JPS5922720B2 - Steroidal 9,11β-dihalo-[16α,17b][1,4]dioxanes - Google Patents
Steroidal 9,11β-dihalo-[16α,17b][1,4]dioxanesInfo
- Publication number
- JPS5922720B2 JPS5922720B2 JP138476A JP138476A JPS5922720B2 JP S5922720 B2 JPS5922720 B2 JP S5922720B2 JP 138476 A JP138476 A JP 138476A JP 138476 A JP138476 A JP 138476A JP S5922720 B2 JPS5922720 B2 JP S5922720B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- compound
- steroidal
- dioxane
- formula
- 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
- 230000003637 steroidlike Effects 0.000 title description 4
- 150000002012 dioxanes Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000003431 steroids Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- -1 1 Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003862 glucocorticoid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940037128 systemic glucocorticoids Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 201000009053 Neurodermatitis Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Description
【発明の詳細な説明】
本発明はステロイド類、更に詳しくは抗炎症剤として有
用なる新規ステロイダル９、１１β−ジハロ〔１６α３
１７−ｂ〕〔１、４〕ジオキサン類に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides steroids, more specifically, a novel steroidal 9,11β-dihalo[16α3
17-b] [1,4] Regarding dioxanes.
本発明化合物は次の一般式で示すことができる：ＣＨ２
０−Ｃ−低級アルキル
Ｃ二Ｏ
Ｎ□工□、゛
Π
〔式中、Ｘはハロゲン（好ましくは塩素もしくはフツ素
）、１，２位および６，７位における点線は要すれば存
在することもある二重結合を表わす。The compound of the present invention can be represented by the following general formula: CH2
0-C-Lower alkyl C2O N□Work□,゛Π [In the formula, also represents a double bond.
〕。本発明はステロイド性目的化合物〔１〕を提供する
ことを目的とする。]. The object of the present invention is to provide a steroidal target compound [1].
本発明の新規化合物〔〕は式：で示される化合物とＮ−
クロロスクシンイミドおよび式： Ｈ−Ｘ〔式中
、Ｘは前記と同意義。The novel compound [ ] of the present invention is a compound represented by the formula: and N-
Chlorosuccinimide and the formula: H-X [wherein, X has the same meaning as above.
〕で示される酸を反応させることにより製造することが
できる。] It can be produced by reacting the acids shown below.
この反応操作は各試剤をたとえば水酢酸のごとき溶媒中
、０〜３０℃で１〜６時間処理することにより行うこと
ができる。本発明のステロイド目的化合物〔１〕はグル
ココルチコイドであつて、抗炎症性を有する生理学的活
性物質であるから、リウマチ性関節炎処置のため、よく
知られたグルココルチコイド類の代わりに用いることが
でき、この目的のために化合牧０〕をヒドロコーチゾン
と同様の方法（たとえばこの特定のステロイドの相対的
効果のために調節された投与方法）により投与すること
ができる。This reaction operation can be carried out by treating each reagent in a solvent such as hydroacetic acid at 0 to 30°C for 1 to 6 hours. Since the steroidal compound [1] of the present invention is a glucocorticoid and is a physiologically active substance with anti-inflammatory properties, it can be used in place of well-known glucocorticoids for the treatment of rheumatoid arthritis. , Compound 0] can be administered for this purpose in a manner similar to hydrocortisone (eg, with a dosing regimen adjusted for the relative efficacy of this particular steroid).
加うるに、本発明のステロイド化合物〔１〕は皮ふ炎、
乾癖、日焼け、神経皮ふ炎、湿疹、外部生殖器掻痒症の
ごとき皮ふ症状を処置するため、これを公知グルココル
チコイド類の代わりに局所的に使用することができる。
本発明目的化合物〔１〕は経口的に投与するとき、その
投与量を０．１〜２００η、好ましくは０．３〜１００
ｍｆ１とすることができる。In addition, the steroid compound [1] of the present invention can treat dermatitis,
It can be used topically in place of known glucocorticoids to treat skin conditions such as psoriasis, sunburn, neurodermatitis, eczema, and external genital pruritus.
When the compound [1] of the present invention is administered orally, the dosage is 0.1 to 200η, preferably 0.3 to 100η.
mf1.
局所的に投与するときは本発明目的化合物〔１〕を通常
のクリームもしくはローシヨン中、０．０１〜５．０７
０（重量）、好ましくは０．０５〜２．０７０（重量）
の投与量で用いることができる。本発明における出発物
質は次の方法により得ることができる。When administered locally, the compound [1] of the present invention is added to a conventional cream or lotion at a concentration of 0.01 to 5.07.
0 (weight), preferably 0.05 to 2.070 (weight)
It can be used at a dosage of The starting material in the present invention can be obtained by the following method.
すなわち、で示される１１β−ヒドロキシステロイド体
を脱水処理して、で示されるΔ９（１１）−ステロイド
出発物質を得る。That is, the 11β-hydroxysteroid body represented by is dehydrated to obtain the Δ9(11)-steroid starting material represented by.
この反応は常套の方法、たとえば（１）オキシ塩化リン
とピリジンによる脱水、（２）メタンスルホニルクロリ
ドとピリジンによる脱水などのごとき操作により進行せ
しめることができる。This reaction can be carried out by conventional methods such as (1) dehydration using phosphorus oxychloride and pyridine, (2) dehydration using methanesulfonyl chloride and pyridine, and the like.
本発明目的化合物〔１〕は次の方法により製することが
できる。The object compound [1] of the present invention can be produced by the following method.
すなわち、上記出発物質〔町とＮクロロスクシンイミド
および式： Ｈ−ＸＤ
〔式中、Ｘは前記と同意義。That is, the above starting material [Machi and N-chlorosuccinimide and the formula: H-XD [wherein, X has the same meaning as above].
〕で示される酸を反応させることによりステロイド性９
，１１β−ジハロ〔１６α，１７−ｂ〕〔１，４〕ジオ
キサン目的化合物〔１〕を得ることができる。] By reacting the acid shown in
, 11β-dihalo[16α,17-b][1,4]dioxane target compound [1] can be obtained.
なお、前記化合物〔旧は特開昭５０−１０１３５８号公
報（公開日：昭和５０年８月１１日）に開示されている
。Incidentally, the above compound [formerly disclosed in Japanese Patent Application Laid-open No. 101358/1983 (publication date: August 11, 1975).
次に実施例を挙げて本発明の具体的実施態様を説明する
。Next, specific embodiments of the present invention will be described with reference to Examples.
実施例 １
Ａ．２ｌ−ヒドロキシプレグナ一１，４，９（１１）−
トリエノ〔１６α，１７−ｂ〕〔１，４〕ジオキサン−
３，２０−ジオン・２１−アセテートの製造：１１β，
２１−ジヒドロキシプレグナ一１，４−ジエノ〔１６α
，１７−ｂ〕〔１，４〕ジオキサン−３，２０−ジオン
・２１−アセテート１，５９、ジメチルホルムアミド７
５ｍｅ１ピリジン３７．５Ｔｒ！！およびメタンスルホ
ニルクロリド１５ｒ！！ｌの混合物をＯ℃で７５分間攪
拌し、これを冷希塩酸に注ぎ、得られた混合物をクロロ
ホルムで抽出する。Example 1 A. 2l-Hydroxypregna-1,4,9(11)-
trieno[16α,17-b][1,4]dioxane-
Production of 3,20-dione 21-acetate: 11β,
21-dihydroxypregna-1,4-dieno[16α
, 17-b] [1,4] dioxane-3,20-dione 21-acetate 1,59, dimethylformamide 7
5me1 pyridine 37.5Tr! ! and methanesulfonyl chloride 15r! ! The mixture is stirred at 0° C. for 75 minutes, poured into cold dilute hydrochloric acid, and the resulting mixture is extracted with chloroform.
クロロホルム溶液を乾燥し、減圧下に濃縮する。残留物
をクロロホルムに溶解し、６０９−シリカゲルカラム上
、ヘキサンクロロホルム（１：１）を溶出液とするクロ
マトグラフイ一で精製し、２１−ヒドロキシプレグナ一
１，４，９（１１）一トリエノ〔１６ａ，１７−ｂ〕〔
１，４〕ジオキサン−３，２０−ジオン・２１−アセテ
ートを得た。Ｂ．９，ｌｌβ−ジクロロ−２１−ヒドロ
キシプレグナ一１，４−ジエノ〔１６ａ，１７−ｂ〕〔
１，４〕ジオキサン−３，２０−ジオン●２１−アセテ
ートの製造：２１−ヒドロキシプレグナ一１，４，９
（１１）一トリエノ〔１６α，１７−ｂ〕〔１，４〕ジ
オキサン−３，２０−ジオン・２１−アセテート１．２
９および塩化リチウム５．０９を氷酢酸５０ｍｌに溶解
し、この溶液を０〜５℃で撹拌しながらＮ−クロロスク
シンイミド４１３ｍｇを加える。Dry the chloroform solution and concentrate under reduced pressure. The residue was dissolved in chloroform and purified by chromatography on a 609-silica gel column using hexane chloroform (1:1) as the eluent. [16a, 17-b] [
1,4]dioxane-3,20-dione 21-acetate was obtained. B. 9,llβ-dichloro-21-hydroxypregna-1,4-dieno[16a,17-b]
1,4]Dioxane-3,20-dione●Production of 21-acetate: 21-hydroxypregna-1,4,9 (11)-trieno[16α,17-b][1,4]dioxane-3, 20-dione/21-acetate 1.2
9 and 5.09 g of lithium chloride are dissolved in 50 ml of glacial acetic acid, and 413 mg of N-chlorosuccinimide is added to this solution while stirring at 0-5°C.
乾燥塩化水素１２６ｍｇのテトラヒドロフラン２ｍｌ溶
液を加え、得られた混合物を室温で２時間撹拌した後、
冷水６００ｍｌに注ぎ、クロロホルムで抽出する。クロ
ロホルム溶液を水洗後、乾燥し、減圧下に蒸発させて粗
生成物１．３１ｇを得る。これを次に示すプレートクロ
マトグラフィーにより精製する。すなわち生成物を２０
×２０ｃｍ×２ｍｍのシリカゲルプレート（３枚）上、
クロロホルム−酢酸エチル（１：１）で２回展開し、中
間Ｒｆ値における紫外線に対する活性バンドを切除し、
これを酢酸エチルで溶出することにより、生成物７３５
ｍｇを得る。メタノールから再結晶して生成物５４０ｍ
ｇを得る。融点２５６〜２５８℃（分解）。これと母液
を再クロマトグラフィーに付して得られた生成物１３７
ｍｇとを合し、メタノールから再結晶して９、１１β−
ジクロロ−２１−ヒドロキシプレグナ−１，４−ジエノ
〔１６α、１７−ｂ〕〔１，４〕ジオキサン−３，２０
−ジオン・２１−アセテート５７５ｍｇを得た。融点２
５６〜２５８℃（分解）。元素分析、Ｃ２５Ｈ３０Ｃｌ
Ｏ６として、計算値：Ｃ，６０．３６％：Ｈ，６．０８
％：Ｃｌ，１４．２６％、実測値：Ｃ，６０．０９％：
Ｈ，５．８３％：Ｃｌ、１４．３％。After adding a solution of 126 mg of dry hydrogen chloride in 2 ml of tetrahydrofuran and stirring the resulting mixture at room temperature for 2 hours,
Pour into 600 ml of cold water and extract with chloroform. After washing the chloroform solution with water, it is dried and evaporated under reduced pressure to obtain 1.31 g of crude product. This is purified by plate chromatography as shown below. i.e. the product is 20
On x20cm x 2mm silica gel plates (3 pieces),
Developed twice with chloroform-ethyl acetate (1:1) to excise ultraviolet active bands at intermediate Rf values,
By eluting this with ethyl acetate, the product 735
Get mg. Recrystallized from methanol to give 540m of product.
get g. Melting point 256-258°C (decomposed). The product 137 obtained by rechromatography of this and the mother liquor
mg and recrystallized from methanol to obtain 9,11β-
Dichloro-21-hydroxypregna-1,4-dieno[16α,17-b][1,4]dioxane-3,20
575 mg of -dione 21-acetate was obtained. Melting point 2
56-258°C (decomposition). Elemental analysis, C25H30Cl
Calculated value as O6: C, 60.36%: H, 6.08
%: Cl, 14.26%, actual value: C, 60.09%:
H, 5.83%: Cl, 14.3%.
Claims (1)
る点線は要すれば存在することもある二重結合を表わす
。 〕。２ Ｘが塩素である特許請求の範囲第１項に記載の
ステロイド。 ３ Ｘがフッ素である特許請求の範囲第１項に記載のス
テロイド。 ４ 化合物名が９，１１β−ジクロロ−２１−ヒドロキ
シプレグナ−１，４−ジエノ〔１６α，１７−ｂ〕〔１
，４〕ジオキサン−３，２０−ジオン・２１−アセテー
トである特許請求の範囲第１項に記載のステロイド。[Claims] 1. A steroid represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼. [In the formula, X represents a halogen, and the dotted lines at the 1, 2 and 6, 7 positions represent double bonds that may be present if necessary. ]. 2. The steroid according to claim 1, wherein X is chlorine. 3. The steroid according to claim 1, wherein X is fluorine. 4 The compound name is 9,11β-dichloro-21-hydroxypregna-1,4-dieno[16α,17-b][1
, 4] dioxane-3,20-dione 21-acetate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/583,149 US3971773A (en) | 1974-11-08 | 1975-06-02 | Steroidal 9,11-dihalo-[16α,17-b]1,4-dioxanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51141881A JPS51141881A (en) | 1976-12-07 |
| JPS5922720B2 true JPS5922720B2 (en) | 1984-05-28 |
Family
ID=24331873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP138476A Expired JPS5922720B2 (en) | 1975-06-02 | 1976-01-01 | Steroidal 9,11β-dihalo-[16α,17b][1,4]dioxanes |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5922720B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5978219U (en) * | 1982-11-16 | 1984-05-26 | 株式会社ト−モク | composite packaging container |
-
1976
- 1976-01-01 JP JP138476A patent/JPS5922720B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5978219U (en) * | 1982-11-16 | 1984-05-26 | 株式会社ト−モク | composite packaging container |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51141881A (en) | 1976-12-07 |
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