FR1877M - - Google Patents
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- Publication number
- FR1877M FR1877M FR896833A FR896833A FR1877M FR 1877 M FR1877 M FR 1877M FR 896833 A FR896833 A FR 896833A FR 896833 A FR896833 A FR 896833A FR 1877 M FR1877 M FR 1877M
- Authority
- FR
- France
- Prior art keywords
- dose
- drug
- mice
- day
- morpholylethoxycarbonyl
- 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
- QNGUPQRODVPRDC-UHFFFAOYSA-N 7-chloroquinoline Chemical compound C1=CC=NC2=CC(Cl)=CC=C21 QNGUPQRODVPRDC-UHFFFAOYSA-N 0.000 description 14
- 239000003814 drug Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 (3-morpholylethoxy-carbonyl) phenylamino Chemical group 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
- 229960001138 acetylsalicylic acid Drugs 0.000 description 5
- 206010015150 Erythema Diseases 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000034994 death Effects 0.000 description 4
- 231100000517 death Toxicity 0.000 description 4
- 231100000321 erythema Toxicity 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229960001444 amodiaquine Drugs 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WHPKTPOZSKRBHT-UHFFFAOYSA-N methyl 2-[(7-chloroquinolin-4-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 WHPKTPOZSKRBHT-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 206010006002 Bone pain Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010010947 Coordination abnormal Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 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 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003195 fascia Anatomy 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 208000016290 incoordination Diseases 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000005360 mashing Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 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)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA731646A CA731646A (en) | 1962-05-08 | 4-(2'(.beta.-MORPHOLYLETHOXYCARBONYL) PHENYLAMINE) 7-CHLORO QUINOLEINE ET SES SELS, AINSI QUE LEUR PROCEDE DE PREPARATION | |
| FR896833A FR1877M (en, 2012) | 1962-05-08 | 1962-05-08 | |
| US27616363 US3151026A (en) | 1962-05-08 | 1963-04-29 | 4-[2'-(ß-MORPHOLYLETHOXYCARSBONYL)-PHENYLAMINO]-7-CHLORO-QUINOLINE |
| CH561163A CH411884A (fr) | 1962-05-08 | 1963-05-03 | Procédé de préparation d'un nouveau composé utilisable, notamment, pour le traitement des manifestations inflammatoires ou douloureuses |
| DER35085A DE1205102B (de) | 1962-05-08 | 1963-05-03 | Verfahren zur Herstellung von 4-[2'-(beta-Morpholinoaethoxycarbonyl)-phenylamino]-7-corchinolin |
| ES287780A ES287780A1 (es) | 1962-05-08 | 1963-05-07 | Procedimiento de preparación de la 4-[2¿-beta-morfoliletoxicarbinil) fenilamino] 7-cloro quinoleína y de sus sales |
| BR148933/63A BR6348933D0 (pt) | 1962-05-08 | 1963-05-07 | Processo de preparacao de 4-(2-(beta-morfoliletoxi-carbonil)fenilamino)7-cloro,quiloleina e de seus sais |
| GB18216/63A GB977237A (en) | 1962-05-08 | 1963-05-08 | 4-substituted amino-7-chloroquinolines |
| BE632037A BE632037A (fr) | 1962-05-08 | 1963-05-08 | Nouveau composé utilisable pour le traitement des manifestations inflammatoires ou douloureuses. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR896833A FR1877M (en, 2012) | 1962-05-08 | 1962-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR1877M true FR1877M (en, 2012) | 1963-07-26 |
Family
ID=8778468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR896833A Expired FR1877M (en, 2012) | 1962-05-08 | 1962-05-08 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3151026A (en, 2012) |
| BE (1) | BE632037A (en, 2012) |
| BR (1) | BR6348933D0 (en, 2012) |
| CA (1) | CA731646A (en, 2012) |
| CH (1) | CH411884A (en, 2012) |
| DE (1) | DE1205102B (en, 2012) |
| ES (1) | ES287780A1 (en, 2012) |
| FR (1) | FR1877M (en, 2012) |
| GB (1) | GB977237A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL25233A (en) * | 1961-10-17 | 1969-11-12 | Roussel Uclaf | Acetonides of alpha-monoglycerides of carboxyphenylamino chloro quinolines |
| NL131925C (en, 2012) * | 1966-03-17 | |||
| NL131732C (en, 2012) * | 1966-03-31 | |||
| FR7870M (en, 2012) * | 1968-11-08 | 1970-04-27 | ||
| GB1416872A (en) * | 1972-03-10 | 1975-12-10 | Wyeth John & Brother Ltd | 4-aminoquinoline derivatives |
| FR2335223A1 (fr) * | 1975-12-19 | 1977-07-15 | Fabre Sa Pierre | Quinoleines douees d'activite antalgique utilisables dans le traitement d'algies diverses |
| 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 |
| YU192782A (en) * | 1981-09-30 | 1985-04-30 | Recordati Chem Pharm | Process for obtaining anthranilic acid esters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094532A (en) * | 1960-09-09 | 1963-06-18 | Univ Michigan | Nu-(aminoalkyl)-piperidyl esters |
| NL120860C (en, 2012) * | 1960-11-25 |
-
0
- CA CA731646A patent/CA731646A/en not_active Expired
-
1962
- 1962-05-08 FR FR896833A patent/FR1877M/fr not_active Expired
-
1963
- 1963-04-29 US US27616363 patent/US3151026A/en not_active Expired - Lifetime
- 1963-05-03 DE DER35085A patent/DE1205102B/de active Pending
- 1963-05-03 CH CH561163A patent/CH411884A/fr unknown
- 1963-05-07 BR BR148933/63A patent/BR6348933D0/pt unknown
- 1963-05-07 ES ES287780A patent/ES287780A1/es not_active Expired
- 1963-05-08 GB GB18216/63A patent/GB977237A/en not_active Expired
- 1963-05-08 BE BE632037A patent/BE632037A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES287780A1 (es) | 1963-08-01 |
| CH411884A (fr) | 1966-04-30 |
| DE1205102B (de) | 1965-11-18 |
| US3151026A (en) | 1964-09-29 |
| GB977237A (en) | 1964-12-02 |
| BE632037A (fr) | 1963-11-08 |
| BR6348933D0 (pt) | 1973-07-03 |
| CA731646A (en) | 1966-04-05 |
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