EP0000471A1 - Neue Kortikoide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate - Google Patents
Neue Kortikoide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate Download PDFInfo
- Publication number
- EP0000471A1 EP0000471A1 EP78100135A EP78100135A EP0000471A1 EP 0000471 A1 EP0000471 A1 EP 0000471A1 EP 78100135 A EP78100135 A EP 78100135A EP 78100135 A EP78100135 A EP 78100135A EP 0000471 A1 EP0000471 A1 EP 0000471A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- corticoids
- general formula
- dihydroxy
- oxo
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 11
- -1 methylenedioxy groups Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 206010012455 Dermatitis exfoliative Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241001303601 Rosacea Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 201000011486 lichen planus Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
- C07J71/0047—Nitrogen only at position 2(3)
Definitions
- the invention relates to new corticoids, a process for their preparation and pharmaceutical preparations which contain these corticoids as an active ingredient.
- New corticoids processes for their preparation and pharmaceutical preparations containing them.
- alkanoyloxy group Y should preferably be understood to mean a group which is derived from a saturated aliphatic monocarboxylic acid containing 1 to 8 carbon atoms.
- alkanoyloxy groups include:
- the acetoxy group, the propionyloxy group, the butyryloxy group, the pentanoyloxy group and the hexanoyioxy group are acetoxy groups, the propionyloxy group, the butyryloxy group, the pentanoyloxy group and the hexanoyioxy group.
- An alkoxy group Y is preferably understood to mean an alkoxy group containing 1 to 6 carbon atoms, such as, for example, the methoxy group, ethoxy group, propyloxy group or butyloxy group.
- the process according to the invention for the preparation of the new corticosteroid is characterized in that the methylenedioxy groups of a compound of the general formula II hydrolytically cleaves,
- the 21-hydroxy group esterified or to the aldehyde group is oxidized and the aldehyde obtained is oxidized in the presence of an alcohol with atmospheric oxygen or manganese (IV) oxide.
- the cleavage of the methylenedioxy groups and the acylation of the 21-hydroxysteroid formed can be carried out, for example, under the conditions described in German Patent 1,072,622.
- the reaction conditions are suitable, as described in German Offenlegungsschrift 24 41-284.
- the new corticoids of the general formula I are pharmacologically active substances which are distinguished in particular by the fact that, when applied topically, they have a pronounced anti-inflammatory activity, while they are systemically poorly effective or ineffective.
- these compounds are often distinguished by a rapid onset of action, a high intensity and a long duration of action, they are inexpensive to absorb and, in galenical formulations, have relatively good stability.
- the new compounds are suitable in combination with the excipients common in Galician pharmacy for the local treatment of contact dermatitis, various types of eczema, neurodermatoses, erythroderma, burns, pruritis vulvae et ani, rosacea erythematosus cutaneus, psoriasis, lichen planus et verrucosus and the like Skin diseases
- the pharmaceutical specialties are produced in the usual way. Way, by converting the active ingredients with suitable additives in the desired application form, such as: solutions, lotions, ointments, creams or plasters.
- suitable additives such as: solutions, lotions, ointments, creams or plasters.
- the active substance concentration depends on the form of administration.
- an active ingredient concentration of 0.01% to 1% is preferably avoided.
- the new compounds if appropriate in combination with the customary carriers and auxiliaries, are also well suited for the production of inhalants.
- the residue consists of 1.8 g of 2 '- (4-fluoro-phenyl) -11ß, 17 ⁇ -dihydroxy-20-oxo-2H'-2,4-pregnadieno [3,2-c] pyrazol-21-al.
- Ma receives 251 mg of 2 '- (4-fluoro-phenyl) -11ß, 17 ⁇ -dihydroxy-20-oxo-2H'-2,4-pregnadieno [3,2-c] pyrazole-21-acidic acid methyl ester. Melting point 192 ° C (recrystallized from acetone-hexane).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772727367 DE2727367A1 (de) | 1977-06-14 | 1977-06-14 | Neue kortikoide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0000471A1 true EP0000471A1 (de) | 1979-02-07 |
Family
ID=6011715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100135A Withdrawn EP0000471A1 (de) | 1977-06-14 | 1978-06-12 | Neue Kortikoide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0000471A1 (enrdf_load_stackoverflow) |
| DE (1) | DE2727367A1 (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005528385A (ja) * | 2002-04-11 | 2005-09-22 | メルク エンド カムパニー インコーポレーテッド | 選択的糖質コルチコイド受容体モジュレーターとしての１Ｈ−ベンゾ［ｆ］インダゾール−５−イル誘導体 |
| WO2009044200A1 (en) * | 2007-10-04 | 2009-04-09 | Astrazeneca Ab | Steroidal [3, 2-c] pyrazole compounds, with glucocorticoid activity |
| US7625920B2 (en) | 2003-03-07 | 2009-12-01 | Merck & Co., Inc. | Fluorinated 4-azasteroid derivatives as androgen receptor modulators |
| WO2010147947A3 (en) * | 2009-06-16 | 2011-03-03 | Schering Corporation | NOVEL [3,2-c] HETEROARYL STEROIDS AS GLUCOCORTICOID RECEPTOR AGONISTS, COMPOSITIONS AND USES THEREOF |
| CN102459306A (zh) * | 2009-04-03 | 2012-05-16 | 阿斯利康(瑞典)有限公司 | 具有糖皮质激素活性的甾族[3，2-c]吡唑化合物的新酰胺衍生物 |
| US8338587B2 (en) | 2009-04-03 | 2012-12-25 | Astrazeneca Ab | Compounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1418994A1 (de) * | 1960-11-23 | 1969-04-24 | Merck & Co Inc | 17 alpha,21-Dihydroxy-20-oxo-4-pregnen[3,2-c]pyrazol-Verbindungen und ihre 21-Ester und ein Verfahren zu ihrer Herstellung |
| US3704295A (en) * | 1959-02-16 | 1972-11-28 | Sterling Drug Inc | Steroido(3,2-c)pyrazoles and preparation thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299054A (en) * | 1961-12-01 | 1967-01-17 | Merck & Co Inc | 4-pregneno-[3, 2-c] pyrazoles and processes of preparing them |
-
1977
- 1977-06-14 DE DE19772727367 patent/DE2727367A1/de active Granted
-
1978
- 1978-06-12 EP EP78100135A patent/EP0000471A1/de not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3704295A (en) * | 1959-02-16 | 1972-11-28 | Sterling Drug Inc | Steroido(3,2-c)pyrazoles and preparation thereof |
| DE1418994A1 (de) * | 1960-11-23 | 1969-04-24 | Merck & Co Inc | 17 alpha,21-Dihydroxy-20-oxo-4-pregnen[3,2-c]pyrazol-Verbindungen und ihre 21-Ester und ein Verfahren zu ihrer Herstellung |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 67 (1967) 107174v & J. Pharm. Pharmacol 19(9) 590-5, (1967) & CHEMICAL ABSTRACTS, 8th Collective Index Formulas S10035 f. * |
| JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Band 86 (1964) Seite 1520 bis 1527. * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1496892A4 (en) * | 2002-04-11 | 2006-01-25 | Merck & Co Inc | 1H-BENZO (F) INDAZOL-5-YL DERIVATIVES AS SELECTIVE GLUCOCORTICOID RECEPTOR MODULATORS |
| US7282591B2 (en) | 2002-04-11 | 2007-10-16 | Merck & Co., Inc. | 1h-benzo{f}indazol-5-yl derivatives as selective glucocorticoid receptor modulators |
| JP2005528385A (ja) * | 2002-04-11 | 2005-09-22 | メルク エンド カムパニー インコーポレーテッド | 選択的糖質コルチコイド受容体モジュレーターとしての１Ｈ−ベンゾ［ｆ］インダゾール−５−イル誘導体 |
| US7625937B2 (en) | 2002-04-11 | 2009-12-01 | Merck & Co., Inc. | 1H-benzo[F]indazol-5-YL derivatives as selective glucocorticoid receptor modulators |
| US7625920B2 (en) | 2003-03-07 | 2009-12-01 | Merck & Co., Inc. | Fluorinated 4-azasteroid derivatives as androgen receptor modulators |
| JP2010540612A (ja) * | 2007-10-04 | 2010-12-24 | アストラゼネカ・アクチエボラーグ | グルココルチコイド活性を有するステロイド［３，２−ｃ］ピラゾール化合物 |
| WO2009044200A1 (en) * | 2007-10-04 | 2009-04-09 | Astrazeneca Ab | Steroidal [3, 2-c] pyrazole compounds, with glucocorticoid activity |
| AU2008306593B2 (en) * | 2007-10-04 | 2012-04-12 | Astrazeneca Ab | Steroidal [3, 2-C] pyrazole compounds, with glucocorticoid activity |
| US8163724B2 (en) | 2007-10-04 | 2012-04-24 | Astrazeneca Ab | Glucocorticosteroids, processes for their preparation, pharmaceutical compositions containing them and their use in therapy |
| AU2008306593C1 (en) * | 2007-10-04 | 2012-10-04 | Astrazeneca Ab | Steroidal [3, 2-C] pyrazole compounds, with glucocorticoid activity |
| CN102459306A (zh) * | 2009-04-03 | 2012-05-16 | 阿斯利康(瑞典)有限公司 | 具有糖皮质激素活性的甾族[3，2-c]吡唑化合物的新酰胺衍生物 |
| US8338587B2 (en) | 2009-04-03 | 2012-12-25 | Astrazeneca Ab | Compounds |
| WO2010147947A3 (en) * | 2009-06-16 | 2011-03-03 | Schering Corporation | NOVEL [3,2-c] HETEROARYL STEROIDS AS GLUCOCORTICOID RECEPTOR AGONISTS, COMPOSITIONS AND USES THEREOF |
| CN102834406A (zh) * | 2009-06-16 | 2012-12-19 | 默沙东公司 | 作为糖皮质激素受体激动剂的新的[3.2-c]杂芳基甾体、其组合物和用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2727367C2 (enrdf_load_stackoverflow) | 1988-12-29 |
| DE2727367A1 (de) | 1979-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Designated state(s): BE CH DE FR GB LU NL |
|
| 17P | Request for examination filed | ||
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Withdrawal date: 19821028 |
|
| RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: WENDT, HANS, DR Inventor name: LAURENT, HENRY, DR. Inventor name: WIECHERT, RUDOLF, PROF. |