JPS58206517A - Preventive and remedy for disease caused by immunoinsufficiency - Google Patents

Preventive and remedy for disease caused by immunoinsufficiency

Info

Publication number
JPS58206517A
JPS58206517A JP57089806A JP8980682A JPS58206517A JP S58206517 A JPS58206517 A JP S58206517A JP 57089806 A JP57089806 A JP 57089806A JP 8980682 A JP8980682 A JP 8980682A JP S58206517 A JPS58206517 A JP S58206517A
Authority
JP
Japan
Prior art keywords
compound
formula
preventive
background background
animals
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
Application number
JP57089806A
Other languages
Japanese (ja)
Other versions
JPH026326B2 (en
Inventor
Masakazu Yamamoto
雅一 山本
Seiichi Araki
誠一 荒木
Hiroshi Yamamoto
博 山本
Isao Yamatsu
功 山津
Takeshi Suzuki
鈴木　赳
Shoji Kajiwara
彰治 梶原
Yoshikazu Suzuki
芳和 鈴木
Masae Arai
新井　昌栄
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eisai Co Ltd
Original Assignee
Eisai Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eisai Co Ltd filed Critical Eisai Co Ltd
Priority to JP57089806A priority Critical patent/JPS58206517A/en
Priority to DE3348493A priority patent/DE3348493C2/en
Priority to GB08314419A priority patent/GB2122610B/en
Priority to DE3348492A priority patent/DE3348492C2/en
Priority to DE3318989A priority patent/DE3318989C2/en
Priority to DE3348500A priority patent/DE3348500C2/en
Priority to BE2/60109A priority patent/BE896865A/en
Priority to SE8303013A priority patent/SE461650B/en
Priority to ES522789A priority patent/ES522789A0/en
Priority to NL8301892A priority patent/NL194300C/en
Priority to CA000429108A priority patent/CA1310660C/en
Priority to CH2902/83A priority patent/CH654823A5/en
Priority to DK239483A priority patent/DK171640B1/en
Priority to FR838308941A priority patent/FR2527597B1/en
Priority to IT21364/83A priority patent/IT1164256B/en
Priority to AT0197283A priority patent/AT389871B/en
Priority to FR8317169A priority patent/FR2532843A1/en
Priority to FR8317171A priority patent/FR2532844B1/en
Priority to FR8317176A priority patent/FR2532847B1/en
Priority to FR8317170A priority patent/FR2532848B1/en
Priority to FR8317175A priority patent/FR2532846B1/en
Priority to FR8317173A priority patent/FR2532845B1/en
Publication of JPS58206517A publication Critical patent/JPS58206517A/en
Priority to ES529754A priority patent/ES8507444A1/en
Priority to ES529753A priority patent/ES8506567A1/en
Priority to GB08508219A priority patent/GB2159712B/en
Priority to GB08508214A priority patent/GB2159054B/en
Priority to GB08508217A priority patent/GB2159710B/en
Priority to GB08508215A priority patent/GB2159709B/en
Priority to GB08508216A priority patent/GB2159055B/en
Priority to GB08508220A priority patent/GB2159713A/en
Priority to GB08508218A priority patent/GB2159711B/en
Priority to US06/760,221 priority patent/US4624966A/en
Priority to FR858513026A priority patent/FR2569108B1/en
Priority to SE8801513A priority patent/SE502922C2/en
Priority to SE8801514A priority patent/SE502923C2/en
Priority to SE8801515A priority patent/SE502924C2/en
Publication of JPH026326B2 publication Critical patent/JPH026326B2/ja
Priority to US08/011,197 priority patent/US5280048A/en
Priority to US08/584,145 priority patent/US6111131A/en
Priority to US08/601,489 priority patent/US6288128B1/en
Priority to US08/599,944 priority patent/US5658958A/en
Priority to NL9900009A priority patent/NL9900009A/en
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters

Abstract

PURPOSE:To provide a preventive and remedy for the diseases caused by the immunoinsufficiency of man and animal, especially effective to increase the resistance to the infectious diseases of man and animal, and having low toxicity and high stability, by using a polyprenyl alcohol compound as an active component. CONSTITUTION:The polyprenyl alcohol compound of formula I (a and b are H or together form a bond; n is integer of 1-10) is used as an active component. A concrete example of the compound of formula is 3,7,11,15,19,23,27,31-octamethyl- 2,6,10,14,18,22,26,30-dotriacontaoctaen-1-ol. It can be prepared via several steps using the compound of formula II and a cyanoacetic acid lower alkyl ester as starting raw materials. It can be administered in the form of e.g. granules, powder, etc., and can be prepared by a conventional process using a conventional carrier.

Description

【発明の詳細な説明】 本発明は、ヒトまたは動物の免疫機能不全による疾患の
予防・治療剤、符にヒトまたは動物の感染症に対する防
禦剤に関する。更に詳しく述べれば。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a preventive/therapeutic agent for diseases caused by immune dysfunction in humans or animals, and in particular to an agent for preventing infectious diseases in humans or animals. Let me explain in more detail.

般式 （式中ａ、ｂは水素原子またはａ−ｂで結合手を形成す
る。ｎは１−１０の整数を示す。）で表わされるポリプ
レニルアルコール系化合物を有効成分とするヒトまたは
動物の免疫機能不全による疾患の予防・治療剤、特にヒ
トまたは動物の感染症に対する防禦剤に関する。A polyprenyl alcohol compound represented by the general formula (where a and b are hydrogen atoms or a-b form a bond; n is an integer from 1 to 10) as an active ingredient for humans or animals. The present invention relates to preventive and therapeutic agents for diseases caused by immune dysfunction, particularly to preventive agents against infectious diseases in humans and animals.

近年、免疫学の進ルが急速であり、４４々の疾患が免疫
機能不全に起因しているものと考えられ“Ｃきている。In recent years, advances in immunology have been rapid, and 44 diseases are thought to be caused by immune dysfunction.

例えば、癌、細菌感染症、喘息、関節リウマナ、自己免
疫疾患などが免疫ａＩ＆能不全不全因している疾患とし
てあげられている。For example, cancer, bacterial infections, asthma, rheumatoid arthritis, autoimmune diseases, and the like are listed as diseases that are caused by immune aI and insufficiency.

細菌感染症は、単に病原菌の浸入のみによる単純性感染
症に加えて、各種重篤な基礎疾患を伴う複雑性感染症の
増加が深刻な問題となってきている。例えば癌に伴う感
染症は臨床上履もわずられしい問題である。癌を担うこ
とによって、全身性。BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND BACKGROUND OF THE INVENTION Bacterial infections are becoming a serious problem due to an increase in complex infections accompanied by various serious underlying diseases, in addition to simple infections caused solely by infiltration of pathogenic bacteria. For example, infectious diseases associated with cancer are a serious clinical problem. Systemic by bearing cancer.

局所的な抵抗力紙Ｆを招き、易感染状態丁で感染症を合
併、続発する。癌に伴う感染は、初期においては呼吸器
感染、尿路感染、胎道感染、皮膚感染が多く、末期にお
いては１１ｍ１＆、敗血症が多い。This leads to localized resistance to infection, leading to complications and subsequent infections in patients who are susceptible to infection. Infections associated with cancer often include respiratory tract infection, urinary tract infection, fetal canal infection, and skin infection in the early stages, and 11m1 & sepsis are common in the late stages.

この腫瘍に伴う感染症併発の機序については９次のよう
な過程が一般的である。The following 9 general mechanisms are involved in the complications of infection associated with this tumor.

すなわち、白血病、悪性り・〈バ腫、癌の進展に伴い、
正常な組織、細胞の障害、特にリンパ系細胞や、Ｔｈ粒
球細胞ａｌ＆能の低下をきたｌので、易感染性となり、
感染症を併発すると考えられている。In other words, with the progress of leukemia, malignant tumors, and cancer,
Normal tissues and cells are damaged, especially lymphoid cells and Th granulocytic cells are impaired, resulting in increased susceptibility to infection.
It is thought to be associated with infectious diseases.

このような場合、抗生剤投与による根治効果が乏しく９
反虚感染、菌交代症、難治感染にいたることが６い。し
たかつて、従来の抗生剤、化学療法剤のみでは根治がほ
とんど期待できず、生体防禦機能の改善なくしＣは治療
不６Ｉ能であり、生体の防Ｓａ能を高める薬剤の開発が
望まれている。In such cases, antibiotic administration has little curative effect9.
It can lead to anti-deficient infection, bacterial replacement disease, and intractable infection. In the past, conventional antibiotics and chemotherapeutic agents alone could hardly be expected to cure the disease, and C could not be treated without improvement of the body's defense function, so the development of drugs that enhance the body's ability to resist Sa is desired. .

−ｈ、家畜・家禽などの動物の細ｓｉ！Ｉｉ＆染に対し
−Ｃは、抗性物質がその中心的存在となっており。- h, detailed description of animals such as livestock and poultry! In contrast to Ii & dyeing, -C has an anti-inflammatory substance at its core.

事実、各種の抗生物質の登場によって病原細菌による龜
篤な感染症は減少している。しかし、畜産界では抗−剤
の乱用から、畜水産物中の残留・耐性閑の増加１ｍ交代
症などを引き起こし１社会問題とな、っている。すなわ
ち、宿主は感染防禦能が着しく低下し、感染症に対する
修復機能も障害されているため、細菌感染症は直りに（
（再感染し絽い状態を作っている。更に、自発性感染症
（日和見感染症）が家畜の生産性を低下させ、その損失
は大きい。そこで宿主の免疫能の活性を高め。In fact, with the advent of various antibiotics, serious infections caused by pathogenic bacteria are decreasing. However, in the livestock industry, overuse of antibiotics has caused residues in livestock and aquatic products, increased resistance, and 1m alternation disease, which has become a social problem. In other words, the host's ability to defend against infection has steadily declined, and its repair function against infections is also impaired, so bacterial infections are quickly overcome (
(Re-infection creates a serious situation.Furthermore, spontaneous infections (opportunistic infections) reduce the productivity of livestock, resulting in large losses.Therefore, the host's immune system is activated.

生体の防禦機能を高める必要がある。It is necessary to enhance the defense function of the living body.

本発明者等は、上述の実情に鑑み、免疫機能を正常化し
、生体の防ｌｌ１４機能を高める薬剤について。In view of the above-mentioned circumstances, the present inventors have developed a drug that normalizes the immune function and enhances the immune system's defense function.

長年鋭意研究してきたが、意外にも次の一般式（式中ａ
、ｂは水素原子またはａ−ｂで結ｕトを形成する。１１
は１〜１０の整数を示す。）で表わされるポリプレニル
アルコールがヒトおよび動物や免疫機能不全による疾患
の予防・治療剤、特にヒトおよび動物の感染症に対する
防禦剤として自効であることを見い出し９本発明を完成
したものである。゛ すなわち９本発明化合物は、ヒトおよび動物の免疫機能
を正常化し感染抵抗性を高める作用を有するので、ヒト
および動物の免疫機能不全による疾患の予防・治療剤、
各種感染底に対する防禦剤として有用である。After many years of intensive research, I unexpectedly found the following general formula (in the formula a
, b form a hydrogen atom or a-b bond. 11
represents an integer from 1 to 10. The present invention has been completed after discovering that polyprenyl alcohol represented by () is self-effective as a prophylactic and therapeutic agent for diseases caused by immune dysfunction in humans and animals, and in particular as a preventive agent against infectious diseases in humans and animals.9 . In other words, the compound of the present invention has the effect of normalizing the immune function of humans and animals and increasing resistance to infection, so it can be used as a preventive/therapeutic agent for diseases caused by immune dysfunction in humans and animals,
It is useful as a repellent against various types of infections.

ヒトの場合の具体例をあげれば、関節リウマチ。A specific example in humans is rheumatoid arthritis.

自己免疫疾患、癌、喘息、および例えば敗血症。autoimmune diseases, cancer, asthma, and sepsis for example.

肺炎、髄膜炎、芥偵ウィルス感染症などの品種感染症な
どに月−効である。It is effective against various infectious diseases such as pneumonia, meningitis, and staghorn virus infection.

また動物の場合の具体例をあげれば９例えば豚のト°虜
、Ｍｌ炎（８１弓Ｐ、Ａル、ヘモフィルス、パスツレラ
）、Ｔ（ｊＷ、Ｍの肺炎（マイクロプラズマ、ヘモフィ
ルス）、マレック病、　牛（７）下ｆＭ、　肺炎、乳房
炎などに有効である。In addition, specific examples in the case of animals include 9 cases of pig poisoning, Mlitis (81 Arch P, Al, Haemophilus, Pasteurella), T (jW, M pneumonia (Microplasma, Haemophilus), Marek's disease, Effective for cow (7) lower fM, pneumonia, mastitis, etc.

また、ヒトおよび動物の感染症に本発明化合物を投与す
る場合、抗生物質との併用により著しくその治療効果を
高める。このことは、前述した畜産業界で問題となって
いる抗生物質の乱用という問題をも解決するものであり
重要な意義がある。Furthermore, when the compounds of the present invention are administered to treat infectious diseases in humans and animals, their therapeutic effects are significantly enhanced when used in combination with antibiotics. This is of great significance because it also solves the aforementioned problem of overuse of antibiotics in the livestock industry.

史に、家畜・家禽などの動物の場合を例にとれば、生体
の感染抵抗性を高めるので、初生時のベース薬として有
用であること、多頭側飼育、輸送などに起因するストレ
スの緩和に有用であること。Historically, in the case of animals such as livestock and poultry, it has been shown that it increases the organism's resistance to infection, making it useful as a base drug at the beginning of life, and that it is useful for alleviating stress caused by multi-head rearing and transportation. Be useful.

およびワクチン効果の増強に有用である。and useful for enhancing vaccine efficacy.

したがって１本発明の目的は、ヒトおよび動物の免疫機
能不全の新規な予防・治療剤を提供するにある。Therefore, an object of the present invention is to provide a novel preventive/therapeutic agent for immune dysfunction in humans and animals.

史に９本発明の目的は、ヒトおよび動物の感染症に対す
る新規な防禦剤を提供するにある。History 9 An object of the present invention is to provide a novel preventive agent against infectious diseases in humans and animals.

本発明におけるポリプレニルアルコールの代表的化合物
を以ドに掲げるが１本発明がこれらのものに限定される
ことがないことはいうまでもない。Representative compounds of polyprenyl alcohol in the present invention are listed below, but it goes without saying that the present invention is not limited to these compounds.

＋−Ｊ　　３．　７．１１．１５．１９．２３．２７．
３１−オクタメチル−２，６，１０，１４，１８，２２
，２６，，３０−ドトリアコンタオクタエン−１−オー
ル ｎ　　　　３．　　７．　１１．　　１５．　　１９．
　２３＋　　２７．　３１．　３５−　ノ　ノ。+-J 3. 7.11.15.19.23.27.
31-octamethyl-2,6,10,14,18,22
,26,,30-dotriacontaoctaen-1-ol n 3. 7. 11. 15. 19.
23+ 27. 31. 35- No No.

メチル−２，６，１０，１４，１８，２２，２６，３０
，：Ｊ４−ヘキサトリコンタノナエン−１−ｔ−ルイ’
＋　　　　３＋　　　７．　　ＩＬ　　＋５．　　　ｌ
’）、　　２３＋　　２７＋　　３Ｌ　　３５＋　　：
二１；９−デカメチル−２，６＋　ｌ（Ｌ　１４．１８
．２２＋　２６．３ＣＬ調、３８−テトラコンタデカエ
ン−１−オール（、）　　３．　７．１１．１５．　　
＋９．２３．２７．３１．３５．３９゜４３−ウンデカ
メチル−２，６，１０，１４，１８，２２゜あ、　３０
．３４．３８．４２−テトラテトラコンタウ７・デカエ
ン−１−オール １：）　　３．　７．１１．１５．１９．２３．２７−
へブタメチル−２，６，１０，＋１．１８．　、！２．
２６−オクタコナへブタエン−１−オール ０　３、　７．　Ｉｌｉ　１５．１９．２３−ヘ＋−ｋ
ｊｌｆルー２．　６．１０゜１４、　＋８．２２．−−
テトラコサへキサエンー１−オール ’）　　’３＋　　Ｌ　ＩＬ　１５＋　１９−ペンタメ
チル−２，６゜１０、１４．　＋８−エイコナベンタエ
ンー１−オールｏ　　３．　７＋　１１．１５−テトラ
メチル−２，６，１０゜１４−ヘキサデカテトラエン−
１−オーポリ　３，７．１１−）ジメチル−２，６，１
０−ドデカトリエン−１−オール ＋）３．７−シメチルー２．６−オクタシエンー１−オ
ール ｆ、　　３．　７．１１．１５．　１９．２３．２７．
３１．３５−ノナメチル−６、１０，１４，１８，２２
，２６，３０，３４−ヘキサトリコンタオクタエン−１
−オール（）　　　　３．　　７．　　１１．　　１５
．　　１９．　　２３．　　２７．　　３１．　　３５
．　　３９−ｒ°カメチル−６、１０，１４，１８，２
２，２６，３０，３４゜あ−テトラコンタノナエンー１
−オールＬＪ　　３．　７．１Ｌ　Ｌ５．１５１Ｌ　２
３．２′７．３１．３５．３９゜招−ウンデカメチル−
６，１０，１４，１８，２２，２６゜３０、３４．３８
．４２−テトラテトラコンタデカエン−１−オール （’、＋　　３．　７．１１．１５．１９−ペンタメチ
ル−６，１０゜１４、１８−エイコサテトラエン−１−
オールＯ３，７，１１，１５−テトラメチル−６、ｔｏ
、　１４−へキサデカトリエン−１−オール Ｏ３，７，１１−トリメチル−６，１０−ドデカジエン
−１−オール ０３．７−シメチルー６−オクタエンー１−オール Ｌ）　　３．　７．１１．　ｌ！５．１９．　Ｚ３−へ
士号メチル−６゜１０、１４．１８．２２−テトラコサ
ペンタエン−１−オール ０　３＋　　７．１１．１５．１９．２３．２７−へブ
タメチル−６、１０，１４，１８，２２，２６−オクタ
コサへキサエン−１−オール １）３．　７１　Ｉｌｌ　１５．　＋９１２３１２７１
３１−才クタメチル−６，１０，１４，１８，２２，２
６，３０−ドトリｒコンタヘプタエンー１−オール 本発明化合物は、神々のｈ′法で製造されつるが。Methyl-2,6,10,14,18,22,26,30
, :J4-hexatricontanonaene-1-t-Loui'
+ 3+ 7. IL +5. l
'), 23+ 27+ 3L 35+:
21;9-decamethyl-2,6+ l (L 14.18
．． 22+ 26.3CL tone, 38-tetracontadecaen-1-ol (,) 3. 7.11.15.
+9.23.27.31.35.39゜43-Undecamethyl-2,6,10,14,18,22゜A, 30
．． 34.38.42-Tetratetracontau7-decaen-1-ol 1:) 3. 7.11.15.19.23.27-
Hebutamethyl-2,6,10,+1.18. ,! 2.
26-octaconabutaen-1-ol 0 3, 7. Ili 15.19.23-he+-k
jlf roux 2. 6.10°14, +8.22. ---
Tetracosahexaen-1-ol') '3+ L IL 15+ 19-pentamethyl-2,6°10, 14. +8-eiconabentaen-1-ol o 3. 7+ 11.15-tetramethyl-2,6,10゜14-hexadecatetraene-
1-Opoly 3,7.11-)dimethyl-2,6,1
0-dodecatrien-1-ol+)3.7-dimethyl-2.6-octacyen-1-ol f, 3. 7.11.15. 19.23.27.
31.35-nonamethyl-6,10,14,18,22
,26,30,34-hexatriconetaoctaene-1
-all() 3. 7. 11. 15
．． 19. 23. 27. 31. 35
．． 39-r°camethyl-6,10,14,18,2
2,26,30,34゜A-Tetracontanonaene-1
-All LJ 3. 7.1L L5.151L 2
3.2'7.31.35.39゜Undecamethyl-
6,10,14,18,22,26°30,34.38
．． 42-tetratetracontadecaen-1-ol (', + 3.7.11.15.19-pentamethyl-6,10°14,18-eicosatetraen-1-
AllO3,7,11,15-tetramethyl-6,to
, 14-hexadecatrien-1-ol O3,7,11-trimethyl-6,10-dodecadien-1-ol 03.7-dimethyl-6-octaen-1-ol L) 3. 7.11. l! 5.19. Z3-to BS methyl-6゜10, 14.18.22-tetracosapentaen-1-ol 0 3+ 7.11.15.19.23.27-hebutamethyl-6, 10,14,18, 22,26-octacosahexaen-1-ol 1)3. 71 Ill 15. +91231271
31-year-old Kutamethyl-6,10,14,18,22,2
6,30-dotri-r-contaheptaen-1-ol The compound of the present invention is produced by the divine H' method.

一般式（Ｉ）においてａ、ｂがａ−ｂで結合トを形成し
ている場合は２例えば、　　１３ｕｒｒｅｌｌ　ｅｔ　
ａｌ、。In general formula (I), when a and b form a bond with a-b, 2 For example, 13urrel et
al.

Ｊ、　ｅｈｅｍ、　Ｓｕｃ、　　（Ｃ）　１９６６、２
１４４　　に記載された方法、　　Ｐｏｐ３ａｋ　ｅｔ
　ａｌ、、　Ｊ、　Ｈｉｏｌ、　Ｃｈｅｍ、　２３７゜
ｂｂ（１９６２）　　記載さ（した方法、けｌ５ｌｅｒ
　ｅｔ　ａｌ、。J, ehem, Suc, (C) 1966, 2
144, Pop3ak et al.
al., J. Hiol, Chem, 237°bb (1962)
et al.

１ｊｅｌｖ、　ｅｈｉｍ　Ａｃｔａ、　４２．２６１６
　（１９５９）　　に記載された方法、特開昭５３−３
１６１０に記載された方法または特開昭５４−５５５０
６に記載された方法により製造することが可能である。1jelv, ehim Acta, 42.2616
(1959), JP-A-53-3
1610 or JP-A-54-5550
It can be manufactured by the method described in 6.

またａ、ｂが水素原子である場合は２例えば特開昭５５
−７６８２９に記載された方法により製造することが一
１能である。この方法を具体的に述べれば以ドのとおり
である。In addition, when a and b are hydrogen atoms, 2, for example, JP-A-55
-76829. This method will be specifically described as follows.

イ）次の一般式 （式中ｎはｌ　−１０の整数を表わす）の化合物とシア
ノ酢酸低級アルキルエステルヲ塩基の存在ｔ′に反応さ
せて一般式 ％式％（［） （式中ｎはｌ１ｉＪ記の意味を有し、ｌＬは低級γル＋
ル基を示す） で表わされる化合物を得２次に。b) A compound of the following general formula (in which n represents an integer of 1 - 10) and a lower alkyl cyanoacetic acid ester are reacted with the presence of a base t', and the compound of the general formula % formula % ([) (in the formula n is It has the meaning of l1iJ, and lL is lower γL +
Second, a compound represented by (representing a group) is obtained.

ｕ＞　上記の−・般弐目ｌで表わされる化合物を例えば
水素化ホウ素ナトリウムなどの還元剤を用いて還元して
一般式 （） （式中ｎおよびルは前記の意味を有する。）で表わされ
る化合物を得１次いで ハ）上記の一般式（ＩＶ）で表わされる化合物を。u> The above-mentioned compound represented by - and general 2 is reduced using a reducing agent such as sodium borohydride to obtain a compound represented by the general formula () (in which n and l have the above-mentioned meanings). 1) Then c) a compound represented by the above general formula (IV).

例えば水酸化カリウムなどの強アルカリの存在ドに脱炭
酸Ｌ７て次の一般式 （） （ｎは前記の轍味を（ｒする） で表わされる化合物を得２次いで 二）上記の−・般式〔ｖ〕で表わされる化合物を例えば
水酸化カリウムなどの強アルカリの存在下に加水分解し
て次の一般式 ％式％（ ［） で表わされる化合物を得１次いで ホ）上記の一般式（ＶＩ）で表わされる化合物を例えば
ヴイトライト、リチウムアルミニウムハイドライドなど
の還元剤により還元して 目的物質（Ｉ） 」ト（Ｃ口２　　Ｃ＝ＣＨ−Ｃｌ、−テ１（ｌ（、−Ｃ
Ｉ−ＣＩ、−Ｃ）１．ＯＨ（式中ｎｌ！前記の意味を有
する） を得ることができる。For example, by decarboxylating L7 in the presence of a strong alkali such as potassium hydroxide, a compound represented by the following general formula () (n represents the above-mentioned rut (r)) is obtained. The compound represented by [v] is hydrolyzed in the presence of a strong alkali such as potassium hydroxide to obtain a compound represented by the following general formula ([)]. ) is reduced with a reducing agent such as Veithrite or lithium aluminum hydride to obtain the target substance (I).
I-CI, -C)1. OH (in the formula nl! has the meaning given above) can be obtained.

次に本発明化合物の効果を実験例にて詳述する。Next, the effects of the compounds of the present invention will be explained in detail using experimental examples.

実験例 ｔｉｔ　　実験方法 ｓｌｃ　：　ＩＣ１も雄性マウス（６〜７週令９体重ａ
〜３０））に、Ｆ記に記載した被験化合物を次表（表１
）に示す址筋内内投与し、２４時間後に臨床由来の大腸
菌（Ｅｓｃｈｅｒｉｃｂｉａ　Ｃｏ１１　）を２．　ｓ
　Ｘｔｏ’マウスを皮Ｆ接梱し、感染後７日ｌ］の生存
数から生残率を求めた。Experimental example tit Experimental method slc: IC1 was also a male mouse (6-7 weeks old, 9 weight a
~30)), the test compounds described in Section F are listed in the following table (Table 1
24 hours later, clinically derived Escherichia coli (Eschericbia Co11) was administered intramuscularly. s
Xto' mice were skin-packed and the survival rate was determined from the number of survivors 7 days after infection.

３．７．１１−トリメチル−６，１０−ドデカジエン−
１−オール 化合物Ｂ： ３、　７．１１．１５−テトラメチルー２１６゜ｔｏ、
　１４−へ牛すＴ゛カデトラエン＝１オール化合物Ｃ： コｉ、　　７．１１．１５−テトラメチル−６，１０゜
１４−一−＼キサデカトリエンー１−オール化８物υ： ３、　７．１１．１５．１９−ペンタメチル−６゜１０
、１４．１８−エイコサテトラエン−１−オール 化合物Ｅ： 化合物）： ３．７−シメチルー２，６−オクタジニンー１−オール 化合物（ｉ： ａ、　７．１１．１５；　１９．２３．２７．３１．３
５．３９−デカメチル−２，６＋　ｌ（Ｌ　１４．１８
．２２．２６゜３０、３４．３８−テトラコンタデカエ
ン−１−オール 化合物Ｉ（： ３、７．１１．１５．１９．２３．２７．　：３１．３
５．３９゜お−ウンデカメチル−６、１０，１４，１８
，２２゜あ、　３０．３４．３８．．１２−テトラテト
ラコンタデカエン−１−オール 化合物■： ３、　７．１１．１５．１９．晶−−キサメチル−６、
１０，１４，１８，２２−テトラコサペン・クエン−１
−オール 化合物Ｊ： ３、７．１１．１５．１９．２３．２７−へブタメチル
−６、１０，１４，１８，２２，２６−オクタコサへキ
サエン−１−オール ３、　７．１１．１５．１９．２３．２７．３１−オク
タ）　ｆｋ−６８ｉｏ、　１４１１８．２２．２６．３
０−　）’　）リアコンタへブタエン−１−オール χ・１照化合物：　ＭＤ　Ｐ　（ｋＭｕｒ−Ｌ−Ａｌａ
　−Ｄ　−Ｑｌｕ） （３）実験結果 結果を表１に示す。3.7.11-trimethyl-6,10-dodecadiene-
1-ol compound B: 3, 7.11.15-tetramethyl-216°to,
14-hexadetraene-1-ol Compound C: Coi, 7.11.15-tetramethyl-6,10゜14-1-\xadecatrien-1-ol compound υ: 3, 7 .11.15.19-pentamethyl-6゜10
, 14.18-eicosatetraen-1-ol Compound E: Compound): 3.7-dimethyl-2,6-octazinin-1-ol compound (i: a, 7.11.15; 19.23.27. 31.3
5.39-decamethyl-2,6+ l (L 14.18
．． 22.26°30, 34.38-Tetracontadecaen-1-ol Compound I (: 3, 7.11.15.19.23.27.: 31.3
5.39゜O-undecamethyl-6, 10, 14, 18
,22゜ah, 30.34.38. ．． 12-tetratetracontadecaen-1-ol compound ■: 3, 7.11.15.19. Crystal--xamethyl-6,
10,14,18,22-tetracosapene-1
-ol Compound J: 3,7.11.15.19.23.27-hebutamethyl-6,10,14,18,22,26-octacosahexaen-1-ol 3,7.11.15.19 .23.27.31-octa) fk-68io, 14118.22.26.3
0-)') rearcontahebutaen-1-ol χ・1 Reference compound: MD P (kMur-L-Ala
-D-Qlu) (3) Experimental results The results are shown in Table 1.

表　　１ ２、　マクμノアージの貧食能の増大効果（１）実験り
法および結果 ｓｌｃ　：　ＩＣル系雄性マウス（８適合１体重２２〜
３ＯＮ）に、藪記した被験化合物を１００〜／ｋｇ筋内
内投与し、２４時間後にカーボンもクリアランステスト
をおこない、マクロファージの貧食能を測定した。なお
り−ボン・クリアランステストは。Table 1 2. Increasing effect of Macμ Noage on poor eating ability (1) Experimental method and results slc: IC Le strain male mice (8 fits 1 body weight 22~
3ON), 100~/kg of the indicated test compound was intramuscularly administered, and 24 hours later, a carbon clearance test was also performed to measure the phagocytic ability of macrophages. Naori-bon clearance test.

（ｊ、　＃３１（ＪＺＺＩ、　Ｂ、　Ｂｔ；ＮＡｃｇｒ
ｔルＡＦＡＮＩ）　　Ｂ。(j, #31 (JZZI, B, Bt; NAcgr
tLE AFANI) B.

Ｎ、　　ＩＩＡＬＰＭＲＮ、　　Ｂｒ１ｔ、Ｊ、ｅｘｐ
、Ｐａｔｈ、、　　３４゜４４１−４５７に記載されて
いる方法に準じておこな−〕だ、。N, IIALPMRN, Br1t, J, exp.
, Path, 34° 441-457.

その結果を表２に示す。The results are shown in Table 2.

表２において、貧食能の変化（％）の数値は、コノトロ
ールの半減時間を１００とし、これに対して変化した割
合を示す。In Table 2, the numerical value of change (%) in poor eating ability indicates the percentage change with respect to the half-life time of Conotrol, which is set as 100.

表　　２ 表２において、貧食能力が高まっている場合は。Table 2 In Table 2, if the ability to eat poorly is increasing.

半減時間が減少するが、２０Ｃ％）以り、すなわちその
数値が（資）より少い場合は強い貧食能の促進を示す。Although the half-life time decreases, if the value is less than (20C%), that is, if the value is less than (20C%), it indicates strong promotion of poor eating ability.

したがって１本発明化合物のうち、化合物Ａ、Ｄ、ｇ、
Ｉ、Ｊ、には非常に強い貧食能の促進効果があることが
明らかである。Therefore, among the compounds of the present invention, compounds A, D, g,
It is clear that I and J have a very strong effect of promoting poor eating ability.

Ｌ記の実験例により８本発明化合物は免疫４１ｉ能を正
常化し、感染抵抗性を高めることが明らかとなった。The experimental example described in Section L revealed that the compound of the present invention (8) normalizes immune 41i ability and increases resistance to infection.

本発明化合物は、極めて毒性の低いものであり、安全性
は非常に高いものであり、したがって長期連用投与がＩ
Ｉ能であり、この意味でも本発明の価値は高い。The compound of the present invention has extremely low toxicity and is very safe, so long-term continuous administration is possible.
In this sense, the value of the present invention is high.

すなわち、８Ｄ系ラツト（体重的２００　ｆ／）に前記
（Ｄ　化合物（化合物に−Ｋ）を５００”Ｖ／に９を経
１１投与したが、死亡例、副作用は何ら観察されなかっ
た。That is, the above-mentioned (D compound (-K in the compound)) was administered to 8D rats (body weight 200 f/) at 500''V/9 for 11 days, but no deaths or side effects were observed.

本発明化合物をヒトの免疫機能不全による疾患のｔ防・
治療剤あるいはヒトの感染症に対する防鋼剤として患者
に投与する際の投与量は、疾患の楕類、症状の程度、化
合物の種類などにより大きく異なり特に限定されないが
、成人１日あたり約１０〜・〜４，０００〜．好ましく
は５０ｗ１〜５００ηを経口若しくは非経［」的に投与
する。感染症に対する防禦剤として投与する場合、抗生
物質との併用はもちろんさしつかえない。投与剤型とし
ては２例えば散剤。The compounds of the present invention can be used to prevent diseases caused by immune dysfunction in humans.
The dosage when administered to patients as a therapeutic agent or a protective agent against human infectious diseases varies greatly depending on the type of disease, severity of symptoms, type of compound, etc., but is not particularly limited, but is approximately 10 to 100 mg per day for adults.・~4,000~. Preferably, 50w1 to 500η is administered orally or parenterally. When administered as a preventive agent against infectious diseases, it is of course possible to use it in combination with antibiotics. The dosage form is 2, for example, a powder.

細粒剤、顆粒剤２錠剤、カプセル剤、注射剤などがあげ
られる。製剤化の際は２通常の製剤担体を用い、常法に
より製造する。Examples include fine granules, granules (two tablets), capsules, and injections. When preparing a formulation, it is produced by a conventional method using a conventional pharmaceutical carrier.

すなわち、経１１用固形製剤を調製する場合はＩＥ薬に
賦形剤、史に必要に応じて結合剤、崩壊剤。That is, when preparing a solid preparation for oral administration, excipients are added to the IE drug, and binders and disintegrants are added as necessary.

滑沢剤１着色剤、矯味矯臭剤などを（＋１１えた恢、常
法により錠剤、彼ｍＷ剤、顆粒剤２敗削、カプセル削な
どとする。Add lubricant 1, coloring agent, flavoring agent, etc. (+11) and form into tablets, powder, granules, capsules, etc. using the usual method.

賦形薬としては２例えば乳糖、フーンスター・ｔ。Examples of excipients include lactose, Foonstar T.

白糖、ブドウ糖、ソルビット、結晶セルロースなどが、
結合剤としては例え１１．ポリビニルアルコール、ポリ
ビニールエーテル、エチルセルローんメチルセルロース
、′ｒラビアゴム、トラガント。White sugar, glucose, sorbitol, crystalline cellulose, etc.
Examples of binders include 11. Polyvinyl alcohol, polyvinyl ether, ethyl cellulose, methyl cellulose, gum labia, tragacanth.

ゼラチン、シェラツク、ヒドロキシプロピルセル１一ス
、ヒド１士ジプロピルスターチ、ポリビニルピロリドン
などが、崩壊剤としては例えば、デンプン、寒天、ゼラ
チン末、結晶セルロース、炭酸カルシウム、炭酸水素ナ
トリウム、クエン酸カルシウム、デキストリン、ペクチ
ン等が、滑沢剤としては例えば、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、硬化
植物油等が１着色剤としては医薬品に添加することが許
Ｏ（されているものが、矯味矯臭剤としては。Gelatin, shellac, hydroxypropyl cellulose, dipropyl starch, polyvinylpyrrolidone, etc., and examples of disintegrants include starch, agar, gelatin powder, crystalline cellulose, calcium carbonate, sodium bicarbonate, calcium citrate, Examples of lubricants include dextrin and pectin; examples of lubricants include magnesium stearate, talc, polyethylene glycol, silica, and hydrogenated vegetable oils; examples of colorants that are allowed to be added to pharmaceuticals include flavoring and flavoring agents; As a drug.

ココア末、ハツカ脳、芳香酸、ハツカ油、竜脳。Cocoa powder, peppermint, aromatic acid, peppermint oil, dragonbrain.

桂皮末等が用いられる。これらの錠剤、顆粒剤には糖衣
、ゼラチン衣、その他必要により適宜コーティングする
ことはもちろんさしつかえない。Cinnamon powder etc. are used. Of course, these tablets and granules may be coated with sugar coating, gelatin coating, or other coatings as appropriate.

注射剤を調製する場合には、主薬に必要によりｐｕｇ整
削１緩衝剤、安定化剤、保存剤、可溶化剤などを添加し
、常法により皮下、筋肉内、静脈内用注射剤とする。When preparing injections, add buffering agents, stabilizers, preservatives, solubilizers, etc. to the main drug as necessary, and prepare subcutaneous, intramuscular, or intravenous injections using conventional methods. .

家畜、家禽などの動物に投与する際も、経口投与若しく
は非経口投与により投与する。経口譚与は通常飼料に添
加しておこなう。また非経口投与の例をあげれば、常法
により注射剤を調製し、皮ド、筋肉内、静脈内などに投
与する。When administering to animals such as livestock and poultry, the drug is administered orally or parenterally. Oral feeding is usually done by adding it to the feed. As an example of parenteral administration, an injection is prepared by a conventional method and administered intradermally, intramuscularly, intravenously, etc.

ル（以Ｆ主薬と称する）を有効成分とした製剤例を示す
〇 製剤例１　　（カプセル削） 上　　　　薬　　　　　　　　　　　　　　　　　５ｇ
微結晶セルローズ　　　　　　　　８０Ｉｊトウモロコ
シデンゾン　　　　　　　２０９乳　　　　糖　　　　
　　　　　　　　　　２２９ポリビニルピロリドン　　
　　　　　　３ｇＬ記上記を常法により精粒化したのち
、ぜラチン硬カプセルｌ、（１００カゾゼルに充填した
。１力！セル中に主薬５〜を３自する。〇Preparation example 1 (capsule cut) Top drug 5g
Microcrystalline cellulose 80Ij Corn Denzone 209 Lactose
229 polyvinylpyrrolidone
After pulverizing 3gL of the above powder by a conventional method, it was filled into 100 gelatin hard capsules.5 to 3 grams of the main drug was poured into each cell.

製剤例２　（散　　剤） 上　　　　薬　　　　　　　　　　　　　　　　５０９
微結晶セルロー７：４００　Ｍ トウモロコシデンプン　　　　　　５５０９全　　　皺
　　　　　　−１，００（１主薬をアセトンに溶解し９
次いでこれを微結晶セルローズに吸着させたのち、乾燥
した。これをトウモロコシデンプンと混合し、常法によ
り散剤として、１ミ桑の加倍散を調製した。Formulation example 2 (powder) Drug 509
Microcrystalline cellulose 7: 400 M corn starch 5509 total wrinkles -1,00 (1 main ingredient dissolved in acetone, 9
Next, this was adsorbed onto microcrystalline cellulose and then dried. This was mixed with corn starch and a powder of 1 mi mulberry was prepared by a conventional method.

製剤例３　（錠　　　剤） Ｌ　　　　薬　　　　　　　　　　　　　　　　５ｆト
ウモロコシデンプン　　　　　　　ｌ（１乳　　　　糖
　　　　　　　　　　　　　　２（Ｈｌカルボ＋ジメチ
ルセルａ−ズカルシウム　　　　　１０ｇ！微結晶セル
ローズ　　　　　　　　４０ｆ！ポリビニルピロリドン
　　　　　　　５ｇ主薬をア竜トン＃Ｃ溶解し１次いで
これを微結晶セルローズに吸着させたのち、乾燥した。Formulation Example 3 (Tablets) L Medicine 5f Corn Starch 1 (1 Lactose 2 (Hl Carbo+Dimethylcellulose Calcium 10g! Microcrystalline Cellulose 40f! Polyvinylpyrrolidone 5g) Dissolve the main drug in Aryuton #C 1. Then dissolve this was adsorbed onto microcrystalline cellulose and then dried.

これにトウモロコシデンプン、乳糖、カルボキシメチル
セルローズカルシウムを混合し１次いでポリビニルピロ
リドンの水溶液を結合剤として加えて常法により精粒化
した。これに滑沢剤としてタルクを加えて混合したのち
、１錠１００■の錠剤に打錠した。１綻中には主薬５ｉ
ｌｖを含有する。Corn starch, lactose, and carboxymethyl cellulose calcium were mixed with this mixture, and then an aqueous solution of polyvinylpyrrolidone was added as a binder, and the mixture was refined by a conventional method. Talc was added as a lubricant and mixed, and then the mixture was compressed into 100 square tablets. Main drug 5i in 1 shot
Contains lv.

製剤例４　（注　射　剤） 主　　　　桑　　　　　　　　　　　　　　　　１０９
Ｎｉｋｋｏｌ　ｔｉｅ（Ｊ−６０（ＩＪ先ゲミカル社製
品名）３７ｆ／ゴ　　マ　　油　　　　　　　　　　　
　　　　　　　　２ノ塩化ナトリウム　　　　　　　　
　　９ノプロピレングリコール　　　　　　４０９主薬
、　Ｎ１ｋｋｏｌ　ＨｅＵ　−６０，ゴマ油および半蓋
のプロピレングリコールを混合して約ｍ”ｃで加温溶解
し、これにリン酸緩衡液および塩化ナトリウムとプロピ
レングリコールを予め溶解した蒸留水を約（資）℃に加
湿して加え、全ｊｌｌ、０００□、ｌの水溶液とした。Formulation example 4 (injection) Main Mulberry 109
Nikkol tie (J-60 (product name of IJ Chemical Co., Ltd.) 37f/sesame oil
Sodium chloride
9 Nopropylene glycol 409 main ingredient, N1kkol HeU-60, sesame oil and half a cap of propylene glycol were mixed and dissolved by heating at about m''c, and phosphoric acid buffer, sodium chloride and propylene glycol were pre-dissolved in this. Distilled water was added while humidifying the mixture to approximately (1)°C to obtain an aqueous solution with a total volume of 1,000 □, 1.

この水溶液を２ｍ／のアンプルに分注して溶閉したのち
、加熱滅菌した。This aqueous solution was dispensed into ampoules of 2 m/m, which were fused and sealed, and then sterilized by heating.

ｌ管中、主薬」〜を特徴する 特許出願人 工−ザイ株′Ａ会社Characterized by "main drug" patent applicant Ko-Zai Co., Ltd.'A Company

Claims (2)

【特許請求の範囲】[Claims] （１）一般式 （式中ａ、ｂは水素ｂＸ　ｆまたはａ−ｂで結合トを形
成する。ｎは１−１０の整数を示す。）で表オ〕される
ポリプレニルアルコール系化合物を自効成分とするヒト
または動物の免疫機能不全による疾患の予防・治療剤。(1) A polyprenyl alcohol compound represented by the general formula (where a and b are hydrogen bX f or a-b to form a bond; n is an integer from 1 to 10). A prophylactic/therapeutic agent for diseases caused by immune dysfunction in humans or animals. （２）一般式 Ｃ式中ａ、ｂは水素原子またはａ−ｂで結合１−４形成
する。【１は１〜ｌＯの整数を示す。）で表わされるポ
リプレニルアルコール系化合物を有効成分とするヒトま
たは動物の感染症に対する防禦剤。(2) General Formula C In the formula, a and b are hydrogen atoms or a-b to form bonds 1-4. [1 represents an integer from 1 to 1O. ) A preventive agent against infectious diseases in humans or animals, which contains a polyprenyl alcohol compound represented by the following as an active ingredient.
JP57089806A 1982-05-28 1982-05-28 Preventive and remedy for disease caused by immunoinsufficiency Granted JPS58206517A (en)

Priority Applications (41)

Application Number Priority Date Filing Date Title
JP57089806A JPS58206517A (en) 1982-05-28 1982-05-28 Preventive and remedy for disease caused by immunoinsufficiency
DE3348493A DE3348493C2 (en) 1982-05-28 1983-05-25 Di:hydro-poly:prenyl alcohol and ester and ether derivs.
GB08314419A GB2122610B (en) 1982-05-28 1983-05-25 A polyprenyl compound and a pharmaceutical composition containing a polyprenyl compound
DE3348492A DE3348492C2 (en) 1982-05-28 1983-05-25 Di:hydro-poly:prenyl alcohol and ester and ether derivs.
DE3318989A DE3318989C2 (en) 1982-05-28 1983-05-25 ß, gamma-dihydropolyprenyl alcohol derivatives and medicaments containing them and their use
DE3348500A DE3348500C2 (en) 1982-05-28 1983-05-25 beta, gamma-dihydropolyprenyl alcohol derivative
BE2/60109A BE896865A (en) 1982-05-28 1983-05-27 ALCOHOL BETA DERIVATIVES, ALPHA-DIHYDROPOLYPRENYLIC AND PHARMACEUTICAL COMPOSITION CONTAINING A POLYPRENYL COMPOUND.
SE8303013A SE461650B (en) 1982-05-28 1983-05-27 B-DIHYDROPOLYPRENYL ALCOHOL DERIVATIVES AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
ES522789A ES522789A0 (en) 1982-05-28 1983-05-27 A DERIVATIVE OF ALCOHOL B, V-DIHIDROPOLIPRENILICO.
NL8301892A NL194300C (en) 1982-05-28 1983-05-27 Pharmaceutical composition containing a polyprenol as an active ingredient and polyprenols suitable for use therein.
CA000429108A CA1310660C (en) 1982-05-28 1983-05-27 B, -dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
CH2902/83A CH654823A5 (en) 1982-05-28 1983-05-27 ALCOHOL DERIVATIVES BETA, GAMMA-DIHYDROPOLYPRENYLIQUE AND PHARMACEUTICAL COMPOSITIONS CONTAINING A POLYPRENYLIC COMPOUND.
DK239483A DK171640B1 (en) 1982-05-28 1983-05-27 Analogous Process for Preparation of Beta, Gamma-dihydro-polyprenyl Alcohol Derivatives
FR838308941A FR2527597B1 (en) 1982-05-28 1983-05-30 ALCOHOL B DERIVATIVES, G-DIHYDROPOLYPRENYLIC AND PHARMACEUTICAL COMPOSITION CONTAINING A POLYPRENYLIC COMPOUND
IT21364/83A IT1164256B (en) 1982-05-28 1983-05-30 BETA DERIVATIVES, ALPHA DIHYDROPOLIPRENYL ALCOHOL AND PHARMACEUTICAL COMPOSITION CONTAINING A POLYPRENYL COMPOUND
AT0197283A AT389871B (en) 1982-05-28 1983-05-30 METHOD FOR PRODUCING BETA, GAMMA -DIHYDROPOLYPRENYL ALCOHOL DERIVATIVES
FR8317173A FR2532845B1 (en) 1982-05-28 1983-10-27 PHARMACEUTICAL COMPOSITION COMPRISING DOCOSANOL AS ACTIVE INGREDIENT
FR8317171A FR2532844B1 (en) 1982-05-28 1983-10-27 PHARMACEUTICAL COMPOSITION CONTAINING A POLYPRENYL COMPOUND
FR8317176A FR2532847B1 (en) 1982-05-28 1983-10-27 PHARMACEUTICAL COMPOSITION COMPRISING AS ACTIVE INGREDIENT 3,7,11,15-TETRAMETHYLHEXADECA-1-ENE-3-OL
FR8317170A FR2532848B1 (en) 1982-05-28 1983-10-27 PHARMACEUTICAL COMPOSITION CONTAINING A POLYPRENYL DERIVATIVE
FR8317175A FR2532846B1 (en) 1982-05-28 1983-10-27 PHARMACEUTICAL COMPOSITION COMPRISING AS ACTIVE INGREDIENT 3,7,11,15 - TETRAMETHYL -1,6,10,14-HEXADECATETRAENE-3-OL
FR8317169A FR2532843A1 (en) 1982-05-28 1983-10-27 PHARMACEUTICAL COMPOSITION COMPRISING PHYTOL OR ISOPHYTOL AS ACTIVE INGREDIENT
ES529754A ES8507444A1 (en) 1982-05-28 1984-02-15 Beta, gamma-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
ES529753A ES8506567A1 (en) 1982-05-28 1984-02-15 Beta, gamma-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
GB08508218A GB2159711B (en) 1982-05-28 1985-03-29 Containing a polyprenyl compound
GB08508216A GB2159055B (en) 1982-05-28 1985-03-29 Pharmaceutical compositions of 3,7,11,15-tetra-methylhexadec-1-en-3-ol
GB08508214A GB2159054B (en) 1982-05-28 1985-03-29 Pharmaceutical compositions of polyprenyl alcohols
GB08508217A GB2159710B (en) 1982-05-28 1985-03-29 Containing a polyprenyl compound
GB08508215A GB2159709B (en) 1982-05-28 1985-03-29 Containing a polyprenyl compound
GB08508219A GB2159712B (en) 1982-05-28 1985-03-29 Containing a polyprenyl compound
GB08508220A GB2159713A (en) 1982-05-28 1985-03-29 Containing a polyprenyl compound
US06/760,221 US4624966A (en) 1982-05-28 1985-07-29 β,γ-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
FR858513026A FR2569108B1 (en) 1982-05-28 1985-09-02 PHARMACEUTICAL COMPOSITION CONTAINING A POLYPRENYL COMPOUND
SE8801515A SE502924C2 (en) 1982-05-28 1988-04-22 Pharmaceutical composition containing an effective amount of 3,7,11,15-tetramethyl-hexadeca-1-en-3-ol or 3,7,11,15-tetramethyl-1,6,10,14-hexadecatetraen-3-ol
SE8801513A SE502922C2 (en) 1982-05-28 1988-04-22 Use of a polyprenyl compound for the preparation of prophylactic / therapeutic agent for human and animal diseases due to defective immune system
SE8801514A SE502923C2 (en) 1982-05-28 1988-04-22 Use of a polyprenyl compound for the preparation of protylactic / therapeutic agent for human and animal diseases due to defective immune system
US08/011,197 US5280048A (en) 1982-05-28 1993-01-29 β,γ-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
US08/584,145 US6111131A (en) 1982-05-28 1996-01-11 Beta, gamma-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
US08/601,489 US6288128B1 (en) 1982-05-28 1996-02-14 β,γ-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
US08/599,944 US5658958A (en) 1982-05-28 1996-02-14 β, γ-dihydropolyprenyl alcohol derivatives effective at mitigating stress in animals
NL9900009A NL9900009A (en) 1982-05-28 2000-12-05 Di:hydro-poly:prenyl alcohol and ester and ether derivs.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57089806A JPS58206517A (en) 1982-05-28 1982-05-28 Preventive and remedy for disease caused by immunoinsufficiency

Publications (2)

Publication Number Publication Date
JPS58206517A true JPS58206517A (en) 1983-12-01
JPH026326B2 JPH026326B2 (en) 1990-02-08

Family

ID=13980959

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57089806A Granted JPS58206517A (en) 1982-05-28 1982-05-28 Preventive and remedy for disease caused by immunoinsufficiency

Country Status (2)

Country Link
JP (1) JPS58206517A (en)
BE (1) BE896865A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5973533A (en) * 1982-10-21 1984-04-25 Eisai Co Ltd Beta,gamma-dihydropolyprenyl alcohol derivative

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5973533A (en) * 1982-10-21 1984-04-25 Eisai Co Ltd Beta,gamma-dihydropolyprenyl alcohol derivative
JPH02330B2 (en) * 1982-10-21 1990-01-08 Eisai Co Ltd

Also Published As

Publication number Publication date
BE896865A (en) 1983-11-28
JPH026326B2 (en) 1990-02-08

Similar Documents

Publication Publication Date Title
AT389871B (en) METHOD FOR PRODUCING BETA, GAMMA -DIHYDROPOLYPRENYL ALCOHOL DERIVATIVES
US20230090435A1 (en) Compounds with Antimicrobial Properties
JPH09512831A (en) Dibenzimidazole derivative
EP3786158A1 (en) Cyclohexenyl compounds, compositions comprising them and uses thereof
JP4394686B2 (en) Pharmaceutical composition for promoting salivation and use thereof
JP2020503366A (en) Glauco calixin A derivatives, pharmaceutically acceptable salts or pharmaceutical compositions thereof, and their use in preparing medicaments for treating psoriasis
JPS58206517A (en) Preventive and remedy for disease caused by immunoinsufficiency
EP0500953A1 (en) Antineoplastic effect potentiator and antineoplastic agent
US5534513A (en) Antitumor potentiator and antitumor composition
JP3982889B2 (en) Pharmaceutical preparations containing ibuprofen
HU176505B (en) Process for producing new n-bracket-2-comma above-carboxy-phenyl-bracket closed-4-chloro-antranylic acid derivatives
US4315003A (en) Compositions containing azo compounds and use thereof for therapeutic treatment
AU5083690A (en) Pharmaceutical and veterinary compositions for the treatment or prevention of helminthiasis
JPH05502435A (en) Drugs for the treatment of cryptosporidiosis
JPH0372468A (en) Triazole compound and antifungal agent containing the same
JPH02172920A (en) Antitumor agent
JPS58225014A (en) Preventive and remedy for disease caused by incompetence of immune function
CN115554301A (en) Use of an HDAC inhibitor and ibrutinib for the preparation of a medicament for the prevention or treatment of mantle cell lymphoma
JPS624226A (en) Drug containing 1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6- (alpha-methylstyryl)naphthalene
JPS5973513A (en) Preventive and remedy for disease caused by immunological function insufficiency
JPH07502986A (en) Naphthoquinone derivatives for the treatment of infections caused by parasites
JPS6189A (en) Novel 6 beta-halopenicillanate, manufacture and use
US4127664A (en) Method for treating blackhead disease
JPH0120128B2 (en)
JP2832363B2 (en) Hepatic encephalopathy treatment