CA2356898A1 - Indole derivatives and their use as mcp-1 antagonists - Google Patents
Indole derivatives and their use as mcp-1 antagonists Download PDFInfo
- Publication number
- CA2356898A1 CA2356898A1 CA002356898A CA2356898A CA2356898A1 CA 2356898 A1 CA2356898 A1 CA 2356898A1 CA 002356898 A CA002356898 A CA 002356898A CA 2356898 A CA2356898 A CA 2356898A CA 2356898 A1 CA2356898 A1 CA 2356898A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- ethyl
- chlorophenyl
- chloro
- 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.)
- Abandoned
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 150000002475 indoles Chemical class 0.000 title description 2
- 229940123313 MCP-1 antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- -1 carboxy, tetrazolyl Chemical group 0.000 claims abstract description 83
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000000651 prodrug Substances 0.000 claims abstract description 22
- 229940002612 prodrug Drugs 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 230000001404 mediated effect Effects 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims abstract description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 6
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 5
- 210000001744 T-lymphocyte Anatomy 0.000 claims abstract description 4
- 230000004913 activation Effects 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 230000001105 regulatory effect Effects 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 4
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- 238000000034 method Methods 0.000 claims description 45
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- 125000006239 protecting group Chemical group 0.000 claims description 9
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 35
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- JUJBNYBVVQSIOU-UHFFFAOYSA-M sodium;4-[2-(4-iodophenyl)-3-(4-nitrophenyl)tetrazol-2-ium-5-yl]benzene-1,3-disulfonate Chemical compound [Na+].C1=CC([N+](=O)[O-])=CC=C1N1[N+](C=2C=CC(I)=CC=2)=NC(C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)=N1 JUJBNYBVVQSIOU-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—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)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9902461.4 | 1999-02-05 | ||
| GBGB9902461.4A GB9902461D0 (en) | 1999-02-05 | 1999-02-05 | Chemical compounds |
| PCT/GB2000/000265 WO2000046196A1 (en) | 1999-02-05 | 2000-01-31 | Indole derivatives and their use as mcp-1 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2356898A1 true CA2356898A1 (en) | 2000-08-10 |
Family
ID=10847084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002356898A Abandoned CA2356898A1 (en) | 1999-02-05 | 2000-01-31 | Indole derivatives and their use as mcp-1 antagonists |
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| EP (1) | EP1150952B1 (enExample) |
| JP (1) | JP2002536359A (enExample) |
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| AT (1) | ATE280757T1 (enExample) |
| AU (1) | AU770856B2 (enExample) |
| BR (1) | BR0007984A (enExample) |
| CA (1) | CA2356898A1 (enExample) |
| CZ (1) | CZ20012807A3 (enExample) |
| DE (1) | DE60015296T2 (enExample) |
| EE (1) | EE200100403A (enExample) |
| GB (1) | GB9902461D0 (enExample) |
| HU (1) | HUP0105079A3 (enExample) |
| ID (1) | ID30401A (enExample) |
| IL (1) | IL144611A0 (enExample) |
| IS (1) | IS5980A (enExample) |
| MY (1) | MY133209A (enExample) |
| NO (1) | NO20013809L (enExample) |
| NZ (1) | NZ512680A (enExample) |
| PL (1) | PL350184A1 (enExample) |
| RU (1) | RU2235090C2 (enExample) |
| SK (1) | SK11152001A3 (enExample) |
| TR (1) | TR200102233T2 (enExample) |
| WO (1) | WO2000046196A1 (enExample) |
| ZA (1) | ZA200105311B (enExample) |
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| GB9716657D0 (en) | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| GB9902461D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB0000625D0 (en) * | 2000-01-13 | 2000-03-01 | Zeneca Ltd | Chemical compounds |
| GB0000626D0 (en) * | 2000-01-13 | 2000-03-01 | Zeneca Ltd | Chemical compounds |
| AU2002211901A1 (en) | 2000-10-10 | 2002-04-22 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compositions containing such indoles and their use as PPAR-gamma binding agents |
| AR035773A1 (es) | 2000-12-20 | 2004-07-14 | Bristol Myers Squibb Pharma Co | Compuestos diamino ciclico, composicion farmaceutica y su uso en la fabricacion de un medicamento util para modular la actividad de una quimioquina |
| JP2005506949A (ja) | 2000-12-20 | 2005-03-10 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | ケモカイン受容体の調節剤としてのジアミン |
| US7842693B2 (en) | 2002-06-12 | 2010-11-30 | Chemocentryx, Inc. | Substituted piperazines |
| JP4723242B2 (ja) | 2002-06-12 | 2011-07-13 | ケモセントリックス インコーポレーティッド | 炎症および免疫障害治療用ｃｃｒ１アンタゴニストとして使用するための１−アリール−４−置換ピペラジン誘導体 |
| US7589199B2 (en) | 2002-06-12 | 2009-09-15 | Chemocentryx, Inc. | Substituted piperazines |
| TW200508224A (en) | 2003-02-12 | 2005-03-01 | Bristol Myers Squibb Co | Cyclic derivatives as modulators of chemokine receptor activity |
| TW201018661A (en) | 2003-03-14 | 2010-05-16 | Ono Pharmaceutical Co | Heterocyclic rinf having nitrogen atom derivatives and medicament containing the derivatives as active ingredient |
| EP2364982A1 (en) | 2003-04-18 | 2011-09-14 | ONO Pharmaceutical Co., Ltd. | Spiro-piperidine compounds as chemokine receptor antagonists and medicinal use thereof |
| US7230133B2 (en) | 2003-05-01 | 2007-06-12 | Bristol-Myers Squibb Company | Malonamides and malonamide derivatives as modulators of chemokine receptor activity |
| US7291615B2 (en) | 2003-05-01 | 2007-11-06 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| US7381738B2 (en) | 2004-02-19 | 2008-06-03 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7479496B2 (en) | 2004-02-19 | 2009-01-20 | Bristol-Myers Squibb Company | Substituted spiro azabicyclics as modulators of chemokine receptor activity |
| US7230022B2 (en) | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
| US7288563B2 (en) | 2004-02-19 | 2007-10-30 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7435831B2 (en) | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
| JP4845873B2 (ja) | 2004-03-03 | 2011-12-28 | ケモセントリックス インコーポレーティッド | 二環式および架橋した窒素複素環 |
| US8481035B2 (en) | 2004-04-27 | 2013-07-09 | Northwestern University | Methods for treating chronic pelvic pain syndrome with antibodies that binds MCP-1 or MIP-1A |
| JP2008512463A (ja) * | 2004-09-08 | 2008-04-24 | ボーイズ タウン ナショナル リサーチ ホスピタル | マトリックスメタロプロテイナーゼ−１２に関連する糸球体基底膜疾患の治療 |
| AU2005283326B2 (en) | 2004-09-13 | 2011-07-21 | Ono Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient |
| WO2006129679A1 (ja) | 2005-05-31 | 2006-12-07 | Ono Pharmaceutical Co., Ltd. | スピロピペリジン化合物およびその医薬用途 |
| FR2890071B1 (fr) | 2005-08-30 | 2007-11-09 | Fournier Sa Sa Lab | Nouveaux composes de l'indole |
| US8318931B2 (en) | 2005-10-28 | 2012-11-27 | Ono Pharmaceutical Co., Ltd. | Chemokine receptor antagonists and use thereof |
| EP1961744B1 (en) | 2005-11-18 | 2013-04-17 | Ono Pharmaceutical Co., Ltd. | Basic group-containing compound and use thereof |
| AU2006324089A1 (en) | 2005-12-09 | 2007-06-14 | F. Hoffmann-La Roche Ag | Tricyclic amide derivatives useful for treating obesity |
| CA2644809A1 (en) * | 2006-03-02 | 2007-09-07 | Astellas Pharma Inc. | 17 .beta. hsd type 5 inhibitor |
| JPWO2007105637A1 (ja) | 2006-03-10 | 2009-07-30 | 小野薬品工業株式会社 | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
| WO2007132846A1 (ja) | 2006-05-16 | 2007-11-22 | Ono Pharmaceutical Co., Ltd. | 保護されていてもよい酸性基を含有する化合物およびその用途 |
| DE102006033572A1 (de) | 2006-07-20 | 2008-01-24 | Bayer Cropscience Ag | N'-Cyano-N-halogenalkyl-imidamid Derivate |
| US20090325992A1 (en) | 2006-07-31 | 2009-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having cyclic group bound thereto through spiro binding and use thereof |
| US20080076120A1 (en) * | 2006-09-14 | 2008-03-27 | Millennium Pharmaceuticals, Inc. | Methods for the identification, evaluation and treatment of patients having CC-Chemokine receptor 2 (CCR-2) mediated disorders |
| JP5379692B2 (ja) | 2006-11-09 | 2013-12-25 | プロビオドルグ エージー | 潰瘍、癌及び他の疾患の治療のためのグルタミニルシクラーゼの阻害薬としての３−ヒドロキシ−１，５−ジヒドロ−ピロール−２−オン誘導体 |
| WO2008065141A1 (en) | 2006-11-30 | 2008-06-05 | Probiodrug Ag | Novel inhibitors of glutaminyl cyclase |
| ZA200905537B (en) | 2007-03-01 | 2010-10-27 | Probiodrug Ag | New use of glutaminyl cyclase inhibitors |
| US9656991B2 (en) | 2007-04-18 | 2017-05-23 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| RU2503672C2 (ru) * | 2008-01-18 | 2014-01-10 | Оксаген Лимитед | Соединения, обладающие активностью антагонистов crth2 |
| AU2009304293B2 (en) * | 2008-10-16 | 2012-04-26 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| WO2010129351A1 (en) | 2009-04-28 | 2010-11-11 | Schepens Eye Research Institute | Method to identify and treat age-related macular degeneration |
| EP2475428B1 (en) | 2009-09-11 | 2015-07-01 | Probiodrug AG | Heterocylcic derivatives as inhibitors of glutaminyl cyclase |
| FR2950053B1 (fr) | 2009-09-11 | 2014-08-01 | Fournier Lab Sa | Utilisation de derives d'indole benzoique comme activateurs de nurr-1, pour le traitement de la maladie de parkinson |
| JP6026284B2 (ja) | 2010-03-03 | 2016-11-16 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤 |
| NZ602312A (en) | 2010-03-10 | 2014-02-28 | Probiodrug Ag | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
| WO2011131748A2 (en) | 2010-04-21 | 2011-10-27 | Probiodrug Ag | Novel inhibitors |
| KR101350077B1 (ko) * | 2010-12-13 | 2014-01-14 | 한국화학연구원 | 신규한 3-인돌리논 유도체 및 이를 포함하는 조성물 |
| JP6050264B2 (ja) | 2011-03-16 | 2016-12-21 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体 |
| CN110087530A (zh) | 2016-12-07 | 2019-08-02 | 普罗根尼蒂公司 | 胃肠道检测方法、装置和系统 |
| WO2018112264A1 (en) | 2016-12-14 | 2018-06-21 | Progenity Inc. | Treatment of a disease of the gastrointestinal tract with a chemokine/chemokine receptor inhibitor |
| DK3461819T3 (da) | 2017-09-29 | 2020-08-10 | Probiodrug Ag | Inhibitorer af glutaminylcyklase |
| CN116726362A (zh) | 2018-11-19 | 2023-09-12 | 比奥拉治疗股份有限公司 | 用生物治疗剂治疗疾病的方法和装置 |
| CN115666704B (zh) | 2019-12-13 | 2025-09-26 | 比特比德科有限责任公司 | 用于将治疗剂递送至胃肠道的可摄取装置 |
| EP4450494A1 (en) | 2023-04-20 | 2024-10-23 | Consejo Superior De Investigaciones Científicas | Indole derivatives as histone deacetylase (hdac) inhibitors for the treatment of cancer |
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-
1999
- 1999-02-05 GB GBGB9902461.4A patent/GB9902461D0/en not_active Ceased
-
2000
- 2000-01-31 EE EEP200100403A patent/EE200100403A/xx unknown
- 2000-01-31 IL IL14461100A patent/IL144611A0/xx unknown
- 2000-01-31 AT AT00901259T patent/ATE280757T1/de not_active IP Right Cessation
- 2000-01-31 BR BR0007984-7A patent/BR0007984A/pt not_active IP Right Cessation
- 2000-01-31 ID IDW00200101667A patent/ID30401A/id unknown
- 2000-01-31 KR KR1020017009862A patent/KR20010094755A/ko not_active Withdrawn
- 2000-01-31 HU HU0105079A patent/HUP0105079A3/hu unknown
- 2000-01-31 AU AU21213/00A patent/AU770856B2/en not_active Ceased
- 2000-01-31 TR TR2001/02233T patent/TR200102233T2/xx unknown
- 2000-01-31 RU RU2001124567/04A patent/RU2235090C2/ru not_active IP Right Cessation
- 2000-01-31 CZ CZ20012807A patent/CZ20012807A3/cs unknown
- 2000-01-31 PL PL00350184A patent/PL350184A1/xx not_active Application Discontinuation
- 2000-01-31 CN CN00803463A patent/CN1339025A/zh active Pending
- 2000-01-31 JP JP2000597267A patent/JP2002536359A/ja active Pending
- 2000-01-31 EP EP20000901259 patent/EP1150952B1/en not_active Expired - Lifetime
- 2000-01-31 SK SK1115-2001A patent/SK11152001A3/sk unknown
- 2000-01-31 DE DE60015296T patent/DE60015296T2/de not_active Expired - Lifetime
- 2000-01-31 AR ARP000100407A patent/AR022461A1/es not_active Application Discontinuation
- 2000-01-31 WO PCT/GB2000/000265 patent/WO2000046196A1/en not_active Ceased
- 2000-01-31 US US09/889,599 patent/US6737435B1/en not_active Expired - Fee Related
- 2000-01-31 CA CA002356898A patent/CA2356898A1/en not_active Abandoned
- 2000-01-31 NZ NZ512680A patent/NZ512680A/en unknown
- 2000-02-04 MY MYPI20000404A patent/MY133209A/en unknown
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2001
- 2001-06-26 IS IS5980A patent/IS5980A/is unknown
- 2001-06-27 ZA ZA200105311A patent/ZA200105311B/en unknown
- 2001-08-03 NO NO20013809A patent/NO20013809L/no not_active Application Discontinuation
Also Published As
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| DE60015296T2 (de) | 2006-02-02 |
| SK11152001A3 (sk) | 2001-12-03 |
| HUP0105079A2 (hu) | 2002-04-29 |
| EE200100403A (et) | 2002-10-15 |
| AU2121300A (en) | 2000-08-25 |
| AU770856B2 (en) | 2004-03-04 |
| KR20010094755A (ko) | 2001-11-01 |
| AR022461A1 (es) | 2002-09-04 |
| DE60015296D1 (de) | 2004-12-02 |
| IL144611A0 (en) | 2002-05-23 |
| CZ20012807A3 (cs) | 2001-10-17 |
| TR200102233T2 (tr) | 2001-12-21 |
| IS5980A (is) | 2001-06-26 |
| NZ512680A (en) | 2003-11-28 |
| EP1150952A1 (en) | 2001-11-07 |
| CN1339025A (zh) | 2002-03-06 |
| ATE280757T1 (de) | 2004-11-15 |
| BR0007984A (pt) | 2001-11-06 |
| NO20013809L (no) | 2001-10-02 |
| US6737435B1 (en) | 2004-05-18 |
| HUP0105079A3 (en) | 2002-11-28 |
| NO20013809D0 (no) | 2001-08-03 |
| MY133209A (en) | 2007-10-31 |
| JP2002536359A (ja) | 2002-10-29 |
| PL350184A1 (en) | 2002-11-18 |
| ZA200105311B (en) | 2002-09-27 |
| WO2000046196A1 (en) | 2000-08-10 |
| EP1150952B1 (en) | 2004-10-27 |
| RU2001124567A (ru) | 2004-01-10 |
| GB9902461D0 (en) | 1999-03-24 |
| ID30401A (id) | 2001-11-29 |
| RU2235090C2 (ru) | 2004-08-27 |
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| FZDE | Discontinued |