JPH0615523B2 - S-alkylthio-L-cysteine sulfoxide compound, method for producing the same, antihyperlipidemic agent and strong liver agent containing the same - Google Patents
S-alkylthio-L-cysteine sulfoxide compound, method for producing the same, antihyperlipidemic agent and strong liver agent containing the sameInfo
- Publication number
- JPH0615523B2 JPH0615523B2 JP24327483A JP24327483A JPH0615523B2 JP H0615523 B2 JPH0615523 B2 JP H0615523B2 JP 24327483 A JP24327483 A JP 24327483A JP 24327483 A JP24327483 A JP 24327483A JP H0615523 B2 JPH0615523 B2 JP H0615523B2
- Authority
- JP
- Japan
- Prior art keywords
- thiosulfinate
- same
- amino
- allyl
- propanoic acid
- 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 - Lifetime
Links
- 239000003795 chemical substances by application Substances 0.000 title claims description 5
- 210000004185 liver Anatomy 0.000 title claims description 4
- 239000003524 antilipemic agent Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000004201 L-cysteine Substances 0.000 claims description 4
- 235000013878 L-cysteine Nutrition 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims 1
- CWMAKUHNGGQLGT-UHFFFAOYSA-N hydroxy-prop-2-enyl-sulfanylidene-$l^{4}-sulfane Chemical compound OS(=S)CC=C CWMAKUHNGGQLGT-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 102000003929 Transaminases Human genes 0.000 description 2
- 108090000340 Transaminases Proteins 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000001944 cysteine derivatives Chemical class 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical group SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 1
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical group CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- JDLKFOPOAOFWQN-UHFFFAOYSA-N allicin Chemical compound C=CCSS(=O)CC=C JDLKFOPOAOFWQN-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- -1 resortylformamide Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical group S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 本発明は一般式 で示される新規なシステイン誘導体及びその塩に関す
る。DETAILED DESCRIPTION OF THE INVENTION Relates to a novel cysteine derivative and a salt thereof.
一般式(I)の中、Ｒはアリル基又は炭素数１ないし５の
アルキル基を示す。In the general formula (I), R represents an allyl group or an alkyl group having 1 to 5 carbon atoms.
本発明によって提供される化合物(I)はＬ−システイン
のＳ位にアルキル又はアリルメルカプタンの硫黄原子が
結合し、それら硫黄原子の一つがスルフォキサイドにま
で酸化され、酸化硫黄原子においてＳ又はＲ構造を有す
る新規のシステイン誘導体であり、優れた薬理作用を示
すので医薬品として有望である。特に本化合物は高コレ
ステロール血症に対し、脱コレステロール（特にＬＤ
Ｌ）作用を示し、また肝臓細胞のトランスアミナーゼ正
常化作用を示すので、抗高脂血症剤及び強肝剤として有
用である。The compound (I) provided by the present invention has a sulfur atom of alkyl or allyl mercaptan bonded to the S-position of L-cysteine, one of these sulfur atoms is oxidized to sulfoxide, and an S or R structure is formed at the sulfur oxide atom. It is a novel cysteine derivative having and has promising as a drug because it exhibits an excellent pharmacological action. In particular, this compound is effective for removing cholesterol (especially LD
L) It has an action and a liver cell transaminase normalizing action, and is therefore useful as an antihyperlipidemic agent and a strong liver agent.
本化合物は遊離型又はその塩として使用する。塩として
は薬学的に許容される酸との塩であって、許容される酸
としては酢酸、クエン酸、酒石酸、乳酸、コハク酸、フ
マール酸、マレイン酸、リンゴ酸等があげられる。This compound is used in a free form or a salt thereof. The salt is a salt with a pharmaceutically acceptable acid, and examples of the acceptable acid include acetic acid, citric acid, tartaric acid, lactic acid, succinic acid, fumaric acid, maleic acid, malic acid and the like.
本発明の化合物又はその塩は脱コレステロール剤又は強
肝剤として経口投与又は非経口投与することができる。
投与量は体重、症状などに応じて異なるが大約１００な
いし１０００mgである。剤型は注射剤、錠剤、内服液
剤、散剤等いずれでもよいが、これら剤型の調製に際し
ては常法により賦形剤、溶解補助剤等を使用することが
できる。The compound of the present invention or a salt thereof can be orally or parenterally administered as a cholesterol-removing agent or a strong liver agent.
The dose varies depending on the body weight and symptoms, but is generally about 100 to 1000 mg. The dosage form may be any of injections, tablets, oral liquids, powders, etc. When preparing these dosage forms, excipients, solubilizing agents and the like can be used in a conventional manner.
本化合物(I)は次の方法により製造することができる。The compound (I) can be produced by the following method.
（式中のＲはアリル基又は炭素数１ないし５のアルキル
基を示す。） 本方法はＬ−システイン(II)に対し、中性附近において
アルキル又はアリルチオスルフィネート類(III)を作用
させるものである。ここに生成するＳ−アルキル（又は
アリル）チオ−Ｌ−システイン(IV)は良結晶性の物質で
あり、単離することなく次の反応に付してもよいが、最
終目標物Ｓ−アルキル−２−アミノ−プロパノイックア
シッド−３−チオスルフィネート又はＳ−アリル−２−
アミノ−プロパノイックアシッド−３−チオスルフィネ
ートスルフォキサイドの純度を高めるために一度本ステ
ップにおいて(IV)を単離するのがよい。(IV)の酸化は過
酸化水素、過硫酸アンモン、チオ尿素、過安息香酸等で
あり、溶媒は水であるが、水と混和しうるアセトン、テ
トラヒドロフラン、レゾチルホルムアミド、メタノール
等を単独又は混合溶媒として使用する。反応温度は室温
ないし氷冷下で行う。 (R in the formula represents an allyl group or an alkyl group having 1 to 5 carbon atoms.) In this method, L-cysteine (II) is treated with an alkyl or allyl thiosulfinate (III) in the vicinity of neutrality. It is what makes me. The S-alkyl (or allyl) thio-L-cysteine (IV) produced here is a substance of good crystallinity and may be subjected to the next reaction without isolation, but the final target product S-alkyl 2-Amino-propanoic acid-3-thiosulfinate or S-allyl-2-
In order to increase the purity of amino-propanoic acid-3-thiosulfinate sulfoxide, (IV) should be isolated once in this step. Oxidation of (IV) is hydrogen peroxide, ammonium persulfate, thiourea, perbenzoic acid and the like, the solvent is water, but it is miscible with water, acetone, tetrahydrofuran, resortylformamide, methanol or the like alone or mixed Used as a solvent. The reaction temperature is room temperature to ice-cooling.
反応液から(I)の単離と精製は常法にしたがい有機溶媒
添加による各異性体（Ｓ，Ｒ）の析出、結晶化、カラム
クロマトグラフィーによる分離精製等を行う。Isolation and purification of (I) from the reaction solution are carried out according to a conventional method such as precipitation of each isomer (S, R) by addition of an organic solvent, crystallization, and separation and purification by column chromatography.
以下実施例にしたがい説明する。A description will be given below according to an embodiment.
実施例 ジメチルジスルフィド18.8gに氷酢酸１２ｇを加え、氷
冷後に濃硫酸2.9gを加え、氷冷下で３０％過酸化水素水
22.5gを徐々に滴下する。１夜放置後分液し、上層をと
り、氷冷下に炭酸ナトリウムを徐々に加え、pHを７附近
に調節した後、Ｌ−システイン１５ｇを徐々に加え攪拌
する。１夜放置後、析出した結晶を減圧集し、有機溶
媒で軽く洗う。得られたＳ−メチル−２−アミノ−プロ
パノイックアシッド−３−チオスルフィネートを乾燥す
る。Ｓ−メチル−２−アミノ−プロパノイックアシッド
−３−チオスルフィネート２ｇを氷酢酸３０mlに懸濁
し、氷冷下に３０％過酸化水素水２mlを徐々に滴下した
後室温中でさらに３０分間攪拌し、ほぼ透明となった液
を４０℃以下にて減圧濃縮し濃厚液を得る。これに水を
２５０ml加えて溶かし静置すると、Ｓ−メチル−２−ア
ミノ−プロパノイックアシッド−３−チオスルフィネー
トスルフオキサイドの結晶が析出する。収量0.6g。Example 1 12 g of glacial acetic acid was added to 18.8 g of dimethyl disulfide, 2.9 g of concentrated sulfuric acid was added after cooling with ice, and 30% hydrogen peroxide solution was added under cooling with ice.
22.5 g is gradually added dropwise. After allowing to stand overnight, the mixture is separated, the upper layer is taken, sodium carbonate is gradually added under ice-cooling to adjust the pH to around 7, and then 15 g of L-cysteine is gradually added and stirred. After standing overnight, the precipitated crystals are collected under reduced pressure and washed lightly with an organic solvent. The S-methyl-2-amino-propanoic acid-3-thiosulfinate obtained is dried. 2 g of S-methyl-2-amino-propanoic acid-3-thiosulfinate was suspended in 30 ml of glacial acetic acid, and 2 ml of 30% hydrogen peroxide solution was gradually added thereto under ice-cooling, and further 30 minutes at room temperature. After stirring for a minute, the almost transparent liquid is concentrated under reduced pressure at 40 ° C. or lower to obtain a concentrated liquid. When 250 ml of water was added to this and dissolved and left to stand, crystals of S-methyl-2-amino-propanoic acid-3-thiosulfinate sulfoxide were precipitated. Yield 0.6g.
本化合物の同族体の合成収率、ＩＲ吸収スペクトル等に
ついては表Ｉに示す。Table I shows the synthetic yields, IR absorption spectra, and the like of homologues of this compound.
薬理作用と毒性については次の各実験を行った。Regarding the pharmacological action and toxicity, the following experiments were conducted.
実験例１． 四塩化炭素及びガラクトサミンで肝臓疾患を起させたラ
ット肝細胞のトランスアミナーゼ（ＧＰＴ）値を例えば
表Ｉ中のNo.１，３及び４の化合物は投与量各0.01，0.1
及び1.0mg/mlにて有意に（ｐ＜0.01又はｐ＜0.001）に
減少せしめた。Experimental example 1. The transaminase (GPT) level of rat hepatocytes that had liver disease caused by carbon tetrachloride and galactosamine, for example, the compounds Nos. 1, 3 and 4 in Table I were administered at doses of 0.01 and 0.1, respectively.
And 1.0 mg / ml significantly (p <0.01 or p <0.001).
実験例２． 表Ｉ中のNo.１，３及び４の化合物はラットにコレステ
ロールを同時に与え、その代謝を調べた結果各物質とも
0.5％添加群において血清コレステロールを有意に（ｐ
＜0.001）低下せしめた。ただしＨＤＬコレステロール
は低下させなかった。Experimental example 2. The compounds Nos. 1, 3 and 4 in Table I simultaneously gave cholesterol to rats, and their metabolism was investigated.
Significantly increased serum cholesterol (p
<0.001) It decreased. However, HDL cholesterol was not lowered.
実験例３． マウスを用いて経口投与によるＬＤ５０値は例 えば表Ｉ中No.１の化合物で１４ｇ／Kg、No.３の化合物
で１０ｇ／Kg、No.４の化合物で１６ｇ／Kgであった。Experimental example 3. Example of LD 50 value by oral administration in mice For example, the compound No. 1 in Table I was 14 g / Kg, the compound No. 3 was 10 g / Kg, and the compound No. 4 was 16 g / Kg.
Claims (4)
を表わす） で示されるＳ−アルキル−２−アミノ−プロパノイック
アシッド−３−チオスルフィネート又はＳ−アリル−２
−アミノ−プロパノイックアシッド−３−チオスルフィ
ネート化合物及びその薬学的に許容される非毒性の酸と
の塩。1. A general formula (In the formula, R represents an allyl group or an alkyl group having 1 to 5 carbon atoms). S-alkyl-2-amino-propanoic acid-3-thiosulfinate or S-allyl-2
-Amino-propanoic acid-3-thiosulfinate compounds and their pharmaceutically acceptable salts with non-toxic acids.
−プロペン−１−チオスルフィネート） （式中Ｒはアリル基又は炭素数１ないし５のアルキル基
を表わす） を中性附近で反応せしめ、酸化剤により酸化させること
を特徴とする 一般式 （式中Ｒはアリル基又は炭素数１ないし５のアルキル基
を表わす） で示されるＳ−アルキル−２−アミノ−プロパノイック
アシッド−３−チオスルフィネート又はＳ−アリル−２
−アミノ−プロパノイックアシッド−３−チオスルフィ
ネート化合物の製造方法。2. L-cysteine and general formula (S-alkyl-1-thiosulfinate or S- (2
-Propene-1-thiosulfinate) (wherein R represents an allyl group or an alkyl group having 1 to 5 carbon atoms) in the vicinity of neutrality and is oxidized by an oxidizing agent. (In the formula, R represents an allyl group or an alkyl group having 1 to 5 carbon atoms). S-alkyl-2-amino-propanoic acid-3-thiosulfinate or S-allyl-2
-A process for preparing an amino-propanoic acid-3-thiosulfinate compound.
を表わす） で示されるＳ−アルキル−２−アミノ−プロパノイック
アシッド−３−チオスルフィネート又はＳ−アリル−２
−アミノ−プロパノイックアシッド−３−チオスルフィ
ネート化合物を含有する抗高脂血症剤。3. General formula (In the formula, R represents an allyl group or an alkyl group having 1 to 5 carbon atoms). S-alkyl-2-amino-propanoic acid-3-thiosulfinate or S-allyl-2
-An antihyperlipidemic agent containing an amino-propanoic acid-3-thiosulfinate compound.
を表わす） で示されるＳ−アルキル−２−アミノ−プロパノイック
アシッド−３−チオスルフィネート又はＳ−アリル−２
−アミノ−プロパノイックアシッド−３−チオスルフィ
ネート化合物を含有する強肝剤。4. A general formula (In the formula, R represents an allyl group or an alkyl group having 1 to 5 carbon atoms). S-alkyl-2-amino-propanoic acid-3-thiosulfinate or S-allyl-2
-A strong liver agent containing an amino-propanoic acid-3-thiosulfinate compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24327483A JPH0615523B2 (en) | 1983-12-22 | 1983-12-22 | S-alkylthio-L-cysteine sulfoxide compound, method for producing the same, antihyperlipidemic agent and strong liver agent containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24327483A JPH0615523B2 (en) | 1983-12-22 | 1983-12-22 | S-alkylthio-L-cysteine sulfoxide compound, method for producing the same, antihyperlipidemic agent and strong liver agent containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60132956A JPS60132956A (en) | 1985-07-16 |
| JPH0615523B2 true JPH0615523B2 (en) | 1994-03-02 |
Family
ID=17101426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24327483A Expired - Lifetime JPH0615523B2 (en) | 1983-12-22 | 1983-12-22 | S-alkylthio-L-cysteine sulfoxide compound, method for producing the same, antihyperlipidemic agent and strong liver agent containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0615523B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU8003091A (en) * | 1990-04-09 | 1991-10-30 | Rockefeller University, The | Method and agents for the selective reduction of lp(a) |
| US5272166A (en) * | 1990-04-09 | 1993-12-21 | The Rockefeller University | Method for selective reduction of Lp(a) |
-
1983
- 1983-12-22 JP JP24327483A patent/JPH0615523B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60132956A (en) | 1985-07-16 |
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