http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-629118-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_dc2f7134efa50484bb359fda73782848 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C62-32 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C62-34 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C62-32 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C62-34 |
| filingDate | 1947-03-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1949-09-13-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-629118-A |
| titleOfInvention | Manufacture of hydrophenanthrene monocarboxylic acids and derivatives thereof |
| abstract | Hydrophenanthrene monocarboxylic acids and derivatives thereof are made by converting the carboxyl group of the fatty acid residue in a hydrophenanthryl-1-fatty acid (which contains in the 7-position a substituted hydroxyl group and in the 2-position an alkyl residue and an esterified carboxyl group) into an acid halide group, reducing this first to an aldehyde group and then to a methyl group, and if desired hydrolysing the groups in the 2- and 7-positions; the products may be esterified, etherified and converted into salts. The starting materials may be obtained by partial hydrolysis of diesters of the corresponding 2-carboxy-hydrophenanthryl-1-fatty acids, the latter being obtained by the oxidative degradation of steroids. The starting materials are heated with oxalyl chloride to yield the acid chloride and the latter reduced to the aldehyde by treatment with hydrogen in the presence of a catalyst (e.g. palladium). The aldehyde may be isolated by conversion into the pyridiniumacetic acid hydrazide. Reduction of the aldehyde group to a methyl group may be effected with zinc and hydrochloric acid, with chromous salts, or with hydrazine and an alkali alcoholate (or glycolate); alternatively, the reduction may take place indirectly via the hydrazone or semi-carbazone. The product may be obtained in the optically-active or racemic form, and may be converted into a therapeutically-active stereoisomer. Examples show the preparation of the 1-ethyl-2-methyl-tetrahydro -, 1 - ethyl - 2 : 13 - dimethyl-dodecahydro, 1 - ethyl - 2 - methyl - octahydro-and 1 - propyl - 2 - methyl - tetrahydro - compounds, and the use of a hydrophenanthryl-1-formic acid is mentioned as a starting material. The Specification as open to inspection under Sect. 91 is not confined to compounds substituted in the 7-position or carrying an alkyl substituent in the 2-position and mentions also as starting materials (a) compounds with a free hydroxyl group in the 7-position, and (b) compounds containing in the 2-position any substituent convertible by hydrolysis into a carboxyl group, e.g. acid amide or nitrile group. Alternative methods of converting the aldehyde group into a methyl group are via the carbinol, p thioacetal and dihalide. In a modification of the process, the acid halide is converted into a thioester and the latter catalytically reduced. This subject-matter does not appear in the Specification as accepted. |
| priorityDate | 1946-03-07-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 44.