http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1178465-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_5922cbe7c65a9136f85906fa09e7c967 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J53-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J71-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J17-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J17-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J71-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J53-00 |
| filingDate | 1967-02-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1970-01-21-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1178465-A |
| titleOfInvention | Improvements in or relating to 1,2- and/or 6,7-Methylene or -Halomethylene Steroids |
| abstract | 1,178,465. 1,2- and/or 6,7-methylene or -halomethylene steroids. SYNTEX CORP. 23 Feb., 1967 [28 Feb., 1966; 15 Feb., 1967], No. 8730/67. Heading C2U. The invention comprises novel steroids of the formulµ (wherein R<SP>1</SP> is H, OH, tetrahydropyranyloxy or acyloxy; R<SP>2</SP> is H, OH or acyloxy; R<SP>3</SP> is H, OH or CH 3 or, together with R<SP>2</SP> is 16α,17α- methylenedioxy optionally substituted by groups A and B where A is C 1-8 alkyl and B is C 1-8 alkyl or acyl); R<SP>4</SP> is H, Cl or F; R<SP>5</SP> is O or α-H (#-R<SP>8</SP>) in which R<SP>8</SP> is H, OH or Cl, R<SP>4</SP> being Cl when R<SP>8</SP> is Cl; R<SP>6</SP> is H, CH 3 , Cl or F; R<SP>7</SP> is H or CH 3 ; Z<SP>1</SP> is a carbon-carbon single bond or an α- or #-methylene group optionally mono- or di-substituted by Cl and/or F; Z<SP>2</SP> has the same meanings as Z<SP>1</SP>, at least one of Z<SP>1</SP> and Z<SP>2</SP> being the optionally substituted methylene group; R is H or acyl; R<SP>3#1</SP> is H or CH 3 ; Z<SP>10</SP> is a carbon-carbon single bond or an α-methylene group; and Z<SP>20</SP> is an α-difluoro-methylene group) and the novel 1,2-methylene-6,7-difluoromethylene - 17α - acyloxypregn - 4 - ene- 3,20-diones and the corresponding 17α-hydroxy and 17α-unsubstituted derivatives. The 3- tetrahydropyranyl ethers are prepared by reduction of the corresponding 3-ketones followed by etherification of the 3#-ols thus-produced. The 3-ketones are prepared by processes described in Specification 1,163,736. The 3- acylates are prepared by acylation of the 3#-ols. In the products 17α- and 21-acyloxy groups may be hydrolysed. 1,2 - Methylene - 17α - acetoxy - pregn - 4 - ene - 3,20-dione is prepared by reducing and backoxidizing 17α-hydroxy-progesterone to give 5α-pregnan-17α-ol-3,20-dione, brominating and dehydrobrominating this to give 5α-pregn-1-en- 17α-ol-3,20-dione, converting this to 20,20- ethylenedioxy - 5α - pregn - 1 - en - 17α - ol - 3 - one, converting this to 1,2-methylene-20,20-ethylenedioxy - 5α - pregnan - 17α - ol - 3,20 - dione (the 1α,2α- and 1#,2#-isomers are obtained using dimethylsulphoxonium methylide reagent; they may be separated and used individually or used as a mixture), hydrolysing to the 20-ketone, brominating to give the 4-bromo compound and dehydrobrominating to give 1,2-methylenepregn- 4-en-17α-ol-3,20-dione and acylating this. 1,2- Methylene - 21 - acetoxypregn - 4 - ene - 11#,17α - diol-3,20-dione is prepared by similar methods to the above, the side chain being protected as the bismethylenedioxy derivative and released before 21-acylation. The products may be dehydrogenated to the 4,6-dienes. Other 3-keto-4,6- diene and 4-ene starting materials are prepared similarly. The 4,6-dienes may be converted to #<SP>4</SP>-6,7-difluoromethylene compounds, e.g. 6,7-difluoromethylene - 17α - acetoxy - pregn - 4 - ene - 3,20-diones, and to the corresponding dichloromethylene and monohalomethylene compounds. The steroids of the invention, which are variously stated to possess anabolic, corticoid, e.g. anti-inflammatory, and progestational activities may be made up into pharmaceutical compositions with suitable carriers. |
| priorityDate | 1966-02-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 43.