JPH0291099A - 1-deoxymuramylpeptide derivative - Google Patents
1-deoxymuramylpeptide derivativeInfo
- Publication number
- JPH0291099A JPH0291099A JP63243522A JP24352288A JPH0291099A JP H0291099 A JPH0291099 A JP H0291099A JP 63243522 A JP63243522 A JP 63243522A JP 24352288 A JP24352288 A JP 24352288A JP H0291099 A JPH0291099 A JP H0291099A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- compound expressed
- acyl
- alpha
- 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
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims abstract description 6
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims abstract description 3
- 229960003767 alanine Drugs 0.000 claims abstract description 3
- 125000000539 amino acid group Chemical group 0.000 claims abstract description 3
- 229960001153 serine Drugs 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229960004295 valine Drugs 0.000 claims description 2
- 101100108100 Rattus norvegicus Acy1a gene Proteins 0.000 claims 1
- 101100108101 Rattus norvegicus Acy1b gene Proteins 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 38
- 150000002148 esters Chemical class 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010531 catalytic reduction reaction Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002510 pyrogen Substances 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960002920 sorbitol Drugs 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- XJBFOPHLDCXNPN-OZRXBMAMSA-N (2R)-2-[(2R,3S,4R,5S)-5-amino-3-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxypropanoic acid Chemical compound C1[C@H](N)[C@@H](O[C@@H](C(=O)O)C)[C@H](O)[C@H](O1)CO XJBFOPHLDCXNPN-OZRXBMAMSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000012591 Dulbecco’s Phosphate Buffered Saline Substances 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000240 adjuvant effect Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000000546 chi-square test Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 231100000668 minimum lethal dose Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
【発明の詳細な説明】
ＤＩ
〔式中、＾ｃｙｌは炭素数２〜６のアシル基を、ＸはＬ
−アラニン、Ｌ−セリン及びＬ−バリンより選ばれるア
ミノ酸残基を、ｎは１〜６の整数を、Ａは炭素数１０〜
２５のアルキル基を意味する〕で示される化合物及びそ
の塩に関する。[Detailed description of the invention] DI [In the formula, ^cyl is an acyl group having 2 to 6 carbon atoms, and X is L
- An amino acid residue selected from alanine, L-serine, and L-valine, n is an integer of 1 to 6, and A is a carbon number of 10 to
25, meaning an alkyl group] and salts thereof.
〈産業上の利用分野〉
式（Ｉ）の化合物は感染防御効果に優れ、医薬として有
用である。<Industrial Application Field> The compound of formula (I) has an excellent infection-preventing effect and is useful as a medicine.
〈従来の技術〉
１−デオキシムラミン酸を部分構造とする化合物として
は特開昭５７−２６６９８号公報に開示されたものが知
られている。しかしながら、該化合物が有する効果につ
いてはアジュバント効果が知られているのみであって、
感染防御効果は知られていない。<Prior Art> As a compound having 1-deoxymuramic acid as a partial structure, there is known a compound disclosed in JP-A-57-26698. However, the only known effect of this compound is its adjuvant effect;
Its effectiveness in preventing infection is unknown.
又、感染防御効果を有する化合物としては特公昭６２−
２７０９号公報に開示されたものが知られている。In addition, as a compound that has an infection-preventing effect,
One disclosed in Japanese Patent No. 2709 is known.
〈発明が解決しようとする問題点〉
本発明者等は感染防御効果に優れた化合物を見い出すべ
く鋭意検討した結果本発明を完成した。<Problems to be Solved by the Invention> The present inventors completed the present invention as a result of intensive studies to find a compound with excellent infection prevention effects.
〈発明の構成〉 本発明は式（Ｉ）の化合物及びその塩に関する。<Structure of the invention> The present invention relates to compounds of formula (I) and salts thereof.
式（Ｉ）におけるアルキル基としては、ドデシル、テト
ラデシル、ヘキサデシル、オクタデシル、エイコシル等
を、好ましくは炭素数１５〜１９のものをあげることが
できる。Examples of the alkyl group in formula (I) include dodecyl, tetradecyl, hexadecyl, octadecyl, and eicosyl, preferably those having 15 to 19 carbon atoms.
次に１式（１）の化合物の製造法を説明する。Next, a method for producing the compound of Formula 1 (1) will be explained.
（［）
（式中、＾ｃｙｌ、 ｎ及びＡは前記に同じであり、Ｒ
はベンジル基を示す、）
即ち１式（Ｉりの化合物を式（ＩＩＩ ）の化合物と縮
合させることにより式（ＴＶ）の化合物とすることがで
きる。該縮合方法としてはカルボジイミド法、アイント
ップ法、活性エステル法及び酸無水物法が採用しつる０
例えば１式（ＩＩ）の化合物を適当な溶媒中、Ｎ−ヒド
ロキシサクシンイミドの存在下ジシクロへキシルカルボ
ジイミドを反応させて式（ＩＩ）の化合物の活性エステ
ルを製し、これを式（ＩＩＩ ）の化合物と反応させる
ことにより式（１’Ｖ）の化合物を製することができる
。([) (wherein ^cyl, n and A are the same as above, R
represents a benzyl group) That is, a compound of formula (TV) can be obtained by condensing a compound of formula 1 (I) with a compound of formula (III).The condensation method includes the carbodiimide method and the Aintop method. , activated ester method and acid anhydride method are adopted.
For example, the active ester of the compound of formula (II) is prepared by reacting the compound of formula (II) with dicyclohexylcarbodiimide in the presence of N-hydroxysuccinimide in a suitable solvent, and this is converted into the active ester of the compound of formula (III). A compound of formula (1'V) can be produced by reacting with a compound.
式（ＩＶ）の化合物を酢酸等の酸の存在下処理すること
によりイソプロピリデンを除去することができる。次い
で、得られた化合物をパラジウム炭素等の触媒の存在下
接触還元することにより式（Ｉ）の化合物を製造するこ
とかできる。Isopropylidene can be removed by treating the compound of formula (IV) in the presence of an acid such as acetic acid. The compound of formula (I) can then be produced by subjecting the obtained compound to catalytic reduction in the presence of a catalyst such as palladium on carbon.
〈発明の効果〉
本発明の化合物は感染防御効果に優れ且つ発熱性が非常
に弱いものであった。従って本発明の化合物は感染防御
剤として優れたものである。<Effects of the Invention> The compounds of the present invention had excellent infection-preventing effects and very low pyrogenicity. Therefore, the compound of the present invention is excellent as an agent for preventing infection.
以下１本発明を更に実施例及び試験例によって説明する
が２本発明はこれらに限定されるものではない。The present invention will be further explained below with reference to Examples and Test Examples, but the present invention is not limited thereto.
実施例
１）Ｎ−（Ｎ−［２−Ｏ−（２−アセタミド−１，５−
アンヒドロ−２，３−ジデオキシ−４，６−０−イソプ
ロピリデン−Ｄ−グルシトール）−Ｄ−ラクトイル］−
Ｌ−アラニルーＤ−イソグルタミニル）−Ｎ−ステアロ
イル−Ｌ−リジンベンジルエステル
２−アセタミド−１，５−アンヒドロ−３−０−（［１
−１−カルボキシエチル）−２−デオキシ−４，Ｉｆ−
０−イソプロピリデン−Ｄ−グルシトール８０ｍｇを１
．４−ジキサン５ｍｌに溶解した後ジシクロへキシルカ
ルボジイミド １００ＢとＮ−ヒドロキシサクシンイミ
ド４８ｍｇを加え室温にて３０分間攪拌した。生じた不
溶物を濾別した後濾液を減圧濃縮した。得られた残漬と
Ｎ−［Ｌ−アラニル−Ｏ−イソグルタミニル］−Ｎ−ス
テアロイル−し−リジン ベンジルエステル トリフル
オロ酢酸塩２２０ｍｇをＮ、Ｎ−ジメチルホルムアミド
６ｍｌに溶解した後、トリエチルアミン０．１ｍｌを
加え、室温で１１時間攪拌した。減圧濃縮後、得られた
残渣をカラムクロマトグラフィーに供し、ジクロロメタ
ンーンタノール（２５：１．容量比）の溶出液を用いて
、標題化合物７０ｍｇを単離した。Example 1) N-(N-[2-O-(2-acetamido-1,5-
anhydro-2,3-dideoxy-4,6-0-isopropylidene-D-glucitol)-D-lactoyl]-
L-alanyl-D-isoglutaminyl)-N-stearoyl-L-lysine benzyl ester 2-acetamido-1,5-anhydro-3-0-([1
-1-carboxyethyl)-2-deoxy-4,If-
80 mg of 0-isopropylidene-D-glucitol
．． After dissolving in 5 ml of 4-dixane, dicyclohexylcarbodiimide 100B and 48 mg of N-hydroxysuccinimide were added and stirred at room temperature for 30 minutes. After the resulting insoluble matter was filtered off, the filtrate was concentrated under reduced pressure. After dissolving the obtained residue and 220 mg of N-[L-alanyl-O-isoglutaminyl]-N-stearoyl-cy-lysine benzyl ester trifluoroacetate in 6 ml of N,N-dimethylformamide, 0.1 ml of triethylamine was added. The mixture was added and stirred at room temperature for 11 hours. After concentration under reduced pressure, the obtained residue was subjected to column chromatography, and 70 mg of the title compound was isolated using an eluent of dichloromethane-tanol (25:1 by volume).
〔α） −５，３（Ｇ Ｏ，［ｉ、ジクロルメタン：
りロロホルム＝ １：１ （ｖ／ｖ） ）
チレン）、 １７４０ （エステル） 、 １６５０及
び１５６０ （アミド） 、 ８４０ （（ＣＨ３）
２Ｃ）２） Ｎ−（Ｎ−［２−Ｏ−（２−アセタミド
−１，５−アンヒドロ−２，３−ジデオキシ−Ｄ−グル
シド−ルー３−イル）−〇−ラクトシル］−Ｌ−アラニ
ルーＤ−イソグルタミニル）−ε
Ｎ−ステアロイル−し−リジン
上記化合物７０ｍｇを７０９６酢酸水溶液５ｍｌに溶解
し、４５℃にて５時間静置し、その後減圧濃縮した。得
られた残漬を酢酸１０ｍ１に溶解し、１０ｔパラジウム
炭素７０ｍｇを触媒として接触還元を行なつた。触媒を
濾別し、酢酸を用いて洗浄した。濾液、洗液を合して凍
結乾燥を行ない、標題化合物５０ｍｇを得た。[α) -5,3(G O, [i, dichloromethane:
Lyroloform = 1:1 (v/v) ) tyrene), 1740 (ester), 1650 and 1560 (amide), 840 ((CH3)
2C) 2) N-(N-[2-O-(2-acetamido-1,5-anhydro-2,3-dideoxy-D-glucido-3-yl)-〇-lactosyl]-L-alanyl D 70 mg of the above compound was dissolved in 5 ml of 7096 acetic acid aqueous solution, allowed to stand at 45°C for 5 hours, and then concentrated under reduced pressure. The obtained residue was dissolved in 10 ml of acetic acid, and catalytic reduction was performed using 70 mg of 10t palladium carbon as a catalyst. The catalyst was filtered off and washed with acetic acid. The filtrate and washing liquid were combined and freeze-dried to obtain 50 mg of the title compound.
融点 ２１１〜２１５℃（分解）
〔α） ＋５．２ （Ｇ Ｏ，５，ジクロルメタン
：りロロホルム−１：４ （ｖ／ｖ） ）
メチレン） 、 １７４０ （カルボン酸）１６４０及
び１５５０ （アミド）
試験例１
試験動物：
５週令のｓｌｃ：ｄｄｙ雄性マウスを用いた。Melting point 211-215°C (decomposition) [α) +5.2 (G O,5, dichloromethane:lyloloform-1:4 (v/v)) methylene), 1740 (carboxylic acid) 1640 and 1550 (amide) Test example 1 Test animals: 5-week old slc:ddy male mice were used.
試験菌：
Ｅ、ｃｏｌｉ Ｅ ７７１５６を用いた。末菌を試験動
物の皮下に投与したところ、その最小致死量は約６×１
０’（：Ｆｔｌ／ｍｏｕｓｅであ）た。Test bacteria: E. coli E 77156 was used. When the terminal bacteria were subcutaneously administered to test animals, the minimum lethal dose was approximately 6 x 1
0' (:Ftl/mouse).
検体：
試験化合物をダルベツコのリン酸緩衝化生理食塩水（ｐ
Ｈ７，４，日水製薬株式会社製、以下ＰＢＳと称す）に
溶解し、５００μｇ／ｍｌの濃度に調整した。Sample: Test compound was added to Dulbecco's phosphate buffered saline (p
H7.4, manufactured by Nissui Pharmaceutical Co., Ltd., hereinafter referred to as PBS), and adjusted to a concentration of 500 μg/ml.
試験方法：
マウスに１匹あたり １００μｇの検体を皮下投与し、
その２４時間後に試験菌を５．８６Ｘ １０’ＣＦＵ／
匹の接種量で皮下に接種した。接種後、 ７日間毎日試
験動物のうち、生存しているものの匹敵をカウントした
。結果を表１に示した。尚、対照群には検体の代りにＰ
ＢＳを同量（０，２ｍ１）投与した。Test method: 100 μg of the specimen per mouse was subcutaneously administered,
24 hours later, test bacteria were added at 5.86X 10'CFU/
The inoculum was subcutaneously administered in an amount equivalent to one animal. After inoculation, the number of surviving test animals was counted daily for 7 days. The results are shown in Table 1. In addition, for the control group, P was used instead of the specimen.
The same amount (0.2 ml) of BS was administered.
表１
傘Ｐ＜０．０１ ＶＳ対照群（ｃｈｉ−ｓｑｕａｒｅ
ｔｅｓｔ ）比較化合物：Ｎ−（Ｎ−アセチルムラミル
−Ｌ−アラニル−Ｄ−イソグルタミニル）−Ｎ−ステア
ロイル−Ｌ−リジン
上表から明らかなように９本発明化合物は優れた感染防
御効果が確証されている比較化合物に優るとも劣らない
感染防御効果を示した。Table 1 Umbrella P<0.01 VS control group (chi-square
test) Comparative compound: N-(N-acetylmuramyl-L-alanyl-D-isoglutaminyl)-N-stearoyl-L-lysine As is clear from the above table, the 9 compounds of the present invention have been confirmed to have an excellent infection-preventing effect. The anti-infection effect was as good as that of the comparative compound.
試験例２
日本薬局方の発熱性物質試験法に従い、実施例の化合物
及び比較化合物について発熱性の有無を、検討した。結
果を表２に示した。Test Example 2 The presence or absence of pyrogenicity was investigated for the compounds of the examples and comparative compounds according to the pyrogenic substance test method of the Japanese Pharmacopoeia. The results are shown in Table 2.
表２
＋２発熱性あり、−：発熱性なし
上表から明らかなように１本発明化合物は比較化合物に
比べ発熱性において優れていた。Table 2 +2 Exothermic, -: No exothermic As is clear from the above table, the compound of the present invention was superior to the comparative compound in terms of exothermic.
Claims (1)
−アラニン、Ｌ−セリン及びＬ−バリンより選ばれるア
ミノ酸残基を、ｎは１〜６の整数を、Ａは炭素数１０〜
２５のアルキル基を意味する〕で示される化合物及びそ
の塩[Claims] Formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, Acy1 is an acyl group having 2 to 6 carbon atoms, and X is L
- An amino acid residue selected from alanine, L-serine, and L-valine, n is an integer of 1 to 6, and A is a carbon number of 10 to
25 alkyl group] and salts thereof
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63243522A JP2643365B2 (en) | 1988-09-28 | 1988-09-28 | 1-deoxymuramyl peptide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63243522A JP2643365B2 (en) | 1988-09-28 | 1988-09-28 | 1-deoxymuramyl peptide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0291099A true JPH0291099A (en) | 1990-03-30 |
| JP2643365B2 JP2643365B2 (en) | 1997-08-20 |
Family
ID=17105159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63243522A Expired - Fee Related JP2643365B2 (en) | 1988-09-28 | 1988-09-28 | 1-deoxymuramyl peptide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2643365B2 (en) |
-
1988
- 1988-09-28 JP JP63243522A patent/JP2643365B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2643365B2 (en) | 1997-08-20 |
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