GB1217530A - Novel halogenated steroids and a process for the manufacture thereof - Google Patents
Novel halogenated steroids and a process for the manufacture thereofInfo
- Publication number
- GB1217530A GB1217530A GB37509/68A GB3750968A GB1217530A GB 1217530 A GB1217530 A GB 1217530A GB 37509/68 A GB37509/68 A GB 37509/68A GB 3750968 A GB3750968 A GB 3750968A GB 1217530 A GB1217530 A GB 1217530A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- chloro
- alkyl
- formula
- alkanoyloxy
- 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
-
- 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
- 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
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
1,217,530. 4-Chloro-steroids. F. HOFFMANN-LA ROCHE & CO. A.G. 6 Aug., 1968 [7 Aug., 1967], No. 37509/68. Heading C2U. The invention comprises compounds of formula wherein R<SP>1</SP> is Cl, F, Br or C 1-8 alkyl; Q is OH or C 1-8 alkanoyloxy; and A represents one of the structures: wherein R<SP>2</SP> is H or F; R<SP>3</SP> is H, OH, C 1-8 alkoxy, C 1-8 alkanoyloxy, difluoroacetyl, dichloroacetyl, or C 1-8 alkyl; R<SP>4</SP> is H, C 1-7 alkylidene or C 1-8 alkyl; or R<SP>3</SP> and R<SP>4</SP> together form a group of formula R<SP>5</SP> is H or C 1-8 alkanoyl; R<SP>6</SP> is H, C 1-8 alkyl, or (optically chloro- or bromo-substituted)- mono - unsaturated - C 2-7 - alkenyl or -alkynyl; R<SP>7</SP> is H or CH 3 ; R<SP>8</SP> is H, F, Cl or Br; R<SP>9</SP> is H, OH or a dihydrogen phosphate ester or alkali metal salt thereof, or C 1-8 alkanoyloxy; R<SP>10</SP> is H, α-OH, C 1-7 alkylidene, α-Cl, α-F, α-CH 2 Cl, α-CH 2 F, or C 1-8 alkyl; R<SP>11</SP> is OH or C 1-8 alkanoyloxy; or R<SP>10</SP> and R<SP>11</SP> together represent a group of Formula B; or R<SP>9</SP> and R<SP>11</SP> together represent a group of formula n is 0 or 1; X represents #<SP>1</SP>-unsaturation or a 2-chloro or 1α,2α-methylene group; X<SP>1</SP> and X<SP>2</SP> each represent #<SP>1</SP>-unsaturation or a 2-chloro group (provided that when X<SP>1</SP> represents #<SP>1</SP>- unsaturation, R<SP>7</SP> is CH 3 ); Y is CH 2 , CHOH (α or #), or CO; Z is CO, CHOH (α or #), α-(C 1-7 - alkylsulphonyloxy) - methylene, α - (arylsulphonyloxy)-methylene, or (when R<SP>8</SP> is H and R<SP>9</SP> other than H) CH 2 , or (when R<SP>8</SP> is Cl) #- chloromethylene; or Z and R<SP>8</SP> together represent #<SP>9(11)</SP>-unsaturation or a 9,11-oxido group; and the wavy lines denote either the α- or #- configuration. These compounds are prepared by reduction of the corresponding 3-oxosteroids (wherein any 20-oxo group is sterically protected) followed, when necessary, by alkanoylation of the resulting 3-hydroxy compound and/or cleavage of any protecting group. 4,6 - Dichloro - 17α - acetoxy - 16α - methylpregna - 4,6 - diene - 3,20 - dione is prepared by the action of chlorine on 6-chloro-17α-acetoxy- 16α - methyl - pregna - 4,6 - diene - 3,20 - dione. Other 3-oxo starting compounds are described as in Specification 1,215,752. Stearides of Formula I are said to be progestational, androgenic/anabolic, mineralo-cor ticoid and glucocorticoid (i.e. antiinflammatory and thymolytic) agents, and may be made up with carriers into pharmaceutical compositions suitable for oral, parenteral or topical administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65860267A | 1967-08-07 | 1967-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1217530A true GB1217530A (en) | 1970-12-31 |
Family
ID=24641922
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37509/68A Expired GB1217530A (en) | 1967-08-07 | 1968-08-06 | Novel halogenated steroids and a process for the manufacture thereof |
| GB37510/68A Expired GB1215752A (en) | 1967-08-07 | 1968-08-06 | Novel halogenated steroids and a process for the manufacture thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37510/68A Expired GB1215752A (en) | 1967-08-07 | 1968-08-06 | Novel halogenated steroids and a process for the manufacture thereof |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JPS5021474B1 (en) |
| AT (4) | AT290031B (en) |
| BE (2) | BE719050A (en) |
| CH (10) | CH544073A (en) |
| DE (1) | DE1793063A1 (en) |
| DK (2) | DK126187B (en) |
| ES (2) | ES356956A1 (en) |
| FI (2) | FI45321C (en) |
| FR (4) | FR8417M (en) |
| GB (2) | GB1217530A (en) |
| IE (2) | IE32397B1 (en) |
| IL (2) | IL30491A (en) |
| MY (1) | MY7100216A (en) |
| NL (2) | NL6811217A (en) |
| NO (2) | NO128765B (en) |
| SE (2) | SE351633B (en) |
| YU (2) | YU33190B (en) |
-
1968
- 1968-07-17 CH CH418771A patent/CH544073A/en not_active IP Right Cessation
- 1968-07-17 CH CH418971A patent/CH544074A/en not_active IP Right Cessation
- 1968-07-17 CH CH418871A patent/CH544072A/en not_active IP Right Cessation
- 1968-07-17 CH CH418571A patent/CH541549A/en not_active IP Right Cessation
- 1968-07-17 CH CH419071A patent/CH541550A/en not_active IP Right Cessation
- 1968-07-17 CH CH418671A patent/CH544075A/en not_active IP Right Cessation
- 1968-07-17 CH CH1070568A patent/CH565198A5/xx not_active IP Right Cessation
- 1968-07-17 CH CH1070668A patent/CH555329A/en not_active IP Right Cessation
- 1968-07-17 CH CH419171A patent/CH544081A/en not_active IP Right Cessation
- 1968-07-17 CH CH419271A patent/CH544076A/en not_active IP Right Cessation
- 1968-07-30 DE DE19681793063 patent/DE1793063A1/en active Pending
- 1968-08-05 AT AT08882/69A patent/AT290031B/en not_active IP Right Cessation
- 1968-08-05 YU YU1858/68A patent/YU33190B/en unknown
- 1968-08-05 AT AT760368A patent/AT285832B/en not_active IP Right Cessation
- 1968-08-05 IL IL6830491A patent/IL30491A/en unknown
- 1968-08-05 BE BE719050D patent/BE719050A/xx unknown
- 1968-08-05 AT AT888169A patent/AT290030B/en not_active IP Right Cessation
- 1968-08-05 AT AT760468A patent/AT285833B/en not_active IP Right Cessation
- 1968-08-05 YU YU01857/68A patent/YU185768A/en unknown
- 1968-08-05 IL IL30492A patent/IL30492A/en unknown
- 1968-08-05 BE BE719049D patent/BE719049A/xx unknown
- 1968-08-06 GB GB37509/68A patent/GB1217530A/en not_active Expired
- 1968-08-06 ES ES356956A patent/ES356956A1/en not_active Expired
- 1968-08-06 NO NO03087/68A patent/NO128765B/no unknown
- 1968-08-06 NO NO03088/68A patent/NO128766B/no unknown
- 1968-08-06 JP JP43055307A patent/JPS5021474B1/ja active Pending
- 1968-08-06 FR FR162043A patent/FR8417M/fr not_active Expired
- 1968-08-06 FR FR1588548D patent/FR1588548A/fr not_active Expired
- 1968-08-06 FR FR162042A patent/FR7921M/fr not_active Expired
- 1968-08-06 DK DK379168AA patent/DK126187B/en unknown
- 1968-08-06 ES ES356957A patent/ES356957A1/en not_active Expired
- 1968-08-06 FR FR1588547D patent/FR1588547A/fr not_active Expired
- 1968-08-06 IE IE950/68A patent/IE32397B1/en unknown
- 1968-08-06 GB GB37510/68A patent/GB1215752A/en not_active Expired
- 1968-08-06 IE IE949/68A patent/IE32344B1/en unknown
- 1968-08-06 DK DK379268AA patent/DK122606B/en unknown
- 1968-08-07 FI FI682233A patent/FI45321C/en active
- 1968-08-07 SE SE10631/68A patent/SE351633B/xx unknown
- 1968-08-07 FI FI682234A patent/FI45322C/en active
- 1968-08-07 NL NL6811217A patent/NL6811217A/xx unknown
- 1968-08-07 JP JP43055539A patent/JPS5010859B1/ja active Pending
- 1968-08-07 NL NL6811218A patent/NL6811218A/xx unknown
- 1968-08-07 SE SE10630/68A patent/SE351632B/xx unknown
-
1971
- 1971-12-30 MY MY216/71A patent/MY7100216A/en unknown
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