GB879208A - Process for the manufacture of chloracetates and aminoacetates of saturated and unsaturated 21-hydroxy-pregnane compounds and acid addition products of the aminoacetates - Google Patents

Process for the manufacture of chloracetates and aminoacetates of saturated and unsaturated 21-hydroxy-pregnane compounds and acid addition products of the aminoacetates

Info

Publication number
GB879208A
GB879208A GB6977/58A GB697758A GB879208A GB 879208 A GB879208 A GB 879208A GB 6977/58 A GB6977/58 A GB 6977/58A GB 697758 A GB697758 A GB 697758A GB 879208 A GB879208 A GB 879208A
Authority
GB
United Kingdom
Prior art keywords
acetate
hydroxy
pregnane
saturated
unsaturated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB6977/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Publication of GB879208A publication Critical patent/GB879208A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
    • C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

21-Chloroacetates of saturated and unsaturated 21-hydroxy-pregnane compounds are prepared by reacting the required 21-hydroxy pregnane compounds with chloracetic anhydride in the presence of an organic tertiary base. 21-Amino-acetates of saturated and unsaturated 21-hydroxy-pregnane compounds are prepared by reacting the 21-chloracetates prepared by the above process with amines containing no hydroxyl groups in the presence of an inert solvent. The 21-hydroxy-pregnane compound and the chloracetic anhydride are preferably reacted in equimolecular proportions, e.g. in an inert solvent such as ether. A suitable organic tertiary base is pyridine. The reaction with the chloracetic anhydride is preferably carried out at a temperature between -10 DEG and +30 DEG C. The inert solvent used in the reaction between the 21-chloracetate and the amine should preferably have a boiling point between 30 DEG and 120 DEG C., e.g. tetrahydrofuran. The amine used to form the 21-amino-acetate may be a secondary amine such as morpholine, piperidine, diethylamine or methylpiperazine. The 21-hydroxy-pregnane reactant may be a 21-hydroxy-pregnane having a saturated ring system or an unsaturated ring A and/or ring B-particularly a 3-keto-21-hydroxy-pregnane having a saturated or unsaturated ring A such as hydrocortisone, 21-hydroxy-pregnane-3,20-dione and D 1,4-pregnadiene-3,20-11,17,21-triol and the corresponding compounds unsubstituted in the 11-position or containing a keto group in the 11-position. The 21-aminoacetates may be converted into a therapeutically acceptable acid addition product with an acid, e.g. hydrochloric acid. In the examples there are prepared the 21-chloracetates of 21-hydroxy-pregnane-3,20-dione, hydrocortisone, prednisolone and 9-fluoro-hydrocortisone, the 21-diethylamino-acetate, 21-piperidinoacetate, 21-morpholino-acetate, and 21-(N-methyl-piperazino)-acetate of hydrocortisone and the hydrochloride salts thereof, the 21-diethyl-amino-acetate, 21-piperidino-acetate and 21-morpholino-acetate of 21-hydroxypregnane-3,20-dione and the hydrochloride salts thereof, the 21-morpholino-acetate and the 21-piperidino-acetate of prednisolone and the hydrochloride salts thereof, and the 21-piperidino-acetate and 21-(N-methylpiperazino)- acetate of 9-fluorohydrocortisone. Specification 862,370 is referred to.
GB6977/58A 1957-04-04 1958-03-04 Process for the manufacture of chloracetates and aminoacetates of saturated and unsaturated 21-hydroxy-pregnane compounds and acid addition products of the aminoacetates Expired GB879208A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE566473X 1957-04-04

Publications (1)

Publication Number Publication Date
GB879208A true GB879208A (en) 1961-10-04

Family

ID=6818888

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6977/58A Expired GB879208A (en) 1957-04-04 1958-03-04 Process for the manufacture of chloracetates and aminoacetates of saturated and unsaturated 21-hydroxy-pregnane compounds and acid addition products of the aminoacetates

Country Status (2)

Country Link
BE (1) BE566473A (en)
GB (1) GB879208A (en)

Also Published As

Publication number Publication date
BE566473A (en) 1958-04-30

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