FR2532939A1 - Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation, leur application comme medicament, les compositions les renfermant et les nouveaux intermediaires obtenus - Google Patents
Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation, leur application comme medicament, les compositions les renfermant et les nouveaux intermediaires obtenus Download PDFInfo
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- FR2532939A1 FR2532939A1 FR8215423A FR8215423A FR2532939A1 FR 2532939 A1 FR2532939 A1 FR 2532939A1 FR 8215423 A FR8215423 A FR 8215423A FR 8215423 A FR8215423 A FR 8215423A FR 2532939 A1 FR2532939 A1 FR 2532939A1
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000003814 drug Substances 0.000 title claims abstract description 11
- 239000000203 mixture Substances 0.000 title abstract description 21
- 239000000543 intermediate Substances 0.000 title abstract description 3
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical group C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 title description 2
- -1 4,5-dihydrothiazolyl Chemical group 0.000 claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000002253 acid Substances 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 150000007513 acids Chemical class 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 2
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract 2
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
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- 239000000047 product Substances 0.000 claims description 54
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- 238000000034 method Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 3
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- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8215423A FR2532939A1 (fr) | 1982-09-13 | 1982-09-13 | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation, leur application comme medicament, les compositions les renfermant et les nouveaux intermediaires obtenus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8215423A FR2532939A1 (fr) | 1982-09-13 | 1982-09-13 | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation, leur application comme medicament, les compositions les renfermant et les nouveaux intermediaires obtenus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2532939A1 true FR2532939A1 (fr) | 1984-03-16 |
| FR2532939B1 FR2532939B1 (enExample) | 1985-02-22 |
Family
ID=9277390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8215423A Granted FR2532939A1 (fr) | 1982-09-13 | 1982-09-13 | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation, leur application comme medicament, les compositions les renfermant et les nouveaux intermediaires obtenus |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2532939A1 (enExample) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2564835A1 (fr) * | 1984-05-23 | 1985-11-29 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2 par un groupement soufre, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
| FR2566405A1 (fr) * | 1984-06-25 | 1985-12-27 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2 par une fonction aminee, leur preparation, leur application comme medicaments, les compositions les renfermant et les intermediaires nouveaux obtenus |
| US5011931A (en) * | 1987-11-18 | 1991-04-30 | The Boots Company Plc | Process for the preparation of 1-methyl-3-methylthio-4-quinolone and the sulfinyl, and sulfonyl analogs thereof |
| WO2010102811A1 (de) | 2009-03-12 | 2010-09-16 | Grünenthal GmbH | Substituierte 2-mercaptochinolin-3-carboxamide als kcnq2/3 modulatoren |
| WO2011058113A1 (en) * | 2009-11-12 | 2011-05-19 | Ucb Pharma S.A. | Fused bicyclic pyridine and pyrazine derivatives as kinase inhibitors |
| WO2012025236A1 (en) | 2010-08-27 | 2012-03-01 | Grünenthal GmbH | Substituted 2-oxy-quinoline-3-carboxamides as kcnq2/3 modulators |
| WO2012025237A1 (en) | 2010-08-27 | 2012-03-01 | Grünenthal GmbH | Substituted 2-amino-quinoline-3-carboxamides as kcnq2/3 modulators |
| WO2012025238A1 (en) | 2010-08-27 | 2012-03-01 | Grünenthal GmbH | Substituted quinoline-3-carboxamides as kcnq2/3 modulators |
| US8178684B2 (en) | 2009-03-12 | 2012-05-15 | Gruenenthal Gmbh | Substituted nicotinamides as KCNQ2/3 modulators |
| US8207342B2 (en) | 2009-03-10 | 2012-06-26 | Gruenenthal Gmbh | Substituted 3-amino-2-mercaptoquinolines as KCNQ2/3 modulators |
| US8247573B2 (en) | 2009-03-12 | 2012-08-21 | Gruenenthal Gmbh | Substituted N-(2-mercaptopyridin-3-yl)amides as KCNQ2/3 modulators |
| US8618129B2 (en) | 2010-09-01 | 2013-12-31 | Gruenenthal Gmbh | Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as KCNQ2/3 modulators |
| US8653102B2 (en) | 2010-08-27 | 2014-02-18 | Gruenenthal Gmbh | Substituted 2-oxo- and 2-thioxo-dihydroquinoline-3-carboxamides as KCNQ2/3 modulators |
| EP2322516B1 (en) * | 2005-07-29 | 2015-09-23 | Janssen Sciences Ireland UC | Intermediates for the preparation of Macrocyclic inhibitors of hepatitis c virus |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2340735A1 (fr) * | 1976-02-11 | 1977-09-09 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
