IL43483A - Amidophenylisothioureas,their production and pharmaceutical compositions containing them - Google Patents
Amidophenylisothioureas,their production and pharmaceutical compositions containing themInfo
- Publication number
- IL43483A IL43483A IL43483A IL4348373A IL43483A IL 43483 A IL43483 A IL 43483A IL 43483 A IL43483 A IL 43483A IL 4348373 A IL4348373 A IL 4348373A IL 43483 A IL43483 A IL 43483A
- Authority
- IL
- Israel
- Prior art keywords
- radical
- carbon atoms
- compound
- ethyl
- methyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Abstract
1393329 Isothioureas BAYER AG 26 Oct 1973 [27 Oct 1972] 49935/73 Heading C2C The invention comprises novel compounds (I) in which X is an alkyl radical with 1 to 6 carbon atoms; R is an alkyl radical with 1 to 12 carbon atoms, or a cycloalkyl radical with up to 8 carbon atoms, or an alkenyl radical with up to 12 carbon atoms, or an aralkyl radical (optionally carrying in its aryl part at least one substituent selected from alkyl and alkoxy groups, each with 1 to 4 carbon atoms, and halogen atoms); R<SP>1</SP> is an alkyl radical with 1 to 4 carbon atoms; and R<SP>2</SP> is a hydrogen atom or an alkyl radical with 1 to 18 carbon atoms (optionally carrying at least one substituent selected from halogen and nitrile radicals, alkoxy radicals with 1 to 4 carbon atoms, alkoxycarbonyl radicals with 2 to 5 carbon atoms, and phenoxy, halophenoxy, alkylphenoxy and alkoxyphenoxy radicals), or a cycloalkyl radical with 5 to 8 carbon atoms, or an aralkyl radical (optionally carrying at least one substituent selected from halogen atoms, alkyl radicals with 1 to 4 carbon atoms, and alkoxy radicals with 1 to 4 carbon atoms), or an aryl radical (optionally carrying at least one substituent selected from halogen atoms and alkyl and alkoxy radicals with 1 to 4 carbon atoms each) or a 1-furyl radical. They are made by alkylating the corresponding thioureas. Pharmaceutical preparations showing anthelmintic action contain (I) as active ingredient; standard administration forms are described.
[GB1393329A]
Claims (4)
1. Compounds which are isothiourea compounds of the following general formula:- in which X is an alkyl radical with 1 to 6 carbon atoms; R is a . straight or branched chain lower alkyl radical or a lower alkenyl radical; R1 is an alkyl radical with 1 to 4 carbon atoms ; and R 2 is a lower alkyl radical or/aphenyl radical.
2. Compounds according to claim 1 in which X is a methyl, ethyl or n-butyl radical .
3. Compounds according to claim 1 or 2 in which R1 is a methyl, ethyl, isopropyl or sec-butyl radical. 2 . 4. Compounds according to claim 1, 2 or 3 in which R is a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, iso amyl or phenyl radical.
5. Compounds according to any preceding claim in which R is a methyl, ethyl, isopropyl or allyl radical.
6. The compound of the formula:- Compounds according to claim 1 or 2 in which R methyl, ethyl, isopropyl or sec-butyl radical. 2
4. Compounds according to claim 1, 2 or 3 in which R is a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, iso amyl, cyclopentyl, cyclohexyl, phenylmethyl, phenoxymethyl, phenyl or jg-tolyl radical.
5. Compounds according to any preceding claim in which R is a methyl, ethyl, isopropyl, allyl, cyclohexyl or benzyl radical.
6. The compound of the formula: -
7. The compound of the formula:-
8. The compound of the formula:-
9. The compound of the formula: - Le A 14 648-RTF - 32 -
13. A process for the production of a compound according to any of claims 1 to 12 in which a thiourea of the general formula: - S II is reacted with an alkylating agent of the general formula R - Y (III) [in which general formulae (II) and (III) X, R, R1 and R2 are as defined in any of claims 1 to 5 and Y is .a halogen, aryl-sulphonyloxy or alkoxysulphonyloxy radical! in the presence of base and of a diluent.
14. A process according to claim 13 in which the' base is potassium or sodium hydroxide or sodium carbonate or bicarbonate,
15. A process according to claim 13 or 14 in which the reaction is carried out at 0 to 30°C.
16. A process for the production of compounds according to claim 1 substantially as hereinbefore described in Example 1. 17· Compounds according to claim 1 whenever produced by a process according to any of claims 13 to 16.
18. A pharmaceutical composition containing as an active ingredient a compound according to any of claims 1 to 12 and 17 in admixture with a solid or liquefied gaseous diluent or in admixture with a liquid diluent other than a solvent of a molecular weight less than 200 except in the presence of a surface-active agent.
19. A pharmaceutical composition containing as an active ingredient a compound according to any of. claims 1 to 12 and 17 in the form of a sterile or isotonic aqueous solution.
20. A composition according to claim 18 or 19 containing from 0.5 to 90 percent of active ingredient by weight.
21. A pharmaceutical composition according to claim 18 or 19 substantially as hereinbefore described.
22. A medicament in dosage unit form comprising a compound according to any of claims 1 to 12 and 17 either alone or in admixture with a diluent.
23. A medicament in the form of tablets, pills, dragees, capsules, ampoules or suppositories comprising a compound according to any of claims 1 to 12 and 17 either alone or in admixture withja diluent.
24. A medicament according to claimj22 or 23 substantially as hereinbefore described.
25. A method of combating helminthic infestation in non-human animals which comprises administering to the animals an active compound according to any of claizhs 1 to 12 and 17 either alone or i admixture with a diluent or in the form of a medicament according to claim 22 or 23.
