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US2228397A - Esters of compounds of the estrone series and process of making same - Google Patents

Esters of compounds of the estrone series and process of making same Download PDF

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Publication number
US2228397A
US2228397A US155824A US15582437A US2228397A US 2228397 A US2228397 A US 2228397A US 155824 A US155824 A US 155824A US 15582437 A US15582437 A US 15582437A US 2228397 A US2228397 A US 2228397A
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United States
Prior art keywords
estrone
esters
compounds
series
acid
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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 - Lifetime
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US155824A
Inventor
Miescher Karl
Scholz Caesar
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.)
CIBA PHARM PROD Inc
CIBA PHARMACEUTICAL PRODUCTS Inc
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CIBA PHARM PROD Inc
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Publication of US2228397A publication Critical patent/US2228397A/en
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Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Definitions

  • This invention relates tothe manufacture of new esters of compounds of the estrone series by causing such a compound to react with an acylating agent of the fatty acid series, the acid residue in which contains 5-8 carbon atoms.
  • Suitable acylating agents are, for example, the fatty acids themselves or their anhydrides, halides or esters formed with alcohols of low molecular weight (re-esterification).
  • the fatty acids used may be of straight chain or branched chain, saturated or unsaturated.
  • the acid component may be a valerianic acid or the like.
  • estrone Among the compounds of the estrone series suitable for the invention may be named estrone,
  • a solution of 1 part of estrone in 3 parts of 25 dry pyridine is mixed in the cold with 1 part of n-valerianic acid chloride.
  • the whole is kept for some time at room temperature.
  • the partially solidified mass is now poured into a diluted sulfuric acid solution; the whole is extracted with Application July 26, 1937, Serial In Switzerland July 30, 1936 ether and the ethereal solution is washed with dilute sulfuric acid, sodium carbonate solution and water.
  • the residue left on the evaporation of the ether is recrystallized from hexane and dilute acetone; the estrone-n-valerate thus obtained melts at 103-105 C.
  • valerianic acid chloride instead of valerianic acid chloride another halide of the acid, for instance, the bromide, may be used.
  • acylating agents there may also be used compounds which contain the radical of angelic acid, iso-valerianic acid, capronic acid, caprylic acid, and the like.
  • esters of equiline and equilenine may also be obtained.
  • reaction may also occur in the presence of another tertiary base, for example, dimethylaniline, quinoline or the like, or even in the absence of a base.
  • another tertiary base for example, dimethylaniline, quinoline or the like, or even in the absence of a base.
  • the fatty esters of compounds selected from the group consisting of estrone, equiline and equilenine, the fatty acid residue in which contains 5 to 8 carbon atoms.

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

Description

Patented Jan. 14, 1941 UNITED STATES PATENT OFFICE ESTERS OF COMPOUNDS OF THE ESTRONE SERIES AND PROCESS OF llIAKING SAME New Jersey No Drawing.
\ 3 Claims.
This invention relates tothe manufacture of new esters of compounds of the estrone series by causing such a compound to react with an acylating agent of the fatty acid series, the acid residue in which contains 5-8 carbon atoms.
Suitable acylating agents are, for example, the fatty acids themselves or their anhydrides, halides or esters formed with alcohols of low molecular weight (re-esterification). The fatty acids used may be of straight chain or branched chain, saturated or unsaturated. The acid component may be a valerianic acid or the like.
Among the compounds of the estrone series suitable for the invention may be named estrone,
equiline or equilenine.
A solution of 1 part of estrone in 3 parts of 25 dry pyridine is mixed in the cold with 1 part of n-valerianic acid chloride. The whole is kept for some time at room temperature. The partially solidified mass is now poured into a diluted sulfuric acid solution; the whole is extracted with Application July 26, 1937, Serial In Switzerland July 30, 1936 ether and the ethereal solution is washed with dilute sulfuric acid, sodium carbonate solution and water. The residue left on the evaporation of the ether is recrystallized from hexane and dilute acetone; the estrone-n-valerate thus obtained melts at 103-105 C.
Instead of valerianic acid chloride another halide of the acid, for instance, the bromide, may be used.
As acylating agents there may also be used compounds which contain the radical of angelic acid, iso-valerianic acid, capronic acid, caprylic acid, and the like.
In an analogous manner there may also be obtained the esters of equiline and equilenine.
The reaction may also occur in the presence of another tertiary base, for example, dimethylaniline, quinoline or the like, or even in the absence of a base.
What we claim is:
1. The fatty esters of compounds selected from the group consisting of estrone, equiline and equilenine, the fatty acid residue in which contains 5 to 8 carbon atoms.
2. The estrone-n-capronate.
3. The estrone-n-caprylate.
KARL MIESCHER. CAESAR SCHOLZ.
US155824A 1936-07-30 1937-07-26 Esters of compounds of the estrone series and process of making same Expired - Lifetime US2228397A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH2228397X 1936-07-30

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US2228397A true US2228397A (en) 1941-01-14

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2597723A (en) * 1948-07-16 1952-05-20 Ayerst Mckenna & Harrison Equilin-3-monosulfate and alkaline salts thereof
US2597471A (en) * 1948-07-20 1952-05-20 Ayerst Mckenna & Harrison Equilenin-3-monosulfate and alkaline salts thereof
US2840508A (en) * 1951-05-17 1958-06-24 Schering Ag Injectable steroid hormone preparations and method of making same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2597723A (en) * 1948-07-16 1952-05-20 Ayerst Mckenna & Harrison Equilin-3-monosulfate and alkaline salts thereof
US2597471A (en) * 1948-07-20 1952-05-20 Ayerst Mckenna & Harrison Equilenin-3-monosulfate and alkaline salts thereof
US2840508A (en) * 1951-05-17 1958-06-24 Schering Ag Injectable steroid hormone preparations and method of making same

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