-
1982
- 1982-09-13 FR FR8215423A patent/FR2532939A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2340735A1 (fr) * | 1976-02-11 | 1977-09-09 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2564835A1 (fr) * | 1984-05-23 | 1985-11-29 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2 par un groupement soufre, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
| FR2566405A1 (fr) * | 1984-06-25 | 1985-12-27 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2 par une fonction aminee, leur preparation, leur application comme medicaments, les compositions les renfermant et les intermediaires nouveaux obtenus |
| EP0169755A3 (en) * | 1984-06-25 | 1986-04-09 | Roussel-Uclaf | 4-hydroxy-3-quinoline-carboxylic-acid derivatives substituted at 2 by a nitrogen-containing group, their preparation, their use as medicaments, compositions containing them and intermediates |
| US5011931A (en) * | 1987-11-18 | 1991-04-30 | The Boots Company Plc | Process for the preparation of 1-methyl-3-methylthio-4-quinolone and the sulfinyl, and sulfonyl analogs thereof |
| US5079264A (en) * | 1987-11-18 | 1992-01-07 | The Boots Co. Plc | Chemical process |
| EP2322516B1 (en) * | 2005-07-29 | 2015-09-23 | Janssen Sciences Ireland UC | Intermediates for the preparation of Macrocyclic inhibitors of hepatitis c virus |
| US8207342B2 (en) | 2009-03-10 | 2012-06-26 | Gruenenthal Gmbh | Substituted 3-amino-2-mercaptoquinolines as KCNQ2/3 modulators |
| CN102348692A (zh) * | 2009-03-12 | 2012-02-08 | 格吕伦塔尔有限公司 | 作为kcnq2/3调节剂的取代2-巯基喹啉-3-甲酰胺 |
| US8586755B2 (en) | 2009-03-12 | 2013-11-19 | Grünenthal GmbH | Substituted nicotinamides as KCNQ2/3 modulators |
| TWI461197B (zh) * | 2009-03-12 | 2014-11-21 | 2-mercaptoquinoline-3-carboxamide as a KCNQ2 / 3 modifier | |
| US8178684B2 (en) | 2009-03-12 | 2012-05-15 | Gruenenthal Gmbh | Substituted nicotinamides as KCNQ2/3 modulators |
| US8247573B2 (en) | 2009-03-12 | 2012-08-21 | Gruenenthal Gmbh | Substituted N-(2-mercaptopyridin-3-yl)amides as KCNQ2/3 modulators |
| JP2012520249A (ja) * | 2009-03-12 | 2012-09-06 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Ｋｃｎｑ２／３モジュレータとしての置換された２−メルカプトキノリン−３−カルボキサミド |
| US8399673B2 (en) | 2009-03-12 | 2013-03-19 | Gruenenthal Gmbh | Substituted 2-mercaptoquinoline-3-carboxamides as KCNQ2/3 modulators |
| WO2010102811A1 (de) | 2009-03-12 | 2010-09-16 | Grünenthal GmbH | Substituierte 2-mercaptochinolin-3-carboxamide als kcnq2/3 modulatoren |
| WO2011058113A1 (en) * | 2009-11-12 | 2011-05-19 | Ucb Pharma S.A. | Fused bicyclic pyridine and pyrazine derivatives as kinase inhibitors |
| US8957090B2 (en) | 2009-11-12 | 2015-02-17 | Ucb Pharma S.A. | Fused bicyclic pyridine and pyrazine derivatives as kinase inhibitors |
| CN103068804A (zh) * | 2010-08-27 | 2013-04-24 | 格吕伦塔尔有限公司 | 作为kcnq2/3调节剂的取代的2-氧基-喹啉-3-甲酰胺 |
| US8653101B2 (en) | 2010-08-27 | 2014-02-18 | Gruenenthal Gmbh | Substituted 2-oxy-quinoline-3-carboxamides as KCNQ2/3 modulators |
| JP2013536211A (ja) * | 2010-08-27 | 2013-09-19 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Ｋｃｎｑ２／３調節因子としての置換２−アミノ−キノリン−３−カルボキサミド |
| JP2013536212A (ja) * | 2010-08-27 | 2013-09-19 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Ｋｃｎｑ２／３調節因子としての置換キノリン−３−カルボキサミド |
| US8445512B2 (en) | 2010-08-27 | 2013-05-21 | Gruenenthal Gmbh | Substituted quinoline-3-carboxamides as KCNQ2/3 modulators |
| RU2595894C2 (ru) * | 2010-08-27 | 2016-08-27 | Грюненталь Гмбх | Замещенные 2-окси-хинолин-3-карбоксамиды в качестве модуляторов kcnq2/3 |
| US8653102B2 (en) | 2010-08-27 | 2014-02-18 | Gruenenthal Gmbh | Substituted 2-oxo- and 2-thioxo-dihydroquinoline-3-carboxamides as KCNQ2/3 modulators |
| US8470852B2 (en) | 2010-08-27 | 2013-06-25 | Gruenenthal Gmbh | Substituted 2-amino-quinoline-3-carboxamides as KCNQ2/3 modulators |
| WO2012025238A1 (en) | 2010-08-27 | 2012-03-01 | Grünenthal GmbH | Substituted quinoline-3-carboxamides as kcnq2/3 modulators |
| WO2012025237A1 (en) | 2010-08-27 | 2012-03-01 | Grünenthal GmbH | Substituted 2-amino-quinoline-3-carboxamides as kcnq2/3 modulators |
| US9073862B2 (en) | 2010-08-27 | 2015-07-07 | Gruenenthal Gmbh | Substituted 2-oxy-quinoline-3-carboxamides as KCNQ2/3 modulators |
| AU2011295406B2 (en) * | 2010-08-27 | 2015-08-06 | Grunenthal Gmbh | Substituted 2-amino-quinoline-3-carboxamides as KCNQ2/3 modulators |
| CN103068804B (zh) * | 2010-08-27 | 2015-08-19 | 格吕伦塔尔有限公司 | 作为kcnq2/3调节剂的取代的2-氧基-喹啉-3-甲酰胺 |
| WO2012025236A1 (en) | 2010-08-27 | 2012-03-01 | Grünenthal GmbH | Substituted 2-oxy-quinoline-3-carboxamides as kcnq2/3 modulators |
| US8618129B2 (en) | 2010-09-01 | 2013-12-31 | Gruenenthal Gmbh | Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as KCNQ2/3 modulators |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2532939B1 (enExample) | 1985-02-22 |
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| CA | Change of address | ||
| CD | Change of name or company name | ||
| ST | Notification of lapse |