TWI285634B - Indole derivatives - Google Patents
Indole derivatives Download PDFInfo
- Publication number
- TWI285634B TWI285634B TW089110620A TW89110620A TWI285634B TW I285634 B TWI285634 B TW I285634B TW 089110620 A TW089110620 A TW 089110620A TW 89110620 A TW89110620 A TW 89110620A TW I285634 B TWI285634 B TW I285634B
- Authority
- TW
- Taiwan
- Prior art keywords
- aryl
- group
- phenoxy
- alkyl
- alkoxy
- Prior art date
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- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000002537 cosmetic Substances 0.000 claims abstract description 3
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims description 88
- 229960003987 melatonin Drugs 0.000 claims description 86
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims description 85
- 125000003118 aryl group Chemical group 0.000 claims description 84
- -1 p-(3,5-dioxoisoxazolidine-4-ylmethyl)phenoxy Chemical group 0.000 claims description 45
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 25
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 23
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims description 19
- 229940074360 caffeic acid Drugs 0.000 claims description 19
- 235000004883 caffeic acid Nutrition 0.000 claims description 19
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims description 19
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
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- XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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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
- C07D209/04—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL130169A IL130169A (en) | 1999-05-27 | 1999-05-27 | Indole derivatives, and pharmaceutical preparations, skin protection preparations, and cosmetics containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI285634B true TWI285634B (en) | 2007-08-21 |
Family
ID=11072850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089110620A TWI285634B (en) | 1999-05-27 | 2000-05-31 | Indole derivatives |
Country Status (35)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL130169A (en) * | 1999-05-27 | 2006-08-20 | Neurim Pharma 1991 | Indole derivatives, and pharmaceutical preparations, skin protection preparations, and cosmetics containing them |
| MC200060A1 (fr) * | 2002-10-04 | 2003-05-28 | M Exsymol Sa | Produit de couplage entre la tryptamine et un alpha-aminoacide son procédé de préparation et son application dans le domaine de la neuro-cosmétique |
| CN1720227A (zh) | 2002-11-28 | 2006-01-11 | 苏文生命科学有限公司 | N－芳基磺酰基－3－氨基烷氧基吲哚 |
| CA2507923C (en) | 2002-12-18 | 2010-02-02 | Suven Life Sciences Limited | Tetracyclic 3-substituted indoles having serotonin receptor affinity |
| WO2005062851A2 (en) * | 2003-12-22 | 2005-07-14 | Pappolla Miguel A | Indole-3-propionamide and derivatives thereof |
| EP1715742A4 (en) * | 2004-02-20 | 2009-06-17 | Lifescape Biosciences Inc | COMPOSITIONS AND METHODS FOR SLEEPING |
| US7635710B2 (en) * | 2006-02-15 | 2009-12-22 | Neurim Pharmaceuticals (1991) Ltd. | Pyrone-indole derivatives and process for their preparation |
| US9101613B2 (en) | 2006-02-15 | 2015-08-11 | Neurim Pharmaceuticals (1991) Ltd. | Methods for treating neurological disease |
| US8094815B2 (en) * | 2006-11-13 | 2012-01-10 | Electronics Andtelecommunications Research Institute | Arithmetic method and apparatus for supporting AES and ARIA encryption/decryption functions |
| TW201119651A (en) * | 2009-10-26 | 2011-06-16 | Lg Life Sciences Ltd | Pharmaceutical composition comprising indole compound |
| GB201021103D0 (en) | 2010-12-13 | 2011-01-26 | Univ Leuven Kath | New compounds for the treatment of neurodegenerative diseases |
| FR2984122B1 (fr) * | 2011-12-16 | 2014-08-01 | Syntivia | Composition cosmetique pour stimuler les fonctions cellulaires anti-vieillissement de la peau |
| CN102584672A (zh) * | 2012-01-11 | 2012-07-18 | 合肥工业大学 | 一种5-甲氧基色胺衍生物、其制备方法及其用途 |
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|---|---|---|---|---|
| JPH04501722A (ja) * | 1988-11-14 | 1992-03-26 | ジ・アップジョン・カンパニー | 抗―糖尿病、抗―肥満症および抗―アテローム性動脈硬化症薬として有用なα―アミノ―インドール―３―酢酸 |
| AU8876591A (en) | 1990-11-02 | 1992-05-26 | Upjohn Company, The | Indole-3-methanamines useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents |
| US5403851A (en) * | 1994-04-05 | 1995-04-04 | Interneuron Pharmaceuticals, Inc. | Substituted tryptamines, phenalkylamines and related compounds |
| CA2146701A1 (en) * | 1994-04-11 | 1995-10-12 | Takashi Fujita | Heterocyclic compounds having anti-diabetic activity, their preparation and their use |
| JPH08239362A (ja) * | 1994-12-28 | 1996-09-17 | Sankyo Co Ltd | インドール誘導体 |
| CA2234166A1 (en) * | 1995-10-10 | 1997-04-17 | Patric James Hahn | N-¬2-substituted-3-(2-aminoethyl)-1h-indol-5-yl|-amides: new 5-ht1f agonists |
| US5756507A (en) * | 1995-12-14 | 1998-05-26 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| AU1463997A (en) * | 1995-12-22 | 1997-07-17 | Acea Pharmaceuticals, Inc. | Subtype-selective nmda receptor ligands and the use thereof |
| JPH09227369A (ja) * | 1996-02-27 | 1997-09-02 | Kyoichi Kobashi | 抗ヘリコバクター・ピロリ剤 |
| GB9718833D0 (en) * | 1997-09-04 | 1997-11-12 | Merck Sharp & Dohme | Therapeutic agents |
| IL130169A (en) * | 1999-05-27 | 2006-08-20 | Neurim Pharma 1991 | Indole derivatives, and pharmaceutical preparations, skin protection preparations, and cosmetics containing them |
-
1999
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2000
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- 2000-05-24 CZ CZ20014191A patent/CZ300126B6/cs not_active IP Right Cessation
- 2000-05-24 CN CNB008081050A patent/CN100425592C/zh not_active Expired - Fee Related
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- 2000-05-24 PT PT00927703T patent/PT1189583E/pt unknown
- 2000-05-24 WO PCT/IL2000/000295 patent/WO2000072815A1/en not_active Ceased
- 2000-05-24 HU HU0201338A patent/HU226776B1/hu not_active IP Right Cessation
- 2000-05-24 DK DK00927703T patent/DK1189583T3/da active
- 2000-05-24 DE DE60021384T patent/DE60021384T2/de not_active Expired - Lifetime
- 2000-05-24 AU AU46088/00A patent/AU776968B2/en not_active Ceased
- 2000-05-24 US US09/979,658 patent/US6858642B1/en not_active Expired - Fee Related
- 2000-05-24 TR TR2001/03417T patent/TR200103417T2/xx unknown
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- 2000-05-24 EP EP00927703A patent/EP1189583B1/en not_active Expired - Lifetime
- 2000-05-24 AT AT00927703T patent/ATE299876T1/de active
- 2000-05-26 TN TNTNSN00118A patent/TNSN00118A1/fr unknown
- 2000-05-26 AR ARP000102568A patent/AR029362A1/es not_active Application Discontinuation
- 2000-05-26 PE PE2000000504A patent/PE20010149A1/es not_active Application Discontinuation
- 2000-05-31 TW TW089110620A patent/TWI285634B/zh not_active IP Right Cessation
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2001
- 2001-11-22 IS IS6171A patent/IS2262B/is unknown
- 2001-11-26 NO NO20015737A patent/NO321697B1/no not_active IP Right Cessation
- 2001-12-18 BG BG106233A patent/BG65379B1/bg unknown
- 2001-12-20 ZA ZA200110437A patent/ZA200110437B/en unknown
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2005
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- 2005-10-11 CY CY20051101228T patent/CY1106049T1/el unknown
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