JPH03258721A - Pharmaceutical composition - Google Patents
Pharmaceutical compositionInfo
- Publication number
- JPH03258721A JPH03258721A JP5622190A JP5622190A JPH03258721A JP H03258721 A JPH03258721 A JP H03258721A JP 5622190 A JP5622190 A JP 5622190A JP 5622190 A JP5622190 A JP 5622190A JP H03258721 A JPH03258721 A JP H03258721A
- Authority
- JP
- Japan
- Prior art keywords
- salt
- hypotensor
- chloro
- oxoimidazolidine
- derivative
- 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.)
- Granted
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000002220 antihypertensive agent Substances 0.000 claims description 4
- 229940030600 antihypertensive agent Drugs 0.000 claims description 2
- KLZWOWYOHUKJIG-BPUTZDHNSA-N imidapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)CC1=CC=CC=C1 KLZWOWYOHUKJIG-BPUTZDHNSA-N 0.000 claims 1
- XABUPXIZLMAQKF-UHFFFAOYSA-N 8-chloro-1,2-benzothiazepine Chemical class C1=CC=NSC2=CC(Cl)=CC=C21 XABUPXIZLMAQKF-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 3
- GYKFWCDBQAFCLJ-RTWAWAEBSA-N [(2s,3s)-8-chloro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=C(Cl)C=C2S1 GYKFWCDBQAFCLJ-RTWAWAEBSA-N 0.000 abstract 1
- 108010058865 angiotensinase Proteins 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 230000002459 sustained effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- -1 turhitz Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KZKRPYCBSZIQKN-UHFFFAOYSA-N 2-Imidazolidone-4-carboxylic acid Chemical compound OC(=O)C1CNC(=O)N1 KZKRPYCBSZIQKN-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical class NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は、血圧降下剤として有用な医薬組成物に関する
。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a pharmaceutical composition useful as an antihypertensive agent.
(従来技術)
(+)−シス−2−(4−メトキシフェニル)−3−ア
セトキシ−5−(2−(ジメチルアミノ)エチル〕−8
−クロロ−2,3−ジヒドロ−15−ベンゾチアゼピン
−4(5H)−オンが血圧降下剤として有用な化合物で
あることは知られている(特開昭6l−103828)
。(Prior art) (+)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-(2-(dimethylamino)ethyl]-8
-Chloro-2,3-dihydro-15-benzothiazepin-4(5H)-one is known to be a useful compound as a hypotensive agent (Japanese Patent Application Laid-Open No. 61-103828).
.
また、(4S)−1−メチル−3−{(2S)−2−〔
N−((I 5)−1−エトキシカルボニル−3−フェ
ニルプロピル)アミノコプロピオニル)−2−オキソイ
ミダゾリジン−4−カルボン酸が、アンジオテンシン変
換酵素(ACE)阻害作用ををし、血圧降下剤として有
用な化合物であることも知られている(特開昭6O−1
3715)。Also, (4S)-1-methyl-3-{(2S)-2-[
N-((I5)-1-ethoxycarbonyl-3-phenylpropyl)aminocopropionyl)-2-oxoimidazolidine-4-carboxylic acid acts as an angiotensin converting enzyme (ACE) inhibitor and is a hypotensive agent. It is also known to be a useful compound as
3715).
(発明の構成及び効果)
本発明は、(+)−シス−2−(4−メトキシフェニル
)−3−アセトキシ−5−(2−(ジメチルアミノ)エ
チル〕−8−クロロ−2,3−ジヒドロ−1,5−ベン
ゾチアゼピン−4(5H)−オン(以下、8−クロロ−
ベンゾチアゼピン誘導体(1)と称する)又はその薬理
的に許容しうる塩と(4S)−1−メチル−3−{(2
S)−2−〔N−((I 5)−1−エトキシカルボニ
ル−3−フェニルプロピル)アミノコプロピオニル)−
2−オキソイミダゾリジン−4−カルボン酸(以下、オ
キソイミダゾリジン誘導体(IF)と称する)又はその
薬理的に許容しうる塩とを含む医N組成物である。(Structure and effects of the invention) The present invention provides (+)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-(2-(dimethylamino)ethyl]-8-chloro-2,3- Dihydro-1,5-benzothiazepin-4(5H)-one (hereinafter referred to as 8-chloro-
benzothiazepine derivative (1)) or a pharmacologically acceptable salt thereof and (4S)-1-methyl-3-{(2
S)-2-[N-((I 5)-1-ethoxycarbonyl-3-phenylpropyl)aminocopropionyl)-
This is a medical composition containing 2-oxoimidazolidine-4-carboxylic acid (hereinafter referred to as oxoimidazolidine derivative (IF)) or a pharmacologically acceptable salt thereof.
本発明の医薬組成物は、8−クロロ−ベンゾチアゼピン
誘導体(,1)又はその塩と、オキソイミダゾリジン誘
導体(II)又はその塩とを配合したものであり、各活
性成分を各々単独で投与する場合に較べて、より強い血
圧降下作用を示すと共に作用持続性が優れているいう利
点がある。The pharmaceutical composition of the present invention is a combination of an 8-chloro-benzothiazepine derivative (1) or a salt thereof and an oxoimidazolidine derivative (II) or a salt thereof, and each active ingredient is contained individually. Compared to the case of administration, it has the advantage of exhibiting a stronger blood pressure lowering effect and having an excellent duration of action.
8−クロロ−ベンゾチアゼピン誘導体(I)は、遊離化
合物もしくは塩酸塩、臭化水素酸塩、ヨウ化水素酸塩、
過塩素酸塩、硫酸塩、リン酸塩、シュウ酸塩、マレイン
酸塩、フマル酸塩、酒石酸塩、メタンスルホン酸塩の如
きその薬理学的に許容しうる酸付加塩としても投与でき
る。8-Chloro-benzothiazepine derivative (I) can be used as a free compound or as a hydrochloride, hydrobromide, hydroiodide,
It can also be administered as its pharmacologically acceptable acid addition salts such as perchlorates, sulfates, phosphates, oxalates, maleates, fumarates, tartrates, methanesulfonates.
オキソイミダゾリジン誘導体(If)は、遊離酸もしく
は塩酸塩、臭化水素酸塩、硫酸塩、リン酸塩、コハク酸
塩、マレイン酸塩、フマル酸塩、メタンスルホン酸塩、
リジン塩、オルニチン塩、ナトリウム塩、カリウム塩、
カルシウム塩、マグネシウム塩の如きその薬理的に許容
しうる塩の形でも投与できる。Oxoimidazolidine derivatives (If) are free acids or hydrochlorides, hydrobromides, sulfates, phosphates, succinates, maleates, fumarates, methanesulfonates,
Lysine salt, ornithine salt, sodium salt, potassium salt,
It can also be administered in the form of its pharmacologically acceptable salts such as calcium salts and magnesium salts.
これらの再活性成分化合物の配合比率は、8クロロ−ベ
ンゾチアゼピン誘導体(■)1に対し、オキソイミダゾ
リジン誘導体(II)を10分の1乃至当量とするのが
好ましく、また、−日当たりの投与量は、前記の配合比
率の範囲内で8−クロロ−ベンゾチアゼピン誘導体(r
)が3〜300■及びオキソイミダゾリジン誘導体(n
)が1〜100■であるのが望ましい。The blending ratio of these reactivating component compounds is preferably 1/10 to 1/1 equivalent of the oxoimidazolidine derivative (II) to 1 of the 8-chlorobenzothiazepine derivative (■); The dosage of the 8-chloro-benzothiazepine derivative (r
) is 3 to 300■ and oxoimidazolidine derivative (n
) is preferably 1 to 100 ■.
本発明の医薬組成物は、経口的にも非経口的にも用いる
ことができ、また両活性成分は単一製剤中に含有させた
ものであってもよく、各活性成分を別々の製剤とし、両
型剤をユニットとしたものでもよい。The pharmaceutical composition of the present invention can be used either orally or parenterally, and both active ingredients may be contained in a single formulation, or each active ingredient may be contained in separate formulations. , and both types of agents may be used as a unit.
経口投与する場合の剤型は、錠剤、散剤、カプセル剤、
顆粒剤の如き固形剤であってもよく、溶液、懸濁液の如
き液剤であってもよく、経口投与に適した医薬担体と共
に医薬製剤として使用することができる。かかる医薬担
体としては、例えば結合剤(シロップ、アラビアゴム、
ゼラチン、ツルヒツト、トラガント、ポリビニルピロリ
ドンなど)、賦形剤(乳糖、砂糖、コーンスターチ、リ
ン酸カリウム、ソルビット、グリシンなど)、潤滑剤(
ステアリン酸マグネシウム、タルク、ポリエチレングリ
コール、シリカなど)、崩壊剤(バレイショデンブンな
ど)及び湿潤剤(ラウリル硫酸ナトリウムなど)が挙げ
られる。For oral administration, dosage forms include tablets, powders, capsules,
It may be a solid preparation such as a granule, or a liquid preparation such as a solution or suspension, and can be used as a pharmaceutical preparation together with a pharmaceutical carrier suitable for oral administration. Such pharmaceutical carriers include, for example, binders (syrup, gum arabic,
gelatin, turhitz, tragacanth, polyvinylpyrrolidone, etc.), excipients (lactose, sugar, corn starch, potassium phosphate, sorbitol, glycine, etc.), lubricants (
magnesium stearate, talc, polyethylene glycol, silica, etc.), disintegrants (such as potato starch), and wetting agents (such as sodium lauryl sulfate).
一方、非経口的に投与する場合の剤型は、例えば注射用
蒸留水、生理的食塩水、ブドウ糖水溶液等を用いて注射
剤や点滴注射剤とするのが好ましい。On the other hand, the dosage form for parenteral administration is preferably an injection or a drip injection using, for example, distilled water for injection, physiological saline, aqueous glucose solution, or the like.
実験例
<SHRに対する降圧作用〉
(方法)
一夜絶食させた自然発症高血圧症ラッ) (SHR)を
1群5匹とし、検体投与群には、下記検体化合物(A)
及び/又は(B)をイオン交換水に溶解して強制経口投
与(投与!=各検体とも1 mg/kg) した。Experimental Example <Antihypertensive effect on SHR> (Method) A group of 5 spontaneously hypertensive rats (SHR) were fasted overnight, and the sample administration group received the following sample compound (A).
and/or (B) was dissolved in ion-exchanged water and administered orally by force (Administration! = 1 mg/kg for each specimen).
ラットの収縮期血圧を、テール プレステモダラフ法〔
ザ・ジャーナル・オフ゛・ラボラトリ−・アンド・クリ
ニック・メディシン、78,957(1971))によ
り、検体投与前と投与後1.3及び6時間口に測定し、
投与前に対する血圧低下度合を求めた。The systolic blood pressure of rats was measured using the tail plestemodaraf method [
According to The Journal of Laboratory and Clinic Medicine, 78,957 (1971)), it was measured orally before and 1.3 and 6 hours after administration of the sample.
The degree of blood pressure reduction compared to before administration was determined.
検体化合物(A)=8−クロロ−ベンゾチアゼピン誘導
体(1)のマレイン酸塩
検体化合物(B)ニオキソイミダゾリジン誘導体(I[
)の塩酸塩
血圧降下作用の効果判定は、下記の基準に従って行った
。Test compound (A) = maleate salt of 8-chloro-benzothiazepine derivative (1) Test compound (B) nioxoimidazolidine derivative (I[
) hydrochloride antihypertensive effect was evaluated according to the following criteria.
(結果)
結果は下記第1表の通りであり、検体(A)及び(B)
を併用した場合には、単独使用の場合に較べて、より強
い血圧降下作用を示すと共に作用持続性も優れているこ
とがわかる。(Results) The results are as shown in Table 1 below, and samples (A) and (B)
It can be seen that when used in combination, a stronger blood pressure lowering effect is exhibited and the duration of the action is also better than when used alone.
第 1 表Table 1
Claims (2)
3−アセトキシ−5−〔2−(ジメチルアミノ)エチル
〕−8−クロロ−2,3−ジヒドロ−1,5−ベンゾチ
アゼピン−4(5H)−オン又はその薬理的に許容しう
る塩と(4S)−1−メチル−3−{(2S)−2−〔
N−((1S)−1−エトキシカルボニル−3−フェニ
ルプロピル)アミノ〕プロピオニル}−2−オキソイミ
ダゾリジン−4−カルボン酸又はその薬理的に許容しう
る塩とを含む医薬組成物。(1)(+)-cis-2-(4-methoxyphenyl)-
3-acetoxy-5-[2-(dimethylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one or a pharmacologically acceptable salt thereof; (4S)-1-methyl-3-{(2S)-2-[
N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxoimidazolidine-4-carboxylic acid or a pharmaceutically acceptable salt thereof.
。(2) The pharmaceutical composition according to claim 1, which is an antihypertensive agent.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5622190A JPH0720868B2 (en) | 1990-03-07 | 1990-03-07 | Pharmaceutical composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5622190A JPH0720868B2 (en) | 1990-03-07 | 1990-03-07 | Pharmaceutical composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH03258721A true JPH03258721A (en) | 1991-11-19 |
JPH0720868B2 JPH0720868B2 (en) | 1995-03-08 |
Family
ID=13021052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP5622190A Expired - Lifetime JPH0720868B2 (en) | 1990-03-07 | 1990-03-07 | Pharmaceutical composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0720868B2 (en) |
-
1990
- 1990-03-07 JP JP5622190A patent/JPH0720868B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JPH0720868B2 (en) | 1995-03-08 |
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