CA1335259C - Composition of spent liquor from pulping process for antiviral medicine - Google Patents
Composition of spent liquor from pulping process for antiviral medicineInfo
- Publication number
- CA1335259C CA1335259C CA 612816 CA612816A CA1335259C CA 1335259 C CA1335259 C CA 1335259C CA 612816 CA612816 CA 612816 CA 612816 A CA612816 A CA 612816A CA 1335259 C CA1335259 C CA 1335259C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- spent liquor
- lignin
- cells
- sulfite
- 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 - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/13—Coniferophyta (gymnosperms)
- A61K36/15—Pinaceae (Pine family), e.g. pine or cedar
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A composition for anti-AIDS viral and other antiviral medicines having spent liquor from sulfite pulping and/or processed products thereof as the major constituent and preventive and/or therapeutic method(s) against AIDS viral and other viral infections are presented.
Description
1 33525~
COMPOSITION FOR ANTIVIRAL MEDICINES
BACKGROUND OF THE INVENTION
The present invention relates to the use of lignin derivatives for antiviral drugs, in particular, to the prevention of and the therapy against AIDS (Acquired Immune Deficiency Syndrome) virus.
The number of patients with AIDS has abruptly increased recently, centering on the U.S.A. and Africa, and currently it amounts to about fifty thousand persons, the virus carriers existence being about a hundred times as many, all over the world. It is said that almost all virus carriers come down with the disease within five years and the death rate reaches about 100%. AIDS causes the immune system of living bodies to collapse through the fact that the AIDS virus infects the helper T cells governing the immune system and destroys them.
As a result, persons succumb to opportunistic infections, malignant tumors or the like, and die with this disease.
To date, nucleic acid-based AZT (azidothymidine) alone is approved as a therapeutic drug for use against AIDS. The AZT, however, cannot be used for a long term, due to its intensive side effects (anemia, etc.).
On the other hand, lignin exists abundantly in nature, after cellulose, and is contained in almost all plants, and has been ingested by human beings as a part of their food.
Recently, the physiological effects (for intestinal disorders, etc.) thereof are attracting attention as a vegetable fiber.
Moreover, the production of lignin derivatives is centered on spent liquor in the pulp and paper industry. The potential thereof as a medicinal drug, however, has been hardly investigated and merely its antitumoral property is known.
Thus, the physiological effects of ligninsulfonic acid and other lignin derivatives and, in particular, its antiviral 3~ effect against NDV (Newcastle Disease Virus) belonging to the 1 33525q -paramyxovirus family and RSV (Rous Sarcoma Virus) and HIV
(Human Immunodeficiency Virus) belonging to the retrovirus family, to which the AIDS virus also belongs, has been investigated, leading to the completion of the invention.
SUMMARY OF THE INVENTION
The gist of the invention lies in a composition for anti-AIDS viral and other antiviral medicines having spent liquor from sulfite pulping and/or processed products as the major constituent.
DETAILED DESCRIPTION OF THE INVENTION
First, the antiviral activity of sulfite spent liquor was determined to find that activity is exhibited at about 1.5 mg/ml against NDV and at about 100 ,ug/ml against RSV. Next, the sulfite spent liquor was fractionated through ultrafilters (UK type) with fractional molecular weights of 10,000 and 1,000. The quantities of sugars, ashes and ligninsulfonic acid in each fraction were determined and the antiviral activity was tested to obtain the results as shown in Table 1 below.
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~: o ~ o oo ^ o n ~ o~ o 1 33525'~
It has been found that the substance which exhibits the antiviral activity resides in ligninsulfonic acid and, in particular, the fraction which exhibits high activity has a molecular weight on the high side. This fraction also exhibited potent antiviral activity against HIV. However, this fact does not deny the existence of antivirus-active substances, except ligninsulfonic acid, in sulfite spent liquor.
The methods of testing for antiviral activity are set out below.
In a test for anti-NDV activity, primary culture cells CEF (Chick Embryo Fibroblast) were proliferated on a plate with 96 holes and infected with NDV. Then, after 30 minutes, progressively diluted samples were added and, 24 hours later, the concentration needed to inhibit cell fusion caused by the virus was determined under a microscope.
In a test for anti-RSV activity, following the proliferation of said CEF on a plate with 96 holes, the CEF
was infected with RSV. After 1 hour, progressively diluted samples were added and, 5 days later, the concentration required to inhibit the transformation caused by the virus was determined under a microscope.
For the anti-HIV test, MT-4 (human T cells infected by HTLV-1) and HTLV-IIIb were used as the cells and virus, respectively. The virus medium was prepared from the culture supernatant of Nolt 4/HIVHTLV_IIIb cells being HIV-producing cells. The titer of virus was 1 x 106 TCIDso/ml. RPMI 1640 (cont~i n ing antibiotics) was used as a medium. For the culture, equal quantities of MT-4 cells of 1 x 106 cells/ml and HTLV-IIIb of 2 x 104 TCIDso/ml were added to each well of a plate with 24 holes, which was cultured for 1 hour to allow adsorbtion of the virus. Thereafter, sample solutions diluted to various concentrations were added and, finally, the medium was added to make up the volume to 1 ml, which was cultured 3~ for 4 days in a CO2 incubator of 37 C. As the references, _ 4 -d 3 3 5 2 5 q cultures with cells not infecte by HTLV-IIIb and without the addition of sample were performed. The antiviral effect was judged by two methods; the inhibition of cell degeneration due to HIV and the inhibition of the development of HIV specific antigen onto the surface of cells. First, the cell degeneration effect was judged from the inhibition of the lethal effect on cells through the addition of sample by counting the number of living cells using the trypan blue method for the four-day culture medium, both infected and not infected by HIV. For the determination of HIV specific antigen, after reacting the cells fixed with methanol first with anti-HIV human serum for 40 minutes at 37 C, FITC-labelled anti-human-IgG was added and allowed to react for 40 minutes at 37 C and then the number of fluorescently labelled cells were counted using a fluorescent microscope.
Next, the antiviral activity was determined for various lignin derivatives, also.
Results are shown in Table 2.
The methods of preparing samples in said table are as follows:
3~
1 33525q o Sodium ligninsulfonate Produced by treating calcium ligninsulfonate with sodium sulfate to exchange the base.
o Calcium ligninsulfonate Produced by cooking red pine with cooking liquor of calcium sulfite (CaS03).
o Magnesium ligninsulfona~e Produced by cooking red pine with cooking liquor of magnesium sulfite (MgS03).
o Kraft lignin Produced by kraft pulping of red pine to field bleached kraft pulp ~residual lignin in pulp : 2.0 %).
Composition of kraft spent liquor (inorganics 6.2 %, sugars 2.8 %, lignin 6.0 %).
o Dioxane ligin Extracted from wood flour (spruce) treated with alcohol-benzene by heating for 2 hours at 175 C in a mixed liquor of dioxane-water (1 : l) according to the method of Sakakibara et al.
The yield was about 45 %.
o Thioglycolic acid lignin Prepared according to Brauns et al in a way that degreased wood flour (birch) was added to 2 mixed liquor of thio~lycolic acid with 2N hydrochloric acid to boil for 7 hours, the mass was then separated by filtration and, after washing with water and with ethanol, the residue was extracted with 2 % sodium -hydroxide. The lignin was recovered after being precipitated with hydrochloric acid.
o Sulfomethylated product of kraft lignin Prepared in a way that Na2SO3 (10 to 20 % based on kraft lignin) and then HCHO (equimols to Na2SO3) were added to a slurry (about 25 ~) of kraft lignin to treat for 1 to 2 hours at 60 to 80 C and, after treating further for 2 to 3 hours at 130 to 150 C, cooling and drying.
Table 2 Sample Anti-NDV activity Anti-RSV activity Sodium ligninsulfonate 0.3 mg/ml 0.03 mg/ml Calcium ligninsulfonate 0.4 0,04 Magnesium ligninsulfonate 0.2 0.03 Kraft lignin 1.2 0.1 Dioxane lignin 1.5 0.2 Th~oglycolic acid lignin 0.8 0.1 Sulfomethylated product 0 5 0 07 of kraft lignin -As noted above, the antiviral activity was recognized with all lignin derivatives listed in the table and thereamong ligninsulfonic acids were proved to have a very potent antiviral effect. The useful lignin derivatives are not confined to those in the table and any one currently known will serve.
In the following, the invention will be exemplified, based on the examples, but the invention is not confined to these.
Example 1 Using a dialyzing membrane, 100 ml of sulfite spent liquor shown in Table 1 was dialyzed for 4 days against tap water and for 3 days against deionized water in batch. The liquor, having finish-ed the dialysis,was concentrated to about 30 ml with arotary evapo-rator and then freeze-dried to obtain about 3.5 g of fraction rich in ligninsulfonic acid. Both reducing sugar and ash in this fraction decreased to about one tenth compared with those of the original sulfite spent liquor. When determining the anti-NDV and anti-RSV activities, this fraction exhibited the effect at 0.5 mg/ml and 0.04 mg/ml, respectively.
Example 2 After 100 ml of kraft spent liquor shown in Table 2 was adjusted to pH 3.0 to precipitate the portion of kraft lignin, this was centrifuged (10,000 rpm) to collect the precipitated fraction. Then, this was converted to powder by drying under reduced pressure to obtain about 4.0 g of fraction rich in kraft lignin. Suspending this into deionized water, lN NaOH was added to completely dissolve and a solution with a final concentration of 1 % was prepared. When determining the anti-NDV and anti-RSV activities using said kraft lignin solution, the effect was seen at 0.8 mg/ml and 0.07 mg/ml, respectively, in terms of solids.
Example 3 Using a portion of sulfite spent liquor with a fractional molecular weight of over 10,000 shown in Table 1, the anti-HIV
activity was determined. Results are shown in Table 3 -- 1 33525~
Table 3 Concentration Number of living Number of living Positivity of of sample cells when not in- cells when infected HIV specific fected by HIV by HIV antigen 5500 ~g/ml 1.36 x 106/ml 1.08 x 106/ml 0 %
250 1.46 1.41 0 125 1.57 1.45 0 63 1.53 1.61 0 32 1.58 1.66 0 16 1.56 1.53 0 8 1.58 1.5~ 0 4 1.59 0.96 20 0 1.61 0.21 90 2~ From the results above, it became clear that the anti-HIV
activity of the fraction of sulfite spent liquor with a molecular weight of over 10,000 inhibited completely both the cell degenera-tion due to virus and the development of HIV specific antigen at a very low concentration of 8 ~g/ml and the toxicity against cells was only generated slightly at a high concentration of 500 ~g/ml proving the fraction to be an antiviral agent with very high SI (Selective Index).
COMPOSITION FOR ANTIVIRAL MEDICINES
BACKGROUND OF THE INVENTION
The present invention relates to the use of lignin derivatives for antiviral drugs, in particular, to the prevention of and the therapy against AIDS (Acquired Immune Deficiency Syndrome) virus.
The number of patients with AIDS has abruptly increased recently, centering on the U.S.A. and Africa, and currently it amounts to about fifty thousand persons, the virus carriers existence being about a hundred times as many, all over the world. It is said that almost all virus carriers come down with the disease within five years and the death rate reaches about 100%. AIDS causes the immune system of living bodies to collapse through the fact that the AIDS virus infects the helper T cells governing the immune system and destroys them.
As a result, persons succumb to opportunistic infections, malignant tumors or the like, and die with this disease.
To date, nucleic acid-based AZT (azidothymidine) alone is approved as a therapeutic drug for use against AIDS. The AZT, however, cannot be used for a long term, due to its intensive side effects (anemia, etc.).
On the other hand, lignin exists abundantly in nature, after cellulose, and is contained in almost all plants, and has been ingested by human beings as a part of their food.
Recently, the physiological effects (for intestinal disorders, etc.) thereof are attracting attention as a vegetable fiber.
Moreover, the production of lignin derivatives is centered on spent liquor in the pulp and paper industry. The potential thereof as a medicinal drug, however, has been hardly investigated and merely its antitumoral property is known.
Thus, the physiological effects of ligninsulfonic acid and other lignin derivatives and, in particular, its antiviral 3~ effect against NDV (Newcastle Disease Virus) belonging to the 1 33525q -paramyxovirus family and RSV (Rous Sarcoma Virus) and HIV
(Human Immunodeficiency Virus) belonging to the retrovirus family, to which the AIDS virus also belongs, has been investigated, leading to the completion of the invention.
SUMMARY OF THE INVENTION
The gist of the invention lies in a composition for anti-AIDS viral and other antiviral medicines having spent liquor from sulfite pulping and/or processed products as the major constituent.
DETAILED DESCRIPTION OF THE INVENTION
First, the antiviral activity of sulfite spent liquor was determined to find that activity is exhibited at about 1.5 mg/ml against NDV and at about 100 ,ug/ml against RSV. Next, the sulfite spent liquor was fractionated through ultrafilters (UK type) with fractional molecular weights of 10,000 and 1,000. The quantities of sugars, ashes and ligninsulfonic acid in each fraction were determined and the antiviral activity was tested to obtain the results as shown in Table 1 below.
3~
,, ~
.J ~ - 2 -1 33525q ~ E
C~ JJ
~0 :> E
.~ .~ ~
,-- ~ ~ o ~ o r O O O C~
.
~ :~ E
~ L~
:Z ,1~0 ~ E
.~ .,~
o U~
C C~
'I: ~ ~ O
.
C) ,~
o .~
.,_ , ~q aJ o~ ~
O
D u~ ~o ~ o U~ ~-0 G . ~ .~ n v E~ E
cn o `J O ~ ~ O c~
. .
(J
J~ v o JJ ~-- 3 o ~C o o~ ~ o C O
3 ~
0 0 cd C~ ~a ,~ OQ
JJ o o ~ o E
~ E E ca E
aJ o o o ~ o ~ o ~ o~
' ~ c~ O c~ o a~ cJ
~: o ~ o oo ^ o n ~ o~ o 1 33525'~
It has been found that the substance which exhibits the antiviral activity resides in ligninsulfonic acid and, in particular, the fraction which exhibits high activity has a molecular weight on the high side. This fraction also exhibited potent antiviral activity against HIV. However, this fact does not deny the existence of antivirus-active substances, except ligninsulfonic acid, in sulfite spent liquor.
The methods of testing for antiviral activity are set out below.
In a test for anti-NDV activity, primary culture cells CEF (Chick Embryo Fibroblast) were proliferated on a plate with 96 holes and infected with NDV. Then, after 30 minutes, progressively diluted samples were added and, 24 hours later, the concentration needed to inhibit cell fusion caused by the virus was determined under a microscope.
In a test for anti-RSV activity, following the proliferation of said CEF on a plate with 96 holes, the CEF
was infected with RSV. After 1 hour, progressively diluted samples were added and, 5 days later, the concentration required to inhibit the transformation caused by the virus was determined under a microscope.
For the anti-HIV test, MT-4 (human T cells infected by HTLV-1) and HTLV-IIIb were used as the cells and virus, respectively. The virus medium was prepared from the culture supernatant of Nolt 4/HIVHTLV_IIIb cells being HIV-producing cells. The titer of virus was 1 x 106 TCIDso/ml. RPMI 1640 (cont~i n ing antibiotics) was used as a medium. For the culture, equal quantities of MT-4 cells of 1 x 106 cells/ml and HTLV-IIIb of 2 x 104 TCIDso/ml were added to each well of a plate with 24 holes, which was cultured for 1 hour to allow adsorbtion of the virus. Thereafter, sample solutions diluted to various concentrations were added and, finally, the medium was added to make up the volume to 1 ml, which was cultured 3~ for 4 days in a CO2 incubator of 37 C. As the references, _ 4 -d 3 3 5 2 5 q cultures with cells not infecte by HTLV-IIIb and without the addition of sample were performed. The antiviral effect was judged by two methods; the inhibition of cell degeneration due to HIV and the inhibition of the development of HIV specific antigen onto the surface of cells. First, the cell degeneration effect was judged from the inhibition of the lethal effect on cells through the addition of sample by counting the number of living cells using the trypan blue method for the four-day culture medium, both infected and not infected by HIV. For the determination of HIV specific antigen, after reacting the cells fixed with methanol first with anti-HIV human serum for 40 minutes at 37 C, FITC-labelled anti-human-IgG was added and allowed to react for 40 minutes at 37 C and then the number of fluorescently labelled cells were counted using a fluorescent microscope.
Next, the antiviral activity was determined for various lignin derivatives, also.
Results are shown in Table 2.
The methods of preparing samples in said table are as follows:
3~
1 33525q o Sodium ligninsulfonate Produced by treating calcium ligninsulfonate with sodium sulfate to exchange the base.
o Calcium ligninsulfonate Produced by cooking red pine with cooking liquor of calcium sulfite (CaS03).
o Magnesium ligninsulfona~e Produced by cooking red pine with cooking liquor of magnesium sulfite (MgS03).
o Kraft lignin Produced by kraft pulping of red pine to field bleached kraft pulp ~residual lignin in pulp : 2.0 %).
Composition of kraft spent liquor (inorganics 6.2 %, sugars 2.8 %, lignin 6.0 %).
o Dioxane ligin Extracted from wood flour (spruce) treated with alcohol-benzene by heating for 2 hours at 175 C in a mixed liquor of dioxane-water (1 : l) according to the method of Sakakibara et al.
The yield was about 45 %.
o Thioglycolic acid lignin Prepared according to Brauns et al in a way that degreased wood flour (birch) was added to 2 mixed liquor of thio~lycolic acid with 2N hydrochloric acid to boil for 7 hours, the mass was then separated by filtration and, after washing with water and with ethanol, the residue was extracted with 2 % sodium -hydroxide. The lignin was recovered after being precipitated with hydrochloric acid.
o Sulfomethylated product of kraft lignin Prepared in a way that Na2SO3 (10 to 20 % based on kraft lignin) and then HCHO (equimols to Na2SO3) were added to a slurry (about 25 ~) of kraft lignin to treat for 1 to 2 hours at 60 to 80 C and, after treating further for 2 to 3 hours at 130 to 150 C, cooling and drying.
Table 2 Sample Anti-NDV activity Anti-RSV activity Sodium ligninsulfonate 0.3 mg/ml 0.03 mg/ml Calcium ligninsulfonate 0.4 0,04 Magnesium ligninsulfonate 0.2 0.03 Kraft lignin 1.2 0.1 Dioxane lignin 1.5 0.2 Th~oglycolic acid lignin 0.8 0.1 Sulfomethylated product 0 5 0 07 of kraft lignin -As noted above, the antiviral activity was recognized with all lignin derivatives listed in the table and thereamong ligninsulfonic acids were proved to have a very potent antiviral effect. The useful lignin derivatives are not confined to those in the table and any one currently known will serve.
In the following, the invention will be exemplified, based on the examples, but the invention is not confined to these.
Example 1 Using a dialyzing membrane, 100 ml of sulfite spent liquor shown in Table 1 was dialyzed for 4 days against tap water and for 3 days against deionized water in batch. The liquor, having finish-ed the dialysis,was concentrated to about 30 ml with arotary evapo-rator and then freeze-dried to obtain about 3.5 g of fraction rich in ligninsulfonic acid. Both reducing sugar and ash in this fraction decreased to about one tenth compared with those of the original sulfite spent liquor. When determining the anti-NDV and anti-RSV activities, this fraction exhibited the effect at 0.5 mg/ml and 0.04 mg/ml, respectively.
Example 2 After 100 ml of kraft spent liquor shown in Table 2 was adjusted to pH 3.0 to precipitate the portion of kraft lignin, this was centrifuged (10,000 rpm) to collect the precipitated fraction. Then, this was converted to powder by drying under reduced pressure to obtain about 4.0 g of fraction rich in kraft lignin. Suspending this into deionized water, lN NaOH was added to completely dissolve and a solution with a final concentration of 1 % was prepared. When determining the anti-NDV and anti-RSV activities using said kraft lignin solution, the effect was seen at 0.8 mg/ml and 0.07 mg/ml, respectively, in terms of solids.
Example 3 Using a portion of sulfite spent liquor with a fractional molecular weight of over 10,000 shown in Table 1, the anti-HIV
activity was determined. Results are shown in Table 3 -- 1 33525~
Table 3 Concentration Number of living Number of living Positivity of of sample cells when not in- cells when infected HIV specific fected by HIV by HIV antigen 5500 ~g/ml 1.36 x 106/ml 1.08 x 106/ml 0 %
250 1.46 1.41 0 125 1.57 1.45 0 63 1.53 1.61 0 32 1.58 1.66 0 16 1.56 1.53 0 8 1.58 1.5~ 0 4 1.59 0.96 20 0 1.61 0.21 90 2~ From the results above, it became clear that the anti-HIV
activity of the fraction of sulfite spent liquor with a molecular weight of over 10,000 inhibited completely both the cell degenera-tion due to virus and the development of HIV specific antigen at a very low concentration of 8 ~g/ml and the toxicity against cells was only generated slightly at a high concentration of 500 ~g/ml proving the fraction to be an antiviral agent with very high SI (Selective Index).
Claims (8)
1. A composition for anti-AIDS viral and other anti-retroviral medicines comprising spent liquor from sulfite pulping and/or processed products thereof as a major constituent.
2. The composition according to claim 1, wherein the sulfite spent liquor is fractionated and has the fraction with a molecular weight of not less than about 5,000 as a major component.
3. The use of spent liquor from sulfite pulping and/or processed products thereof for the treatment of AIDS viral infections and other retroviral infections.
4. A composition for anti-AIDS viral and other anti-retroviral medicines comprising lignin derivatives as the major constituent.
5. The composition according to claim 4, wherein the legnin derivatives are obtained from the lignin in woods or herbs as a raw material.
6. A composition for anti-AIDS viral and other anti-retroviral medicines having non-ligneous components in woods and/or herbs and/or derivative thereof as majorconstituents.
7. The composition of claim 2 wherein the fractionation is carried out by ultrafiltration.
8. The composition of claim 2 wherein the fractionation is carried out by gel filtration.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1082691A JP2602715B2 (en) | 1988-04-12 | 1989-03-31 | Antiviral pharmaceutical composition |
| JPHEI1-82691/89 | 1989-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1335259C true CA1335259C (en) | 1995-04-18 |
Family
ID=13781439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 612816 Expired - Fee Related CA1335259C (en) | 1989-03-31 | 1989-09-25 | Composition of spent liquor from pulping process for antiviral medicine |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1335259C (en) |
| DE (1) | DE4010368A1 (en) |
| FR (1) | FR2645024B1 (en) |
| GB (1) | GB2229919B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03120223A (en) * | 1989-10-04 | 1991-05-22 | Sanyo Kokusaku Pulp Co Ltd | Composition for antiviral drug |
| DE4017091A1 (en) * | 1990-05-27 | 1991-11-28 | Walter Dr Mach | MOLECULE COMPOSITION SYSTEM FOR THE CONTRA-ESCALATIVE THERAPY OF VIRAL INFECTIOUS DISEASES |
| CA2122439A1 (en) * | 1993-11-19 | 1995-05-20 | Michio Tani | Pharmaceutical composition for treating aids |
| DE4415087A1 (en) * | 1994-04-29 | 1995-11-09 | Zschiegner Hans Joachim Dr | Lignin based compsn. for use in balneotherapy, cosmetics etc |
| RU2141335C1 (en) * | 1998-12-30 | 1999-11-20 | Общество с ограниченной ответственностью "Лигфарм" | Antitumor agent "olipifat" and method of its preparing |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE718438A (en) * | 1967-08-23 | 1968-12-31 | ||
| IL38003A (en) * | 1970-11-16 | 1974-06-30 | Robins Co Inc A H | Anti-inflammatory agents coprecipitated with lignosulfonates |
| US3914433A (en) * | 1971-07-30 | 1975-10-21 | Robins Co Inc A H | Method of relieving the discomfort of pharyngitis |
| JPS5213583A (en) * | 1975-07-22 | 1977-02-01 | Sanyo Kokusaku Pulp Co Ltd | Preparation of antitumorous agent |
| US4185097A (en) * | 1978-01-09 | 1980-01-22 | A. H. Robins Company, Inc. | Method of combating Herpes simplex viruses with lignosulfonates |
| SU1251904A1 (en) * | 1984-03-07 | 1986-08-23 | Центральный Научно-Исследовательский Институт Стоматологии Мз Ссср | Composition for mineralization of teeth |
| EP0293826A3 (en) * | 1987-06-02 | 1989-05-10 | Stichting REGA V.Z.W. | Therapeutic and prophylactic application of sulfated polysaccharides against aids |
| US4985249A (en) * | 1987-06-26 | 1991-01-15 | Hiroshi Sakagami | Anti-HIV agents |
| US4988799A (en) * | 1987-08-11 | 1991-01-29 | Daishowa Chemicals Inc. | Lignosulfonate based pharmacologic agent with anti-coagulant and anti-thrombotic activity |
| DE3866513D1 (en) * | 1987-11-06 | 1992-01-09 | Neth Rolf Dietmar | MEDICINE WITH A COMPONENT CONTAINING A POLYSACCHARIDE FROM THUJA PLANTS AS AN ACTIVE ACTIVE SUBSTANCE. |
-
1989
- 1989-09-25 CA CA 612816 patent/CA1335259C/en not_active Expired - Fee Related
- 1989-10-10 GB GB8922752A patent/GB2229919B/en not_active Expired - Fee Related
- 1989-10-24 FR FR8913909A patent/FR2645024B1/en not_active Expired - Fee Related
-
1990
- 1990-03-30 DE DE19904010368 patent/DE4010368A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE4010368C2 (en) | 1992-07-02 |
| GB2229919A (en) | 1990-10-10 |
| FR2645024B1 (en) | 1993-10-29 |
| DE4010368A1 (en) | 1990-10-04 |
| GB2229919B (en) | 1993-04-14 |
| GB8922752D0 (en) | 1989-11-22 |
| FR2645024A1 (en) | 1990-10-05 |
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