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FR2281357A1 - Steroid spirolactones esp spironolactone - prepd by decarboxylation of the lactone under neutral aqueous conditions - Google Patents

Steroid spirolactones esp spironolactone - prepd by decarboxylation of the lactone under neutral aqueous conditions

Info

Publication number
FR2281357A1
FR2281357A1 FR7427571A FR7427571A FR2281357A1 FR 2281357 A1 FR2281357 A1 FR 2281357A1 FR 7427571 A FR7427571 A FR 7427571A FR 7427571 A FR7427571 A FR 7427571A FR 2281357 A1 FR2281357 A1 FR 2281357A1
Authority
FR
France
Prior art keywords
spirolactones
spironolactone
prepd
steroid
decarboxylation
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.)
Granted
Application number
FR7427571A
Other languages
French (fr)
Other versions
FR2281357B1 (en
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7427571A priority Critical patent/FR2281357A1/en
Publication of FR2281357A1 publication Critical patent/FR2281357A1/en
Application granted granted Critical
Publication of FR2281357B1 publication Critical patent/FR2281357B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/001—Lactones
    • C07J21/003—Lactones at position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton

Landscapes

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

Abstract

Steroid spirolactones of formula (I): (where R1 is 1-4C linear alkyl, R2 is H or CH3), are prepd. by (1) reacting (II) with (CH3)3S circled positive X circled negative in presence of a base, (2) dehydrogenating the cpd. obtd. (3) treating wtih an alkyl malonate of formula: R4-OCO-CH2-COOR4, (4) treating with a thioalkanoic acid R1COSH, and (5) heating in neutral aq. medium. (R3 is CH3 or C2H5, R4 is 1-4C straight or branched alkyl, X circled negative is Br or I). Cpd. (I, R1=R2=CH3) is a known diuretic (spironolactone) for treating certain cardiac disorders.
FR7427571A 1974-08-08 1974-08-08 Steroid spirolactones esp spironolactone - prepd by decarboxylation of the lactone under neutral aqueous conditions Granted FR2281357A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7427571A FR2281357A1 (en) 1974-08-08 1974-08-08 Steroid spirolactones esp spironolactone - prepd by decarboxylation of the lactone under neutral aqueous conditions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7427571A FR2281357A1 (en) 1974-08-08 1974-08-08 Steroid spirolactones esp spironolactone - prepd by decarboxylation of the lactone under neutral aqueous conditions

Publications (2)

Publication Number Publication Date
FR2281357A1 true FR2281357A1 (en) 1976-03-05
FR2281357B1 FR2281357B1 (en) 1978-07-13

Family

ID=9142250

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7427571A Granted FR2281357A1 (en) 1974-08-08 1974-08-08 Steroid spirolactones esp spironolactone - prepd by decarboxylation of the lactone under neutral aqueous conditions

Country Status (1)

Country Link
FR (1) FR2281357A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003082894A2 (en) * 2002-03-22 2003-10-09 Pharmacia Corporation C-17 spirolactonization and 6,7 oxidation of steroids
CN113461767A (en) * 2020-03-31 2021-10-01 天津药业研究院股份有限公司 Synthesis method of canrenone

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300489A (en) * 1964-07-24 1967-01-24 Smith Kline French Lab Steroidal c-17 spirolactones and processes and intermediates used in the preparation thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300489A (en) * 1964-07-24 1967-01-24 Smith Kline French Lab Steroidal c-17 spirolactones and processes and intermediates used in the preparation thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003082894A2 (en) * 2002-03-22 2003-10-09 Pharmacia Corporation C-17 spirolactonization and 6,7 oxidation of steroids
WO2003082894A3 (en) * 2002-03-22 2004-04-15 Pharmacia Corp C-17 spirolactonization and 6,7 oxidation of steroids
CN113461767A (en) * 2020-03-31 2021-10-01 天津药业研究院股份有限公司 Synthesis method of canrenone

Also Published As

Publication number Publication date
FR2281357B1 (en) 1978-07-13

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