[go: up one dir, main page]

GB536621A - Manufacture of saturated or unsaturated 17-oxy-20-keto-pregnanones or homologues or derivatives thereof - Google Patents

Manufacture of saturated or unsaturated 17-oxy-20-keto-pregnanones or homologues or derivatives thereof

Info

Publication number
GB536621A
GB536621A GB30404/39A GB3040439A GB536621A GB 536621 A GB536621 A GB 536621A GB 30404/39 A GB30404/39 A GB 30404/39A GB 3040439 A GB3040439 A GB 3040439A GB 536621 A GB536621 A GB 536621A
Authority
GB
United Kingdom
Prior art keywords
oxy
pregnene
diol
keto
methyl
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
GB30404/39A
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.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB536621A publication Critical patent/GB536621A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

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

Abstract

536,621. Pregnone derivatives. SOC. OF CHEMICAL INDUSTRY IN BASLE. Nov. 20, 1939, Nos. 30404 and 30405. Convention dates, Nov. 19, 1938, and Oct. 24, 1939. [Class 2 (iii)] 17-Oxy-20-keto-pregnanones are produced from the corresponding 17-oxy-pregnanolene or 17-oxy-pregnandiol by treatment with an Oxidizing agent. It is preferred that the 17-oxy group and nuclear double linkings, if these are present, should be protected intermediately during the oxidation by conversion into an ester or an ether group or by the action of halogen respectively. As oxidizing agents there may be used any agents known for the purpose of converting a hydroxy group into a keto group. Agents mentioned include chromic acid in glacial acetic acid, metals and metal oxides. such as copper powder and cupric oxide. Biochemical oxidation and the interchange of oxidation stages with carbonyl compounds in the presence of catalysts such as metal alcoholates and metal acylates. In examples, (1) A <SP>5</SP>-pregnene-3:17 -diol-20-one-17 -monoacetate is treated with aluminium tertiary butylate in a mixture of acetone and benzene. The resulting 17-oxy-progesterone acetate is purified by chromatographic separation and saponified by alcoholic potassium hydroxide, to give 17-oxyprogesterone which may also be obtained starting with free A <SP>5</SP>-pregnene-3:17-diol-20-one. In a similar manner #<SP>4</SP>-21-methyl-17-oxypregnene-3:20-dione may be obtained. Another compound mentioned as starting material is # <SP>5</SP> - 3 trans-acetoxy -17 - benzoxy - pregnene - 20 - one. (2) #<SP>4</SP>-pregnene-17:20-diol-3-one-17-acetate is oxidized with chromic acid in glacial acetic acid solution for 24À hours at room temperature to give 17-oxy-progesterone acetate (3) # <SP>5</SP>-pregnene-3:17:20-triol is heated with aluminium isopropylate in a mixture of toluene and cyclohexanone to give 17-oxy-progesterone. By starting from 21-methyl-pregnone-3:17:20- triol there is obtained 21-methyl-pregnane-17- ol:3:20-dione.
GB30404/39A 1938-11-19 1939-11-20 Manufacture of saturated or unsaturated 17-oxy-20-keto-pregnanones or homologues or derivatives thereof Expired GB536621A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH536621X 1938-11-19

Publications (1)

Publication Number Publication Date
GB536621A true GB536621A (en) 1941-05-21

Family

ID=4518813

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30404/39A Expired GB536621A (en) 1938-11-19 1939-11-20 Manufacture of saturated or unsaturated 17-oxy-20-keto-pregnanones or homologues or derivatives thereof

Country Status (1)

Country Link
GB (1) GB536621A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2671793A (en) * 1949-09-19 1954-03-09 Syntex Sa 17 alpha-hydroxy allopregnane-diones and process
US2753360A (en) * 1953-12-12 1956-07-03 Schering A G Fa Esters of 17alpha-hydroxyprogesterone
US2888470A (en) * 1953-08-18 1959-05-26 Syntex Sa Cyclopentanophenanthrene derivatives and process

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2671793A (en) * 1949-09-19 1954-03-09 Syntex Sa 17 alpha-hydroxy allopregnane-diones and process
US2888470A (en) * 1953-08-18 1959-05-26 Syntex Sa Cyclopentanophenanthrene derivatives and process
US2753360A (en) * 1953-12-12 1956-07-03 Schering A G Fa Esters of 17alpha-hydroxyprogesterone

Similar Documents

Publication Publication Date Title
GB556734A (en) Manufacture of compounds of the ring-d-homo-steroid series
GB536621A (en) Manufacture of saturated or unsaturated 17-oxy-20-keto-pregnanones or homologues or derivatives thereof
GB1031076A (en) Novel unsaturated aldehydes
US2365292A (en) Saturated and unsaturated 17-oxy-17-acyl-androstanones and derivatives thereof and process of making same
GB1472922A (en) Pregnanoic acid derivatives
US2372440A (en) Process for the manufacture of compounds of the cyclopentano-polyhydrophenanthrene series
GB506859A (en) Process for the manufacture of alcohols of the cyclopentanopolyhydrophenanthrene series
US2398709A (en) Hydroxycholanic acids
GB1206873A (en) 7alpha-METHYL-ANDROSTENE COMPOUNDS
GB467376A (en) Process for the manufacture of unsaturated neutral oxidation products of stigmasterol compounds
US2341594A (en) Manufacture of pregnendione from iso-pregnenolone and intermediates obtained thereby
CH228644A (en) Process for the preparation of 17-oxy-progesterone.
GB674300A (en) Manufacture of pregnanes
US2177355A (en) 7-keto cholesteryl halide and process of making it
GB508305A (en) Process for the manufacture of pregnendione
GB957221A (en) Novel steroid compounds and processes for their preparation
GB935610A (en) 3ªá-amino-pregnane compounds
GB517078A (en) Manufacture of derivatives of the saturated and unsaturated cyclopentanopolyhydrophenanthrene series
GB554303A (en) Manufacture of saturated and unsaturated androstane-17-ol-ones or esters or ethers thereof
GB506515A (en) Manufacture of oxidation products from sterols or bile acids
US2237410A (en) Pregnanolones and method for producing the same from pregnandiones
Morreal Synthesis of androst-4-en-3β-ol-11, 17-dione
GB556735A (en) Manufacture of new ketones of ring-d-homo-steroids
GB554337A (en) Manufacture of saturated and unsaturated pregnane-polycarbonyl compounds and substitution products thereof
GB523696A (en) Derivatives of the cyclopentano-dimethyl-polyhydro-phenanthrene series