DE2656852A1 - 4-amino-chinolinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
4-amino-chinolinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2656852A1 DE2656852A1 DE19762656852 DE2656852A DE2656852A1 DE 2656852 A1 DE2656852 A1 DE 2656852A1 DE 19762656852 DE19762656852 DE 19762656852 DE 2656852 A DE2656852 A DE 2656852A DE 2656852 A1 DE2656852 A1 DE 2656852A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl ester
- nicotinamido
- anthranilic acid
- compounds
- acid
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000005011 4-aminoquinolines Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 28
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000012876 carrier material Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- HTKGKUISLUERQX-UHFFFAOYSA-N 2-[(7-chloroquinolin-4-yl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 HTKGKUISLUERQX-UHFFFAOYSA-N 0.000 claims description 3
- CDMFHWPEODSPGH-UHFFFAOYSA-N OC(=O)C1=CC=CC=C1NC(=O)OC(=O)NC1=CC=CC=C1C(O)=O Chemical compound OC(=O)C1=CC=CC=C1NC(=O)OC(=O)NC1=CC=CC=C1C(O)=O CDMFHWPEODSPGH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 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
- 230000036407 pain Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 claims 1
- QBYPVSPDWKEXRG-UHFFFAOYSA-N 2-[[7-(trifluoromethyl)quinolin-4-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(C(F)(F)F)=CC=C12 QBYPVSPDWKEXRG-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 230000000295 complement effect Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 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 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 5
- 229960001650 glafenine Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- -1 anthranilic acid ester Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 230000036269 ulceration 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
- LLRQVSZVVAKRJA-UHFFFAOYSA-N 4-chloro-7-(trifluoromethyl)quinoline Chemical compound ClC1=CC=NC2=CC(C(F)(F)F)=CC=C21 LLRQVSZVVAKRJA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 231100000111 LD50 Toxicity 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
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 239000002023 wood Substances 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 |
|---|---|
| DE2656852A1 true DE2656852A1 (de) | 1977-06-30 |
Family
ID=9164048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762656852 Withdrawn DE2656852A1 (de) | 1975-12-19 | 1976-12-15 | 4-amino-chinolinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
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 |
| CA1072961A (fr) | 1980-03-04 |
| FR2335223B1 (enExample) | 1978-12-22 |
| CH608804A5 (enExample) | 1979-01-31 |
| NL7613605A (nl) | 1977-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |