CA2707339C - (aza)indole derivative substituted in position 5, pharmaceutical composition comprising it, intermediate compounds and preparation process therefor - Google Patents
(aza)indole derivative substituted in position 5, pharmaceutical composition comprising it, intermediate compounds and preparation process therefor Download PDFInfo
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- CA2707339C CA2707339C CA2707339A CA2707339A CA2707339C CA 2707339 C CA2707339 C CA 2707339C CA 2707339 A CA2707339 A CA 2707339A CA 2707339 A CA2707339 A CA 2707339A CA 2707339 C CA2707339 C CA 2707339C
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- alkyl
- different
- alkenyl
- bond
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 37
- -1 nitro, amino Chemical group 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 28
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- 238000000034 method Methods 0.000 claims description 27
- 230000002829 reductive effect Effects 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 25
- 125000006193 alkinyl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- 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
- A61P35/00—Antineoplastic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
- C07D209/12—Radicals substituted by oxygen atoms
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07425830A EP2078711A1 (en) | 2007-12-28 | 2007-12-28 | (Aza)indole derivative substituted in position 5, pharmaceutical composition comprising it, intermediate compounds and preparation process therefor |
| EP07425830.2 | 2007-12-28 | ||
| PCT/EP2008/067622 WO2009083436A1 (en) | 2007-12-28 | 2008-12-16 | (aza)indole derivative substituted in position 5, pharmaceutical composition comprising it, intermediate compounds and preparation process therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2707339A1 CA2707339A1 (en) | 2009-07-09 |
| CA2707339C true CA2707339C (en) | 2018-05-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2707339A Expired - Fee Related CA2707339C (en) | 2007-12-28 | 2008-12-16 | (aza)indole derivative substituted in position 5, pharmaceutical composition comprising it, intermediate compounds and preparation process therefor |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US8399477B2 (enExample) |
| EP (3) | EP2078711A1 (enExample) |
| JP (1) | JP5698985B2 (enExample) |
| KR (2) | KR20160029861A (enExample) |
| CN (1) | CN101910127B (enExample) |
| AR (1) | AR069961A1 (enExample) |
| AU (1) | AU2008342705B2 (enExample) |
| BR (1) | BRPI0821450A2 (enExample) |
| CA (1) | CA2707339C (enExample) |
| DK (2) | DK2234968T3 (enExample) |
| EA (1) | EA020373B1 (enExample) |
| ES (2) | ES2408955T3 (enExample) |
| GE (1) | GEP20125547B (enExample) |
| IL (1) | IL206062A (enExample) |
| PL (2) | PL2234968T3 (enExample) |
| PT (2) | PT2444392E (enExample) |
| SG (1) | SG187400A1 (enExample) |
| SI (2) | SI2234968T1 (enExample) |
| UA (1) | UA100867C2 (enExample) |
| WO (1) | WO2009083436A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101365824B1 (ko) | 2010-10-22 | 2014-02-20 | 엘지디스플레이 주식회사 | 유기전계발광소자 |
| DK3102576T3 (da) | 2014-02-03 | 2019-07-22 | Vitae Pharmaceuticals Llc | Dihydropyrrolopyridininhibitorer af ror-gamma |
| KR20160134865A (ko) * | 2014-04-14 | 2016-11-23 | 샹하이 헨그루이 파마수티컬 컴퍼니 리미티드 | 아미드 유도체 및 이의 약제학적으로 허용되는 염, 이의 제조방법 및 이의 의학적 적용 |
| US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| EP3331876B1 (en) | 2015-08-05 | 2020-10-07 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
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| TWI757266B (zh) | 2016-01-29 | 2022-03-11 | 美商維它藥物有限責任公司 | ＲＯＲ－γ調節劑 |
| CN107033026A (zh) * | 2017-06-07 | 2017-08-11 | 李博强 | 一种对硝基苯肼盐酸盐的制备方法 |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| CN115716826A (zh) | 2017-07-24 | 2023-02-28 | 生命医药有限责任公司 | RORγ的抑制剂 |
| CN114302874B (zh) * | 2019-08-26 | 2025-02-25 | 国际药品株式会社 | 吲哚甲酰胺衍生物和包含吲哚甲酰胺衍生物的药物组合物 |
| CN114605303A (zh) * | 2022-03-14 | 2022-06-10 | 武汉工程大学 | 一种地拉韦啶及其中间体的合成方法 |
| CN119019389B (zh) * | 2024-06-05 | 2026-05-26 | 四川大学 | 7-氮杂吲哚类化合物及其合成方法和用途 |
| CN119101040B (zh) * | 2024-11-08 | 2025-03-21 | 杭州澳赛诺医药技术有限公司 | 一种通过去对称化合成芳基取代的手性四氢吡喃环的方法 |
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| FR2354766A1 (fr) * | 1976-06-17 | 1978-01-13 | Labaz | Derives n-aminoalkyles d'indole et procedes pour les preparer |
| WO1999040072A1 (de) * | 1998-02-03 | 1999-08-12 | Boehringer Ingelheim Pharma Kg | 5-gliedrige benzokondensierte heterocyclen als antithrombotika |
| US6114532A (en) * | 1998-02-03 | 2000-09-05 | Boehringer Ingelheim Pharma Kg | Bicyclic heterocycles, the preparation thereof, and their use as pharmaceuticals |
| DE19834751A1 (de) * | 1998-08-01 | 2000-02-03 | Boehringer Ingelheim Pharma | Disubstituierte bicyclische Heterocyclen, ihre Herstellung und ihre Verwendung als Arzneimittel |
| US20030225036A1 (en) * | 2000-03-20 | 2003-12-04 | Aleksandr Kolesnikov | Non-amidine containing protease inhibitors |
| US20020052373A1 (en) * | 2000-10-26 | 2002-05-02 | Zorn Stevin H. | Combination treatment for dementia or cognitive deficits associated with alzheimer's disease and parkinson's disease |
| IL140096A0 (en) * | 2000-12-05 | 2002-02-10 | Internat Specialty Products Is | Process for preparation of zafirlukast |
| DE10147672A1 (de) * | 2001-09-27 | 2003-04-10 | Bayer Ag | Substituierte 2,5-Diamidoindole und ihre Verwendung |
| JP2006511562A (ja) * | 2002-12-20 | 2006-04-06 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | 泌尿器系疾患の処置のための置換２，５−ジアミドインドール類の使用 |
| SE0300908D0 (sv) * | 2003-03-31 | 2003-03-31 | Astrazeneca Ab | Azaindole derivatives, preparations thereof, uses thereof and compositions containing them |
| EP1833829A2 (en) * | 2004-12-23 | 2007-09-19 | F. Hoffmann-Roche AG | Benzamide substituted imidazo- and pyrrolo-pyridines as protein kinase inhibitors |
| EP1933834A1 (en) * | 2005-10-12 | 2008-06-25 | Biolipox AB | Benzoxazoles useful in the treatment of inflammation |
| JP5420395B2 (ja) * | 2006-04-07 | 2014-02-19 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｐ結合カセット輸送体の調節剤 |
| JP2008006663A (ja) * | 2006-06-28 | 2008-01-17 | Pilot Ink Co Ltd | 出没式筆記具 |
| 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 |
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