JP2012519202A5 - - Google Patents
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- JP2012519202A5 JP2012519202A5 JP2011552413A JP2011552413A JP2012519202A5 JP 2012519202 A5 JP2012519202 A5 JP 2012519202A5 JP 2011552413 A JP2011552413 A JP 2011552413A JP 2011552413 A JP2011552413 A JP 2011552413A JP 2012519202 A5 JP2012519202 A5 JP 2012519202A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- following formula
- group
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- -1 ropirinol Chemical compound 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000000508 neurotrophic effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims 1
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 claims 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 claims 1
- KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- 229910010082 LiAlH Inorganic materials 0.000 claims 1
- 102000016397 Methyltransferase Human genes 0.000 claims 1
- 108060004795 Methyltransferase Proteins 0.000 claims 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 claims 1
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims 1
- HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
- 229960003805 amantadine Drugs 0.000 claims 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 1
- 229960000794 baclofen Drugs 0.000 claims 1
- 229960004596 cabergoline Drugs 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- 150000003943 catecholamines Chemical class 0.000 claims 1
- 239000000064 cholinergic agonist Substances 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims 1
- 229940052760 dopamine agonists Drugs 0.000 claims 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 claims 1
- 229960003337 entacapone Drugs 0.000 claims 1
- 229960003980 galantamine Drugs 0.000 claims 1
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims 1
- 230000000848 glutamatergic effect Effects 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims 1
- 229960004640 memantine Drugs 0.000 claims 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 239000004090 neuroprotective agent Substances 0.000 claims 1
- 230000000324 neuroprotective effect Effects 0.000 claims 1
- 229960004851 pergolide Drugs 0.000 claims 1
- YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 claims 1
- 229960003089 pramipexole Drugs 0.000 claims 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 229960004136 rivastigmine Drugs 0.000 claims 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 claims 1
- 229960003946 selegiline Drugs 0.000 claims 1
- 229960001685 tacrine Drugs 0.000 claims 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims 1
- 229960001032 trihexyphenidyl Drugs 0.000 claims 1
- 0 **NCCc1c[n]c2c1C=C*C=C2 Chemical compound **NCCc1c[n]c2c1C=C*C=C2 0.000 description 5
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0951303 | 2009-03-02 | ||
| FR0951303A FR2942625B1 (fr) | 2009-03-02 | 2009-03-02 | Derives indoliques pour le traitement de maladies neurodegeneratives |
| PCT/EP2010/052596 WO2010100133A2 (fr) | 2009-03-02 | 2010-03-02 | Derives indoliques pour le traitement de maladies neurodegeneratives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012519202A JP2012519202A (ja) | 2012-08-23 |
| JP2012519202A5 true JP2012519202A5 (https=) | 2013-04-18 |
Family
ID=40688413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011552413A Pending JP2012519202A (ja) | 2009-03-02 | 2010-03-02 | 神経変性疾患を治療するためのインドール誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8614246B2 (https=) |
| EP (1) | EP2403830A2 (https=) |
| JP (1) | JP2012519202A (https=) |
| CN (1) | CN102369185A (https=) |
| CA (1) | CA2754283A1 (https=) |
| FR (1) | FR2942625B1 (https=) |
| WO (1) | WO2010100133A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9744155B2 (en) | 2012-03-28 | 2017-08-29 | Ixcela, Inc. | IPA as a therapeutic agent, as a protective agent, and as a biomarker of disease risk |
| CN106309436A (zh) * | 2016-07-25 | 2017-01-11 | 宁波大学 | 可用作乙酰胆碱酯酶抑制剂的色胺衍生物及其用途 |
| CN106565588A (zh) * | 2016-11-10 | 2017-04-19 | 徐州工程学院 | 一种从坚果中提取食物源二十烷酸‑5‑羟色胺的方法 |
| KR101874594B1 (ko) * | 2016-12-07 | 2018-07-05 | 한국한의학연구원 | 아떼모야 잎 추출물 또는 이의 분획물을 포함하는 인지기능 장애의 예방 또는 치료용 조성물 |
| CN107118146B (zh) * | 2017-04-13 | 2019-09-03 | 宁波大学 | 一种6-溴色胺衍生物及其制备方法和用途 |
| CN107814787A (zh) * | 2017-11-13 | 2018-03-20 | 济南大学 | 一种他克林‑吲哚乙酸杂联体化合物及其制备方法和应用 |
| US11041847B1 (en) | 2019-01-25 | 2021-06-22 | Ixcela, Inc. | Detection and modification of gut microbial population |
| IL297869A (en) * | 2020-05-04 | 2023-01-01 | Tufts College | Synthetic lipid-like agents for administration in the brain |
| CA3229361A1 (en) * | 2021-08-20 | 2023-02-23 | Abdelmalik Slassi | 3-cycloamino-indole compounds as serotonergic agents useful for the treatment of disorders related thereto |
| WO2025137730A1 (en) * | 2023-12-22 | 2025-06-26 | Alexander Shulgin Research Institute, Inc. | N-substituted tryptamines and n-substituted lysergamides and their use as therapeutic agents |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08239362A (ja) * | 1994-12-28 | 1996-09-17 | Sankyo Co Ltd | インドール誘導体 |
| FR2729147A1 (fr) * | 1995-01-11 | 1996-07-12 | Adir | Nouveaux composes (hetero) cycliques alkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JPH1077267A (ja) * | 1996-09-03 | 1998-03-24 | Sagami Chem Res Center | ５−メトキシトリプタミン誘導体 |
| RU2141483C1 (ru) * | 1997-07-04 | 1999-11-20 | Небольсин Владимир Евгеньевич | Производные пептидов или их фармацевтически приемлемые соли, способ их получения, применение и фармацевтическая композиция |
| JP4156825B2 (ja) * | 2001-11-01 | 2008-09-24 | 株式会社ロッテ | 抗鬱・抗ストレス剤及びそれを含有する組成物 |
| AU2009239430B2 (en) * | 2008-04-21 | 2015-01-22 | Signum Biosciences, Inc. | Compounds, compositions and methods for making the same |
-
2009
- 2009-03-02 FR FR0951303A patent/FR2942625B1/fr not_active Expired - Fee Related
-
2010
- 2010-03-02 US US13/254,370 patent/US8614246B2/en not_active Expired - Fee Related
- 2010-03-02 WO PCT/EP2010/052596 patent/WO2010100133A2/fr not_active Ceased
- 2010-03-02 CN CN2010800147167A patent/CN102369185A/zh active Pending
- 2010-03-02 EP EP10705616A patent/EP2403830A2/fr not_active Withdrawn
- 2010-03-02 CA CA2754283A patent/CA2754283A1/fr not_active Abandoned
- 2010-03-02 JP JP2011552413A patent/JP2012519202A/ja active Pending
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