US3085935A - Method for the elimination of nematode infestations - Google Patents
Method for the elimination of nematode infestations Download PDFInfo
- Publication number
- US3085935A US3085935A US104798A US10479861A US3085935A US 3085935 A US3085935 A US 3085935A US 104798 A US104798 A US 104798A US 10479861 A US10479861 A US 10479861A US 3085935 A US3085935 A US 3085935A
- Authority
- US
- United States
- Prior art keywords
- infestations
- elimination
- host
- worms
- intestinal tract
- 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
- 206010061217 Infestation Diseases 0.000 title claims description 10
- 241000244206 Nematoda Species 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 230000008030 elimination Effects 0.000 title 1
- 238000003379 elimination reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 10
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 8
- 230000003071 parasitic effect Effects 0.000 claims description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 241000498255 Enterobius vermicularis Species 0.000 description 5
- -1 al Species 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
- 241001465677 Ancylostomatoidea Species 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 206010014881 enterobiasis Diseases 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 244000045947 parasite Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 229940006461 iodide ion Drugs 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
- HLNJFEXZDGURGZ-UHFFFAOYSA-M 1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1 HLNJFEXZDGURGZ-UHFFFAOYSA-M 0.000 description 1
- UKUBBJHXVBDEEQ-UHFFFAOYSA-N 2,6-bis[2-(4-pyrrolidin-1-ylphenyl)ethenyl]pyridine Chemical compound C1CCCN1C(C=C1)=CC=C1C=CC1=CC=CC(C=CC=2C=CC(=CC=2)N2CCCC2)=N1 UKUBBJHXVBDEEQ-UHFFFAOYSA-N 0.000 description 1
- YYBCQVWWYDZZTM-UHFFFAOYSA-N 2-[2-(4-pyrrolidin-1-ylphenyl)ethenyl]pyridine Chemical compound C1CCCN1C(C=C1)=CC=C1C=CC1=CC=CC=N1 YYBCQVWWYDZZTM-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical class CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- ILJVPSVCFVQUAD-UHFFFAOYSA-N 4-piperidin-1-ylbenzaldehyde Chemical class C1=CC(C=O)=CC=C1N1CCCCC1 ILJVPSVCFVQUAD-UHFFFAOYSA-N 0.000 description 1
- DATXHLPRESKQJK-UHFFFAOYSA-N 4-pyrrolidin-1-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1CCCC1 DATXHLPRESKQJK-UHFFFAOYSA-N 0.000 description 1
- 241001147672 Ancylostoma caninum Species 0.000 description 1
- 241000498253 Ancylostoma duodenale Species 0.000 description 1
- 241000244185 Ascaris lumbricoides Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000498270 Necator americanus Species 0.000 description 1
- 241000975704 Syphacia Species 0.000 description 1
- 241000975692 Syphacia obvelata Species 0.000 description 1
- 241000244031 Toxocara Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 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
- the present invention relates to the discovery that the following novel group of di-stilbazoles, expressed in Formula I, have marked activity against nematode infestations of the intestinal tract
- R is selected from the class consisting of methyl, ethyl, n-propyl, n-butyl and benzyl radicals
- R is selected from the class consisting of the methyl and ethyl radicals
- NR may also be pyrrolidino or piperidino
- X-* is the anion of a non-toxic pharmaceutically acceptable acid.
- the parasites of particular concern are pin-worms (Enterobius vermicularis, Syphacia obvelata and Aspicul'uris tetraptera of mice) and hook-worms (Ancylostoma duodenale and Necator americanus and Ancylostoma caninum of dogs).
- the pin-worms of mice are primarily of interest as test-organisms, Syphacia especially having been found to be a reliable indicator of the elfectiveness of drugs against human pin-worm.
- the hook-worms of dogs are both test-organisms and parasites of some importance in their own right since severe infestations by canine hook-worm are common among dogs in the South of the United States, and light infestations are fairly frequent in the North.
- R cannot be a branched group and its size is pretty well limited at four carbons.
- iodide ion is sufliciently nontoxic. Bromide or chloride or methyl sulfate and ptoluene sulfonate are other convenient values for X cates the critical character of the structure-activity relationships. All of these results were obtained with single doses administered orally. It will be observed (cf. cpds. I-V) that substitution by a [dialkylamino group in the benzenoid rings is essential for high activity and that this substitution must be in the para position (compare III and V). Auxiliary substitution is undesirable (compare IV and V).
- NR has an acceptable value, R may vary considerably. It will be seen from the table that all variations of R Within the definition give active compounds. Of these, however, the methiodides and ethiodides are very much the most accessible.
- 2,-6-bz's (p-pyrrolidinostyryl) pyridine ethiodide compound XII of the table.
- a mixture containing 2.6 g. of 2,6-lutidine ethiodide, 100 cc. of methanol, 4.2 g. of p-pyrrolidinobenzaldehyde and 1 cc. of piperidine was refluxed on a steam bath. Insoluble solid precipitated and heavy bumping started in less than one hour. After 2 hours this product was collected (2 g.) and the filtrates were refluxed for 20 hours longer. A second crop of 2.5 g. was obtained and on standing another day or so the filtrates gave a third crop of one g. The total yield was 5.5 g.
- a method of eradicating infestations of parasitic nematodes inhabiting the intestinal tract which comprises administering orally to the host of the infested locus a compound represented by the formula nematodes inhabiting the intestinal tract which comprises administering orally to the host of the infested locus 2,6- bis (p-dimcthylaminostyryl) pyridine methiodide.
- a method of eradicating infestations of parasitic nematodes inhabiting the intestinal tract which comprises administering orally to the host of the infested locus 2,6-bis (p-dimethylaminostyryl)pyridine benzyl iodide.
- a method of eradicating infestations of parasitic nematodes inhabiting the intestinal tract which comprises administering orally to the host of the infested locus 2,6-bis (p-pyrrolidinostyryl) pyridine ethiodide.
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)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL277327D NL277327A (de) | 1961-04-24 | ||
| US104798A US3085935A (en) | 1961-04-24 | 1961-04-24 | Method for the elimination of nematode infestations |
| US115996A US3075975A (en) | 1961-04-24 | 1961-06-07 | Anthelmintic distilbazoles and method |
| GB22626/61A GB1009301A (en) | 1961-04-24 | 1961-12-22 | Styryl-pyridinium compounds, the preparation thereof, and pharmaceutical compositions thereof |
| DE19621470413 DE1470413A1 (de) | 1961-04-24 | 1962-04-16 | Quaternaere Ammoniumverbindungen,deren Herstellung und pharmazeutische Zubereitungen |
| ES276612A ES276612A1 (es) | 1961-04-24 | 1962-04-18 | Un método para la preparación de compuestos de diestilzabol |
| CH480662A CH413836A (de) | 1961-04-24 | 1962-04-18 | Verfahren zur Herstellung von Distilbazolen |
| DK179562AA DK104234C (da) | 1961-04-24 | 1962-04-18 | Fremgangsmåde til fremstilling af distilbazolforbindelser. |
| AT945364A AT248792B (de) | 1961-04-24 | 1962-04-20 | Verfahren zur Behandlung von Nematodenwurminfektionen bei Tieren |
| AT328762A AT239218B (de) | 1961-04-24 | 1962-04-20 | Verfahren zur Herstellung von neuen quaternären Ammoniumverbindungen des Distilbazols |
| LU41596D LU41596A1 (de) | 1961-04-24 | 1962-04-21 | |
| BR138334/62A BR6238334D0 (pt) | 1961-04-24 | 1962-04-23 | Um processo para a preparacao de compostos do cation distilbazol |
| FR895385A FR1320520A (fr) | 1961-04-24 | 1962-04-24 | Sels quaternaires de dérivés du distilbazole |
| FR895386A FR1841M (fr) | 1961-04-24 | 1962-04-24 | Médicament a base d'un sel quaternaire dérivé du distilbazole. |
| SE451262A SE217920C1 (de) | 1961-04-24 | 1962-04-24 | |
| OA52810A OA02352A (fr) | 1961-04-24 | 1967-03-11 | Sels quaternaires de dérivés du distibazole. |
| MY196793A MY6700093A (en) | 1961-04-24 | 1967-12-31 | Styryl-pyridium compounds, the preparation thereof, and pharmaceutical compositions thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US104798A US3085935A (en) | 1961-04-24 | 1961-04-24 | Method for the elimination of nematode infestations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3085935A true US3085935A (en) | 1963-04-16 |
Family
ID=22302443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US104798A Expired - Lifetime US3085935A (en) | 1961-04-24 | 1961-04-24 | Method for the elimination of nematode infestations |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3085935A (de) |
| AT (2) | AT239218B (de) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873312A (en) * | 1973-05-04 | 1975-03-25 | Eastman Kodak Co | Photoconductive composition and elements containing a styryl amino group containing photoconductor |
| US3883658A (en) * | 1968-09-19 | 1975-05-13 | Burroughs Wellcome Co | Method of treating nematode infestations |
| US4558133A (en) * | 1979-08-08 | 1985-12-10 | Bayer Aktiengesellschaft | p-(Pyridinium-vinyl)-N,N-(disubstituted-aniline salts for dyeing paper and their preparation |
| US5360911A (en) * | 1993-06-17 | 1994-11-01 | General Electric Company | Process for the preparation of stilbazolium salts |
| US20030138374A1 (en) * | 2000-03-22 | 2003-07-24 | Yukitsuda Kudo | Image diagnosis probe based on substituted azobenzene or analogue thereof for disease attributable to amyloid accumulation and composition for image diagnosis containing the same |
| US20040224984A1 (en) * | 2003-03-03 | 2004-11-11 | Selph Jeffrey L. | Methods of treating inflammations and infections with pyridinium salts |
-
1961
- 1961-04-24 US US104798A patent/US3085935A/en not_active Expired - Lifetime
-
1962
- 1962-04-20 AT AT328762A patent/AT239218B/de active
- 1962-04-20 AT AT945364A patent/AT248792B/de active
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883658A (en) * | 1968-09-19 | 1975-05-13 | Burroughs Wellcome Co | Method of treating nematode infestations |
| US3873312A (en) * | 1973-05-04 | 1975-03-25 | Eastman Kodak Co | Photoconductive composition and elements containing a styryl amino group containing photoconductor |
| US4558133A (en) * | 1979-08-08 | 1985-12-10 | Bayer Aktiengesellschaft | p-(Pyridinium-vinyl)-N,N-(disubstituted-aniline salts for dyeing paper and their preparation |
| US5360911A (en) * | 1993-06-17 | 1994-11-01 | General Electric Company | Process for the preparation of stilbazolium salts |
| WO1996008474A1 (en) * | 1993-06-17 | 1996-03-21 | Molecular Optoelectronics Corporation | Process for the preparation of stilbazolium salts |
| JP2838594B2 (ja) | 1993-06-17 | 1998-12-16 | モレキュラ オプトエレクトロニクス コーポレーション | スチルバゾリウム塩の調合方法 |
| US20030138374A1 (en) * | 2000-03-22 | 2003-07-24 | Yukitsuda Kudo | Image diagnosis probe based on substituted azobenzene or analogue thereof for disease attributable to amyloid accumulation and composition for image diagnosis containing the same |
| US20040224984A1 (en) * | 2003-03-03 | 2004-11-11 | Selph Jeffrey L. | Methods of treating inflammations and infections with pyridinium salts |
| WO2004078136A3 (en) * | 2003-03-03 | 2004-12-16 | Mycosol Inc | Pyridinium salts, compounds and methods of use |
| US7220761B2 (en) | 2003-03-03 | 2007-05-22 | Mycosol, Inc. | Compounds and methods for controlling fungi, bacteria and insects |
| JP2007525441A (ja) * | 2003-03-03 | 2007-09-06 | マイコソル，インコーポレイテッド | ピリジニウム塩、化合物および使用法 |
| US7547444B1 (en) | 2003-03-03 | 2009-06-16 | Mycosol, Inc. | Methods for controlling fungi and bacteria |
| US7820696B2 (en) | 2003-03-03 | 2010-10-26 | Mycosol, Inc. | Compounds and methods for controlling fungi, bacteria and insects |
| US8124626B2 (en) | 2003-03-03 | 2012-02-28 | Mycosol, Inc. | Methods of treating inflammations and infections with pyridinium salts |
Also Published As
| Publication number | Publication date |
|---|---|
| AT239218B (de) | 1965-03-25 |
| AT248792B (de) | 1966-08-10 |
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