GB1235742A - 01beta-METHYL-19-NORPREGNENE COMPOUNDS - Google Patents
01beta-METHYL-19-NORPREGNENE COMPOUNDSInfo
- Publication number
- GB1235742A GB1235742A GB58044/68A GB5804468A GB1235742A GB 1235742 A GB1235742 A GB 1235742A GB 58044/68 A GB58044/68 A GB 58044/68A GB 5804468 A GB5804468 A GB 5804468A GB 1235742 A GB1235742 A GB 1235742A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- methyl
- ones
- prepared
- chloro
- 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
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J61/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one or two atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,235,742. 11# - Methyl - 19 - norpregnene compounds. G. D. SEARLE & CO. 6 Dec., 1968 [8 Dec., 1967], No. 58044/68. Heading C2U. Novel steroids of the formula (wherein R is H, CHO or C 2-7 alkanoyl; R<SP>1</SP> is C 1-7 alkyl; R<SP>11</SP> is O or H (#-OH or #-Oacyl), where acyl is C 2-7 alkanoyl; Y is H, Cl or CH 3 ; X is H 2 or, when ring B is saturated and contains no substituent, =CH 2 ; and the #<SP>6</SP> double bond is optional) are prepared from 3-alkoxy- 13#-alkyl - 17α - ethyl - 17# - hydroxy - 11#- methylgona - 1,3,5(10) - trienes by known methods. Thus, dehydration to the 17(20)- dehydro compounds, hydroxylation to the 17α,20-diols, Birch reduction to the 2,5(10)- dien-3-enol ethers, hydrolysis to the #<SP>4</SP>-3-ones and 20-oxidation gives the 17α-hydroxy-#<SP>4</SP>-3,20- diones which may then be acylated, either by conventional processes which may necessitate hydrolysis of any #<SP>3</SP>'<SP>5</SP>-3-enol acylate formed or directly using as acylating agent the complex formed from a metalloid halide, an organic acid halide and a halogenated aliphatic solvent and conducting the reaction in the presence of a lower nitroparaffin of high dielectric constant and under anhydrous conditions. In another process the 20-hydroxy group of the abovementioned 17α,20-diols is oxidized and the resulting 20-ones are ketalized before Birch reduction, after which they may be hydrolysed directly to product 17α-hydroxy-#<SP>4</SP>-3,20-diones or acylated and then hydrolysed to 17α-acyloxy- #<SP>4</SP>-3,20-diones. The 16-methylene derivatives are prepared from 3-alkoxy-11#-methyl-19- norpregna - 1,3,5(10),16 - tetraen - 20 - ones by conversion to 16α,17#-pyrazolines, pyrolysis of these to 16-methyl-#<SP>16</SP>-compounds, peroxidation of these, cleavage of the 16α,17α-epoxides with strong acids to give 16-methylene-17α-ols, and then Birch reducing and hydrolysing these and oxidizing the 20-ol products which may then be 17-acylated. 6-Dehydro compounds are prepared by conversion of the #<SP>4</SP>-3-ones to #<SP>3,5</SP>-3- enol ethers and then oxidation of these, e.g. with manganese dioxide reagent or dichlorodicyanobenzoquinone; while 6α-methyl derivatives are prepared by subjecting these enol ethers to the Vilsmeier reagent to afford the corresponding 6-iminium intermediates, hydrolysing these to the 6-formyl compounds, reducing these to the 6-hydroxymethyl compounds, hydrolysing and dehydrogenating to the 6- methylene - #<SP>4</SP> - 3 - ones, hydrogenating these to the 6#-methyl compounds and epimerizing these; alternatively the 6-formyl derivatives may be converted directly to the 6α-methyl-#<SP>4</SP>- 3-ones by reduction and acid treatment. The 6 - methyl - #<SP>6</SP> - compounds are prepared from the 6-methylene compounds by isomerization. The 6α-chloro compounds are prepared from the above-mentioned enol ethers by treatment with HOCl or an agent liberating it and epimerization of the 6#-chloro-#<SP>4</SP>-3-ones thus-produced. The 6 - chloro - #<SP>4,6</SP> compounds are prepared (a) by direct dehydrogenation of the 6α-chloro-#<SP>4</SP>- compounds; or (b) via the 3-enol ethers as described above for the 6-methyl compounds; or (c) by converting the 3-keto-#<SP>4,6</SP>-compounds to 6α,7α-epoxides, adding on HCl to give the the 6# - chloro - 7α - hydroxy compounds, and dehydrating these. The 3#-ols are prepared by reduction of the 3-ones; they may subsequently be acylated. Starting materials which are racemates may be resolved by standard procedures.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68898867A | 1967-12-08 | 1967-12-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1235742A true GB1235742A (en) | 1971-06-16 |
Family
ID=24766615
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB58044/68A Expired GB1235742A (en) | 1967-12-08 | 1968-12-06 | 01beta-METHYL-19-NORPREGNENE COMPOUNDS |
Country Status (17)
Country | Link |
---|---|
AT (4) | AT301055B (en) |
BE (1) | BE725078A (en) |
CH (3) | CH503008A (en) |
CY (1) | CY756A (en) |
DE (1) | DE1813083B2 (en) |
DK (1) | DK124882B (en) |
ES (5) | ES361100A1 (en) |
FI (1) | FI45552C (en) |
FR (1) | FR8324M (en) |
GB (1) | GB1235742A (en) |
IE (1) | IE32820B1 (en) |
IL (1) | IL31232A (en) |
MY (1) | MY7400268A (en) |
NL (1) | NL155556B (en) |
NO (1) | NO129570B (en) |
SE (3) | SE345263B (en) |
YU (2) | YU33974B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015075693A1 (en) * | 2013-11-25 | 2015-05-28 | Richter Gedeon Nyrt. | Process for the synthesis of (11 beta.17alpha)-17-acetoxy-1 1 -methyl-19-norpregn-4-en-3.20-dione |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH606088A5 (en) * | 1970-07-29 | 1978-10-13 | Richter Gedeon Vegyeszet | |
CN109575098B (en) * | 2019-01-18 | 2021-01-01 | 湖南成大生物科技有限公司 | Synthetic method of norgestimate |
-
1968
- 1968-12-05 ES ES361100A patent/ES361100A1/en not_active Expired
- 1968-12-05 FI FI683505A patent/FI45552C/en active
- 1968-12-06 FR FR177069A patent/FR8324M/fr not_active Expired
- 1968-12-06 NO NO04896/68A patent/NO129570B/no unknown
- 1968-12-06 YU YU2873/68A patent/YU33974B/en unknown
- 1968-12-06 CH CH3371A patent/CH503008A/en not_active IP Right Cessation
- 1968-12-06 AT AT684570A patent/AT301055B/en not_active IP Right Cessation
- 1968-12-06 DE DE1813083A patent/DE1813083B2/en active Granted
- 1968-12-06 AT AT684770A patent/AT297955B/en not_active IP Right Cessation
- 1968-12-06 GB GB58044/68A patent/GB1235742A/en not_active Expired
- 1968-12-06 CH CH1830968A patent/CH503004A/en not_active IP Right Cessation
- 1968-12-06 AT AT1192368A patent/AT293634B/en not_active IP Right Cessation
- 1968-12-06 BE BE725078D patent/BE725078A/xx unknown
- 1968-12-06 CH CH3471A patent/CH503009A/en not_active IP Right Cessation
- 1968-12-06 IL IL31232A patent/IL31232A/en unknown
- 1968-12-06 AT AT684670A patent/AT297954B/en not_active IP Right Cessation
- 1968-12-06 DK DK599568AA patent/DK124882B/en unknown
- 1968-12-06 SE SE16706/68A patent/SE345263B/xx unknown
- 1968-12-06 SE SE11170/71A patent/SE365210B/xx unknown
- 1968-12-06 SE SE11171/71A patent/SE365211B/xx unknown
- 1968-12-09 NL NL6817626.A patent/NL155556B/en unknown
- 1968-12-09 IE IE1496/68A patent/IE32820B1/en unknown
-
1970
- 1970-04-30 ES ES70379194A patent/ES379194A1/en not_active Expired
- 1970-04-30 ES ES379195A patent/ES379195A1/en not_active Expired
- 1970-04-30 ES ES379193A patent/ES379193A1/en not_active Expired
- 1970-04-30 ES ES379196A patent/ES379196A1/en not_active Expired
-
1974
- 1974-09-18 CY CY75674A patent/CY756A/en unknown
- 1974-12-30 MY MY268/74A patent/MY7400268A/en unknown
-
1975
- 1975-03-17 YU YU652/75A patent/YU34301B/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015075693A1 (en) * | 2013-11-25 | 2015-05-28 | Richter Gedeon Nyrt. | Process for the synthesis of (11 beta.17alpha)-17-acetoxy-1 1 -methyl-19-norpregn-4-en-3.20-dione |
Also Published As
Publication number | Publication date |
---|---|
CH503009A (en) | 1971-02-15 |
IE32820B1 (en) | 1973-12-12 |
ES379194A1 (en) | 1972-09-01 |
BE725078A (en) | 1969-06-06 |
CH503008A (en) | 1971-02-15 |
FR8324M (en) | 1970-12-07 |
SE365210B (en) | 1974-03-18 |
YU287368A (en) | 1978-02-28 |
NO129570B (en) | 1974-04-29 |
AT297954B (en) | 1972-04-25 |
AT297955B (en) | 1972-04-25 |
ES379196A1 (en) | 1972-09-01 |
SE345263B (en) | 1972-05-23 |
ES379193A1 (en) | 1972-09-01 |
DE1813083A1 (en) | 1969-10-02 |
CY756A (en) | 1974-09-18 |
DE1813083C3 (en) | 1974-09-19 |
SE365211B (en) | 1974-03-18 |
IL31232A (en) | 1972-12-29 |
CH503004A (en) | 1971-02-15 |
YU34301B (en) | 1979-04-30 |
AT301055B (en) | 1972-08-25 |
NL6817626A (en) | 1969-06-10 |
IE32820L (en) | 1969-06-08 |
MY7400268A (en) | 1974-12-31 |
FI45552B (en) | 1972-04-04 |
AT293634B (en) | 1971-10-25 |
FI45552C (en) | 1972-07-10 |
NL155556B (en) | 1978-01-16 |
YU65275A (en) | 1978-10-31 |
ES379195A1 (en) | 1972-09-01 |
ES361100A1 (en) | 1970-10-16 |
DE1813083B2 (en) | 1974-02-07 |
IL31232A0 (en) | 1969-02-27 |
YU33974B (en) | 1978-09-08 |
DK124882B (en) | 1972-12-04 |
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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 |