US2594418A - Salicylic acid salt of 8-(5'-isopropylaminoamylamino)-6-methoxyquinoline - Google Patents
Salicylic acid salt of 8-(5'-isopropylaminoamylamino)-6-methoxyquinoline Download PDFInfo
- Publication number
- US2594418A US2594418A US118997A US11899749A US2594418A US 2594418 A US2594418 A US 2594418A US 118997 A US118997 A US 118997A US 11899749 A US11899749 A US 11899749A US 2594418 A US2594418 A US 2594418A
- Authority
- US
- United States
- Prior art keywords
- isopropylaminoamylamino
- methoxyquinoline
- acid salt
- salicylic acid
- vol
- 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 - Lifetime
Links
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
- C07D215/40—Nitrogen atoms attached in position 8
Definitions
- antihistamine substances which concentrate especially in the respiratory epithelium andwhich had a prolonged duration so that a serum level could be established and maintained.
- the particular antihistamines which are the subject of the persent invention are amino-quinolines and in particular the monoknown compound 8-(5'-isopropylaminoamylamino) -6-methoxy-quinoline for 'a short period of time with a solution of a quantity in slight molar excess of salicyclic acid in ethanol.
- the reaction product was then concentrated to dryness and extracted with 3 portions of hot boiling (70-90 C.) petroleum ether.
- the hot petroleum ether solution was decanted and the residue dried. The residue was then suitably formed into 15 mg.
- Example I 4 gs. of 8-(5-isopropylaminoamylamino)-6- methoxyquinoline were boiled for 15 minutes salicylates of 6 methoxy 8 substituted quinolines.
- R is a poly methylene chain of from 2 to 6 carbon atoms and R1 is an alkyl radical of from 2 to 6 carbon atoms.
- An especially desirable compound was the mono-salicylate of 8-(5'- isopropylaminoamylamino) -6- methoxyquinoline. This compound was administered to a number of patients and it was found that plasma levels as high as .1 mg. per liter could be obtained on'daily doses as low as 60 mg. In addition the compound showed 90% retention on a daily dose in the tissue and body fluids with a high concentration in the respiratory tissue. It was found to have excellent results in various types of allergy and common cold and in cases of chronic sinusitis. Undesirable side efiects were not noticeable in substantially all cases.
- the salicylate salt was prepared by boiling the with a solution of 5 gs. of salicyclic acid in 20 cc. of ethanol, concentrated to dryness and extracted with 3 portions of hot (-90 C.) boiling petroleum ether. The hot petroleum ether solution was decanted and the residue showed the correct elementary values for the salicylate salt.
- a new compound consisting of the salicyclic acid salt of 8-(5-isopropylaminoamylamino)-6- methoxyquinoline.
- Wiselogle Survey of Antimalarial Drugs, 1941-1945" (J. W. Edwards; Ann Arbor, Mich., 1946), vol. I, pages 109-124; vol. II, part 2, page 1183.
- Huttrer Enzymologia, vol. XII, page 321 (1948).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Patented Apr. 29, 1952 UNITED STATES PATENT OFFICE SALICYLIC ACID SALT F 8- ('-ISOPR.OPYL- AMINOAMYLAMINO) 6 -METHOXYQUINO- LINE Charles F. Geschickter, Rock Creek Hills, and Martin I. Rubin, Silver Spring, Md., assignors to GeschickterFund for Medical Research, Inc., New York, N. Y., a corporation of New York No Drawing. Application September 30, 1949, Serial No. 118,997
1 Claim.
Where efiective, they afford symptomatic rather than permanent relief or cure. The same is true of desensitizing injections of protein substances which have the added disadvantage of requiring elaborate intradermal testing to determine the nature of the sensitizing agent or allergen.
In accordance with the present invention certain new antihistamine substances have been found which concentrate especially in the respiratory epithelium andwhich had a prolonged duration so that a serum level could be established and maintained. The particular antihistamines which are the subject of the persent invention are amino-quinolines and in particular the monoknown compound 8-(5'-isopropylaminoamylamino) -6-methoxy-quinoline for 'a short period of time with a solution of a quantity in slight molar excess of salicyclic acid in ethanol. The reaction product was then concentrated to dryness and extracted with 3 portions of hot boiling (70-90 C.) petroleum ether. The hot petroleum ether solution was decanted and the residue dried. The residue was then suitably formed into 15 mg.
capsules.
Example I 4 gs. of 8-(5-isopropylaminoamylamino)-6- methoxyquinoline were boiled for 15 minutes salicylates of 6 methoxy 8 substituted quinolines.
The particular salicylates involved are the monosalicylates of compounds represented byv the following formula:
wherein R is a poly methylene chain of from 2 to 6 carbon atoms and R1 is an alkyl radical of from 2 to 6 carbon atoms. An especially desirable compound was the mono-salicylate of 8-(5'- isopropylaminoamylamino) -6- methoxyquinoline. This compound was administered to a number of patients and it was found that plasma levels as high as .1 mg. per liter could be obtained on'daily doses as low as 60 mg. In addition the compound showed 90% retention on a daily dose in the tissue and body fluids with a high concentration in the respiratory tissue. It was found to have excellent results in various types of allergy and common cold and in cases of chronic sinusitis. Undesirable side efiects were not noticeable in substantially all cases.
The salicylate salt was prepared by boiling the with a solution of 5 gs. of salicyclic acid in 20 cc. of ethanol, concentrated to dryness and extracted with 3 portions of hot (-90 C.) boiling petroleum ether. The hot petroleum ether solution was decanted and the residue showed the correct elementary values for the salicylate salt.
It will be obvious to those skilled in the art that various changes may be made without departing from the spirit of the invention and therefore the invention is not limited to What is described in the specification but only as indicated in the appended claim.
What is claimed is:
A new compound consisting of the salicyclic acid salt of 8-(5-isopropylaminoamylamino)-6- methoxyquinoline.
CHARLES F. GESCHICKTER. MARTIN I. RUBIN.
REFERENCES CITED The following references are of record in the file of this patent:
Wiselogle: Survey of Antimalarial Drugs, 1941-1945" (J. W. Edwards; Ann Arbor, Mich., 1946), vol. I, pages 109-124; vol. II, part 2, page 1183.
Fischel: Proc. Soc. Exptl. Biol. Med., vol. 66, pp. 537-541 (1947).
Huttrer: Enzymologia, vol. XII, page 321 (1948).
Beiler: J. Am. Pharm. Assoc. (Sci. Ed.), vol. 37, pp. 315-317 (June 1949).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US118997A US2594418A (en) | 1949-09-30 | 1949-09-30 | Salicylic acid salt of 8-(5'-isopropylaminoamylamino)-6-methoxyquinoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US118997A US2594418A (en) | 1949-09-30 | 1949-09-30 | Salicylic acid salt of 8-(5'-isopropylaminoamylamino)-6-methoxyquinoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2594418A true US2594418A (en) | 1952-04-29 |
Family
ID=22382023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US118997A Expired - Lifetime US2594418A (en) | 1949-09-30 | 1949-09-30 | Salicylic acid salt of 8-(5'-isopropylaminoamylamino)-6-methoxyquinoline |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2594418A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3069423A (en) * | 1959-06-26 | 1962-12-18 | Charles H Grogan | Therapeutic salts |
-
1949
- 1949-09-30 US US118997A patent/US2594418A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3069423A (en) * | 1959-06-26 | 1962-12-18 | Charles H Grogan | Therapeutic salts |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| White | Drug treatment and prevention of malaria | |
| US9340491B2 (en) | Nitrile derivatives and their pharmaceutical use and compositions | |
| EA001929B1 (en) | Method of treating a disease in a mammal and zwitterionic composition | |
| McKee et al. | Therapeutic effect of sulfathiazole and sulfapyridine | |
| US2594418A (en) | Salicylic acid salt of 8-(5'-isopropylaminoamylamino)-6-methoxyquinoline | |
| Winstanley et al. | Currently important antimalarial drugs | |
| Sabin et al. | The therapeutic effectiveness of a practically nontoxic new compound (calcium aurothiomalate) in experimental, proliferative, chronic arthritis of mice | |
| US4468393A (en) | Treatment of arthritis | |
| US2594419A (en) | Di-salicylate of 7-chloro-4-(4'-diethylamino-1'-methylbutylamino) quinoline | |
| KR890701526A (en) | Keratosis Drug | |
| Cormia et al. | Experimental aspects of penicillin sensitization, with special reference to conjoint sensitization to superficial fungous disease | |
| Phear et al. | Trial a New Monoamine Oxidase Inhibitor in Angina Pectoris | |
| Goble | Chemotherapeutic activity of certain 8-aminoquinolines, particularly pentaquine, in experimental Chagas' disease | |
| AU718946B2 (en) | Antimalarial organometallic iron complexes | |
| RU2646475C2 (en) | Treatment of type i and ii diabetes | |
| KULCHAR et al. | Bismuth Hepatitis: A Survey of One Hundred and Twenty-One Cases | |
| Selzer, G., Sacks, M. & Van den Ende | Adaptation and multiplication rate of the MEF1 strain of poliomyelitis virus in new-born mice | |
| US2214527A (en) | Alkali metal salts of the acetaldehyde bisulphite compound of sulphanilamide | |
| Bliss et al. | Effect of Sulfapyridine, Sulfathiazole and Sulfamethylthiazole upon Severe Staphylococcal Infection in Mice. | |
| US2145799A (en) | Therapeutic preparation | |
| Hunsicker | The Pharmacology of the Antimalarials: A Rational Approach to the Therapy of Resistant Falciparum Malaria | |
| CA3005120A1 (en) | New molecules from seaweeds with anti-cancer activity | |
| Chopra et al. | Studies on the Action of Antimalarial Remedies on Monkey Malaria: The Relationship between the Concentration of Atebrin in the Circulating Blood and Parasite Count | |
| RU2000119C1 (en) | Antiallergic preparation | |
| KR880000383A (en) | 1,7-substituted heptin-2-one and its use in the treatment of neurological bladder disease |