GB1309651A - Process for the preparation of 3-oxo-19 nor-delta 4- steroids via nitrogenous 4,5-secosteroids - Google Patents
Process for the preparation of 3-oxo-19 nor-delta 4- steroids via nitrogenous 4,5-secosteroidsInfo
- Publication number
- GB1309651A GB1309651A GB1563270A GB1563270A GB1309651A GB 1309651 A GB1309651 A GB 1309651A GB 1563270 A GB1563270 A GB 1563270A GB 1563270 A GB1563270 A GB 1563270A GB 1309651 A GB1309651 A GB 1309651A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- alkyl
- compounds
- reaction
- formula
- 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
Links
Classifications
-
- 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
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1309651 Steroid synthesis; 4,5-secosteroids F HOFFMANN-LA ROCHE & CO AG 2 April 1970 [4 April 1969] 15632/70 Headings C2C and C2U The invention comprises compounds of Formulµ VI and VII and a process for preparing compounds of Formula I from compounds of Formula II by reaction sequence ABCDE or ABCDFG in the reaction scheme in which all compounds are d, l or dl, M is the remainder of the D ring of the steroid; R is OH, C 1-7 alkoxy or -NXY where X and Y are each C 1-7 alkyl; R<SP>1</SP> is primary C 1-5 alkyl, R<SP>2</SP>, R<SP>3</SP> and R<SP>5</SP> are each H or C 1-7 alkyl; and R<SP>6</SP> is H, monocyclic aryl- C 1-7 -alkyl, acyl or -CR<SP>7</SP>R<SP>8</SP>R<SP>9</SP> where R<SP>7</SP>, R<SP>8</SP> and R<SP>9</SP> are each C 1-7 alkyl. Reaction sequence A<SP>1</SP>B<SP>1</SP> is alternative to AB but does not form part of the invention and is not exemplified. The reaction steps are effected as follows: (A) heat and/or acid; (A<SP>1</SP>) and (B) hydrogenation with a noble metal catalyst in the presence of a base; (B<SP>1</SP>) heat and acid; (C) reaction with R-NH 2 or a salt thereof; (D) selective oxidation, e.g. with CrO 3 /acetone, metal alkoxide, silver carbonate, or CrO 3 /H 2 SO 4 /N,N-dialkylalkanamide; (E) aqueous acid in an inert watermiscible organic solvent; (F) reaction with a reactive carbonyl compound; e.g. acetone, pyruvic acid or levulinic acid; (G) cyclization which may be acid- or base-catalysed. A 17 oxo group (steroid numbering) in a compound of Formula III may be converted to an =NR group during step (C) and regenerated during step (E) or (G). Alternatively said 17- oxo group may be reduced to a 17#-hydroxy group or converted to a 17α-alkynyl-17#- hydroxy group immediately prior to step C. A 17-hydroxy group in a compound of Formula VI may be converted to an oxo group during step (D). Compounds of Formulµ III and IV comprise the subject-matter of Specification 1,309,652. Reference has been directed by the Comptroller to Specification 1,207,048.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81369369A | 1969-04-04 | 1969-04-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1309651A true GB1309651A (en) | 1973-03-14 |
Family
ID=25213104
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2952172A Expired GB1309652A (en) | 1969-04-04 | 1970-04-02 | 3-alkyl-4-oxa-steroids process for their preparation and hydro genation |
GB1563270A Expired GB1309651A (en) | 1969-04-04 | 1970-04-02 | Process for the preparation of 3-oxo-19 nor-delta 4- steroids via nitrogenous 4,5-secosteroids |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2952172A Expired GB1309652A (en) | 1969-04-04 | 1970-04-02 | 3-alkyl-4-oxa-steroids process for their preparation and hydro genation |
Country Status (13)
Country | Link |
---|---|
JP (2) | JPS5028952B1 (en) |
BE (1) | BE748356A (en) |
CH (1) | CH568336A5 (en) |
DE (1) | DE2015800C3 (en) |
FR (1) | FR2068452B1 (en) |
GB (2) | GB1309652A (en) |
HU (1) | HU163408B (en) |
IE (1) | IE34082B1 (en) |
IL (1) | IL34184A (en) |
NL (1) | NL7004801A (en) |
PL (1) | PL80640B1 (en) |
SE (1) | SE362421B (en) |
SU (1) | SU439089A3 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53146139U (en) * | 1977-04-22 | 1978-11-17 | ||
GB2514589B (en) | 2013-05-30 | 2020-01-29 | Nat Oilwell Varco Lp | Centrifuge for separating solids from solids laden drilling fluid |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH503050A (en) * | 1967-11-02 | 1971-02-15 | Hoffmann La Roche | Process for the preparation of polycyclic compounds |
-
1970
- 1970-03-23 CH CH432570A patent/CH568336A5/xx not_active IP Right Cessation
- 1970-03-27 IL IL34184A patent/IL34184A/en unknown
- 1970-04-02 PL PL1970139756A patent/PL80640B1/en unknown
- 1970-04-02 IE IE412/70A patent/IE34082B1/en unknown
- 1970-04-02 SU SU1419627A patent/SU439089A3/en active
- 1970-04-02 GB GB2952172A patent/GB1309652A/en not_active Expired
- 1970-04-02 BE BE748356D patent/BE748356A/en unknown
- 1970-04-02 GB GB1563270A patent/GB1309651A/en not_active Expired
- 1970-04-02 DE DE2015800A patent/DE2015800C3/en not_active Expired
- 1970-04-03 HU HUHO1276A patent/HU163408B/hu unknown
- 1970-04-03 NL NL7004801A patent/NL7004801A/xx unknown
- 1970-04-03 SE SE04631/70A patent/SE362421B/xx unknown
- 1970-04-03 FR FR707012113A patent/FR2068452B1/fr not_active Expired
- 1970-04-04 JP JP45028973A patent/JPS5028952B1/ja active Pending
-
1972
- 1972-03-16 JP JP47026921A patent/JPS4935626B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
PL80640B1 (en) | 1975-08-30 |
IL34184A (en) | 1973-08-29 |
FR2068452A1 (en) | 1971-08-27 |
SE362421B (en) | 1973-12-10 |
JPS5028952B1 (en) | 1975-09-19 |
FR2068452B1 (en) | 1973-07-13 |
NL7004801A (en) | 1970-10-06 |
BE748356A (en) | 1970-10-02 |
DE2015800A1 (en) | 1970-10-22 |
IE34082L (en) | 1970-10-04 |
IE34082B1 (en) | 1975-01-22 |
GB1309652A (en) | 1973-03-14 |
CH568336A5 (en) | 1975-10-31 |
HU163408B (en) | 1973-08-28 |
JPS4935626B1 (en) | 1974-09-25 |
DE2015800C3 (en) | 1979-06-13 |
IL34184A0 (en) | 1970-05-21 |
DE2015800B2 (en) | 1978-10-19 |
SU439089A3 (en) | 1974-08-05 |
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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 |