HK26788A - Guanidine derivatives and pharmaceutical compositions containing them - Google Patents

Guanidine derivatives and pharmaceutical compositions containing them

Info

Publication number
HK26788A
HK26788A HK267/88A HK26788A HK26788A HK 26788 A HK26788 A HK 26788A HK 267/88 A HK267/88 A HK 267/88A HK 26788 A HK26788 A HK 26788A HK 26788 A HK26788 A HK 26788A
Authority
HK
Hong Kong
Prior art keywords
alkyl
guanidine
hydrogen
methoxycarbonyl
compounds
Prior art date
Application number
HK267/88A
Other languages
English (en)
French (fr)
Inventor
Mohammad Mehdi Nafissi-Varchei
Original Assignee
Schering Corporation
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 Schering Corporation filed Critical Schering Corporation
Publication of HK26788A publication Critical patent/HK26788A/en

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Classifications

    • 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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • 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
    • C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—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 no 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
    • C07D211/56—Nitrogen atoms
    • 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
    • C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—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 no 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • 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
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • 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
    • C07D295/12—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 or doubly bound nitrogen atoms
    • C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen 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
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Quick-Acting Or Multi-Walled Pipe Joints (AREA)

Claims (10)

1. Verbindungen der allgemeinen Formel deren Isomere an den Guanidin-Gruppen sowie pharmazeutisch unbedenkliche Salze solcher Verbindungen, worin
R6 C1-6-Alkyl oder durch C1-6-Alkoxy, Hydroxy oder Amino substituiertes C1-6-Alkyl ist,
einer der Bausteine X und Y CR5 ist und der andere CH oder N ist,
R1 Wasserstoff, Halogen, Nitro, Amino, NHCOR8 oder NHSO2R8 ist,
R2 und R3 unabhängig voneinander ausgewählt sind aus Wasserstoff, N-Alkylpiperidyl (worin die Alkyl-Gruppe 1 bis 4 Kohlenstoff-Atome hat), Tetrahydropyranyl, Morpholinyl, Piperidyl und C1- bis C6-Alkyl substituiert durch einen oder mehrere Substituenten ausgewählt aus OH, SCH3, OSO3H, SO3H, COR9, COOR10, Piperazinyl, Pyridyl und ist, mit der Maßgabe, daß R2 und R3 nicht beide Wasserstoff sein können,
einer der Substituenten R4 und R5 ausgewählt ist aus Wasserstoff, C1- bis C6-Alkyl und C1- bis C6-Alkoxy und der andere ausgewählt ist aus Wasserstoff, C1- bis C6-Alkyl und R14Z, worin R14 C1- bis C6-Alkyl oder Phenyl ist und Z, O, S, SOn oder SO2NR15 bezeichnet, wobei n 1, oder 3 ist und R15 Wasserstoff oder C1- bis C6-Alkyl ist, wobei in den vorstehenden Definitionen
R8 C1- bis C6-Alkyl, durch Phenyl oder Halogen substituiertes C1- bis C6-Alkyl, Phenyl oder durch C1- bis C6-Alkyl oder Halogen substituiertes Phenyl ist,
R9 C1- bis C6-Alkyl, C1-bis C6-Acyl oder ein Peptid-Rest mit bis zu drei Aminosäuren ist,
R10 Wasserstoff oder C1- bis C6-Alkyl ist,
R12 und R13 unabhängig voneinander ausgewählt sind aus Wasserstoff, C1- bis C6-Alkyl, worin R11C1- bis C6-Alkyl ist.
2. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß R4 Wasserstoff ist, X CR5 ist und Y CH oder N ist.
3. Verbindungen nach Anspruch 2, dadurch gekennzeichnet, daß R1 ausgewählt ist aus NO2, NH2 und NHCOR".
4. Verbindungen nach Anspruch 3, dadurch gekennzeichnet, daß R2 Wasserstoff ist, R3 eine substituierte C1- bis C6-Alkyl-Gruppe bezeichnet und R5 R14Z ist.
5. Verbindungen nach Anspruch 4, dadurch gekennzeichnet, daß R3 eine C1- bis C6-Alkyl-Gruppe bezeichnet, die durch COOR10, Piperazinyl, Pyridyl, SO3H oder OSO3H substituiert ist.
6. Verbindungen nach Anspruch 5 mit der Formel in der
R1 NO2, NH2 oder NHCOCH3 ist und
R3 C1- bis C3-Alkyl ist, das durch einen Substituenten ausgewählt aus Piperazinyl, COOH, Diethylamino, SO3H und OSO3H substituiert ist.
7. Verbindungen nach Anspruch 6, nämlich
N-Methoxycarbonyl-N'-(2-nitro-5-propylthiophenyl)-N"-[2-(N-piperazinyl)ethyl]guanidin,
N-Methoxycarbonyl-N'-[2-(N'-cyano-N"-methylguanidino)ethyl]-N"-(2-nitro-5-propylthiophenyl)guanidin,
N-Methoxycarbonyl-N'-(2-nitro-5-propylthiophenyl)-N"-(2-diethyl-aminoethyl)guanidin,
N-Methoxycarbonyl-N'-(2-nitro-5-propylthiophenyl)-N"-(2-carboxyethyl)guanidin,
N-Methoxycarbonyl-N'-[2-(N'-cyano-N"-methylguanidino)ethyl]-N"-(2-amino-5-propylthiophenyl)guanidin,
N-Methoxycarbonyl-N'-[2-(N'-cyano-N"-methylguanidino)ethyl]-N"-(2-acetamido-5-propylthiophenyl)guanidin,
N-Methoxycarbonyl-N'-(3-carboxypropyl)-N"-(2-nitro-5-propylthiophenyl)guanidin und
N-Methoxycarbonyl-N'-carboxymethyl-N"-(2-nitro-5-propylthiophenyl)guanidin-Natrium-Salz.
8. Pharmazeutische Zusammensetzungen, enthaltend als Wirkstoff eine Verbindung nach irgendeinem der Ansprüche 1 bis 7.
9. Verfahren zur Herstellung von Verbindungen der Formel I nach Anspruch 1, dadurch gekennzeichnet, daß ein Isothioharnstoff der Formel III mit einem Amin der Formel IV umgesetzt wird, wobei in den Formeln R1, R2, R3, R4, R6, X und Y die in Anspruch 1 angegebenen Bedeutungen haben, gewünschtenfalls gefolgt von der Überführung in ein Salz.
10. Verfahren zur Herstellung von pharmazeutischen Zusammensetzungen nach Anspruch 8, dadurch gekennzeichnet, daß eine Verbindung nach irgendeinem der Ansprüche 1 bis 7 in eine für die pharmazeutische Anwendung geeignete Form gebracht wird.
HK267/88A 1980-10-20 1988-04-14 Guanidine derivatives and pharmaceutical compositions containing them HK26788A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/198,424 US4348406A (en) 1980-10-20 1980-10-20 Novel guanidine derivatives

Publications (1)

Publication Number Publication Date
HK26788A true HK26788A (en) 1988-04-22

Family

ID=22733331

Family Applications (1)

Application Number Title Priority Date Filing Date
HK267/88A HK26788A (en) 1980-10-20 1988-04-14 Guanidine derivatives and pharmaceutical compositions containing them

Country Status (20)

Country Link
US (3) US4348406A (de)
EP (2) EP0050286B1 (de)
JP (2) JPH0323540B2 (de)
AT (1) ATE13423T1 (de)
AU (1) AU548628B2 (de)
CA (1) CA1248949A (de)
CY (1) CY1424A (de)
DE (1) DE3170623D1 (de)
DK (1) DK255682A (de)
ES (1) ES8206455A1 (de)
HK (1) HK26788A (de)
HU (1) HU183749B (de)
IE (1) IE51871B1 (de)
IL (1) IL64081A (de)
MY (1) MY8700682A (de)
NZ (1) NZ198679A (de)
PT (1) PT73841B (de)
SG (1) SG112187G (de)
WO (1) WO1982001367A1 (de)
ZA (1) ZA817265B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4701447A (en) * 1983-09-23 1987-10-20 Schering Corporation N-((2-nitro)phenyl)-N' (organic acid) guanidine anthelmintics
EP0156889A1 (de) * 1983-09-23 1985-10-09 Schering Corporation Phenylguanidine
US4723029A (en) * 1983-09-23 1988-02-02 Schering Corporation Organic acid-substituted guanidine anthelmintics
AT401086B (de) * 1985-11-28 1996-06-25 Gossler Ewald Verfahren zum verdichten von gasen
GB8903592D0 (en) * 1989-02-16 1989-04-05 Boots Co Plc Therapeutic agents
HU205343B (en) * 1989-06-21 1992-04-28 Chinoin Gyogyszer Es Vegyeszet New process for producing guanidine derivatives
GB9915709D0 (en) 1999-07-05 1999-09-08 Guilden Ltd Vehicle suspension systems
JP5227795B2 (ja) * 2005-07-28 2013-07-03 インターベツト・インターナシヨナル・ベー・ベー 抗寄生虫活性を有する新規ベンゾイミダゾール（チオ）カルバメートおよびその合成
WO2007144362A1 (en) 2006-06-14 2007-12-21 Intervet International B.V. A suspension comprising benzimidazole carbamate and a polysorbate
EP2032046B1 (de) * 2006-06-12 2015-11-04 Smith & Nephew, Inc. Systeme und vorrichtungen zur schienbeingeweberesektion

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL38933A0 (en) * 1971-03-17 1972-05-30 Ciba Geigy Ag New carbamates,their manufacture and their use in plant protection
US4097673A (en) * 1974-11-01 1978-06-27 E. I. Du Pont De Nemours And Company Herbicidal carbamates and thiolcarbamates
US3941824A (en) * 1973-05-02 1976-03-02 E. I. Du Pont De Nemours & Co. Herbicidal carbamates and thiolcarbamates
AR213309A1 (es) * 1976-05-05 1979-01-15 Rohm & Haas Procedimiento para preparar 2-amino-isotioureidobencenos substituidos
DE2651467A1 (de) * 1976-11-11 1978-05-18 Bayer Ag Substituierte o-phenylendiaminderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
US4293569A (en) * 1978-05-12 1981-10-06 E. R. Squibb & Sons, Inc. Substituted phenylguanindines and method
DE2836385A1 (de) 1978-08-19 1980-03-06 Hoechst Ag Monocarboxylate von phenylguanidinsulfonsaeureestern, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US4217358A (en) 1979-04-18 1980-08-12 E. R. Squibb & Sons, Inc. Substituted phenylguanidines and method

Also Published As

Publication number Publication date
JPH0323540B2 (de) 1991-03-29
HU183749B (en) 1984-05-28
US4406893A (en) 1983-09-27
CY1424A (en) 1988-09-02
NZ198679A (en) 1985-02-28
IE812453L (en) 1982-04-20
IE51871B1 (en) 1987-04-15
DE3170623D1 (en) 1985-06-27
US4435398A (en) 1984-03-06
MY8700682A (en) 1987-12-31
IL64081A0 (en) 1982-01-31
PT73841B (en) 1983-11-07
EP0050286A3 (en) 1982-05-26
EP0050286B1 (de) 1985-05-22
WO1982001367A1 (en) 1982-04-29
ATE13423T1 (de) 1985-06-15
SG112187G (en) 1988-05-20
DK255682A (da) 1982-06-07
ES506337A0 (es) 1982-08-16
EP0050286A2 (de) 1982-04-28
ES8206455A1 (es) 1982-08-16
JPH03264527A (ja) 1991-11-25
IL64081A (en) 1985-12-31
US4348406A (en) 1982-09-07
PT73841A (en) 1981-11-01
AU7809281A (en) 1982-05-11
EP0063158A1 (de) 1982-10-27
JPH0432051B2 (de) 1992-05-28
AU548628B2 (en) 1985-12-19
ZA817265B (en) 1982-09-29
JPS57501850A (de) 1982-10-14
CA1248949A (en) 1989-01-17

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PC Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee)