JPH0368875B2 - - Google Patents

Info

Publication number
JPH0368875B2
JPH0368875B2 JP57225098A JP22509882A JPH0368875B2 JP H0368875 B2 JPH0368875 B2 JP H0368875B2 JP 57225098 A JP57225098 A JP 57225098A JP 22509882 A JP22509882 A JP 22509882A JP H0368875 B2 JPH0368875 B2 JP H0368875B2
Authority
JP
Japan
Prior art keywords
formula
pharmaceutically acceptable
acid addition
compound
pyrimidinyl
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
Application number
JP57225098A
Other languages
English (en)
Other versions
JPS58118582A (ja
Inventor
Davis L Temple Jr
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.)
Bristol Myers Squibb Co
Original Assignee
Bristol Myers Squibb Co
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 Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of JPS58118582A publication Critical patent/JPS58118582A/ja
Publication of JPH0368875B2 publication Critical patent/JPH0368875B2/ja
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Psychiatry (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Description

【発明の詳細な説明】 本発明は２〔４−〔４，４−ジアルキル−２，６
−ピペリジンジオン−１−イル）ブチル〕−１−
ピペラジニル〕ピリミジンに関する。 関聯技術は次の構造式： （式中ｎは４又は５としまたＢは置換又は非置
換２−ピリミジル部分を表わす）をもつ化合物に
よつて一般化できる。これらの化合物はサイコト
ロピツク剤として製造されており次の文献に記載
されている。 ウーらのJournal of Medicinal Chemistry.，
1515，477−479（1972）． ウーらの1973年２月20日公告米国特許第
3717634号、ウーらの1975年９月23日公告米国特
許第390780号、ウーらの1976年８月24日公告米国
特許第3976776号、 バスピロンといわれる上記１化合物（ｎ＝４、
Ｂ＝２−ピリミジル）の不安解消用途は1980年２
月８日公告キヤステンらの米国特許第4182763号
に発表されている。最近不安神経症治療における
バスピロン使用について米国食品医療品行政部へ
の付託を支持する臨床研究が行なわれている。 グルタルイミドを含むがＢ置換基がフエニル又
は置換フエニルである他の関聯化合物群は次の文
献に発表されている： ウーらの1968年８月20日公告米国特許第
3398151号、ウーらのJournal of Medicinal
Chem.，1214 876−881（1969）、 相違点をもつものに1980年１月３日
GB2023594Aとして発表された英国特許出願第
7921307号のネイジヤー、H.，ら発表の次の構造
式： をもつ化合物がある。これらCNS活性化合物は
不安およびうつ病治療に有用であると記載されて
いる。 構造式： をもつピペリジル化合物はポルラードらのThe
Journal of Org.Chem.，2416 764−767（1950）
に報告されているが、用途が示されていない。 構造式： （式中R1はC1−C4アルキルを表わし、R2はＨ
又はC1−C4アルキルを表わす）で示されベニカ
らのJ.of Amer.Pharmaceutical Association
451−456（1950）に報告されたある３，３−ジア
ルキルグルタルイミドは多少関係がある。これら
のグルタルイミドの薬理学的試験は有用な生理学
的活性を余り示さなかつた。 上記文献に記載したとおりバスピロンは生物学
的に臨床効果のある不安解消剤の性質をもつてい
る。しかし3H−スピペロン結合研究およびアポ
モルフイン常同抑制の様なある生物学的方法にお
いてはバスピロンは神経弛緩活性又は精神病治療
活性を示す結果を与える。したがつて本発明の目
的は一連のより選ばれたCNS活性化合物、即ち
神経弛緩活性は欠くがバスピロンの新規の不安解
消性をもつ化合物の発見にあるのである。 本発明は次の一般式（）： を特徴とする一連の新規CNS−活性化合物およ
びそれらの製薬上許容される無毒酸付加塩に関す
る。上式中R1とR2は各々無関係にC1−C4アルキ
ル基を表わし、Ｚは水素、ヒドロキシル、ハロゲ
ン又はブソイドハロゲン、好ましくはフルオロ、
クロロ又はトリフルオロメチルを表わす。上記プ
ソイドハロゲンとは、ハロゲノアルキル、例えば
トリフルオロメチルを示す。 本発明の化合物は非常に注目すべきことにバス
ピロンおよびその関聯同族と異なりそのスピロア
ルキレン部分が１対のジアルキル基で置換されて
いる。 生物学的標準体系の試験によつて本発明化合物
は関聯スピロー同族体に比べて試験管内結合およ
び精神病治療活性を予見できる作用試験において
活性を欠くがバスピロンの独特な不安解消作用を
もつことが示されている。 式をもつ化合物製造には各実施態様（Ａ、Ｂ
およびＣ）を包含する単一方法が使用できる。こ
れらの方法は本発明に包含されるが特に詳記しな
い他の化合物生成のため変更して適用できる。同
一化合物を幾分ちがつた方法で製造する変更法は
この技術分野の知識ある者には明白であろう。い
くつかの実施例を特に例証して示す。 上図表におけるR1、R2およびＺは式につい
て前記したと同じ意味をもつ。記号“Ｗ”は
Ｏ、NH又はＮ−（CH2）4−Ｘであつてもよ
い。記号“Ｙ”はH2N−（CH2）4−、Ｘ−（CH2）4
−、【式】又はＨであつてもよい。Ｗと Ｙの関係は次のとおりである： 【表】 Ｗが

Claims (1)

  1. 【特許請求の範囲】 １ 式（） （式中R1とR2は各無関係にC1−C4アルキル基
    から選ばれたものとしまたＺは水素、ヒドロキシ
    ル、ハロゲン、又はプソイドハロゲンを表わす）、
    で示されることを特徴とする化合物及びその製薬
    上許容される無毒酸付加塩より成る群から選ばれ
    た化合物。 ２ Ｚが５−フルオロである特許請求の範囲第１
    項に記載の化合物。 ３ Ｚが５−ヒドロキシである特許請求の範囲第
    １項に記載の化合物。 ４ ４，４−ジメチル−１−〔４−〔４−（２−ピ
    リミジニル）−１−ピペラジニル〕ブチル〕−２，
    ４−ピペリジンジオン又はその製薬上許容される
    酸付加塩である特許請求の範囲第１項に記載の化
    合物。 ５ ４−エチル−４−メチル−１−〔４−〔４−
    （２−ピリミジニル）−１−ピペラジニル〕ブチ
    ル〕−２，６−ピペリジンジオン又はその製薬上
    許容される酸付加塩である特許請求の範囲第１項
    に記載の化合物。 ６ ４，４−ジエチル−１−〔４−〔４−（２−ピ
    リミジニル）−１−ピペラジニル〕ブチル〕−２，
    ６−ピペリジンジオン又はその製薬上許容される
    酸付加塩である特許請求の範囲第１項に記載の化
    合物。 ７ ４−メチル−４−プロピル−１−〔４−〔４−
    （２−ピリミジニル）−１−ピペラジニル〕ブチ
    ル〕−２，６−ピペリジンジオン又はその製薬上
    許容される酸付加塩である特許請求の範囲第１項
    に記載の化合物。 ８ ４，４−ジメチル−１−〔４−〔４−（５フル
    オロ−２−ピリミジニル）−１−ピペラジニル〕
    ブチル〕−２，６−ピペリジンジオン又はその製
    薬上許容される酸付加塩である特許請求の範囲第
    １項に記載の化合物。 ９ Ｚがフルオロ、クロロ又はトリフルオロメチ
    ルである特許請求の範囲第１項に記載の化合物。 １０ 式（）： （式中R1とR2は各々無関係にC1−C4アルキル
    基から選ばれたものとしかつＷはＯ、NH、
    又はＮ−（CH2）4−Ｘを表わし、但しＸはクロ
    ライド、ブロマイド、アイオダイド、サルフエイ
    ト、ホスフエイト、トシレイト又はメシレイトと
    する）をもつグルタル酸無水物又はイミドを式
    （）： （式中Ｚは水素、ヒドロキシル、ハロゲン又は
    プソイドハロゲンを表わしかつＹはH2N−
    （CH2）4−、Ｘ−（CH2）4−、【式】又は Ｈを表わす）をもつピリミジン誘導体と乾燥反応
    不活性媒質又は適当な有機液体中で酸結合剤と共
    に又は酸結合剤なしで適当な温度において式
    （）： （式中R1、R2およびＺは上に定義したとおり
    とする）をもつ化合物を生成するに十分の時間反
    応させ、および（又は）必要ならば式（）をも
    つ化合物をその製薬上許容される無毒酸付塩に転
    化することを特徴とする上記式（）で示される
    化合物およびその製薬上許容される無毒酸付塩の
    製法。 １１ ３，３−ジメチルグルタル酸無水物と１−
    （４−アミノブチル）−４−（２−ピリミジニル）
    ピペラジンの混合物を還流する不活性溶媒中、式
    （′）： をもつ遊離塩基を生成するに十分の時間反応させ
    た後上記式（′）をもつ遊離塩基を塩酸塩
    （′）又はその他の無毒酸付加塩に転化すること
    により成る化合物４，４−ジメチル−１−〔４−
    〔４−（２−ピリミジニル）−１−ピペラジニル〕
    ブチル〕−２，６−ピペリジンジオン塩酸塩
    （′）又はその他の無毒酸付加塩製造の特許請求
    の範囲第１０項に記載の方法。
JP57225098A 1981-12-28 1982-12-23 ２−〔４−〔（４，４−ジアルキル−２，６−ピペリジンジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン Granted JPS58118582A (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/334,688 US4423049A (en) 1981-12-28 1981-12-28 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyrimidines
US334688 1994-11-04

Publications (2)

Publication Number Publication Date
JPS58118582A JPS58118582A (ja) 1983-07-14
JPH0368875B2 true JPH0368875B2 (ja) 1991-10-30

Family

ID=23308351

Family Applications (2)

Application Number Title Priority Date Filing Date
JP57225098A Granted JPS58118582A (ja) 1981-12-28 1982-12-23 ２−〔４−〔（４，４−ジアルキル−２，６−ピペリジンジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン
JP3216768A Pending JPH06293753A (ja) 1981-12-28 1991-03-29 ２−〔４−〔（４，４−ジアルキル−２、６−ピペリジン ジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン含有組成物

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP3216768A Pending JPH06293753A (ja) 1981-12-28 1991-03-29 ２−〔４−〔（４，４−ジアルキル−２、６−ピペリジン ジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン含有組成物

Country Status (26)

Country Link
US (1) US4423049A (ja)
JP (2) JPS58118582A (ja)
KR (1) KR870001045B1 (ja)
AT (1) AT382373B (ja)
AU (1) AU555797B2 (ja)
BE (1) BE895504A (ja)
CA (1) CA1244426A (ja)
CH (1) CH656383A5 (ja)
CY (1) CY1379A (ja)
DE (1) DE3248160C2 (ja)
DK (1) DK162389C (ja)
ES (2) ES518510A0 (ja)
FI (1) FI70891C (ja)
FR (1) FR2518993B1 (ja)
GB (1) GB2114122B (ja)
GR (1) GR77045B (ja)
HK (1) HK5288A (ja)
IE (1) IE54619B1 (ja)
IT (1) IT1158039B (ja)
KE (1) KE3709A (ja)
LU (1) LU84561A1 (ja)
NL (1) NL193283C (ja)
PT (1) PT76036B (ja)
SE (1) SE453088B (ja)
SG (1) SG29787G (ja)
ZA (1) ZA828549B (ja)

Families Citing this family (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4423049A (en) * 1981-12-28 1983-12-27 Mead Johnson & Company 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyrimidines
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SE453088B (sv) 1988-01-11
IT1158039B (it) 1987-02-18
GB2114122A (en) 1983-08-17
IT8249719A1 (it) 1984-06-22
IE54619B1 (en) 1989-12-20
AU9108382A (en) 1983-07-07
US4423049A (en) 1983-12-27
FI70891B (fi) 1986-07-18
LU84561A1 (fr) 1983-09-08
FR2518993A1 (fr) 1983-07-01
HK5288A (en) 1988-01-29
SE8207425D0 (sv) 1982-12-27
SE8207425L (sv) 1983-08-12
PT76036A (en) 1983-01-01
ES8405786A1 (es) 1984-06-16
CA1244426A (en) 1988-11-08
NL193283C (nl) 1999-05-06
KR840002827A (ko) 1984-07-21
DK162389B (da) 1991-10-21
FR2518993B1 (fr) 1986-09-05
BE895504A (fr) 1983-06-28
ZA828549B (en) 1983-09-28
KE3709A (en) 1987-04-16
KR870001045B1 (ko) 1987-05-26
NL8204970A (nl) 1983-07-18
ES8506696A1 (es) 1985-08-01
DE3248160A1 (de) 1983-07-07
ES524945A0 (es) 1985-08-01
JPS58118582A (ja) 1983-07-14
SG29787G (en) 1987-07-17
CH656383A5 (de) 1986-06-30
FI824442A0 (fi) 1982-12-23
ATA469882A (de) 1986-07-15
DK573182A (da) 1983-06-29
GB2114122B (en) 1985-11-27
JPH06293753A (ja) 1994-10-21
AU555797B2 (en) 1986-10-09
AT382373B (de) 1987-02-25
DE3248160C2 (de) 1993-12-09
NL193283B (nl) 1999-01-04
FI824442L (fi) 1983-06-29
FI70891C (fi) 1986-10-27
IE823067L (en) 1983-06-28
PT76036B (en) 1985-12-16
CY1379A (en) 1987-08-07
ES518510A0 (es) 1984-06-16
GR77045B (ja) 1984-09-04
DK162389C (da) 1992-03-09
IT8249719A0 (it) 1982-12-22

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