US3608079A - Thiouracil-carboxylic acids for treatment of viruses - Google Patents
Thiouracil-carboxylic acids for treatment of viruses Download PDFInfo
- Publication number
- US3608079A US3608079A US722183A US3608079DA US3608079A US 3608079 A US3608079 A US 3608079A US 722183 A US722183 A US 722183A US 3608079D A US3608079D A US 3608079DA US 3608079 A US3608079 A US 3608079A
- Authority
- US
- United States
- Prior art keywords
- carboxylic acid
- thiouracil
- component
- uracil
- dose
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 241000700605 Viruses Species 0.000 title claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 21
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 20
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 20
- ISOQUWRYYNKKGX-UHFFFAOYSA-N 4-oxo-2-sulfanylidene-1h-pyrimidine-6-carboxylic acid Chemical compound OC(=O)C1=CC(O)=NC(S)=N1 ISOQUWRYYNKKGX-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 206010059313 Anogenital warts Diseases 0.000 claims abstract description 7
- 208000000907 Condylomata Acuminata Diseases 0.000 claims abstract description 7
- 208000009889 Herpes Simplex Diseases 0.000 claims abstract description 7
- 208000007514 Herpes zoster Diseases 0.000 claims abstract description 7
- 208000000260 Warts Diseases 0.000 claims abstract description 7
- 230000000694 effects Effects 0.000 claims abstract description 7
- 208000008588 molluscum contagiosum Diseases 0.000 claims abstract description 7
- 201000010153 skin papilloma Diseases 0.000 claims abstract description 7
- 229930182817 methionine Natural products 0.000 claims description 14
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 abstract description 21
- 235000006109 methionine Nutrition 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000003708 ampul Substances 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 235000016709 nutrition Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- ZXYAAVBXHKCJJB-UHFFFAOYSA-N uracil-5-carboxylic acid Chemical compound OC(=O)C1=CNC(=O)NC1=O ZXYAAVBXHKCJJB-UHFFFAOYSA-N 0.000 description 5
- -1 alkali metal salts Chemical class 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 239000004381 Choline salt Substances 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000019417 choline salt Nutrition 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 210000004698 lymphocyte Anatomy 0.000 description 3
- 239000012022 methylating agents Substances 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CXJHFMMYWITJGH-YFKPBYRVSA-N (2S)-2-(methoxyamino)-4-methylsulfanylbutanoic acid Chemical compound CON[C@@H](CCSC)C(=O)O CXJHFMMYWITJGH-YFKPBYRVSA-N 0.000 description 2
- KFSJYZYQSZKRRQ-BYPYZUCNSA-N (2s)-2-(hydroxyamino)-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@H](NO)C(O)=O KFSJYZYQSZKRRQ-BYPYZUCNSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000004470 DL Methionine Substances 0.000 description 1
- 208000003098 Ganglion Cysts Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 229940073801 methionine 250 mg Drugs 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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
Definitions
- compositions comprising 2- thioui'acil-4-carboxylic acid and uracil-4-carboxylic acid and their nontoxic salts or lower alkyl esters. These compositions are effective in providing a nonspecific activity against virus warts, Molluscum contagiosum, Condylomata acuminata, Herpes simplex, and Herpes zoster.
- THIOURACIL-CARBOXYLIC ACIDS FOR TREATMENT OF VIRUSES SUMMARY OF THE INVENTION The present invention is based upon the discovery that a useful chemotherapeutic effect in human beings can be obtained by the administration of a thiouracil-carboxylic acid, preferably 2-thiouracil-4-carboxylic acid which is the compound of formula
- pharmaceutical or nutritional compositions for human use comprising as active ingredient a thiouracil-carboxylic acid, or a nontoxic salt or alkyl ester of a thiouracilcarboxylic acid, together with one or more carriers or excipients as herein defined.
- the thiocuracil-carboxylic acid used in the compositions according to the invention is preferably a 2'thiouracil-carboxylic acid.
- 2-Thiouracil-4-carboxylic acid and salts and alkyl esters thereof are particularly preferred active ingredients.
- non-toxic as used herein in relation to the salts of thiouracil-carboxylic acids we mean such salts the cationic portions of which are physiologically compatible in the dosages used.
- Preferred salts include alkali metal salts such as the sodium and potassium salts, and ammonium and quaternary ammonium salts such as for example the choline salt.
- Preferred alkyl esters are esters in which the alkyl group is a lower alkyl group containing from one to five carbon atoms, especially a methyl or ethyl group.
- the expression carriers or excipients as used herein means any solid or liquid carrier or excipient suitable for the formulation of pharmaceutical and nutritional compositions, but does not include water or solvents alone which together with the other component or components of the composition in the concentrations in which they are present give rise to mere known solutions.
- compositions according to the invention may be presented in a form suitable for oral, rectal or parenteral administration.
- compositions for oral administration may be solid or liquid and may take the form of capsules, tablets, coated tablets, cachets, granules, powders, syrups, suspensions, etc., such compositions including carriers or excipients conveniently used in the pharmaceutical art.
- Suitable tabletting excipients include lactose, potato and maize starches, talc, gelatine, and stearic and silicic acids, magnesium stearate and polyvinylpyrrolidone.
- the carrier or excipient may be a sterile, parenterally acceptable liquid, e.g. pyrogen-free water or an aqueous solution of polyvinylpyrrolidone, or a parenterally acceptable oil, e.g. arachis oil, contained in ampuls.
- a parenterally acceptable liquid e.g. pyrogen-free water or an aqueous solution of polyvinylpyrrolidone
- a parenterally acceptable oil e.g. arachis oil
- the carrier may comprise a suppository base, e.g., cocoa butter or other glyceride.
- the carrier may be provided by a foodstuff such as for example milk powder.
- compositions may be formulated as dosage units, each unit being adapted to supply a fixed dose of active ingredient.
- Tablets, coated tablets, capsules, pills, cachets, ampuls and suppositories are examples of preferred dosage unit forms according to the invention, which con.- veniently contain from 0.1 to 100 mg., preferably 0.5 to mg., of active ingredient.
- compositions according to the invention as hereinbefore defined in general assists in providing a nonspecific activity against virus warts and diseases such as for example Molluscum contagiosum, condylomata acuminata, Herpes simplex and Herpes zoster. it has been found that an improved eflect is generally obtained if the thiouracilcarboxylic acid component is administered together with a uracil-carboxylic acid or a nontoxic salt or alkyl ester thereof.
- the uracil-carboxylic acid is preferably uracil-4-caryoxylic acid but may also for example be provided by uracil-S-carboxylic acid, uracil-4,5- dicarboxylic acid and nontoxic salts and alkyl esters of such acids.
- preferred compositions according to the invention contain a uracil-carboxylic acid, the particularly preferred ratio by weight of the thiouracilcarboxylic acid (or nontoxic salt or alkyl ester thereof) to uracil-carboxylic acid (or nontoxic salt or alkyl ester thereof) being from 1:1 to l:50, by weight.
- thiouracil-carboxylic acid component is administered together with methionine or a biological equivalent thereof such as for example hydroxymethionine or methoxy-methionine.
- methionine or other biological methylating agent that is an agent capable of effecting the introduction of methyl groups under biological conditions.
- the biological methylating agents may for example be physiological methyl donors and methionine, hydroxy-methionine and methoxymethionine are of course well-known methyl donors. Other such donors include choline and S-methyl-tetrahydrofolic acid.
- methyl donors possess a comparatively labile methyl group. Such a methyl group will generally be attached to a sulfur atom (as in methionine) or a nitrogen atom (as in choline).
- compositions according to the invention contain methionine or other biological methylating agent, the ratio by weight of the thiouracil carboxylic acid (or nontoxic salt or alkyl ester thereof) to biological methylating agent being from 1:10 to l: 200, advantageously about 1: 100, by weight.
- a pharmaceutical or nutritional composition which comprises a thiouracilcarboxylic acid or a nontoxic salt or alkyl ester of a thiouracil-carboxylic acid, together with methionine (or other biologicalmethylating agent and/or a uracil-carboylic acid (or a nontoxic salt or alkyl ester thereof).
- compositions according to the invention in general assists in providing a nonspecific activity against virus warts and diseases such as for example Molluscum contagiosum, Condylomata acuminata, Herpes simplex and Herpes zoster.
- Compositions containing for example 2-thiouracil-4- carboxylic acid, uracil-4-carboxylic acid and methionine e.g. in a ratio by weight of about 12:10: 100, stimulate the production of active lymphocytes.
- compositions according to the invention containing for example 2-thiouracil-4-carboxylic acid, uracil-4-carboxylic acid and methionine in a ratio by weight of about 1:10:100 have been found in these circumstances to promote a new formation of lymphocytes and thus to resuscitate the defensive mechanism of the body.
- composition according to the invention containing 2- thiouracil-4-carboxylic acid, uracil-4-carboxylic acid and methioine in a ratio by weight of about 1:10:100 is useful in the treatment of virus warts and diseases such as for example Molluscum contagiosum, Condylomata acuminata, Herpes simplex and Herpes zoster. It also leads to an increase in the erythrocytes in the blood.
- thiouracil-carboxylic acids and nontoxic salts and alkyl esters thereof may be antimetabolites of uracil which are taken up by virus (pl.) and which stunt or inhibit the growth thereof.
- Thiouracil-carboxylic acids are substances having generally low toxicity.
- 2-thiouracil- 4-carboxylic acid has been administered orally to rats at a dosage of 0.5 g./kg. of body weight for over 90 days without any toxic effects.
- thiouracil-4-carboxylic acid has no influence on the activity of the thyroid gland and so it efiects neither the oxygen consumption of the body nor the basal metabolic rate.
- the thiouracil-carboxylic acid (or nontoxic salt or alkyl ester thereof) is preferably administered at a dose of about 1 to 500 mg. advantageously to 50 mg., per day.
- a uracil-carboxylic acid or nontoxic salt or alkyl ester thereof
- the latter is preferably administered at a dosage of about 50 mg. to l l g., advantageously 100 to 500 mg., per day.
- methionine or a biological equivalent thereof
- the latter is preferably administered at a dosage of about 1 to 10 g., advantageously 3 to 5 g., per day.
- the recommended dose is 4 or 5 capsules per day.
- EXAMPLE 2 Ampuls are prepared each of which contains the following: 30 mg. of the choline salt of Z-thiouracil-4carboxylic acid 200 mg. uracil-4-carboxylic acid, choline salt 250 mg. dl-methionine The ingredients are filled into dry ampuls. In use, one gives 15 ml. sterile, physiological salt solution in the ampul and immediately after dissolution of the active ingredients, the ampul solution is injected (preferably subcutaneoysly).
- EXAMPLE 3 Dietetic preparation mg. 2-thiouracil-4-carboxylic acid are homogeneously mixed in 100 g. milk powder. This mild powder is if desired made aromatic. In use, 20 g. of this powder may be dissolved in a cup of hot water and given one to two times daily.
- a pharmaceutical composition which comprises as active ingredients:
- uracil-4-carboxylic acid or a nontoxic salt or lower alkyl ester thereof;
- component (a) to component (b) wherein the ratio by weight of component (a) to component (b) is about 1:10 and the weight of (a) per dosage unit is from 0.1 mg. to 100 mg.
- a method of providing a nonspecific activity against virus warts, Molluscum contagiosum, Condylomata acuminata, Herpes simplex, and Herpes zoster in humans which comprises administering thereto a pharmaceutical composition which comprises as active ingredients:
- component (a) in an amount sufficient to provide a dose of about I to 500 mg. per day of component (a), and a dose of about 50 mg. to l gm. per day of component (b), wherein the ratio by weight of component (a) to component (b) is from 1:1 to l: 50.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08102/67A GB1193192A (en) | 1967-04-19 | 1967-04-19 | Pharmaceutical Compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3608079A true US3608079A (en) | 1971-09-21 |
Family
ID=10106685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US722183A Expired - Lifetime US3608079A (en) | 1967-04-19 | 1968-04-18 | Thiouracil-carboxylic acids for treatment of viruses |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3608079A (en:Method) |
| BE (1) | BE713858A (en:Method) |
| DE (1) | DE1767275C3 (en:Method) |
| FR (1) | FR7478M (en:Method) |
| GB (1) | GB1193192A (en:Method) |
| NL (1) | NL140733B (en:Method) |
-
1967
- 1967-04-19 GB GB08102/67A patent/GB1193192A/en not_active Expired
-
1968
- 1968-04-18 US US722183A patent/US3608079A/en not_active Expired - Lifetime
- 1968-04-18 BE BE713858D patent/BE713858A/xx not_active IP Right Cessation
- 1968-04-18 NL NL686805514A patent/NL140733B/xx unknown
- 1968-04-19 FR FR148634A patent/FR7478M/fr not_active Expired
- 1968-04-19 DE DE1767275A patent/DE1767275C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE713858A (en:Method) | 1968-10-18 |
| GB1193192A (en) | 1970-05-28 |
| NL6805514A (en:Method) | 1968-10-21 |
| NL140733B (nl) | 1974-01-15 |
| FR7478M (en:Method) | 1969-12-01 |
| DE1767275C3 (de) | 1979-06-21 |
| DE1767275A1 (de) | 1972-04-20 |
| DE1767275B2 (de) | 1978-10-26 |
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