US2719848A - 4-(dimethylaminoethylamino)-6-methoxy quinoline and salts thereof - Google Patents

4-(dimethylaminoethylamino)-6-methoxy quinoline and salts thereof Download PDF

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US2719848A
US2719848A US513906A US51390655A US2719848A US 2719848 A US2719848 A US 2719848A US 513906 A US513906 A US 513906A US 51390655 A US51390655 A US 51390655A US 2719848 A US2719848 A US 2719848A
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dimethylaminoethylamino
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quinoline
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Charles F Geschickter
Leonard M Rice
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    • 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • 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
    • C07D215/20—Oxygen atoms
    • 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
    • C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4

Definitions

  • the present invention relates to new quinoline derivatives, to non-toxic salts thereof, and to methods of making these compounds. More particularly our invention relates to a 4-dimethylaminoethylamino-6-methoxy quinoline and to non-toxic salts thereof which We have found to be effective remedies for asthma and related allergic disorders.
  • Non-toxic salts of the base have the same bronchial dilator and antihistaminic action and have other desirable properties which make them easier or more convenient to administer and improve the safety factor for administration. All of the non-toxic salts have the bronchial dilator and antihistaminic action but due to their other properties, the salts fall into different groups.
  • the non-toxic inorganic salts such as the chloride, bromide, iodide, phosphate and sulphate are very soluble in water but they are acidic and painful when administered by injection.
  • Complex organic salts such as the salts of phthalamic, quininic, nicotinic, and ascorbic acids and theophylline are soluble, substantially neutral, have low toxicity and because of their relatively high molecular weights have a relatively high safety factor.
  • the non-toxic simple organic salts such as the acetate, tartarate, myristate and stearate have properties which are in general between those of the inorganic salts and those of the complex organic salts.
  • the simple organic salts are generally less acidic than the inorganic salts and, as the molecular weight increases, they become less soluble in water and more soluble in oils.
  • An important object of the present invention is to provide as a novel composition of matter, 4-dimethylaminoethylamino, 6-methoxyquinoline and non-toxic salts thereof.
  • Another object is to provide quinoline compounds which are a remedy for asthma and related allergic disorders.
  • Another object is to provide water-soluble, non-toxic quinoline compounds.
  • Another object is to provide non-toxic quinoline compounds which are substantially neutral.
  • Another object is to provide non-toxic quinoline compounds which are substantially stable and moisture proof.
  • Another object is to provide methods of making 4-dimethylaminoethylamino-6-methoxy quinoline and nontoxic salts thereof.
  • the free base form of the compounds of the present invention is 4-dimethylaminoethylamino-6-methoxyquinoline which has the followingformula:
  • This new quinoline derivative and its non-toxic salts have been tested in over 500 patients and have been found to be effective in the treatment of asthma and related allergic disorders.
  • the compounds have been found to have anticholine and antihistaminic effects and to be concentrated in the lungs and respiratory tissues. Their characteristics include long retention in the body and a cumulative effect so that when used in the treatment of asthma, relief is prolonged and dosage may be reduced as the treatment progresses.
  • Another important property of the new compound and its salts is low toxicity and absence of undesirable side effects.
  • the free base may be prepared as follows:.
  • V.-1;-chl0r0-6-melhoxyquinoline The 4-hydroxy-6-methoxy quinoline was refluxed with phosphorus oxychloride for 4 hours. After cooling the reaction mixture was hydrolyzed by pouring onto cracked ice and the resulting aqueous suspension made alkaline with sodium hydroxide. The insoluble product was filtered, washed with water and dried. Melting point 80-81 deg.
  • the reaction mixture was transferred with the aid of a little dilute hydrochloric acid to 500 ml. of water.
  • the solution was extracted with a little ether and next was neutralized with sodium hydroxide until strongly basic.
  • the basic solution was extracted twice with ether and the extract was dried over magnesium sulfate and Theoretical 68. 54 7. 8 17.13 Found 68. 42 7. 65 17. 32
  • the free base may be administered orally inan alcohol or oil solution. It is absorbed. into the system and ultimately concentrates in the lungs and bronchial tissues. In this form, absorption is slow but sincethe effects are cumulative, the free base isefiective in relieving asthma.
  • non-toxic organic and inorganic salts are as elfective as: the base compound and generally have the additional desirable property of being more soluble, and hence, more convenient to administer;
  • Non-toxic inorganic salts include the chloride, bromide, iodide, sulphate and phosphate and non-toxic organic salts include the acetate, citrate, tartarate, stearate, myristate, phythalate, naphtholate,succinate andzsalts of theophyllin, phthalamic acid, quininic acid, nicotinic acid, ascorbic acid and the like.
  • the appropriate acid in alcohol solution is added to an alcohol solution. of the base.
  • the salt is then precipitated with ether and recrystallized.v
  • the hydrochloride for example is a yellowish hydroscopic crystalline solid with an indefinite melting point.. It is. soluble in alcohol and very soluble in water.
  • the inorganic salts have a high pH value and are painful when administered by injection. Neutralizing the pH value with a base may precipitate the free base. These salts are also hydroscopic so that handling and storage presents a problem-
  • the simple organic salts such as the acetate, stearate, and myristate are prepared in a similar manner. Analcohol solution of the chosen organic acid is added to an alcohol solution of the base in molar proportions. The alcohol is then distilled oif at reduced pressure.
  • the acetate is a. bull colored crystalline powder very soluble in water and soluble in. alcohol, benzene, ether andoily vehicles. Ithas an. indefinite boilingpoint.
  • T he. stearate is a yellowish oilinsoluble in water but soluble. in common organic solvents.
  • the myristate is an oil and issoluble in sesame: oil. and common organic solvents but not very soluble inwater.
  • Some of these simple organic salts are very stable and moisture resistant. Because of this property they may be manufactured, shipped and stored. in bulk or tablet form without damageor deterioration.
  • the more complex organic salts such asthe salts of theophylline, quininic acid, phthalamic acid, nicotinic acid and ascorbic acid are soluble, substantially neutral and often. havev a. lower toxicity than the basecompound. These salting radicals also have some bronchial dilator action so that these salts are more efiective and easier to administer'than the base compound.
  • organic salts Because of. their relatively high molecular- Weights', the more complex: organic salts also have agreater factor of safety.
  • the salting radical has substantially no toxicity: and variations in dosage will have a relatively minor'effect on the amount of basev compound administered.
  • N,N-diethyl sis-A tetrahydrophthalamate salt of 6-meth0xy-4 (dimethylaminoethylamino) quinoline 6-meth0xy-4 (dimethylaminoethylamino) quinoline.
  • the nicotinic acid salt was prepared in substantiallythe' same manner.
  • the saltsare giverrin 50 mg. tablets or capsules once or twice" daily.
  • the salt may be dissolved in'wate'r, benzyl alcohol and dioctyl hexahydrophthalic estersolte tion', ora suitable oil such as'peanutoil, sesame oilor'the is 100 to 120 mg. per cc. and dosages of 36 cc. daily have been found effective and, since the results are cumulative, administration can be reduced to every other day or even weekly as indicated by the patients response to the treatment. Since the 4-(dimethylaminoethylamino-dmethoxy quinoline is the primary active portion of the compound, dosages and concentrations of the base compound and other salts are varied so that substantially the same amount of the active portion is given.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

United States Patent 4-(DIMETHYLAMINOE'I'HYLAMINO)-6-METHOXY QUlNOLlNE AND SALTS THEREOF Charles F. Geschickter, Kensington, and Leonard M. Rice, Baltimore, Md.
No Drawing. Application June 7, 1955,
Serial No. 513,906
3 Claims. (Cl. 260286) The present invention relates to new quinoline derivatives, to non-toxic salts thereof, and to methods of making these compounds. More particularly our invention relates to a 4-dimethylaminoethylamino-6-methoxy quinoline and to non-toxic salts thereof which We have found to be effective remedies for asthma and related allergic disorders.
This application is a continuation-in-part of application Serial No. 378,420 filed September 3, 1953, which is a continuation-in-part of application Serial No. 251,980 filed October 18, 1951. It is also a continuation of applications Serial No. 378,422, filed September 3, 1953, and Serial No. 446,946 filed July 30, 1954, and a continuation-in-part of Serial No. 379,781, filed December 11, 1953.
We have found that 4-dimethylaminoethylamino-6- methoxy quinoline has bronchial dilator and antihistaminic action and that it tends to concentrate in the respiratory tissues. For this reason, the compound is effective in the treatment of asthma. While this base compound is insoluble in water it may be administered orally in oil solutions and we have found that it has a cumulative effect and is characterized by long retention in the body.
Non-toxic salts of the base have the same bronchial dilator and antihistaminic action and have other desirable properties which make them easier or more convenient to administer and improve the safety factor for administration. All of the non-toxic salts have the bronchial dilator and antihistaminic action but due to their other properties, the salts fall into different groups.
The non-toxic inorganic salts such as the chloride, bromide, iodide, phosphate and sulphate are very soluble in water but they are acidic and painful when administered by injection. Complex organic salts such as the salts of phthalamic, quininic, nicotinic, and ascorbic acids and theophylline are soluble, substantially neutral, have low toxicity and because of their relatively high molecular weights have a relatively high safety factor. The non-toxic simple organic salts such as the acetate, tartarate, myristate and stearate have properties which are in general between those of the inorganic salts and those of the complex organic salts. The simple organic salts are generally less acidic than the inorganic salts and, as the molecular weight increases, they become less soluble in water and more soluble in oils.
An important object of the present invention is to provide as a novel composition of matter, 4-dimethylaminoethylamino, 6-methoxyquinoline and non-toxic salts thereof.
Another object is to provide quinoline compounds which are a remedy for asthma and related allergic disorders.
Another object is to provide water-soluble, non-toxic quinoline compounds.
Another object is to provide non-toxic quinoline compounds which are substantially neutral.
Another object is to provide non-toxic quinoline compounds which are substantially stable and moisture proof.
Another object is to provide methods of making 4-dimethylaminoethylamino-6-methoxy quinoline and nontoxic salts thereof.
The free base form of the compounds of the present invention is 4-dimethylaminoethylamino-6-methoxyquinoline which has the followingformula:
This new quinoline derivative and its non-toxic salts have been tested in over 500 patients and have been found to be effective in the treatment of asthma and related allergic disorders. The compounds have been found to have anticholine and antihistaminic effects and to be concentrated in the lungs and respiratory tissues. Their characteristics include long retention in the body and a cumulative effect so that when used in the treatment of asthma, relief is prolonged and dosage may be reduced as the treatment progresses. Another important property of the new compound and its salts is low toxicity and absence of undesirable side effects.
The free base may be prepared as follows:.
I .Alpha-carbethoxy-B-( p-anisidino) -acrylate A mixture of 0.4 mole of p-anisidine and 0.4 mole of. ethoxymethylene malonic ester was heated at deg. until no more bubbles of alcohol could be detected coming from the mixture.
II.-3 carbethoxy-4-hydroxy-6-methoxyquinoline III.-3-carboxy-4-hydroxy-6-methoxyquinoline The ester group was removed by boiling with 18% hydrochloric acid for one hour. The solution was filtered and the desired free acid crystallized as the filtrate cooled. Melting point 271 with gas evolution.
I V.4-hydr0xy-6-methoxyquinoline The acid from III above was heated in a Woods metal bath at 275 deg. until the evolution of carbon dioxide ceased. The product was taken up in hot water (20 ml. per gram) and treated with decolorizing charcoal. This hot mixture was filtered and the product crystallized from the filtrate in the form of needles. Melting point 240243 deg. The product in solution gives a pink or red color with a drop of ferric chloride solution.
V.-1;-chl0r0-6-melhoxyquinoline The 4-hydroxy-6-methoxy quinoline was refluxed with phosphorus oxychloride for 4 hours. After cooling the reaction mixture was hydrolyzed by pouring onto cracked ice and the resulting aqueous suspension made alkaline with sodium hydroxide. The insoluble product was filtered, washed with water and dried. Melting point 80-81 deg.
VI.4-(B-dimethylaminoethyl) -6-meth0xyquin0line 4-chloro-6-methoxy quinoline (0.205 mole) and B-dimethylaminoethylamine (0.200 mole) were heated slowly in a bomb tube with a crystal of K. I. to to deg. for 4 hours. The reaction mixture was transferred with the aid of a little dilute hydrochloric acid to 500 ml. of water. The solution was extracted with a little ether and next was neutralized with sodium hydroxide until strongly basic. The basic solution was extracted twice with ether and the extract was dried over magnesium sulfate and Theoretical 68. 54 7. 8 17.13 Found 68. 42 7. 65 17. 32
The free base may be administered orally inan alcohol or oil solution. It is absorbed. into the system and ultimately concentrates in the lungs and bronchial tissues. In this form, absorption is slow but sincethe effects are cumulative, the free base isefiective in relieving asthma.
The non-toxic organic and inorganic salts are as elfective as: the base compound and generally have the additional desirable property of being more soluble, and hence, more convenient to administer; Non-toxic inorganic salts include the chloride, bromide, iodide, sulphate and phosphate and non-toxic organic salts include the acetate, citrate, tartarate, stearate, myristate, phythalate, naphtholate,succinate andzsalts of theophyllin, phthalamic acid, quininic acid, nicotinic acid, ascorbic acid and the like.
To prepare the inorganic salts, the appropriate acid in alcohol solution is added to an alcohol solution. of the base. The salt is then precipitated with ether and recrystallized.v The hydrochloride for example is a yellowish hydroscopic crystalline solid with an indefinite melting point.. It is. soluble in alcohol and very soluble in water.
The inorganic salts have a high pH value and are painful when administered by injection. Neutralizing the pH value with a base may precipitate the free base. These salts are also hydroscopic so that handling and storage presents a problem- The simple organic salts such as the acetate, stearate, and myristate are prepared in a similar manner. Analcohol solution of the chosen organic acid is added to an alcohol solution of the base in molar proportions. The alcohol is then distilled oif at reduced pressure.
The acetate is a. bull colored crystalline powder very soluble in water and soluble in. alcohol, benzene, ether andoily vehicles. Ithas an. indefinite boilingpoint. T he. stearate is a yellowish oilinsoluble in water but soluble. in common organic solvents. The myristate is an oil and issoluble in sesame: oil. and common organic solvents but not very soluble inwater.
Some of these simple organic salts are very stable and moisture resistant. Because of this property they may be manufactured, shipped and stored. in bulk or tablet form without damageor deterioration.
The more complex organic salts such asthe salts of theophylline, quininic acid, phthalamic acid, nicotinic acid and ascorbic acid are soluble, substantially neutral and often. havev a. lower toxicity than the basecompound. These salting radicals also have some bronchial dilator action so that these salts are more efiective and easier to administer'than the base compound.
Because of. their relatively high molecular- Weights', the more complex: organic salts also have agreater factor of safety. The salting radical has substantially no toxicity: and variations in dosage will have a relatively minor'effect on the amount of basev compound administered.
Preparation of" thetheophylline salt of 6 meth0xy-4 dimethylaminoethylamino quinoline A mixture of 29.6 grams of theophylline' and 2415 like and injectedintramuscularly; A convenient solution grams of 6 methoxy 4 (dimethylaminoethyl amino quinoline are dissolved in 200 ml. of dry acetone. The solution after filtering is transferred to a 3-liter container and the acetone is removed under reduced pressure. After most of the acetone has been removed, the last traces are removed under high vacuum. The residue is covered, redissolved in alcohol, from which it is obtained as a crystalline salt.
4-(dimezhylaminoethylamino)-6-methoxyquinoline,salt of quininic acid A mixture of 2.45 gr. of 4-dimethylaminoethylamino-6- methoxy quinoline and 4.06 gm. of quininic acid is heated at reflux with 35 cc. of dry acetone. Methanol (anhy drous) is added to the boiling solution until the material just dissolves. The solution is boiled an additional several minutes and filtered. The solution is allowed to come to room temperature and diluted to permanent turibidity with anhydrous ether. Upon standing in the ice box for several hours there is obtained 5 gm; of the salt (77%)- in the form of needles which after filtration and drying melts at 162-163; The salt dissolves inwater giving analmost neutral solution.
The N,N-diethyl sis-A tetrahydrophthalamate salt of 6-meth0xy-4 (dimethylaminoethylamino) quinoline.
