KR930703243A - 방향족 설폰아미드계 하이드록삼산 유도체 - Google Patents

방향족 설폰아미드계 하이드록삼산 유도체

Info

Publication number
KR930703243A
KR930703243A KR1019930702373A KR930702373A KR930703243A KR 930703243 A KR930703243 A KR 930703243A KR 1019930702373 A KR1019930702373 A KR 1019930702373A KR 930702373 A KR930702373 A KR 930702373A KR 930703243 A KR930703243 A KR 930703243A
Authority
KR
South Korea
Prior art keywords
unsubstituted
alkylene
substituted
pharmaceutically acceptable
compound
Prior art date
Application number
KR1019930702373A
Other languages
English (en)
Other versions
KR100236806B1 (ko
Inventor
미쯔아끼 오따니
히또시 아리따
겐지 스기따
다까하루 마쯔우라
가즈히로 시라하세
Original Assignee
시오노 요시히꼬
시오노기 세이야꾸 가부시끼가이샤
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 시오노 요시히꼬, 시오노기 세이야꾸 가부시끼가이샤 filed Critical 시오노 요시히꼬
Publication of KR930703243A publication Critical patent/KR930703243A/ko
Application granted granted Critical
Publication of KR100236806B1 publication Critical patent/KR100236806B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—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

Landscapes

  • 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)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

본 발명은 하기 일반식(Ⅰ)로 표시되는 화합물 또는 그의 약학적으로 허용가능한 염을 유효 성분으로서 함유한, 세포증식 억제 작용, 혈관 신생 억제 작용 등을 갖는 신규한 하이드록삼산 유도체에 관한 것이다.
상기식에서, [A]는 각각 비치환되거나 치환된 방향족 또는 방향족 헤테로환이고, A는 수소 또는 각각 비치환되거나 치환된 아릴 또는 방향족 헤테로 환이며,B는 단일 결합을 나타내거나 -B1-B2-로 표시되는 2가지이고, B1은 -CO- 또는 -SO2-를 나타내고, B2는 알킬렌, 알케닐렌, 알킬렌옥시 또는 알케닐렌옥시를 나타내며, X는 비치환되거나 치환된 알킬렌이고, 이 알킬렌은 쇄중에 O, S 또는 N의 헤테로 원자가 포함될 수 있으며, 또한 불포화 결합을 가질 수도 있고, Y는 단일 결합, 헤테로 원자 또는 비치환되거나 치환된 알키렌이며, 이 알킬렌은 쇄중에 헤테로 원자가 함유될 수 있으며, 또한 불포화 결합을 가질 수도 있고, X는 Y에 결합된 질소원자와 함께
의 5원 이상의 질소함유 헤테로 환을 형성할 수 있고, R1, R2및 R3는 각각 독립적으로 수소이거나, 비치환되거나 치환된 저급알킬 또는 아릴기를 나타낸다.
본 발명의 화합물은 혈관내피세포 증식 억제 작용, 임파구 접착인자 발현 억제작용 및 ras유전자에 의해 형질전환된 세포의 탈형질 작용을 가지며, 세포증식을 억제하고, 염증 및 종양에 효과적이다.

Description

방향족 설폰아미드계 하이드록삼산 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (4)

  1. 하기 일반식(Ⅰ)로 표시되는 화합물 또는 그의 약학적으로 허용가능한 염;
    상기식에서, [A]는 각각 비치환되거나 치환된 방향족 또는 방향족 헤테로환이고, A는 수소 또는 각각 비치환되거나 치환된 아릴 또는 방향족 헤테로 환이며, B는 단일 결합을 나타내거나 -B1-B2- 로 표시되는 2가지이고, B1은 -CO- 또는 -SO2-를 나타내고, B2는 알킬렌, 알케닐렌, 알킬렌옥시 또는 알케닐렌옥시를 나타내며, X는 비치환되거나 치환된 알킬렌이고, 이 알킬렌은 쇄중에 O,S 또는 N의 헤테로 원자가 포함될 수 있으며, 또한 불포화 결합을 가질 수도 있고, Y는 단일 결합, 헤테로 원자 또는 비치환되거나 치환된 알킬렌이며, 이 알킬렌은 쇄중에 헤테로 원자가 함유될 수 있으며, 또한 불포화 결합을 가질 수도 있고, X는 Y에 결합된 질소원자와 함께
    의 5원 이상의 질소함유 헤테로 환을 형성할 수 있고, R1, R2및 R3는 각각 독립적으로 수소이거나, 비치환되거나 치환된 저급알킬 또는 아릴기를 나타낸다.
  2. 제1항에 있어서, 5원 이상의 질소 함유 헤테로 환이 피롤인 화합물.
  3. 제1항에 기재된 일반식(Ⅰ)의 화합물과 약학적으로 허용가능한 담체를 포함하는 항종양제.
  4. 제1항에 기재된 일반식(Ⅰ)의 화합물과 약학적으로 허용가능한 담체를 포함하는 소염제.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930702373A 1991-12-10 1992-12-07 방향족 설폰아미드계 하이드록삼산 유도체 KR100236806B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP35079391 1991-12-10
JP91-350793 1991-12-10
PCT/JP1992/001593 WO1993012075A1 (en) 1991-12-10 1992-12-07 Hydroxamic acid derivative based on aromatic sulfonamide

Publications (2)

Publication Number Publication Date
KR930703243A true KR930703243A (ko) 1993-11-29
KR100236806B1 KR100236806B1 (ko) 2000-01-15

Family

ID=18412912

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019930702373A KR100236806B1 (ko) 1991-12-10 1992-12-07 방향족 설폰아미드계 하이드록삼산 유도체

Country Status (10)

Country Link
US (1) US5534654A (ko)
EP (1) EP0570594B1 (ko)
JP (1) JP3342485B2 (ko)
KR (1) KR100236806B1 (ko)
AT (1) ATE156116T1 (ko)
DE (1) DE69221290T2 (ko)
DK (1) DK0570594T3 (ko)
ES (1) ES2107557T3 (ko)
GR (1) GR3024740T3 (ko)
WO (1) WO1993012075A1 (ko)

Families Citing this family (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE207057T1 (de) * 1994-04-06 2001-11-15 Nippon Shinyaku Co Ltd Aminostilbazolderivate und medikament
US6777217B1 (en) 1996-03-26 2004-08-17 President And Fellows Of Harvard College Histone deacetylases, and uses related thereto
AR011057A1 (es) * 1997-01-08 2000-08-02 Smithkline Beecham Corp Uso de bis-acridinas sustituidas y compuestos afines para la preparacion de medicamentos y dichos compuestos
AUPO721997A0 (en) * 1997-06-06 1997-07-03 Queensland Institute Of Medical Research, The Anticancer compounds
CA2360740A1 (en) 1999-03-02 2000-09-08 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cathepsin s
JP2001026506A (ja) * 1999-04-28 2001-01-30 Takeda Chem Ind Ltd スルホンアミド誘導体
US6586617B1 (en) * 1999-04-28 2003-07-01 Sumitomo Chemical Takeda Agro Company, Limited Sulfonamide derivatives
WO2000069465A1 (fr) * 1999-05-12 2000-11-23 Ono Pharmaceutical Co., Ltd. Agents anticancereux contenant des antagonistes de ep1 en tant que principe actif
US6420364B1 (en) 1999-09-13 2002-07-16 Boehringer Ingelheim Pharmaceuticals, Inc. Compound useful as reversible inhibitors of cysteine proteases
CA2391952C (en) 1999-11-23 2012-01-31 Methylgene Inc. Inhibitors of histone deacetylase
US20030129724A1 (en) 2000-03-03 2003-07-10 Grozinger Christina M. Class II human histone deacetylases, and uses related thereto
EP1752446A3 (en) * 2000-04-13 2007-03-21 HSC Research and Development Limited Partnership Compounds for modulating cell proliferation
AU4820101A (en) * 2000-04-13 2001-10-30 Hsc Res Dev Lp Novel compounds for modulating cell proliferation
PE20020354A1 (es) * 2000-09-01 2002-06-12 Novartis Ag Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda)
EP2083005A1 (en) * 2000-09-29 2009-07-29 TopoTarget UK Limited Carbamic acid compounds comprising an amide linkage as HDAC inhibitors
GB0023983D0 (en) 2000-09-29 2000-11-15 Prolifix Ltd Therapeutic compounds
WO2002030879A2 (en) 2000-09-29 2002-04-18 Prolifix Limited Carbamic acid compounds comprising a sulfonamide linkage as hdac inhibitors
US7312247B2 (en) 2001-03-27 2007-12-25 Errant Gene Therapeutics, Llc Histone deacetylase inhibitors
US8026280B2 (en) * 2001-03-27 2011-09-27 Errant Gene Therapeutics, Llc Histone deacetylase inhibitors
US6495719B2 (en) * 2001-03-27 2002-12-17 Circagen Pharmaceutical Histone deacetylase inhibitors
US6727277B1 (en) 2002-11-12 2004-04-27 Kansas State University Research Foundation Compounds affecting cholesterol absorption
AU2003291097A1 (en) * 2002-11-20 2004-06-15 Errant Gene Therapeutics, Llc Treatment of lung cells with histone deacetylase inhibitors
WO2004056319A2 (en) * 2002-12-19 2004-07-08 Elan Pharmaceuticals Inc. Substituted n-phenyl sulfonamide bradykinin antagonists
TW200418806A (en) 2003-01-13 2004-10-01 Fujisawa Pharmaceutical Co HDAC inhibitor
US7652036B2 (en) 2003-02-25 2010-01-26 Topotarget Uk Limited Carbamic acid compounds comprising a bicyclic heteroaryl group as HDAC inhibitors
WO2005066151A2 (en) * 2003-12-19 2005-07-21 Takeda San Diego, Inc. Histone deacetylase inhibitors
WO2005061448A1 (en) * 2003-12-24 2005-07-07 Monash University Compositions and methods for treating vascular conditions
NZ549251A (en) 2004-03-11 2010-05-28 4Sc Ag Sulphonylpyrroles as HDAC inhibitors
EP1727822A4 (en) 2004-03-26 2007-05-09 Hsc Res Dev Lp NEW COMPOUNDS FOR MODULATING CELL PROLIFERATION
WO2006075888A1 (en) * 2005-01-14 2006-07-20 Sk Corporation Oxazole hydroxamic acid derivatives and use thereof
MX2007010561A (es) 2005-03-15 2008-02-22 Nycomed Gmbh N-sulfonilpirroles y su uso como inhibidores de la histona desacetilasa.
WO2006102557A2 (en) 2005-03-22 2006-09-28 The President And Fellows Of Harvard College Treatment of protein degradation disorders
CA2603398A1 (en) * 2005-04-07 2006-10-12 Nycomed Gmbh Sulfonylpyrroles as histone deacetylase inhibitors
CN102675221A (zh) 2005-09-16 2012-09-19 武田药品工业株式会社 用于制备嘧啶二酮衍生物的方法中的中间体
BRPI0617167B8 (pt) 2005-09-21 2021-05-25 Nycomed Gmbh sulfonilpirróis como inibidores de hdac's, seu uso, composição farmacêutica e combinação
NZ566073A (en) * 2005-09-21 2011-08-26 4Sc Ag Sulphonylpyrrole hydrochloride salts as histone deacetylases inhibitors
CN101379059A (zh) 2006-02-07 2009-03-04 安斯泰来制药有限公司 N-羟基丙烯酰胺化合物
CN101400362B (zh) 2006-02-14 2016-10-12 哈佛大学校长及研究员协会 双官能组蛋白去乙酰化酶抑制剂
TW200838536A (en) 2006-11-29 2008-10-01 Takeda Pharmaceutical Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor
CN101417967A (zh) * 2007-10-26 2009-04-29 浙江海正药业股份有限公司 组蛋白去乙酰酶抑制剂、其组合物及其应用
EP2100878A1 (en) 2008-03-12 2009-09-16 4Sc Ag Novel method for the production of sulphonylpyrroles as HDAC inhibitors
JP5665740B2 (ja) 2008-07-23 2015-02-04 プレジデント アンド フェローズ オブ ハーバード カレッジ デアセチラーゼ阻害剤およびその使用
JP5773877B2 (ja) * 2008-10-22 2015-09-02 アキュセラ インコーポレイテッド 眼の疾患及び障害を治療する化合物
US8716344B2 (en) 2009-08-11 2014-05-06 President And Fellows Of Harvard College Class- and isoform-specific HDAC inhibitors and uses thereof
CA2862259A1 (en) * 2011-12-29 2013-07-04 Pharmacyclics, Inc. Cinnamic acid hydroxyamides as inhibitors of histone deacetylase 8
PE20160901A1 (es) 2013-12-18 2016-08-27 Astex Therapeutics Ltd Reguladores de nrf2
EP3268358A1 (en) 2015-03-13 2018-01-17 Forma Therapeutics, Inc. Alpha-cinnamide compounds and compositions as hdac8 inhibitors
KR20180018684A (ko) 2015-06-15 2018-02-21 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 Nrf2 조절제
WO2016202253A1 (en) 2015-06-15 2016-12-22 Glaxosmithkline Intellectual Property Development Limited Nrf2 regulators
EP3359532A1 (en) 2015-10-06 2018-08-15 GlaxoSmithKline Intellectual Property Development Limited Biaryl pyrazoles as nrf2 regulators
EP3461488A1 (en) 2017-09-27 2019-04-03 Onxeo Combination of a dbait molecule and a hdac inhibitor for treating cancer
EP3461480A1 (en) 2017-09-27 2019-04-03 Onxeo Combination of a dna damage response cell cycle checkpoint inhibitors and belinostat for treating cancer
WO2021148581A1 (en) 2020-01-22 2021-07-29 Onxeo Novel dbait molecule and its use
WO2023041805A1 (en) 2021-09-20 2023-03-23 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods for improving the efficacy of hdac inhibitor therapy and predicting the response to treatment with hdac inhibitor
WO2023194441A1 (en) 2022-04-05 2023-10-12 Istituto Nazionale Tumori Irccs - Fondazione G. Pascale Combination of hdac inhibitors and statins for use in the treatment of pancreatic cancer
KR20240047155A (ko) 2022-10-04 2024-04-12 유영훈 열선용 커넥션 키트

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2984077B2 (ja) * 1990-04-19 1999-11-29 塩野義製薬株式会社 スルホニルアミノ置換ビシクロ環系ヒドロキサム酸誘導体

Also Published As

Publication number Publication date
EP0570594A1 (en) 1993-11-24
ATE156116T1 (de) 1997-08-15
DE69221290T2 (de) 1998-01-15
DE69221290D1 (de) 1997-09-04
KR100236806B1 (ko) 2000-01-15
JP3342485B2 (ja) 2002-11-11
ES2107557T3 (es) 1997-12-01
US5534654A (en) 1996-07-09
GR3024740T3 (en) 1997-12-31
EP0570594A4 (en) 1994-05-18
WO1993012075A1 (en) 1993-06-24
DK0570594T3 (ko) 1997-08-25
EP0570594B1 (en) 1997-07-30

Similar Documents

Publication Publication Date Title
KR930703243A (ko) 방향족 설폰아미드계 하이드록삼산 유도체
KR920002596A (ko) 아지비사이클로 유도체
KR900018098A (ko) 피리돈 카르복실산과 항균제
DK490288A (da) Substituerede thiazolidindionderivater
FI906204A (fi) Menetelmä farmaseuttisesti vaikuttavien peptidiyhdisteiden valmistamiseksi
KR927003520A (ko) 펩티딜(peptidyl) 유도체
KR930703303A (ko) 1, 4-벤조티아제핀 유도체
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
EP0371805A3 (en) Piperidine derivatives and hypotensives containing the same
ATE182331T1 (de) Oxazolidone derivative als monoamine- oxidaseinhibitoren
KR940005620A (ko) 에이즈의 치료에 유용한 에이치아이브이(hiv) 프로테아제 억제제
DK0408044T3 (da) Antiinflammatorisk og/eller antiallergisk præparat, der omfatter glutathionderivater
KR940009163A (ko) 벤질리덴 유도체
KR920701240A (ko) 글루타티온 유도체
DE3668888D1 (de) Ein imidazolidintrion-derivat oder ein seiner pharmazeutisch akzeptierbaren salze enthaltende pharmazeutische zusammenstellung.
MX9206930A (es) Nuevos compuestos
KR890008121A (ko) 로다닌 유도체 및 약제학적 조성물
KR850005228A (ko) 살균제인 아미노알칸포스폰산 및 그 유도체
DE3889208T2 (de) Thioformamid-Derivate.
KR880011141A (ko) 신규한 화합물
DK92486D0 (da) 1-0xa-1-dethiacephalosporinforbindelse
KR910006217A (ko) 디히드로카페인산 유도체 및 이를 함유하는 약학제제
KR930703275A (ko) 벤조옥사디논유도체
EP0370712A3 (en) Ethylamine derivatives and hypotensives containing the same
KR900009076A (ko) 디하이드로피리딘 화합물을 함유하는 정맥 신전도 증진제 및 심장 비대 억제제

Legal Events

Date Code Title Description
A201 Request for examination
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
LAPS Lapse due to unpaid annual fee