CA1106376A - Procede de preparation de nouveaux esters anthraniliques - Google Patents
Procede de preparation de nouveaux esters anthraniliquesInfo
- Publication number
- CA1106376A CA1106376A CA199,329A CA199329A CA1106376A CA 1106376 A CA1106376 A CA 1106376A CA 199329 A CA199329 A CA 199329A CA 1106376 A CA1106376 A CA 1106376A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- trifluoromethyl
- quinolyl
- piperazinyl
- halogen atom
- 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
- 238000000034 method Methods 0.000 title claims abstract description 23
- 150000002148 esters Chemical class 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 6
- 239000011707 mineral Substances 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims abstract description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 claims abstract 4
- 150000007524 organic acids Chemical class 0.000 claims abstract 4
- 235000005985 organic acids Nutrition 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims description 10
- -1 atom halogen Chemical class 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- HXOIESYGIXBVCW-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperazin-1-yl]ethanol Chemical compound C1CN(C(O)C)CCN1C1=CC=C(Cl)C=C1 HXOIESYGIXBVCW-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 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 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7317069A FR2228482B1 (enrdf_load_stackoverflow) | 1973-05-11 | 1973-05-11 | |
| FR7317069 | 1973-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1106376A true CA1106376A (fr) | 1981-08-04 |
Family
ID=9119165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA199,329A Expired CA1106376A (fr) | 1973-05-11 | 1974-05-08 | Procede de preparation de nouveaux esters anthraniliques |
Country Status (14)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR7870M (enrdf_load_stackoverflow) * | 1968-11-08 | 1970-04-27 | ||
| BE754587A (fr) * | 1969-08-08 | 1971-02-08 | Upjohn Co | Nouveaux p-(trihalomethylquinolylamino) benzamides et leur procede de preparation |
| BE785973A (fr) * | 1971-07-09 | 1973-01-08 | Roussel Uclaf | Nouvelles 4-amino quinoleines et procede de preparation |
-
1973
- 1973-05-11 FR FR7317069A patent/FR2228482B1/fr not_active Expired
-
1974
- 1974-04-24 IL IL44708A patent/IL44708A0/xx unknown
- 1974-04-26 ZA ZA00742658A patent/ZA742658B/xx unknown
- 1974-05-02 JP JP49048850A patent/JPS5014688A/ja active Pending
- 1974-05-04 ES ES425974A patent/ES425974A1/es not_active Expired
- 1974-05-08 CA CA199,329A patent/CA1106376A/fr not_active Expired
- 1974-05-09 AU AU68767/74A patent/AU6876774A/en not_active Expired
- 1974-05-09 LU LU70024A patent/LU70024A1/xx unknown
- 1974-05-09 BE BE144130A patent/BE814792A/xx unknown
- 1974-05-09 NL NL7406229A patent/NL7406229A/xx not_active Application Discontinuation
- 1974-05-10 DE DE2422848A patent/DE2422848A1/de not_active Ceased
- 1974-05-10 CH CH646174A patent/CH585225A5/xx not_active IP Right Cessation
- 1974-05-10 IE IE1002/74A patent/IE40385B1/xx unknown
- 1974-05-13 GB GB2109074A patent/GB1472652A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE814792A (fr) | 1974-11-12 |
| FR2228482A1 (enrdf_load_stackoverflow) | 1974-12-06 |
| LU70024A1 (enrdf_load_stackoverflow) | 1974-11-28 |
| IE40385B1 (en) | 1979-05-23 |
| GB1472652A (en) | 1977-05-04 |
| IL44708A0 (en) | 1974-06-30 |
| ES425974A1 (es) | 1976-07-01 |
| NL7406229A (enrdf_load_stackoverflow) | 1974-11-13 |
| AU6876774A (en) | 1975-11-13 |
| IE40385L (en) | 1974-11-11 |
| ZA742658B (en) | 1975-05-28 |
| FR2228482B1 (enrdf_load_stackoverflow) | 1976-05-14 |
| DE2422848A1 (de) | 1974-11-28 |
| CH585225A5 (enrdf_load_stackoverflow) | 1977-02-28 |
| JPS5014688A (enrdf_load_stackoverflow) | 1975-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |