ES402651A1 - Cephalosporin compounds - Google Patents

Cephalosporin compounds

Info

Publication number
ES402651A1
ES402651A1 ES402651A ES402651A ES402651A1 ES 402651 A1 ES402651 A1 ES 402651A1 ES 402651 A ES402651 A ES 402651A ES 402651 A ES402651 A ES 402651A ES 402651 A1 ES402651 A1 ES 402651A1
Authority
ES
Spain
Prior art keywords
compound
group
see formula
formula
isomer
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
Application number
ES402651A
Other languages
Spanish (es)
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26251025&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ES402651(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Publication of ES402651A1 publication Critical patent/ES402651A1/en
Expired legal-status Critical Current

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Classifications

    • 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
    • C07D307/42—Singly bound oxygen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/14—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso 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
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • 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
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • 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
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procedure for the preparation of cephalosporin derivatives of the formula **(See formula)** (where R is a hydrogen atom or an organic group, Ra is an etherifying monovalent organic group attached to the oxygen atom through a carbon atom, B is (see formula) and Z is a group in which 2 carbon atoms join the nuclear sulfur atom and the carbon atom that carries the carboxylic acid group and that has unsaturation Δ 3), and its derivatives, which comprises condensing a compound of the formula **(See formula)** (where B and Z have the meanings defined above and R10 is hydrogen or a carboxyl blocking group) with an acylating agent corresponding to the acid **(See formula)** (in which R ° and Ra have the meanings defined above) or with an acylating agent corresponding to an acid that is a precursor of acid (IV), after which, if necessary or desired in each case, they are carried out any of the following reactions (i) conversion of a precursor to the desired group (see formula) in said group (ii) conversion of an Δ 2 isomer to the desired Δ 3 isomer (iii) removal of any carboxy blocking groups; (iv) reduction of a compound in which Z is (see formula) to form the desired compound in which (see formula); (v) reduction of a compound in which Y is azide to form a 3-aminomethyl compound and, if required, acylation of the resulting amino group to form a corresponding 3-acylaminomethyl compound; (vi) reaction of a compound in which Y is azido with a dipolarphile to form a compound having a polyazole ring attached to the 3-methylene group; (vii) deacylation of a compound in which Y is an acyloxy group to form a 3-hydroxymethyl compound; and (viii) acylation of a compound in which Y is hydroxy to form a 3-acyloxymethyl or 3-carbamoyloxymethyl compound; and recovering the desired compound of formula (I) in the form of the isomer without or in the form of a mixture containing at least 75% of the isomer without. (Machine-translation by Google Translate, not legally binding)
ES402651A 1971-05-14 1972-05-12 Cephalosporin compounds Expired ES402651A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1508271A GB1399086A (en) 1971-05-14 1971-05-14 Cephalosporin compounds
GB4588471 1971-10-01

Publications (1)

Publication Number Publication Date
ES402651A1 true ES402651A1 (en) 1975-11-01

Family

ID=26251025

Family Applications (2)

Application Number Title Priority Date Filing Date
ES402651A Expired ES402651A1 (en) 1971-05-14 1972-05-12 Cephalosporin compounds
ES430104A Expired ES430104A1 (en) 1971-05-14 1974-09-16 Cephalosporin compounds

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES430104A Expired ES430104A1 (en) 1971-05-14 1974-09-16 Cephalosporin compounds

Country Status (22)

Country Link
JP (3) JPS531280B1 (en)
AT (1) AT336786B (en)
BE (1) BE783449A (en)
CA (1) CA1027554A (en)
CH (1) CH591497A5 (en)
CS (2) CS245754B2 (en)
CY (1) CY971A (en)
DE (2) DE2223375C2 (en)
DK (1) DK155187C (en)
ES (2) ES402651A1 (en)
FR (2) FR2137899B1 (en)
GB (1) GB1399086A (en)
HK (1) HK66078A (en)
IE (1) IE38172B1 (en)
IL (1) IL39429A (en)
KE (1) KE2895A (en)
MY (1) MY7800466A (en)
NL (1) NL166688C (en)
NO (1) NO154797C (en)
PH (1) PH11205A (en)
SE (1) SE457795B (en)
YU (2) YU41807B (en)

Families Citing this family (124)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4033950A (en) * 1971-05-14 1977-07-05 Glaxo Laboratories Limited 3-Hydroxymethyl-7β-(2-alkoxy-or benzyloxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof
US4079178A (en) * 1971-05-14 1978-03-14 Glaxo Laboratories Limited Cephalosporins having (α-etherified oximino) acylamido groups at the 7-position
US4064346A (en) * 1971-05-14 1977-12-20 Glaxo Laboratories Limited 3-Acetoxymethyl-7β-(2-carboxy-methoxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof
GB1399086A (en) * 1971-05-14 1975-06-25 Glaxo Lab Ltd Cephalosporin compounds
US4138555A (en) 1971-05-14 1979-02-06 Glaxo Laboratories, Limited (6R,7R)-7-[2-aryl-2-(etherified oximino)acetamido]-3-carbamoyloxymethylceph-3-em-4-carboxylic acid 1-oxides
GB1445979A (en) * 1972-10-25 1976-08-11 Glaxo Lab Ltd Cephalosporin derivatives
AR207341A1 (en) * 1973-03-15 1976-09-30 Fujisawa Pharmaceutical Co A PROCEDURE FOR THE PREPARATION OF 2-ALKYL-2 OR 3-CEFEM-4-CARBOXYL ACID DERIVATIVES
US4144393A (en) 1973-12-21 1979-03-13 Glaxo Laboratories Limited 3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group
US4144392A (en) 1973-12-21 1979-03-13 Glaxo Laboratories Limited Cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyimino-arylacetamido group and at position-3 the residue of a sulphur nucleophile
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DK162391C (en) * 1976-04-12 1992-03-09 Fujisawa Pharmaceutical Co ANALOGY PROCEDURE FOR PREPARING SYN-ISOMERS OF 3,7-DISUBSTITUTED 3-CEPHEM-4-CARBOXYLIC ACID COMPOUNDS
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US4066762A (en) * 1976-07-12 1978-01-03 Smithkline Corporation Derivatives of 7-(2-substituted-2-hydroxyiminoacetamido)-3-(1-substituted tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid
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SE439312B (en) 1977-03-25 1985-06-10 Roussel Uclaf SET TO MAKE NEW OXIME DERIVATIVES OF 3-ACETOXIMETHYL-7-AMINOTIAZOLYLACETAMIDO CEPHALOSPORANIC ACID
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IT1192287B (en) * 1977-11-14 1988-03-31 Fujisawa Pharmaceutical Co PHARMACEUTICAL ACTION DERIVATIVES OF CEPHALOSPORANIC ACID AND RELATED PREPARATION PROCEDURE
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FR2438051A2 (en) * 1978-10-05 1980-04-30 Roussel Uclaf 3-Azido:methyl-3-cephem-4-carboxylic acid derivs. - useful as broad-spectrum antibacterial agents and disinfectants (BE 15.10.79)
DE2822861A1 (en) * 1978-05-26 1979-11-29 Hoechst Ag CEPHEMDER DERIVATIVES AND PROCESS FOR THEIR PRODUCTION
AR229883A1 (en) * 1978-05-26 1983-12-30 Glaxo Group Ltd PROCEDURE FOR THE PREPARATION OF ANTIBIOTIC (6R, 7R) -7 - ((Z) -2- (2-AMINOTIAZOL-4-IL) -2- (2-CARBOXIPROP-2-OXIIMINO) -ACETAMIDO) -3- (1 -PIRIDINOMETIL) -CEF-3-EM-4-CARBOXYLATE
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US4268509A (en) * 1978-07-10 1981-05-19 Fujisawa Pharmaceutical Co., Ltd. New cephem compounds and processes for preparation thereof
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FR2476087A1 (en) * 1980-02-18 1981-08-21 Roussel Uclaf NOVEL OXIMES DERIVED FROM 3-ALKYLOXY OR 3-ALKYL-THIOMETHYL 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS MEDICAMENTS
EP0076528B1 (en) * 1980-02-18 1990-05-23 Roussel-Uclaf Oxime derivatives of 3-alkyloxy or 3-alkylthiomethyl 7-amino-thiazolylacetamido-cephalosporanic acid and their preparation
EP0037797A3 (en) * 1980-03-11 1981-12-16 Ciba-Geigy Ag Cephalosporin derivatives, process for their preparation, pharmaceutical compositions containing them and their application
ZA813787B (en) * 1980-06-18 1982-07-28 Fujisawa Pharmaceutical Co New cephem compounds and processes for preparation thereof
GR75644B (en) * 1980-06-18 1984-08-02 Fujisawa Pharmaceutical Co
IL63207A (en) * 1980-07-24 1985-09-29 Lonza Ag Process for the preparation of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyiminoacetic acid esters
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FR2494275A2 (en) * 1980-11-20 1982-05-21 Rhone Poulenc Ind NEW DERIVATIVES OF VINYL-3 CEPHALOSPORINS AND THEIR PREPARATION
FR2494276A2 (en) * 1980-11-20 1982-05-21 Rhone Poulenc Ind NEW VINYL-3 CEPHALOSPORINS, AND THEIR PREPARATION
FR2494279A1 (en) * 1980-11-20 1982-05-21 Rhone Poulenc Ind NEW OXACEPHALOSPORINS, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM
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CS245753B2 (en) 1986-10-16
NL7206403A (en) 1972-11-16
CA1027554A (en) 1978-03-07
NO154797C (en) 1986-12-29
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JPS5328141A (en) 1978-03-16
YU126772A (en) 1982-02-28
PH11205A (en) 1977-10-28
FR2137899A1 (en) 1972-12-29
DE2223375A1 (en) 1972-11-23
JPS54135792A (en) 1979-10-22
CH591497A5 (en) 1977-09-30
NL166688B (en) 1981-04-15
BE783449A (en) 1972-11-13
FR2137899B1 (en) 1976-08-20
NL166688C (en) 1985-01-16
GB1399086A (en) 1975-06-25
DK155187C (en) 1989-07-17
ATA420872A (en) 1976-09-15
IL39429A (en) 1978-04-30
YU41807B (en) 1988-02-29
IE38172L (en) 1972-11-14
DK155187B (en) 1989-02-27
IL39429A0 (en) 1972-07-26
KE2895A (en) 1978-11-10
FR2137900A1 (en) 1972-12-29
SE457795B (en) 1989-01-30
HK66078A (en) 1978-11-24
YU321379A (en) 1982-02-28
DE2223375C2 (en) 1985-05-15
IE38172B1 (en) 1978-01-18
FR2137900B1 (en) 1976-04-16
JPS6324993B2 (en) 1988-05-23
NO154797B (en) 1986-09-15
CS245754B2 (en) 1986-10-16
ES430104A1 (en) 1976-10-01
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JPS531280B1 (en) 1978-01-17
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AT336786B (en) 1977-05-25
CY971A (en) 1978-12-22

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