CN104736540B - 培美曲塞及其赖氨酸盐的制备方法 - Google Patents

培美曲塞及其赖氨酸盐的制备方法 Download PDF

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Publication number
CN104736540B
CN104736540B CN201380041935.8A CN201380041935A CN104736540B CN 104736540 B CN104736540 B CN 104736540B CN 201380041935 A CN201380041935 A CN 201380041935A CN 104736540 B CN104736540 B CN 104736540B
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China
Prior art keywords
pemetrexed
salt
water
lysine
acid
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Chinese (zh)
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CN104736540A (zh
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F·博纳科尔西
F·卡尔瓦尼
F·帕斯奎
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Berlin Chemie AG
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Berlin Chemie AG
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    • 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
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CN201380041935.8A 2012-08-08 2013-08-08 培美曲塞及其赖氨酸盐的制备方法 Active CN104736540B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT000398A ITRM20120398A1 (it) 2012-08-08 2012-08-08 Procedimento di sintesi pemetrexed e suo sale di lisina.
ITRM2012A000398 2012-08-08
PCT/IB2013/056497 WO2014024164A1 (en) 2012-08-08 2013-08-08 Process for the preparation of pemetrexed and lysin salt thereof

Publications (2)

Publication Number Publication Date
CN104736540A CN104736540A (zh) 2015-06-24
CN104736540B true CN104736540B (zh) 2017-08-25

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CN201380041935.8A Active CN104736540B (zh) 2012-08-08 2013-08-08 培美曲塞及其赖氨酸盐的制备方法

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EP (1) EP2882753B1 (enExample)
KR (1) KR102288417B1 (enExample)
CN (1) CN104736540B (enExample)
AU (1) AU2013301156B2 (enExample)
BR (1) BR112015002429A8 (enExample)
CY (1) CY1118514T1 (enExample)
DK (1) DK2882753T3 (enExample)
ES (1) ES2607890T3 (enExample)
HR (1) HRP20170011T1 (enExample)
HU (1) HUE032304T2 (enExample)
IN (1) IN2015DN00833A (enExample)
IT (1) ITRM20120398A1 (enExample)
LT (1) LT2882753T (enExample)
MX (1) MX362858B (enExample)
PL (1) PL2882753T3 (enExample)
PT (1) PT2882753T (enExample)
RS (1) RS55515B1 (enExample)
RU (1) RU2609006C2 (enExample)
SI (1) SI2882753T1 (enExample)
SM (2) SMT201600474T1 (enExample)
TW (1) TWI609017B (enExample)
WO (1) WO2014024164A1 (enExample)
ZA (1) ZA201501549B (enExample)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107641124A (zh) * 2016-07-22 2018-01-30 上海创诺制药有限公司 一种培美曲塞二酸新晶型及其制备方法
CN109836425B (zh) * 2017-11-24 2023-01-24 江苏创诺制药有限公司 一种合成培美酸的制备工艺
EP3749317A4 (en) 2018-02-07 2022-06-22 L.E.A.F Holdings Group LLC PEMETREXED ALPHA-POLYGLUTAMATE AND ASSOCIATED USES
WO2019157145A1 (en) 2018-02-07 2019-08-15 L.E.A.F. Holdings Group Llc Gamma polyglutamated pemetrexed and uses thereof
CN110128427A (zh) * 2018-02-09 2019-08-16 鲁南制药集团股份有限公司 培美曲塞缬氨酸盐
CN110128428A (zh) * 2018-02-09 2019-08-16 鲁南制药集团股份有限公司 培美曲塞丙氨酸盐
CN110128426B (zh) * 2018-02-09 2021-12-14 鲁南制药集团股份有限公司 培美曲塞谷氨酸盐
CN111333658A (zh) * 2020-05-06 2020-06-26 贵州联科中贝制药科技有限公司 一种培美曲塞二钠水合物的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1087910A (zh) * 1992-09-25 1994-06-15 伊莱利利公司 5-取代的吡咯并[2，3-d]嘧啶的制备方法
EP2301909A1 (en) * 2008-05-30 2011-03-30 Shanghai Cdymax Pharmaceuticals Co., Ltd Processes for preparing pemetrexed disodium and its intermediate,4-(4-carbomethoxyphenyl)butanal
CN102344452A (zh) * 2010-07-22 2012-02-08 凯米股份公司 合成培美曲塞二钠盐的新方法
WO2012056285A1 (en) * 2010-10-25 2012-05-03 Fresenius Kabi Oncology Ltd. An improved process for the preparation of pemetrexed

