GB1224551A - Steroid-butenolides - Google Patents

Steroid-butenolides

Info

Publication number
GB1224551A
GB1224551A GB00638/68A GB1063868A GB1224551A GB 1224551 A GB1224551 A GB 1224551A GB 00638/68 A GB00638/68 A GB 00638/68A GB 1063868 A GB1063868 A GB 1063868A GB 1224551 A GB1224551 A GB 1224551A
Authority
GB
United Kingdom
Prior art keywords
steroid
butenolides
formula
carboxymethylene
lactone
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
GB00638/68A
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 GB1224551A publication Critical patent/GB1224551A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/58—One oxygen atom, e.g. butenolide
    • 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
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
    • C07J53/002—Carbocyclic rings fused
    • C07J53/004—3 membered carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,224,551. Steroid-butenolides. SCHERING A.G. 5 March, 1968 [10 March, 1967 (3); 27 Dec., 1967], No. 10638/68. Heading C2U. Steroid butenolides of the formula (where R 1 is a substituted or unsubstituted steroid nucleus and R 2 is H or R 1 , R 2 and the 4- and 5-carbon atoms of the butenolide ring together represent a substituted or unsubstituted steroid nucleus; and R 3 is H or C 1- 4 alkyl) are prepared by reacting an α-ketolacylate of the formula where X is -P#(C 6 H 5 ) 3 Br# or -PO(O-alkyl) 2 with a base in an inert solvent. Novel products have the formula (in which C 2 #--- C 1 is a single or double carbon bond; Z 1 , Z 2 and Z 4 are each H or OH, and Z 2 may be replaced by a #<SP>14</SP> double bond; and Z 3 and Z 5 are each H or CH 3 ; but Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are not all H) but exclude 3-oxo-4,14, 20(22)-cardatrienolide. Other novel products are 3 - carboxymethylene - 5α - cholestan - 2α- ol - 3# # 2 - lactone and 16 - carboxymethylene - estradiol - 3 - methyl ether - 16# # 17-lactone. The preparation of the starting materials is described in Specification 1,224,552.
GB00638/68A 1967-03-10 1968-03-05 Steroid-butenolides Expired GB1224551A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DESC040364 1967-03-10
DE1967SC040362 DE1643012B2 (en) 1967-03-10 1967-03-10 PROCESS FOR THE MANUFACTURING OF BUTENOLIDES
DE1967SC040363 DE1643013B2 (en) 1967-03-10 1967-03-10 PROCESS FOR THE MANUFACTURING OF BUTENOLIDES
DE1967SC041751 DE1643055B2 (en) 1967-03-10 1967-12-27 METHOD FOR MANUFACTURING CARDENOLIDS

Publications (1)

Publication Number Publication Date
GB1224551A true GB1224551A (en) 1971-03-10

Family

ID=27437418

Family Applications (2)

Application Number Title Priority Date Filing Date
GB26220/70A Expired GB1224552A (en) 1967-03-10 1968-03-05 Phosphorus-containing steroid alpha-ketol acylates
GB00638/68A Expired GB1224551A (en) 1967-03-10 1968-03-05 Steroid-butenolides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB26220/70A Expired GB1224552A (en) 1967-03-10 1968-03-05 Phosphorus-containing steroid alpha-ketol acylates

Country Status (9)

Country Link
AT (1) AT293631B (en)
BE (1) BE711911A (en)
CH (1) CH572947A5 (en)
DE (3) DE1643012B2 (en)
DK (1) DK120744B (en)
FR (1) FR1555396A (en)
GB (2) GB1224552A (en)
NL (1) NL6803407A (en)
SE (2) SE360356B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4221538C1 (en) * 1992-07-01 1994-03-31 Sigma Tau Ind Farmaceuti 14-deoxy-14alpha-cardenolide-3beta-thio derivatives
IT1282289B1 (en) * 1995-06-23 1998-03-16 Sigma Tau Ind Farmaceuti 17-HYDROXYIMINOALKYL AND 17-HYDROXYIMINOMETHYLALKENYL CYCLOPENT FOR HYDROPHENANTRENES ACTIVE ON THE CARDIOVASCULAR SYSTEM,

Also Published As

Publication number Publication date
BE711911A (en) 1968-09-09
CH572947A5 (en) 1976-02-27
DE1643013B2 (en) 1976-07-08
AT293631B (en) 1971-10-25
DE1643013A1 (en) 1971-11-18
DE1643012B2 (en) 1976-07-08
FR1555396A (en) 1969-01-24
DE1643012A1 (en) 1971-05-13
DE1643014B2 (en) 1976-03-04
DK120744B (en) 1971-07-12
DE1643055A1 (en) 1971-05-13
DE1643014A1 (en) 1971-07-08
SE338041B (en) 1971-08-30
GB1224552A (en) 1971-03-10
SE360356B (en) 1973-09-24
NL6803407A (en) 1968-09-11
DE1643055B2 (en) 1976-07-22

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee