
US5510356A (en) 1991-10-03 1996-04-23 University Of Nebraska Board Of Regents Bisquinolines and processes for their production and use to treat malaria
US5171676A (en) 1991-10-31 1992-12-15 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Method of introducing hydroxyl groups into artemisinin and its derivatives
US5430148A (en) 1992-03-31 1995-07-04 Agouron Pharmaceuticals, Inc. Antiproliferative quinazolines
AU4673993A (en) 1992-07-28 1994-02-14 Procter & Gamble Company, The Pharmaceutical composition for topical use containing a crosslinked cationic polymer and an alkoxylated ether
US5721209A (en) 1995-02-03 1998-02-24 The Regents Of The University Of California Iron chelator and inhibitor of iron-mediated oxidant injury
US5780675A (en) 1995-04-28 1998-07-14 The University Of New Mexico Deoxygossylic compounds
US5578637A (en) 1995-05-03 1996-11-26 University Of Washington Methods of inhibition or killing cancer cells using an endoperoxide
US5817692A (en) 1995-11-22 1998-10-06 The Johns Hopkins University Endoperoxides useful as antiparasitic agents
US5672624A (en) 1995-11-22 1997-09-30 The Johns Hopkins University Endoperoxides useful as antiparasitic agents
US5932591A (en) 1996-12-02 1999-08-03 Johns Hopkins University C3 substituted trioxanes useful as antiparasitic drugs

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
作者:GRIESBAUM K ET AL.标题:Diozonides from Coozonolyses of Suitable O-Methyl Oximesand Ketones.TETRAHEDRON,1997卷号:53 期号:15.1997,53(15),5463-5470. *
作者:HELMUT KEUL.标题:über Konstitution und Entstehung der Ozonide vonBis-adamantyliden und Bis-bicyclo[3.3.1]non-9-ylid.CHEMISCHE BERICHTE卷号:108 期号:4.1975,108(4),1207-1217. *
作者:P. H. DUSSAULT, H.-J. LEE, X. LIU.标题:Selectivity in Lewis acid-mediated fragmentations ofperoxides and ozonides;application to the synthesis ofalkenes, homoallylethers, and 1,2-dioxolanes.J.CHEM.SOC.PERKIN TRANS.2000卷号:1 期号:.2000,13006-3013. *
作者:T. TABUCHI, M. NOJIMA.标题:Ozonolysis of vinyl ethers in the presence of alpha-diketonesand alpha-keto esters.J. ORG.CHEM.1991卷号:56 期号:.1991,566591-6595. *

Also Published As

Publication number Publication date
US6486199B1 (en) 2002-11-26
PL367158A1 (en) 2005-02-21
HUP0400246A3 (en) 2009-12-28
RU2004101409A (ru) 2005-06-10
AU2002327183C1 (en) 2003-01-08
MXPA03011915A (es) 2004-05-21
HUP0400246A2 (hu) 2004-08-30
BRPI0210549B1 (pt) 2020-11-10
BRPI0210549B8 (pt) 2021-05-25
RU2271357C2 (ru) 2006-03-10
ATE339411T1 (de) 2006-10-15
IL159474A0 (en) 2004-06-01
KR20040030697A (ko) 2004-04-09
CA2451006A1 (en) 2003-01-03
PL226418B1 (pl) 2017-07-31
DE60214733T2 (de) 2007-09-13
CN1545508A (zh) 2004-11-10
DE60214733T8 (de) 2008-02-21
DK1414813T3 (da) 2007-01-02
AU2002327183B2 (en) 2006-03-09
WO2003000676A1 (en) 2003-01-03
CY1106214T1 (el) 2011-06-08
UA78709C2 (en) 2007-04-25
YU100703A (sh) 2006-03-03
DE60214733D1 (de) 2006-10-26
NO20035721L (no) 2004-02-23
JP2004535436A (ja) 2004-11-25
BR0210549A (pt) 2005-01-11
PT1414813E (pt) 2006-12-29
JP4303585B2 (ja) 2009-07-29
KR100759144B1 (ko) 2007-09-14
CA2451006C (en) 2011-08-23
EP1414813A1 (en) 2004-05-06
SI1414813T1 (sl) 2006-12-31
ES2271323T3 (es) 2007-04-16
EP1414813B1 (en) 2006-09-13
NO20035721D0 (no) 2003-12-19

Similar Documents

Publication Publication Date Title
CN1545508B (zh) 1,2,4-三噁茂烷抗疟药
CN100384834C (zh) 埃坡霉素衍生物
AU2002327183A1 (en) 1,2,4-trioxolane antimalarials
TWI294292B (en) Combination of epothilone derivatives
KR20040065289A (ko) Ｎｋ1 길항제로서 피롤리딘 및 피페리딘 유도체
WO2016107603A1 (zh) 取代氮杂环衍生物及其应用
CZ409398A3 (cs) Amidy kyseliny pyridylalkenové a pyridylalkinové jako cytostatika a imunosupresiva
TW200528459A (en) Azabenzofuran substituted thioureas; inhibitors of viral replication
ZA200210114B (en) Substituted pyrrolopyridinone derivatives useful as phosphodiesterase inhibitors.
JP6793657B2 (ja) 置換三環式ヘテロ環式化合物
US20040186168A1 (en) Spiro and dispiro 1,2,4-trioxolane antimalarials
CN101842377B (zh) 二螺1,2,4-三氧杂环戊烷抗疟药
JP7592748B2 (ja) 抗ウイルス１，３－ジ－オキソ－インデン化合物
US6825230B2 (en) Spiro and dispiro 1,2,4-trixolane antimalarials
WO2009091433A2 (en) Spiro and dispiro 1,2,4-trioxolane antimalarials
WO2002016369A2 (en) Novel macrocycles and uses thereof
US20060258665A1 (en) Bridged ring NK1 antagonists
US20030176368A1 (en) Synthesis of epothilones, intermediates thereto and analogues thereof
CN101631792A (zh) 新的磷酸二酯酶抑制剂
WO1999054303A1 (en) Optically active tetrahydrobenzindole derivatives
KR20000062356A (ko) 5-ｈｔ 수용체 활성을 갖는 술폰아미드 화합물
RU2136675C1 (ru) Производные 3-(5-тетразолилбензил)аминопиперидина, способы их получения и фармацевтическая композиция на их основе
JP2781073B2 (ja) 新規キノリン誘導体及びそれを有効成分として含有する制癌剤効果増強剤
Magura Photochemical synthesis of dihydroquinolinones and their investigation toward macrocycle synthesis via ring expansion
JP3165409B2 (ja) アルキレンジオキシベンゼン誘導体を有効成分とする抗不安薬

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CX01 Expiry of patent term
CX01 Expiry of patent term

Granted publication date: 20120606