GB1145645A - Novel pregnane derivatives - Google Patents
Novel pregnane derivativesInfo
- Publication number
- GB1145645A GB1145645A GB40674/68A GB4067468A GB1145645A GB 1145645 A GB1145645 A GB 1145645A GB 40674/68 A GB40674/68 A GB 40674/68A GB 4067468 A GB4067468 A GB 4067468A GB 1145645 A GB1145645 A GB 1145645A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromo
- methyl ester
- pregnane
- carboxylic acid
- acid methyl
- 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
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- 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
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- 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
1,145,645. Pregnane derivatives. F. HOFFMANNLA ROCHE & CO. A.G. 12 Aug., 1966 [8 Oct., 1965; 28 Jan., 1966], No. 40674/68. Divided out of 1,145,641. Heading C2U. The novel pregnane derivatives 2α-bromo- 5α,6# - dihydroxy - pregnan - 3 - one 20 - carboxylic acid methyl ester, 2α-bromo-3#,5α,6#- trihydroxy - pregnane 20 - carboxylic acid methyl ester and the triacetate of the latter derivative are prepared by reacting 5α,6#-dihydroxy - pregnan - 3 - one 20 - carboxylic acid methyl ester with bromine to yield 2α-bromo- 5α,6# - dihydroxy - pregnan - 3 - one 20 - carboxylic acid methyl ester, this can be reduced using lithium tritertbutoxy aluminium hydride and the resulting 2α - bromo - 3#,5α,6# - trihydroxy - pregnane 20 - carboxylic acid methyl ester can be converted into its 3,5,6- triacetate by treatment with acetic anhydride and paratoluene sulphonic acid. The novel pregnane derivatives 2α-bromo- 5α - pregnane - 3,6 - dione 20 - carboxylic acid methyl ester, 2α - bromo - 5α - pregnane - 3# - ol- 6 - one 20 - carboxylic acid methyl ester and 2α- bromo - 3# acetoxy - 5α - pregnan - 6 - one 20- carboxylic acid methyl ester are prepared by reacting 5α-pregnane-3,6-dione 20 - carboxylic aeid methyl ester with bromine to yield 2α- bromo - 5α - pregnane - 3,6 - dione 20 - carboxylic acid methyl ester, this can be reduced with lithium tritertbutoxy aluminium hydride and the resulting 2a-bromo-5α-pregnan-3#-ol- 6-one 20-carboxylic acid methyl ester can be converted into 2α-bromo-3#-acetoxy-5α-pregnan-6-one by treatment with acetic anhydride in the presence of pyridine. The novel pregnane derivative 2α-bromo-20- hydroxy - methyl - 5α - pregnan - 3# - ol - 6 - one 3,22-diacetate is prepared by reacting 20- hydroxymethyl - 6α - pregnane 3,6 - dione with bromine, the reaction product can be reduced with lithium tritertbutoxy aluminium hydride and the reduction product can be treated with acetic anhydride in the presence of pyridine.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1143065A CH467760A (en) | 1965-08-13 | 1965-08-13 | Process for the preparation of 5B-H-6-keto steroids |
| CH1390765 | 1965-10-08 | ||
| CH123166 | 1966-01-28 | ||
| CH433666 | 1966-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1145645A true GB1145645A (en) | 1969-03-19 |
Family
ID=27428125
Family Applications (10)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB40677/68A Expired GB1145648A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
| GB40674/68A Expired GB1145645A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
| GB40676/68A Expired GB1145647A (en) | 1965-08-13 | 1966-08-12 | Novel 5-‡-h-6-keto-steroids |
| GB40678/68A Expired GB1145649A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
| GB40673/68A Expired GB1145644A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
| GB40679/68A Expired GB1145650A (en) | 1965-08-13 | 1966-08-12 | A novel pregnane derivative |
| GB40675/68A Expired GB1145646A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
| GB40672/68A Expired GB1145643A (en) | 1965-08-13 | 1966-08-12 | Novel 5-‡-h-6-keto-steroids |
| GB40680/68A Expired GB1145651A (en) | 1965-08-13 | 1966-08-12 | A novel pregnane derivative |
| GB36214/66A Expired GB1145641A (en) | 1965-08-13 | 1966-08-12 | A process for the manufacture of 5-ß-h-6-keto-steroids |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB40677/68A Expired GB1145648A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
Family Applications After (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB40676/68A Expired GB1145647A (en) | 1965-08-13 | 1966-08-12 | Novel 5-‡-h-6-keto-steroids |
| GB40678/68A Expired GB1145649A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
| GB40673/68A Expired GB1145644A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
| GB40679/68A Expired GB1145650A (en) | 1965-08-13 | 1966-08-12 | A novel pregnane derivative |
| GB40675/68A Expired GB1145646A (en) | 1965-08-13 | 1966-08-12 | Novel pregnane derivatives |
| GB40672/68A Expired GB1145643A (en) | 1965-08-13 | 1966-08-12 | Novel 5-‡-h-6-keto-steroids |
| GB40680/68A Expired GB1145651A (en) | 1965-08-13 | 1966-08-12 | A novel pregnane derivative |
| GB36214/66A Expired GB1145641A (en) | 1965-08-13 | 1966-08-12 | A process for the manufacture of 5-ß-h-6-keto-steroids |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT268555B (en) |
| BE (1) | BE685305A (en) |
| BR (1) | BR6681938D0 (en) |
| CH (1) | CH467760A (en) |
| DK (2) | DK122664B (en) |
| ES (1) | ES330192A1 (en) |
| FI (1) | FI43596B (en) |
| GB (10) | GB1145648A (en) |
| IL (1) | IL26262A (en) |
| NL (1) | NL6611383A (en) |
| SE (2) | SE375536B (en) |
-
1965
- 1965-08-13 CH CH1143065A patent/CH467760A/en unknown
-
1966
- 1966-07-29 AT AT729566A patent/AT268555B/en active
- 1966-07-29 SE SE7200223*3A patent/SE375536B/xx unknown
- 1966-07-29 SE SE10329/66A patent/SE342813B/xx unknown
- 1966-08-03 IL IL26262A patent/IL26262A/en unknown
- 1966-08-08 BR BR181938/66A patent/BR6681938D0/en unknown
- 1966-08-10 BE BE685305D patent/BE685305A/xx unknown
- 1966-08-12 DK DK414166AA patent/DK122664B/en unknown
- 1966-08-12 GB GB40677/68A patent/GB1145648A/en not_active Expired
- 1966-08-12 GB GB40674/68A patent/GB1145645A/en not_active Expired
- 1966-08-12 GB GB40676/68A patent/GB1145647A/en not_active Expired
- 1966-08-12 GB GB40678/68A patent/GB1145649A/en not_active Expired
- 1966-08-12 GB GB40673/68A patent/GB1145644A/en not_active Expired
- 1966-08-12 NL NL6611383A patent/NL6611383A/xx unknown
- 1966-08-12 GB GB40679/68A patent/GB1145650A/en not_active Expired
- 1966-08-12 GB GB40675/68A patent/GB1145646A/en not_active Expired
- 1966-08-12 GB GB40672/68A patent/GB1145643A/en not_active Expired
- 1966-08-12 GB GB40680/68A patent/GB1145651A/en not_active Expired
- 1966-08-12 FI FI2120/66A patent/FI43596B/fi active
- 1966-08-12 ES ES0330192A patent/ES330192A1/en not_active Expired
- 1966-08-12 GB GB36214/66A patent/GB1145641A/en not_active Expired
-
1970
- 1970-08-31 DK DK446770AA patent/DK124479B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1145650A (en) | 1969-03-19 |
| FI43596B (en) | 1971-02-01 |
| GB1145651A (en) | 1969-03-19 |
| BE685305A (en) | 1967-02-10 |
| ES330192A1 (en) | 1967-09-01 |
| IL26262A (en) | 1971-05-26 |
| SE375536B (en) | 1975-04-21 |
| CH467760A (en) | 1969-01-31 |
| GB1145643A (en) | 1969-03-19 |
| GB1145648A (en) | 1969-03-19 |
| GB1145644A (en) | 1969-03-19 |
| DK122664B (en) | 1972-03-27 |
| BR6681938D0 (en) | 1973-12-26 |
| SE342813B (en) | 1972-02-21 |
| DK124479B (en) | 1972-10-23 |
| GB1145646A (en) | 1969-03-19 |
| GB1145649A (en) | 1969-03-19 |
| NL6611383A (en) | 1967-02-14 |
| GB1145641A (en) | 1969-03-19 |
| GB1145647A (en) | 1969-03-19 |
| AT268555B (en) | 1969-02-10 |
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