http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1168350-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d202e9e866984fe229f6facc38f1d740 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D333-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D231-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D231-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D231-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D231-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D231-56 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-64 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-70 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-56 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-90 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-91 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D277-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D277-34 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D277-26 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D277-24 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-92 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D249-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D319-20 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D333-18 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D333-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D333-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D277-34 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D277-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D231-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D231-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D231-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D231-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D277-26 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D277-24 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-91 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-90 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-92 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-70 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-64 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D319-20 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D231-56 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-56 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-54 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D521-00 |
| filingDate | 1967-11-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0c86a3d9c24723567e3a4a86aa03d9bd http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_df8fb6bda7277ae5a2e8cc551fdcd3c8 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_37bacc5149c0d2f40ee09f56f8bbd386 |
| publicationDate | 1969-10-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1168350-A |
| titleOfInvention | Heterocyclylmethyl Alkyl Sulfoxides |
| abstract | 1,168,350. Methyl sulphinyl methyl-heterocyclic compounds. MERCK & CO. Inc. 6 Nov., 1967 [9 Nov., 1966], No. 50359/67. Heading C2C. The invention comprises compounds of the general formula in which " Het " is a heteroaromatic radical containing one or two 5- or 6-membered rings and that contains more than one hetero atom if it is an unsubstituted monocyclic oxa or thia radical and if R 2 and R 3 are both hydrogen; Y is a halogen atom or a C 1-5 alkyl, C 2-5 alkenyl, cyclic C 3-6 alkyl, amino, C 1-5 alkylamino, di- (C 1-5 alkyl)amino, hydroxy, C 1-5 alkoxy, mercapto, C 1-5 alkylmercapto or nitro radical, n is 0, 1 or 2; each of R 2 and R 3 is a hydrogen atom or a C 1-5 alkyl or C 2-5 alkenyl radical and R 4 is a C 1-5 alkyl or C 2-5 alkenyl radical which are prepared by reacting a compound of the formula in which X is a chlorine, bromine or iodine atom and R 2 , R 3 " Het ", Y and n are as defined above with an alkali metal R 4 -mercaptide to form a sulphide compound and subsequently oxidizing the said sulphide compound. When " Het " is an indole ring compounds of Formula I are prepared by reacting an indole compound of the formula in which R and R 1 are each equal to hydrogen or to Y as defined above, with dimethylamine and formaldehyde to produce the corresponding 3-dimethylaminomethyl derivative and subsequently reacting this with an alkali metal R 4 - mercaptide and oxidizing the product to produce a compound of the formula where R 4 is as defined above. When " Het " is a heterocyclic residue containing nitrogen and only one of R 2 and R 3 is hydrogen compounds of Formula I are prepared by reacting a compound of the formula where one of R 5 and R 6 is a hydrogen atom or C 1-5 alkyl or C 2-5 alkenyl, radical with an N- halosuccinimide in the presence of at least a catalytic amount of a peroxide to produce the corresponding halogen substituted compound, reacting this with an alkali metal-R 4 -mercaptide to form a sulphide compound and oxidizing said sulphide compound to form a compound of Formula I. When Y, n, R 2, R 3 and R 4 are as defined previously and " Het " is a radical containing at least one nitrogen atom, compounds of Formula I are prepared by reacting (Y) n -[Het] with a halogenated compound of the formula in the presence of an alkali or alkaline earth metal hydroxide to form the corresponding heterocyclic sulphide compound and subsequently oxidizing this to produce a compound of Formula I in which the sulphoxide residue is attached to Het " via the nitrogen atom. When " Het " is a heterocyclic residue containing one or more oxygen and/or sulphur atoms and at least one of R 2 and R 3 is other than hydrogen compounds of Formula I are prepared by reacting a compound of the formula with a C 1-5 alkyl or C 2-5 alkenyl iodide in the presence of a strong base. 2- or 4-Chloromethylthiazole is prepared by reacting thionyl chloride with 2- or 4-hydroxythiazole. The 2-hydroxy compound is prepared by reacting thiazole with formalin; the 4- hydroxy compound is prepared by reducing 4-formylthiazole. 3 - Chloromethylpyrdzole (or 4 - chloromethylimidazole) is prepared by reacting thionylchloride with 3-hydroxymethylpyrazole (or 4- chloromethylimidazole) which is prepared by reducing 3-ethoxycarbonylpyrazole (or 4-ethoxycarbonylimidazole). The ester is prepaed by treating 3-carboxypyrazole (or 4-carboxyimidazole with ethanol. 3-Carbozy-pyrazole is prepared by oxidizing 3-methylpyrazole. 4-Carboxy-imidazole is prepared by the acid hydrolysis of 4-anilinocarbonylimidazole which is prepared by reacting aniline with 4,5-dicarboxyimidazole which is obtained by hydrolysis of the corresponding 4,5-diethylester. 2 - Iodomethyl - 1,4 - benzodioxane is prepared by reacting the corresponding 2-chloromethyl compound with sodium iodide. 2 - Methyl - 3 - dimethylaminomethyl - 5 - methoxyindole is prepared by reacting 2-methyl-5- methoxy indole with formalin and dimethylamine. 1 - Methylthiomethylimidazole, optionally substituted at the 2-, 3- or 4-position by C 1-5 alkyl, bromine, methoxy or methylthiomethyl, 1 - methylthiomethylbenzimidazole and 1 - methylthiomethylpyrazole optionally substituted at the 3-, 4- or 5-position by C 1-5 alkyl, chlorine, bromine, ethoxy and nitro, are prepared by reacting the corresponding heterocycle with chloro methylmethylsulphide. 2 - Methylthiomethylthiazole and 4 - hydroxy- 2-methylthiomethylthiazole are prepared by reacting methylthioacetamide with chloroacetaldehyde and chloroacetic acid respectively. 4 - Methoxy - 2 - methylthiasole is prepared by methylating the corresponding 4-hydroxy compound. Pharmaceutical compositions containing compounds of Formula I as active ingredient are administered orally and have analgesic antiinflammatory and antipyretic activity. |
| priorityDate | 1966-11-09-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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