ZA200005018B - Novel cephalotaxane derivatives and process for their preparation. - Google Patents

Novel cephalotaxane derivatives and process for their preparation. Download PDF

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Publication number
ZA200005018B
ZA200005018B ZA200005018A ZA200005018A ZA200005018B ZA 200005018 B ZA200005018 B ZA 200005018B ZA 200005018 A ZA200005018 A ZA 200005018A ZA 200005018 A ZA200005018 A ZA 200005018A ZA 200005018 B ZA200005018 B ZA 200005018B
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ZA
South Africa
Prior art keywords
following formula
acid
ctx
formula
radical
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ZA200005018A
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English (en)
Inventor
Jean-Pierre Robin
Julie Robin
Sylvie Cavoleau
Ludovic Chauviat
Sandra Charbonnel
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Oncopharm Corp
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Publication of ZA200005018B publication Critical patent/ZA200005018B/en

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    • 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
    • C07D491/12—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 three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyrane Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
ZA200005018A 1998-03-20 2000-09-20 Novel cephalotaxane derivatives and process for their preparation. ZA200005018B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9803492A FR2776292B1 (fr) 1998-03-20 1998-03-20 Cephalotaxanes porteurs de chaine laterale et leur procede de synthese

Publications (1)

Publication Number Publication Date
ZA200005018B true ZA200005018B (en) 2001-03-22

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ZA200005018A ZA200005018B (en) 1998-03-20 2000-09-20 Novel cephalotaxane derivatives and process for their preparation.

Country Status (19)

Country Link
US (5) US6831180B1 (de)
EP (1) EP1064285B1 (de)
JP (3) JP4942871B2 (de)
KR (1) KR20010042085A (de)
CN (1) CN1220692C (de)
AT (1) ATE289312T1 (de)
AU (1) AU3270699A (de)
CA (1) CA2324895A1 (de)
DE (1) DE69923768T2 (de)
DK (1) DK1064285T3 (de)
ES (1) ES2237144T3 (de)
FR (1) FR2776292B1 (de)
HU (1) HUP0101375A3 (de)
IL (1) IL138563A0 (de)
PL (1) PL343032A1 (de)
PT (1) PT1064285E (de)
TR (1) TR200003613T2 (de)
WO (1) WO1999048894A1 (de)
ZA (1) ZA200005018B (de)

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FR2776292B1 (fr) 1998-03-20 2004-09-10 Oncopharm Cephalotaxanes porteurs de chaine laterale et leur procede de synthese
AU7940500A (en) * 2000-10-17 2002-04-29 Oncopharm Corp New cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including thus resistant to usual chemotherapeutic agents and as reversal agents
US7285546B2 (en) 2000-10-17 2007-10-23 Stragen Pharma S.A. Cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including those resistant to usual chemotherapeutic agents and as reversal agents
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JP5550546B2 (ja) * 2007-04-13 2014-07-16 ケムジェネックス・ファーマシューティカルズ・インコーポレイテッド 経口セファロタキシン剤形
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CN103635476B (zh) * 2011-08-18 2016-03-09 杭州本生药业有限公司 高三尖杉酯碱的酰化衍生物、及其制备方法和应用
JP6068472B2 (ja) 2011-08-18 2017-01-25 ハンジョウ ベンシェン ファーマシューティカル シーオー．， エルティーディー．Ｈａｎｇｚｈｏｕ Ｂｅｎｓｈｅｎｇ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． アミノ化ホモハリントニン誘導体、その調製方法及び使用
CN103687859B (zh) * 2011-08-18 2016-08-17 杭州本生药业有限公司 高三尖杉酯碱的胺化衍生物、及其制备方法和应用
WO2013023622A1 (zh) * 2011-08-18 2013-02-21 杭州本生药业有限公司 高三尖杉酯碱的酰化衍生物、及其制备方法和应用
CN102675327B (zh) * 2012-03-01 2014-12-10 南开大学 三尖杉酯碱类似物及制备方法和应用
CN102633806A (zh) * 2012-04-05 2012-08-15 贵州博丰生物科技产业开发有限公司 一种三尖杉酯碱的提取分离方法
WO2015101628A1 (en) * 2013-12-31 2015-07-09 Jean-Pierre Robin Water soluble crystallin salts of certain harringtonines unambiguously protonated on their alkaloid nitrogen and their use as chemotherapeutic drugs
WO2015128463A1 (en) * 2014-02-28 2015-09-03 Jean-Pierre Robin Water soluble salts of harringtonine and their pharmaceutical applications
WO2015162217A2 (en) * 2014-04-23 2015-10-29 Jean-Pierre Robin Crystalline salts of cephalotaxine and their use for its purification including enantiomers
WO2016182850A1 (en) * 2015-05-08 2016-11-17 Albany Molecular Research, Inc. Methods and intermediates for the preparation of omacetaxine and cephalotaxine derivatives thereof
CN106866690B (zh) * 2015-12-10 2019-10-11 南开大学 三尖杉酯类生物碱、其制备方法和用途
EP3275875A1 (de) 2016-07-28 2018-01-31 INDENA S.p.A. Dioxolanon-zwischenprodukt zur synthese von homoharringtonin
CN110577506B (zh) * 2018-06-07 2023-04-07 中国科学院上海有机化学研究所 (﹣)-三尖杉碱的酯类衍生物的合成方法及其中间体
EP3763715A1 (de) 2019-07-11 2021-01-13 Robin, Jean-Pierre Harringtoninen-salze, insbesondere retinoate, deren verfahren zur herstellung und deren verwendungen in der behandlung von leukämien, tumoren, autoimmun-, haut-, alzheimer- und entzündlichen darmerkrankungen und viralen infektionen, kombiniert mit myelopoiesestimulierenden mitteln
CN114544849B (zh) * 2022-02-22 2024-07-19 苏州正济医药研究有限公司 一种1h-1,2,4-三氮唑-1-甲脒单盐酸盐及杂质的检测方法
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US6831180B1 (en) 2004-12-14
AU3270699A (en) 1999-10-18
US20060234999A1 (en) 2006-10-19
US20020045750A1 (en) 2002-04-18
US7169774B2 (en) 2007-01-30
JP2015117251A (ja) 2015-06-25
WO1999048894A1 (en) 1999-09-30
EP1064285A1 (de) 2001-01-03
HUP0101375A2 (hu) 2001-12-28
PT1064285E (pt) 2005-05-31
WO1999048894B1 (en) 1999-11-04
US20050090484A1 (en) 2005-04-28
US6613900B2 (en) 2003-09-02
FR2776292A1 (fr) 1999-09-24
JP4942871B2 (ja) 2012-05-30
CN1220692C (zh) 2005-09-28
JP6087381B2 (ja) 2017-03-01
PL343032A1 (en) 2001-07-30
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