EA201291209A1 - Способ получения феррохина конвергентным восстановительным аминированием - Google Patents
Способ получения феррохина конвергентным восстановительным аминированиемInfo
- Publication number
- EA201291209A1 EA201291209A1 EA201291209A EA201291209A EA201291209A1 EA 201291209 A1 EA201291209 A1 EA 201291209A1 EA 201291209 A EA201291209 A EA 201291209A EA 201291209 A EA201291209 A EA 201291209A EA 201291209 A1 EA201291209 A1 EA 201291209A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- ferrohin
- restorative
- amination
- convergent
- Prior art date
Links
- 238000005576 amination reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- CVUUCFIVYYDLHL-UHFFFAOYSA-N 7-chloroquinolin-2-amine Chemical compound C1=CC(Cl)=CC2=NC(N)=CC=C21 CVUUCFIVYYDLHL-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- MYCZBBOLTYBTCX-UHFFFAOYSA-N cyclopenta-2,4-dien-1-amine;cyclopenta-1,3-diene;iron(2+) Chemical compound [Fe+2].C=1C=C[CH-]C=1.NC1=CC=C[CH-]1 MYCZBBOLTYBTCX-UHFFFAOYSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002207 metabolite Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000006268 reductive amination reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4706—4-Aminoquinolines; 8-Aminoquinolines, e.g. chloroquine, primaquine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Abstract
Изобретение относится к способу получения феррохина формулы (F) или его метаболита формулы (Fm), включающей реакцию восстановительного аминирования, при этом указанная реакция включает: (i) стадию конденсации альдегидаминоферроцена формулы (1), в которой R представляет собой атом водорода или метильную группу, с 7-хлорхинолинамином формулы (2), как показано ниже, после которой следует (ii) стадия восстановления продукта конденсации, полученного в предыдущей стадии, затем (iii) стадия гидролиза реакционной смеси в присутствии водного раствора аммиака или лимонной кислоты.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1054625A FR2961209B1 (fr) | 2010-06-11 | 2010-06-11 | Procede de synthese de la ferroquine par amination reductrice convergente. |
| PCT/IB2011/052536 WO2011154923A1 (en) | 2010-06-11 | 2011-06-10 | Method of synthesis of ferroquine by convergent reductive amination |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201291209A1 true EA201291209A1 (ru) | 2013-04-30 |
| EA020392B1 EA020392B1 (ru) | 2014-10-30 |
Family
ID=42752115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201291209A EA020392B1 (ru) | 2010-06-11 | 2011-06-10 | Способ получения феррохина конвергентным восстановительным аминированием |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US8497375B2 (ru) |
| EP (1) | EP2580224B1 (ru) |
| JP (2) | JP5916721B2 (ru) |
| KR (1) | KR101839634B1 (ru) |
| CN (1) | CN102939297B (ru) |
| AP (1) | AP3020A (ru) |
| AR (1) | AR081593A1 (ru) |
| AU (1) | AU2011263354B2 (ru) |
| BR (1) | BR112012031159A2 (ru) |
| CA (1) | CA2802161C (ru) |
| CL (1) | CL2012003455A1 (ru) |
| CO (1) | CO6602116A2 (ru) |
| EA (1) | EA020392B1 (ru) |
| FR (1) | FR2961209B1 (ru) |
| IL (1) | IL223521A (ru) |
| JO (1) | JO2928B1 (ru) |
| MA (1) | MA34363B1 (ru) |
| MX (1) | MX2012014473A (ru) |
| NZ (1) | NZ605608A (ru) |
| SG (1) | SG186247A1 (ru) |
| TW (1) | TWI485136B (ru) |
| UY (1) | UY33447A (ru) |
| WO (1) | WO2011154923A1 (ru) |
| ZA (1) | ZA201209328B (ru) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2961209B1 (fr) | 2010-06-11 | 2013-03-01 | Sanofi Aventis | Procede de synthese de la ferroquine par amination reductrice convergente. |
| CN103242378B (zh) * | 2013-05-20 | 2015-06-03 | 洛阳师范学院 | 二茂铁基嘧啶钳形配体及其制备方法 |
