CA2808646C - Thalidomide analogs as tnf-alpha modulators - Google Patents

Thalidomide analogs as tnf-alpha modulators Download PDF

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Publication number
CA2808646C
CA2808646C CA2808646A CA2808646A CA2808646C CA 2808646 C CA2808646 C CA 2808646C CA 2808646 A CA2808646 A CA 2808646A CA 2808646 A CA2808646 A CA 2808646A CA 2808646 C CA2808646 C CA 2808646C
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CA
Canada
Prior art keywords
substituted
compound
sulfur
alkyl
hydrogen
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
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CA2808646A
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English (en)
French (fr)
Other versions
CA2808646A1 (en
Inventor
Tony Giordano
Arnold Brossi
Nigel H. Greig
Harold Holloway
Xiaoxiang Zhu
Qian-Sheng Yu
William D. Figg
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P2D Inc
US Department of Health and Human Services
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P2D Inc
US Department of Health and Human Services
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Publication of CA2808646A1 publication Critical patent/CA2808646A1/en
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Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • 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

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  • 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)
CA2808646A 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators Expired - Fee Related CA2808646C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US50472403P 2003-09-17 2003-09-17
US60/504,724 2003-09-17
CA2538864A CA2538864C (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2538864A Division CA2538864C (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators

Publications (2)

Publication Number Publication Date
CA2808646A1 CA2808646A1 (en) 2005-03-31
CA2808646C true CA2808646C (en) 2016-08-23

Family

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Family Applications (2)

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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 Before (1)

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CA2538864A Expired - Fee Related CA2538864C (en) 2003-09-17 2004-09-17 Thalidomide analogs as tnf-alpha modulators

Country Status (9)

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

Families Citing this family (42)

* 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
US7541357B2 (en) 2004-07-15 2009-06-02 Amr Technology, 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
JP5523831B2 (ja) * 2006-08-30 2014-06-18 セルジーン コーポレイション ５−置換イソインドリン化合物
AU2013260742B2 (en) * 2007-03-20 2016-06-16 Celgene Corporation 4'-o-substituted isoindoline derivatives and compositions comprising and methods of using the same
MX2009010082A (es) 2007-03-20 2009-10-19 Celgene Corp Derivados y composiciones que comprenden isoindolina 4'-o-sustituida y metodos para utilizar la misma.
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
WO2009139880A1 (en) * 2008-05-13 2009-11-19 Celgene Corporation Thioxoisoindoline compounds and compositions 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
JP5739415B2 (ja) 2009-05-12 2015-06-24 ブリストル−マイヤーズ スクウィブ カンパニー （Ｓ）−７−（［１，２，４］トリアゾロ［１，５−ａ］ピリジン−６−イル）−４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロイソキノリンの結晶形態およびその使用
ES2446971T3 (es) 2009-05-12 2014-03-11 Albany Molecular Research, Inc. Tetrahidroisoquinolinas sustituidas con arilo, heteroarilo, y heterociclo y su uso
CA2760837C (en) * 2009-05-12 2018-04-03 Albany Molecular Research, Inc. 7-([1,2,4]triazolo[1,5-.alpha.]pyridin-6-yl)-4-(3,4-dichlorophenyl)-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
WO2013089278A1 (en) 2011-12-14 2013-06-20 Taiho Pharmaceutical Co., Ltd. Recombinant prpk-tprkb and uses thereof
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
PT3643709T (pt) 2014-10-30 2021-12-20 Kangpu Biopharmaceuticals Ltd Derivado, intermediário, método de preparação, composição farmacêutica de isoindolina e utilização dos mesmos
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
CA2991529C (en) * 2015-07-08 2021-01-05 Gilrose Pharmaceuticals, Llc Pre-frontal cortex processing disorder, gait and limb impairment treatment
KR102838444B1 (ko) 2015-09-30 2025-07-24 더 유니버시티 코트 오브 더 유니버시티 오브 애버딘 탈리도마이드 유사체 및 사용 방법
JP7264642B2 (ja) * 2016-03-16 2023-04-25 エイチ リー モフィット キャンサー センター アンド リサーチ インスティテュート インコーポレイテッド エフェクターｔ細胞機能を増進するための、セレブロンを標的とする小分子
CN108101886A (zh) * 2016-11-24 2018-06-01 天津和美生物技术有限公司 哌啶-2,6-二酮衍生物及其在治疗溃疡性结肠炎中的用途
IL321733A (en) 2017-10-18 2025-08-01 Novartis Ag Compositions and methods for selective degradation of proteins
PE20210184A1 (es) 2018-07-11 2021-02-02 H Lee Moffitt Cancer Ct & Res Compuestos inmunomoduladores dimericos contra mecanismos basados en cereblon
US11324731B2 (en) 2018-09-13 2022-05-10 City Of Hope TXNIP-TRX complex inhibitors and methods of using the same
EP3880669A1 (en) 2018-11-13 2021-09-22 Biotheryx, Inc. Substituted isoindolinones
CN111601789A (zh) * 2018-12-20 2020-08-28 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
US20220251152A1 (en) 2019-04-24 2022-08-11 Novartis Ag Compositions and methods for selective protein degradation
WO2021041664A1 (en) * 2019-08-27 2021-03-04 The 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
US12441707B2 (en) 2019-12-30 2025-10-14 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
WO2021170021A1 (zh) * 2020-02-25 2021-09-02 上海科技大学 基于戊二酰亚胺骨架的化合物及其应用
KR20220055171A (ko) * 2020-10-26 2022-05-03 주식회사 아이비스바이오 포말리도마이드로부터 3,6'-디티오포말리도마이드를 선택적으로 합성하는 방법
WO2022187423A1 (en) * 2021-03-03 2022-09-09 The Regents Of The University Of Michigan Cereblon ligands
KR102898419B1 (ko) 2022-02-25 2025-12-11 주식회사 아이비스바이오 신규한 포말리도마이드 유도체, 이의 제조방법 및 용도
US20240208937A1 (en) 2022-11-04 2024-06-27 Bristol-Myers Squibb Company Compounds and Their Use for Treatment of Hemoglobinopathies
CN119654316A (zh) * 2023-07-14 2025-03-18 标新生物医药科技(上海)有限公司 基于硫代的戊二酰亚胺基异吲哚啉酮骨架的化合物及其应用

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
DK0580641T3 (da) 1991-04-17 1997-01-20 Gruenenthal Gmbh Hidtil ukendte thalidomidderivater, en fremgangsmåde til deres fremstilling samt deres anvendelse i lægemidler
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
US20010056114A1 (en) * 2000-11-01 2001-12-27 D'amato Robert Methods for the inhibition of angiogenesis with 3-amino thalidomide
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
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
WO1997045117A1 (en) 1996-05-29 1997-12-04 Prototek, Inc. Prodrugs of thalidomide and methods for using same as modulators of t-cell function
CZ302378B6 (cs) 1996-07-24 2011-04-20 Celgene Corporation Optický izomer (S)-1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindolin a farmaceutická kompozice s jeho obsahem
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
WO1999058096A2 (en) 1998-05-11 1999-11-18 Entremed, Inc. Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis
TR200003355T2 (tr) 1998-05-15 2001-03-21 Astrazeneca Ab Sitokinin sebep olduğu hastalıkların tedavisinde benzamid türevlerinin kullanılması
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
SI1040838T1 (en) * 1999-03-31 2003-08-31 Gruenenthal Gmbh Stable aqueous solution of 3-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione
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
CA2430669C (en) 2000-11-30 2011-06-14 The Children's Medical Center Corporation Synthesis of 3-amino-thalidomide and its enantiomers
US20030045552A1 (en) 2000-12-27 2003-03-06 Robarge Michael J. Isoindole-imide compounds, compositions, and uses thereof
US7320991B2 (en) 2001-02-27 2008-01-22 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services, National Institutes Of Health Analogs of thalidomide as potential angiogenesis inhibitors
CA2457319C (en) 2001-08-06 2011-07-05 The Children's Medical Center Corporation 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
SI1505973T1 (sl) 2002-05-17 2010-06-30 Celgene Corp Kombinacija za zdravljenje multiplega mieloma
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

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CA2538864A1 (en) 2005-03-31
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CA2808646A1 (en) 2005-03-31
US20060211728A1 (en) 2006-09-21
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WO2005028436A2 (en) 2005-03-31
AU2004274474A1 (en) 2005-03-31
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US8546430B2 (en) 2013-10-01
CN1867331A (zh) 2006-11-22
CN1867331B (zh) 2010-05-26
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US20110245210A1 (en) 2011-10-06
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