GB1514476A - Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates - Google Patents
Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylatesInfo
- Publication number
- GB1514476A GB1514476A GB38090/74A GB3809074A GB1514476A GB 1514476 A GB1514476 A GB 1514476A GB 38090/74 A GB38090/74 A GB 38090/74A GB 3809074 A GB3809074 A GB 3809074A GB 1514476 A GB1514476 A GB 1514476A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- formula
- steroids
- radical
- alpha
- 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
- -1 haloalkyl androst-4-ene Chemical compound 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 title abstract 2
- ZQCAOHVYAHPGEW-UDCWSGSHSA-N (8s,9s,10r,13s,14s,17s)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthrene-17-carboxylic acid Chemical class C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(O)=O)[C@@H]4[C@@H]3CCC2=C1 ZQCAOHVYAHPGEW-UDCWSGSHSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000005999 2-bromoethyl group Chemical group 0.000 abstract 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000005997 bromomethyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Chemical group 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
Steroids with antiinflammatory activity and the formula I in which R' is methyl, ethyl, n-propyl or isopropyl; R'' is methyl, chloromethyl, fluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl or 2-iodoethyl; X is hydrogen or fluorine; and @ is a single or double bond are prepared by esterifying or transesterifying, respectively, with an agent supplying the radical R'' or the radical R', respectively, a corresponding 17 alpha -acyloxy-17ss-carboxylic acid or a functional derivative thereof or a 17 alpha -hydroxy-17ss-carboxylate. Resulting DELTA <1>-steroids of the formula I can subsequently be reduced to the corresponding saturated compounds or resulting 1,2-saturated compounds can be dehydrogenated to the corresponding DELTA <1> compounds. In addition, halogen substituents present in the group R'' can be replaced by other halogens; thus, for example, compounds of the formula I in which R'' is an alkyl group substituted by chlorine, bromine or iodine can be converted by this exchange reaction to the corresponding fluoroalkyl compounds. The compounds of the formula I are distinguished by very good antiinflammatory activity and can be converted into pharmaceuticals for topical or internal administration. <IMAGE>
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB38090/74A GB1514476A (en) | 1974-08-30 | 1974-08-30 | Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates |
| CH1120375A CH612686A5 (en) | 1974-08-30 | 1975-08-29 | Process for the preparation of steroids of the androstane series |
| FR7526651A FR2282899A1 (en) | 1974-08-30 | 1975-08-29 | ANDROSTANE SERIES STEROIDS, THEIR PREPARATION AND THEIR APPLICATIONS |
| NL7510226A NL7510226A (en) | 1974-08-30 | 1975-08-29 | PROCESS FOR THE PREPARATION OF ANDROSTA DERIVATIVES. |
| BE159583A BE832889A (en) | 1974-08-30 | 1975-08-29 | ANDROSTANE SERIES STEROIDS AND THEIR PREPARATION |
| DK389175AA DK136074B (en) | 1974-08-30 | 1975-08-29 | Analogous process for the preparation of 6alpha-fluoro-11beta-hydroxy-16-methyl-3-oxo-17alpha-acyloxyandrost-4-ene-17beta-carboxylic acid esters. |
| DE19752538595 DE2538595A1 (en) | 1974-08-30 | 1975-08-29 | STEROID CONNECTIONS |
| SE7509651A SE405976B (en) | 1974-08-30 | 1975-08-29 | PROCEDURE FOR THE PRODUCTION OF ANTI-INFLAMMATORY STEROIDS BELONGING TO THE ANDROSTAN SERIES |
| AU84404/75A AU492497B2 (en) | 1975-08-29 | Alkyl and haloalkyl androst-4-ene and androsta-1, 4-diene-17-carboxylates | |
| JP50104825A JPS5148649A (en) | 1974-08-30 | 1975-08-29 | |
| IE1904/75A IE41663B1 (en) | 1974-08-30 | 1975-08-29 | Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene17-carboxylates |
| ZA00755553A ZA755553B (en) | 1974-08-30 | 1975-08-29 | Anti-inflammatory steroids of the androstane series |
| US05/757,325 US4093721A (en) | 1974-08-30 | 1977-01-06 | Pharmaceutical compositions of 6α,9α-difluoro-androst-4-ene-17β-carboxylates and derivatives thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB38090/74A GB1514476A (en) | 1974-08-30 | 1974-08-30 | Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1514476A true GB1514476A (en) | 1978-06-14 |
Family
ID=10401112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38090/74A Expired GB1514476A (en) | 1974-08-30 | 1974-08-30 | Alkyl and haloalkyl androst-4-ene and androsta-1,4-diene-17beta-carboxylates |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5148649A (en) |
| BE (1) | BE832889A (en) |
| CH (1) | CH612686A5 (en) |
| DE (1) | DE2538595A1 (en) |
| DK (1) | DK136074B (en) |
| FR (1) | FR2282899A1 (en) |
| GB (1) | GB1514476A (en) |
| IE (1) | IE41663B1 (en) |
| NL (1) | NL7510226A (en) |
| SE (1) | SE405976B (en) |
| ZA (1) | ZA755553B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003062259A3 (en) * | 2002-01-21 | 2003-08-28 | Glaxo Group Ltd | Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents |
| WO2003072592A1 (en) * | 2002-01-15 | 2003-09-04 | Glaxo Group Limited | 17.alpha-cycloalkyl/cycloylkenyl esters of alkyl-or haloalkyl-androst-4-en-3-on-11.beta.,17.alpha.-diol 17.beta.-carboxylates as anti-inflammatory agents |
| WO2003082896A3 (en) * | 2002-03-29 | 2003-11-20 | Farmabios Srl | A PROCESS FOR THE PREPARATION OF 6α-FLUORO STEROIDS BY ISOMERISATION OF 6β-FLUOROSTEROIDS |
| WO2005005451A1 (en) | 2003-07-11 | 2005-01-20 | Glaxo Group Limited | Specific glucocorticosteroid compound having anti- inflammatory activity |
| US7579335B2 (en) | 2005-01-10 | 2009-08-25 | Glaxo Group Limited | Androstane 17α-carbonate derivatives for use in the treatment of allergic and inflammatory conditions |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH628355A5 (en) * | 1976-02-24 | 1982-02-26 | Ciba Geigy Ag | METHOD FOR PRODUCING NEW ANDROSTADIEN-17BETA-CARBONIC ACIDS AND THEIR ESTERS AND SALTS. |
| CH614960A5 (en) * | 1976-04-15 | 1979-12-28 | Ciba Geigy Ag | |
| DE2809491A1 (en) * | 1977-03-09 | 1978-09-14 | Ciba Geigy Ag | ANTICOCCIDIELLE AND OVO-LARVICIDE MEDIUM |
| NL191792C (en) * | 1980-02-15 | 1996-08-02 | Glaxo Group Ltd | Esters of an androstane-17beta-carbothioic acid, process for the preparation of these esters, and pharmaceutical preparations containing these esters. |
| SE449106B (en) * | 1980-07-10 | 1987-04-06 | Otsuka Pharma Co Ltd | STEROID WITH ANTI-INFLAMMATORY EFFECT AND COMPOSITION CONTAINING THIS |
| US4607028A (en) * | 1983-08-18 | 1986-08-19 | Ciba-Geigy Corporation | Novel carboxylic acid esters |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636010A (en) * | 1968-12-23 | 1972-01-18 | Ciba Geigy Corp | Esters of steroid-17-carboxylic acids |
| GB1384372A (en) * | 1971-01-20 | 1975-02-19 | Glaxo Lab Ltd | Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids |
| GB1438940A (en) * | 1972-07-19 | 1976-06-09 | Glaxo Lab Ltd | 17beta-haloalkoxycarbonyl-17alpha-oxysteroids |
-
1974
- 1974-08-30 GB GB38090/74A patent/GB1514476A/en not_active Expired
-
1975
- 1975-08-29 BE BE159583A patent/BE832889A/en not_active IP Right Cessation
- 1975-08-29 CH CH1120375A patent/CH612686A5/en not_active IP Right Cessation
- 1975-08-29 IE IE1904/75A patent/IE41663B1/en unknown
- 1975-08-29 DK DK389175AA patent/DK136074B/en not_active IP Right Cessation
- 1975-08-29 SE SE7509651A patent/SE405976B/en not_active IP Right Cessation
- 1975-08-29 NL NL7510226A patent/NL7510226A/en not_active Application Discontinuation
- 1975-08-29 FR FR7526651A patent/FR2282899A1/en active Granted
- 1975-08-29 JP JP50104825A patent/JPS5148649A/ja active Pending
- 1975-08-29 DE DE19752538595 patent/DE2538595A1/en not_active Ceased
- 1975-08-29 ZA ZA00755553A patent/ZA755553B/en unknown
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003072592A1 (en) * | 2002-01-15 | 2003-09-04 | Glaxo Group Limited | 17.alpha-cycloalkyl/cycloylkenyl esters of alkyl-or haloalkyl-androst-4-en-3-on-11.beta.,17.alpha.-diol 17.beta.-carboxylates as anti-inflammatory agents |
| WO2003062259A3 (en) * | 2002-01-21 | 2003-08-28 | Glaxo Group Ltd | Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents |
| WO2003082896A3 (en) * | 2002-03-29 | 2003-11-20 | Farmabios Srl | A PROCESS FOR THE PREPARATION OF 6α-FLUORO STEROIDS BY ISOMERISATION OF 6β-FLUOROSTEROIDS |
| JP2009513533A (en) * | 2003-07-11 | 2009-04-02 | グラクソ グループ リミテッド | Certain glucocorticosteroid compounds with anti-inflammatory activity |
| US7524970B2 (en) | 2003-07-11 | 2009-04-28 | Glaxo Group Limited | Compounds |
| US7288536B2 (en) | 2003-07-11 | 2007-10-30 | Glaxo Group Limited | Specific glucocorticosteroid compound having anti-inflammatory activity |
| US7291609B2 (en) | 2003-07-11 | 2007-11-06 | Glaxo Group Limited | Specific glucocorticosteroid compound having anti-inflammatory activity |
| RU2348645C2 (en) * | 2003-07-11 | 2009-03-10 | Глаксо Груп Лимитед | Specific glycocotricosteroid compound with antiinflammatory effect |
| WO2005005451A1 (en) | 2003-07-11 | 2005-01-20 | Glaxo Group Limited | Specific glucocorticosteroid compound having anti- inflammatory activity |
| JP2009514781A (en) * | 2003-07-11 | 2009-04-09 | グラクソ グループ リミテッド | Certain glucocorticosteroid compounds with anti-inflammatory activity |
| WO2005005452A1 (en) | 2003-07-11 | 2005-01-20 | Glaxo Group Limited | Specific glucocorticosteroid compound having anti- inflammatory activity |
| RU2359973C2 (en) * | 2003-07-11 | 2009-06-27 | Глаксо Груп Лимитед | Specific glycocorticosteroid compound with antiinflammatory effect |
| AU2004255855B2 (en) * | 2003-07-11 | 2009-07-30 | Glaxo Group Limited | Specific glucocorticosteroid compound having anti- inflammatory activity |
| KR101075324B1 (en) | 2003-07-11 | 2011-10-19 | 글락소 그룹 리미티드 | Specific glucocorticosteroid compound having anti-inflammatory activity |
| AU2004255854B2 (en) * | 2003-07-11 | 2009-10-22 | Glaxo Group Limited | Specific glucocorticosteroid compound having anti- inflammatory activity |
| US7638508B2 (en) | 2003-07-11 | 2009-12-29 | Glaxo Group Limited | Glucocorticosteroid compound having anti-inflammatory activity |
| KR101029207B1 (en) | 2003-07-11 | 2011-04-12 | 글락소 그룹 리미티드 | Certain glucocorticosteroid compounds with anti-inflammatory activity |
| US7579335B2 (en) | 2005-01-10 | 2009-08-25 | Glaxo Group Limited | Androstane 17α-carbonate derivatives for use in the treatment of allergic and inflammatory conditions |
Also Published As
| Publication number | Publication date |
|---|---|
| IE41663L (en) | 1976-02-29 |
| DK136074B (en) | 1977-08-08 |
| SE7509651L (en) | 1976-03-01 |
| DK389175A (en) | 1976-03-01 |
| ZA755553B (en) | 1976-09-29 |
| JPS5148649A (en) | 1976-04-26 |
| DK136074C (en) | 1978-01-16 |
| FR2282899A1 (en) | 1976-03-26 |
| BE832889A (en) | 1976-03-01 |
| SE405976B (en) | 1979-01-15 |
| AU8440475A (en) | 1977-03-03 |
| DE2538595A1 (en) | 1976-03-11 |
| NL7510226A (en) | 1976-03-02 |
| IE41663B1 (en) | 1980-02-27 |
| FR2282899B1 (en) | 1978-11-10 |
| CH612686A5 (en) | 1979-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |