JPS58198465A - Beta-alanylcysteamine derivative - Google Patents
Beta-alanylcysteamine derivativeInfo
- Publication number
- JPS58198465A JPS58198465A JP57082155A JP8215582A JPS58198465A JP S58198465 A JPS58198465 A JP S58198465A JP 57082155 A JP57082155 A JP 57082155A JP 8215582 A JP8215582 A JP 8215582A JP S58198465 A JPS58198465 A JP S58198465A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- salt
- compound shown
- beta
- mercaptoethylamine
- Prior art date
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Abstract
Description
【発明の詳細な説明】
本発明は式ＣＩ〕で表わされる化合物およびその塩類に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to compounds represented by formula CI and salts thereof.
Ｒ１−Ｃ＞（ＣＨ２０）。−ＣＯＮＨＣ鶴ｃｎ２ｃｏ−
〔式中 Ｒ１は水素原子、低級アルキル基また株低級ア
ルコキシ基を Ｒ２は水素原子またはカルボキシル）ｋ
を、ｎｒｉＯまたは１を示す。〕本発明化合物の主骨格
であるβ−アラニルシステアミンはパンテチンの構成物
質として古くから知られている。パンテチン社体内で速
やかに、エネルギー代謝、脂質代謝等［ｆｉ要な役割を
有するコエンザイムＡＫ変換される。本発明者らは上記
の酸点よりβ−アラニルシステアミンの誘導体について
、鋭意研究を行った結果９本発明化合物ｒＩＪが脂質代
謝改善作用を有し、肝臓疾患治療剤として有用でるる事
を見い出した。R1-C>(CH20). -CONHC Tsuru cn2co-
[In the formula, R1 is a hydrogen atom, a lower alkyl group or a lower alkoxy group, and R2 is a hydrogen atom or a carboxyl group]k
, nriO or 1. [beta]-alanylcysteamine, which is the main skeleton of the compound of the present invention, has been known for a long time as a constituent of pantethine. Pantethine is quickly converted into coenzyme AK, which plays an important role in energy metabolism, lipid metabolism, etc., within the body. The present inventors conducted intensive research on derivatives of β-alanylcysteamine from the above acid site and found that the compound rIJ of the present invention has a lipid metabolism improving effect and is useful as a therapeutic agent for liver diseases. Ta.
本発明化合物ｒＩ］は１例えば式［［）で表わされる化
合物を式〔臘〕て表わされる化合物又はその反応性誘導
体（例えば、酸無水物、混合酸無水物等）と反応させる
ことによって合成することができる。The compound rI of the present invention is synthesized by reacting a compound represented by the formula [[) with a compound represented by the formula [臘] or a reactive derivative thereof (e.g., acid anhydride, mixed acid anhydride, etc.). be able to.
〔１１〕
Ｒ”−ｅ！＋−（ＣＨ２０）ｎ−ＣＯＸ −ＣＩ’３［
１１１］
〔式中、Ｘはハロゲン原子ｉたは水ｌＩ！基を示す。〕
本発明化合物は必要に応じて、す） ＩＪウム塩。[11] R"-e!+-(CH20)n-COX-CI'3[
111] [In the formula, X is a halogen atom i or water lI! Indicates the group. ]
The compound of the present invention may optionally be an IJium salt.
カリウム塩、カルシウム塩、アルミニウム塩、アンモニ
ウム塩、ジエチルアミン塩やトリエタノールアミン塩な
どの医薬として許容される塩とすることができる。It can be a pharmaceutically acceptable salt such as a potassium salt, a calcium salt, an aluminum salt, an ammonium salt, a diethylamine salt or a triethanolamine salt.
以下に実施例を示す。Examples are shown below.
実施例１゜
Ｎ、Ｓ−ジベンジルオキシカルボニル−β−アラニル−
２−メルカプトエチルアミンの製造β−ア２ニルー２−
メルカプトエチルアミン塩酸塩（９，０？ ）の４Ｎ水
酸化ナトリウム溶液（１２，３ｍ／ｌこ、ベンジルオキ
シカルボニルクロリド（１６，７ｙ）及び４． Ｎ水酸
化ナトリウム溶液（２４，６ＩＩ／）を水冷撹拌上同時
滴下する。滴下終了後氷冷Ｖ−３０分間、さらに室温下
３０分間撹拌する。反応液を酢酸エチルで抽出し、有機
層を塩酸、水、飽和★塩水の１１で洗浄する。この溶液
を無水硫酸マグネシウムで乾傑後減圧濃動し標記化合物
１５ノ（収率７４％）を得る。Example 1゜N,S-dibenzyloxycarbonyl-β-alanyl-
Production of 2-mercaptoethylamine β-anyl-2-
Mercaptoethylamine hydrochloride (9,0?) in a 4N sodium hydroxide solution (12,3ml/l), benzyloxycarbonyl chloride (16,7y) and a 4.N sodium hydroxide solution (24,6II/l) in a water-cooled mixture with stirring. Add dropwise to the top at the same time. After completion of the dropwise addition, stir on ice for 30 minutes and then at room temperature for 30 minutes. Extract the reaction solution with ethyl acetate, and wash the organic layer with hydrochloric acid, water, and saturated brine. This solution After drying with anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure to obtain the title compound 15 (yield 74%).
融点１２１〜１２２℃（酢酸エチル）
Ｉ ｌ’ｔ （にＢｒ、（＊−’）
３３１５．３２９０．１７０８，１６８２．１６４２゜
１５４２．１５３６，１２６８，１２４８．Ｊ １４０
゜７４２．６９６
ＮＭＲ（ＣＤＣＩ、、δ）
２−１４〜２−５３ （２Ｈ１ｍ 、＞Ｎ ＣＨ２Ｃ）
ＬＪ ＣＯ） 。Melting point: 121-122℃ (Ethyl acetate)
゜742.696 NMR (CDCI, δ) 2-14 to 2-53 (2H1m, >N CH2C)
LJ CO).
２．８１〜３．１６ （２）１． ｍ 、 、；ＮＣ）
ｉ、、Ｃ告５ＣＯ−） 。2.81-3.16 (2)1. m, , ;NC)
i, 5CO-).
３．４４ （４Ｈ、ｑ 、Ｊ＝５．６Ｈｚ 、ンＮＣ
ル、Ｃ１１２ＣＯ−及び＞ＮＣＨ２Ｃｌ１□５ＣＯ−）
。3.44 (4H, q, J=5.6Hz, NC
, C112CO- and >NCH2Cl1□5CO-)
.
５．０４及び５．１７（４Ｈ，大々Ｓ。5.04 and 5.17 (4H, big S.
ＯＣル０ＣＯＮ）ｉ−及びＯＣ馬ｏｃｖＳ−＞。OC le 0CON) i- and OC horse ocvS->.
５．３３〜５．８３ （ＩＨ、ｂｒ 、−ＣＯＮ）ｉ−
）。5.33-5.83 (IH, br, -CON)i-
).
６．１３〜６．５６（ＩＨ，ｂｙ、−ＣＯＮＨ−）。6.13-6.56 (IH, by, -CONH-).
７．２７及び７．３０（ＩＯＨ，夫々８．男香族Ｈ）Ｔ
ＬＣＲｆ イ＊（ａ’ 二 〇、 ４ ｄ（ａ）ニジ
リカゲル、ベンゼン−帷咳エチルー酢＃（２５： ２５
： １ ）
実施例２゜
Ｎ、Ｓ−ジベンゾイル−β−アラニル−２−メルカプト
エチルアミンの製造
β−アラニル−２−メルカプトエチルアミン塩酸塩＜
ｓ、ｏ ｙ ＞の４Ｎ水酸化ナトリウム溶液（６，８鰐
／ ）に、ベンゾイルクロリド（７，６９＞及び４Ｎ水
酸化ナトリウム溶液（１３，５鰐／）を水冷＆拌下同時
簡下する。以下実施例１と同様に操作Ｌ−、標記化合物
８．８ ｆｊ！ （収率９１％）を得る。7.27 and 7.30 (IOH, respectively 8. Otokozoku H) T
LCRf i*(a' 20, 4 d(a) Nijirica gel, benzene-ethyl vinegar #(25: 25
: 1) Example 2 Preparation of N,S-dibenzoyl-β-alanyl-2-mercaptoethylamine β-alanyl-2-mercaptoethylamine hydrochloride<
Benzoyl chloride (7,69>) and a 4N sodium hydroxide solution (13,5/l) are simultaneously added to a 4N sodium hydroxide solution (6,8/l) with water cooling and stirring. The following procedure was carried out in the same manner as in Example 1 to obtain 8.8 fj! (yield 91%) of the title compound.
融点１５４〜１５５℃（水−エタノール）ＩＲ（ＫＢｒ
、側 ）
３３０５．１６５７，１６４０．１６３２，１５３８゜
１２０４、９１５．６９Ｏ
ＮＭＲ（ＤＭＳＯ−ｄ６．δ）
２．４４ （２８、ｔ 、Ｊ＝７．０Ｈｚ ） 。Melting point 154-155°C (water-ethanol) IR (KBr
, side) 3305.1657, 1640.1632, 1538°1204, 915.69O NMR (DMSO-d6.δ) 2.44 (28, t, J=7.0Hz).
２．９８〜：Ｌ７７ （６Ｈ、ｍ 。2.98~: L77 (6H, m.
７．２７〜８−０１ （１０Ｈ、ｍ 、芳香族１１）。7.27-8-01 (10H, m, aromatic 11).
８．１４ （ＩＨ、ｔ 、Ｊ＝５．０Ｈｚ 、Ｃ０Ｎ）
ｌ−） 。8.14 (IH, t, J=5.0Hz, C0N)
l-).
８．４１ （ＩＨ、ｔ 、 Ｊ 〜６．０Ｈｚ 、 Ｃ
０ＮＨ−）ＴＬＣＲｆ値（ｂｌ 、 ９．５３
（ｂ）ニジリカゲルａ１エチル−クロロホルム−酢酸（
７：５：１）
同様すｒｌ、てＮ、Ｓ−ビス〔（４−メトキシ）ベンジ
ルオキシカルボニル〕−β−アラニＡ／、−２−メルカ
プトエチルアミンおよびＮ、Ｓ−ビス〔（４−メチル）
ベンジルオキシカルボエル１−β−アラニル−２−メル
カプトエチルアミンケ得ることができる。ｌ
出−人 谷大製薬株式会社
代理人 滝 川 敏 雄
手続補正書 （自発）
特許庁長官 若杉和夫殿
１、事件の表示
昭和５７年特許願第８２１５５号
２、発明の名称
β−アラニルシステアミン誘導体
３、補正をする者
事件との関係 特許出願人
大阪′市東淀用区下新庄３丁目９番１９号明細書特許請
求の範囲の欄および発明の詳細な説明の欄
６、補正の内容
（１） 明細書特許請求の範囲の欄を別紙のように訂
正する。8.41 (IH, t, J~6.0Hz, C
0NH-) TLCRf value (bl, 9.53 (b) Nijilica gel a1 ethyl-chloroform-acetic acid (
7:5:1) Similarly, N,S-bis[(4-methoxy)benzyloxycarbonyl]-β-alaniA/,-2-mercaptoethylamine and N,S-bis[(4-methyl)
Benzyloxycarboel 1-β-alanyl-2-mercaptoethylamine can be obtained. l Source: Toshio Takigawa, agent for Tanidai Pharmaceutical Co., Ltd. Procedural amendment (voluntary) Commissioner of the Japan Patent Office Kazuo Wakasugi1, Indication of the case 1982 Patent Application No. 821552, Name of the invention β-alanylcysteamine Derivative 3, Relationship with the case of the person making the amendment Patent applicant No. 3-9-19 Shimoshinjo, Higashiyodoyo-ku, Osaka City, Claims column and Detailed description of the invention column 6, Contents of amendment (1) ) Correct the scope of the specification and claims as shown in the attached sheet.
（２）同書第１頁下第４〜５行化学式ＣＩ）を次のよう
に訂正する。(2) The chemical formula CI) in the 4th to 5th lines of the bottom of page 1 of the same book is corrected as follows.
ｒ Ｒ” ０（ＣＨ２０）、、−ＣＯＮＨＣ鴇Ｃ鴇ＣＯ
−（３）同書第１頁終行ｒ ｎ ＦｉＯまたは１」を１
ｍおよびｎＦｉ同一か又は異なって◎またはｌ」と訂正
する。r R” 0 (CH20),, -CONHC 鴇C 驇CO
-(3) End line of page 1 of the same book r n FiO or 1” to 1
Correct "m and nFi are the same or different, ◎ or l".
（４）同書第２頁第１４行〜下第２行を次のよ゛うに訂
正する。(4) Page 2 of the same book, line 14 to line 2 below, are corrected as follows.
Ｒ’０（ｃｎ２ｏ）、−ｃｏｘ −［１］ｌ］
〔式中、 Ｒ３ｔｊ水素１１ 子ｔ ｆｃ Ｉｄ Ｒ”
−ｃ＞（ＣＨ，Ｏ）、−Ｃｏ−を、Ｘ＃ｉハロゲン原子
または水酸基を。R'0(cn2o), -cox -[1]l] [In the formula, R3tj hydrogen 11 child t fc Id R"
-c>(CH,O), -Co-, X#i halogen atom or hydroxyl group.
ｐはｍまたｉｔｎを示す。〕 Ｊ
（５）同書第５Ｔｉ第１１行ｒＪ＝７．０Ｈｚ）ＪＩＩ
ｒｒＪ＝７．０Ｈｚ、ンＮＣ）Ｉ２ＣＨ２Ｃｏ−）Ｊと
訂正する。p represents m or itn. ] J (5) Ibid. No. 5 Ti, line 11 rJ = 7.0 Hz) JII
Correct it as rrJ=7.0Hz, NC)I2CH2Co-)J.
（６）同書第５頁第１５行および第１６行ｒｃＯＮＨ−
）Ｊをｒ−ＣＯＮＨ−）Ｊと訂正する。(6) Same book, page 5, lines 15 and 16 rcONH-
)J is corrected as r-CONH-)J.
（７）同書第６頁第５行の次に次の文を押入する。(7) Insert the following sentence next to page 6, line 5 of the same book.
［上記Ｎ、Ｓ−ビス〔（４−メトキシ）ベンジルオキシ
カルボニル〕−β−アラニル−２−メルカプトエチルア
ミンの物性は次の通りでるる〇収率８３％
融点１４２．５〜１４４℃（メタノール）ＩＲ（ＫＢｒ
、ｃＩＩ−”）
３３４５．３３００，１７００．１６８２．１６４４゜
１５３９．１５２７．１２４０．１１４６ＮＭＲ（ＣＤ
Ｃｌ３．δ）
２．３１ （２Ｈ、ｔ 、 Ｊ＝６．０ Ｈｚ 、 −
ＮＨＣ）１２ＣＨ，Ｃｏ −）２．９５ （２８、ｔ
、 Ｊ ＝６．０Ｈｚ 、−ＮＨＣ）１２ＣＨ２８００
−）３．４２ （４Ｈ、ｍ 、 −ＮＨＣＨ，ＣＨ，Ｃ
０ＮＨ（Ｊ（２ＣＨ，５−）３．７５ （６１１、ｓ
、−０ＣＨ３Ｘ２ ）４．９８ （２Ｈ、８、ＣＨ３０
ＱＣＨ２０−）ｓ、ｔ ａ Ｃ２Ｈ、ｌ 、 ｃＨ３ｏ
Ｑｃす２Ｏ−）５．２５〜５．６５（ＩＨ，ｂｒ、−Ｃ
ＯＮＨ−）５．９９〜６．４７（ＩＨ，ｂｒ、−ＣＯＮ
Ｈ−）ＴＬＣＲｆＭ：０．３１’）、０．６７（ｂｌ実
施例３゜
Ｓ−ベンゾイル−Ｎ−（ベンジルオキシカルボニル−β
−アラニル）−２−メルカプトエチルアミンの製造
Ｎ−（ベンジルオキシカルボニル−β−アシエル）−２
−ブロモエチルアミン（１０ｐ、０．０３毫ル）のア七
トン（２５０ｄ ）溶液に、チオ安息香酸カリウム塩（
５，３５ｆ！ 、 ０．０３モル）のア七トン（１００
ｓｄ）溶液を加える。１時間撹拌後不溶物を戸別し、Ｐ
液を減圧濃縮する。得られる残ａｔクロロホルムに溶解
し、水酸化ナトリウム水溶液、水、飽和食塩水の順で洗
浄する。この溶液を無水硫酸マグネシウムで乾燥後減圧
濃縮しＩＩＡ配化合物７．９ ｆｉ！ （収率６８％）
を得る。[The physical properties of the above N,S-bis[(4-methoxy)benzyloxycarbonyl]-β-alanyl-2-mercaptoethylamine are as follows: Yield: 83% Melting point: 142.5-144°C (methanol) IR (KBr
, cII-'') 3345.3300,1700.1682.1644゜1539.1527.1240.1146NMR (CD
Cl3. δ) 2.31 (2H, t, J=6.0 Hz, -
NHC)12CH,Co-)2.95 (28, t
, J=6.0Hz, -NHC)12CH2800
-)3.42 (4H, m, -NHCH,CH,C
0NH(J(2CH,5-)3.75 (611,s
, -0CH3X2 )4.98 (2H,8,CH30
QCH20-)s, ta C2H, l, cH3o
Qcsu2O-) 5.25-5.65 (IH, br, -C
ONH-) 5.99-6.47 (IH, br, -CON
H-)TLCRfM: 0.31'), 0.67 (bl Example 3゜S-benzoyl-N-(benzyloxycarbonyl-β
-Alanyl)-2-mercaptoethylamine production N-(benzyloxycarbonyl-β-acyel)-2
- To a solution of bromoethylamine (10 p, 0.03 mmol) in a7tone (250 d) is added potassium thiobenzoate salt (
5,35f! , 0.03 mol) of a7ton (100
sd) Add solution. After stirring for 1 hour, remove the insoluble matter, P
Concentrate the liquid under reduced pressure. The resulting residue is dissolved in chloroform and washed with an aqueous sodium hydroxide solution, water, and saturated saline in this order. This solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give IIA compound 7.9 fi! (yield 68%)
get.
融点１１５〜１１８℃（酢酸エチル）
ＩＲ（ＫＢｒ、ｃＩＲ）
３３２０．１６８８．１６５８，１６４８，１５４４゜
１２６８．１２０２，９１４．６９３
ＮＭＲ（ＣＤＣｌ３．δ）
２．３６ （２Ｈ、ｔ 、 Ｊ＝６．０Ｈｚ 、 −Ｎ
ＨＣ）Ｌ、Ｃ巧Ｃｏ−）３．０３〜３．７４ （６）１
． ｍ 。Melting point 115-118°C (ethyl acetate) IR (KBr, cIR) 3320.1688.1658, 1648, 1544° 1268.1202, 914.693 NMR (CDCl3.δ) 2.36 (2H, t, J=6. 0Hz, -N
HC) L, C Takumi Co-) 3.03~3.74 (6) 1
．． m.
−ＮＨＣＨ２ＣＨ２ＣＯＮＨＣ馬ＣＨ２５−）５．０４
＜ ２ Ｈ、ａ 、 −ａｎ２Ｋ））５．３０〜５．
７４（ＩＨ，ｂｒ、−ＣＯＮＨ−）６．０９〜６．６７
（１１（、ｂｒ、−ＣＯＮＨ−）７．２８（５Ｈ，８、
−ｃＨ２（ｙ甲
ＴＬＣＲｆｍ”’ ： ０．３ ３
Ｊ別 紙
特許請求の範囲
式ｒＩ）で表わされる化合物およびその塩類。-NHCH2CH2CONHC Horse CH25-) 5.04
<2H, a, -an2K)) 5.30-5.
74 (IH, br, -CONH-) 6.09-6.67
(11(,br,-CONH-)7.28(5H,8,
-cH2(yATLCRfm"': 0.3 3
Appendix J Claims Compounds represented by formula rI) and salts thereof.
Ｒ’％Σ（Ｃ）１２０３ｍ−ＣＯＮＨＣ）Ｌ、ＣＨ２Ｃ
０−ｃ式中、Ｒ”Ｆｉ水素原子、低級アルキル基または
低級アルコキシ基を Ｈ２は水素原子またはカルボキシ
ル基ｔ１ｍおよびｎは同一か又は異なって０またｉｊｌ
を示す○〕R'%Σ(C)1203m-CONHC)L, CH2C
0-c formula, R"Fi hydrogen atom, lower alkyl group or lower alkoxy group H2 is a hydrogen atom or carboxyl group t1m and n are the same or different and 0 or ijl
○ indicates
Claims (1)
ルコキ、シ基を Ｂ２は水素原子またはカルボキシル基
を、ｎｔｉＯまたはｌを示す。〕[Claims] A compound represented by formula [1] and salts thereof. [In the formula, R1 represents a hydrogen atom, a lower alkyl group represents a lower alkoxy group, and B2 represents a hydrogen atom or a carboxyl group, and represents ntiO or l. ]
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57082155A JPS58198465A (en) | 1982-05-14 | 1982-05-14 | Beta-alanylcysteamine derivative |
| US06/488,100 US4552765A (en) | 1982-05-14 | 1983-04-25 | Aletheine derivatives |
| IT21040/83A IT1164218B (en) | 1982-05-14 | 1983-05-11 | ALETEIN DERIVATIVES |
| GB08313145A GB2123815B (en) | 1982-05-14 | 1983-05-12 | Aletheine derivatives |
| DE3317529A DE3317529C2 (en) | 1982-05-14 | 1983-05-13 | ß-Aletheinderivate, processes for their preparation and pharmaceutical compositions containing them |
| FR8308048A FR2526792B1 (en) | 1982-05-14 | 1983-05-16 | ALETHEIN DERIVATIVES USEFUL FOR THE TREATMENT OF HEPATIC LESIONS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57082155A JPS58198465A (en) | 1982-05-14 | 1982-05-14 | Beta-alanylcysteamine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58198465A true JPS58198465A (en) | 1983-11-18 |
| JPH0261451B2 JPH0261451B2 (en) | 1990-12-20 |
Family
ID=13766541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57082155A Granted JPS58198465A (en) | 1982-05-14 | 1982-05-14 | Beta-alanylcysteamine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58198465A (en) |
-
1982
- 1982-05-14 JP JP57082155A patent/JPS58198465A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0261451B2 (en) | 1990-12-20 |
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