CA1045140A - Ester of n-(8 trifluoromethyl 4- quinolyl)-anthranilate - Google Patents
Ester of n-(8 trifluoromethyl 4- quinolyl)-anthranilateInfo
- Publication number
- CA1045140A CA1045140A CA202,236A CA202236A CA1045140A CA 1045140 A CA1045140 A CA 1045140A CA 202236 A CA202236 A CA 202236A CA 1045140 A CA1045140 A CA 1045140A
- Authority
- CA
- Canada
- Prior art keywords
- que
- revendication
- acide
- trifluorométhyl
- quinolyl
- 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.)
- Expired
Links
- -1 trifluoromethyl 4- quinolyl Chemical group 0.000 title claims description 11
- 150000002148 esters Chemical class 0.000 title claims description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 230000009471 action Effects 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- VAYWXCMEIWUYBK-UHFFFAOYSA-N 2-(quinolin-4-ylamino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=NC2=CC=CC=C12 VAYWXCMEIWUYBK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003460 sulfonic acids Chemical class 0.000 abstract 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 238000007792 addition Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241000699729 Muridae Species 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000037656 Respiratory Sounds Diseases 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 206010037833 rales Diseases 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7321434A FR2233059B1 (en, 2012) | 1973-06-13 | 1973-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1045140A true CA1045140A (en) | 1978-12-26 |
Family
ID=9120866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA202,236A Expired CA1045140A (en) | 1973-06-13 | 1974-06-12 | Ester of n-(8 trifluoromethyl 4- quinolyl)-anthranilate |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3944555A (en, 2012) |
| JP (1) | JPS5032185A (en, 2012) |
| BE (1) | BE816175A (en, 2012) |
| CA (1) | CA1045140A (en, 2012) |
| CH (1) | CH585206A5 (en, 2012) |
| DE (1) | DE2428201A1 (en, 2012) |
| DK (1) | DK137182B (en, 2012) |
| FR (1) | FR2233059B1 (en, 2012) |
| GB (1) | GB1462676A (en, 2012) |
| IE (1) | IE39977B1 (en, 2012) |
| IL (1) | IL44912A (en, 2012) |
| LU (1) | LU70286A1 (en, 2012) |
| NL (1) | NL7407827A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE448091B (sv) * | 1977-12-15 | 1987-01-19 | Roussel Uclaf | Nya 2-/(4-kinolinyl)-amino/-5-fluorbensoesyraderivat, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande dessa derivat |
| FR2434808A1 (fr) * | 1978-09-01 | 1980-03-28 | Science Union & Cie | Nouveaux esters du methyl-1 piperidinol-4, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| ES512605A0 (es) * | 1982-05-06 | 1983-02-16 | Ferrer Int | "procedimiento de obtencion de nuevos derivados del acido 2-aminobenzoico". |
| CA1193598A (en) * | 1982-05-06 | 1985-09-17 | Rafael Foguet | 2-amino-benzoic acid derivatives and processes for their production |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2940974A (en) * | 1957-06-19 | 1960-06-14 | Sterling Drug Inc | 1-substituted-4-[(tertiary-or secondary-amino)-alkylimino]-1, 4-dihydroquinolines |
| US3174972A (en) * | 1961-07-10 | 1965-03-23 | Table ii | |
| CH408915A (fr) * | 1962-02-16 | 1966-03-15 | Roussel Uclaf | Procédé de préparation d'un nouveau composé utilisable, notamment, pour le traitement des manifestations inflammatoires et/ou douloureuses |
| FR7870M (en, 2012) * | 1968-11-08 | 1970-04-27 | ||
| BE785973A (fr) * | 1971-07-09 | 1973-01-08 | Roussel Uclaf | Nouvelles 4-amino quinoleines et procede de preparation |
-
1973
- 1973-06-13 FR FR7321434A patent/FR2233059B1/fr not_active Expired
-
1974
- 1974-05-29 IL IL44912A patent/IL44912A/xx unknown
- 1974-05-31 US US05/474,885 patent/US3944555A/en not_active Expired - Lifetime
- 1974-06-10 DK DK308374AA patent/DK137182B/da unknown
- 1974-06-11 LU LU70286A patent/LU70286A1/xx unknown
- 1974-06-11 DE DE19742428201 patent/DE2428201A1/de not_active Ceased
- 1974-06-11 JP JP49065659A patent/JPS5032185A/ja active Pending
- 1974-06-11 BE BE145289A patent/BE816175A/xx unknown
- 1974-06-12 NL NL7407827A patent/NL7407827A/xx not_active Application Discontinuation
- 1974-06-12 CH CH804974A patent/CH585206A5/xx not_active IP Right Cessation
- 1974-06-12 CA CA202,236A patent/CA1045140A/en not_active Expired
- 1974-06-13 GB GB2629474A patent/GB1462676A/en not_active Expired
- 1974-06-13 IE IE1245/74A patent/IE39977B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3944555A (en) | 1976-03-16 |
| FR2233059B1 (en, 2012) | 1976-09-03 |
| FR2233059A1 (en, 2012) | 1975-01-10 |
| DE2428201A1 (de) | 1975-01-09 |
| DK137182B (da) | 1978-01-30 |
| IL44912A0 (en) | 1974-07-31 |
| BE816175A (fr) | 1974-12-11 |
| JPS5032185A (en, 2012) | 1975-03-28 |
| NL7407827A (en, 2012) | 1974-12-17 |
| IE39977B1 (en) | 1979-02-14 |
| GB1462676A (en) | 1977-01-26 |
| LU70286A1 (en, 2012) | 1975-03-06 |
| DK137182C (en, 2012) | 1978-07-03 |
| IL44912A (en) | 1978-12-17 |
| CH585206A5 (en, 2012) | 1977-02-28 |
| IE39977L (en) | 1974-12-13 |
| DK308374A (en, 2012) | 1975-02-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0551230B1 (fr) | Dérivés 2-cyano 3-hydroxy énamides, leur procédé de préparation, leur application comme médicaments, les compositions pharmaceutiques les renfermant et les intermédiaires obtenus | |
| EP0070767A1 (fr) | Nouveaux dérivés de la quinoléine, leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| CH624952A5 (en, 2012) | ||
| EP0484223B1 (fr) | Nouveaux 3-cycloalkyl-propanamides, leurs formes tautomères et leurs sels, procédé de préparation, application à titre de médicaments et compositions les renfermant | |
| EP0040573B1 (fr) | Dérivés de l'acide 4-hydroxy 3-quinoléine carboxylique substitués en 2, leur préparation, leur application comme médicament, les compositions les renfermant et les intermédiaires nouveaux obtenus | |
| EP0012639A2 (fr) | Nouveaux dérivés de l'acide 3-quinoléine carboxylique, leur procédé de préparation, leur application comme médicament et les compositions pharmaceutiques les renfermant | |
| CA1045140A (en) | Ester of n-(8 trifluoromethyl 4- quinolyl)-anthranilate | |
| EP0606175B1 (fr) | Nouveaux dérivés 2-cyano 3-hydroxy propénamides, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant | |
| CH659469A5 (fr) | Derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation et les medicaments et compositions les renfermant. | |
| EP0208621A1 (fr) | Amides substitués, leur préparation et compositions qui les contiennent | |
| EP0214004B1 (fr) | Dérivés de l'acide 4-OH quinoléine carboxylique substitué en 2 par un groupement dihydroxylé éventuellement éthérifié ou estérifié, procédé et inter-médiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0210909B1 (fr) | Nouveaux alcoylamino amides et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0176444B1 (fr) | Nouveau procédé de préparation de dérivés du 4 H-1,2-4-triazole, nouveaux triazoles ainsi obtenus, leur applicication comme médicaments et les compositions pharmaceutiques les renfermant | |
| EP0196943A1 (fr) | Nouveaux dérivés 8-thiotétrahydroquinoléines et leurs sels | |
| CA1099290A (fr) | Procede de preparation du 7-amino 6,7 dihydro (5h) benzocycloheptene | |
| CA1105022A (fr) | Procede de preparation de nouveaux derives de la benzophenone | |
| CH636350A5 (fr) | Derives de l'acide 2-/(4-quinoleinyl) amino/ 5-fluorobenzoique, leurs procedes de preparation et les compositions pharmaceutiques les renfermant. | |
| EP0538100A1 (fr) | Nouveaux dérivés de l'acide fluoro quinoléine carboxylique-3 et leur préparation | |
| EP0226475A1 (fr) | Nouveaux dérivés de la diphénoxyethylamine, leur procédé d'obtention et les compositions pharmaceutiques en renfermant | |
| EP0005422A2 (fr) | Dérivés d'acides oméga-dialkylalkanoiques, leurs procédés de préparation ainsi que leur utilisation en thérapeutique | |
| EP0515257A1 (fr) | Dérivés de phényl-1 dihydro-1,4 hydroxy-3 oxo-4 pyridazines leur préparation et leur application en thérapeutique | |
| EP0187551A1 (fr) | Dérivés de la pyrazolo/4,3-c/cinnolin-3-one, leurs sels, procédé de préparation, application à titre de médicaments, compositions les renfermant et produits intermédiaires | |
| CH624090A5 (en, 2012) | ||
| CH426858A (fr) | Procédé de préparation de nouveaux dérivés colchiciques | |
| CH628629A5 (en) | Derivatives of piperidylindole and their salts |