IL24650A - 3-oxime and 3-aza-a-homo-steroids of the pregnane series - Google Patents

Description

A and of the pregnane series ORTHO 23597 This invention consists in steroids and steroids the pregnane series the in which when X is Y is a carbon or when X is Y is the roup interposed between the and R is bromine or is hydrogen or alkyl from 1 to 11 carbon atoms and is hydrogen The new steroids have the formula 2 In both formulae and the meaning as in formula compounds of the present invention are potent progestational agents and more larly possess The invention also consists in processes for the paration o eoinpounds the formulae steroidal osimes of formula XI can be prepared by reaction of a carbonyl group on the steroid the formula wherein R is or from 1 to 11 carbon and o with a sal in of a base such as sodium hydroxide or sodium When a steroid having a carbonyl at the is subjected to treatment with a salt under basic the would be the expected due to the presence o group in the starting compounds of formula steric hindrance prevents the oximation of the can be readily verted to the alcohol by She of III are prepared by subjecting an to Beckmann rearrangement a 24650 2 which may be used in the Beckmann rearrangement are benzenesulfonyl chloride o phosphorus The invention is illustrated by the following Examples to which it is is treated with 30 ml ml of pyridine and g of hydroxylamine The mixture is heated on a 148 bath for hour and allowed to The precipitates are filtered and recrystalllzed from methanol to give Analysis Calculated for EXAMPLE II One and a half gram of 10 treated with 25 of 500 of hydroxylamine hydrochloride and 500 of sodium The mixture is heated on a steam bath for hour and allowed to The crystals are filtered and from methanol to give 15 Analysis Calculated for Found EXAMPLE III 20 One gram of is dissolved in 15 of pyridine containing 250 of hydroxylamine The flask is heated on a for hour and poured over a large excess 25 of The solid material is collected by filtration and recrystalllzed from methanol to give ORTH Analysis Calculated for Following procedure of les I to the followin related oompounds are prepared starting from the appropriate EXAMPLE IV treated with 10 of dioxane and of thlonyl The mixture is stirred for one and half hours and poured over The solid material is extracted with ethyl The organic layer with water until neutral to dried over sodium sulfate and The residue is recrystallized from to give 148 Analysis Calculated for EXAMPLE V One of is treated with of polyphosphoric o acid and maintained between for one The is decomposed with and extracted with methylene The organic layer is further washed with water until neutral to dried over sodium sulfate and The residue is crystallized from followed by recrystallization from to give Analysis for Pound EXAMPLE VI One gram of 20 of dioxane and treated with of thionyl The mixture i3 stirred 2 hours and decomposed with a large amount of It is extracted with methylene chloride and the organic layer is washed with potassium bicarbonate solution 148 sodium sulfate and evaporated to give a which is recrystallized from to give Analysis V Calculated for Following the procedure of Examples IV to the following related compounds are prepared starting the appropriate 5 0 and 5 insufficientOCRQuality

Claims (1)

1. CLAIMS steroids and steroids of the pregnane having the formula R in when is Ϋ a carbon or when X is is the interposed between the and R is bromine or is hydrogen or alkyl grom 1 to 11 carbon atoms and is hydrogen or wherein and have the same meaning as in Claim compounds according to Claim 1 of the formula 8 wherein steroids and steroids of the pregnane series according to Claim substantially as scribed herein with reference to the A method of preparing compounds of the Formula II in Claim wherein a compound of the formula in R and have the same meaning as to Claim 2 and is an group of from 1 to 11 carbon is reacted with a salt in the presence of a and if desired the obtained is 9 A method according to Claim wherein the base is sodium hydroxide or A method of preparing compounds of the III in Claim wherein a compound of the formula II in Claim in which and have the same meaning as i Claim is subjected to a Beckmann rearrangement in the presence of an acidic A process according to Claim wherein the acidic reagent is thionyl polyphosphoric sulfonyl chloride or phosphorus Processes for the preparation of steroids and steroids according to Claim substantially as described herein with reference to the Examples the Applicants PG insufficientOCRQuality