IE34082L - 3-oxo-19-nor- delta4-steroids - Google Patents
3-oxo-19-nor- delta4-steroidsInfo
- Publication number
- IE34082L IE34082L IE700412A IE41270A IE34082L IE 34082 L IE34082 L IE 34082L IE 700412 A IE700412 A IE 700412A IE 41270 A IE41270 A IE 41270A IE 34082 L IE34082 L IE 34082L
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- alkyl
- compounds
- reaction
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 abstract 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000003431 steroids Chemical class 0.000 abstract 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 abstract 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract 2
- 229940022682 acetone Drugs 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229940040102 levulinic acid Drugs 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229940107700 pyruvic acid Drugs 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910001958 silver carbonate Inorganic materials 0.000 abstract 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 Formul 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 Formul III and IV comprise the subject-matter of Specification 1,309,652. Reference has been directed by the Comptroller to Specification 1,207,048.
[GB1309651A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81369369A | 1969-04-04 | 1969-04-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34082L true IE34082L (en) | 1970-10-04 |
| IE34082B1 IE34082B1 (en) | 1975-01-22 |
Family
ID=25213104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE412/70A IE34082B1 (en) | 1969-04-04 | 1970-04-02 | A process for the preparation of 3-oxo-19-nor-delta4-steroids via novel nitrogenous 4,5-secosteroids |
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 DE DE2015800A patent/DE2015800C3/en not_active Expired
- 1970-04-02 GB GB2952172A patent/GB1309652A/en not_active Expired
- 1970-04-02 SU SU1419627A patent/SU439089A3/en active
- 1970-04-02 IE IE412/70A patent/IE34082B1/en unknown
- 1970-04-02 PL PL1970139756A patent/PL80640B1/en unknown
- 1970-04-02 GB GB1563270A patent/GB1309651A/en not_active Expired
- 1970-04-02 BE BE748356D patent/BE748356A/en unknown
- 1970-04-03 SE SE04631/70A patent/SE362421B/xx unknown
- 1970-04-03 HU HUHO1276A patent/HU163408B/hu unknown
- 1970-04-03 FR FR707012113A patent/FR2068452B1/fr not_active Expired
- 1970-04-03 NL NL7004801A patent/NL7004801A/xx unknown
- 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 |
|---|---|
| GB1309652A (en) | 1973-03-14 |
| IE34082B1 (en) | 1975-01-22 |
| GB1309651A (en) | 1973-03-14 |
| CH568336A5 (en) | 1975-10-31 |
| HU163408B (en) | 1973-08-28 |
| NL7004801A (en) | 1970-10-06 |
| FR2068452B1 (en) | 1973-07-13 |
| IL34184A0 (en) | 1970-05-21 |
| SU439089A3 (en) | 1974-08-05 |
| PL80640B1 (en) | 1975-08-30 |
| JPS5028952B1 (en) | 1975-09-19 |
| DE2015800C3 (en) | 1979-06-13 |
| DE2015800B2 (en) | 1978-10-19 |
| SE362421B (en) | 1973-12-10 |
| IL34184A (en) | 1973-08-29 |
| BE748356A (en) | 1970-10-02 |
| JPS4935626B1 (en) | 1974-09-25 |
| FR2068452A1 (en) | 1971-08-27 |
| DE2015800A1 (en) | 1970-10-22 |
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