26. A method according to claim 23 in which the active compound is administered in an amount' of 5 to 100 mgAg body weight per day. 27u. A method according to claim 25 or 26 in which the active compound is administexeldperorally. 28,. A method according to claim 25, 26 or 27 in which the helmintic infestation is by hookworms , Trichostrongylides , Strongylides, Rhabditides, eelworms, threadworms, Heterakides , or Filariae.
29. A method according to claim 25 substantially as hereinbefore described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2252691A DE2252691A1 (en) | 1972-10-27 | 1972-10-27 | AMIDOPHENYLISOTHIOURA, METHOD OF MANUFACTURING AND USE AS A MEDICINAL PRODUCT |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43483A0 IL43483A0 (en) | 1974-01-14 |
| IL43483A true IL43483A (en) | 1976-08-31 |
Family
ID=5860198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43483A IL43483A (en) | 1972-10-27 | 1973-10-25 | Amidophenylisothioureas,their production and pharmaceutical compositions containing them |
Country Status (23)
| Country | Link |
|---|---|
| JP (2) | JPS4980216A (en) |
| AR (1) | AR199590A1 (en) |
| AT (1) | AT330199B (en) |
| AU (1) | AU475884B2 (en) |
| BE (1) | BE806549A (en) |
| CA (1) | CA1016349A (en) |
| CH (1) | CH588458A5 (en) |
| CS (1) | CS165965B2 (en) |
| DE (1) | DE2252691A1 (en) |
| DK (1) | DK134398C (en) |
| ES (1) | ES419990A1 (en) |
| FR (1) | FR2204420B1 (en) |
| GB (1) | GB1393329A (en) |
| HU (1) | HU167555B (en) |
| IE (1) | IE38427B1 (en) |
| IL (1) | IL43483A (en) |
| KE (1) | KE2586A (en) |
| LU (1) | LU68690A1 (en) |
| NL (1) | NL7314614A (en) |
| PH (1) | PH10384A (en) |
| PL (1) | PL91111B1 (en) |
| SU (1) | SU490285A3 (en) |
| ZA (1) | ZA738287B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2434183C2 (en) * | 1974-07-16 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Substituted phenylisothioureas, a process for their preparation and their use as pharmaceuticals |
-
1972
- 1972-10-27 DE DE2252691A patent/DE2252691A1/en active Pending
-
1973
- 1973-10-23 AR AR250650A patent/AR199590A1/en active
- 1973-10-23 SU SU1966532A patent/SU490285A3/en active
- 1973-10-24 NL NL7314614A patent/NL7314614A/xx unknown
- 1973-10-24 AU AU61768/73A patent/AU475884B2/en not_active Expired
- 1973-10-24 PH PH15148A patent/PH10384A/en unknown
- 1973-10-25 JP JP48119502A patent/JPS4980216A/ja active Pending
- 1973-10-25 CH CH1504773A patent/CH588458A5/xx not_active IP Right Cessation
- 1973-10-25 CA CA184,274A patent/CA1016349A/en not_active Expired
- 1973-10-25 IL IL43483A patent/IL43483A/en unknown
- 1973-10-25 JP JP48119501A patent/JPS4976836A/ja active Pending
- 1973-10-25 LU LU68690A patent/LU68690A1/xx unknown
- 1973-10-25 AT AT904173A patent/AT330199B/en not_active IP Right Cessation
- 1973-10-26 HU HUBA2989A patent/HU167555B/hu unknown
- 1973-10-26 DK DK580973A patent/DK134398C/en active
- 1973-10-26 GB GB4993573A patent/GB1393329A/en not_active Expired
- 1973-10-26 PL PL1973166117A patent/PL91111B1/pl unknown
- 1973-10-26 ZA ZA738287A patent/ZA738287B/en unknown
- 1973-10-26 BE BE137089A patent/BE806549A/en unknown
- 1973-10-26 CS CS7387A patent/CS165965B2/cs unknown
- 1973-10-26 IE IE1935/73A patent/IE38427B1/en unknown
- 1973-10-26 FR FR7338264A patent/FR2204420B1/fr not_active Expired
- 1973-10-26 ES ES419990A patent/ES419990A1/en not_active Expired
-
1975
- 1975-12-02 KE KE2586*UA patent/KE2586A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1393329A (en) | 1975-05-07 |
| CA1016349A (en) | 1977-08-30 |
| DE2252691A1 (en) | 1974-05-02 |
| DK134398B (en) | 1976-11-01 |
| FR2204420B1 (en) | 1977-09-09 |
| ZA738287B (en) | 1974-09-25 |
| AR199590A1 (en) | 1974-09-13 |
| FR2204420A1 (en) | 1974-05-24 |
| AU475884B2 (en) | 1976-09-09 |
| NL7314614A (en) | 1974-05-01 |
| AT330199B (en) | 1976-06-25 |
| JPS4980216A (en) | 1974-08-02 |
| IL43483A0 (en) | 1974-01-14 |
| ATA904173A (en) | 1975-09-15 |
| HU167555B (en) | 1975-11-28 |
| KE2586A (en) | 1975-12-19 |
| SU490285A3 (en) | 1975-10-30 |
| IE38427L (en) | 1974-04-27 |
| PH10384A (en) | 1977-03-02 |
| JPS4976836A (en) | 1974-07-24 |
| AU6176873A (en) | 1975-04-24 |
| CS165965B2 (en) | 1975-12-22 |
| DK134398C (en) | 1977-03-28 |
| CH588458A5 (en) | 1977-06-15 |
| ES419990A1 (en) | 1976-03-16 |
| BE806549A (en) | 1974-04-26 |
| PL91111B1 (en) | 1977-02-28 |
| IE38427B1 (en) | 1978-03-15 |
| LU68690A1 (en) | 1974-01-08 |
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