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0440795B1 (en) 1988-10-31 1994-10-19 MITSUI TOATSU CHEMICALS, Inc. Process for preparing organic group-substituted sodium aluminum hydride
KR0162654B1 (ko) 1989-12-11 1998-11-16 알렌 제이. 시니스갤리 N-(피롤로[2,3-d]피리미딘-3-일아크릴)-글루타민산 유도체
IL96531A (en) 1989-12-11 1995-08-31 Univ Princeton History of Acid N- (Diomeric-H1-Pyrolo] D-2,3 [Pyrimidine-3-Ilacyl (-glutamic, preparation and pharmaceutical preparations containing them)
US5416211A (en) 1992-09-25 1995-05-16 Eli Lilly And Company Process for preparing 5-substituted pyrrolo-[2,3-d]pyrimidines
DE19725647A1 (de) 1997-06-18 1998-12-24 Basf Ag Cyclopenta[I]phenanthren-Metallkomplex-Katalysatorsysteme
ZA987550B (en) 1997-09-26 2000-02-21 Lilly Co Eli Processes and intermediates useful to make antifolates.
KR100744917B1 (ko) 2000-02-25 2007-08-01 일라이 릴리 앤드 캄파니 신규한 결정형의Ｎ-[4-[2-(2-아미노-4,7-디히드로-4-옥소-3Ｈ-피롤로[2,3-ｄ]피리미딘-5-일)에틸]벤조일]-Ｌ-글루탐산 및 이의 제조방법
EP1957497B1 (en) * 2006-08-14 2015-09-30 Sicor, Inc. Processes for preparing intermediates of pemetrexed
WO2008021410A2 (en) * 2006-08-14 2008-02-21 Sicor Inc. Highly pure pemetrexed diacid and processes for the preparation thereof
US9655898B2 (en) 2010-07-28 2017-05-23 Eagle Pharmaceuticals, Inc. Pharmaceutical compositions containing pemetrexed having extended storage stability

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1087910A (zh) * 1992-09-25 1994-06-15 伊莱利利公司 5-取代的吡咯并[2，3-d]嘧啶的制备方法
EP2301909A1 (en) * 2008-05-30 2011-03-30 Shanghai Cdymax Pharmaceuticals Co., Ltd Processes for preparing pemetrexed disodium and its intermediate,4-(4-carbomethoxyphenyl)butanal
CN102344452A (zh) * 2010-07-22 2012-02-08 凯米股份公司 合成培美曲塞二钠盐的新方法
WO2012056285A1 (en) * 2010-10-25 2012-05-03 Fresenius Kabi Oncology Ltd. An improved process for the preparation of pemetrexed

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
A New and Efficient Synthesis of Pyrrolo[2,3-d]pyrimidine Anticancer Agents: Alimta (LY231514, MTA), Homo-Alimta,TNP-351, and Some Aryl 5-Substituted Pyrrolo[2,3-d]pyrimidines;Edward C. Taylor，等;《J. Org. Chem.》;20031122;第68卷(第26期);第9938-9947页 *
A Novel Synthetic Approach to Pyrrolo[2,3-d]pyrimidine Antifolates;Tetauo Miwa，等;《Journal of Organic Chemistry》;19931231;第58卷(第7期);第1696-1701页 *
A Practical Synthesis of Multitargeted Antifolate LY231514;Charles J. Barnett，等;《Organic Process Research & Development》;19990430;第3卷(第3期);第184-188页 *

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Publication number Publication date
BR112015002429A2 (pt) 2017-07-04
SI2882753T1 (sl) 2017-02-28
RU2015108042A (ru) 2016-09-27
TW201412741A (zh) 2014-04-01
DK2882753T3 (en) 2017-01-16
MX2015001712A (es) 2015-08-14
SMT201600474B (it) 2017-03-08
HRP20170011T1 (hr) 2017-03-10
PT2882753T (pt) 2016-12-27
HK1209426A1 (en) 2016-04-01
SMT201600474T1 (it) 2017-03-08
PL2882753T3 (pl) 2017-04-28
KR102288417B1 (ko) 2021-08-11
IN2015DN00833A (enExample) 2015-06-12
EP2882753B1 (en) 2016-10-05
AU2013301156B2 (en) 2017-08-31
ZA201501549B (en) 2016-01-27
AU2013301156A1 (en) 2015-02-05
KR20150045458A (ko) 2015-04-28
TWI609017B (zh) 2017-12-21
MX362858B (es) 2019-02-20
LT2882753T (lt) 2016-12-12
ITRM20120398A1 (it) 2014-02-09
RS55515B1 (sr) 2017-05-31
EP2882753A1 (en) 2015-06-17
WO2014024164A1 (en) 2014-02-13
BR112015002429A8 (pt) 2019-07-30
RU2609006C2 (ru) 2017-01-30
CY1118514T1 (el) 2017-07-12
ES2607890T3 (es) 2017-04-04
HUE032304T2 (en) 2017-09-28
CN104736540A (zh) 2015-06-24

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