A mixture of 45.5 grams (0.2 mol) of N,N-diethyl cis-A tetrahydrophthalarnic acid and 25.5 grams (-0.1 mol.) of 6-methoxy-4-(-dimethylaminoethylamino=) quin oline are dissolved in 200 mli (a convenient quantity) of 'ry acetone. The solution, after filtering is-transferred to a container of suitable size and the acetone removed under reduced pressure. After most ofthe acetone has been removed the last traces are removed under high vacuum' (less than 0.1 mm.). The residue is loosely powdered, transferred to amortar and finely powdered. The product is an almost white, free flowing hygroscopic powder.
In the process illustrated in the foregoing example, the following amic acids may be used in place of N,N-dietliyl' cis-M-tetrahydrophthalamic acid to obtain the" corresponding salts:
N,N-dimethyl phthalamic N,N-diethyl phthalamic N ,N-dimethyl hexahydrophthalamic N,N diethyl hexahyd rophthalamic N,N-dimethyl cis-n -te trahydrophthamic Ascorbic acid salt of 4-(dimethylaminoethylamino) 6- methoxy quinoline' To prepare this salt, 7.04 grams (O'.O4mole') of ascorbic acid dissolved in ml. of methanol was placed in a 500 ml. flask fitted with a condenser. To this was-added 4.9 grams (0.08 mole) of 4-(dimethylaminoethylamincr)= 6-methoxy quin'oline dissolved in 25' ml. of methanol.
The mixture was refluxed for onehour and the methanol distilled off in a water bath. The product was obtained as a yellow crystalline powder, very soluble and giving a neutral solution in Water.
The nicotinic acid salt was prepared in substantiallythe' same manner.
The complex organic salts such asthe phthal'amate,
ascorbate and the like may be administered orally or'by iniection. For oral administration, the saltsare giverrin 50 mg. tablets or capsules once or twice" daily. For par== enteral administration, the salt may be dissolved in'wate'r, benzyl alcohol and dioctyl hexahydrophthalic estersolte tion', ora suitable oil such as'peanutoil, sesame oilor'the is 100 to 120 mg. per cc. and dosages of 36 cc. daily have been found effective and, since the results are cumulative, administration can be reduced to every other day or even weekly as indicated by the patients response to the treatment. Since the 4-(dimethylaminoethylamino-dmethoxy quinoline is the primary active portion of the compound, dosages and concentrations of the base compound and other salts are varied so that substantially the same amount of the active portion is given.
From the foregoing it will be apparent that we are able to accomplish the objects of our invention and provide novel compounds which have valuable therapeutic properties and a process for producing such compounds. Various modifications can of course be made without departing from the spirit of the invention or the scope of the appended claims. The term acid addition salts used in the claims refers to salts of the type formed by treating a base with an acid.
We claim:
1. As a new composition of matter the ascorbic acid No references cited.

Claims (1)

  1. 3. A NOVEL COMPOSITION OF MATTER CONSISTING OF A COMPOUND SELECTED FROM THE CLASS CONSISTING OF 4-(DIMETHYLAMINOETHYLAMINO)-6-METHOXY QUINOLINE AND NON-TOXIC, WATER SOLUBLE ACID ADDITION SALTS THEREOF.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2947664A (en) * 1955-07-11 1960-08-02 Geschickter Fund Med Res Salts of 7-chloro-4-(4-diethylamino-1-methylbutylamino) quinoline
US3069424A (en) * 1960-07-08 1962-12-18 Geschickter Fund Med Res Thiodisalicylate salt
US4035368A (en) * 1975-04-02 1977-07-12 Riker Laboratories, Inc. Substituted 3-(1H-tetrazol-5-yl)-quinoline compounds
US4808598A (en) * 1986-06-30 1989-02-28 The United States Of America As Represented By The Secretary Of The Army Method for inducing protection in an animal against cyanide poisoning using 8-aminoquinolines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2947664A (en) * 1955-07-11 1960-08-02 Geschickter Fund Med Res Salts of 7-chloro-4-(4-diethylamino-1-methylbutylamino) quinoline
US3069424A (en) * 1960-07-08 1962-12-18 Geschickter Fund Med Res Thiodisalicylate salt
US4035368A (en) * 1975-04-02 1977-07-12 Riker Laboratories, Inc. Substituted 3-(1H-tetrazol-5-yl)-quinoline compounds
US4808598A (en) * 1986-06-30 1989-02-28 The United States Of America As Represented By The Secretary Of The Army Method for inducing protection in an animal against cyanide poisoning using 8-aminoquinolines

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