WO2017067670A1 - Nouveau procédé de préparation de tryptamines et de leurs dérivés - Google Patents
Nouveau procédé de préparation de tryptamines et de leurs dérivés Download PDFInfo
- Publication number
- WO2017067670A1 WO2017067670A1 PCT/EP2016/025121 EP2016025121W WO2017067670A1 WO 2017067670 A1 WO2017067670 A1 WO 2017067670A1 EP 2016025121 W EP2016025121 W EP 2016025121W WO 2017067670 A1 WO2017067670 A1 WO 2017067670A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- formula
- preparation
- conversion
- ila
- 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.)
- Ceased
Links
- 0 *CCc1c[n]c2cc(F)ccc12 Chemical compound *CCc1c[n]c2cc(F)ccc12 0.000 description 1
Classifications
-
- 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
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- C07D209/16—Tryptamines
Definitions
- aryl refers to a C6-18 cyclic aromatic group, formed by one or more rings, which may optionally be substituted with one or more substituents.
- the aromatic ring is a C6-10 ring system. Typical examples include phenyl, naphthyl and anthracenyl.
- reducing agents are boranes, mixtures of borohydrides and boran halides, borohydrides, metal hydrides, metal catalysts, metal cations, metal amalgams, hydrazines, silanes, siloxanes, hydrosulfite, dithionite, sulfonate, phosphines, phosphites, hypophosphites, phosphorous acid, carbon, carbon monoxide, oxalic acid, formic acid, ascorbic acid, FLP reagents, hydrogen and mixtures thereof.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
La présente invention concerne un nouveau procédé pour la préparation de tryptamine, de ses dérivés substitués et d'intermédiaires pour la préparation de ceux-ci.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201680061481.4A CN108271369A (zh) | 2015-10-23 | 2016-10-19 | 用于制备色胺及其衍生物的新工艺 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP2015002105 | 2015-10-23 | ||
| EPPCT/EP2015/002105 | 2015-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2017067670A1 true WO2017067670A1 (fr) | 2017-04-27 |
Family
ID=57209421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2016/025121 Ceased WO2017067670A1 (fr) | 2015-10-23 | 2016-10-19 | Nouveau procédé de préparation de tryptamines et de leurs dérivés |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN108271369A (fr) |
| AR (1) | AR106423A1 (fr) |
| WO (1) | WO2017067670A1 (fr) |
Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995026723A1 (fr) | 1994-04-05 | 1995-10-12 | Interneuron Pharmaceuticals, Inc. | Nouvelles phenalkylamines et tryptamines substituees, et composes apparentes |
| WO1997040024A1 (fr) | 1996-04-23 | 1997-10-30 | Merck & Co., Inc. | Inhibiteurs de thrombine a base de pyrazinone |
| WO2001068648A1 (fr) | 2000-03-15 | 2001-09-20 | Aventis Pharma Deutschland Gmbh | Beta-carbolines substituees ayant une activite inhibitrice de l'ikb-kinase |
| WO2002078693A2 (fr) | 2001-03-29 | 2002-10-10 | Eli Lilly And Company | N-(2-arylethyl)benzylamines utilisees en tant qu'antagonistes du recepteur 5-ht6 |
| WO2003014127A1 (fr) | 2001-08-07 | 2003-02-20 | Pharma Mar, S.A. | Analogues antitumoraux |
| WO2004043967A1 (fr) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Derives de cyclohexane spirocycliques |
| WO2004092167A1 (fr) | 2003-04-09 | 2004-10-28 | Millennium Pharmaceuticals, Inc. | Beta-carbolines utiles pour traiter une maladie inflammatoire |
| WO2005056554A2 (fr) | 2003-12-02 | 2005-06-23 | Exelixis, Inc. | Derives d'azepinoindole en tant qu'agents pharmaceutiques |
| WO2005111037A1 (fr) | 2004-04-09 | 2005-11-24 | Millennium Pharmaceuticals, Inc. | Utilisation de beta-carbolines pour le traitement de maladies inflammatoires |
| WO2008006583A1 (fr) | 2006-07-14 | 2008-01-17 | Novartis Ag | Dérivés de la pyrimidine en tant qu'inhibiteurs d'alk-5 |
| WO2009073118A1 (fr) | 2007-12-04 | 2009-06-11 | Merck & Co., Inc. | Tryptamine sulfonamides en tant qu'antagonistes de 5-ht6 |
| WO2010044054A1 (fr) | 2008-10-14 | 2010-04-22 | Actelion Pharmaceuticals Ltd | Dérivés de phénéthylamide et leurs analogues hétérocycliques |
| WO2010080864A1 (fr) | 2009-01-12 | 2010-07-15 | Array Biopharma Inc. | Composés contenant de la pipéridine et leurs utilisations |
| WO2010142081A1 (fr) | 2009-06-12 | 2010-12-16 | 华为技术有限公司 | Procédé de transmission de messages vidéo, équipement formant routeur, et système |
| WO2011076212A2 (fr) | 2009-12-23 | 2011-06-30 | H. Lundbeck A/S | Procédés de fabrication d'un principe pharmaceutiquement actif |
| CN102659662A (zh) * | 2012-03-28 | 2012-09-12 | 华东师范大学 | 3-r-3-羟基-2-氧化吲哚类化合物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1572647B1 (fr) * | 2002-12-20 | 2016-09-21 | Basf Se | Préparation d´amines et de leurs intermédiaires |
| DE102006033109A1 (de) * | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
-
2016
- 2016-10-19 WO PCT/EP2016/025121 patent/WO2017067670A1/fr not_active Ceased
- 2016-10-19 CN CN201680061481.4A patent/CN108271369A/zh active Pending
- 2016-10-21 AR ARP160103209A patent/AR106423A1/es unknown
Patent Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995026723A1 (fr) | 1994-04-05 | 1995-10-12 | Interneuron Pharmaceuticals, Inc. | Nouvelles phenalkylamines et tryptamines substituees, et composes apparentes |
| WO1997040024A1 (fr) | 1996-04-23 | 1997-10-30 | Merck & Co., Inc. | Inhibiteurs de thrombine a base de pyrazinone |
| WO2001068648A1 (fr) | 2000-03-15 | 2001-09-20 | Aventis Pharma Deutschland Gmbh | Beta-carbolines substituees ayant une activite inhibitrice de l'ikb-kinase |
| WO2002078693A2 (fr) | 2001-03-29 | 2002-10-10 | Eli Lilly And Company | N-(2-arylethyl)benzylamines utilisees en tant qu'antagonistes du recepteur 5-ht6 |
| WO2003014127A1 (fr) | 2001-08-07 | 2003-02-20 | Pharma Mar, S.A. | Analogues antitumoraux |
| WO2004043967A1 (fr) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Derives de cyclohexane spirocycliques |
| WO2004092167A1 (fr) | 2003-04-09 | 2004-10-28 | Millennium Pharmaceuticals, Inc. | Beta-carbolines utiles pour traiter une maladie inflammatoire |
| WO2005056554A2 (fr) | 2003-12-02 | 2005-06-23 | Exelixis, Inc. | Derives d'azepinoindole en tant qu'agents pharmaceutiques |
| WO2005111037A1 (fr) | 2004-04-09 | 2005-11-24 | Millennium Pharmaceuticals, Inc. | Utilisation de beta-carbolines pour le traitement de maladies inflammatoires |
| WO2008006583A1 (fr) | 2006-07-14 | 2008-01-17 | Novartis Ag | Dérivés de la pyrimidine en tant qu'inhibiteurs d'alk-5 |
| WO2009073118A1 (fr) | 2007-12-04 | 2009-06-11 | Merck & Co., Inc. | Tryptamine sulfonamides en tant qu'antagonistes de 5-ht6 |
| WO2010044054A1 (fr) | 2008-10-14 | 2010-04-22 | Actelion Pharmaceuticals Ltd | Dérivés de phénéthylamide et leurs analogues hétérocycliques |
| WO2010080864A1 (fr) | 2009-01-12 | 2010-07-15 | Array Biopharma Inc. | Composés contenant de la pipéridine et leurs utilisations |
| WO2010142081A1 (fr) | 2009-06-12 | 2010-12-16 | 华为技术有限公司 | Procédé de transmission de messages vidéo, équipement formant routeur, et système |
| WO2011076212A2 (fr) | 2009-12-23 | 2011-06-30 | H. Lundbeck A/S | Procédés de fabrication d'un principe pharmaceutiquement actif |
| CN102659662A (zh) * | 2012-03-28 | 2012-09-12 | 华东师范大学 | 3-r-3-羟基-2-氧化吲哚类化合物的合成方法 |
Non-Patent Citations (24)
| Title |
|---|
| A. W. GREGORY; P. JAKUBEC; P. TURNER; D. J. DIXON: "Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade", ORGANIC LETTERS, vol. 15, 2013, pages 4330 |
| B. LOPEZ-IGLESIAS; C. PEREZ; J. A. MORALES-GARCIA; S. ALONSO-GIL; A. PEREZ-CASTILLO; A. ROMERO; M. G. LOPEZ; M. VILLARROYA; S. CON: "New Melatonin-N,N-Dibenzyl(N-methyl)amine Hybrids: Potent Neurogenic Agents with Antioxidant, Cholinergic, and Neuroprotective Properties as Innovative Drugs for Alzheimer's Disease", J. MED. CHEM., vol. 57, 2014, pages 3773 |
| BERGE ET AL., J. PHARM. SCI., vol. 66, no. 1, 1977, pages 19 |
| C. LIU; Q. YIN; L.-X. DAI; S.-L. YOU: "Synthesis of pyrroloindolines and furoindolines via cascade dearomatization of indole derivatives with carbenium ion", CHEM. COMM., vol. 51, 2015, pages 5971 |
| D. W. STEPHAN, J. AM. CHEM. SOC., vol. 137, 2015, pages 10018 |
| D. W. STEPHAN; G. ERKER, CURR. CHEM., 2013, pages 332 |
| D.-H. ZHANG; X.-Y. TANG; Y. WEI; M. SHI: "Rhodium(I)-Catalyzed Cycloisomerization of Nitrogen-Tethered Indoles and Alkylidenecyclopropanes: Convenient Access to Polycyclic Indole Derivatives", CHEM. EUR. J., vol. 19, 2013, pages 13668 |
| I. AILLAUD; D. M. BARBER; A. L. THOMPSON; D. J. DIXON: "Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas", ORGANIC LETTERS, vol. 15, 2013, pages 2946 |
| I. T. RAHEEM; P. S. THIARA; E. A. PETERSON; E. N. JACOBSEN: "Enantioselective Pictet-Spengler-Type Cyclizations of Hydroxylactams: H-Bond Donor Catalysis by Anion Binding", J. AM. CHEM. SOC., vol. 129, 2007, pages 13404, XP002626111, DOI: doi:10.1021/JA076179W |
| L. J. HOUNJET; D. W. STEPHAN, ORG. PROC. RES. DEV., vol. 18, 2014, pages 385 |
| L. LIU; L. ZHANG: "Access to Electron-Rich Arene-Fused Hexahydroquinolizinones through a Gold-Catalysis-Initiated Cascade Process", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 51, no. 29, 2012, pages 7301 |
| M. A. KABESHOV; B. MUSIO; P. R. D. MURRAY; D. L. BROWNE; S. V. LEY: "Expedient Preparation of Nazlinine and a Small Library of Indole Alkaloids Using Flow Electrochemistry as an Enabling Technology", ORGANIC LETTERS, vol. 16, no. 17, 2014, pages 4618 |
| M. B. SMITH; J. MARCH: "March 's Advanced Organic Chemistry", JOHN WILEY & SONS, ISBN: 13:978-0-471- |
| M. E. MURATORE; C. A. HOLLOWAY; A. W. PILLING; R. I. STORER; G, TREVITT; D, J. DIXON: "Enantioselective Bronsted Acid-Catalyzed N-Acyliminium Cyclization Cascades", J. AM. CHEM. SOC., vol. 131, 2009, pages 10796 |
| M. JIDA; O.-M. SOUEIDAN; B. DEPREZ; G. LACONDE; R. DEPREZ-POULAIN: "Racemic and diastereoselective construction of indole alkaloids under solvent- and catalyst-free microwave-assisted Pictet-Spengler condensation", GREEN CHEMISTRY, vol. 14, 2012, pages 909 |
| N. K. KAUSHIK; N. KAUSHIK; P. ATTRI; N. KUMAR; C. H. KIM; A. K. VERMA; E. H. CHOI: "Biomedical importance of indoles", MOLECULES, vol. 18, 2013, pages 6620 |
| QIAO REN ET AL: "Highly Efficient Assembly of 3-Hydroxy Oxindole Scaffold via a Catalytic Decarboxylative [1,2]-Addition Strategy", ACS CATALYSIS, vol. 2, no. 12, 7 December 2012 (2012-12-07), US, pages 2622 - 2625, XP055325611, ISSN: 2155-5435, DOI: 10.1021/cs300628w * |
| S. S. ZIMMERMAN; A. KHATRI; E. C. GARNIER-AMBLARD; P. MULLASSERIL; N. L. KURTKAYA; S. GYONEVA; K. B. HANSEN; S. F. TRAYNELIS; D. C: "Design, Synthesis, and Structure-Activity Relationship of a Novel Series of GluN2C-Selective Potentiators", J. MED. CHEM., vol. 57, 2014, pages 2334 |
| TAO DENG ET AL: "Copper-Catalyzed Asymmetric Addition to Isatins to give 3-Hydroxy-2-oxindoles by C-H Activation", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2014, no. 32, 29 September 2014 (2014-09-29), DE, pages 7259 - 7264, XP055325598, ISSN: 1434-193X, DOI: 10.1002/ejoc.201402852 * |
| V. PRATAP REDDY GAJULAPALLI ET AL: "Organocatalytic asymmetric decarboxylative cyanomethylation of isatins using l-proline derived bifunctional thiourea", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 12, no. 24, 1 January 2014 (2014-01-01), GB, pages 4186, XP055325603, ISSN: 1477-0520, DOI: 10.1039/c4ob00271g * |
| X. ZHAO; X. LIU; H. MEI; J. GUO; L. LIN; X. FENG: "Asymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines", ANGEW. CHEM. INT. ED., vol. 54, 2015, pages 4032 |
| Z. LI; J. LI; N. YANG; Y. CHEN; Y. ZHOU; X. JI; L. ZHANG; J. WANG; X. XIE; H. LIU: "Gold(I)-Catalyzed Cascade Approach for the Synthesis of Tryptamine-Based Polycyclic Privileged Scaffolds as al-Adrenergic Receptor Antagonists", JOURNAL OF ORGANIC CHEMISTRY, vol. 78, 2013, pages 10802 |
| Z. SHEN; Z. XIA; H. ZHAO; J. HU; X. WAN; Y. LAI; C. ZHU; W, XIE: "Synthesis of naked amino-pyrroloindoline via direct aminocyclization of tryptamine", ORG. BIOM. CHEM., vol. 13, 2015, pages 5381 |
| ZHONG-HUA GAO ET AL: "Four new indole alkaloids from Plantago asiatica", NATURAL PRODUCTS AND BIOPROSPECTING, vol. 2, no. 6, 20 December 2012 (2012-12-20), pages 249 - 254, XP055325605, ISSN: 2192-2195, DOI: 10.1007/s13659-012-0082-4 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AR106423A1 (es) | 2018-01-10 |
| CN108271369A (zh) | 2018-07-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| He et al. | Metal-free photocatalyzed aerobic oxidative C sp3–H functionalization of glycine derivatives: One-step generation of quinoline-fused lactones | |
| Hadjeri et al. | Alkylation of 2-phenyl-4-quinolones: Synthetic and structural studies | |
| Ren et al. | Effective and diastereoselective preparation of dispiro [cyclopent-3′-ene] bisoxindoles via novel [3+ 2] annulation of isoindigos and MBH carbonates | |
| Sharghi et al. | Synthesis of new lariat ethers containing polycyclic phenols and heterocyclic aromatic compound on graphite surface via mannich reaction | |
| Neo et al. | An easy synthesis of diversely functionalized 2H-chromenes and amido amines by an enol-Ugi reaction | |
| KR100788529B1 (ko) | 3-(1-히드록시-펜틸리덴)-5-니트로-3h-벤조푸란-2-온,그의 제조 방법 및 용도 | |
| Schlosser et al. | Three complementary methods offering access to 5-substituted 1, 2, 3, 4-tetrahydroisoquinolines | |
| WO2017067670A1 (fr) | Nouveau procédé de préparation de tryptamines et de leurs dérivés | |
| Kefayati et al. | An environmental friendly approach for the synthesis of spiro [indoline‐3′, 2‐quinazoline] 2′, 4 (3H)‐dione using 1‐methylimidazolium hydrogen sulfate, as reusable catalyst | |
| Mo et al. | Studies toward the Synthesis of (R)‐(+)‐Harmicine | |
| Sreenivas et al. | Copper-mediated domino synthesis of pyrimido [4, 5-b] carbazolones via Ullmann N-arylation and aerobic oxidative C–H amidation | |
| Mu et al. | Synthesis of indoline-fused eight-membered azaheterocycles through Zn-catalyzed dearomatization of indoles and subsequent base-promoted C–C activation | |
| CN110981790B (zh) | 一种1,4-二氢吡啶类衍生物及其合成方法 | |
| Kovalskiy et al. | Synthesis of 7-(3-piperidyl)-[1, 6] naphthyridine and 7-(4-pipe-ridyl)[1, 6] naphthyridine. | |
| CN110776510B (zh) | 一种1-(2-喹啉基)-β-咔啉天然产物及衍生物的制备方法 | |
| Min et al. | An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid | |
| RU2429235C2 (ru) | Способ получения замещенных бензофуран-5,6-дикарбонитрилов | |
| Das et al. | A Simple Synthesis of Benzodiazonines from C-2 Arylated 1, 3-Indanediones | |
| Zhou et al. | A FACILE SYNTHESIS OF ISOCOUMARINO [3’, 4’: 4, 5] PYRROLO [3, 2-c]-COUMARINS FROM 4-AMINOCOUMARINS AND NINHYDRIN | |
| Balamurali et al. | Synthesis of tetracyclic carbazole derivatives | |
| Xie et al. | Iron/O2-Promoted CH Bond Functionalization for the Exclusive Synthesis of 2-Quinoline Carboxaldehydes under Microwave Irradiation | |
| KR101155389B1 (ko) | 에네-아마이드 유도체의 제조 방법 | |
| Salem et al. | An expedient synthesis of novel bis [thienopyridines] linked to arene or heteroarene core as novel hybrid molecules | |
| Elzanate | A novel synthetic route to nitrosopyridine-2 (1H)-thiones and nitroso-N-arylpyridones | |
| CN120004820B (zh) | 一种利用co2制备苯并噻唑类化合物的方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16788028 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 16788028 Country of ref document: EP Kind code of ref document: A1 |