GB1229428A - - Google Patents
Info
- Publication number
- GB1229428A GB1229428A GB1229428DA GB1229428A GB 1229428 A GB1229428 A GB 1229428A GB 1229428D A GB1229428D A GB 1229428DA GB 1229428 A GB1229428 A GB 1229428A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroids
- acyloxy
- methylene
- hydroxy
- pregnene
- 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
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 1
- 230000002280 anti-androgenic effect Effects 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000003152 gestagenic effect Effects 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 230000016087 ovulation Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,229,428. 1,2-Methylene-steroids. SCHERING A.G. 1 April, 1968 [31 March, 1967; 11 Jan., 1968], No. 15526/68. Heading C2U. 17 - Hydroxy - 6#,7# - epoxy - 1α,2α - methylene-4-pregnene-3,20-dione and acylates thereof, which are novel compounds, are prepared by reacting 17-acyloxy-6#-(acyloxy or hydroxy)- 7α-(chloro or bromo) -1α,2α-methylene-4-pregnene-3,20-diones with a base in an inert solvent, and, if desired, when the product is a free 17-ol, acylating this. The starting materials are prepared from the corresponding #<SP>6</SP>-steroids; reaction of these with N-bromo- or N-chloro-succinimide and water in the presence of perchloric acid in dioxan gives the 6#-hydroxy-7#-halogeno-steroids, while reaction with the same halogenating agents and a carboxylic acid in tetrahydrofuran saturated with HCl gives the 6#-acyloxy-7α- halogeno-steroids. The novel steroids are stated to have strong gestagenic activity with little anti-androgenic effect and no ovulation inhibiting effect, and they may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967SC040469 DE1643017B2 (en) | 1967-03-31 | 1967-03-31 | PROCESS FOR THE PRODUCTION OF 6-CHLORO-1,2ALPHA-METHYLENE DELTA HIGH 4,6-PREGNADIENES |
| DESC041823 | 1968-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1229428A true GB1229428A (en) | 1971-04-21 |
Family
ID=25993457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1229428D Expired GB1229428A (en) | 1967-03-31 | 1968-04-01 |
Country Status (10)
| Country | Link |
|---|---|
| AT (2) | AT279818B (en) |
| BE (1) | BE712938A (en) |
| CH (2) | CH564039A5 (en) |
| DE (2) | DE1643017B2 (en) |
| DK (2) | DK116941B (en) |
| FR (2) | FR1579547A (en) |
| GB (1) | GB1229428A (en) |
| NL (2) | NL156706B (en) |
| NO (1) | NO127535B (en) |
| SE (2) | SE331839B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH545777A (en) * | 1971-02-05 | 1974-02-15 |
-
1967
- 1967-03-31 DE DE1967SC040469 patent/DE1643017B2/en active Granted
-
1968
- 1968-01-11 DE DE19681668685 patent/DE1668685C3/en not_active Expired
- 1968-02-26 DK DK75068A patent/DK116941B/en not_active IP Right Cessation
- 1968-03-06 AT AT220568A patent/AT279818B/en not_active IP Right Cessation
- 1968-03-12 AT AT244668A patent/AT301038B/en not_active IP Right Cessation
- 1968-03-22 DK DK126368A patent/DK116208B/en unknown
- 1968-03-26 CH CH450768A patent/CH564039A5/xx not_active IP Right Cessation
- 1968-03-27 CH CH451568A patent/CH548382A/en not_active IP Right Cessation
- 1968-03-28 NL NL6804394A patent/NL156706B/en not_active IP Right Cessation
- 1968-03-28 NL NL686804395A patent/NL155020B/en unknown
- 1968-03-29 SE SE422168A patent/SE331839B/xx unknown
- 1968-03-29 FR FR1579547D patent/FR1579547A/fr not_active Expired
- 1968-03-29 SE SE422068A patent/SE343056B/xx unknown
- 1968-03-29 BE BE712938D patent/BE712938A/xx unknown
- 1968-04-01 GB GB1229428D patent/GB1229428A/en not_active Expired
- 1968-06-27 FR FR156884A patent/FR7900M/fr not_active Expired
-
1969
- 1969-01-10 NO NO101/69A patent/NO127535B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT279818B (en) | 1970-03-25 |
| NL6804395A (en) | 1968-10-01 |
| NL156706B (en) | 1978-05-16 |
| FR1579547A (en) | 1969-08-29 |
| DE1643017A1 (en) | 1971-04-15 |
| DE1668685B2 (en) | 1974-08-29 |
| SE331839B (en) | 1971-01-18 |
| NL6804394A (en) | 1968-10-01 |
| CH564039A5 (en) | 1975-07-15 |
| FR7900M (en) | 1970-05-11 |
| DE1668685C3 (en) | 1975-04-24 |
| CH548382A (en) | 1974-04-30 |
| BE712938A (en) | 1968-09-30 |
| NL155020B (en) | 1977-11-15 |
| DE1668685A1 (en) | 1971-10-07 |
| SE343056B (en) | 1972-02-28 |
| DK116941B (en) | 1970-03-02 |
| DK116208B (en) | 1969-12-22 |
| NO127535B (en) | 1973-07-09 |
| AT301038B (en) | 1972-08-25 |
| DE1643017B2 (en) | 1976-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |