JPH01100156A - 6-methoxymethoxy-3,5-cyclovitamin d3 derivative - Google Patents
6-methoxymethoxy-3,5-cyclovitamin d3 derivativeInfo
- Publication number
- JPH01100156A JPH01100156A JP25772587A JP25772587A JPH01100156A JP H01100156 A JPH01100156 A JP H01100156A JP 25772587 A JP25772587 A JP 25772587A JP 25772587 A JP25772587 A JP 25772587A JP H01100156 A JPH01100156 A JP H01100156A
- Authority
- JP
- Japan
- Prior art keywords
- cyclovitamin
- compound
- methoxymethoxy
- hydroxy
- 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.)
- Pending
Links
- 239000000126 substance Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 abstract description 3
- 229940061627 chloromethyl methyl ether Drugs 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 2
- JAMFGQBENKSWOF-UHFFFAOYSA-N bromo(methoxy)methane Chemical compound COCBr JAMFGQBENKSWOF-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 229930003231 vitamin Natural products 0.000 abstract description 2
- 229940088594 vitamin Drugs 0.000 abstract description 2
- 235000013343 vitamin Nutrition 0.000 abstract description 2
- 239000011782 vitamin Substances 0.000 abstract description 2
- 150000003722 vitamin derivatives Chemical class 0.000 abstract description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229930003316 Vitamin D Natural products 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005805 hydroxylation reaction Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 235000019166 vitamin D Nutrition 0.000 description 2
- 239000011710 vitamin D Substances 0.000 description 2
- 150000003710 vitamin D derivatives Chemical class 0.000 description 2
- 229940046008 vitamin d Drugs 0.000 description 2
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003431 steroids Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- -1 vitamin D3 tosylate compound Chemical class 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
この発明は、ビタミンＤ様活性を持つ１α−ヒドロキシ
ル化合物を合成するのに適した中間体化合物を提供する
ものである。従って本発明は、医療用薬物の製造に利用
されるものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention provides intermediate compounds suitable for synthesizing 1α-hydroxyl compounds with vitamin D-like activity. Therefore, the present invention is utilized in the production of medical drugs.
（従来の技術） ビタミンＤ活性を持つ化合物に変換するには。(Conventional technology) To convert it into a compound with vitamin D activity.
ｌα−ヒドロキシル化を行わなければならない。lα-hydroxylation must be carried out.
この１１−ヒドロキシル化を化学的に行うことが、多く
検討されている０例えば、ステロイド骨格の１位を選択
的にヒドロキシル化し、光化学的に開環１次いで異性化
、加水分解してｌα−ヒドロキシビタミンＤ、を得る方
法が知られている（特公昭５６ ５４３１５号）、又、
ビタミンＤ３トシレート化合物をソルボリシスし、得ら
れた６−アルコキシ−３，５−シクロビタミンＤ２をア
リル酸化し、ソルボリシスを経て１α−ヒドロキシビタ
ミンＤ３を得る方法もある（特公昭５８−２８８７６号
）。Many studies have been conducted to chemically perform this 11-hydroxylation. For example, selectively hydroxylating the 1-position of the steroid skeleton, photochemically ring-opening, isomerizing, and hydrolyzing lα-hydroxy A method for obtaining vitamin D is known (Special Publication No. 54315 of 1983), and
There is also a method of solvolysing a vitamin D3 tosylate compound, allylicizing the obtained 6-alkoxy-3,5-cyclovitamin D2, and obtaining 1α-hydroxyvitamin D3 through solvolysis (Japanese Patent Publication No. 58-28876).
（発明が解決しようとする問題点）
本発明は、１α−ヒドロキシビタミンＤ１を造るうえで
有効、且つ新規な中間化合物を提供するものである。ｖ
Ｉ！供される化合物は次の式で示され（式中Ａは水素原
子又はＯＨを示す）
（問題点を解決するための手段）
本発明によって提供される前記式で示される化合物は、
例えば次のようにして造られる。即ち、公知の方法によ
り造った６Ｒ（又は６Ｓ）−ヒドロキシ−３，５−シク
ロビタミンＤ、を原料として、適宜溶媒（例えば、−テ
トラヒドロフラン、ジオキサン、ヘキサン、ベンゼン、
トルエン、など）中、ハロゲノメチルメチルエーテル（
例えば、クロロメチルメチルエーテル、ブロモメチルメ
チルエーテルなど）を反応させる０反応は三級アミン（
例えば、トリ、エチルアミン、ジイソプロピルエチルア
ミンなど）の存在で加温して行うと良い。(Problems to be Solved by the Invention) The present invention provides a novel intermediate compound that is effective in producing 1α-hydroxyvitamin D1. v
I! The provided compound is represented by the following formula (in the formula, A represents a hydrogen atom or OH) (Means for solving the problem) The compound represented by the above formula provided by the present invention is:
For example, it is created as follows. That is, using 6R (or 6S)-hydroxy-3,5-cyclovitamin D prepared by a known method as a raw material, an appropriate solvent (for example, -tetrahydrofuran, dioxane, hexane, benzene,
halogenomethyl methyl ether (toluene, etc.)
For example, 0 reaction in which chloromethyl methyl ether, bromomethyl methyl ether, etc.) is reacted with a tertiary amine (
For example, heating may be carried out in the presence of trichloride, ethylamine, diisopropylethylamine, etc.).
かくて得られる６Ｒ（又は６Ｓ）−メトキシメトキシ−
３，５−シクロビタミンＤ３は、適宜溶媒（例えば、塩
化メチレン、ジクロルエタンなど）中、二酸化セレン、
し−ブチル−ヒドロペルオキシドなどを使って酸化し、
１α−ヒドロキシ−６Ｒ（又は６Ｓ）−メトキシメトキ
シ−３，５−シクロビタミンＤ３（式中ＡがＯＨの化合
物）を得る。The thus obtained 6R (or 6S)-methoxymethoxy-
3,5-cyclovitamin D3 can be prepared by adding selenium dioxide, selenium dioxide,
Oxidize using butyl hydroperoxide, etc.
1α-hydroxy-6R (or 6S)-methoxymethoxy-3,5-cyclovitamin D3 (a compound in which A is OH) is obtained.
かくて得られた化合物は有機酸（例えば、酢酸、ｐ−ト
ルエンスルホン酸など）を使ってソルボリシスして、１
α−ヒドロキシビタミンＤ、に導かれる。かへるソルボ
リシスにおいて１本発明中間体は、立体異性体の選択性
に影響があるように見受けられる。The thus obtained compound is solvolyzed using an organic acid (e.g. acetic acid, p-toluenesulfonic acid, etc.) to give 1
Derived from α-hydroxyvitamin D. In the solvolysis process, one intermediate of the present invention appears to have an effect on stereoisomer selectivity.
以下実施例を記述して本発明を詳述する。The present invention will be explained in detail by describing examples below.
実施例１
６Ｒ−メトキシメトキシ−３，５−シクロビタミンＤ３
の合成：
６Ｒ−ヒドロキシ−３，５−シクロビタミンＤ３０．３
２ｇにテトラヒドロフラン１０ｍ１、ジイソプロピルエ
チルアミン１．１８ｇ、クロロメチルメチルエーテル０
．６７ｇを加え、４０℃で一夜反応させた０反応液を濃
縮し、ヘキサン３０ｍ１．水１０ｍ１を加えて有機層を
分離した。これを冷希塩酸、水、重曹水、水、飽和食塩
水で順次洗浄し、硫酸マグネシウムで乾燥させた。溶媒
を留去して得たシロップ状物質０．３６ｇをカラムクロ
マトグラフィにて精製し〔シリカゲル１８ｇ、溶離液：
ヘキサン／ジイソプロピルエーテル（５０／１））、針
状晶の６Ｒ−メトキシメトキシ−３，５−シクロビタミ
ンＤ３０．３０ｇを得た。Example 1 6R-methoxymethoxy-3,5-cyclovitamin D3
Synthesis of: 6R-hydroxy-3,5-cyclovitamin D30.3
2g, 10ml of tetrahydrofuran, 1.18g of diisopropylethylamine, 0 chloromethyl methyl ether
．． 67g was added and reacted overnight at 40°C.The reaction solution was concentrated and diluted with 30ml of hexane. 10 ml of water was added and the organic layer was separated. This was washed successively with cold dilute hydrochloric acid, water, aqueous sodium bicarbonate, water, and saturated brine, and dried over magnesium sulfate. 0.36 g of a syrupy substance obtained by distilling off the solvent was purified by column chromatography [18 g of silica gel, eluent:
Hexane/diisopropyl ether (50/1)), 30.30 g of 6R-methoxymethoxy-3,5-cyclovitamin D in the form of needle-like crystals was obtained.
（収率８４％）
融点 ６６．５〜６８．０℃
Ｃα〕”＋１０．６°（Ｃ＝１．６３、ＣＨＣｌ、）Ｎ
ＭＲスペクトル（ＣＤＣＩ、） δ （ｐｐｍ）：０．
５３ （３Ｈ，ｓ、１８−Ｈ，）
０．７８ （ＬＨ，ｍ、３−Ｈ）
０．８７ （６Ｈ，ｄ、Ｊ＝６．５Ｈｚ、２６−Ｈ，お
よび２７−Ｈ３）
０．９２ （３Ｈ，ｄ、Ｊ＝６．０Ｈｚ、２１−Ｈ８）
３．３６ （３Ｈ，ｓ、−０−ＣＨ，）４．５１〜４．
６３ （３Ｈ，ｍ、６−Ｈおよび一〇−ＣＨ２−０−）
４．８９ （ＩＨ，ｍ （シャープ）、１９（Ｚ又はＥ
）−Ｈ）
５、０６〜５．１１ （２Ｉ１． ｍ、７−Ｈおよび１
９（Ｚ又はＥ）−Ｈ）
実施例２
（Ｉｓ、６Ｒ）−１−ヒドロキシ−６−メドキシメトキ
シー３，５−シクロビタミンＤ３の合成二二酸化セレン
０．２２ｇ、ｔ−ブチルヒドロパーオキシド０．７１ｇ
、塩化メチレン６０ｍ１を室温下で３０分間撹拌し、そ
の中に６Ｒ−メトキシメトキシ−３，５−シクロビタミ
ンＤ、１．７０ｇの塩化メチレン２０ｍ１溶液を加え、
更に３０分間撹拌した。反応液を１０％水酸化カリウム
水溶液でクエンチし、水、飽和食塩水で順次洗浄し、硫
酸マグネシウムで乾燥した後、濃縮した。得られたシロ
ップ状物ｆｉ２．０１ｇをカラムクロマトグラフィにて
精製し〔シリカゲル４０．２ｇ、溶離液：ヘキサン／酢
酸エチル（２０／３））、（ＩＳ、６Ｒ） −１−ヒド
ロキシ−６−メドキシメトキシー３，５−シクロビタミ
ンＤ、０．９３ｇを得た。（収率５３％）
マススペクトル（ｍ／Ｚ）：
４４４ 、 ３ ５９ ６ （Ｍ十） （Ｃ
ｚｓＩＬｓＯ：＋としての理論値４４４．３６０３）
ＩＲスペクトル（フィルム）：
ＬｌｏＨ３４３０ａｎ
ＮＭＲスペクトル（ＣＤＣＩ、） δ （ｐｐｍ）：
０ 、５３ （３Ｈ，ｓ 、 １８−ＩＬ）０．６
５ （ＬＨ，ｍ、３−Ｈ）
０．８７ （６Ｈ，ｄ、Ｊ＝６．６Ｈｚ、２６−Ｉ−
１，および２７−１１．）
０．９２ （３Ｈ，ｄ、Ｊ＝６．３Ｈｚ、２ｌ−Ｉ−Ｉ
、）
３．３５ （３Ｈ，ｓ、−０−ＣＨ，）４．２１（ＩＨ
ｌｍ、１−Ｈ）
４．５３〜４．６３ （３Ｈ，ｍ、６−Ｈおよび一〇−
ＣＨ，−０−）
５．０１ （ＬＨ，ｄ、Ｊ＝９．６Ｈｚ。(Yield 84%) Melting point 66.5-68.0°C Cα〕”+10.6° (C=1.63, CHCl,)N
MR spectrum (CDCI,) δ (ppm): 0.
