US3074937A - Diphenylcarbonylmethinylhydrazidoalkyl quaternary salts - Google Patents

Diphenylcarbonylmethinylhydrazidoalkyl quaternary salts Download PDF

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US3074937A
US3074937A US71166A US7116660A US3074937A US 3074937 A US3074937 A US 3074937A US 71166 A US71166 A US 71166A US 7116660 A US7116660 A US 7116660A US 3074937 A US3074937 A US 3074937A
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Cavallini Guido
Massarani Elena
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Francesco Vismara SpA
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones

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  • This invention relates to a novel series of soluble chemotherapeutic agents having substantial antiviral activity. More specifically these compounds are diphenylcarbonylmethinylhydrazidoalkyl quaternary salts.
  • novel compounds of this invention have been found to have antiviral activity, either prophylactic or curative, against such viral infections as distemper virus, hepatitis virus (MHV neurotropic virus (CLM), Coxsackie virus, Echo virus, hemadsorption virus, adenovirus, Newcastle disease virus, herpes simplex and, particularly, influenza virus (A or PR).
  • HMV neurotropic virus CLM
  • Coxsackie virus Echo virus
  • hemadsorption virus hemadsorption virus
  • adenovirus adenovirus
  • Newcastle disease virus herpes simplex
  • influenza virus A or PR
  • the compounds are also very Water soluble thereby lending themselves readily to various routes of administration particularly subcutaneous routes or topical applications, for instance under the form of collyrium.
  • X is a pharmaceutically acceptable anion such as chloride, iodide or bromide
  • Y is a quaternary ammonium radical of the group consisting of pyridinium trialkylamrnonium (-1%-8.lkylg) alkylpiperidinium alkyl alkylpyrrolidinium tiIryl 3,014,937 Patented Jan.
  • alkyl alltylmorpholinium alkyl-N-alkylpiperazinium alkyl and dialltyl-Nalkylpiperazinium alkyl alkyl Preferred and advantageous compounds are those according to the following formulas in which A is oxygen, sulfur or a single bond and Y is trimethylammonium, p'yridinium' or morpholinium and X .is as described above.
  • the compounds of this invention are prepared by condensing a diphenylyl mono or his glyoxal derivative with an alkanohydrazide ammonium halide having the following structure:
  • NH NHCOaIkyIYX (v) in which X and Y are as defined above for Formulas I and II.
  • the starting material glyoxalcan also be used in the form of an addition compound such as a hydrate, alcoholate for instance ethylate or'methylate or a bisulfite addition product. These glyoxal starting materials are all described in copending applications. An excess of the hydrazide of Formula V is'usually employed.
  • solvent is any unreactive organic solvent in which the reactants are mutually soluble.
  • the lower alcohols preferably, methanol, ethanol or isopropanol have been found to be very useful.
  • a condensing acid such as acetic acid is advantageously present.
  • Anhydrous conditions are particularly desirable. from 30 minutes to about three hours usually suflices for relatively complete reaction.
  • the products are isolated by cooling or by evaporation and trituration of the residue with ethyl ether.
  • the desired quaternary products thereupon crystallize but because of their chemical and physical nature melting points cannot be obtained.
  • alkyl is used herein to define straight or branched saturated hydrocarbon residues of from 1 to 3 carbon atoms inclusive. Alkoxy groups are similarly comprised of 1 to 3 carbon atoms.
  • reactive halide defines chloride, bromide or iodide anions. Of course other conventional nontoxic, pharmaceutically acceptable anions can be substituted therefor.
  • Other modifications in the structures outlined are obvious to those skilled in the art such as other substituents in the henzene or heterocyclic portions of the chemical structures or using larger alkyl moieties however the essential features of the compounds of this invention are described hereabove and the methods of preparing representative compounds of this invention are described hereafter.
  • Example 1 A mixture of 2.26 g. of 4-phenoxyphenylglyoxal, 1.97 g. of acethydrazide pyridinium chloride, 5 ml.- of glacial acetic acid and 25 ml. of absolute ethanol is heated at reflux for 30 minutes. The mixture is cooled and evaporated. "The residue is triturated with anhydrous ethyl ether to obtain a white crystalline product,
  • Example 2 A mixture of 2.2 g. of 4-glyoxylyldiphenylmethane hydrate, 2.45 g. of acethydrazide pyridinium chloride, 5 ml. of glacial acetic acid and 25 m1. of absolute methanol are heated at reflux for 3 hours. Cooling separates the desired product, [(4-benzylphenylcarbonyl)methinylhydrazidomethyl] pyridinium chloride.
  • Example 3 A mixture of 1 g. of diphenylethane-4-glyoxal, 1 g. of acethydrazide pyridinium chloride, 2.5 ml. of acetic acid and 15 ml. of ethanol is heated at reflux for 3"hours,
  • Example 7 yl-4,4 bis(carbonylmethinylhydrazidomethylpyridinium cooled and concentrated. The residue is triturated with ether to give [(4-phenethylphenylcarbonyl)methinylhydrazidomethyl]pyridinium chloride.
  • Example 4 A mixture of 2.98 g. of 4,4-bisglyoxylyldiphenylethane, 5.4 g. of acethydrazide pyridinium bromide, 5 ml. of acetic acid and 25 ml. of methanol is heated at reflux for 3 hours. Cooling gives biphenylethane-4,4'-bis(carbonylmethinylhydrazidomethylpyridinium bromide).
  • Example 5 A mixture of 3.18 g. of 4,4-bisglyoxylyldiphenylether,
  • Example 6 A mixture of 2.56 g. of diphenylyl-4-glyoxal ethylate, 3 g. of acethydrazide pyridinium chloride, 5 ml. of acetic acid and 25 ml. of ethanol is heated at reflux for 30 minutes, then cooled. The mixture is evaporated to dry ness in vacuo to give, upon tr'ituration with ether, [(4-bichloride)
  • Example 8 A mixture of 2.46 g. of biphenyl-4-glyoxal hydrate, 2.9 g. of acethydrazide methylmorpholinium iodide, 5 ml.
  • Example 9 A mixture of 2.3 g. of 4-phenylthiophenylglyoxal, 2.1 g. of acethydrazide trimethylammonium chloride, 7 ml. of acetic acid and 30 ml. of ethanol is heated at reflux for 4 hours, then worked up as above to give [(4-phenyl- 'thiophenylcarbonyl)methinylhydrazidomethyl] trimethylammonium chloride.
  • Example 10 A mixture of 2.4 g. of 4,4'-bis-glyoxylylstilbene hydrate, 5.1 g. of acethydrazide triethylammonium bromide, 5 ml. of acetic acid and 40 ml. of ethanol is reacted and worked up as in Example 3 to give stilbene-4,4-biscarbonylmethinylhydrazidomethyltriethylammonium bromide).
  • Example 11 A mixture of 3.3 g. of 4,4'-bisglyoxylyldiphenylsulfoxide ethylate, 5.8 g. of a-ethylacethydrazide methylpiperidinium bromide, prepared by quaternizing the hydrazide of Petrie and Horsley (US. Pat. No. 2,834,781), 10 ml. of acetic acid and 50 ml. of isopropanol is heated at reflux for 5 hours. Cooling, evaporation and trituration with ether gives the desired diphenylsulfoxide-4,4- bis(carbonylmethinylhydrazidoisopropyl methylpiperidinium bromide).
  • Example 12 A mixture of 1.5 g. of 2-phenoxyphenylglyoxal hydrate, 1.8 g. of acethydrazide trimethylammonium chloride, 5 ml. of acetic acid and 25 ml. of ethanol is heated at reflux for 2 hours and worked up as in Example 1 to give [(2-phenoxyphenylcarbonyl)methinylhydrazidomethyl] trimethylammonium chloride.
  • Example 13 A mixture of 1.2 g. of 4-phenylsulfonylphenylglyoxal, l g. of propionylhydrazide methylpyrrolidinium chloride, prepared by quaternizing the hydrazide of Petrie, 5 ml.. of acetic acid and 25 ml. of methanol is heated at reflux for several hours. Working up as described above gives [(4-phenyl-sulfonylphenylcarbonyl)methinylhydra-- zidoethyl] methylpyrrolidinium chloride.
  • Example 14 A mixture of 2.5 g. of biphenyl-4-glyoxal, 2.8 g. of acethydrazide N-methylpiperazinium dimethochloride, prepared as in Petrie, 10 ml. of acetic acid and 50 ml. of ethanol is heated at reflux for 4 hours, cooled and evaporated. Trituration with ether gives the desired diquaternary salt.
  • Example 15 A mixture of 2.7 g. of 4-phenoxyphenylglyoxal, 2.5 g. of acethydrazide methyl-N-methylpiperazinium chloride,
  • Example 16 A mixture of 2.8 g. of 4'-methoxybiphenylyl-4-glyoxal, 2.5 g. of acethydrazide pyridinium chloride, m1. of acetic acid and 75 ml. of methanol is heated at reflux for 30 minutes and worked up as in Example 1 to give [(4 methoxy 4 biphenylylcarbonyl)methinylhydrazidomethyl] pyridini'um chloride.
  • Example 17 A mixture of 1.5 g. of 3'-chloro-4'-1nethoxybiphenylyl- 4-glyoxal ethylate, 1.8 g. of acethydrazide trimethylammonium bromide and 100 ml. of isopropanol is heated at reflux for 6 hours. Working up as described above gives (3'-chloro-4'-methoxy-4-biphenyly1carbonyl methinylhydrazidomethyl] trimethylammonium bromide.
  • Example 18 Repeating Example 15 but using 1.2 g. of 4'-fiuoro biphenylyl-4-glyoxal gives the 4'-fluoro analogue; using 1.4 g. of the 4'-bromobiphenylyl-4-glyoxa1 gives the 4- bromo analogue; using 1.1 g. of the 4'-methylbipheny1-4- glyoxal gives the 4'-methyl quaternary.
  • Example 1 9 A mixture of 0.9 g. of 4-hydroxybiphenylyl-4-glyoxal hydrate, 1 g. of acethydr-azide pyridinium chloride, 5 ml. of acetic acid and 20 ml. of ethanol is heated at reflux for 1 hour to give the desired 4'-hydroxy-pyridiniurn chloride. Substituting the 4-n-propoxyglyoxal gives the corresponding 4-n-propoxy-pyridini1nn chloride.
  • Example 20 A mixture of 1.1 g. of 3.3'-bisglyoxylylbiphenyl is reacted With 2.2 g. of acethydrazide pyridinium chloride as described in Example 7 to give the 3,3-is0mer.
  • alkyl is of from 1 to 3 carbon atoms
  • X is a reactive halide
  • Y is a quaternary ammonium radical selected from the group consisting of pyridinium, trialkylammonium, alkylpiperidinium, alkylpyrrolidinium, alkylmorphollnium, alkyl N alkylpiperazinium and dialkyl-N-alkylpiperazinium, each of said alkyi moieties is of from 1 to 3 carbon atoms
  • A represents a member selected from the group consisting of oxygen, sulfur, sulfonyl, sulfinyl, methylene, ethylene, vinylene and a direct link
  • R is a member selected from the group consisting of hydrogen, allroxy of from 1 to 3 carbon atoms, methyl, chloro and hydroxy
  • R is a member selected from the group consisting of hydrogen and chloro.

