CA1072961A - Quinoleines douees d'activite antalgique utilisables dans le traitement d'algies diverses - Google Patents
Quinoleines douees d'activite antalgique utilisables dans le traitement d'algies diversesInfo
- Publication number
- CA1072961A CA1072961A CA268,000A CA268000A CA1072961A CA 1072961 A CA1072961 A CA 1072961A CA 268000 A CA268000 A CA 268000A CA 1072961 A CA1072961 A CA 1072961A
- Authority
- CA
- Canada
- Prior art keywords
- nicotinamido
- anthranilate
- beta
- ethyl
- 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
- 150000003248 quinolines Chemical class 0.000 title claims 2
- 208000002193 Pain Diseases 0.000 title abstract description 3
- 230000036407 pain Effects 0.000 title abstract description 3
- 230000000146 antalgic effect Effects 0.000 title 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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 description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- -1 (7-chloro-4-quinolyl) anthranilate Chemical compound 0.000 claims description 3
- SJZLOWYUGKIWAK-UHFFFAOYSA-N n-(2-hydroxyethyl)pyridine-3-carboxamide Chemical compound OCCNC(=O)C1=CC=CN=C1 SJZLOWYUGKIWAK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 6
- 238000001311 chemical methods and process Methods 0.000 claims 3
- KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 abstract 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229960005038 quinisocaine Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical class C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- GWOFUCIGLDBNKM-UHFFFAOYSA-N glafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 GWOFUCIGLDBNKM-UHFFFAOYSA-N 0.000 description 3
- 229960001650 glafenine Drugs 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000010513 Stupor Diseases 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- 230000001562 ulcerogenic effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- NFIFQHSRZZNWTJ-UHFFFAOYSA-N 4,7-dichloroquinoline;hydrochloride Chemical compound Cl.ClC1=CC=NC2=CC(Cl)=CC=C21 NFIFQHSRZZNWTJ-UHFFFAOYSA-N 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 231100000064 subacute toxicity study Toxicity 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7539410A FR2335223A1 (fr) | 1975-12-19 | 1975-12-19 | Quinoleines douees d'activite antalgique utilisables dans le traitement d'algies diverses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072961A true CA1072961A (fr) | 1980-03-04 |
Family
ID=9164048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA268,000A Expired CA1072961A (fr) | 1975-12-19 | 1976-12-16 | Quinoleines douees d'activite antalgique utilisables dans le traitement d'algies diverses |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US4122181A (enExample) |
| BE (1) | BE849004A (enExample) |
| CA (1) | CA1072961A (enExample) |
| CH (1) | CH608804A5 (enExample) |
| DE (1) | DE2656852A1 (enExample) |
| ES (1) | ES454289A1 (enExample) |
| FR (1) | FR2335223A1 (enExample) |
| GB (1) | GB1565217A (enExample) |
| NL (1) | NL7613605A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5087618A (en) * | 1982-05-18 | 1992-02-11 | University Of Florida | Redox carriers for brain-specific drug delivery |
| US4829070A (en) * | 1982-05-18 | 1989-05-09 | University Of Florida | Novel redox carriers for brain-specific drug delivery |
| US4894266A (en) * | 1987-08-05 | 1990-01-16 | American National Can Company | Multiple layer packaging sheet material |
| US5082914A (en) * | 1989-12-15 | 1992-01-21 | Eastman Kodak Company | Grafted cellulose esters containing a silicon moiety |
| WO2025079680A1 (ja) * | 2023-10-13 | 2025-04-17 | 国立研究開発法人国立精神・神経医療研究センター | 神経保護剤 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1175246B (de) | 1959-12-14 | 1964-08-06 | Orsymonde Fa | Verfahren zur Herstellung des Dimethylpapa-verolin-bis-nicotinsaeureesters und seines sauren Dimaleats |
| CA731646A (en) * | 1962-05-08 | 1966-04-05 | Roussel-Uclaf | 4-(2'(.beta.-MORPHOLYLETHOXYCARBONYL) PHENYLAMINE) 7-CHLORO QUINOLEINE ET SES SELS, AINSI QUE LEUR PROCEDE DE PREPARATION |
| US3458519A (en) * | 1966-05-02 | 1969-07-29 | Parke Davis & Co | Quinolylanthranilic acid compounds and methods for their production |
| FR1566164A (enExample) | 1967-05-26 | 1969-05-09 | ||
| US4007275A (en) * | 1973-06-13 | 1977-02-08 | Roussel-Uclaf | N-(quinolyl)-anthranilates, their compositions, and use |
| US4021436A (en) * | 1974-03-15 | 1977-05-03 | Claudio Cavazza | Derivatives of nicotinic acid with amines variously substituted |
-
1975
- 1975-12-19 FR FR7539410A patent/FR2335223A1/fr active Granted
-
1976
- 1976-12-02 BE BE172920A patent/BE849004A/xx unknown
- 1976-12-07 NL NL7613605A patent/NL7613605A/xx not_active Application Discontinuation
- 1976-12-10 US US05/749,230 patent/US4122181A/en not_active Expired - Lifetime
- 1976-12-15 DE DE19762656852 patent/DE2656852A1/de not_active Withdrawn
- 1976-12-16 ES ES454289A patent/ES454289A1/es not_active Expired
- 1976-12-16 CA CA268,000A patent/CA1072961A/fr not_active Expired
- 1976-12-17 CH CH7615947A patent/CH608804A5/xx not_active IP Right Cessation
- 1976-12-17 GB GB52814/76A patent/GB1565217A/en not_active Expired
-
1978
- 1978-08-07 US US05/931,488 patent/US4152521A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BE849004A (fr) | 1977-04-01 |
| GB1565217A (en) | 1980-04-16 |
| ES454289A1 (es) | 1977-12-16 |
| FR2335223A1 (fr) | 1977-07-15 |
| US4122181A (en) | 1978-10-24 |
| US4152521A (en) | 1979-05-01 |
| FR2335223B1 (enExample) | 1978-12-22 |
| DE2656852A1 (de) | 1977-06-30 |
| CH608804A5 (enExample) | 1979-01-31 |
| NL7613605A (nl) | 1977-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |