CA2393951A1 - Procede de preparation de quinoleine-5,8-diones - Google Patents
Procede de preparation de quinoleine-5,8-diones Download PDFInfo
- Publication number
- CA2393951A1 CA2393951A1 CA002393951A CA2393951A CA2393951A1 CA 2393951 A1 CA2393951 A1 CA 2393951A1 CA 002393951 A CA002393951 A CA 002393951A CA 2393951 A CA2393951 A CA 2393951A CA 2393951 A1 CA2393951 A1 CA 2393951A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- chosen
- diones
- cooh
- quinoline
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract 5
- NVJSPQCVDHGYRE-UHFFFAOYSA-N quinoline-5,8-dione Chemical class C1=CC=C2C(=O)C=CC(=O)C2=N1 NVJSPQCVDHGYRE-UHFFFAOYSA-N 0.000 title claims abstract 5
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims abstract 2
- 229960003540 oxyquinoline Drugs 0.000 claims abstract 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical group C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 claims 1
- 238000006213 oxygenation reaction Methods 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
Abstract
La présente invention concerne un procédé de préparation de quinoléine-5,8- diones de formule (I) dans laquelle: R1, R2 et R3 sont tels que définis à la revendication 1, par photo-oxygénation d'une 8-hydroxyquinoléine.
Claims (5)
1. Procédé de préparation de quinoléine-5,8-diones de formule:
dans laquelle:
R1, R2 et R3 sont choisis parmi l'hydrogène, un atome d'halogène, un groupe alkyle en C1-C6, -CHO, -OH, -OR, -COOH, -CN, -CO2R, -CONHR, -CONRR'-, -NH2, -NHCOR, morpholino et SO3H, R et R' étant choisis parmi les groupes alkyle en C1-C6 et Ar étant un groupe aryle en C6-C14, dans lequel on oxyde par l'oxygène sous l'action d'un rayonnement actinique, en solution dans un solvant organique et en présence d'une quantité
catalytique d'un sensibilisateur, une 8-hydroxyquinoléine de formule:
dans laquelle R1, R2 et R3 ont la signification donnée ci-dessus, puis l'hydroperoxyde formé, de formule:
est décomposé en composé de formule I.
dans laquelle:
R1, R2 et R3 sont choisis parmi l'hydrogène, un atome d'halogène, un groupe alkyle en C1-C6, -CHO, -OH, -OR, -COOH, -CN, -CO2R, -CONHR, -CONRR'-, -NH2, -NHCOR, morpholino et SO3H, R et R' étant choisis parmi les groupes alkyle en C1-C6 et Ar étant un groupe aryle en C6-C14, dans lequel on oxyde par l'oxygène sous l'action d'un rayonnement actinique, en solution dans un solvant organique et en présence d'une quantité
catalytique d'un sensibilisateur, une 8-hydroxyquinoléine de formule:
dans laquelle R1, R2 et R3 ont la signification donnée ci-dessus, puis l'hydroperoxyde formé, de formule:
est décomposé en composé de formule I.
2. Procédé selon la revendication 1, dans lequel le sensibilisateur est la tétraphénylporphine.
3. Procédé selon la revendication 1 ou la revendication 2, dans lequel le solvant est le dichlorométhane.
4. Quinoléine-5,8-diones de formule:
dans laquelle:
R1, R2 et R3 sont choisis parmi l'hydrogène, un atome d'halogène, un groupe alkyle en C1-C6, -CHO, -OH, -OR, -COOH, -CN, -CO2R, -CONHR, -CONRR'-, -NH2, -NHCOR, morpholino et SO3H, R et R' étant choisis parmi les groupes alkyle en C1-C6 et Ar étant un groupe aryle en C6-C14, à l'exception des composés dans lesquels:
R1 = H, R2 = H et R3 est choisi parmi H, CH3, CN et CHO.
R1 = H ou CH3, R2 = F et R3 = H
R1 = Cl, R2 = H et R3 = H
R1 = OH, R2 = H et R3 = COOH, COOCH3 ou CH3 R1 = OH, R2 = COOH ou COOC2H5 et R3 = H
R1 = H, R2 = H et R3 = OCH3 R1 = OH, R2 = H et R3 = H
R1 = OCH3, R2 = H et R3 = H
R1 = CH3, R2 = H et R3 = Cl R1 = CH3, R2 = H et R3 = CH3
dans laquelle:
R1, R2 et R3 sont choisis parmi l'hydrogène, un atome d'halogène, un groupe alkyle en C1-C6, -CHO, -OH, -OR, -COOH, -CN, -CO2R, -CONHR, -CONRR'-, -NH2, -NHCOR, morpholino et SO3H, R et R' étant choisis parmi les groupes alkyle en C1-C6 et Ar étant un groupe aryle en C6-C14, à l'exception des composés dans lesquels:
R1 = H, R2 = H et R3 est choisi parmi H, CH3, CN et CHO.
R1 = H ou CH3, R2 = F et R3 = H
R1 = Cl, R2 = H et R3 = H
R1 = OH, R2 = H et R3 = COOH, COOCH3 ou CH3 R1 = OH, R2 = COOH ou COOC2H5 et R3 = H
R1 = H, R2 = H et R3 = OCH3 R1 = OH, R2 = H et R3 = H
R1 = OCH3, R2 = H et R3 = H
R1 = CH3, R2 = H et R3 = Cl R1 = CH3, R2 = H et R3 = CH3
5. Quinoléines-5,8-diones selon la revendication 4 de formule I dans laquelle R3 est choisi parmi les groupes -CONRR' et
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR99/10491 | 1999-08-13 | ||
| FR9910491A FR2797443B1 (fr) | 1999-08-13 | 1999-08-13 | Procede de prepartion de quinoleine-5,8-diones |
| PCT/FR2000/002295 WO2001012597A2 (fr) | 1999-08-13 | 2000-08-10 | Procede de preparation de quinoleine-5,8-diones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2393951A1 true CA2393951A1 (fr) | 2001-02-22 |
| CA2393951C CA2393951C (fr) | 2010-05-25 |
Family
ID=9549144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2393951A Expired - Fee Related CA2393951C (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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4742059A (en) * | 1986-06-20 | 1988-05-03 | American Cyanamide Company | Substituted quinoxalinediones and their methods of use |
| US4692449A (en) * | 1986-06-20 | 1987-09-08 | American Cyanamid Company | Substituted quinolinediones |
| JPH03161441A (ja) * | 1989-11-20 | 1991-07-11 | Senjiyu Seiyaku Kk | メイラード反応阻害剤 |
| 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 HU HU0202890A patent/HUP0202890A3/hu unknown
- 2000-08-10 EP EP00958663A patent/EP1202972A2/fr not_active Withdrawn
- 2000-08-10 CN CNB008116423A patent/CN1139575C/zh not_active Expired - Fee Related
- 2000-08-10 JP JP2001516898A patent/JP2003507363A/ja active Pending
- 2000-08-10 KR KR1020027001774A patent/KR100719398B1/ko not_active IP Right Cessation
- 2000-08-10 NZ NZ517041A patent/NZ517041A/en not_active IP Right Cessation
- 2000-08-10 PL PL353457A patent/PL203362B1/pl not_active IP Right Cessation
- 2000-08-10 US US10/049,375 patent/US6515127B1/en not_active Expired - Fee Related
- 2000-08-10 CZ CZ2002530A patent/CZ2002530A3/cs unknown
- 2000-08-10 CA CA2393951A patent/CA2393951C/fr not_active Expired - Fee Related
- 2000-08-10 AU AU70112/00A patent/AU779500B2/en not_active Ceased
- 2000-08-10 WO PCT/FR2000/002295 patent/WO2001012597A2/fr active IP Right Grant
- 2000-08-10 MX MXPA02001494A patent/MXPA02001494A/es active IP Right Grant
- 2000-08-10 SK SK205-2002A patent/SK287416B6/sk not_active IP Right Cessation
- 2000-08-10 IL IL14804200A patent/IL148042A0/xx active IP Right Grant
- 2000-08-10 BR BR0013547-0A patent/BR0013547A/pt not_active Application Discontinuation
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| US6515127B1 (en) | 2003-02-04 |
| MXPA02001494A (es) | 2002-07-02 |
| HUP0202890A2 (hu) | 2003-01-28 |
| IL148042A (en) | 2007-06-03 |
| SK287416B6 (sk) | 2010-09-07 |
| WO2001012597A3 (fr) | 2001-07-19 |
| CZ2002530A3 (cs) | 2002-05-15 |
| AU7011200A (en) | 2001-03-13 |
| JP2003507363A (ja) | 2003-02-25 |
| CN1370149A (zh) | 2002-09-18 |
| HUP0202890A3 (en) | 2003-04-28 |
| NZ517041A (en) | 2003-09-26 |
| WO2001012597A2 (fr) | 2001-02-22 |
| FR2797443A1 (fr) | 2001-02-16 |
| NO20020670L (no) | 2002-04-15 |
| SK2052002A3 (en) | 2002-09-10 |
| ZA200200970B (en) | 2003-04-30 |
| BR0013547A (pt) | 2002-04-09 |
| PL353457A1 (en) | 2003-11-17 |
| AU779500B2 (en) | 2005-01-27 |
| KR20020023418A (ko) | 2002-03-28 |
| FR2797443B1 (fr) | 2003-10-31 |
| CN1139575C (zh) | 2004-02-25 |
| PL203362B1 (pl) | 2009-09-30 |
| KR100719398B1 (ko) | 2007-05-17 |
| EP1202972A2 (fr) | 2002-05-08 |
| NO322649B1 (no) | 2006-11-13 |
| IL148042A0 (en) | 2002-09-12 |
| NO20020670D0 (no) | 2002-02-11 |
| CA2393951C (fr) | 2010-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |