http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1287271-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_dbd2b89e8e7cecadfc3e2d0124ce65bf |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J71-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J71-00 |
| filingDate | 1969-07-09-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_4840e13342167e40be3dda022170dfc5 |
| publicationDate | 1972-08-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1287271-A |
| titleOfInvention | Steroids having a heterocyclic ring fused to the 3,4-position thereof |
| abstract | 1287271 Steroid [3,4] heterocycles BOOTS CO Ltd 6 Oct 1970 [9 July 1969] 34556/69 Headings C2C and C2U The invention comprises 3,4-heterocyclicfused steroids (including D-norsteroids) of partial formulµ wherein R is H or alkyl; R<SP>2</SP> is H, acyl, alkyl, cycloalkyl, aralkyl, aryl or heterocyclic; R<SP>3</SP> is OH or SH; and R<SP>1</SP> is alkyl, cycloalkyl, ary], aralkyl, heterocyclic, C 1-4 alkoxy or C 1-4 alkylthio; and salts and solvates thereof; and the preparation of these compounds and of steroid [3,4] heterocycles in general, by reacting a 3,5- dienamine of a #<SP>4</SP>-3-keto-steroid with a Vilsmeier reagent to yield an iminium compound of partial Formula I or II (wherein R is H in I and is alkyl in II and X- is an anion derived from the Vilsmeier reagent) and reacting said iminium compound or one of its hydrolysis products of partial Formula III, IV or V (wherein R is H in III and V and is alkyl in IV) with hydrazine or mono-substituted hydrazine (to give, e.g., XIIIa and/or XIIIb), or hydroxylamine (to give, e.g. XIVa and/or XIVb), or cyanoacetamide or cyanothioacetamide (to give, e.g. XVa and/or XVb), or an amidine, an S- alkylthiouronium salt or an O.alkyluronium salt (to give, e.g. XVI), when mixtures of isomers are obtained, these are separated by chromatography. Alternatively, in the case of the isoxazoles, the [3,4-c] isomer (XIVb) may be purified from the [4,3-dl isomer (XIVa) by treatment with alkali. The steroid [3,4] heterocycles are interconvertible by: (i) hydrolysis of b.m.d.o., (ii) hydrolysis of 17-esters, (iii) hydrolysis of 11#- formyloxy, (iii) esterification of 17- and 21- hydroxy groups (optionally via 17,21- orthoesters), (iv) esterification of pyrazoles (XIII, R<SP>2</SP>=H-#R<SP>2</SP>=Acyl), (v) ethynylation of 17- OXO and (v) replacement of 21-mesyloxy with H, F or Cl (a 17,21-epoxide also possibly being formed). The 3,5-dienamine starting materials are prepared conventionally from #<SP>4</SP>-3-ones. 17a- Ethynyl - 3 - morpholinoandroata - 3,5 - dien- 17#-ol is prepared by ethynylation of the corresponding 17-one (Example 14). The inventive compounds are said to possess antiinflammatory, glucocorticoid, anabolic and progestational activities, and may be made up with carriers into pharmaceutical compositions for oral, parenteral and topical administration. |
| priorityDate | 1969-07-09-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
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