CA2538864C - Thalidomide analogs as tnf-alpha modulators - Google Patents

Thalidomide analogs as tnf-alpha modulators Download PDF

Info

Publication number
CA2538864C
CA2538864C CA2538864A CA2538864A CA2538864C CA 2538864 C CA2538864 C CA 2538864C CA 2538864 A CA2538864 A CA 2538864A CA 2538864 A CA2538864 A CA 2538864A CA 2538864 C CA2538864 C CA 2538864C
Authority
CA
Canada
Prior art keywords
compound
stereoisomer
salt
sulfur
substituted
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.)
Expired - Fee Related
Application number
CA2538864A
Other languages
English (en)
French (fr)
Other versions
CA2538864A1 (en
Inventor
Nigel H. Greig
Harold Holloway
Xiaoxiang Zhu
Tony Giordano
Qian-Sheng Yu
William D. Figg
Arnold Brossi
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.)
P2D Inc
US Department of Health and Human Services
Original Assignee
US Department of Health and Human Services
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 US Department of Health and Human Services filed Critical US Department of Health and Human Services
Priority to CA2808646A priority Critical patent/CA2808646C/en
Publication of CA2538864A1 publication Critical patent/CA2538864A1/en
Application granted granted Critical
Publication of CA2538864C publication Critical patent/CA2538864C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (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 Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Oncology (AREA)
  • Transplantation (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
CA2538864A 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators Expired - Fee Related CA2538864C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2808646A CA2808646C (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US50472403P 2003-09-17 2003-09-17
US60/504,724 2003-09-17
PCT/US2004/030506 WO2005028436A2 (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2808646A Division CA2808646C (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators

Publications (2)

Publication Number Publication Date
CA2538864A1 CA2538864A1 (en) 2005-03-31
CA2538864C true CA2538864C (en) 2013-05-07

Family

ID=34375538

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2538864A Expired - Fee Related CA2538864C (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators
CA2808646A Expired - Fee Related CA2808646C (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2808646A Expired - Fee Related CA2808646C (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators

Country Status (9)

Country Link
US (2) US7973057B2 (enExample)
EP (1) EP1663223B1 (enExample)
JP (1) JP4943845B2 (enExample)
CN (1) CN1867331B (enExample)
AU (1) AU2004274474B2 (enExample)
BR (1) BRPI0414497A (enExample)
CA (2) CA2538864C (enExample)
SG (1) SG133603A1 (enExample)
WO (1) WO2005028436A2 (enExample)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2929331B2 (ja) * 1990-07-18 1999-08-03 丸善石油化学株式会社 トラクションドライブ用流体
AU2005274927B2 (en) 2004-07-15 2011-11-03 Albany Molecular Research, Inc. Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
CN100383139C (zh) * 2005-04-07 2008-04-23 天津和美生物技术有限公司 可抑制细胞释放肿瘤坏死因子的哌啶-2，6-二酮衍生物
CN1939922B (zh) * 2005-09-27 2010-10-13 天津和美生物技术有限公司 可抑制细胞释放肿瘤坏死因子的5H-噻吩[3，4-c]吡咯-4，6-二酮衍生物
US20080064876A1 (en) * 2006-05-16 2008-03-13 Muller George W Process for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
US8877780B2 (en) 2006-08-30 2014-11-04 Celgene Corporation 5-substituted isoindoline compounds
NZ575061A (en) * 2006-08-30 2011-10-28 Celgene Corp 5-substituted isoindoline compounds
AU2008229383B2 (en) * 2007-03-20 2013-09-05 Celgene Corporation 4'-O-substituted isoindoline derivatives and compositions comprising and methods of using the same
AU2013260742B2 (en) * 2007-03-20 2016-06-16 Celgene Corporation 4'-o-substituted isoindoline derivatives and compositions comprising and methods of using the same
US7723301B2 (en) * 2007-08-29 2010-05-25 The Board Of Trustees Of The University Of Arkansas Pharmaceutical compositions comprising an anti-teratogenic compound and applications of the same
US20090298882A1 (en) * 2008-05-13 2009-12-03 Muller George W Thioxoisoindoline compounds and compositions comprising and methods of using the same
US9156812B2 (en) 2008-06-04 2015-10-13 Bristol-Myers Squibb Company Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine
US8802696B2 (en) * 2009-05-12 2014-08-12 Albany Molecular Research, Inc. 7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoqu inoli and use thereof
CN102458123A (zh) 2009-05-12 2012-05-16 阿尔巴尼分子研究公司 芳基、杂芳基和杂环取代的四氢异喹啉及其用途
WO2010132487A1 (en) 2009-05-12 2010-11-18 Bristol-Myers Squibb Company CRYSTALLINE FORMS OF (S)-7-([1,2,4]TRIAZOLO[1,5-a]PYRIDIN-6-YL)-4-(3,4-DICHLOROHPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINE AND USE THEREOF
SG10201501062SA (en) 2010-02-11 2015-04-29 Celgene Corp Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the same
ES2664872T3 (es) * 2010-06-18 2018-04-23 Taiho Pharmaceutical Co., Ltd Moduladores PRPK-TPRKB y sus usos
US8927725B2 (en) 2011-12-02 2015-01-06 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Thio compounds
JP2015500001A (ja) 2011-12-14 2015-01-05 大鵬薬品工業株式会社 組換えｐｒｐｋ−ｔｐｒｋｂ及びその使用
US9383644B2 (en) 2014-09-18 2016-07-05 Heraeus Precious Metals North America Daychem LLC Sulfonic acid derivative compounds as photoacid generators in resist applications
ES2901509T3 (es) 2014-10-30 2022-03-22 Kangpu Biopharmaceuticals Ltd Derivado de isoindolina, compuesto intermedio, métodos de preparación, composición farmacéutica y uso del mismo
US9477150B2 (en) 2015-03-13 2016-10-25 Heraeus Precious Metals North America Daychem LLC Sulfonic acid derivative compounds as photoacid generators in resist applications
CN108025003B (zh) * 2015-07-08 2021-07-13 基尔罗斯制药有限公司 前额叶皮质处理病症，步态和肢体障碍治疗
AU2016330967B2 (en) 2015-09-30 2021-03-25 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Thalidomide analogs and methods of use
CA3017740A1 (en) 2016-03-16 2017-09-21 Pearlie BURNETTE Small molecules against cereblon to enhance effector t cell function
CA3045703C (en) * 2016-11-24 2021-11-02 Tianjin Hemay Bio-Tech Co., Ltd Piperidine-2,6-dione derivatives and ulcerative colitis treating
KR20200086278A (ko) 2017-10-18 2020-07-16 노파르티스 아게 선택적 단백질 분해를 위한 조성물 및 방법
EA202190248A1 (ru) 2018-07-11 2021-06-16 Х. Ли Моффитт Кэнсер Сентер Энд Рисерч Инститьют, Инк. Димерные иммуномодулирующие соединения против механизмов на основе цереблона
US11324731B2 (en) 2018-09-13 2022-05-10 City Of Hope TXNIP-TRX complex inhibitors and methods of using the same
CN113423701A (zh) 2018-11-13 2021-09-21 拜欧斯瑞克斯公司 取代的异吲哚啉酮
WO2020124500A1 (zh) * 2018-12-20 2020-06-25 江苏凯迪恩医药科技有限公司 一种含氮杂环化合物、其制备方法及应用
US12582641B2 (en) 2019-02-25 2026-03-24 Shanghaitech University Sulfur-containing compound based on glutarimide skeleton and application thereof
EP3959320A1 (en) 2019-04-24 2022-03-02 Novartis AG Compositions and methods for selective protein degradation
CN112321566B (zh) 2019-08-05 2022-06-10 上海科技大学 Egfr蛋白降解剂及其抗肿瘤应用
US20220388978A1 (en) * 2019-08-27 2022-12-08 Regents Of The University Of Michigan Cereblon e3 ligase inhibitors
KR102783667B1 (ko) 2019-10-24 2025-03-21 삼성전자 주식회사 전자 장치 및 그의 디스플레이 동작 제어 방법
WO2021138391A1 (en) 2019-12-30 2021-07-08 Tyra Biosciences, Inc. Indazole compounds
WO2021143822A1 (zh) * 2020-01-16 2021-07-22 江苏恒瑞医药股份有限公司 并环酰亚胺类衍生物、其制备方法及其在医药上的应用
CN113372327B (zh) * 2020-02-25 2023-07-18 上海科技大学 基于戊二酰亚胺骨架的化合物及其应用
KR102943446B1 (ko) * 2020-10-26 2026-04-01 주식회사 아이비스바이오 포말리도마이드로부터 3,6'-디티오포말리도마이드를 선택적으로 합성하는 방법
US20240166647A1 (en) * 2021-03-03 2024-05-23 The Regents Of The University Of Michigan Cereblon Ligands
EP4484418A4 (en) * 2022-02-25 2026-01-14 Aevis Bio Inc USE OF A NEW POMALIDOMIDE DERIVATIVE TO TREAT BRAIN DISEASES
PE20251697A1 (es) 2022-11-04 2025-07-02 Bristol Myers Squibb Co Compuestos y su uso para el tratamiento de hemoglobinopatias
EP4745135A1 (en) * 2023-07-14 2026-05-20 Gluetacs Therapeutics Shanghai Co Ltd ISOINDOLINONE THIO-GLUTARIMIDO SKELETAL COMPOUND AND ITS USES

Family Cites Families (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2830991A (en) * 1954-05-17 1958-04-15 Gruenenthal Chemie Products of the amino-piperidine-2-6-dione series
GB962857A (en) 1961-12-04 1964-07-08 Distillers Co Yeast Ltd Process for the production of imides
GB1049283A (en) * 1962-04-14 1966-11-23 Distillers Co Yeast Ltd Substituted butyro-lactones and -thiolactones
US3320270A (en) * 1963-10-08 1967-05-16 Tri Kem Corp Certain 2-acylimidothiazole compounds
US3314953A (en) * 1964-03-16 1967-04-18 Richardson Merrell Inc 1-substituted-3-phthalimido-2, 5-dioxopyrrolidines
IL25595A (en) 1965-05-08 1971-01-28 Gruenenthal Chemie New history of cyclic amide compounds and process for the production of these compounds
US3560495A (en) * 1965-05-08 1971-02-02 Ernst Frankus 1-heterocyclic amino methyl or 1-heterocyclic hydrazino methyl-3-phthalimido or (3',6'-dithia-3',4',5',6'-tetrahydrophthalimido)-pyrrolidinediones-2,5 or piperidinediones-2,6
GB1324718A (en) * 1970-11-10 1973-07-25 Nehezvegyipari Kutato Intezet Phthalimido triazines
US4067718A (en) * 1975-11-12 1978-01-10 American Cyanamid Company Method for controlling the relative stem growth of plants
US4291048A (en) * 1978-07-06 1981-09-22 Joseph Gold Method of treating tumors and cancerous cachexia with L-tryptophan
US5354690A (en) * 1989-07-07 1994-10-11 Karl Tryggvason Immunological methods for the detection of the human type IV collagen α5 chain
US5902790A (en) 1995-10-03 1999-05-11 Cytran, Inc. Pharmaceutical angiostatic dipeptide compositions and method of use thereof
GB9311281D0 (en) * 1993-06-01 1993-07-21 Rhone Poulenc Rorer Ltd Novel composition of matter
WO1992018496A1 (de) 1991-04-17 1992-10-29 Grünenthal GmbH Neue thalidomidderivate, ein verfahren zu deren herstellung sowie die verwendung derselben in arzneimitteln
US6096768A (en) * 1992-01-28 2000-08-01 Rhone-Poulenc Rorer Limited Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group
US6228879B1 (en) * 1997-10-16 2001-05-08 The Children's Medical Center Methods and compositions for inhibition of angiogenesis
US5629327A (en) * 1993-03-01 1997-05-13 Childrens Hospital Medical Center Corp. Methods and compositions for inhibition of angiogenesis
US20010056114A1 (en) * 2000-11-01 2001-12-27 D'amato Robert Methods for the inhibition of angiogenesis with 3-amino thalidomide
US5434170A (en) 1993-12-23 1995-07-18 Andrulis Pharmaceuticals Corp. Method for treating neurocognitive disorders
US5443824A (en) * 1994-03-14 1995-08-22 Piacquadio; Daniel J. Topical thalidomide compositions for surface or mucosal wounds, ulcerations, and lesions
DE4422237A1 (de) * 1994-06-24 1996-01-04 Gruenenthal Gmbh Verwendung von Lactamverbindungen als pharmazeutische Wirkstoffe
US5789434A (en) * 1994-11-15 1998-08-04 Bayer Corporation Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors
US6429221B1 (en) 1994-12-30 2002-08-06 Celgene Corporation Substituted imides
JPH10511678A (ja) 1994-12-30 1998-11-10 セルジーン コーポレイション 免疫治療用イミド類／アミド類およびＴＮＦαのレベルを減少させるためのこれらの使用
US5783605A (en) * 1995-02-27 1998-07-21 Kuo; Sheng-Chu Helper inducers for differentiation therapy and chemoprevention of cancer
US5728844A (en) 1995-08-29 1998-03-17 Celgene Corporation Immunotherapeutic agents
CA2251060C (en) 1996-04-09 2006-09-12 Grunenthal Gmbh Acylated n-hydroxy methyl thalidomide prodrugs with immunomodulator action
DE19613976C1 (de) * 1996-04-09 1997-11-20 Gruenenthal Gmbh Thalidomid-Prodrugs mit immunmodulatorischer Wirkung
CZ389398A3 (cs) 1996-05-29 1999-07-14 Prototek, Inc. Proléčiva thalidomidu a jejich použití pro modulaci funkce T-buněk
PT2177517E (pt) 1996-07-24 2011-11-10 Celgene Corp 2-(2,6-dioxopiperidin-3-il)-ftalimida amino-substituída para redução dos níveis de tnf-alfa
US5635517B1 (en) 1996-07-24 1999-06-29 Celgene Corp Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines
DE69734290T2 (de) 1996-11-05 2006-07-06 The Children's Medical Center Corp., Boston Mittel zur hemmung von angiogenese enthaltend thalodomid und einen nsaid
BR9714394A (pt) 1996-12-13 2000-05-16 Lilly Co Eli Inibidores da atividade enzimática de psa
DE19703763C1 (de) 1997-02-01 1998-10-01 Gruenenthal Gmbh Thalidomidanaloge Verbindungen aus der Klasse der Piperidin-2,6-Dione
RU2108786C1 (ru) 1997-09-15 1998-04-20 Клавдия Степановна Евланенкова Средство для лечения онкологических больных
DE19743968C2 (de) 1997-10-06 2002-07-11 Gruenenthal Gmbh Intravenöse Applikationsform von Thalidomid zur Therapie immunologischer Erkrankungen
AU749356B2 (en) 1998-05-11 2002-06-27 Children's Medical Center Corporation Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis
CN1188389C (zh) 1998-05-15 2005-02-09 阿斯特拉曾尼卡有限公司 用于治疗由细胞因子引起的疾病的苯甲酰胺衍生物
DE19843793C2 (de) * 1998-09-24 2000-08-03 Gruenenthal Gmbh Substituierte Benzamide
US20030013739A1 (en) * 1998-12-23 2003-01-16 Pharmacia Corporation Methods of using a combination of cyclooxygenase-2 selective inhibitors and thalidomide for the treatment of neoplasia
DK1040838T3 (da) 1999-03-31 2003-05-26 Gruenenthal Gmbh Stabil vandig opløsning af 3-(1-oxo-1,3-dihydroisoindol-2-yl )piperidin-2,6-dion
AU4515001A (en) * 1999-12-02 2001-06-18 Regents Of The University Of Michigan, The Compositions and methods for locally treating inflammatory diseases
US6458810B1 (en) * 2000-11-14 2002-10-01 George Muller Pharmaceutically active isoindoline derivatives
NZ526683A (en) 2000-11-30 2008-03-28 Childrens Medical Center Synthesis of 4-amino-thalidomide and its enantiomers that are suitable for inhibiting angiogenesis
US20030045552A1 (en) * 2000-12-27 2003-03-06 Robarge Michael J. Isoindole-imide compounds, compositions, and uses thereof
EP1389203B8 (en) * 2001-02-27 2010-03-10 The Governement of the United States of America, represented by The Secretary Department of Health and Human services Analogs of thalidomide as angiogenesis inhibitors
NZ531294A (en) 2001-08-06 2005-11-25 Childrens Medical Center Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs
EP1336602A1 (en) 2002-02-13 2003-08-20 Giovanni Scaramuzzino Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases
EP2272513A1 (en) 2002-05-17 2011-01-12 Celgene Corporation Pharmaceutical compositions for treating cancer
CN100488959C (zh) 2003-03-27 2009-05-20 天津和美生物技术有限公司 水溶性的酞胺哌啶酮衍生物
WO2005016326A2 (en) 2003-07-11 2005-02-24 The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Analogs of thalidomide as potential angiogenesis inhibitors

Also Published As

Publication number Publication date
AU2004274474A1 (en) 2005-03-31
CA2808646A1 (en) 2005-03-31
EP1663223B1 (en) 2014-01-01
SG133603A1 (en) 2007-07-30
US8546430B2 (en) 2013-10-01
CA2538864A1 (en) 2005-03-31
BRPI0414497A (pt) 2006-11-14
CA2808646C (en) 2016-08-23
JP2007505922A (ja) 2007-03-15
WO2005028436A2 (en) 2005-03-31
JP4943845B2 (ja) 2012-05-30
US20060211728A1 (en) 2006-09-21
WO2005028436A3 (en) 2005-05-19
US20110245210A1 (en) 2011-10-06
AU2004274474B2 (en) 2011-03-10
CN1867331A (zh) 2006-11-22
CN1867331B (zh) 2010-05-26
US7973057B2 (en) 2011-07-05
EP1663223A2 (en) 2006-06-07

Similar Documents

Publication Publication Date Title
CA2808646C (en) Thalidomide analogs as tnf-alpha modulators
US8853253B2 (en) Thalidomide analogs
US10220028B2 (en) Thio compounds
JP5156378B2 (ja) ＭＤＭ２とｐ５３の間の相互作用の阻害剤
CA2433021C (en) Isoindole-imide compounds, compositions, and uses thereof
CA3215907A1 (en) Substituted 2-(2,6-dioxopiperidin-3-yl)-5-(1-piperidin-4-yl)isoindoline-1,3-dione derivatives and uses thereof
CN117143175A (zh) 靶向sos1蛋白泛素化调节的化合物及其制备方法和应用
TW201031642A (en) N3 alkylated benzimidazole derivative as MEK inhibitors
EP2094681A1 (en) Indol-4-yl-pyrimidinyl-2-yl-amine derivatives and use thereof as cyclin dependant kinase inhibitors
MX2015002807A (es) Alcoxipirazoles como activadores de guanilato ciclasa soluble.
CN113454081A (zh) 咪唑并吡啶基化合物及其用于治疗增生性疾病的用途
TW200916458A (en) Heterocyclic compounds and methods of use thereof
CN103140134B (zh) 新吡咯烷衍生的β3肾上腺素能受体激动剂
Brink et al. Design and synthesis of conformationally restricted inhibitors of active thrombin activatable fibrinolysis inhibitor (TAFIa)
JP7782023B2 (ja) Ａｈｒアゴニスト
JPH1135545A (ja) ウレタン誘導体
TW536538B (en) Phthalimido arylpiperazines useful in the treatment of benign prostatic hyperplasia
KR20240066906A (ko) 퀴놀린 아마이드 구조를 갖는 이소인돌리논 유도체 및 이의 용도
JP2811962B2 (ja) ピリジン化合物およびその医薬用途
EP0825180A1 (en) 1-omega-(3,4-dihydro-2-naphthalenyl)alkyl] cyclic amine derivatives, process for producing the same, and medicinal composition containing the same
HK40058867A (en) Imidazopyridinyl compounds and use thereof for treatment of proliferative disorders

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20210917