WO2001012597A2 - Procede de preparation de quinoleine-5,8-diones - Google Patents
Procede de preparation de quinoleine-5,8-diones Download PDFInfo
- Publication number
- WO2001012597A2 WO2001012597A2 PCT/FR2000/002295 FR0002295W WO0112597A2 WO 2001012597 A2 WO2001012597 A2 WO 2001012597A2 FR 0002295 W FR0002295 W FR 0002295W WO 0112597 A2 WO0112597 A2 WO 0112597A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coor
- formula
- chosen
- quinoline
- diones
- Prior art date
Links
Classifications
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
- C07D215/20—Oxygen atoms
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
-
- 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
- C07D215/36—Sulfur atoms
-
- 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
Definitions
- the present invention relates to a process for the preparation of quinoline-5,8-diones which find application as intermediates, in particular in the pharmaceutical industry.
- Bracher Heterocycles, 29, 2093, 1989
- This process requires a double functionalization of the quinoline nucleus and therefore uses raw materials that are not very accessible and expensive.
- S. Ghosh J. Fluorine Chem., 1994; 67: 53-56 describes quinoline-5-8diones derivatives obtained by cycloaddition between p-benzoquinone and a substituted diene.
- 4-chloroquinoline-5,8-dione is described as an intermediate for the synthesis of more complex tri or tetracyclic compounds (M. Croisy-Delsey et al., J. Heterocyclic Chem. 1993; 30: 55-60), while the 2-methoxy-quinoline-5,8-dione is a presented as a secondary product of N-alkylation of 2,5,8 (1 / - /) - quinolinet one (C. Avendano et al. Synthesis 1991; 727- 730).
- 4-hydroxy-5,8-quinoline-quinone can be synthesized from 2,5-dimethoxy aniline and the ester of methyl acrylic acid (P. Withopf et al.
- Quinoline-5.8 dione and 2-chloro-4-methyl-quinoline-5.8-dione are the starting materials used for the synthesis of azaanthraquinone derivatives (KT Potts et al., J. Org. Chem ., 1986: 2011 -2021).
- Antimalarial agents derived from 6-amino-5,8-dimethoxyquinolines are prepared from 2-trifluoro-4-methyl or from 2-4 dimethyl quinoline-5,8-dione (C. Temple et al., J. Med Chem., 1974; 17 (6): 615-619).
- EP 0433 679 describes quinoline-5,8-diones derivatives as inhibitors of the Maillard reaction in the organism, the latter being responsible (by denaturation of proteins by sugars) for several consequences of the diabetic disease (neuropathies, retinopathies ).
- the subject of the present invention is a process for the preparation of quinoline-5,8-diones of formula:
- Ri, R 2 and R 3 are chosen from hydrogen, a halogen atom, a CC 6 alkyl group , -CHO, -OH, -OR, -COOH, -CN, -C0 2 R, -CONHR, -CONRR'-, -NH 2 , -NHCOR, -CH 2 N-COOR, CH 2 -N-COOR, morpholino and
- R and R ' being chosen from dC 6 alkyl groups and Ar being a C 6 -C ⁇ 4 aryl group, in which one oxidizes with oxygen under the action of actinic radiation in solution in an organic solvent and in the presence of a catalytic amount of a sensitizer, an 8-hydroxyquinoline of formula:
- the oxidation reaction with oxygen is carried out in an organic solvent in which the starting 8-hydroxyquinoline of formula II is soluble.
- the solvent is advantageously chosen in such a way that the sensitizer is also soluble therein.
- the sensitizer can in particular be tetraphenylporphine (or TPP), in which case the solvent can be in particular dichloromethane.
- DCN dicyanonaphthalene
- DCA dicyanoanthracene
- DCB dicyano-benzene
- the reaction is advantageously carried out near ambient temperature (15 to 25 ° C) under irradiation, with visible light under oxygen bubbling, for a period which can be from 2 to 8 hours.
- the hydroperoxide formed of formula III decomposes spontaneously with stirring, in particular in the presence of Na 2 S0 4 .
- a subject of the present invention is also the quinoline-5,8-diones of formula:
- Ri, R 2 and R 3 are chosen from hydrogen, a halogen atom, a d-Ce alkyl group, -CHO, -OH, -OR, -COOH, -CN, -C0 2 R, -CONHR , - CONRR'-, -NH 2 , -NHCOR, -CH 2 N-COOR, CH 2 -N-COOR, morpholino and II
- R and R ′ being chosen from CC 6 alkyl groups and Ar being a C 6 -Cu aryl group, with the exception of the compounds in which:
- Ri H
- R2 H
- R 3 is chosen from H, CH 3 , CN and CHO.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU70112/00A AU779500B2 (en) | 1999-08-13 | 2000-08-10 | Method for preparing quinoline-5,8-diones |
CA2393951A CA2393951C (fr) | 1999-08-13 | 2000-08-10 | Procede de preparation de quinoleine-5,8-diones |
BR0013547-0A BR0013547A (pt) | 1999-08-13 | 2000-08-10 | Processo de preparação de quinoleìna-5,8-dionas |
MXPA02001494A MXPA02001494A (es) | 1999-08-13 | 2000-08-10 | Procedimiento de preparacion de quinolein-5, 8-dionas. |
JP2001516898A JP2003507363A (ja) | 1999-08-13 | 2000-08-10 | キノリン−5,8−ジオンの製造方法 |
PL353457A PL203362B1 (pl) | 1999-08-13 | 2000-08-10 | Sposób otrzymywania chinolino-5,8-dionów oraz chinolino-5,8-diony |
EP00958663A EP1202972A2 (fr) | 1999-08-13 | 2000-08-10 | Procede de preparation de quinoleine-5,8-diones |
SK205-2002A SK287416B6 (sk) | 1999-08-13 | 2000-08-10 | Spôsob prípravy chinoleín-5,8-diónov |
HU0202890A HUP0202890A3 (en) | 1999-08-13 | 2000-08-10 | Method for preparing quinoline-5,8-diones |
US10/049,375 US6515127B1 (en) | 1999-08-13 | 2000-08-10 | Method for preparing quinoline-5,8-diones |
IL14804200A IL148042A0 (en) | 1999-08-13 | 2000-08-10 | Method for preparing quinoline-5,8-diones |
NZ517041A NZ517041A (en) | 1999-08-13 | 2000-08-10 | Method for preparing quinoline-5,8-diones |
IL148042A IL148042A (en) | 1999-08-13 | 2002-02-06 | Method for making quinoline – 5,8 – deion |
NO20020670A NO322649B1 (no) | 1999-08-13 | 2002-02-11 | Kinolin-5,8-dioner, og fremgangsmate for fremstilling av kinolin-5,8-dioner |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9910491A FR2797443B1 (fr) | 1999-08-13 | 1999-08-13 | Procede de prepartion de quinoleine-5,8-diones |
FR99/10491 | 1999-08-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2001012597A2 true WO2001012597A2 (fr) | 2001-02-22 |
WO2001012597A3 WO2001012597A3 (fr) | 2001-07-19 |
Family
ID=9549144
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/002295 WO2001012597A2 (fr) | 1999-08-13 | 2000-08-10 | Procede de preparation de quinoleine-5,8-diones |
Country Status (19)
Country | Link |
---|---|
US (1) | US6515127B1 (fr) |
EP (1) | EP1202972A2 (fr) |
JP (1) | JP2003507363A (fr) |
KR (1) | KR100719398B1 (fr) |
CN (1) | CN1139575C (fr) |
AU (1) | AU779500B2 (fr) |
BR (1) | BR0013547A (fr) |
CA (1) | CA2393951C (fr) |
CZ (1) | CZ2002530A3 (fr) |
FR (1) | FR2797443B1 (fr) |
HU (1) | HUP0202890A3 (fr) |
IL (2) | IL148042A0 (fr) |
MX (1) | MXPA02001494A (fr) |
NO (1) | NO322649B1 (fr) |
NZ (1) | NZ517041A (fr) |
PL (1) | PL203362B1 (fr) |
SK (1) | SK287416B6 (fr) |
WO (1) | WO2001012597A2 (fr) |
ZA (1) | ZA200200970B (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100519533C (zh) * | 2006-12-01 | 2009-07-29 | 广东工业大学 | 5-芳胺喹啉-7,8-二酮类衍生物及其在制备抗菌药物中的应用 |
WO2010127208A1 (fr) * | 2009-04-30 | 2010-11-04 | Forest Laboratories Holdings Limited | Inhibiteurs de l'acétyl-coa carboxylase |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0433679A2 (fr) * | 1989-11-20 | 1991-06-26 | Senju Pharmaceutical Co., Ltd. | Compositions pharmaceutiques pour l'inhibition de la réaction de maillard |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4692449A (en) * | 1986-06-20 | 1987-09-08 | American Cyanamid Company | Substituted quinolinediones |
US4742059A (en) * | 1986-06-20 | 1988-05-03 | American Cyanamide Company | Substituted quinoxalinediones and their methods of use |
JPH04336792A (ja) * | 1991-05-13 | 1992-11-24 | Nippon Musen Denki Saabisushiya:Kk | グラフィック表示処理装置 |
FR2790954B1 (fr) * | 1999-03-18 | 2003-08-08 | Lafon Labor | Composition pharmaceutique a base de composes polyaromatiques |
-
1999
- 1999-08-13 FR FR9910491A patent/FR2797443B1/fr not_active Expired - Fee Related
-
2000
- 2000-08-10 IL IL14804200A patent/IL148042A0/xx active IP Right Grant
- 2000-08-10 PL PL353457A patent/PL203362B1/pl not_active IP Right Cessation
- 2000-08-10 KR KR1020027001774A patent/KR100719398B1/ko not_active IP Right Cessation
- 2000-08-10 CN CNB008116423A patent/CN1139575C/zh not_active Expired - Fee Related
- 2000-08-10 CZ CZ2002530A patent/CZ2002530A3/cs unknown
- 2000-08-10 AU AU70112/00A patent/AU779500B2/en not_active Ceased
- 2000-08-10 JP JP2001516898A patent/JP2003507363A/ja active Pending
- 2000-08-10 CA CA2393951A patent/CA2393951C/fr not_active Expired - Fee Related
- 2000-08-10 BR BR0013547-0A patent/BR0013547A/pt not_active Application Discontinuation
- 2000-08-10 HU HU0202890A patent/HUP0202890A3/hu unknown
- 2000-08-10 MX MXPA02001494A patent/MXPA02001494A/es active IP Right Grant
- 2000-08-10 US US10/049,375 patent/US6515127B1/en not_active Expired - Fee Related
- 2000-08-10 WO PCT/FR2000/002295 patent/WO2001012597A2/fr active IP Right Grant
- 2000-08-10 EP EP00958663A patent/EP1202972A2/fr not_active Withdrawn
- 2000-08-10 SK SK205-2002A patent/SK287416B6/sk not_active IP Right Cessation
- 2000-08-10 NZ NZ517041A patent/NZ517041A/en not_active IP Right Cessation
-
2002
- 2002-02-04 ZA ZA200200970A patent/ZA200200970B/en unknown
- 2002-02-06 IL IL148042A patent/IL148042A/en not_active IP Right Cessation
- 2002-02-11 NO NO20020670A patent/NO322649B1/no not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0433679A2 (fr) * | 1989-11-20 | 1991-06-26 | Senju Pharmaceutical Co., Ltd. | Compositions pharmaceutiques pour l'inhibition de la réaction de maillard |
Non-Patent Citations (8)
Title |
---|
C. AVENDAÑO ET AL.: "A comparative study of synthetic approaches ..." SYNTHESIS., - 1991 pages 727-730, XP002139239 GEORG THIEME VERLAG. STUTTGART., DE ISSN: 0039-7881 * |
CARROLL TEMPLE, JR. ET AL.: "Synthesis of potential antimalarial agents. Preparation of ..." JOURNAL OF MEDICINAL CHEMISTRY., vol. 17, no. 6, - 1974 pages 615-619, XP002139242 AMERICAN CHEMICAL SOCIETY. WASHINGTON., US ISSN: 0022-2623 * |
CHEMICAL ABSTRACTS, vol. 69, no. 3, 15 juillet 1968 (1968-07-15) Columbus, Ohio, US; abstract no. 10339f, BABU, B. HARINATH ET AL.: "Synthesis of 5:6- and 5:8-quinolinequinones" XP002139244 -& DATABASE CHEMICAL ABSTRACTS [en ligne] CA 69:10339, XP002139245 & SYMP. SYN. HETEROCYCL. COMPOUNDS PHYSIOL. INTEREST, HYDERABAD, INDIA 1964, - 1966 pages 114-118, * |
GOH MATSUO ET AL.: "Two-step synthesis of C-glycosyl juglones from unprotected sugars: a novel approach to angucycline antibiotics" CHEMICAL COMMUNICATIONS., - 1996 pages 2173-2174, XP002139243 ROYAL SOCIETY OF CHEMISTRY., GB ISSN: 1359-7345 cité dans la demande * |
KEVIN T. POTTS ET AL.: "Cycloaddition routes to azaanthraquinone deriatives. Use of azadienophiles" JOURNAL OF ORGANIC CHEMISTRY., vol. 51, no. 11, - 1986 pages 2011-2021, XP002139241 AMERICAN CHEMICAL SOCIETY. EASTON., US ISSN: 0022-3263 * |
MARTINE CROISY-DELCEY ET AL.: "Synthesis of 4-amino-substituted-6-hydroxy and 11-hydroxy-naphtho(2,3-g)quinoline-5,12-di ones ..." JOURNAL OF HETEROCYCLIC CHEMISTRY., vol. 30, no. 1, - 1993 pages 55-60, XP002139238 HETEROCORPORATION. PROVO., US ISSN: 0022-152X * |
PETER WITHOPF ET AL.: "Synthese von 8-Azajuglon( 4-hydroxy-5,8-chinolinchinon)" TETRAHEDRON., vol. 43, no. 20, - 1987 pages 4549-4554, XP002139240 ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL ISSN: 0040-4020 * |
SOMMATH GHOSH ET AL.: "(4+2)-Cycloaddition reactions employing 2-fluoro-2-alkenal N, N-dimethylhydrazones: synthsis of 3-fluoropyridines and dihydro or tetrahydro derivatives thereof" JOURNAL OF FLUORINE CHEMISTRY., vol. 67, no. 1, - 1994 pages 53-56, XP002139237 ELSEVIER SEQUOIA. LAUSANNE., CH ISSN: 0022-1139 * |
Also Published As
Publication number | Publication date |
---|---|
NZ517041A (en) | 2003-09-26 |
JP2003507363A (ja) | 2003-02-25 |
KR20020023418A (ko) | 2002-03-28 |
AU779500B2 (en) | 2005-01-27 |
US6515127B1 (en) | 2003-02-04 |
SK287416B6 (sk) | 2010-09-07 |
CA2393951C (fr) | 2010-05-25 |
PL203362B1 (pl) | 2009-09-30 |
EP1202972A2 (fr) | 2002-05-08 |
AU7011200A (en) | 2001-03-13 |
NO20020670D0 (no) | 2002-02-11 |
FR2797443A1 (fr) | 2001-02-16 |
FR2797443B1 (fr) | 2003-10-31 |
NO322649B1 (no) | 2006-11-13 |
CN1370149A (zh) | 2002-09-18 |
KR100719398B1 (ko) | 2007-05-17 |
PL353457A1 (en) | 2003-11-17 |
CA2393951A1 (fr) | 2001-02-22 |
ZA200200970B (en) | 2003-04-30 |
IL148042A (en) | 2007-06-03 |
WO2001012597A3 (fr) | 2001-07-19 |
MXPA02001494A (es) | 2002-07-02 |
BR0013547A (pt) | 2002-04-09 |
CN1139575C (zh) | 2004-02-25 |
HUP0202890A2 (hu) | 2003-01-28 |
CZ2002530A3 (cs) | 2002-05-15 |
NO20020670L (no) | 2002-04-15 |
HUP0202890A3 (en) | 2003-04-28 |
IL148042A0 (en) | 2002-09-12 |
SK2052002A3 (en) | 2002-09-10 |
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