US3070498A - Nitrothiazole-hydroxyquinoline compositions - Google Patents
Nitrothiazole-hydroxyquinoline compositions Download PDFInfo
- Publication number
- US3070498A US3070498A US55149A US5514960A US3070498A US 3070498 A US3070498 A US 3070498A US 55149 A US55149 A US 55149A US 5514960 A US5514960 A US 5514960A US 3070498 A US3070498 A US 3070498A
- Authority
- US
- United States
- Prior art keywords
- hydroxyquinoline
- nitrothiazole
- composition
- compositions
- concentration
- 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
- 239000000203 mixture Substances 0.000 title claims description 34
- LFXQWIYCTNAXBV-UHFFFAOYSA-N 2-nitro-1,3-thiazole 1H-quinolin-2-one Chemical compound OC1=NC2=CC=CC=C2C=C1.[N+](=O)([O-])C=1SC=CN1 LFXQWIYCTNAXBV-UHFFFAOYSA-N 0.000 title 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 21
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 19
- 229960003540 oxyquinoline Drugs 0.000 claims description 19
- ALNUOSXDMYFQNQ-UHFFFAOYSA-N 2-nitro-1,3-thiazole Chemical class [O-][N+](=O)C1=NC=CS1 ALNUOSXDMYFQNQ-UHFFFAOYSA-N 0.000 claims description 15
- QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 claims description 3
- 238000012360 testing method Methods 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 244000005700 microbiome Species 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
- -1 compounds Sulfonamides Halogens Chemical class 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 7
- SRAGSPNJULICDG-UHFFFAOYSA-N 1-[4-(5-nitro-1,3-thiazol-2-yl)piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC=C([N+]([O-])=O)S1 SRAGSPNJULICDG-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- 241000224527 Trichomonas vaginalis Species 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 235000015110 jellies Nutrition 0.000 description 4
- 239000008274 jelly Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 231100000344 non-irritating Toxicity 0.000 description 4
- 239000001509 sodium citrate Substances 0.000 description 4
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 4
- 229940044950 vaginal gel Drugs 0.000 description 4
- 239000000286 vaginal jelly Substances 0.000 description 4
- 229940044977 vaginal tablet Drugs 0.000 description 4
- 239000000003 vaginal tablet Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 229940044959 vaginal cream Drugs 0.000 description 3
- 239000000522 vaginal cream Substances 0.000 description 3
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 2
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 2
- 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 2
- RDXLYGJSWZYTFJ-UHFFFAOYSA-N Niridazole Chemical compound S1C([N+](=O)[O-])=CN=C1N1C(=O)NCC1 RDXLYGJSWZYTFJ-UHFFFAOYSA-N 0.000 description 2
- 241001058196 Tritrichomonas foetus Species 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229960005130 niridazole Drugs 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 108010050327 trypticase-soy broth Proteins 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- XWBADQOPXPRKBX-FMIVXFBMSA-N 1-n,1-n-diethyl-4-n-[6-methoxy-2-[(e)-2-(4-nitrophenyl)ethenyl]quinolin-4-yl]pentane-1,4-diamine Chemical compound N=1C2=CC=C(OC)C=C2C(NC(C)CCCN(CC)CC)=CC=1\C=C\C1=CC=C([N+]([O-])=O)C=C1 XWBADQOPXPRKBX-FMIVXFBMSA-N 0.000 description 1
- QAQPKTNTSMCSPL-UHFFFAOYSA-N 2-(2-nitropiperazin-1-yl)-1,3-thiazole Chemical class [N+](=O)([O-])C1N(CCNC1)C=1SC=CN1 QAQPKTNTSMCSPL-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000011360 adjunctive therapy Methods 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000001998 anti-microbiological effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003716 antitrichomonal agent Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000005002 female reproductive tract Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 201000005630 leukorrhea Diseases 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 206010046901 vaginal discharge Diseases 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
Definitions
- Leukorrhea or an abnormal discharge from the female genital tract is one of the chief gynecologic complaints. It may arise from a number of causes.
- One of the most common and difiicult to treat is an infection with Trichomonas vaginalis.
- Various agents have been devised to help manage this problem. Those in common use may be divided into groups according to the active principle as follows:
- the accepted method of treating trichomonal infection is by the topical application of a trichomonacide by suppository, vaginal tablet, jelly or insutllation. Acidification of the vaginal tract by vinegar douches is common adjunctive therapy.
- O-N H II O2NO C-X wherein X is selected from the group consisting of NH NH-CO-CH NH-CO-NH-C H and CHz-CHn N' Nz CHg-6Hn in which Z is selected from the group consisting of H; lower alkyl; hydroxy-lower-alkyl; carbalkoxy; acyl derived from alkanoic, haloalkanoic, aralkanoic and aryl acids; formyl; and formamido.
