GB1356717A - 3-tert butyl-6-methyl-5-nitrosalicyl-anilides methods of preparation and anthelmintic compositions thereof - Google Patents
3-tert butyl-6-methyl-5-nitrosalicyl-anilides methods of preparation and anthelmintic compositions thereofInfo
- Publication number
- GB1356717A GB1356717A GB4553672A GB4553672A GB1356717A GB 1356717 A GB1356717 A GB 1356717A GB 4553672 A GB4553672 A GB 4553672A GB 4553672 A GB4553672 A GB 4553672A GB 1356717 A GB1356717 A GB 1356717A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- butyl
- nitrosalicyl
- anilides
- preparation
- 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
Links
- 230000000507 anthelmentic effect Effects 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title abstract 3
- DPRDEPAEKGNUJP-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-nitro-n-phenylbenzamide Chemical class CC1=C([N+]([O-])=O)C=C(C(C)(C)C)C(O)=C1C(=O)NC1=CC=CC=C1 DPRDEPAEKGNUJP-UHFFFAOYSA-N 0.000 title abstract 2
- QANDJRKMSAUDCP-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-nitrobenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1[N+]([O-])=O QANDJRKMSAUDCP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- JXQCUCDXLSGQNZ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1C(O)=O JXQCUCDXLSGQNZ-UHFFFAOYSA-N 0.000 abstract 1
- 101100188552 Arabidopsis thaliana OCT3 gene Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- -1 cyano, hydroxy Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 abstract 1
- 229950000975 salicylanilide Drugs 0.000 abstract 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C205/60—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
Abstract
1356717 3 - Tert - butyl - 6 - methyl - 5 - nitrosalicylanilides and anthelmintic compositions thereof FERRO CORP 3 Oct 1972 [4 Oct 1971] 45536/72 Heading C2C The invention comprises compounds of formula wherein R and R 1 are independently hydrogen, halogen, -CF 3 , R 3 , -OR 3 , or NO 2 groups; R 2 is hydrogen, -CF 3 , sulphonyl, cyano, hydroxy, or -COOR 3 ; and R 3 is a C 1-4 alkyl group; with the proviso that when R is 2<SP>1</SP>-halo, R 1 is not a 5<SP>1</SP>-halo. These compounds may be obtained by the reaction of 3-tert-butyl-6-methyl-5-nitrosalicylic acid with an appropriately substituted aniline. The intermediate 3-t-butyl-6-methyl-5-nitrosalicylic acid is prepared by the nitration of 3- t-butyl-6-methylsalicylic acid. The invention also comprises an anthelmintic composition containing a salicylanilide according to the invention in admixture with a suitable extending agent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18651471A | 1971-10-04 | 1971-10-04 | |
| DE19732347615 DE2347615A1 (en) | 1971-10-04 | 1973-09-21 | 3-TERT-BUTYL-4'-BROMINE-6-METHYL-5NITRO-2'-TRIFLUOROMETHYLSALICYLIC ACID ANILIDE, PROCESS FOR THE PREPARATION AND MEDICINAL PRODUCTS CONTAINING THIS COMPOUND |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1356717A true GB1356717A (en) | 1974-06-12 |
Family
ID=25765838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4553672A Expired GB1356717A (en) | 1971-10-04 | 1972-10-03 | 3-tert butyl-6-methyl-5-nitrosalicyl-anilides methods of preparation and anthelmintic compositions thereof |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS4844230A (en) |
| AR (1) | AR197003A1 (en) |
| BE (1) | BE789027A (en) |
| BR (1) | BR7206892D0 (en) |
| CH (1) | CH577466A5 (en) |
| DE (1) | DE2248580A1 (en) |
| FR (1) | FR2155947B1 (en) |
| GB (1) | GB1356717A (en) |
| LU (1) | LU66215A1 (en) |
| NL (1) | NL7213293A (en) |
| ZA (1) | ZA726087B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3721737A (en) * | 1968-11-15 | 1973-03-20 | Monsanto Co | 2',5'-dihalo-3-tert.alkyl-5-nitrosalicylanilides for combatting lepidoptera chewing larvae |
-
1972
- 1972-09-06 ZA ZA726087A patent/ZA726087B/en unknown
- 1972-09-20 BE BE789027D patent/BE789027A/en unknown
- 1972-09-27 FR FR7234127A patent/FR2155947B1/fr not_active Expired
- 1972-09-28 AR AR244336A patent/AR197003A1/en active
- 1972-10-02 LU LU66215A patent/LU66215A1/xx unknown
- 1972-10-02 NL NL7213293A patent/NL7213293A/xx not_active Application Discontinuation
- 1972-10-03 JP JP47099364A patent/JPS4844230A/ja active Pending
- 1972-10-03 CH CH1339572A patent/CH577466A5/xx not_active IP Right Cessation
- 1972-10-03 GB GB4553672A patent/GB1356717A/en not_active Expired
- 1972-10-04 BR BR006892/72A patent/BR7206892D0/en unknown
- 1972-10-04 DE DE19722248580 patent/DE2248580A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE2248580A1 (en) | 1973-04-12 |
| JPS4844230A (en) | 1973-06-26 |
| FR2155947A1 (en) | 1973-05-25 |
| LU66215A1 (en) | 1973-01-23 |
| CH577466A5 (en) | 1976-07-15 |
| AR197003A1 (en) | 1974-03-08 |
| ZA726087B (en) | 1973-06-27 |
| BE789027A (en) | 1973-03-20 |
| BR7206892D0 (en) | 1973-12-06 |
| FR2155947B1 (en) | 1976-05-21 |
| NL7213293A (en) | 1973-04-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1103586B (en) | Oxidative hair dye compositions | |
| GB1459571A (en) | Thiophene-2-sulphonamide derivatives and their use as therapeutic agents sheet orienting apparatus | |
| GB1434876A (en) | Diphenylmethane derivatives and their use as inseciticides | |
| GB1510609A (en) | Nematic compounds and liquid crystal compositions containing them | |
| ES454747A1 (en) | Aminotetralols | |
| GB1337860A (en) | Nitrodiphenyl ether derivatives and their use as herbicides | |
| GB1356717A (en) | 3-tert butyl-6-methyl-5-nitrosalicyl-anilides methods of preparation and anthelmintic compositions thereof | |
| GB1142981A (en) | Phenylisopropylamine derivatives | |
| GB1489489A (en) | Functional fluid compositions containing stabilizers | |
| GB974718A (en) | Maleimide derivative | |
| ES265738A1 (en) | Method of treating angina pectoris | |
| GB1310705A (en) | Method for the preparation of n-3-oxyhydrocarbon - substituted acrylamides | |
| GB1465042A (en) | Catalysts for the manufacture of unsaturated nitriles | |
| GB1505020A (en) | Substituted 2-phenylimino-thiazolines a process for their preparation and their use as ectoparasiticides | |
| GB1397387A (en) | Preparation of 2-alkylaminoalkyl 6-methyl-7-nitro- 1,2,3,4-tetrahydroquinolines | |
| GB1465718A (en) | Isolation of 1,5-dinitroanthraquinone | |
| GB1362928A (en) | Insecticidal esters of 1-acenaphthenol | |
| ES2049243T3 (en) | PROCEDURE FOR THE PREPARATION AND USE OF NEW 2-THIOZOLIDINONE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. | |
| GB1339244A (en) | N-1,1 substituted acetonitrilo-a-3,5-substituted phenoxy alkyl amides and their use as herbicides | |
| GB1458528A (en) | Pyrazolotriazoles | |
| GB1366005A (en) | Substuted cyanobenzimidazoles | |
| GB1329012A (en) | Trifluoromethylnitraminobenzenes and herbicidal compositions containing them | |
| GB1460266A (en) | Pyridine-thioether-sulphoxides processes for their preparation and compositions containing them | |
| GB1309053A (en) | Industrial microbicidal compositions containing propiolic acid esters | |
| GB1252087A (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |