DE3034843A1 - Verfahren zur herstellung von 10-deazaminopterin und dessen 10-alkylderivate - Google Patents

Verfahren zur herstellung von 10-deazaminopterin und dessen 10-alkylderivate

Info

Publication number
DE3034843A1
DE3034843A1 DE19803034843 DE3034843A DE3034843A1 DE 3034843 A1 DE3034843 A1 DE 3034843A1 DE 19803034843 DE19803034843 DE 19803034843 DE 3034843 A DE3034843 A DE 3034843A DE 3034843 A1 DE3034843 A1 DE 3034843A1
Authority
DE
Germany
Prior art keywords
alkyl
acid
reaction
group
deazaminopterin
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.)
Granted
Application number
DE19803034843
Other languages
German (de)
English (en)
Other versions
DE3034843C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html
Inventor
Joseph Irving Sunnyvale Calif. De Graw
Francis Michael New York City N.Y. Sirotnak
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.)
SRI International Inc
Memorial Sloan Kettering Cancer Center
Original Assignee
SRI International Inc
Memorial Sloan Kettering Cancer Center
Stanford Research Institute
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 SRI International Inc, Memorial Sloan Kettering Cancer Center, Stanford Research Institute filed Critical SRI International Inc
Publication of DE3034843A1 publication Critical patent/DE3034843A1/de
Application granted granted Critical
Publication of DE3034843C2 publication Critical patent/DE3034843C2/de
Granted legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D475/00—Heterocyclic compounds containing pteridine ring systems
    • C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
    • C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
DE19803034843 1979-09-17 1980-09-16 Verfahren zur herstellung von 10-deazaminopterin und dessen 10-alkylderivate Granted DE3034843A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US06/075,913 US4393064A (en) 1976-03-05 1979-09-17 Process and composition for treatment of leukemia and process for preparing the same
US06/233,280 US4369319A (en) 1979-09-17 1981-02-10 10-Alkyl-10-deazaminopterins
US06/344,564 US4433147A (en) 1979-09-17 1982-01-22 Process for preparing 10-deazaminopterins

Publications (2)

Publication Number Publication Date
DE3034843A1 true DE3034843A1 (de) 1981-06-11
DE3034843C2 DE3034843C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1989-10-05

Family

ID=27372768

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19803034843 Granted DE3034843A1 (de) 1979-09-17 1980-09-16 Verfahren zur herstellung von 10-deazaminopterin und dessen 10-alkylderivate

Country Status (9)

Country Link
US (3) US4393064A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (2) JPS5651482A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU540326B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
BE (1) BE885255A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA1139752A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE3034843A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (2) FR2464956A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB2058770B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ZA (1) ZA805474B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5140104A (en) * 1982-03-09 1992-08-18 Cytogen Corporation Amine derivatives of folic acid analogs
US4684653A (en) * 1985-03-08 1987-08-04 The Trustees Of Princeton University Pyrido(2,3-d)pyrimidine derivatives
US4927828A (en) * 1985-03-08 1990-05-22 The Trustees Of Princeton University Diastereoisomeric tetrahydropyrido-(2,3,d) pyrimidine derivatives
US5026851A (en) * 1985-03-08 1991-06-25 The Trustees Of Princeton University Pyrido[2,3-]pyrimidine derivatives
JPS6237911A (ja) * 1985-08-12 1987-02-18 Sumitomo Special Metals Co Ltd 異方性フエライト磁石
US4746659A (en) * 1985-12-30 1988-05-24 Sri International Diastereomers of 10-alkyl-10-deazaminopterins and process for preparing the same
JPS62281878A (ja) * 1986-02-26 1987-12-07 Taisho Pharmaceut Co Ltd アザアントラセン化合物
US4833145A (en) * 1986-06-30 1989-05-23 The Trustees Of Princeton University 4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine derivatives
US4902796A (en) * 1986-10-20 1990-02-20 The Trustees Of Princeton University 6-alkenyl and ethynyl derivatives of 2-amino-4-hydroxypyrido[2,3-d]pyrimidines
US4818819A (en) * 1986-10-20 1989-04-04 The Trustees Of Princeton University Process for the preparation of fused pyridine compounds
US4767761A (en) * 1987-11-04 1988-08-30 Dana-Farber Cancer Institute, Inc. Ornithine derivatives and their use as methotrexate-resistant cell inhibitors
US4935427A (en) * 1987-12-31 1990-06-19 The United States Of America As Represented By The Department Of Health And Human Services Pyrimidine and purine 1,2-butadiene-4-ols as anti-retroviral agents
US5019577A (en) * 1988-04-15 1991-05-28 Burroughs Welcome Co. Novel compounds and use
US4940713A (en) * 1988-04-15 1990-07-10 Burroughs Wellcome Co. Substituted glutamic acids
FR2640638B1 (fr) * 1988-12-20 1991-02-15 Commissariat Energie Atomique Bioreacteur et dispositif pour la culture de cellules animales
JPH03118740A (ja) * 1989-09-29 1991-05-21 Hitachi Metals Ltd アークセグメント磁石
US5028608A (en) * 1989-12-11 1991-07-02 The Trustees Of Princeton University N-(6-Amino-(pyrrolo(2,3-d)pyrimidin-3-ylacyl) )-glutamic acid derivatives
US4996207A (en) * 1990-01-18 1991-02-26 Nair Madhavan G Three new non-polyglutamatable deazaaminopterins
US5073554A (en) * 1990-01-18 1991-12-17 Nair Madhavan G Two non-polyglutamatable antifolates
US5030634A (en) * 1990-03-29 1991-07-09 Krumdieck Carlos L 10-deazaaminopterin: a new arthritis remittive drug
US5286726A (en) * 1990-04-12 1994-02-15 The Regents Of The University Of Michigan Difluoroglutamic acid conjugates with folates and anti-folates for the treatment of neoplastic diseases
US5159079A (en) * 1991-12-20 1992-10-27 Eli Lilly And Company 2-piperidones as intermediates for 5-deaza-10-oxo- and 5-deaza-10-thio-5,6,7,8-tetrahydrofolic acids
US5354751A (en) * 1992-03-03 1994-10-11 Sri International Heteroaroyl 10-deazaamino-pterine compounds and use for rheumatoid arthritis
US5374726A (en) * 1992-03-03 1994-12-20 Degraw; Joseph I. Process for preparing 10-deazaaminopterins and 5,10-and 8,10-dideazaaminopterins from pteroic dicarboxylic acid diesters
WO1993022315A1 (en) * 1992-04-29 1993-11-11 Sri International Heteroaroyl-10-deazaaminopterins for treatment of inflammation
US5260296A (en) * 1992-05-13 1993-11-09 Nair Madhavan G Thiophene substituted antitumor antifolates
US5534514A (en) * 1992-10-27 1996-07-09 San Diego State University Anti-neoplastic compositions and methods for application thereof
US5550128A (en) * 1994-09-09 1996-08-27 Nair; Madhavan G. Enantiomers of gamma methylene 10-deaza aminopterin and process for preparing the same
US6262054B1 (en) 1996-02-01 2001-07-17 Sloan-Kettering Institute Of Cancer Research Combination therapy method for treating breast cancer using edatrexate
US6028071A (en) * 1996-07-17 2000-02-22 Sloan-Kettering Institute For Cancer Research Purified compositions of 10-propargyl-10-deazaaminopterin and methods of using same in the treatment of tumors
WO1998024789A1 (en) * 1996-12-02 1998-06-11 Bionumerik Pharmaceuticals, Inc. PROCESS FOR MAKING η-METHYLENE-10-DEAZAAMINOPTERIN (MDAM)
DE69920757T2 (de) * 1998-12-28 2005-12-15 4 AZA Bioscience N.V. Immunosuppressive wirkungen von pteridinderivaten
EP1469847A1 (en) 2002-01-14 2004-10-27 Novartis AG Combinations comprising epothilones and anti-metabolites
US20040092739A1 (en) * 2002-11-13 2004-05-13 Zejun Xiao Process for synthesizing antifolates
AU2005249516B2 (en) * 2004-05-30 2010-11-18 Sloan-Kettering Institute For Cancer Research Treatment of T-cell lymphoma using 10-propargyl-10-deazaaminopterin
US20080188479A1 (en) * 2004-05-30 2008-08-07 Sloan-Kettering Institute For Cancer Research Methods to Treat Cancer with 10-propargyl-10-deazaaminopterin and Methods for Assessing Cancer for Increased Sensitivity to 10-propargyl-10-deazaaminopterin
US8263354B2 (en) * 2004-05-30 2012-09-11 Sloan-Kettering Institute For Cancer Research Methods for assessing cancer for increased sensitivity to 10-propargyl-10-deazaaminopterin
WO2009026234A1 (en) * 2007-08-17 2009-02-26 Allos Therapeutics, Inc. Combination of 10-propargyl-10-deazaaminopterin and erlotinib for the treatment of non-small cell lung cancer
US20100248249A1 (en) * 2007-08-17 2010-09-30 Allos Therapeutics, Inc. Methods for Assessing Cancer for Increased Sensitivity to 10-Propargyl-10-Deazaaminopterin by Assessing Egfr Levels
US9901578B2 (en) 2007-08-17 2018-02-27 Allos Therapeutics, Inc. Combination of 10-propargyl-10-deazaaminopterin and erlotinib for the treatment of non-small cell lung cancer
WO2011096947A1 (en) * 2010-02-02 2011-08-11 Allos Therapeutics, Inc. Optically pure diastereomers of 10-propargyl-10-deazaaminopterin and methods of using same
CN103265544B (zh) * 2013-05-27 2015-05-20 苏州明锐医药科技有限公司 普拉曲沙的制备方法
CN103274943B (zh) * 2013-05-24 2015-01-21 苏州明锐医药科技有限公司 4-[1-(2-丙炔基)-3,4-二氧代正丁基]苯甲酸酯及其制备方法
WO2024204738A1 (ja) * 2023-03-30 2024-10-03 持田製薬株式会社 １，１－ジメチル－１，２－ジヒドロナフタレンの製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2709506A1 (de) * 1976-03-05 1977-09-08 Stanford Research Inst Arzneimittel, enthaltend 10-deazaminopterin

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4172200A (en) * 1978-06-15 1979-10-23 Southern Research Institute Process for the preparation of 10-deazaaminopterin and related compounds

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2709506A1 (de) * 1976-03-05 1977-09-08 Stanford Research Inst Arzneimittel, enthaltend 10-deazaminopterin

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Chemistry and Biologie of Pteridines, Verlag Elsevier, North Holland, New York 1979, S. 225-228 *
Journal Heterocyclic Chemistry, Bd. 8, 1971, S. 105-110 *
Journal of Medicinal Chemistry, 14, 1974, S. 866-867 *
Journal of Medicinal Chemistry, 17, 1974, S. 552-555 *
Journal of Medicinal Chemistry, 25, 1982, S. 1227-1230 *
The Chemistry of Carbon-Carbon triple bond, Part 1, John Wiley and Sons, New York 1978, S. 381-389 *

Also Published As

Publication number Publication date
JPH0334979A (ja) 1991-02-14
JPH0340029B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1991-06-17
JPH034553B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1991-01-23
JPS5651482A (en) 1981-05-09
GB2058770B (en) 1983-05-25
BE885255A (fr) 1981-01-16
AU540326B2 (en) 1984-11-15
FR2477152A1 (fr) 1981-09-04
US4369319A (en) 1983-01-18
GB2058770A (en) 1981-04-15
US4393064A (en) 1983-07-12
AU6243980A (en) 1981-03-26
ZA805474B (en) 1981-08-26
US4433147A (en) 1984-02-21
FR2477152B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1983-03-11
FR2464956A1 (fr) 1981-03-20
DE3034843C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1989-10-05
FR2464956B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1983-04-29
CA1139752A (en) 1983-01-18

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Legal Events

Date Code Title Description
8128 New person/name/address of the agent

Representative=s name: MUELLER, H., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN

8110 Request for examination paragraph 44
D2 Grant after examination
8364 No opposition during term of opposition
8339 Ceased/non-payment of the annual fee