JPH03169819A - Antithrombotic agent containing 1alpha-hydroxyvitamin d3 compounds - Google Patents
Antithrombotic agent containing 1alpha-hydroxyvitamin d3 compoundsInfo
- Publication number
- JPH03169819A JPH03169819A JP24470890A JP24470890A JPH03169819A JP H03169819 A JPH03169819 A JP H03169819A JP 24470890 A JP24470890 A JP 24470890A JP 24470890 A JP24470890 A JP 24470890A JP H03169819 A JPH03169819 A JP H03169819A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyvitamin
- 1alpha
- antithrombotic agent
- agent containing
- active ingredient
- 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
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical class 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 title claims abstract description 9
- 239000003146 anticoagulant agent Substances 0.000 title claims abstract description 7
- 229960004676 antithrombotic agent Drugs 0.000 title claims abstract description 7
- 239000000126 substance Substances 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 239000007900 aqueous suspension Substances 0.000 abstract description 2
- 239000007891 compressed tablet Substances 0.000 abstract description 2
- 235000019441 ethanol Nutrition 0.000 abstract description 2
- 239000007902 hard capsule Substances 0.000 abstract description 2
- 239000007905 soft elastic gelatin capsule Substances 0.000 abstract description 2
- 239000002511 suppository base Substances 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 abstract description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 2
- 244000299461 Theobroma cacao Species 0.000 abstract 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 abstract 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 abstract 1
- 235000014121 butter Nutrition 0.000 abstract 1
- 235000001046 cacaotero Nutrition 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 210000000664 rectum Anatomy 0.000 abstract 1
- 239000007901 soft capsule Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- BJYLYJCXYAMOFT-RRXOBRNQSA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-1-[(2r)-5-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCC(O)C(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C BJYLYJCXYAMOFT-RRXOBRNQSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010061728 Bone lesion Diseases 0.000 description 1
- 206010006002 Bone pain Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000013038 Hypocalcemia Diseases 0.000 description 1
- 208000000038 Hypoparathyroidism Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 208000003217 Tetany Diseases 0.000 description 1
- 229930003316 Vitamin D Natural products 0.000 description 1
- 201000006035 X-linked dominant hypophosphatemic rickets Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WFDKAKYREYOPOC-UHFFFAOYSA-N ethyl 4-hydroxybenzoate titanium Chemical compound [Ti].C(C)OC(=O)C1=CC=C(O)C=C1 WFDKAKYREYOPOC-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000705 hypocalcaemia Effects 0.000 description 1
- 208000011111 hypophosphatemic rickets Diseases 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 208000032349 type 2B vitamin D-dependent rickets Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 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)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明ハ、■α−ヒドロキシビタミンＤ３類を含有する
抗血栓症剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention (iii) relates to an antithrombotic agent containing α-hydroxyvitamin D3.
近年、デルカ（Ｄｅ Ｌｕｃａ ）等及びコデイツク（
Ｋｏｄｉｅｋ）等の一連の研究の結果、ビタミンＤ３の
生体内活性物質が１α，２５−ジヒドロキシビタミンＤ
（以下１α，２５− （ＯＨ） −Ｄ３と略３２
称する）であり、また１α位の水酸基の存在がその生物
活性の発現には必須であることが明らかにされた。以後
この活性型の１α． ２５−（ＯＨ）２−Ｄ３の類似体
、例えば１α−ヒドロキシビタミンＤ３（以下１α一（
ＯＨ）−Ｄ３と略称する）、１α，２４−ジヒドロキシ
ビタミンＤ３ （以下ｌα，２４一（ＯＨ）２−Ｄ３と
略称する）など多くの１αーヒドロキシビタミンＤ３類
が合成され、１α，２５− （ＯＨ） ２−Ｄ３ととも
にそのビタミンＤ様生物活性が注目されており、工α−
（ＯＨ）−Ｄ３は慢性腎不全、副甲状腺機能低下症，ビ
タミンＤ抵抗性クル病・骨軟化症におけるビタミンＤ代
謝異常を伴う諸症状（低カルシウム血症，テタニ骨痛，
骨病変等）の改善に適応されている。In recent years, De Luca et al. and Kodytsk (
As a result of a series of studies by Kodiek et al., the in vivo active substance of vitamin D3 was found to be 1α,25-dihydroxyvitamin D.
(hereinafter abbreviated as 1α,25-(OH)-D3), and the presence of a hydroxyl group at the 1α position is essential for the expression of its biological activity. From now on, this active form of 1α. Analogues of 25-(OH)2-D3, such as 1α-hydroxyvitamin D3 (hereinafter referred to as 1α-(
Many 1α-hydroxyvitamin D3s have been synthesized, including 1α,24-dihydroxyvitamin D3 (hereinafter abbreviated as lα,24-(OH)2-D3), and 1α,25-( OH) Along with 2-D3, its vitamin D-like biological activity has attracted attention, and
(OH)-D3 is associated with chronic renal failure, hypoparathyroidism, vitamin D-resistant rickets/osteomalacia, and various symptoms associated with abnormal vitamin D metabolism (hypocalcemia, tetani bone pain,
It is indicated for improving bone lesions, etc.).
本発明者等は、その後鋭意研究を続けた結果、１α−ヒ
ドロキシビタミンＤ３類に後述の抗血栓症作用のあるこ
とを見出し、本発明を完成した。As a result of continued intensive research, the present inventors discovered that 1α-hydroxyvitamin D3 has an antithrombotic effect as described below, and completed the present invention.
即ち本発明は、１α−ヒドロキシビタミンＤ３類の抗血
栓症剤に関する。That is, the present invention relates to antithrombotic agents of the 1α-hydroxyvitamin D3 class.
本発明において用いられるｌα−ヒドロキシビタミンＤ
３類とは
１α−（ＯＨ）−Ｄ３，
１α．２５− （ＯＨ） ２−Ｄ３，
１ α．２４３ （Ｏ｝Ｉ） ２ Ｄ３ ，ｌ α
，２４Ｒ （Ｏ Ｈ） ２Ｄ３ ，ｌａ， ２４３．
２５− （ＯＨ） ３−Ｄ３．１ α，２４Ｒ，２５
（Ｏ Ｈ） ３ Ｄ ３，１ ａ． ２５８．
２６ − （ＯＨ） ３−Ｄ３，１α．２ＳＲ．２６−
（Ｏ｝Ｉ） ３−Ｄ３．１ ａ．２５ （ＯＨ）
２ ２３ ０ＸＯ Ｄ３，１ α．２５ （Ｏ
Ｈ） ２ ２４−ＯＸＯ Ｄ３，Ｌ ａ． ２５Ｓ
． ２６ − （０．Ｈ）３−２３−ＯＸＯ−Ｄ３ ．
１ ａ， ２５Ｒ． ２Ｇ − （ＯＨ）３−２３−Ｏ
ＸＯ−Ｄ３ ．１ ａ， ２５Ｓ − （Ｏ Ｈ）２−
Ｄ３−２６． ２３Ｓ − ｈｃｔ＋＋ｎｅ ，１ ａ
． ２ＳＲ − （Ｏ Ｈ）２−Ｄ３−２６，２３Ｓ
− ｌｘｃｌｏｎｅ ，１ ａ − （ＯＨ） −２４
．２５．２６．２７ −ｊｅｌｒａｕｃｒ−２３−ＣＯ
ＯＨ−Ｃ３
などが含まれる。lα-hydroxyvitamin D used in the present invention
Type 3 is 1α-(OH)-D3, 1α. 25- (OH) 2-D3, 1 α. 243 (O}I) 2 D3 , l α
,24R(OH)2D3,la,243.
25- (OH) 3-D3.1 α,24R,25
(OH) 3 D 3,1 a. 258.
26-(OH)3-D3,1α. 2SR. 26-
(O}I) 3-D3.1 a. 25 (OH)
2 23 0XO D3,1 α. 25 (O
H) 2 24-OXO D3,L a. 25S
．． 26-(0.H)3-23-OXO-D3.
1 a, 25R. 2G-(OH)3-23-O
XO-D3. 1 a, 25S - (OH)2-
D3-26. 23S-hct++ne,1a
．． 2SR-(OH)2-D3-26,23S
- lxclone, 1 a - (OH) -24
．． 25.26.27 -jelraucr-23-CO
This includes OH-C3 and the like.
これらの本物質は例えばＵ．Ｓ，Ｐ！ｊｅｎｌ ３６９
７５５９ ．特開昭５１−７６２５２．特開昭５１−７
６２５４． Ｕ．Ｓ．Ｐａ＋ｅｎｌ３７４１９９６
，特開昭５５−２２６５５．特開昭５５−２２６５６，
特開昭５６−６１３５１． ＾ｒｅｈ．Ｂｉｏｃｈｅ
ａ＋．８ｉｏｐｂＢ．， ２０４，３８７（１９８１
）， Ｈ．Ｆ，Ｄｅ Ｌａｅｓ， ビタミンＤ−［
その新シイ流れ］，講談社，サイエンティフィク（１９
８２）などに開示されている。These substances include, for example, U. S,P! jenl 369
7559. Japanese Patent Publication No. 51-76252. Japanese Patent Publication No. 51-7
6254. U. S. Pa+enl3741996
, Japanese Patent Publication No. 55-22655. Japanese Patent Publication No. 55-22656,
Japanese Patent Publication No. 56-61351. ^reh. Bioche
a+. 8iopbB. , 204, 387 (1981
), H. F, De Laes, Vitamin D-[
The new flow], Kodansha, Scientific (19
82) and others.
本発明においては光学異性体のいずれを用いてもよく、
又、二種以上を混合して用いてもよい。In the present invention, any of the optical isomers may be used,
Also, two or more types may be used in combination.
本発明の抗血栓症剤は活性成分として上記本物質を含有
して、下記に示す種々の製剤形態にて用いられる。本発
明の抗血栓症剤は、経口的、非経口的に投与される。The antithrombotic agent of the present invention contains the above substance as an active ingredient and is used in various formulations shown below. The antithrombotic agent of the present invention is administered orally or parenterally.
投与形態としては例えば、圧縮錠剤、被覆錠剤，硬又は
軟弾性ゼラチンカプセル，エチルアルコール溶液，油性
または水性溶液または懸濁液などが用いられる。Examples of dosage forms that can be used include compressed tablets, coated tablets, hard or soft elastic gelatin capsules, ethyl alcohol solutions, oily or aqueous solutions or suspensions.
油性溶液の溶媒としては、植物油例えばヤシ油，トウモ
ロコシ油，綿実油，ココナッツ油，落花生油，魚肝油，
油状エステル例えばポリソルベート８０などを使用する
ことができる。As solvents for oily solutions, vegetable oils such as coconut oil, corn oil, cottonseed oil, coconut oil, peanut oil, fish liver oil,
Oily esters such as polysorbate 80 can be used.
直腸内投与の場合には坐剤ベース例えばカカオ脂または
そのトリグリセライドなどを含む薬用組威物とすること
ができる。For rectal administration, it may be a suppository base, such as a medicinal composition containing cocoa butter or its triglycerides.
本物質は単位投与形態中、２Ｘ １Ｇ’乃至ＩＸ １０
％、好ましくは２ＸＩＧ’乃至１％を含有する。The substance may be administered in unit dosage form from 2X 1G' to IX 10
%, preferably 2XIG' to 1%.
又、投与量は０．１乃至１Ｇ’ ｉｌｌｌ日／人、好ま
しくは ０．５乃至１０３ｎｌ日，／人とすることがで
きる。Further, the dosage can be 0.1 to 1 G'illl day/person, preferably 0.5 to 103 nl day/person.
そして、上記量的関係が保持されるように、１１〜３回
の投与回数となるように調製される。Then, in order to maintain the above quantitative relationship, the number of administrations is 11 to 3 times.
以下、実施例により本発明を詳述する。Hereinafter, the present invention will be explained in detail with reference to Examples.
実施例１
抗血栓作用
日
１０週齢ウイススタ一系雄ラットに１α−ヒドロキシビ
タミンＤ３類を各々 １００Ｉ４／ｋｇ、又溶媒（ＭＣ
Ｔ）を強制経口投与した。投与後６時間目にＡＤＰを静
注した。溶媒投与群のラットは全数死亡したが、１α−
ヒドロキシビタミンＤ３投与群のラットの死亡率は、
１α−（ＯＨ）−Ｄ３・・・・・・・・・５２％，１α
，２４Ｒ− （ＯＨ） ２−Ｄ３・・・・・・５ｌ％，
１α，２５− （ＯＨ） −Ｄ３・・・・・・・・
・５６％２
であった。Example 1 Antithrombotic Effect Day 10-week-old Wista strain male rats were given 1α-hydroxyvitamin D3 at 100I4/kg each, and a solvent (MC).
T) was orally administered by force. ADP was administered intravenously 6 hours after administration. All rats in the vehicle administration group died, but 1α-
The mortality rate of rats in the hydroxyvitamin D3 administration group was 1α-(OH)-D3...52%, 1α
,24R-(OH)2-D3...5l%,
1α,25- (OH) -D3・・・・・・・・・
・56%2
実施例２
１α−（ＯＨ）−Ｄ３をパナセート ８００（日本油脂
製，中級脂肪酸のトリグリセライド）に１０７４ ／
ｍｌの濃度に溶解し、１カプセル中に１α−（ＯＨ）−
Ｄ３を１埒含有するように下記剤皮成分を加温溶解し、
軟カプセル製造機を用いて常法により軟カプセル剤を作
成した。Example 2 1α-(OH)-D3 was added to Panacet 800 (manufactured by NOF Corporation, intermediate fatty acid triglyceride) at 1074/1α-(OH)-D3.
1α-(OH)- in one capsule.
The following skin components were heated and dissolved to contain 1 gram of D3,
Soft capsules were prepared in a conventional manner using a soft capsule making machine.
剤皮処方例
ゼラチン
グリセリン
防腐剤（エチルパラベン）
チタンホワイト
水
１０重量部
２重量部
０、０５重量部
０．２重量部
０．２重量部
（最終形態に於ける重量部）
実施例３
実施例２の１α−（ＯＨ）−Ｄ３に代えて、工α．２５
− （ＯＨ） ２−Ｄ３を用い、以下同様にしてｌα．
２５− （ＯＨ） ２−Ｄ３を■カプセル当り１埒を含
有する軟カプセル剤を得た。Shell formulation example Gelatin Glycerin Preservative (ethylparaben) Titanium white water 10 parts by weight 2 parts by weight 0, 05 parts by weight 0.2 parts by weight 0.2 parts by weight (parts by weight in final form) Example 3 Example In place of 1α-(OH)-D3 in 2. 25
- (OH) 2-D3 and lα.
Soft capsules containing 1 g of 25-(OH)2-D3 per capsule were obtained.
実施例４
実施例２の１α−（ＯＨ）−Ｄ３に代えて、１α，２４
Ｒ− （ＯＨ） ２−Ｄ３を用い、以下同様にして１α
，２４Ｒ− （ＯＨ） ２−Ｄ３をエカプセル当り１埒
を含有する軟カプセル剤を得た。Example 4 In place of 1α-(OH)-D3 in Example 2, 1α,24
Using R- (OH) 2-D3, 1α in the same manner
, 24R- (OH) 2-D3 was obtained in a soft capsule containing 1 gram per capsule.
Claims (1)
とを特徴とする抗血栓症剤。(1) An antithrombotic agent characterized by containing 1α-hydroxyvitamin D_3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24470890A JPH03169819A (en) | 1983-08-02 | 1990-09-14 | Antithrombotic agent containing 1alpha-hydroxyvitamin d3 compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14132383A JPS6045516A (en) | 1983-08-02 | 1983-08-02 | Physiologically active agent containing 1alpha- hydroxyvitamin d3 |
| JP24470890A JPH03169819A (en) | 1983-08-02 | 1990-09-14 | Antithrombotic agent containing 1alpha-hydroxyvitamin d3 compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14132383A Division JPS6045516A (en) | 1983-08-02 | 1983-08-02 | Physiologically active agent containing 1alpha- hydroxyvitamin d3 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03169819A true JPH03169819A (en) | 1991-07-23 |
Family
ID=26473579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24470890A Pending JPH03169819A (en) | 1983-08-02 | 1990-09-14 | Antithrombotic agent containing 1alpha-hydroxyvitamin d3 compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03169819A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6045516A (en) * | 1983-08-02 | 1985-03-12 | Kureha Chem Ind Co Ltd | Physiologically active agent containing 1alpha- hydroxyvitamin d3 |
-
1990
- 1990-09-14 JP JP24470890A patent/JPH03169819A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6045516A (en) * | 1983-08-02 | 1985-03-12 | Kureha Chem Ind Co Ltd | Physiologically active agent containing 1alpha- hydroxyvitamin d3 |
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