| CN103254250B (zh) * | 2013-05-20 | 2015-06-10 | 洛阳师范学院 | 二茂铁基吡嗪环钯氮杂环卡宾化合物及其制备方法和用途 |
| CN103242379B (zh) * | 2013-05-20 | 2015-09-02 | 洛阳师范学院 | 2-二茂铁基-芳基喹啉及其制备方法 |
| EP2821412A1 (en) * | 2013-07-01 | 2015-01-07 | Universität Zürich | Organometallic 2-cyano-2-aminobenzoate-propyl derivates and their use as anthelmintics |
| CN103848872A (zh) * | 2014-03-20 | 2014-06-11 | 内蒙古大学 | 一种含二茂铁基团的中氮茚化合物的制备方法 |
| US10370395B2 (en) | 2015-01-02 | 2019-08-06 | University Of Vermont And State Agricultural College | Cymanquine compounds and derivatives thereof and uses thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3856850B2 (ja) * | 1994-08-18 | 2006-12-13 | 生化学工業株式会社 | 光学活性アミノケトン及びアミノアルコールの製造方法 |
| FR2733985B1 (fr) * | 1995-05-10 | 1997-07-18 | Univ Lille Sciences Tech | Complexes organometalliques du fer antipaludiques |
| JP3921703B2 (ja) * | 1995-07-12 | 2007-05-30 | 住友化学株式会社 | Ｎ−（α−アルキルベンジリデン）−α−フェニルアルキルアミン |
| JPH09124576A (ja) * | 1995-10-27 | 1997-05-13 | Sumitomo Chem Co Ltd | イミン類の製造方法 |
| CA2422137A1 (en) * | 2000-09-14 | 2003-03-13 | Kaken Pharmaceutical Co., Ltd. | Tetrahydroquinoline compounds |
| CA2475332A1 (en) * | 2002-02-07 | 2003-08-14 | Sumitomo Chemical Company, Limited | Process for producing (r)-3-hydroxy-3-(2-phenylethyl)hexanoic acid and its intermediate |
| FR2884715B1 (fr) * | 2005-04-20 | 2007-06-15 | Sanofi Aventis Sa | Association entre la ferroquine et un derive d'artemisinine pour le traitement du paludisme |
| FR2961209B1 (fr) | 2010-06-11 | 2013-03-01 | Sanofi Aventis | Procede de synthese de la ferroquine par amination reductrice convergente. |
-
2010
- 2010-06-11 FR FR1054625A patent/FR2961209B1/fr active Active
-
2011
- 2011-06-09 JO JO2011190A patent/JO2928B1/en active
- 2011-06-09 AR ARP110101985A patent/AR081593A1/es unknown
- 2011-06-10 CA CA2802161A patent/CA2802161C/en active Active
- 2011-06-10 AU AU2011263354A patent/AU2011263354B2/en not_active Ceased
- 2011-06-10 MX MX2012014473A patent/MX2012014473A/es active IP Right Grant
- 2011-06-10 TW TW100120422A patent/TWI485136B/zh not_active IP Right Cessation
- 2011-06-10 UY UY0001033447A patent/UY33447A/es not_active Application Discontinuation
- 2011-06-10 EP EP11729738.2A patent/EP2580224B1/en active Active
- 2011-06-10 JP JP2013513804A patent/JP5916721B2/ja active Active
- 2011-06-10 SG SG2012090502A patent/SG186247A1/en unknown
- 2011-06-10 CN CN201180028786.2A patent/CN102939297B/zh active Active
- 2011-06-10 AP AP2012006595A patent/AP3020A/xx active
- 2011-06-10 EA EA201291209A patent/EA020392B1/ru not_active IP Right Cessation
- 2011-06-10 WO PCT/IB2011/052536 patent/WO2011154923A1/en active Application Filing
- 2011-06-10 NZ NZ605608A patent/NZ605608A/en not_active IP Right Cessation
- 2011-06-10 MA MA35540A patent/MA34363B1/fr unknown
- 2011-06-10 BR BR112012031159A patent/BR112012031159A2/pt not_active Application Discontinuation
- 2011-06-10 KR KR1020127032234A patent/KR101839634B1/ko active IP Right Grant
-
2012
- 2012-12-07 CL CL2012003455A patent/CL2012003455A1/es unknown
- 2012-12-09 IL IL223521A patent/IL223521A/en active IP Right Grant
- 2012-12-10 ZA ZA2012/09328A patent/ZA201209328B/en unknown
- 2012-12-10 US US13/709,710 patent/US8497375B2/en active Active
- 2012-12-11 CO CO12223884A patent/CO6602116A2/es not_active Application Discontinuation
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2016
- 2016-02-10 JP JP2016023254A patent/JP2016145214A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM |
|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): RU |