GB2119651A - Antiviral composition containing aminosulphonylbenzoate compounds - Google Patents
Antiviral composition containing aminosulphonylbenzoate compounds Download PDFInfo
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- GB2119651A GB2119651A GB08312121A GB8312121A GB2119651A GB 2119651 A GB2119651 A GB 2119651A GB 08312121 A GB08312121 A GB 08312121A GB 8312121 A GB8312121 A GB 8312121A GB 2119651 A GB2119651 A GB 2119651A
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- C—CHEMISTRY; METALLURGY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
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- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
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Abstract
Antiviral pharmaceutical composition which contains as an active ingredient a pharmaceutically effective amount of a compound of the formula (I): <IMAGE> wherein X and Y are independently chlorine, bromine, fluorine, or hydrogen; R1 is cyclohexyl, benzyl, allyl or straight chain or branched chain alkyl having one to twelve carbon atoms, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. Administration may be oral, rectal, topical or by injection.
Description
SPECIFICATION
A pharmaceutical composition having antiviral activity and method for treating a patient suffering from viral diseases therewith
The present invention relates to a pharmaceutical composition having antiviral activity and a method for treating a patient suffering from viral diseases therewith.
Vaccines which have been used for viral diseases are slow-acting and their utility is limited only to preventive use. Moreover, since the antigenicity of viruses often changes, the effect of vaccines has not been sufficient.
Upon strenuous and extensive study of medicines which possess fast-acting therapeutic activity, the present inventors have found that specific aminosulfonylhalogenobenzoates and their pharmaceutically acceptable salts exhibit excellent antiviral activity, and accomplished the present invention based on this finding.
SUMMARY OF THE INVENTION
An object of the present invention is, therefore, to provide a pharmaceutical composition having antiviral activity.
Another object of the present invention is to provide a method for treating a patient suffering from viral diseases.
The pharmaceutical composition according to the present invention contains as an active ingredient an aminosulfonylbenzoate compound of the formula (I):
wherein X and Y are independently chlorine, bromine, fluorine, or hydrogen; R1 is cyclohexyl, benzyl, allyl or straight chain or branched chain alkyl having one to twelve carbon atoms. The treatment is performed with a pharmaceutically effective amount of the compound of the formula (I), together with other pharmaceutically acceptable carriers, fillers, base materials, excipients, etc.
These and other objects and features of the invention will be well appreciated upon reading the following description.
DETAILED DESCRIPTION OF THE INVENTION
The compounds according to the present invention are represented by the formula (I):
wherein X and Y are independently chlorine, bromine, fluorine, or hydrogen; R1 is cyclohexyl, benzyl, allyl or straight chain or branched chain alkyl having one to twelve carbon atoms.
The straight chain or branched chain alkyl group in R1 having one to twelve carbon atoms may be specifically methyl group, ethyl group, iso-propyl group, n-propyl group, n-butyl group, sec-butyl group, or n-octyl group; preferably, X and Y are not both hydrogen atom at the same time.
The aminosulfonyl group may be preferably bonded to the 3 or 5 position of the benzene ring, while X and Y may be preferably bonded to the 2 and/or 4 position of this ring.
The compounds which are active ingredients of the pharmaceutical compositions according to the present invention may be prepared as follows: First, halogenoaminosulfonylbenzoic acid chloride is obtained by heating halogenoaminosulfonylbenzoic acid in thionyl chloride (See British Patent No.
91 5,259). Halogenoaminosulfonylbenzoic acid chloride thus obtained is then reacted with an alcohol of the formula ROH, wherein R is cyclohexyl, benzyl, allyl, or straight chain or branched chain alkyl having one to twelve carbon atoms, at room temperature or under heating if necessary, in a solvent such as dioxane, tetrahydrofuran, chloroform, dichloromethane, benzene, etc., or using the alcohol itself as a solvent so as to obtain the desired product.
The manufacture of the compounds which are active ingredients of the pharmaceutical compositions according to the present invention will be described below with reference to specific synthesis examples.
SYNTHESIS EXAMPLE 1
1.08 g of benzyl alcohol was added to 2.89 g of 5-aminosulfonyl-2,4-dichlorobenzoic acid chloride. After two hours of refluxing under heating, dioxane was recovered at reduced pressure and the residue was recrystallized from methanol to obtain 3.1 9 g of benzyl 5-aminosulfonyl-2,4dichlorobenzoate as white crystals. When measured in accordance with the method prescribed in the
Japanese Pharmacopoeia, the crystals melted at 161.5-1 630C. The elementary analysis of this product is shown below.
C H Cl N S
Calculated: 46.68 3.08 19.68 3.89 8.90
Found: 46.40 3.01 19.39 3.92 8.75
SYNTHESIS EXAMPLE 2
2.38 g of 3-aminosulfonyl-4-fluorobenzoic acid chloride were added to 1 5 ml of methanol. After
reaction at room temperature for four hours, the reaction mixture was concentrated under reduced
pressure, and the precipitated crystals were filtered out. The crystals were then recrystallized from
methanol to obtain 1.84 g of methyl 3-aminosulfonyl-4-fluorobenzoate as white crystals. When
measured in accordance with the method prescribed in the Japanese Pharmacopoeia, the crystals
melted at 1 22-1 240C. The elementary analysis of this product is shown below.
C H F N S
Caiculated: 41.20 3.46 8.15 6.01 13.75
Found: 41.40 3.41 8.10 5.92 13.65
The compounds shown in Table 1 were prepared in a similar manner to those in Examples 1 and 2
TABLE 1
Example
No. Compound Name Appearance m.p.
iso-propyl 3-a minosulfonyl white crystalline
3 4-bromobenzoate powder 187-1 900C n-butyl 3-aminosulfonyl white crystalline
4 4-bromobenzoate powder 100--1 050C methyl 5-aminosulfonyl-2,4- white crystalline
5 dichlorobenzoate powder 201 .5-2040C ethyl 5-aminosulfonyl-2,4- white crystalline
6 dichlorobenzoate powder 124-1 26.50C n-propyl 5-aminosulfonyl white crystalline
7 2,4-dichlorobenzoate powder 124-1 26.50C iso-propyl 5-aminosulfonyl- white crystalline
8 2,4-dichlorobenzoate powder 149.5--151 OC n-butyl 5-aminosulfonyl white crystalline
9 2,4-dichlorobenzoate powder 90-920C sec-butyl 5-aminosulfonyl white crystalline
10 2,4-dichlorobenzoate powder 137.5-1 420C n-octyl 5-aminosulfonyl- white crystalline
11 2,4-dichlorobenzoate powder 81-860C TABLE 1 (continued)
Example
No. Compound Name Appearance m.p.
cyclohexyl 5-aminosulfonyl- white crystalline
12 2,4-dichlorobenzoate powder 130-1330C allyl 5-aminosulfonyl-2,4- white crystalline
13 dichlorobenzoate powder 109--112"C methyl 5-aminosulfonyl-4- white crystalline
14 chloro-2-fluorobenzoate powder 157-161 0C ethyl 5-aminosulfonyl-2- white crystalline 1 5 chloro-4-fluorobenzoate powder 123-1 290C Next, the effectiveness, safety, dosage of application, method for application and formulation of the pharmaceutical compositions according to the present invention will be described with reference to specific examples which are merely illustrative of the invention but should not be interpreted to restrict the scope thereof.
EXPERIMENTAL EXAMPLE 1
Protective Action against the Infection of Mice with Influenza Virus A/WSN After the influenza virus A/WSN was intranasally inoculated to groups each consisting of ten mice, each compound of the invention to be examined was given intraperitoneally once one hour after the
infection. Survival rate was observed 1 5 days after the infection. The results are shown in Table 2. In a similar test, after intranasal inoculation, each compound to be examined was orally administered to the
mice. Survival rate was observed after 1 5 days. The results are shown in Table 3.