Description

United States Patent F DIPHENYLCARBONYLMETHINYLHYDRAZIDO- ALKYL QUATERNARY SALTS Guido Cavallini and Elena Massarani, Milan, Italy, assignors to Francesco Vismara S;p.A., Casatenovo, Como,
No Drawing. Filed Nov. 23, 1960, Ser. No. 71,166
Claims priority, application Italy Aug. 27, 1960 7 Claims. (Cl. 260-240) This invention relates to a novel series of soluble chemotherapeutic agents having substantial antiviral activity. More specifically these compounds are diphenylcarbonylmethinylhydrazidoalkyl quaternary salts.
The novel compounds of this invention have been found to have antiviral activity, either prophylactic or curative, against such viral infections as distemper virus, hepatitis virus (MHV neurotropic virus (CLM), Coxsackie virus, Echo virus, hemadsorption virus, adenovirus, Newcastle disease virus, herpes simplex and, particularly, influenza virus (A or PR The compounds are also very Water soluble thereby lending themselves readily to various routes of administration particularly subcutaneous routes or topical applications, for instance under the form of collyrium.
These compounds are represented by the following basic structural formulas:
(I) and in which formulas X is a pharmaceutically acceptable anion such as chloride, iodide or bromide; Y is a quaternary ammonium radical of the group consisting of pyridinium trialkylamrnonium (-1%-8.lkylg) alkylpiperidinium alkyl alkylpyrrolidinium tiIryl 3,014,937 Patented Jan. 22, 1963 alkyl alltylmorpholinium alkyl-N-alkylpiperazinium alkyl and dialltyl-Nalkylpiperazinium alkyl alkyl Preferred and advantageous compounds are those according to the following formulas in which A is oxygen, sulfur or a single bond and Y is trimethylammonium, p'yridinium' or morpholinium and X .is as described above.
The compounds of this invention are prepared by condensing a diphenylyl mono or his glyoxal derivative with an alkanohydrazide ammonium halide having the following structure:
NH NHCOaIkyIYX (v) in which X and Y are as defined above for Formulas I and II. The starting material glyoxalcan also be used in the form of an addition compound such as a hydrate, alcoholate for instance ethylate or'methylate or a bisulfite addition product. These glyoxal starting materials are all described in copending applications. An excess of the hydrazide of Formula V is'usually employed. The
solvent is any unreactive organic solvent in which the reactants are mutually soluble. The lower alcohols, preferably, methanol, ethanol or isopropanol have been found to be very useful. Often a condensing acid such as acetic acid is advantageously present. Anhydrous conditions are particularly desirable. from 30 minutes to about three hours usually suflices for relatively complete reaction.
The products are isolated by cooling or by evaporation and trituration of the residue with ethyl ether. The desired quaternary products thereupon crystallize but because of their chemical and physical nature melting points cannot be obtained.
The term alkyl is used herein to define straight or branched saturated hydrocarbon residues of from 1 to 3 carbon atoms inclusive. Alkoxy groups are similarly comprised of 1 to 3 carbon atoms. The term reactive halide defines chloride, bromide or iodide anions. Of course other conventional nontoxic, pharmaceutically acceptable anions can be substituted therefor. Other modifications in the structures outlined are obvious to those skilled in the art such as other substituents in the henzene or heterocyclic portions of the chemical structures or using larger alkyl moieties however the essential features of the compounds of this invention are described hereabove and the methods of preparing representative compounds of this invention are described hereafter.
