JPH05255250A - 新規第四級アミンチオール化合物 - Google Patents

新規第四級アミンチオール化合物

Info

Publication number
JPH05255250A
JPH05255250A JP3274949A JP27494991A JPH05255250A JP H05255250 A JPH05255250 A JP H05255250A JP 3274949 A JP3274949 A JP 3274949A JP 27494991 A JP27494991 A JP 27494991A JP H05255250 A JPH05255250 A JP H05255250A
Authority
JP
Japan
Prior art keywords
chemical
formula
alkyl
mmol
group
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.)
Pending
Application number
JP3274949A
Other languages
English (en)
Japanese (ja)
Inventor
Pierre Dextraze
デキストリーズ ピエレ
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 JPH05255250A publication Critical patent/JPH05255250A/ja
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • 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
    • 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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen 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
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/02—Preparation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
JP3274949A 1983-03-08 1991-09-27 新規第四級アミンチオール化合物 Pending JPH05255250A (ja)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US47137883A 1983-03-08 1983-03-08
US471378 1983-03-08
US49969183A 1983-06-07 1983-06-07
US499691 1983-06-07
US55729583A 1983-12-01 1983-12-01
US557295 1983-12-01

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
JP59043038A Division JPS59210087A (ja) 1983-03-08 1984-03-08 カルバペネムの製造方法

Publications (1)

Publication Number Publication Date
JPH05255250A true JPH05255250A (ja) 1993-10-05

Family

ID=27413179

Family Applications (1)

Application Number Title Priority Date Filing Date
JP3274949A Pending JPH05255250A (ja) 1983-03-08 1991-09-27 新規第四級アミンチオール化合物

Country Status (31)

Country Link
JP (1) JPH05255250A (xx)
KR (1) KR900002247B1 (xx)
AR (1) AR241016A1 (xx)
AT (1) AT387968B (xx)
AU (2) AU572124B2 (xx)
CA (1) CA1284324C (xx)
CH (1) CH658248A5 (xx)
CY (1) CY1546A (xx)
DD (1) DD228258A5 (xx)
DE (1) DE3408347A1 (xx)
DK (1) DK140584A (xx)
ES (2) ES530337A0 (xx)
FI (1) FI840863A (xx)
FR (1) FR2542316B1 (xx)
GB (1) GB2136802B (xx)
GR (1) GR81871B (xx)
HK (1) HK82990A (xx)
HU (1) HU193895B (xx)
IE (1) IE57098B1 (xx)
IL (1) IL71149A (xx)
IT (1) IT1178465B (xx)
LU (1) LU85241A1 (xx)
NL (1) NL8400702A (xx)
NO (1) NO166038C (xx)
NZ (1) NZ207346A (xx)
OA (1) OA07674A (xx)
PT (1) PT78211B (xx)
SE (2) SE8401278L (xx)
SG (1) SG35490G (xx)
YU (2) YU46147B (xx)
ZW (1) ZW3884A1 (xx)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7842689B2 (en) 2003-06-12 2010-11-30 Btg International Limited Cyclic hydroxylamine as psychoactive compounds
JP2015193663A (ja) * 2007-09-24 2015-11-05 ロレアル 少なくとも１種の無色ジスルフィド／チオール前駆体を含む染料組成物、およびこの組成物を使用する染色方法

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4683301A (en) * 1982-04-08 1987-07-28 Bristol-Myers Company Carbapenem antibiotics
US4552696A (en) * 1982-04-09 1985-11-12 Bristol-Myers Company Carbapenem antibiotics
CA1285940C (en) * 1984-07-02 1991-07-09 Merck & Co., Inc. Carbapenems having a 2-quaternary heteroarylalkylthio substituent
IE851586L (en) * 1984-07-02 1986-01-02 Interchem Internat S A I methylcarbapenems having a 2-quaternary¹heteroarylalkylthio substituent
US4665169A (en) * 1985-09-11 1987-05-12 Bristol-Myers Company Carbapenem antibiotics
US4880922A (en) * 1985-11-22 1989-11-14 Bristol-Myers Company Carbapenems with quaternized heterothioalkylthio substitution at position 2
NZ219892A (en) * 1986-04-15 1991-02-26 Merck & Co Inc N-amino quaternised heteroarylium carbapenem derivatives and pharmaceutical compositions thereof
IE910606A1 (en) * 1990-02-23 1991-08-28 Sankyo Co Carbapenem derivatives having antibiotic activity, their¹preparation and their use
US5712267A (en) * 1991-06-04 1998-01-27 Sankyo Company,. Limited Carbapenem derivatives, their preparation and their use as antibiotics

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55147284A (en) * 1979-04-17 1980-11-17 Sanraku Inc Novel beta-lactam derivative and its preparation
IE52147B1 (en) * 1980-03-27 1987-07-08 Merck & Co Inc 4-(3-carboxy-2-oxopropyl)-azetidin-2-ones and process for their preparation
EP0038869A1 (en) * 1980-04-30 1981-11-04 Merck & Co. Inc. Process for the preparation of 1-carbapenems, and intermediates for their preparation
EP0060612A1 (en) * 1981-02-04 1982-09-22 Beecham Group Plc Process for the preparation of azabicyclo(3.2.0)-hept-2-ene derivatives
US4552873A (en) * 1981-08-19 1985-11-12 Sankyo Company Limited Carbapenem compounds, and compositions containing them
EP0074599A1 (en) * 1981-09-09 1983-03-23 Takeda Chemical Industries, Ltd. 5,6-cis-Carbapenem derivatives, their production and use
US4552696A (en) * 1982-04-09 1985-11-12 Bristol-Myers Company Carbapenem antibiotics
US4536335A (en) * 1982-06-18 1985-08-20 Bristol-Myers Company Carbapenem antibiotics

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ADV.BIOL.SKIN=1967 *
SYNTHESIS=1982 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7842689B2 (en) 2003-06-12 2010-11-30 Btg International Limited Cyclic hydroxylamine as psychoactive compounds
US7842690B2 (en) 2003-06-12 2010-11-30 Btg International Limited Cyclic hydroxylamine as psychoactive compounds
US8053432B2 (en) 2003-06-12 2011-11-08 Btg International Limited Cyclic hydroxylamine as psychoactive compounds
JP2015193663A (ja) * 2007-09-24 2015-11-05 ロレアル 少なくとも１種の無色ジスルフィド／チオール前駆体を含む染料組成物、およびこの組成物を使用する染色方法
JP2017203044A (ja) * 2007-09-24 2017-11-16 ロレアル 少なくとも１種の無色ジスルフィド／チオール前駆体を含む染料組成物、およびこの組成物を使用する染色方法

Also Published As

Publication number Publication date
GR81871B (xx) 1984-12-12
FR2542316B1 (fr) 1988-10-07
HU193895B (en) 1987-12-28
SG35490G (en) 1990-07-13
LU85241A1 (fr) 1984-11-14
FI840863A0 (fi) 1984-03-05
SE8401278L (sv) 1984-09-09
NL8400702A (nl) 1984-10-01
AR241016A2 (es) 1991-04-30
IL71149A0 (en) 1984-06-29
FR2542316A1 (fr) 1984-09-14
FI840863A (fi) 1984-09-09
KR840008157A (ko) 1984-12-13
CY1546A (en) 1991-03-22
SE8401278D0 (sv) 1984-03-07
NO840865L (no) 1984-09-10
ES8505205A1 (es) 1985-05-16
HUT34980A (en) 1985-05-28
NZ207346A (en) 1987-01-23
DE3408347A1 (de) 1984-09-13
GB2136802B (en) 1987-05-20
AT387968B (de) 1989-04-10
YU46305B (sh) 1993-05-28
ES530337A0 (es) 1985-05-16
YU46147B (sh) 1993-05-28
PT78211B (en) 1986-08-12
ES8507145A1 (es) 1985-08-16
ES537349A0 (es) 1985-08-16
IE57098B1 (en) 1992-04-22
IT1178465B (it) 1987-09-09
AU7592487A (en) 1987-10-22
ATA76984A (de) 1988-09-15
AU605491B2 (en) 1991-01-17
NO166038B (no) 1991-02-11
CH658248A5 (de) 1986-10-31
SE8901162D0 (sv) 1989-04-03
NO166038C (no) 1991-05-22
AU572124B2 (en) 1988-05-05
AU2536084A (en) 1984-09-13
IT8419945A0 (it) 1984-03-07
DK140584A (da) 1984-09-09
IE840549L (en) 1984-09-08
SE8901162L (sv) 1989-04-03
PT78211A (en) 1984-04-01
CA1284324C (en) 1991-05-21
DK140584D0 (da) 1984-02-29
IL71149A (en) 1990-03-19
GB2136802A (en) 1984-09-26
YU42084A (en) 1986-08-31
ZW3884A1 (en) 1984-10-10
OA07674A (fr) 1985-05-23
HK82990A (en) 1990-10-19
KR900002247B1 (ko) 1990-04-07
GB8405984D0 (en) 1984-04-11
YU49486A (en) 1987-12-31
AR241016A1 (es) 1991-04-30
DD228258A5 (de) 1985-10-09

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