JP2006512293A - ＩｇＥを調節し、細胞増殖を阻害するためのフェニル−インドール化合物 - Google Patents
ＩｇＥを調節し、細胞増殖を阻害するためのフェニル−インドール化合物 Download PDFInfo
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- JP2006512293A JP2006512293A JP2004536642A JP2004536642A JP2006512293A JP 2006512293 A JP2006512293 A JP 2006512293A JP 2004536642 A JP2004536642 A JP 2004536642A JP 2004536642 A JP2004536642 A JP 2004536642A JP 2006512293 A JP2006512293 A JP 2006512293A
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Classifications
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- 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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
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- 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
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- 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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
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- 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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
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- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US6911462B2 (en) * | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| JP2004528304A (ja) * | 2001-03-12 | 2004-09-16 | アバニール・ファーマシューティカルズ | ＩｇＥを調節し、細胞増殖を阻害するためのベンゾイミダゾール化合物 |
| TW200304820A (en) * | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| AU2003270426A1 (en) * | 2002-09-12 | 2004-04-30 | Avanir Pharmaceuticals | PHENYL-INDOLE COMPOUNDS FOR MODULATING IgE AND INHIBITING CELLULAR PROLIFERATION |
| TWI276631B (en) * | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| AU2004263190A1 (en) * | 2003-08-08 | 2005-02-17 | Avanir Pharmaceuticals | Selective pharmacologic inhibition of protein trafficking and related methods of treating human diseases |
| EA200700243A1 (ru) | 2004-07-14 | 2007-08-31 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения гепатита с |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| EP1781289A1 (en) | 2004-07-22 | 2007-05-09 | PTC Therapeutics, Inc. | Thienopyridines for treating hepatitis c |
| ITMI20061368A1 (it) * | 2006-07-14 | 2008-01-15 | Acraf | Composto 2-arilindolico sostituito in posizione 5, composizione farmaceutica che lo comprende nonche' composti intermedi e procedimento per prepararlo |
| KR20150070290A (ko) * | 2012-10-17 | 2015-06-24 | 에프. 호프만-라 로슈 아게 | Trp 채널 길항제로서의 6-아미노인돌 유도체 |
| TWI752155B (zh) | 2017-02-01 | 2022-01-11 | 德商菲尼克斯製藥股份有限公司 | 芳香烴受體(AhR)調節劑化合物 |
| TWI674260B (zh) | 2017-02-01 | 2019-10-11 | 德商菲尼克斯製藥股份有限公司 | 芳基烴受體(AhR)調節劑化合物 |
| TW201835070A (zh) * | 2017-02-21 | 2018-10-01 | 德商菲尼克斯製藥股份有限公司 | 芳香烴受體(AhR)調節劑化合物 |
| EP3723790B1 (en) * | 2017-12-12 | 2024-03-13 | Kamada Ltd | Methods of inducing immune tolerance and reducing anti-drug antibody response |
| WO2020078453A1 (en) * | 2018-10-18 | 2020-04-23 | Sinomab Bioscience Limited | Methods of treating rheumatoid arthritis |
| IL297986A (en) | 2020-05-08 | 2023-01-01 | Genmab As | Bispecific antibodies against cd3 and cd20 |
| US20240034788A1 (en) * | 2020-08-20 | 2024-02-01 | The Board Of Trustees Of The Leland Stanford Junior University | Abscopal therapy for cancer |
| MX2023002545A (es) | 2020-09-10 | 2023-03-14 | Genmab As | Anticuerpo biespecifico contra cumulo de diferenciacion 3 (cd3) y cumulo de diferenciacion 20 (cd20) en terapia de combinacion para el tratamiento de linfoma difuso de celulas b grandes. |
| CA3192255A1 (en) | 2020-09-10 | 2022-03-17 | Brian Elliott | Bispecific antibody against cd3 and cd20 in combination therapy for treating diffuse large b-cell lymphoma |
| CN116507363A (zh) | 2020-09-10 | 2023-07-28 | 健玛保 | 用于治疗滤泡性淋巴瘤的联合疗法中的针对cd3和cd20的双特异性抗体 |
| CN116437956A (zh) | 2020-09-10 | 2023-07-14 | 健玛保 | 用于治疗慢性淋巴细胞白血病的针对cd3和cd20的双特异性抗体 |
| CN116406293A (zh) | 2020-09-10 | 2023-07-07 | 健玛保 | 用于治疗滤泡性淋巴瘤的联合疗法中的针对cd3和cd20的双特异性抗体 |
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| DE3224512A1 (de) | 1982-07-01 | 1984-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| US4510158A (en) | 1984-03-05 | 1985-04-09 | Sterling Drug Inc. | 2-Phenylindole derivatives, their use as complement inhibitors |
| WO1986006739A1 (en) | 1985-05-03 | 1986-11-20 | The Foxboro Company | Distillation cut point control |
| US4939133A (en) | 1985-10-01 | 1990-07-03 | Warner-Lambert Company | N-substituted-2-hydroxy-α-oxo-benzeneacetamides and pharmaceutical compositions having activity as modulators of the arachidonic acid cascade |
| LU86258A1 (fr) | 1986-01-21 | 1987-09-03 | Rech Dermatologiques C I R D S | Composes benzamido aromatique,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| US5206257A (en) | 1987-03-05 | 1993-04-27 | May & Baker Limited | Pesticidal method using 2-phenylimidazole derivatives |
| JP2630432B2 (ja) | 1987-08-24 | 1997-07-16 | コニカ株式会社 | 新規なシアンカプラーを含有するハロゲン化銀カラー写真感光材料 |
| ES2058490T3 (es) | 1988-02-02 | 1994-11-01 | Schering Biotech Corp | Metodo de reducir respuestas de inmunoglobulina e. |
| JP2700475B2 (ja) | 1988-07-30 | 1998-01-21 | コニカ株式会社 | 非線形光学材料および非線形光学素子 |
| IT1232252B (it) | 1989-02-22 | 1992-01-28 | Rotta Research Lab | Derivati della n fenil benzamide ad attivita' antiulcera ed antiallerica e procedimento per la loro preparazione |
| FR2643903A1 (fr) | 1989-03-03 | 1990-09-07 | Union Pharma Scient Appl | Nouveaux derives de benzimidazole, leurs procedes de preparation, intermediaires de synthese, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et des ulceres duodenaux |
| EP0415886A3 (en) | 1989-08-30 | 1991-10-23 | Ciba-Geigy Ag | Aza compounds |
| FR2658511B1 (fr) | 1990-02-16 | 1992-06-19 | Union Pharma Scient Appl | Nouveaux derives de benzimidazole et d'azabenzimidazole, antagonistes des recepteurs au thromboxane; leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| AU8225991A (en) | 1990-07-31 | 1992-03-02 | Teikoku Hormone Mfg. Co., Ltd. | 2-phenylindole derivative |
| DK0469477T3 (da) | 1990-08-02 | 1995-12-27 | Hoffmann La Roche | Antiallergisk kombination |
| US5656762A (en) | 1990-12-28 | 1997-08-12 | Neurogen Corporation | 4-piperidino-and piperazinomethyl-2-phenylimidazole derivatives, dopamine receptor subtype specific ligands |
| JPH06263993A (ja) | 1991-01-21 | 1994-09-20 | Konica Corp | アゾメチン系染料、インドアニリン系染料及びインドフェノール系染料の製造法 |
| IE71647B1 (en) | 1991-01-28 | 1997-02-26 | Rhone Poulenc Rorer Ltd | Benzamide derivatives |
| EP0607373B1 (en) | 1992-06-15 | 1997-03-19 | Celltech Therapeutics Limited | Trisubstituted phenyl derivatives as selective phosphodiesterase iv inhibitors |
| US5322847A (en) | 1992-11-05 | 1994-06-21 | Pfizer Inc. | Azabenzimidazoles in the treatment of asthma, arthritis and related diseases |
| IL113472A0 (en) | 1994-04-29 | 1995-07-31 | Lilly Co Eli | Non-peptidyl tachykinin receptor antogonists |
| US5643893A (en) | 1994-06-22 | 1997-07-01 | Macronex, Inc. | N-substituted-(Dihydroxyboryl)alkyl purine, indole and pyrimidine derivatives, useful as inhibitors of inflammatory cytokines |
| DE4426625A1 (de) | 1994-07-27 | 1996-03-14 | Schering Ag | 2-Phenylindole, Verfahren zu deren Herstellung, diese enthaltende pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
| US5496826A (en) | 1994-09-02 | 1996-03-05 | Bristol-Myers Squibb Company | Pharmaceutical methods of using heterocyclic derivatives of N-phenylamides |
| US5821258A (en) | 1994-12-27 | 1998-10-13 | Mitsui Chemicals, Inc. | Phenylbenzimidazole derivatives |
| DE19503160A1 (de) | 1995-02-01 | 1996-08-08 | Bayer Ag | Verwendung von Phenylcyclohexylcarbonsäureamiden |
| IL123147A (en) | 1995-08-02 | 2004-02-19 | Univ Newcastle Ventures Ltd | Benzamide imidazole - 4 carboxamide and their use |
| US6387938B1 (en) | 1996-07-05 | 2002-05-14 | Mochida Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| TW467902B (en) | 1996-07-31 | 2001-12-11 | Bristol Myers Squibb Co | Diphenyl heterocycles as potassium channel modulators |
| US6153631A (en) | 1996-10-23 | 2000-11-28 | Zymogenetics, Inc. | Compositions and methods for treating bone deficit conditions |
| JP2001510450A (ja) | 1996-10-23 | 2001-07-31 | ザイモジェネティクス，インコーポレイテッド | 骨欠損状態を処置するための組成物および方法 |
| CA2232467A1 (en) | 1997-03-20 | 1998-09-20 | Richard A. Glennon | Imidazoles with serotonin receptor binding activity |
| US6034256A (en) | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
| CN1265665A (zh) | 1997-06-10 | 2000-09-06 | 葛兰素集团有限公司 | 苯并咪唑衍生物 |
| GB9718833D0 (en) * | 1997-09-04 | 1997-11-12 | Merck Sharp & Dohme | Therapeutic agents |
| ATE281834T1 (de) | 1997-09-26 | 2004-11-15 | Zentaris Gmbh | Azabenzimidazol-verbindungen zur modulation der serin/threonin protein-kinase funktion |
| US6100282A (en) | 1998-01-02 | 2000-08-08 | Hoffman-La Roche Inc. | Thiazole derivatives |
| US6303645B1 (en) | 1998-05-22 | 2001-10-16 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| US6911462B2 (en) | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| US6271390B1 (en) | 1998-05-22 | 2001-08-07 | Avanir Pharmaceuticals | Suppression of the IgE-dependent allergic response by benzimidazole analogs |
| US6919366B2 (en) | 1998-05-22 | 2005-07-19 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| US6369091B1 (en) | 1998-05-22 | 2002-04-09 | Avanir Pharmaceuticals | Benzimidazole analogs as down-regulators of IgE |
| JP2000095767A (ja) | 1998-09-28 | 2000-04-04 | Takeda Chem Ind Ltd | 性腺刺激ホルモン放出ホルモン拮抗剤 |
| NZ510760A (en) | 1998-10-23 | 2003-08-29 | F | Bicyclic nitrogen heterocycles |
| CN1331682A (zh) | 1998-11-03 | 2002-01-16 | 巴斯福股份公司 | 取代的2－苯基苯并咪唑类,其制备和用途 |
| HRP20010451A2 (en) | 1998-11-17 | 2003-04-30 | Basf Ag | 2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof |
| IL143303A0 (en) | 1998-11-27 | 2002-04-21 | Basf Ag | Substituted benzimidazoles and their use as parp inhibitors |
| DE19918211A1 (de) | 1999-04-22 | 2000-10-26 | Basf Ag | Cycloalkylsubstituierte Benzimidazole, deren Herstellung und Anwendung |
| DE19920936A1 (de) | 1999-05-07 | 2000-11-09 | Basf Ag | Heterozyklisch substituierte Benzimidazole, deren Herstellung und Anwendung |
| US6423734B1 (en) | 1999-08-13 | 2002-07-23 | The Procter & Gamble Company | Method of preventing cancer |
| DE19939463A1 (de) | 1999-08-20 | 2001-02-22 | Boehringer Ingelheim Pharma | Aminocarbonyl-substituierte Benzimidazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US6759425B2 (en) | 1999-10-21 | 2004-07-06 | Avanir Pharmaceuticals | Benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| US6242461B1 (en) | 2000-01-25 | 2001-06-05 | Pfizer Inc. | Use of aryl substituted azabenzimidazoles in the treatment of HIV and AIDS related diseases |
| GB0007405D0 (en) | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| US6537994B2 (en) | 2000-07-17 | 2003-03-25 | Wyeth | Heterocyclic β3 adrenergic receptor agonists |
| JP2004528304A (ja) | 2001-03-12 | 2004-09-16 | アバニール・ファーマシューティカルズ | ＩｇＥを調節し、細胞増殖を阻害するためのベンゾイミダゾール化合物 |
| MXPA03008205A (es) | 2001-03-12 | 2004-01-29 | Janssen Pharmaceutica Nv | Procedimiento para la preparacion de compuestos de imidazol. |
| US6777442B2 (en) | 2001-03-12 | 2004-08-17 | Bayer Aktiengesellschaft | Diphenyl derivatives |
| TW200304820A (en) | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| TWI276631B (en) | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| AU2003270426A1 (en) * | 2002-09-12 | 2004-04-30 | Avanir Pharmaceuticals | PHENYL-INDOLE COMPOUNDS FOR MODULATING IgE AND INHIBITING CELLULAR PROLIFERATION |
| RU2005134670A (ru) | 2003-04-10 | 2006-06-10 | Аванир Фармасьютикалс (Us) | Производные имидазола для лечения аллергических и гиперпролиферативных нарушений |
| AU2004263190A1 (en) | 2003-08-08 | 2005-02-17 | Avanir Pharmaceuticals | Selective pharmacologic inhibition of protein trafficking and related methods of treating human diseases |
-
2003
- 2003-09-09 AU AU2003270426A patent/AU2003270426A1/en not_active Withdrawn
- 2003-09-09 WO PCT/US2003/028145 patent/WO2004024655A2/en not_active Ceased
- 2003-09-10 TW TW092124977A patent/TW200407303A/zh unknown
- 2003-09-12 PE PE2003000932A patent/PE20050035A1/es not_active Application Discontinuation
- 2003-09-12 RU RU2005109912/04A patent/RU2005109912A/ru not_active Application Discontinuation
- 2003-09-12 WO PCT/US2003/030959 patent/WO2004024896A2/en not_active Ceased
- 2003-09-12 KR KR1020057004244A patent/KR20050051658A/ko not_active Withdrawn
- 2003-09-12 MX MXJL05000009A patent/MXJL05000009A/es not_active Application Discontinuation
- 2003-09-12 AR ARP030103320A patent/AR041251A1/es not_active Application Discontinuation
- 2003-09-12 AU AU2003277152A patent/AU2003277152A1/en not_active Abandoned
- 2003-09-12 EP EP03795717A patent/EP1537079A4/en not_active Withdrawn
- 2003-09-12 JP JP2004536642A patent/JP2006512293A/ja not_active Withdrawn
- 2003-09-12 US US10/661,139 patent/US7375118B2/en not_active Expired - Fee Related
- 2003-09-12 BR BR0314223-0A patent/BR0314223A/pt not_active IP Right Cessation
- 2003-09-12 CA CA002498493A patent/CA2498493A1/en not_active Abandoned
- 2003-09-12 PL PL03375812A patent/PL375812A1/xx not_active Application Discontinuation
- 2003-09-12 CN CNA038250829A patent/CN1694868A/zh active Pending
-
2005
- 2005-04-05 ZA ZA200502739A patent/ZA200502739B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003277152A1 (en) | 2004-04-30 |
| CA2498493A1 (en) | 2004-03-25 |
| CN1694868A (zh) | 2005-11-09 |
| WO2004024655A2 (en) | 2004-03-25 |
| PE20050035A1 (es) | 2005-01-24 |
| RU2005109912A (ru) | 2006-04-27 |
| EP1537079A4 (en) | 2007-05-16 |
| WO2004024896A2 (en) | 2004-03-25 |
| BR0314223A (pt) | 2005-07-26 |
| US7375118B2 (en) | 2008-05-20 |
| AR041251A1 (es) | 2005-05-11 |
| MXJL05000009A (es) | 2005-06-07 |
| PL375812A1 (en) | 2005-12-12 |
| KR20050051658A (ko) | 2005-06-01 |
| ZA200502739B (en) | 2005-10-13 |
| WO2004024896A3 (en) | 2004-06-24 |
| EP1537079A2 (en) | 2005-06-08 |
| TW200407303A (en) | 2004-05-16 |
| US20040180946A1 (en) | 2004-09-16 |
| AU2003270426A1 (en) | 2004-04-30 |
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