- Trichomonas vaginalis strain 1 Kupferberg, was grown in simplified trypticase serum broth, pH 6.0.
- Trichomonas foetus, strain BR was grown in simplified trypticase serum broth, pH 7.0; Trichomonal cultures were incubated at 37 C. for 48 hours after which time they reached a cell density of l to 3 10 cells per ml. Graded amounts of the drug under test were added to tubes of S.T.S. to give final concentrations of from 1000 p.p.m. to 0.5 ppm. To each of these tubes was added 0.5 ml. from the 48-hour seed cultures.
- Drug-free solvent controls (propylene glycol for the nitrothiazoles, ethanol for 8-hydroxyquinoline or iodochlorohyd'roxyquinoline) were similarly inoculated. All tubes were incubated at 37 C. for 48 hours; the presence or absence of trichomonads was then determined micro,- scopically.
- compositions as it is used can be in the form either of a jelly, a cream, or in some cases a suppository-type tablet.
- the composition consists, not only of the two active ingredients in a proportion found to be eificacious in use by clinical tests, but also of a suitable base material or carrier of an appropriate nature in view of the class of composition to be prepared and which is therapeutically acceptable in use, bland and non-irritating. Additional materials in small amounts can also be employed for controlling the pH of the composition, so as to bring the pH value slightly on the acid side of neutral. Examples of suitable compositions of three types are as follows:
- Example I.Vaginal Cream The base material used in this example is an oil-in-w rter emulsion, with which the active ingredients are present in an amount aggregating not over about of the total weight.
- the particular ingredients given in one specific composition which has been prepared is typical of a petrolaturn (as an example of an oil-in-water type) emul sion usable for this purpose.
- Example 2.--Vaginal Jelly The base material or carrier in this instance is a suitable jelly, made from a jelling agent such as methyl cellulose, starch, vegetable gums and the like, and water, this je.lytype base being combined with the active ingredients and with minor amounts of pH controlling ingredients in the formulation of the composition as a whole. Further, in the composition which is specifically given hereinafter, a substantial amount of glycerine is used as a watermiscible solvent material assisting in the formulation of a jelly of a desired consistency as a carrier or base for the active ingredients.
- a jelling agent such as methyl cellulose, starch, vegetable gums and the like
- Example 3.Vaginal Tablet Ingredient Percent by weight Lactose 85.0 Sodium citrate 0.1 Citric acid 0.4 Magnesium stearate 1.0 1-acetyl-4-(S-nitro-Z-thiazolyl) piperazine 5.0 8-hydroxyquinoline 1.25 Starch 7.25
- each of the two principal ingredients ot the composition shall be present in a substantial amount, which amount may be half or less that concentration which would be required if the compound in question were to be used alone as proven by the in vitro tests hereiuabove set forth.
- the nitrothiazolyl piperazine compound is used in a weight percent, which is about four times that of the hydroxyquinoline compound. This proportion is not intended as limiting upon the ratio in which these two active ingredients may be used with respect to each other, but rather such ratio is uite wide in range.
- compositions of the present invention have been effected, in most instances, with one or another of the compositions above given, at least as to the ratio of concentration of the two active ingredients and have used the specific active ingredients set out in these particular compositions, ie. S-hydroxyquinoline and 1-acetyl-4-(5-nitro-2-thiazolyl) piperazine.
- composition consisting essentially of (A) a material selected from the group consisting of S-hydroxyquinoline and 5-chloro-7-iodo-8-hydroxyquinoline, and (B) a nitrothiazole derivative having the formula:
- X is selected from the group consisting of NH NH-CO -CH NH-CO-NH-C H and in which Z is selected from the group consisting of H; lower alkyl; hydroxy-lower-alkyl; carbalkoxy; acyl derived from alkanoic, haloalkanoic, aralkanoic and aryl acids; formyl; and formamido; said materials (A) and (B) each being present in the composition in a substantial amount.
- composition of claim 1 in which the weight ratio of said material (A) to said material (B) is in the range of about 1:10 to 10:1.
- composition of claim 1 in which said material (A) is 8-hydroxyquinoline; in which X is and in which Z is as defined in claim 1.
- composition consisting essentially of (A) 8-hydroxyquinoline and (B) a compound having the formula:
- composition useful for the treatment of trichomonal infections the essential active ingredients of which consist of 8-hydroxyquinoline and 1-acety1-4-(5-nitro-2- thiazolyl) piperazine.
- composition consisting essentially of 8-hydroxyquinoline and 1-acetyl-4-(5-nitro-2-thiazolyl) piperazine in which these materials are present in the proportion of about one part by weight of the 8-hydroxyquinoline to four parts by weight of the piperazine compound aforesaid.
- a vaginal cream consisting essentially of 8-hydroxyquinoline and 1-acetyl-4-(5-nitro-2-thiazolyl) piperazine as essential active ingredients; and an oil-in-water emulsion carrier base, which is therapeutically acceptable, bland and non-irritating.
- a vaginal cream consisting essentially of the following materials in the proportion by weight given:
- a vaginal jelly consisting essentially of 8-hydroxyquinoline and 1-acety1-4-(5-nitro-2-thiazolyl) piperazine as essential active ingredients; and an aqueous-jelly carrier base, which is therapeutically acceptable, bland and non-irritating.
- vaginal jelly consisting essentially of the followb (3 ing materials in the proportion by weight given:
- Methyl cellulose 400 cps.
- Glycerine 15.0
- Citric acid 0.1
- Benzoic acid 0.1
- Sodium citrate 0.2
- 1-acetyl-4-( 5-nitro-2-thiazolyl) piperazine 1.0 S-hydroxyquinoline 0.25 Distilled water to make 75.85
- a vaginal tablet consisting essentially of 8-hydroxyquinoline and l-acetyl-4-(5-nitro-2-thiazolyl) piperazine as essential active ingredients; and a solid tablet-forming carrier base, which is substantially water-soluble, therapeutically acceptable, bland and non-irritating.
- a vaginal tablet consisting essentially of the following materials in the proportion by weight given:
- X is -NH-CO-CH
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)
- Medicinal Preparation (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55149A US3070498A (en) | 1960-09-12 | 1960-09-12 | Nitrothiazole-hydroxyquinoline compositions |
| FR847895A FR817M (enrdf_load_stackoverflow) | 1960-09-12 | 1960-12-23 | |
| GB44471/60A GB899992A (en) | 1960-09-12 | 1960-12-28 | Anti-protozoal compositions comprising hydroxyquinoline and nitrothiazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55149A US3070498A (en) | 1960-09-12 | 1960-09-12 | Nitrothiazole-hydroxyquinoline compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3070498A true US3070498A (en) | 1962-12-25 |
Family
ID=21995944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US55149A Expired - Lifetime US3070498A (en) | 1960-09-12 | 1960-09-12 | Nitrothiazole-hydroxyquinoline compositions |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3070498A (enrdf_load_stackoverflow) |
| FR (1) | FR817M (enrdf_load_stackoverflow) |
| GB (1) | GB899992A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060154874A1 (en) * | 2003-06-13 | 2006-07-13 | Hansen Inge D | Treatment of symptoms associated with bacterial vaginosis |
| WO2006109069A1 (en) * | 2005-04-14 | 2006-10-19 | Aq+Plc | Use of a metal ion chelating agent for the treatment of animal and human parasites |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2675389A (en) * | 1952-01-09 | 1954-04-13 | Geza S Delmar | Arsanilate salts of hydroxyquinolines |
| CA524353A (en) * | 1956-04-24 | The Wellcome Foundation Limited | Antitrichomonal pessary | |
| CA558019A (en) * | 1958-05-27 | Merck And Co. Inc. | Therapeutic composition containing 2-amino-5-nitrothiazole |
-
1960
- 1960-09-12 US US55149A patent/US3070498A/en not_active Expired - Lifetime
- 1960-12-23 FR FR847895A patent/FR817M/fr active Active
- 1960-12-28 GB GB44471/60A patent/GB899992A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA524353A (en) * | 1956-04-24 | The Wellcome Foundation Limited | Antitrichomonal pessary | |
| CA558019A (en) * | 1958-05-27 | Merck And Co. Inc. | Therapeutic composition containing 2-amino-5-nitrothiazole | |
| US2675389A (en) * | 1952-01-09 | 1954-04-13 | Geza S Delmar | Arsanilate salts of hydroxyquinolines |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060154874A1 (en) * | 2003-06-13 | 2006-07-13 | Hansen Inge D | Treatment of symptoms associated with bacterial vaginosis |
| US9241997B2 (en) * | 2003-06-13 | 2016-01-26 | Idh Holding Aps | Treatment of symptoms associated with bacterial vaginosis |
| WO2006109069A1 (en) * | 2005-04-14 | 2006-10-19 | Aq+Plc | Use of a metal ion chelating agent for the treatment of animal and human parasites |
Also Published As
| Publication number | Publication date |
|---|---|
| GB899992A (en) | 1962-06-27 |
| FR817M (enrdf_load_stackoverflow) | 1961-09-18 |
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