DE1620190B1 - 4-(2'-Carbo-alpha-glyceryloxyphenylamino)-8-chlorchinolin,seine Salze und ein Verfahren zu ihrer Herstellung - Google Patents
4-(2'-Carbo-alpha-glyceryloxyphenylamino)-8-chlorchinolin,seine Salze und ein Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1620190B1 DE1620190B1 DE19661620190D DE1620190DA DE1620190B1 DE 1620190 B1 DE1620190 B1 DE 1620190B1 DE 19661620190 D DE19661620190 D DE 19661620190D DE 1620190D A DE1620190D A DE 1620190DA DE 1620190 B1 DE1620190 B1 DE 1620190B1
- Authority
- DE
- Germany
- Prior art keywords
- chloroquinoline
- glyceryloxyphenylamino
- carbo
- salts
- preparation
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KWMVAQWWJJUEES-UHFFFAOYSA-N methyl 2-[(8-chloroquinolin-4-yl)amino]benzoate Chemical compound COC(=O)C1=C(C=CC=C1)NC1=CC=NC2=C(C=CC=C12)Cl KWMVAQWWJJUEES-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- BKZPHWHPYKDVFH-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-[(7-chloroquinolin-4-yl)amino]benzoate Chemical compound CN(CCOC(=O)C1=C(C=CC=C1)NC1=CC=NC2=CC(=CC=C12)Cl)C BKZPHWHPYKDVFH-UHFFFAOYSA-N 0.000 description 1
- SDPCOMBBZFETLG-UHFFFAOYSA-N 4,8-dichloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1Cl SDPCOMBBZFETLG-UHFFFAOYSA-N 0.000 description 1
- 150000005663 7-chloroquinolines Chemical class 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 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 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- 241000978776 Senegalia senegal Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000007684 eye toxicity Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000327 ocular toxicity Toxicity 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- -1 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR876199A FR1369967A (fr) | 1961-10-17 | 1961-10-17 | Nouveaux dérivés de la quinoléine et procédé de préparation |
| FR899417A FR90802E (fr) | 1961-10-17 | 1962-06-01 | Nouveaux dérivés de la quinoléine et procédé de préparation |
| FR11769A FR92111E (fr) | 1961-10-17 | 1965-04-02 | Nouveaux dérivés de la quinoléine et procédé de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620190B1 true DE1620190B1 (de) | 1972-05-25 |
Family
ID=27242041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620190D Pending DE1620190B1 (de) | 1961-10-17 | 1966-03-31 | 4-(2'-Carbo-alpha-glyceryloxyphenylamino)-8-chlorchinolin,seine Salze und ein Verfahren zu ihrer Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE678551A (enrdf_load_stackoverflow) |
| BR (2) | BR6678335D0 (enrdf_load_stackoverflow) |
| CH (1) | CH460006A (enrdf_load_stackoverflow) |
| DE (1) | DE1620190B1 (enrdf_load_stackoverflow) |
| DK (1) | DK112094B (enrdf_load_stackoverflow) |
| FR (2) | FR90802E (enrdf_load_stackoverflow) |
| LU (1) | LU50805A1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA726593B (en) * | 1971-10-19 | 1973-06-27 | Abbott Lab | Novel derivatives of 2,3-dihydroxypropyl-n-(7 or 8-chloro-4-quinolinyl)anthranilate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1173899B (de) * | 1962-02-16 | 1964-07-16 | Roussel Uclaf | Verfahren zur Herstellung des antiinflammatorisch und analgetisch wirksamen 4-[2'-(ª-Dimethylamino-aethoxycarbonyl)-phenylamino]-7-chlor-chinolins |
-
1962
- 1962-06-01 FR FR899417A patent/FR90802E/fr not_active Expired
-
1965
- 1965-04-02 FR FR11769A patent/FR92111E/fr not_active Expired
-
1966
- 1966-03-28 BE BE678551D patent/BE678551A/xx not_active IP Right Cessation
- 1966-03-28 DK DK158366AA patent/DK112094B/da unknown
- 1966-03-31 CH CH464266A patent/CH460006A/fr unknown
- 1966-03-31 DE DE19661620190D patent/DE1620190B1/de active Pending
- 1966-03-31 BR BR178335/66A patent/BR6678335D0/pt unknown
- 1966-03-31 LU LU50805A patent/LU50805A1/xx unknown
- 1966-03-31 BR BR178334/66A patent/BR6678334D0/pt unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1173899B (de) * | 1962-02-16 | 1964-07-16 | Roussel Uclaf | Verfahren zur Herstellung des antiinflammatorisch und analgetisch wirksamen 4-[2'-(ª-Dimethylamino-aethoxycarbonyl)-phenylamino]-7-chlor-chinolins |
Also Published As
| Publication number | Publication date |
|---|---|
| FR92111E (fr) | 1968-09-27 |
| BR6678334D0 (pt) | 1973-10-23 |
| DK112094B (da) | 1968-11-11 |
| CH460006A (fr) | 1968-07-31 |
| FR90802E (fr) | 1968-02-23 |
| LU50805A1 (enrdf_load_stackoverflow) | 1966-10-12 |
| BR6678335D0 (pt) | 1973-10-23 |
| BE678551A (enrdf_load_stackoverflow) | 1966-09-28 |
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