KR910011890A - N-(피롤로[2,3-d]피리미딘-3-일아크릴)-글루타민산 유도체 - Google Patents

N-(피롤로[2,3-d]피리미딘-3-일아크릴)-글루타민산 유도체 Download PDF

Info

Publication number
KR910011890A
KR910011890A KR1019900020549A KR900020549A KR910011890A KR 910011890 A KR910011890 A KR 910011890A KR 1019900020549 A KR1019900020549 A KR 1019900020549A KR 900020549 A KR900020549 A KR 900020549A KR 910011890 A KR910011890 A KR 910011890A
Authority
KR
South Korea
Prior art keywords
hydrogen
compound
methyl
glutamic acid
hydroxy
Prior art date
Application number
KR1019900020549A
Other languages
English (en)
Other versions
KR0162654B1 (ko
Inventor
시. 테일러 에드워드
씨이 츄안
말지. 쿠혼트 다이에트
비. 그린데이 제랄드
Original Assignee
원본미기재
더 트라스티 오브 프린스턴 유니버스티
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27035466&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=KR910011890(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from US07/528,805 external-priority patent/US4996206A/en
Application filed by 원본미기재, 더 트라스티 오브 프린스턴 유니버스티 filed Critical 원본미기재
Publication of KR910011890A publication Critical patent/KR910011890A/ko
Application granted granted Critical
Publication of KR0162654B1 publication Critical patent/KR0162654B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Abstract

내용 없음

Description

N-(피롤로[2,3-d]피리미딘-3-일아크릴)-글루타민산 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (17)

  1. 하기 일반식의 화합물 및 그들의 약학적 허용염:
    상기식중, R1은 -OH 또는 -NH2,R3은 비치환되거나 클로로, 플루오로, 메틸, 메톡시 또는 트리플루오로메틸로 치환된 1,4-페닐렌 또는 1,3-페닐렌, 비치환되거나 클로로, 플루오로, 메틸, 메톡시 또는 트리플루오로메틸로 치환된 티엔디일 또는 푸린디일, 시클로헥실디일, 및 알칸디일, R4는 수소, 메틸, 또는 히드록시메틸, 및 R5는 수소 또는 탄소수 1 내지 6의 알킬,*로 표시된 탄소원자주위의 구조는 S이다.
  2. 제1항에 있어서, R1이 -OH, R3가 1,4-페닐렌, R4가 수소 및 R5가 수소인 화합물.
  3. 제1항에 있어서, R1이 -OH, R3가 1,4-페닐렌, R4가 수소 및 R5가 메틸인 화합물.
  4. 제1항에 있어서, R1이 -OH, R3가 티엔디일, R4가 수소 및 R5가 수소인 화합물.
  5. 제1항에 있어서, R1이 -OH, R3가 티엔디일, R4가 수소 및 R5가 메틸인 화합물.
  6. 제1항에 있어서, N-{4-[2-(4-히드록시피롤로[2,3-d]피리미딘-3-일)에틸]벤조일]-L-글루타민산인 화합물.
  7. 제1항에 있어서, N-{4-[2-(4-히드록시-6-메틸피롤로[2,3-d]피리미딘-3-일)에틸]벤조일]-L-글루타민산인 화합물.
  8. 하기 일반식의 화합물 및 그들의 약학적 허용염:
    상기식중, R5는 아미노 또는 탄소수 1 내지 12의 알카노일아민이고, *로 표시된 탄소원자주위의 구조는 S이다.
  9. 제8항에 있어서, N-{4-[2-(4-히드록시-6-아미노 피롤로[2,3-d]피리미딘-3-일)에틸]벤조일]-L-글루타민산인 화합물.
  10. 제8항에 있어서, N-{4-[2-(4-히드록시-6-아미노피롤로[2,3-d]피리미딘-3-일)에틸]벤조일]-L-글루타민산인 화합물.
  11. 포유동물에 일회 또는 다수회의 규정식이 투여시 신생물을 억제시키는데 유효한 분량의 N-{4-[2-(4-히드록시-6-아미노피롤로[2,3-d]피리미딘-3-일)에틸]벤조일]-L-글루타민산 또는 그들의 약학적허용염과 약학적허용담체를 포함하는, 티미딜레이트 합성효소의 억제를 통해 포유동물의 신생물성장을 억제시키는 약학조성물.
  12. 인간을 제외한 포유동물에 유효량의 제8항의 화합물을 일회 또는 다수회로 규정식이 투여하는 것으로 구성되는 포유동물의 신생물 성장억제방법.
  13. 하기 일반식의 화합물 및 그들의 약학적 허용염:
    상기식중, R1은 -OH 또는 -NH2,R3은 비치환되거나 클로로, 플루오로, 메틸, 메톡시 또는 트리플루오로메틸로 치환된 티엔디일, 또는 푸린디일, 시클로헥사디일, 및 알칸디일, R4는 수소, 메틸, 또는 히드록시메틸, 및*로 표시된 탄소원자주위의 구조는 S이다.
  14. 제13항에 있어서, R1이 -OH, R3가 티엔디일 및 R4가 수소 및 R5가 수소인 화합물.
  15. 제13항에 있어서, N-{5-[2-(4-히드록시-6-아미노피롤로[2,3-d]피리미딘-3-일)에틸]티엔-2-일카르보닐}-L-글루타민산,N-{4-[2-(4-히드록시-6-아미노피롤로[2,3-d]피리미딘-3-일)에틸]티엔-2-일카르보닐}-L-글루타민산, 또는 N-{5-[2-(4-히드록시-6-아미노피롤로[2,3-d]피리미딘-3-일)에틸]티엔-2-일카르보닐}-L-글루타민산인 화합물.
  16. 하기 일반식(A)의 화합물을 촉매적으로 수소화시켜서 하기일반식(B)의 화합물을 제조하고, X=COOR2인 경우에는 보호된 글루타민산과 반응시켜서
    인 화합물로 형성시킨후, 보호기를 제거하는 것으로 구성되는 하기 일반식(I) 화합물의 제조방법:
    상기식중, R1은 -OH 또는 -NH2,R2은 수소 또는 약학적허용양이온, R3은 비치환되거나 클로로, 플루오로, 메틸, 메톡시 또는 트리플루오로메틸로 치환된 1,4-페닐렌 또는 1,3-페닐렌, 비치환되거나 클로로, 플루오로, 메틸, 메톡시 또는 트리플루오로메틸로 치환된 티엔디일 또는 푸란디일, 시클로헥실디일 또는 알칸디일, R4는 수소, 메틸, 또는 히드록시메틸, 및 R5는 수소 또는 탄소수 1 내지 6의 알킬,*로 표시된 탄소원자주위의 구조는 S이고
    은 수소, 또는 R4'와 함께 탄소-탄소결합을 형성하고, R2'는 수소 또는 카르복시보호기, R4',Z'과 함께 결합을 형성하지 않는 경우에는 수소 메틸, 히드록시메틸, 또는 히드록시보호로 치환된 히드록시메틸, R5'는 수소, 탄소수 1 내지 6의 알킬, 아미노, 또는 아미노보호기, R6은 수소 또는 알카노일옥시이다.
  17. 제16항에 있어서, 일반식(I)의 화합물이 N-{4-[2-(4-히드록시-6-아미노피롤로[2,3-d]피리미딘-3-일)에틸]벤조일}-L-글루타민산 및 그들의 약학적 허용염인 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900020549A 1989-12-11 1990-12-11 N-(피롤로[2,3-d]피리미딘-3-일아크릴)-글루타민산 유도체 KR0162654B1 (ko)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US44874289A 1989-12-11 1989-12-11
US448,742 1989-12-11
US47965590A 1990-02-08 1990-02-08
US479,655 1990-02-08
US07/528,805 US4996206A (en) 1989-12-11 1990-05-24 N-(pyrrolo[2,3-d]pyrimidin-3-ylacyl)-glutamic acid derivatives
US528,805 1990-05-24
US07/528,155 US5028608A (en) 1989-12-11 1990-05-24 N-(6-Amino-(pyrrolo(2,3-d)pyrimidin-3-ylacyl) )-glutamic acid derivatives
US528,155 1990-05-24

Publications (2)

Publication Number Publication Date
KR910011890A true KR910011890A (ko) 1991-08-07
KR0162654B1 KR0162654B1 (ko) 1998-11-16

Family

ID=27035466

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019900020549A KR0162654B1 (ko) 1989-12-11 1990-12-11 N-(피롤로[2,3-d]피리미딘-3-일아크릴)-글루타민산 유도체

Country Status (3)

Country Link
US (1) US5344932A (ko)
KR (1) KR0162654B1 (ko)
SA (1) SA94150191B1 (ko)

Families Citing this family (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5958930A (en) * 1991-04-08 1999-09-28 Duquesne University Of The Holy Ghost Pyrrolo pyrimidine and furo pyrimidine derivatives
US5877178A (en) * 1991-04-08 1999-03-02 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
US5508281A (en) * 1991-04-08 1996-04-16 Duquesne University Of The Holy Ghost Derivatives of pyrido [2,3-d] and [3,2-d] pyrimidine and methods of using these derivatives
US5939420A (en) * 1991-04-08 1999-08-17 Duquesne University Of The Holy Ghost Pyrrolo 2,3d!derivatives
WO1992017478A1 (en) * 1991-04-08 1992-10-15 Duquesne University Of The Holy Ghost 5-ALKYL-6-[[AMINO]METHYL]PYRIDO[2,3-d]PYRIMIDINE DERIVATIVES AND METHODS OF PREPARING AND USING THESE DERIVATIVES
US6962920B2 (en) * 1992-09-23 2005-11-08 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
IL107041A (en) * 1992-09-25 2000-02-17 Lilly Co Eli Process for preparing omega(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo-6-¬2,3-d¾pyrimidin-5-YL)alkarylcarboxylic acids and N-(omega-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo¬2,3-d¾pyrimidin-5-YL)alk-aroyl-4-glutamic acids
US6537999B2 (en) 1996-06-06 2003-03-25 Duquesne University Of The Holy Ghost Pyrimidine derivatives and methods of making and using these derivatives
US7863444B2 (en) 1997-03-19 2011-01-04 Abbott Laboratories 4-aminopyrrolopyrimidines as kinase inhibitors
WO1999041230A1 (en) 1998-02-11 1999-08-19 Eli Lilly And Company Processes and intermediates useful to make antifolates
US6713474B2 (en) 1998-09-18 2004-03-30 Abbott Gmbh & Co. Kg Pyrrolopyrimidines as therapeutic agents
US7071199B1 (en) 1999-09-17 2006-07-04 Abbott Gmbh & Cco. Kg Kinase inhibitors as therapeutic agents
SK3812002A3 (en) 1999-09-17 2003-09-11 Abbott Gmbh & Co Kg Pyrazolopyrimidines as therapeutic agents
TR200401436T4 (tr) * 2000-02-04 2004-07-21 Eli Lilly And Company Monotiyogliserol, L-sistem veya tiyoglikolik asitle birlikte pemetrexed içeren farmasötik bileşim
US6686365B2 (en) * 2000-02-04 2004-02-03 Eli Lilly And Company Pharmaceutical composition
CZ303772B6 (cs) * 2000-02-25 2013-05-02 Eli Lilly And Company Heptahydrátová krystalická forma disodné soli N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]-benzoyl]L-glutamové kyseliny a zpusob její prípravy
WO2002002093A2 (en) * 2000-06-30 2002-01-10 Eli Lilly And Company Combination containing an antifolate and methylmalonic acid lowering agent
JP2004529880A (ja) * 2001-02-16 2004-09-30 イーライ・リリー・アンド・カンパニー 抗ウイルス剤としての使用方法
CN100364993C (zh) * 2003-05-30 2008-01-30 江苏恒瑞医药股份有限公司 培美曲噻盐及其制备方法
JP2008512490A (ja) * 2004-09-08 2008-04-24 チェルシー・セラピューティクス，インコーポレイテッド 異常細胞増殖および炎症の障害を治療するための代謝的に不活性な葉酸拮抗剤
US20080221135A1 (en) * 2005-05-13 2008-09-11 Bristol-Myers Squibb Company Combination therapy
EP1754484A1 (en) 2005-08-17 2007-02-21 Dan Stoicescu Condensed pyrimidine derivatives as inhibitors of foic acid-dependent enzymes
WO2007056135A1 (en) * 2005-11-04 2007-05-18 Merck & Co., Inc. Method of treating cancers with saha and pemetrexed
EP1942907A2 (en) * 2005-11-04 2008-07-16 Merck and Co., Inc. Methods of using saha and erlotinib for treating cancer
AU2007204410A1 (en) * 2006-01-12 2007-07-19 Novartis Ag Combination of mTOR inhibitor and antipolate compound
US8629152B2 (en) * 2006-08-14 2014-01-14 Sicor, Inc. Processes for the preparation of lyophilized pharmaceutically acceptable salts of pemetrexed diacid
US7994180B2 (en) 2006-08-14 2011-08-09 Sicor Inc. Processes for preparing intermediates of pemetrexed
EP2322526A1 (en) * 2006-08-14 2011-05-18 Sicor, Inc. Crystalline form of pemetrexed diacid and process for the preparation thereof
EP1934226A2 (en) 2006-08-14 2008-06-25 Sicor, Inc. Highly pure pemetrexed diacid and processes for the preparation thereof
WO2008057456A2 (en) * 2006-11-03 2008-05-15 University Of Maryland, Baltimore Methods of using saha and bortezomib for treating multiple myeloma
JP2010516694A (ja) * 2007-01-19 2010-05-20 チェルシー・セラピューティクス，インコーポレイテッド 新規な伝統的葉酸拮抗剤
EP1958632A1 (en) * 2007-02-14 2008-08-20 Dan Stoicescu Use of condensed pyrimidine derivatives for the treatment of autoimmune and inflammatory diseases
JP2010523589A (ja) * 2007-04-03 2010-07-15 ドクター レディズ ラボラトリーズ リミテッド ペメトレキセドの固体形
US20090069349A1 (en) * 2007-09-12 2009-03-12 Protia, Llc Deuterium-enriched pemetrexed
WO2009126637A1 (en) * 2008-04-07 2009-10-15 Chelsea Therapeutics, Inc. Antifolate compositions
WO2010030598A2 (en) * 2008-09-11 2010-03-18 Dr. Reddy's Laboratories Limited Pharmaceutical formulations comprising pemetrexed
CN101684121B (zh) * 2008-09-22 2013-04-03 重庆医药工业研究院有限责任公司 培美曲塞二酸的新晶型及其制备方法
JP2012532877A (ja) * 2009-07-08 2012-12-20 チェルシー・セラピューティクス，インコーポレイテッド （ｓ）−２−｛４−［２−（２，４−ジアミノ−キナゾリン−６−イル）−エチル］−ベンゾイルアミノ｝−４−メチレン−ペンタン二酸の二カリウム塩の安定な結晶多形
WO2011056957A2 (en) * 2009-11-06 2011-05-12 Chelsea Therapeutics, Inc. Enzyme inhibiting compounds
WO2012064377A1 (en) * 2010-03-29 2012-05-18 Chelsea Therapeutics, Inc. Antifolate compositions
US20130183268A1 (en) 2010-07-19 2013-07-18 Bayer Healthcare Llc Drug combinations with fluoro-substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions
IT1401677B1 (it) 2010-07-22 2013-08-02 Chemi Spa Nuovo processo per la sintesi di pemetrexed sale disodico
UA105580C2 (uk) 2010-08-02 2014-05-26 Неон Лабораторіс Лтд. Спосіб одержання діалкілпеметрекседу високої чистоти
WO2012056285A1 (en) 2010-10-25 2012-05-03 Fresenius Kabi Oncology Ltd. An improved process for the preparation of pemetrexed
WO2012078708A1 (en) 2010-12-07 2012-06-14 Chelsea Therapeutics, Inc. Combination comprising methotrexate and an antifolate compound
US10736969B2 (en) 2010-12-21 2020-08-11 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of pemetrexed-based compounds
IN2012DE00912A (ko) 2012-03-27 2015-09-11 Fresenius Kabi Oncology Ltd
EP2666463A1 (en) 2012-05-21 2013-11-27 Synthon BV Stabilized liquid composition comprising pemetrexed
SI2854768T1 (sl) 2012-05-30 2017-08-31 Fresenius Kabi Oncology Limited Farmacevtski sestavki pemetrekseda
ITRM20120398A1 (it) 2012-08-08 2014-02-09 Berlin Chemie Ag Procedimento di sintesi pemetrexed e suo sale di lisina.
CN102911175B (zh) * 2012-08-21 2015-04-15 南京亚东启天药业有限公司 2-氨基-4-羰基-7-(3,4-二甲氧苯甲基)-5-乙烯基-6,7-二氢-3H-吡咯并[2,3-d]嘧啶的制法
KR101260636B1 (ko) 2012-11-29 2013-05-13 씨제이제일제당 (주) 안정화된 페메트렉시드 제제
EP2953616A2 (en) 2013-02-06 2015-12-16 Cipla House Pemetrexed complexes and pharmaceutical compositions containing pemetrexed complexes
KR101485243B1 (ko) 2013-05-08 2015-01-21 씨제이헬스케어 주식회사 안정화된 페메트렉시드 제제
EP3008064B1 (en) 2013-06-14 2017-11-22 Synthon B.V. Stable pemetrexed arginine salt and compositions comprising it
JP2016527227A (ja) 2013-07-16 2016-09-08 ドクター レディズ ラボラトリーズ リミテッド ペメトレキセドトロメタミン塩の新規な結晶形
KR101578093B1 (ko) 2013-09-05 2015-12-16 주식회사 삼양바이오팜 고순도 페메트렉세드 제조를 위한 향상된 중간체 제조 방법 및 이를 사용하여 고순도 페메트렉세드를 제조하는 방법
US20170340639A1 (en) 2015-03-26 2017-11-30 Ftf Pharma Private Limited Pharmaceutical composition of pemetrexed
KR101693675B1 (ko) 2015-12-14 2017-01-06 주식회사 종근당 페메트렉시드 또는 그의 약제학적으로 허용가능한 염을 함유하는 안정화된 약학조성물
PL3402503T3 (pl) 2016-01-13 2021-04-19 Acerta Pharma B.V. Kombinacje terapeutyczne antyfolianu oraz inhibitora btk
ES2914123T3 (es) 2017-01-09 2022-06-07 Shuttle Pharmaceuticals Inc Inhibidores selectivos de la histona desacetilasa para el tratamiento de una enfermedad humana
US11584733B2 (en) 2017-01-09 2023-02-21 Shuttle Pharmaceuticals, Inc. Selective histone deacetylase inhibitors for the treatment of human disease
US20200246263A1 (en) 2017-08-29 2020-08-06 Fresenius Kabi Oncology Limited Stable liquid compositions of pemetrexed
WO2019139921A1 (en) 2018-01-09 2019-07-18 Shuttle Pharmaceuticals, Inc. Selective histone deacetylase inhibitors for the treatment of human disease

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4889859A (en) * 1988-02-05 1989-12-26 The Trustees Of Princeton University Pyrido[2,3-d]pyrimidine derivatives
NO169490C (no) * 1988-03-24 1992-07-01 Takeda Chemical Industries Ltd Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolopyrimidinderivater
US4996206A (en) * 1989-12-11 1991-02-26 The Trustees Of Princeton University N-(pyrrolo[2,3-d]pyrimidin-3-ylacyl)-glutamic acid derivatives

Also Published As

Publication number Publication date
KR0162654B1 (ko) 1998-11-16
US5344932A (en) 1994-09-06
SA94150191B1 (ar) 2006-09-20

Similar Documents

Publication Publication Date Title
KR910011890A (ko) N-(피롤로[2,3-d]피리미딘-3-일아크릴)-글루타민산 유도체
ES8204739A1 (es) Un procedimiento para preparar compuestos de cefem
OA09039A (fr) Acides 3-alcenyl-1-azabicyclo(3.2.0)hep-2-ene-2carboxyliques
ATE172731T1 (de) Pyrazolopyridinverbindung und verfahren zu ihrer herstellung
ATE109149T1 (de) 3-pyrrolidinylthio-1-azabicyclo(3.2.0>-hept-2-e - 2-carbonsäureverbindungen.
KR890005124A (ko) 세펨 화합물 및 이의 제조방법
AU2736088A (en) Pharmaceutical compositions comprising benzylidene- and cinnamylidene-malononitrile derivatives for the inhibition of proliferative processes in mammalian cells, certain such novel compounds and their preparation
NO810479L (no) Fremgangsmaate for fremstilling av terapeutisk aktive substituerte imidazolderivater
KR870700067A (ko) 피리도(2,3-d)-피리미딘 유도체
EP1484059A3 (en) Antiviral composition comprising phenylacetic acid derivatives
IE861875L (en) Poly-4-aminopyrrole-2-carboxamido derivatives
KR940009184A (ko) 피라졸 축합환 유도체, 이의 제조방법 및 안드로겐 억제제
EP0186023A3 (en) Biliary acid derivatives, process for their preparation and pharmaceutical compositions containing them
NO161620C (no) Analogifremgangsm te for fremstilling av terapeutisk aktive 8-alkyltio-2-piperazino-pyrimido(5,4-d)pyrimidin-derivater.
KR900018100A (ko) N-(5,6,7,8-테트라히드로피리도(2,3,-d)피리미딘-6-일-알카노일)-글루탐산 유도체 및 그의 제조방법
KR840004753A (ko) 3-아미노-6-아릴-1,2,4-트리아졸로[4,3-b] 피리다진의 제조방법
US3681351A (en) CERTAIN 5,6,7,8-TETRAHYDRO-5,8-ETHANO-PYRIDINO{8 2,3-b{9 -THIENO{8 5,4-d{9 PYRIMIDINES
ZA858030B (en) Thiadiazole derivatives active on the central nervous system,process for their preparation and pharmaceutical compositions in which they are present
KR970010756A (ko) 엔도테린 수용체 길항제
FR2455598A1 (fr) Nouveaux derives 5- (2- ((2,3-dihydro-1,4-benzodioxanne-2-ylmethyl)- amino)-1- hydroxyethyl)-2-hydroxybenzoiques, utiles notamment comme agents bloquants des recepteurs adrenergiques a et b, et leur procede de preparation
KR920008035A (ko) 타이로신 유도체 및 그 제조방법
ES8305319A1 (es) "procedimiento para la preparacion de acidos antranilicos sustituidos con radicales basicos"
JPS5620577A (en) 4- n-alkylanilino quinazoline derivative and its preparation
GB1164496A (en) 0-Oxaphenanthridine Derivatives and Method for the Preparation
ATE25968T1 (de) 1,1-diphenylpropanol-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen.

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20120628

Year of fee payment: 15

EXPY Expiration of term