53 (3H, s, 18-H,) 0.78 (LH, m, 3-H) 0.87 (6H, d, J=6.5Hz, 26-H, and 27-H3) 0.92 ( 3H, d, J=6.0Hz, 21-H8) 3.36 (3H, s, -0-CH,) 4.51-4.
63 (3H, m, 6-H and 10-CH2-0-) 4.89 (IH, m (Sharp), 19 (Z or E
)-H) 5, 06-5.11 (2I1. m, 7-H and 1
9(Z or E)-H) Example 2 Synthesis of (Is, 6R)-1-hydroxy-6-medoxymethoxy-3,5-cyclovitamin D3 0.22 g of selenium dioxide, t-butyl hydroperoxide 0.71g
, 60 ml of methylene chloride was stirred at room temperature for 30 minutes, and a solution of 1.70 g of 6R-methoxymethoxy-3,5-cyclovitamin D in 20 ml of methylene chloride was added thereto.
Stirred for an additional 30 minutes. The reaction solution was quenched with a 10% aqueous potassium hydroxide solution, washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated. 2.01 g of the obtained syrupy substance fi was purified by column chromatography [40.2 g of silica gel, eluent: hexane/ethyl acetate (20/3)], (IS, 6R) -1-hydroxy-6-medoxy 0.93 g of methoxy-3,5-cyclovitamin D was obtained. (Yield 53%) Mass spectrum (m/Z): 444, 3596 (M0) (C
zsILsO: +Theoretical value 444.3603) IR spectrum (film): LloH3430an NMR spectrum (CDCI,) δ (ppm):
0, 53 (3H,s, 18-IL) 0.6
5 (LH, m, 3-H) 0.87 (6H, d, J=6.6Hz, 26-I-
1, and 27-11. ) 0.92 (3H, d, J=6.3Hz, 2l-I-I
, ) 3.35 (3H,s, -0-CH,) 4.21 (IH
lm, 1-H) 4.53-4.63 (3H, m, 6-H and 10-
CH, -0-) 5.01 (LH, d, J = 9.6Hz.
７−Ｈ）
５．１７ （ＬＨ，ｍ （シャープ）、１９（Ｚ）−Ｈ
又は１９ （Ｅ）−Ｈ）
５．２９ （ＬＨ，ｍ （シャープ）、１９ （Ｚ）
−Ｉ−Ｉ又は１９ （Ｅ）−Ｈ）7-H) 5.17 (LH,m (Sharp), 19(Z)-H
or 19 (E)-H) 5.29 (LH, m (sharp), 19 (Z)
-I-I or 19 (E)-H)
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25772587A JPH01100156A (en) | 1987-10-13 | 1987-10-13 | 6-methoxymethoxy-3,5-cyclovitamin d3 derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25772587A JPH01100156A (en) | 1987-10-13 | 1987-10-13 | 6-methoxymethoxy-3,5-cyclovitamin d3 derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01100156A true JPH01100156A (en) | 1989-04-18 |
Family
ID=17310229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25772587A Pending JPH01100156A (en) | 1987-10-13 | 1987-10-13 | 6-methoxymethoxy-3,5-cyclovitamin d3 derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01100156A (en) |
-
1987
- 1987-10-13 JP JP25772587A patent/JPH01100156A/en active Pending
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