CN100540548C - 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成 - Google Patents

脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成 Download PDF

Info

Publication number
CN100540548C
CN100540548C CNB038234645A CN03823464A CN100540548C CN 100540548 C CN100540548 C CN 100540548C CN B038234645 A CNB038234645 A CN B038234645A CN 03823464 A CN03823464 A CN 03823464A CN 100540548 C CN100540548 C CN 100540548C
Authority
CN
China
Prior art keywords
compound
replacement
group
kpu
alkyl
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
CNB038234645A
Other languages
English (en)
Chinese (zh)
Other versions
CN1684955A (zh
Inventor
林良雄
珍妮弗·格罗得伯格
迈克尔·帕拉迪诺
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.)
BeyondSpring Pharmaceuticals Inc
Original Assignee
Nereus Pharmaceuticals 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.)
Filing date
Publication date
Application filed by Nereus Pharmaceuticals Inc filed Critical Nereus Pharmaceuticals Inc
Publication of CN1684955A publication Critical patent/CN1684955A/zh
Application granted granted Critical
Publication of CN100540548C publication Critical patent/CN100540548C/zh
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • 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
    • A61P31/10—Antimycotics
    • 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
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Epoxy Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CNB038234645A 2002-08-02 2003-08-01 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成 Expired - Lifetime CN100540548C (zh)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US40107402P 2002-08-02 2002-08-02
US60/401,074 2002-08-02
US41112802P 2002-09-16 2002-09-16
US60/411,128 2002-09-16
US45006303P 2003-02-24 2003-02-24
US60/450,063 2003-02-24

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CN200910160084.4A Division CN101633655B (zh) 2002-08-02 2003-08-01 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成

Publications (2)

Publication Number Publication Date
CN1684955A CN1684955A (zh) 2005-10-19
CN100540548C true CN100540548C (zh) 2009-09-16

Family

ID=32600863

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB038234645A Expired - Lifetime CN100540548C (zh) 2002-08-02 2003-08-01 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成

Country Status (19)

Country Link
US (4) US7064201B2 (enExample)
EP (1) EP1529044B1 (enExample)
JP (1) JP4616649B2 (enExample)
KR (2) KR101184374B1 (enExample)
CN (1) CN100540548C (enExample)
AT (1) ATE374767T1 (enExample)
AU (1) AU2003302721B2 (enExample)
BR (2) BR0313363A (enExample)
CA (1) CA2494049C (enExample)
CO (1) CO5721010A2 (enExample)
DE (1) DE60316688T2 (enExample)
DK (1) DK1529044T5 (enExample)
ES (1) ES2295695T3 (enExample)
IL (2) IL166628A0 (enExample)
MX (1) MXPA05001217A (enExample)
NZ (1) NZ538433A (enExample)
PT (1) PT1529044E (enExample)
WO (1) WO2004054498A2 (enExample)
ZA (1) ZA200501616B (enExample)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107427510A (zh) * 2015-02-12 2017-12-01 万春药业公司 普那布林联合免疫检查点抑制剂的用途
CN109498627A (zh) * 2017-09-15 2019-03-22 青岛海洋生物医药研究院股份有限公司 一种治疗肿瘤的药物组合物及其应用

Families Citing this family (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7026322B2 (en) 1998-11-12 2006-04-11 Nereus Pharmaceuticals, Inc. Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds
KR100831400B1 (ko) * 2000-01-18 2008-05-21 니리어스 파마슈티컬즈, 인크. 세포분열 저해제 및 그의 제조방법
PT1311269E (pt) 2000-08-04 2012-05-10 Dmi Biosciences Inc Método de utilização de dicetopiperazinas e composição que contém as mesmas
ATE374767T1 (de) 2002-08-02 2007-10-15 Nereus Pharmaceuticals Inc Dehydrophenylahistine und analoge davon sowie ein verfahren zur herstellung von dehydrophenylahistinen und analogen davon
US7935704B2 (en) 2003-08-01 2011-05-03 Nereus Pharmaceuticals, Inc. Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
US7919497B2 (en) 2002-08-02 2011-04-05 Nereus Pharmaceuticals, Inc. Analogs of dehydrophenylahistins and their therapeutic use
EP1571970B1 (en) 2002-10-02 2011-08-17 DMI Biosciences, Inc. Diagnosis and monitoring of diseases
KR20120101164A (ko) 2003-05-15 2012-09-12 디엠아이 바이오사이언시스, 인크 Ｔ-세포 매개성 질환의 치료 방법
WO2005077940A1 (en) * 2004-02-04 2005-08-25 Nereus Pharmaceuticals, Inc. Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
EP1830847B1 (en) * 2004-12-06 2014-11-19 Pitney Pharmaceuticals Pty Limited Treatment for cancer
US7732605B2 (en) 2005-03-29 2010-06-08 Nereus Pharmaceuticals, Inc. Synthesis of diketopiperazines
JP2008024871A (ja) * 2006-07-24 2008-02-07 Fujifilm Corp インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び平版印刷版
KR100932093B1 (ko) 2006-09-27 2009-12-16 주식회사종근당 미세소관 형성 저해제로서 유용한 벤조페논 유도체
US8129527B2 (en) 2006-11-03 2012-03-06 Nereus Pharmacuticals, Inc. Analogs of dehydrophenylahistins and their therapeutic use
JP5856843B2 (ja) 2008-05-27 2016-02-10 アンピオ ファーマシューティカルズ，インコーポレイテッド ジケトピペラジンを用いた医薬組成物
AU2009316773A1 (en) * 2008-11-21 2010-05-27 Isis Pharmaceuticals, Inc. Anticancer combination comprising docetaxel and an antisense oligonucleotide
EP2566474B1 (en) 2010-05-03 2017-11-15 Teikoku Pharma USA, Inc. Non-aqueous taxane pro-emulsion formulations and methods of making and using the same
CA2810844C (en) 2010-09-07 2017-03-21 Dmi Acquisition Corp. Diketopiperazine compositions for the treatment of metabolic syndrome and related conditions
WO2012035436A1 (en) * 2010-09-15 2012-03-22 Tokyo University Of Pharmacy And Life Sciences Plinabulin prodrug analogs and therapeutic uses thereof
US8842114B1 (en) 2011-04-29 2014-09-23 Nvidia Corporation System, method, and computer program product for adjusting a depth of displayed objects within a region of a display
EP2766029B1 (en) 2011-10-10 2020-03-25 Ampio Pharmaceuticals, Inc. Treatment of degenerative joint disease
MX2014003856A (es) 2011-10-10 2015-01-16 Ampio Pharmaceuticals Inc Dispositivos medicos implantables con tolerancia inmune incrementada y metodos para hacerlos e implantarlos.
SG11201400283RA (en) 2011-10-28 2014-03-28 Ampio Pharmaceuticals Inc Treatment of rhinitis
JO3685B1 (ar) 2012-10-01 2020-08-27 Teikoku Pharma Usa Inc صيغ التشتيت الجسيمي للتاكسين غير المائي وطرق استخدامها
AU2014232728B2 (en) 2013-03-15 2019-02-21 Ampio Pharmaceuticals, Inc. Compositions for the mobilization, homing, expansion and differentiation of stem cells and methods of using the same
JP6311097B2 (ja) * 2013-07-31 2018-04-18 学校法人東京薬科大学 微小管脱重合剤
RU2662298C2 (ru) 2013-10-11 2018-07-25 Бьёндспринг Инк. Лечение рака комбинацией плинабулина и таксана
EP3183240A4 (en) 2014-08-18 2018-06-27 Ampio Pharmaceuticals, Inc. Treatment of joint conditions
CN107530341B (zh) 2015-03-06 2021-10-01 大连万春布林医药有限公司 治疗与ras突变相关的癌症的方法
RU2728796C2 (ru) 2015-03-06 2020-07-31 Бейондспринг Фармасьютикалс, Инк. Способ лечения опухоли головного мозга
CN106279039B (zh) * 2015-06-02 2019-01-11 青岛海洋生物医药研究院股份有限公司 氘代脱氢苯基阿夕斯丁类化合物及其制备方法和在制备抗肿瘤的药物中的应用
US11389512B2 (en) 2015-06-22 2022-07-19 Ampio Pharmaceuticals, Inc. Use of low molecular weight fractions of human serum albumin in treating diseases
DK3334726T3 (da) 2015-07-13 2022-05-16 Beyondspring Pharmaceuticals Inc Plinabulinsammensætninger
AU2017217426B2 (en) 2016-02-08 2022-12-01 Beyondspring Pharmaceuticals, Inc. Compositions containing tucaresol or its analogs
SG11201810872UA (en) * 2016-06-06 2019-01-30 Beyondspring Pharmaceuticals Inc Composition and method for reducing neutropenia
US10851086B2 (en) 2016-08-12 2020-12-01 Marine Biomedical Research Institute Of Qingdao Co., Ltd. Polycrystalline form of dehydrophenylahistin-like compound, and manufacturing and purification method and application thereof
CN107011322B (zh) * 2016-08-12 2020-02-18 青岛海洋生物医药研究院股份有限公司 一种脱氢苯基阿夕斯丁类化合物的制备纯化方法
CN107778297B (zh) * 2016-08-12 2021-11-19 深圳华大海洋科技有限公司 氘代脱氢苯基阿夕斯丁类化合物的多晶型及其制备方法和应用
CN107011331A (zh) * 2016-08-12 2017-08-04 青岛海洋生物医药研究院股份有限公司 脱氢苯基阿夕斯丁类化合物的多晶型及其制备方法
CN106565685B (zh) * 2016-10-11 2019-03-01 深圳海王医药科技研究院有限公司 微管蛋白抑制剂
CN106565686B (zh) * 2016-10-11 2019-03-01 深圳海王医药科技研究院有限公司 微管蛋白抑制剂
CN110431135A (zh) 2017-01-06 2019-11-08 大连万春布林医药有限公司 微管蛋白结合化合物及其治疗用途
CN110381938A (zh) 2017-02-01 2019-10-25 大连万春布林医药有限公司 减少中性粒细胞缺乏症的方法
ES2942889T3 (es) 2017-03-13 2023-06-07 Beyondspring Pharmaceuticals Inc Composiciones de plinabulina y uso de las mismas
CN108658945B (zh) * 2017-03-31 2020-11-20 深圳海王医药科技研究院有限公司 一种微管蛋白抑制剂（vda-1）的a晶型
WO2019028144A1 (en) 2017-08-03 2019-02-07 Teva Pharmaceuticals Usa, Inc. SALTS AND FORMS IN THE SOLID STATE OF PLINABULIN
CN107698567B (zh) * 2017-10-25 2020-09-15 西南大学 靛红唑醇类化合物及其制备方法和医药应用
CA3089226A1 (en) 2018-01-24 2019-08-01 Beyondspring Pharmaceuticals, Inc. Composition and method for reducing thrombocytopenia via the administration of plinabulin
CN108299399A (zh) * 2018-02-01 2018-07-20 深圳海王医药科技研究院有限公司 一种小分子免疫化合物的晶型、其制备方法和含有其的药物组合物
MX2020012799A (es) * 2018-06-01 2021-03-25 Beyondspring Pharmaceuticals Inc Composicion y metodo para tratar el cancer asociado con mutacion del egfr.
CN109030642B (zh) * 2018-06-26 2021-03-09 深圳海王医药科技研究院有限公司 一种脱氢苯基阿夕斯丁类似物及其异构体的测定方法
CN111840291B (zh) * 2020-07-14 2021-12-21 深圳海王医药科技研究院有限公司 一种在肿瘤治疗中具有增效作用的化合物的应用
EP4319751A4 (en) 2021-04-09 2025-02-26 Beyondspring Pharmaceuticals, Inc. THERAPEUTIC COMPOSITIONS AND METHODS FOR THE TREATING OF TUMORS
CN117164560A (zh) * 2022-06-02 2023-12-05 上海旭成医药科技有限公司 哌嗪酮类化合物及其制备方法和用途
CN117285516A (zh) * 2022-06-16 2023-12-26 大连万众益生大健康有限公司 脱氢苯基阿夕斯汀类化合物、其制备方法及其应用
CN117860672A (zh) 2022-10-11 2024-04-12 大连万春布林医药有限公司 一种普那布林胶束组合物及其制备方法
WO2024191805A1 (en) 2023-03-10 2024-09-19 Beyondspring Pharmaceuticals, Inc. Oncology combination therapy and methods of use

Family Cites Families (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU576322B2 (en) 1983-07-22 1988-08-25 Ici Australia Limited Alpha-substituted-alpha-cyanomethyl alcohols
JPH059164A (ja) 1991-07-02 1993-01-19 Sumitomo Chem Co Ltd 光学活性マンデロニトリル誘導体の製造方法
GB9217331D0 (en) 1992-08-14 1992-09-30 Xenova Ltd Pharmaceutical compounds
DK0674510T3 (da) 1992-11-27 1999-05-10 Napro Biotherapeutics Inc Injicerbart præparat omfattende paclitaxel
JPH0725858A (ja) 1993-07-13 1995-01-27 Otsuka Pharmaceut Co Ltd ピペラジン誘導体
GB9402807D0 (en) * 1994-02-14 1994-04-06 Xenova Ltd Pharmaceutical compounds
GB9402809D0 (en) * 1994-02-14 1994-04-06 Xenova Ltd Pharmaceutical compounds
GB9426224D0 (en) 1994-12-23 1995-02-22 Xenova Ltd Pharmaceutical compounds
US5891877A (en) * 1995-02-14 1999-04-06 Xenova Limited Pharmaceutical compounds
US5874443A (en) 1995-10-19 1999-02-23 Trega Biosciences, Inc. Isoquinoline derivatives and isoquinoline combinatorial libraries
US5886210A (en) 1996-08-22 1999-03-23 Rohm And Haas Company Method for preparing aromatic compounds
JP3131574B2 (ja) 1996-09-04 2001-02-05 新日本製鐵株式会社 新規抗腫瘍物質、該物質を製造するための微生物及び方法、並びに該物質を有効成分とする細胞周期阻害剤及び抗腫瘍剤
US5922683A (en) 1997-05-29 1999-07-13 Abbott Laboratories Multicyclic erythromycin derivatives
MXPA00004919A (es) 1997-11-21 2002-10-17 Euro Celtique Sa 2-aminoacetamidas sustituidas y uso de las mismas.
CN1173946C (zh) 1998-01-29 2004-11-03 阿温蒂斯药物公司 制备n-[(脂族或芳族)羰基]-2-氨基乙酰胺化合物和环化化合物的方法
US6069146A (en) 1998-03-25 2000-05-30 The Regents Of The University Of California Halimide, a cytotoxic marine natural product, and derivatives thereof
RU2217421C2 (ru) 1998-03-26 2003-11-27 Шионоги & Ко., Лтд. Производные индола, обладающие антивирусной активностью
US6509331B1 (en) 1998-06-22 2003-01-21 Elan Pharmaceuticals, Inc. Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
FR2784988B1 (fr) 1998-10-23 2002-09-20 Adir Nouveaux composes dihydro et tetrahydroquinoleiniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US7026322B2 (en) 1998-11-12 2006-04-11 Nereus Pharmaceuticals, Inc. Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds
US6358957B1 (en) 1998-11-12 2002-03-19 Nereus Pharmaceuticals, Inc. Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds
KR100831400B1 (ko) 2000-01-18 2008-05-21 니리어스 파마슈티컬즈, 인크. 세포분열 저해제 및 그의 제조방법
EP1345938A1 (en) 2000-12-28 2003-09-24 Neurocrine Biosciences, Inc. Tricyclic crf receptor antagonists
US6569556B2 (en) * 2001-01-29 2003-05-27 General Motors Corporation Cooling system for a battery pack
US7935704B2 (en) 2003-08-01 2011-05-03 Nereus Pharmaceuticals, Inc. Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
ATE374767T1 (de) 2002-08-02 2007-10-15 Nereus Pharmaceuticals Inc Dehydrophenylahistine und analoge davon sowie ein verfahren zur herstellung von dehydrophenylahistinen und analogen davon
US7919497B2 (en) 2002-08-02 2011-04-05 Nereus Pharmaceuticals, Inc. Analogs of dehydrophenylahistins and their therapeutic use
WO2005077940A1 (en) 2004-02-04 2005-08-25 Nereus Pharmaceuticals, Inc. Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
US8129527B2 (en) 2006-11-03 2012-03-06 Nereus Pharmacuticals, Inc. Analogs of dehydrophenylahistins and their therapeutic use

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF ORGANIC CHEMISTRY. Y. HAYAHI ET AL.:,8402-8405,Total synthesis of anti-microtubule diketopiperazinederivatives: Phenylahistin and Aurantiamine.. 2000
JOURNAL OF ORGANIC CHEMISTRY. Y. HAYAHI ET AL.:,8402-8405,Total synthesis of anti-microtubule diketopiperazinederivatives: Phenylahistin and Aurantiamine. 2000 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107427510A (zh) * 2015-02-12 2017-12-01 万春药业公司 普那布林联合免疫检查点抑制剂的用途
CN109498627A (zh) * 2017-09-15 2019-03-22 青岛海洋生物医药研究院股份有限公司 一种治疗肿瘤的药物组合物及其应用
CN109498627B (zh) * 2017-09-15 2021-06-04 深圳华大海洋科技有限公司 一种治疗肿瘤的药物组合物及其应用

Also Published As

Publication number Publication date
DE60316688D1 (de) 2007-11-15
US7674903B2 (en) 2010-03-09
US20050090667A1 (en) 2005-04-28
CA2494049A1 (en) 2004-07-01
AU2003302721A1 (en) 2004-07-09
EP1529044A2 (en) 2005-05-11
US20060217553A1 (en) 2006-09-28
IL166628A0 (en) 2006-01-15
CN1684955A (zh) 2005-10-19
WO2004054498A3 (en) 2004-11-25
KR20110039500A (ko) 2011-04-18
KR20050083610A (ko) 2005-08-26
PT1529044E (pt) 2008-01-14
US7064201B2 (en) 2006-06-20
US7956058B2 (en) 2011-06-07
AU2003302721B2 (en) 2009-10-08
CO5721010A2 (es) 2007-01-31
IL166628A (en) 2012-08-30
ZA200501616B (en) 2005-11-30
KR101049100B1 (ko) 2011-07-15
US20060223822A1 (en) 2006-10-05
BR0313363A (pt) 2005-08-09
DK1529044T3 (da) 2008-02-04
NZ538433A (en) 2008-02-29
HK1078080A1 (en) 2006-03-03
EP1529044B1 (en) 2007-10-03
BRPI0313363A8 (pt) 2019-01-02
ATE374767T1 (de) 2007-10-15
US20060223823A1 (en) 2006-10-05
DE60316688T2 (de) 2008-07-17
CA2494049C (en) 2011-10-18
JP2006511534A (ja) 2006-04-06
ES2295695T3 (es) 2008-04-16
DK1529044T5 (da) 2008-04-21
JP4616649B2 (ja) 2011-01-19
MXPA05001217A (es) 2005-05-16
KR101184374B1 (ko) 2012-09-20
HK1084388A1 (zh) 2006-07-28
WO2004054498A2 (en) 2004-07-01

Similar Documents

Publication Publication Date Title
CN100540548C (zh) 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成
US8129527B2 (en) Analogs of dehydrophenylahistins and their therapeutic use
US7919497B2 (en) Analogs of dehydrophenylahistins and their therapeutic use
US7935704B2 (en) Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
KR101228104B1 (ko) 데하이드로페닐아히스틴 및 그의 동족체, 및 이들의합성방법
CN1934101B (zh) 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成
CN101633655A (zh) 脱氢苯基阿夕斯丁及其类似物以及脱氢苯基阿夕斯丁及其类似物的合成
HK1078080B (en) Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
HK1084388B (en) Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
REG Reference to a national code

Ref country code: HK

Ref legal event code: DE

Ref document number: 1084388

Country of ref document: HK

C14 Grant of patent or utility model
GR01 Patent grant
REG Reference to a national code

Ref country code: HK

Ref legal event code: GR

Ref document number: 1084388

Country of ref document: HK

ASS Succession or assignment of patent right

Owner name: DALIAN WANCHUN BIOTECHNOLOGY CO., LTD.

Free format text: FORMER OWNER: NEREUS PHARMACEUTICALS INC.

Effective date: 20110913

C41 Transfer of patent application or patent right or utility model
COR Change of bibliographic data

Free format text: CORRECT: ADDRESS; TO: 116025 DALIAN, LIAONING PROVINCE

TR01 Transfer of patent right

Effective date of registration: 20110913

Address after: Dalian high tech Industrial Park in Liaoning province 116025 base Qixianling Torch Road No. 1 block A No. 507

Patentee after: Dalian million spring Biotechnology Co.,Ltd.

Address before: California, USA

Patentee before: Nereus Pharmaceuticals, Inc.

ASS Succession or assignment of patent right

Owner name: DALIAN WANCHUN PHARMACEUTICAL CO., LTD.

Free format text: FORMER OWNER: DALIAN WANCHUN BIOTECHNOLOGY CO., LTD.

Effective date: 20130201

C41 Transfer of patent application or patent right or utility model
TR01 Transfer of patent right

Effective date of registration: 20130201

Address after: 116025 No. 9, Liaohe East Road, Dalian economic and Technological Development Zone, Liaoning

Patentee after: Dalian Wanchun Pharmaceutical Co.,Ltd.

Address before: Dalian high tech Industrial Park in Liaoning province 116025 base Qixianling Torch Road No. 1 block A No. 507

Patentee before: Dalian million spring Biotechnology Co.,Ltd.

ASS Succession or assignment of patent right

Owner name: DALIAN WANCHUN BIOTECHNOLOGY CO., LTD.

Free format text: FORMER OWNER: DALIAN WANCHUN PHARMACEUTICAL CO., LTD.

Effective date: 20150723

C41 Transfer of patent application or patent right or utility model
TR01 Transfer of patent right

Effective date of registration: 20150723

Address after: 116000 18 D5 street, Dalian economic and Technological Development Zone, Liaoning, China

Patentee after: Dalian million spring Biotechnology Co.,Ltd.

Address before: No. 9, Liaohe East Road, Dalian economic and Technological Development Zone, Liaoning, Dalian

Patentee before: Dalian Wanchun Pharmaceutical Co.,Ltd.

ASS Succession or assignment of patent right

Owner name: DALIAN WANCHUN BULIN PHARMACEUTICAL CO., LTD.

Free format text: FORMER OWNER: DALIAN WANCHUN BIOTECHNOLOGY CO., LTD.

Effective date: 20150908

C41 Transfer of patent application or patent right or utility model
TR01 Transfer of patent right

Effective date of registration: 20150908

Address after: 116000 -6, four D street, 19 economic and Technological Development Zone, Liaoning, Dalian

Patentee after: BEYONDSPRING PHARMACEUTICALS, Inc.

Address before: 116000 18 D5 street, Dalian economic and Technological Development Zone, Liaoning, China

Patentee before: Dalian million spring Biotechnology Co.,Ltd.

CX01 Expiry of patent term
CX01 Expiry of patent term

Granted publication date: 20090916