TABLE 2
Dosage Survival Dosage Survival Compound mg/kg rate % Compound mg/kg rate % Control - 0 30 30 10 Amantadine 100 40 100 40 30 40 10 50 2 11 100 50 30 60 10 50 30 30 4 12 30 70 100 40 30 40 30 30 7 13 100 50 100 40 30 30 30 30 8 14 100 40 100 50 TABLE 3
Dosage Survival Dosage Survival Compound mg/kg rate % Compound mg/kg rate % Control - 0 100 50 7 Amantadine 300 40 300 60 100 30 30 40 3 9 300 40 100 60 30 50 30 50 -4 11 100 60 100 70 100 40 100 30 5 1 300 50 300 40 100 40 100 40 6 15 300 50 300 50 As shown in the above tables, all of the compounds examined indicated markedly higher survival rates in the treated groups as compared with that of the control.Effectiveness of aminosulfonylbenzoate derivatives was supported by these experiments.
EXPERIMENTAL EXAMPLE 2
Protective Action against the Infection of Mice with Influenza Virus B/GL
After the influenza virus B/GL was intranasally inoculated to groups each consisting of ten mice, each compound of the invention to be examined was given orally once one hour after the infection.
Survival rate was observed 1 5 days after the infection. The results are shown in Table 4.
TABLE 4
I Dosage Survival Dosage Survival Compound mg/kg rate 96 Compound mg/kg rate % Control - 0 100 40 7 Amantadine 300 30 300 50 100 30 30 40 3 3 1 9 300 40 100 60 30 60 30 50 4 11 300 70 100 80 100 40 100 30 5 14 300 50 300 50 As shown in the table, all of the compounds examined indicated protective action against the death of mice infected with influenza virus B/GL.Especially, compounds 4, 9 and 11 showed extremely excellent activity.
EXPERIMENTAL EXAMPLE 3
Acute Toxicity in Mice
Each compound of the invention was suspended in 5% Arabic gum solution and given orally or intraperitoneally to groups each consisting of ten ddY male mice weighing about 25 g at the dosage volume of 10 ml/kg. The mortality rate was observed for 7 days. LD50 was determined according to the method of Wilcoxon and Litchfield. The results are shown in Table 5.
TABLE 5
LD50 Value (mg/kg)
Intra- Intra Oral peritoneal Oral peritoneal Compound administration administration Compound administration administration 1 3000 1000 9 3000 1000 2 3000 1000 10 3000 1000 3 3000 1000 11 3000 1000 4 3000 1000 12 3000 1000 5 3000 1000 13 3000 1000 6 3000 1000 14 3000 1000 7 3000 1000 15 3000 1000 8 8 3000 1000 EXPERIMENTAL EXAMPLE 4
Protective Action against the Infection of Mice with Coxsackie Virus Bt After the coxsackie virus B, was intraperitoneally inoculated to groups each consisting of ten mice, each compound of the invention to be examined was given orally once one hour after the infection.
Survival rate was observed 10 days after the infection. The results are shown in Table 6.
TABLE 6
Dosage Survival Dosage Survival Compound mg/kg rate % Compound mg/kg rate % Control - 10 300 40 9 1000 80 300 40 300 50 4 11 1000 70 1000 80 As shown above, all of the compounds examined showed protective action against the death of mice infected with the virus.
EXPERIMENTAL EXAMPLE 5
Protective Action against the Infection of Mice with Parainftuenza Virus Type 3
After the parainfluenza virus type 3 was intranasally inoculated to groups each consisting of ten mice, each compound of the invention to be examined was given orally once one hour after the infection. Survival rate was observed 1 5 days after infection. The results are shown in Table 7.
TABLE 7
Dosage Survival Dosage Survival Compound mg/kg rate % Compound mg/kg rate % Control - 0 30 30 9 100 60 30 40 30 40 4 11 100 60 100 70 Table 7 shows that all of the examined compounds indicated the protective action against the death of mice infected with virus.
As apparent from the above experimental examples, all of compounds 1 to 1 5 have antiviral activity of wide spectrum and are of extremely high safety. Therefore, they have very high clinical utility for treating various infectious diseases which are caused from virus infection, for example, upper respiratory infection, pneumonia, bronchitis and so on.
In case that the compounds of the present invention are administered to a human patient, the dosage for an adult is 10-5,000 mg per day for compounds 4, 9 and 11; 30-5,000 mg per day for compounds 2, 5, 6,7, 14 and 15; 50-5,000 mg per day for compounds 1,3,8, 10, 12 and 13.
However, the dosage may be increased or decreased according to symptoms, ages, etc., in a known manner.
Compounds 1 to 1 5 can be formulated as pharmaceutical preparations by conventional methods with pharmaceutical carriers, base materials or excipients commonly used for this purpose. Examples of solid carriers and excipients usable advantageously herein include common base materials such as mannitol, corn starch and potato starch, binders such as crystalline cellulose, cellulose derivatives, arabic gum, corn starch and gelatin; disintegrators such as corn starch, potato starch and calcium carboxymethylcellulose; and lubricants such as talc and magnesium stearate. Examples of liquid carriers
usable advantageously herein include distilled water for injection, physiological saline solution, dextrose
aqueous solution, vegetable oils for injection and glycols such as propylene glycol and polyethylene
glycol.
Such preparations can, for example, be in the form of capsules, tablets, powders or oral liquid
preparations (including dry syrups) for oral application; rectum suppositories for intra-rectal application;
for injection, they can be, for example, freezedried preparations which can be dissolved in distilled water
for injection immediately before administration; other preparations such as nose drops or inhalant can
also be adopted.
The following are examples of pharmaceutical preparations, but such preparations are not limited
only to the illustrated ones.
EXAMPLE 1
Tablets
I) Compound 4 50 g
II) Lactose proper amounts
Ill) Crystalline cellulose 60 g
IV) Potato starch 54 g
V) Magnesium stearate 2 9
2009
The ingredients (I) to (IV) were homogeneously mixed and 10% paste from the part of the
ingredients (IV) which had been previously separated was added to the above mixture to prepare
granules, and then the granules were dried. Next, the granules were mixed with the ingredient (V) to
provide tablets each weighing 200 mg. If desired, the tablets may be coated with sugar in a usual
manner.
EXAMPLE 2
EXAMPLE 2
10% Powders
Compound 9 100 g
Lactose 890 9 Magnesium stearate 10 9 1000 g
After each of the above ingredients was weighed, the ingredients were homogeneously mixed to prepare 10% powders.
EXAMPLE 3
Capsules
I) Compound 11 50 g
II) Calciumhydrogenphosphate 50 g III) Aluminum silicate proper amount
IV) Crystalline cellulose 60 g
V) Magnesium stearate 2 9 2009 The above ingredients (I) to (V) were put together and mixed wel!. through a sieve; capsules each
weighing 200 mg were prepared from the mixture in a usual manner.
Claims (49)
1. Antiviral pharmaceutical composition which contains as an active ingredient a pharmaceutically
effective amount of a compound of the formula (I):
wherein X and Y are independently chlorine, bromine, fluorine, or hydrogen; R1 is cyclohexyl, benzyl, allyl or straight chain or branched chain alkyl having one to twelve carbon atoms, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
2. Pharmaceutical composition according to claim 1, wherein the compound of the formula (I) is a compound of the formula (all):
wherein X1, Y1 and R1 are the same meanings as given above with respect to X, Y and R respectively.
3. Pharmaceutical composition according to claim 1, wherein the straight chain or branched chain alkyl is one selected from the group consisting of methyl, ethyl, propyl, butyl, and octyl.
4. Pharmaceutical composition according to claim 1, wherein the compound of the formula (I) is benzyl 5-aminosulfonyl-2,4-dichlorobenzoate.
5. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is methyl 3-am inosulfonyl-4-fluorobenzoate.
6. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is iso-propyl 3-a minosulfonyl-4-bromobenzoate.
7. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is n butyl 3-aminosulfonyl-4-bromobenzoate.
8. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is methyl 5-aminosulfonyl-2,4-dichlorobenzoate.
9. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is ethyl 5-am inosulfonyl-2,4-dichlorobenzoate.
10. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is n-propyl 5-aminosulfonyl-2,4-dichlorobenzoate.
11. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is iso-propyl 5-aminosu lfonyl-2,4-dichlorobenzoate.
12. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is n-butyl 5-aminosulfonyl-2,4-dichlorobenzoate.
13. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is sec-butyl 5-am inosu lfonyl-2,4-dich lorobenzoate.
14. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is n-octyl 5-a minosu lfonyl-2,4-dichlorobenzoate.
1 5. Pharmaceutical composition according to claim 1, wherein the compound of the formula (I) is cyclohexyl 5-aminosu Ifonyl-2,4-dichlorobenzoate.
1 6. Pharmaceutical composition according to claim 1 , wherein the compound of the formula (I) is allyl 5-aminosulfonyi-2,4-dichlorobenzoate.
1 7. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is methyl 5-aminosulfonyl-4-fluorobenzoate.
1 8. Pharmaceutical composition according to claim 3, wherein the compound of the formula (I) is ethyl 5-aminosu lfonyl-2-chloro-4-fluorobenzoate.
19. A pharmaceutical composition according to claim 1 in which the carrier is at least one member selected from the group consisting of Tween 80, arabic gum, lactose, magnesium stearate, potato starch, polyvinylalcohol and polyethylene glycol.
20. A pharmaceutical composition according to claim 3 in which the carrier is at least one member selected from the group consisting of Tween 80, arabic gum, lactose, magnesium stearate, potato starch, polyvinyl alcohol and polyethylene glycol.
21. A pharmaceutical composition according to claim 1 which is in a form selected from the group consisting of an oral dosage form, a rectal dosage form, an injectable form and a topical application form.
22. A pharmaceutical composition according to claim 3 which is in a form selected from the group consisting of an oral dosage form, a rectal dosage form, an injectable form and a topical application form.
23. A pharmaceutical composition according to claim 1 9 which is in a form selected from the group consisting of an oral dosage form, a rectal dosage form, an injectable form and a topical application form.
24. A pharmaceutical composition according to claim 20 which is in a form selected from the group consisting of an oral dosage form, a rectal dosage form, an injectable form and a topical application form.
25. A method for treating a patient suffering from a viral disease, which method comprises administering to said patient needing treatment for such a disease an effective amount for treating such a disease of a compound of the formula (I):
wherein X and Y are independently chlorine, bromine, fluorine, or hydrogen; R, is cyclohexyl, benzyl, allyl or straight chain or branched chain alkyl having one to twelve carbon atoms, or a pharmaceutically acceptable salt thereof.
26. A method according to claim 25, wherein the compound of the formula (I) is a compound of -the formula (it):
wherein X1, Y, and R1 are the same meanings as given above with respect to X, Y and R respectively.
27. A method according to claim 25 in which a daily dose of the compound of the formula (I) or the salt thereof is in the range of 10 mg to 5,000 mg.
28. A method according to claim 25 in which the compound of the formula (I) or the salt thereof is administered by a route selected from the group consisting of oral administration, intrarectal administration, injection and topical administration.
29. A method according to claim 26 in which the compound of the formula (I) or the salt thereof is administered by a route selected from the group consisting of oral administration, intrarectal administration, injection and topical administration.
30. Method according to claim 26, wherein the compound of the formula (I) is benzyl 5 aminosulfonyl-2,4-dichlorobenzoate.
31. Method according to claim 26, wherein the compound of the formula (I) is methyl 3aminosulfonyl-4-fluorobenzoate.
32. Method according to claim 26, wherein the compound of the formula (I) is iso-propyl 3aminosulfonyl-4-bromobenzoate.
33. Method according to claim 26, wherein the compound of the formula (I) is n-butyl 3aminosu Ifonyl-4-bromobenzoate.
34. Method according to claim 26, wherein the compound of the formula (I) is methyl 5 aminosulfonyl-2,4-dichlorobenzoate.
35. Method according to claim 26, wherein the compound of the formula (I) is ethyl 5aminosulfonyl-2,4-dichlorobenzoate.
36. Method according to claim 26, wherein the compound of the formula (I) is n-propyl 5 aminosulfonyl-2A-dichlorobenzoate.
37. Method according to claim 26, wherein the compound of the formula (I) is iso-propyl 5aminosu Ifonyl-2,4-dichlorobenzoate.
38. Method according to claim 26, wherein the compound of the formula (I) is n-butyl 5 aminosulfonyl-2,4-dichlorobenzoate.
39. Method according to claim 26, wherein the compound of the formula (I) is sec-butyl 5aminosulfonyl-2,4-dichlorobenzoate.
40. Method according to claim 26, wherein the compound of the formula (I) is n-octyl 5 aminosulfonyl-2,4-dichlorobenzoate.
41. Method according to claim 26, wherein the compound of the formula (I) is cyclohexyl 5 aminosulfonyl-2,4-dichlorobenzoate.
42. Method according to claim 26, wherein the compound of the formula (I) is allyl 5aminosulfonyl-2,4-dichlorobenzoate.
43. Method according to claim 26, wherein the compound of the formula (I) is methyl 5 aminosulfonyl-2-fluorobenzoate.
44. Method according to claim 26, wherein the compound of the formula (I) is ethyl 5 aminosulfonyl-2-chloro-4-fluorobenzoate.
45. Method according to claim 25, in which the carrier is selected from the group consisting of
Tween 80, arabic gum, lactose, magnesium stearate, potato starch, polyvinylalcohol and polyethylene glycol.
46. Method according to claim 26, in which the carrier is selected from the group consisting of
Tween 80, arabic gum, lactose, magnesium stearate, potato starch, polyvinylalcohol and polyethylene glycol.
47. Method according to claim 45, in which the compound is administered in a form selected from the group consisting of an oral dosage form, a rectal dosage form, an injectable form and a topical application form.
48. Method according to claim 46, in which the compound is administered in a form selected from the group consisting of an oral dosage form, a rectal dosage form, an injectable form and a topical application form.
49. A pharmaceutical composition as claimed in claim 1 and substantially as described in any one of the specific examples hereinbefore set forth.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57075782A JPS58192820A (en) | 1982-05-06 | 1982-05-06 | Antiviral medicinal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8312121D0 GB8312121D0 (en) | 1983-06-08 |
| GB2119651A true GB2119651A (en) | 1983-11-23 |
Family
ID=13586123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08312121A Withdrawn GB2119651A (en) | 1982-05-06 | 1983-05-04 | Antiviral composition containing aminosulphonylbenzoate compounds |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS58192820A (en) |
| DE (1) | DE3316611A1 (en) |
| FR (1) | FR2526316A1 (en) |
| GB (1) | GB2119651A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB915259A (en) * | 1960-05-09 | 1963-01-09 | Parke Davis & Co | 4-halo-3-sulfamoylbenzoic acid esters and methods for producing same |
| GB1260155A (en) * | 1969-04-29 | 1972-01-12 | Leo Pharm Prod Ltd | Sulphonamido anthranilic acid derivatives |
| GB1561243A (en) * | 1976-03-18 | 1980-02-13 | Richter Gedeon Vegyeszet | Sulphonamides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB853199A (en) * | 1958-08-05 | 1960-11-02 | Glenn Herbert Hamor | 2-sulfamoylbenzoic acid esters |
| EP0068408A1 (en) * | 1980-11-10 | 1983-01-05 | Mochida Pharmaceutical Co., Ltd. | Antiviral compositions and a method for treating virus diseases |
| JPS5817167B2 (en) * | 1980-11-10 | 1983-04-05 | 持田製薬株式会社 | Pharmaceutical composition with antiviral action |
-
1982
- 1982-05-06 JP JP57075782A patent/JPS58192820A/en active Pending
-
1983
- 1983-05-04 GB GB08312121A patent/GB2119651A/en not_active Withdrawn
- 1983-05-06 FR FR8307644A patent/FR2526316A1/en active Pending
- 1983-05-06 DE DE19833316611 patent/DE3316611A1/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB915259A (en) * | 1960-05-09 | 1963-01-09 | Parke Davis & Co | 4-halo-3-sulfamoylbenzoic acid esters and methods for producing same |
| GB1260155A (en) * | 1969-04-29 | 1972-01-12 | Leo Pharm Prod Ltd | Sulphonamido anthranilic acid derivatives |
| GB1561243A (en) * | 1976-03-18 | 1980-02-13 | Richter Gedeon Vegyeszet | Sulphonamides |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8312121D0 (en) | 1983-06-08 |
| DE3316611A1 (en) | 1983-11-10 |
| JPS58192820A (en) | 1983-11-10 |
| FR2526316A1 (en) | 1983-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |