DK162524C - Analogifremgangsmaade til fremstilling af 5-alkylthio-tetrazolderivater - Google Patents

Analogifremgangsmaade til fremstilling af 5-alkylthio-tetrazolderivater

Info

Publication number
DK162524C
DK162524C DK088081A DK88081A DK162524C DK 162524 C DK162524 C DK 162524C DK 088081 A DK088081 A DK 088081A DK 88081 A DK88081 A DK 88081A DK 162524 C DK162524 C DK 162524C
Authority
DK
Denmark
Prior art keywords
tetrazold
alkylthio
derivatives
preparation
analogy procedure
Prior art date
Application number
DK088081A
Other languages
English (en)
Other versions
DK162524B (da
DK88081A (da
Inventor
Minoru Uchida
Takao Nishi
Kazuyuki Nakagawa
Original Assignee
Otsuka Pharma 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
Priority claimed from JP2552180A external-priority patent/JPS56122363A/ja
Priority claimed from JP2570880A external-priority patent/JPS56122365A/ja
Priority claimed from JP2570780A external-priority patent/JPS56122364A/ja
Priority claimed from JP2708480A external-priority patent/JPS56122366A/ja
Priority claimed from JP55128160A external-priority patent/JPS5750968A/ja
Priority claimed from JP13690280A external-priority patent/JPS5759877A/ja
Priority claimed from JP14005180A external-priority patent/JPS5764682A/ja
Application filed by Otsuka Pharma Co Ltd filed Critical Otsuka Pharma Co Ltd
Publication of DK88081A publication Critical patent/DK88081A/da
Publication of DK162524B publication Critical patent/DK162524B/da
Application granted granted Critical
Publication of DK162524C publication Critical patent/DK162524C/da

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/327—Saturated compounds containing keto groups bound to rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
DK088081A 1980-02-29 1981-02-26 Analogifremgangsmaade til fremstilling af 5-alkylthio-tetrazolderivater DK162524C (da)

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
JP2552180A JPS56122363A (en) 1980-02-29 1980-02-29 Tetrazole derivative
JP2552180 1980-02-29
JP2570880A JPS56122365A (en) 1980-03-01 1980-03-01 Tetrazole derivative
JP2570780A JPS56122364A (en) 1980-03-01 1980-03-01 Tetrazole derivative
JP2570780 1980-03-01
JP2570880 1980-03-01
JP2708480 1980-03-03
JP2708480A JPS56122366A (en) 1980-03-03 1980-03-03 Tetrazole derivative
JP12816080 1980-09-16
JP55128160A JPS5750968A (en) 1980-09-16 1980-09-16 Carboxylic acid amide derivative
JP13690280 1980-09-30
JP13690280A JPS5759877A (en) 1980-09-30 1980-09-30 Tetrazole derivative
JP14005180 1980-10-06
JP14005180A JPS5764682A (en) 1980-10-06 1980-10-06 Tetrazole derivative

Publications (3)

Publication Number Publication Date
DK88081A DK88081A (da) 1981-08-30
DK162524B DK162524B (da) 1991-11-11
DK162524C true DK162524C (da) 1992-03-30

Family

ID=27564068

Family Applications (1)

Application Number Title Priority Date Filing Date
DK088081A DK162524C (da) 1980-02-29 1981-02-26 Analogifremgangsmaade til fremstilling af 5-alkylthio-tetrazolderivater

Country Status (10)

Country Link
US (1) US4372953A (da)
EP (1) EP0035228B1 (da)
AU (1) AU537266B2 (da)
CA (1) CA1162196A (da)
DE (1) DE3167997D1 (da)
DK (1) DK162524C (da)
FI (1) FI73423C (da)
NO (1) NO166320C (da)
PH (1) PH17406A (da)
PT (1) PT72569B (da)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5536447A (en) * 1978-09-07 1980-03-14 Otsuka Pharmaceut Co Ltd Butyramide derivative
US4443443A (en) * 1979-12-17 1984-04-17 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds
IN158869B (da) * 1981-03-18 1987-02-07 Ici Plc
DE3267110D1 (de) * 1981-05-18 1985-12-05 Ici Plc Amidine derivatives
GR78697B (da) * 1982-10-21 1984-09-27 Lilly Industries Ltd
US4661505A (en) * 1982-11-03 1987-04-28 Eli Lilly And Company Leukotriene antagonists
GB8318889D0 (en) * 1983-07-13 1983-08-17 Lilly Industries Ltd Pharmaceutical compounds
EP0239129B1 (en) * 1986-03-28 1991-09-25 Otsuka Pharmaceutical Co., Ltd. Hydroquinoline compounds, compositions containing same and processes for preparing same
KR940000785B1 (ko) * 1986-04-02 1994-01-31 오오쓰까세이야꾸 가부시끼가이샤 카르보스티릴 유도체 및 그의 염의 제조 방법
US5055481A (en) * 1989-03-24 1991-10-08 Wakamoto Pharmaceutical Co., Ltd. Tetrazole derivatives and aldose reductase inhibition therewith
US5177092A (en) * 1989-07-31 1993-01-05 Merck & Co., Inc. Medicinal use of certain tetrazolium salts
US5047416A (en) * 1989-07-31 1991-09-10 Merck & Co., Inc. Triazole compounds and their use as transglutaminase inhibitors
US5200419A (en) * 1990-05-21 1993-04-06 Warner-Lambert Company Substituted tetrazoles and derivatives thereof acting at muscarinic receptors
JPH04297466A (ja) * 1990-06-22 1992-10-21 Nippon Shinyaku Co Ltd テトラゾール誘導体及び医薬
HU209793B (en) * 1990-09-25 1994-11-28 Chinoin Gyogyszer Es Vegyeszet Process for the production of pyrido[1,2-a]pyrimidine-derivatives and pharmaceutical compositions containing the same
JPH04244070A (ja) * 1991-01-18 1992-09-01 Wakamoto Pharmaceut Co Ltd アルドース還元酵素阻害作用を有するテトラゾール酢酸誘導体
CN1037681C (zh) * 1991-01-31 1998-03-11 日本新药株式会社 四唑衍生物与医药
TW218875B (da) * 1992-03-09 1994-01-11 Takeda Pharm Industry Co Ltd
US5462934A (en) * 1992-03-09 1995-10-31 Takeda Chemical Industries Condensed heterocyclic ketone derivatives and their use
US6825214B2 (en) 2000-08-14 2004-11-30 Teva Pharmaceutical Industries, Ltd. Substantially pure cilostazol and processes for making same
AU2001250892A1 (en) 2000-03-20 2001-10-03 Teva Pharmaceutical Industries Ltd. Processes for preparing 6-hydroxy-3,4-dihydroquinolinone, cilostazol and n-(4-methoxyphenyl)-3-chloropropionamide
US6515128B2 (en) 2000-03-20 2003-02-04 Teva Pharmaceutical Industries Ltd. Processes for preparing cilostazol
AU2002354410A1 (en) * 2001-12-05 2003-06-17 Japan Tobacco Inc. Triazole compound and medicinal use thereof
GB0316546D0 (en) 2003-07-15 2003-08-20 Novartis Ag Process for the manufacture of organic compounds
WO2021222773A1 (en) 2020-04-30 2021-11-04 MBI Distributing Compositions comprising n-acetyl methyl gaba and related methods

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2507337A (en) * 1946-06-12 1950-05-09 Bilhuber Inc E 1, 5-dialkyl tetrazoles and preparation thereof
US3578674A (en) * 1969-12-24 1971-05-11 Miles Lab Derivatives of tetrazolyl alkanoic acids
US3743646A (en) * 1970-11-09 1973-07-03 Miles Lab Amides of 3-(2-halophenyl-5-tetrazolyl)propionic acids
DE2147023C3 (de) * 1971-09-21 1982-04-29 Fujisawa Pharmaceutical Co., Ltd., Osaka Verfahren zur Herstellung von 1H- Tetrazol-Verbindungen
NL7414119A (nl) * 1973-10-31 1975-05-02 Fujisawa Pharmaceutical Co Werkwijze ter bereiding van 1h-tetrazool-5-thiol- derivaten en 1-gesubstitueerde 1h-tetrazool- -5-thiolen.

Also Published As

Publication number Publication date
DE3167997D1 (en) 1985-02-14
CA1162196A (en) 1984-02-14
FI73423C (fi) 1987-10-09
EP0035228B1 (en) 1985-01-02
NO166320B (no) 1991-03-25
PH17406A (en) 1984-08-08
DK162524B (da) 1991-11-11
US4372953A (en) 1983-02-08
DK88081A (da) 1981-08-30
PT72569A (en) 1981-03-01
AU6763881A (en) 1981-09-03
FI73423B (fi) 1987-06-30
EP0035228A1 (en) 1981-09-09
NO166320C (no) 1991-07-03
NO810675L (no) 1981-08-31
PT72569B (en) 1982-02-17
FI810571L (fi) 1981-08-30
AU537266B2 (en) 1984-06-14

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