Example 1 A mixture of 2.26 g. of 4-phenoxyphenylglyoxal, 1.97 g. of acethydrazide pyridinium chloride, 5 ml.- of glacial acetic acid and 25 ml. of absolute ethanol is heated at reflux for 30 minutes. The mixture is cooled and evaporated. "The residue is triturated with anhydrous ethyl ether to obtain a white crystalline product,
4-phen oxyphenylcarbonyl) methinylhydrazidomethyl] pyridinium chloride.
Example 2 A mixture of 2.2 g. of 4-glyoxylyldiphenylmethane hydrate, 2.45 g. of acethydrazide pyridinium chloride, 5 ml. of glacial acetic acid and 25 m1. of absolute methanol are heated at reflux for 3 hours. Cooling separates the desired product, [(4-benzylphenylcarbonyl)methinylhydrazidomethyl] pyridinium chloride.
Example 3 A mixture of 1 g. of diphenylethane-4-glyoxal, 1 g. of acethydrazide pyridinium chloride, 2.5 ml. of acetic acid and 15 ml. of ethanol is heated at reflux for 3"hours,
A reflux period of phenylylcarbonyl)methinyl-hydrazidomethyl] pyridinium chloride.
Example 7 yl-4,4 bis(carbonylmethinylhydrazidomethylpyridinium cooled and concentrated. The residue is triturated with ether to give [(4-phenethylphenylcarbonyl)methinylhydrazidomethyl]pyridinium chloride.
Example 4 A mixture of 2.98 g. of 4,4-bisglyoxylyldiphenylethane, 5.4 g. of acethydrazide pyridinium bromide, 5 ml. of acetic acid and 25 ml. of methanol is heated at reflux for 3 hours. Cooling gives biphenylethane-4,4'-bis(carbonylmethinylhydrazidomethylpyridinium bromide).
Example 5 A mixture of 3.18 g. of 4,4-bisglyoxylyldiphenylether,
Example 6 A mixture of 2.56 g. of diphenylyl-4-glyoxal ethylate, 3 g. of acethydrazide pyridinium chloride, 5 ml. of acetic acid and 25 ml. of ethanol is heated at reflux for 30 minutes, then cooled. The mixture is evaporated to dry ness in vacuo to give, upon tr'ituration with ether, [(4-bichloride) Example 8 A mixture of 2.46 g. of biphenyl-4-glyoxal hydrate, 2.9 g. of acethydrazide methylmorpholinium iodide, 5 ml.
of acetic acid and 25 ml. of methanol is heated at reflux for 2 hours. The cooled mixture is concentrated and cooled to give the desired [(4-biphenylylcarbonyl)methinylhydrazidomethyl] methylmorpholinium iodide.
Example 9 A mixture of 2.3 g. of 4-phenylthiophenylglyoxal, 2.1 g. of acethydrazide trimethylammonium chloride, 7 ml. of acetic acid and 30 ml. of ethanol is heated at reflux for 4 hours, then worked up as above to give [(4-phenyl- 'thiophenylcarbonyl)methinylhydrazidomethyl] trimethylammonium chloride.
Example 10 A mixture of 2.4 g. of 4,4'-bis-glyoxylylstilbene hydrate, 5.1 g. of acethydrazide triethylammonium bromide, 5 ml. of acetic acid and 40 ml. of ethanol is reacted and worked up as in Example 3 to give stilbene-4,4-biscarbonylmethinylhydrazidomethyltriethylammonium bromide).
Example 11 A mixture of 3.3 g. of 4,4'-bisglyoxylyldiphenylsulfoxide ethylate, 5.8 g. of a-ethylacethydrazide methylpiperidinium bromide, prepared by quaternizing the hydrazide of Petrie and Horsley (US. Pat. No. 2,834,781), 10 ml. of acetic acid and 50 ml. of isopropanol is heated at reflux for 5 hours. Cooling, evaporation and trituration with ether gives the desired diphenylsulfoxide-4,4- bis(carbonylmethinylhydrazidoisopropyl methylpiperidinium bromide).
Example 12 A mixture of 1.5 g. of 2-phenoxyphenylglyoxal hydrate, 1.8 g. of acethydrazide trimethylammonium chloride, 5 ml. of acetic acid and 25 ml. of ethanol is heated at reflux for 2 hours and worked up as in Example 1 to give [(2-phenoxyphenylcarbonyl)methinylhydrazidomethyl] trimethylammonium chloride.
Example 13 A mixture of 1.2 g. of 4-phenylsulfonylphenylglyoxal, l g. of propionylhydrazide methylpyrrolidinium chloride, prepared by quaternizing the hydrazide of Petrie, 5 ml.. of acetic acid and 25 ml. of methanol is heated at reflux for several hours. Working up as described above gives [(4-phenyl-sulfonylphenylcarbonyl)methinylhydra-- zidoethyl] methylpyrrolidinium chloride.
Example 14 A mixture of 2.5 g. of biphenyl-4-glyoxal, 2.8 g. of acethydrazide N-methylpiperazinium dimethochloride, prepared as in Petrie, 10 ml. of acetic acid and 50 ml. of ethanol is heated at reflux for 4 hours, cooled and evaporated. Trituration with ether gives the desired diquaternary salt.
Example 15 A mixture of 2.7 g. of 4-phenoxyphenylglyoxal, 2.5 g. of acethydrazide methyl-N-methylpiperazinium chloride,
1O ml. of acetic acid and 40 ml. of isopropanol is heated at reflux for 2 hours, cooled and evaporated. Trituration with ether gives [(4-phenoxy-phenylcarbonyl) methinylidrazidomethyl] 1,4-dimethylpiperazinium chloride.
Example 16 A mixture of 2.8 g. of 4'-methoxybiphenylyl-4-glyoxal, 2.5 g. of acethydrazide pyridinium chloride, m1. of acetic acid and 75 ml. of methanol is heated at reflux for 30 minutes and worked up as in Example 1 to give [(4 methoxy 4 biphenylylcarbonyl)methinylhydrazidomethyl] pyridini'um chloride.
Example 17 A mixture of 1.5 g. of 3'-chloro-4'-1nethoxybiphenylyl- 4-glyoxal ethylate, 1.8 g. of acethydrazide trimethylammonium bromide and 100 ml. of isopropanol is heated at reflux for 6 hours. Working up as described above gives (3'-chloro-4'-methoxy-4-biphenyly1carbonyl methinylhydrazidomethyl] trimethylammonium bromide.
Example 18 Repeating Example 15 but using 1.2 g. of 4'-fiuoro biphenylyl-4-glyoxal gives the 4'-fluoro analogue; using 1.4 g. of the 4'-bromobiphenylyl-4-glyoxa1 gives the 4- bromo analogue; using 1.1 g. of the 4'-methylbipheny1-4- glyoxal gives the 4'-methyl quaternary.
Example 1 9 A mixture of 0.9 g. of 4-hydroxybiphenylyl-4-glyoxal hydrate, 1 g. of acethydr-azide pyridinium chloride, 5 ml. of acetic acid and 20 ml. of ethanol is heated at reflux for 1 hour to give the desired 4'-hydroxy-pyridiniurn chloride. Substituting the 4-n-propoxyglyoxal gives the corresponding 4-n-propoxy-pyridini1nn chloride.
Example 20 A mixture of 1.1 g. of 3.3'-bisglyoxylylbiphenyl is reacted With 2.2 g. of acethydrazide pyridinium chloride as described in Example 7 to give the 3,3-is0mer.
Example 21 and \ Q OOCH=NNHOOa1kylY.X g
in which alkyl is of from 1 to 3 carbon atoms; X is a reactive halide; Y is a quaternary ammonium radical selected from the group consisting of pyridinium, trialkylammonium, alkylpiperidinium, alkylpyrrolidinium, alkylmorphollnium, alkyl N alkylpiperazinium and dialkyl-N-alkylpiperazinium, each of said alkyi moieties is of from 1 to 3 carbon atoms; A represents a member selected from the group consisting of oxygen, sulfur, sulfonyl, sulfinyl, methylene, ethylene, vinylene and a direct link; R is a member selected from the group consisting of hydrogen, allroxy of from 1 to 3 carbon atoms, methyl, chloro and hydroxy; and R is a member selected from the group consisting of hydrogen and chloro. 2. A chemical compound of the formula:
in which X is a reactive halide.
3. [(4 phenoxyphenylcarbonyl)methinylhydraztidomethyl] pyridinium chloride.
4. Diphenylether 4,4 bis(carb.onylmethinylhydrazidomethyl pyridinium chloride) 5. Biphenyl 4,4 bis(carbonylrnethinylhydraz idomethylpyridinium chloride) 6. [(3' chloro 4-methoxy-biphenylcarbonyl)-methinylhydrazidomethyl] trimethylammonium bromide.
7. [(4 biphenylylcarbonyl)methinylhydrazidomethyl] methylrnorpholinium chloride.
References Cited in the file of this patent UNITED STATES PATENTS 2,670,348 Gregory et a1. Feb. 23, 1954 FOREIGN PATENTS 196,408 Austria Mar. 25, 1958 OTHER REFERENCES Seligman 'et a1.: Chemistry and Industry, 1954, page 1195.
Forss et al.: Nature, vol. 173, pages 401-2 (1954).

Claims (2)

1. A QUATERNARY SALT SELECTED FROM THE GROUP CONSISTING OF COMPOUNDS OF THE FORMULAE:
2. A CHEMICAL COMPOUND OF THE FORMULA:
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3478033A (en) * 1967-05-25 1969-11-11 Us Agriculture Preparation of 1,1,4,4-tetraethylpiperazinium dichloride
US3506666A (en) * 1966-12-05 1970-04-14 Dow Chemical Co 1-methyl-1-(substituted)-4-(pentachloro-phenyl)piperazinium salts
US20090186900A1 (en) * 2006-02-27 2009-07-23 Nigel Vicker Compound
JP2009528367A (en) * 2006-03-02 2009-08-06 サイガ・テクノロジーズ・インコーポレーテッド Antiviral drugs for the treatment of arenavirus infection

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2670348A (en) * 1952-06-10 1954-02-23 Du Pont Girard derivatives of 5-halosalicylaldehydes
AT196408B (en) * 1956-01-06 1958-03-25 Cilag Ag Process for the preparation of new hydrazones

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2670348A (en) * 1952-06-10 1954-02-23 Du Pont Girard derivatives of 5-halosalicylaldehydes
AT196408B (en) * 1956-01-06 1958-03-25 Cilag Ag Process for the preparation of new hydrazones

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3506666A (en) * 1966-12-05 1970-04-14 Dow Chemical Co 1-methyl-1-(substituted)-4-(pentachloro-phenyl)piperazinium salts
US3478033A (en) * 1967-05-25 1969-11-11 Us Agriculture Preparation of 1,1,4,4-tetraethylpiperazinium dichloride
US20090186900A1 (en) * 2006-02-27 2009-07-23 Nigel Vicker Compound
JP2009528367A (en) * 2006-03-02 2009-08-06 サイガ・テクノロジーズ・インコーポレーテッド Antiviral drugs for the treatment of arenavirus infection
US8492434B2 (en) 2006-03-02 2013-07-23 Siga Technologies Inc. Antiviral drugs for treatment of arenavirus infection
US9199920B2 (en) 2006-03-02 2015-12-01 Kineta Four, LLC Antiviral drugs for treatment of arenavirus infection

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