CH616676A5 - - Google Patents

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Publication number
CH616676A5
CH616676A5 CH1517477A CH1517477A CH616676A5 CH 616676 A5 CH616676 A5 CH 616676A5 CH 1517477 A CH1517477 A CH 1517477A CH 1517477 A CH1517477 A CH 1517477A CH 616676 A5 CH616676 A5 CH 616676A5
Authority
CH
Switzerland
Prior art keywords
formula
carbon atoms
group
alkyl
hydrogen
Prior art date
Application number
CH1517477A
Other languages
German (de)
English (en)
Inventor
Ernst-Otto Dr Renth
Anton Dr Mentrup
Kurt Dr Schromm
Peter Dr Danneberg
Original Assignee
Boehringer Sohn Ingelheim
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 Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim
Publication of CH616676A5 publication Critical patent/CH616676A5/de

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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • 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
    • 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
    • C07D295/135—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Anesthesiology (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CH1517477A 1972-12-23 1977-12-09 CH616676A5 (el)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2263211A DE2263211A1 (de) 1972-12-23 1972-12-23 Neue arylpiperazine und verfahren zu ihrer herstellung

Publications (1)

Publication Number Publication Date
CH616676A5 true CH616676A5 (el) 1980-04-15

Family

ID=5865328

Family Applications (10)

Application Number Title Priority Date Filing Date
CH1790773A CH605872A5 (el) 1972-12-23 1973-12-20
CH1516777A CH616673A5 (el) 1972-12-23 1977-12-09
CH1517577A CH616677A5 (el) 1972-12-23 1977-12-09
CH1517277A CH616674A5 (el) 1972-12-23 1977-12-09
CH1517177A CH616670A5 (el) 1972-12-23 1977-12-09
CH1517477A CH616676A5 (el) 1972-12-23 1977-12-09
CH1516977A CH616668A5 (el) 1972-12-23 1977-12-09
CH1516877A CH616667A5 (el) 1972-12-23 1977-12-09
CH1517377A CH616675A5 (el) 1972-12-23 1977-12-09
CH1517077A CH616669A5 (el) 1972-12-23 1977-12-09

Family Applications Before (5)

Application Number Title Priority Date Filing Date
CH1790773A CH605872A5 (el) 1972-12-23 1973-12-20
CH1516777A CH616673A5 (el) 1972-12-23 1977-12-09
CH1517577A CH616677A5 (el) 1972-12-23 1977-12-09
CH1517277A CH616674A5 (el) 1972-12-23 1977-12-09
CH1517177A CH616670A5 (el) 1972-12-23 1977-12-09

Family Applications After (4)

Application Number Title Priority Date Filing Date
CH1516977A CH616668A5 (el) 1972-12-23 1977-12-09
CH1516877A CH616667A5 (el) 1972-12-23 1977-12-09
CH1517377A CH616675A5 (el) 1972-12-23 1977-12-09
CH1517077A CH616669A5 (el) 1972-12-23 1977-12-09

Country Status (15)

Country Link
US (1) US3941789A (el)
JP (4) JPS4994688A (el)
AT (1) AT338271B (el)
BE (1) BE809041A (el)
CH (10) CH605872A5 (el)
DE (1) DE2263211A1 (el)
ES (10) ES421751A1 (el)
FI (1) FI59990C (el)
FR (1) FR2211252B1 (el)
GB (1) GB1456253A (el)
IE (1) IE38679B1 (el)
LU (1) LU69064A1 (el)
NL (1) NL7317469A (el)
NO (1) NO140381C (el)
SE (1) SE417516B (el)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4075335A (en) * 1972-08-24 1978-02-21 Ciba-Geigy Corporation Pharmaceutical piperidine derivatives
US4100282A (en) * 1972-12-23 1978-07-11 Boehringer Ingelheim Gmbh N-Aryl-N'-(phenyl- or phenoxy-alkyl)-piperazines and salts thereof
US4038279A (en) * 1972-12-23 1977-07-26 Boehringer Ingelheim Gmbh N-aryl-n'-(phenyl-or phenoxy-alkyl)-piperazines and salts thereof
US4440774A (en) * 1975-03-03 1984-04-03 Merck & Co., Inc. 3-Amino-2-hydroxypropoxyaryl imidazole derivatives
GB1518559A (en) * 1976-04-12 1978-07-19 Science Union & Cie Naphthyl derivatives processes for their preparation an pharmaceutical compositions containing them
US4052399A (en) * 1976-09-13 1977-10-04 Morton-Norwich Products, Inc. 1-[2-(Hexahydro-1H-azepino)ethyl]-2(1H)pyrimidone dihydrochloride
US4052400A (en) * 1976-10-29 1977-10-04 Morton-Norwich Products, Inc. Hypertensive 1-substituted 2(1h)-pyrimidones
DE2960178D1 (en) * 1978-06-06 1981-04-09 Hoechst Ag New substituted phenylpiperazine derivatives, pharmaceutical compositions containing them and process for their preparation
DE2834114A1 (de) * 1978-08-01 1980-02-14 Schering Ag Polyalkoxyphenylpyrrolidone iii, verfahren zu ihrer herstellung und ihre verwendung
DE3005287A1 (de) * 1980-02-13 1981-08-20 Basf Ag, 6700 Ludwigshafen Phenylpiperazinderivate von 1,3,4-oxadiazolylphenolen, ihre herstellung und diese enthaltende therapeutische mittel
DE3101456A1 (de) 1981-01-19 1982-09-02 Basf Ag, 6700 Ludwigshafen Phenylpiperazinyl-propanole von hetarylphenolen, ihre herstellung und diese enthaltende therapeutische mittel
DE3101502A1 (de) * 1981-01-19 1982-08-26 Basf Ag, 6700 Ludwigshafen Phenylpiperazinderivate von hetarylphenolen und hetarylanilinen, ihre hersttellung und diese enthaltendetherapeutische mittel
CH653021A5 (fr) * 1981-04-24 1985-12-13 Delalande Sa Derives piperidino, piperazino et homopiperazino, n-substitues par un groupe heterocyclique aromatique, leur procede de preparation et composition therapeutique les contenant.
US4367335A (en) * 1981-08-03 1983-01-04 Mead Johnson & Company Thiazolidinylalkylene piperazine derivatives
US4450272A (en) * 1982-05-06 1984-05-22 American Cyanamid Company Antiatherosclerotic 1-piperazine-thicarboxamides
US4452798A (en) * 1982-06-22 1984-06-05 Warner-Lambert Company 1-Substituted phenyl-4-alkyl hydantoin piperazine compounds as antihypertensive agents
EP0138754B1 (de) * 1983-08-15 1988-05-25 Ciba-Geigy Ag Photohärtbare Gemische
US4593039A (en) * 1984-04-02 1986-06-03 Merck & Co., Inc. 1-aryloxy-3-(substituted aminoalkylamino)-2-propanols
US4539318A (en) * 1984-06-04 1985-09-03 Merck & Co., Inc. Tertiary aminohydroxypropoxy substituted thiadiazoles, pharmaceutical compositions and use
US4616017A (en) * 1984-06-04 1986-10-07 Merck & Co., Inc. Aminohydroxypropoxy substituted aryl compounds
DE3424685A1 (de) * 1984-07-05 1986-02-06 Beiersdorf Ag, 2000 Hamburg Neue substituierte phenylpiperazinyl-propanole, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen
GB8603120D0 (en) * 1986-02-07 1986-03-12 Pfizer Ltd Anti-dysrhythmia agents
US4732895A (en) * 1986-05-02 1988-03-22 American Cyanamid Company α-[5-methyl-2-(pyridinyl)-1H-imidazol-4-yl]substituted-1-piperazineethanols useful for treating hypertension
EP0288575A4 (en) * 1986-10-27 1990-10-10 Yoshitomi Pharmaceutical Industries, Ltd. Piperazine compounds and their medicinal use
DE3803860A1 (de) * 1988-02-09 1989-08-17 Basf Ag N,n'-disubstituierte piperazine
US5382583A (en) * 1989-04-22 1995-01-17 John Wyeth & Brother, Limited Piperazine derivatives
US5364849A (en) * 1989-04-22 1994-11-15 John Wyeth & Brother, Limited 1-[3 or 4-[1-[4-piperazinyl]]-2 arylpropionyl or butryl]-heterocyclic derivatives
US5166148A (en) * 1990-07-09 1992-11-24 The Du Pont Merck Pharmaceutical Company 2-amino-1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity
SK283420B6 (sk) * 1992-05-08 2003-07-01 Pharmacia & Upjohn Company Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny
DK148392D0 (da) * 1992-12-09 1992-12-09 Lundbeck & Co As H Heterocykliske forbindelser
WO1994018172A1 (en) * 1993-02-01 1994-08-18 Yoshitomi Pharmaceutical Industries, Ltd. Imidazolylbenzene compound and use thereof as medicine
IL114027A (en) 1994-06-08 1999-11-30 Lundbeck & Co As H 4-Phenyl piperazine (piperidine or tetrahydropyridine) derivatives serotinin 5-HT1A and dopamin D2 receptor ligand pharmaceutical compositions containing them
WO1996014297A1 (fr) * 1994-11-04 1996-05-17 Sumitomo Pharmaceuticals Company, Limited Nouveaux derives de lactame
WO1997036893A1 (en) * 1996-03-29 1997-10-09 Duphar International Research B.V. Piperazine and piperidine compounds
JP4349320B2 (ja) 2005-05-12 2009-10-21 パナソニック株式会社 マニピュレータ型ロボット
CA2627234A1 (en) 2005-10-27 2007-05-03 Ucb Pharma, S.A. Compounds comprising a lactam or a lactam derivative moiety, processes for making them, and their uses
US10126380B2 (en) * 2015-06-15 2018-11-13 Norell, Inc. Closure and system for NMR sample containers with a secondary locking seal
CN114634479A (zh) * 2020-12-16 2022-06-17 北京盈科瑞创新药物研究有限公司 一种派嗪衍生物、其制备方法及应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL127797C (el) * 1961-02-08
US3562277A (en) * 1967-09-06 1971-02-09 Shulton Inc Ketonic derivatives of phenyl piperazines
BE788280A (fr) * 1971-09-04 1973-02-28 Pfizer Nouvelles 1-(3-trifluoro-methyl-phenyl)-4-((amido cyclique)- alkyl) piperazines et composition pharmaceutique les contenant

Also Published As

Publication number Publication date
AT338271B (de) 1977-08-10
IE38679L (en) 1974-06-23
GB1456253A (en) 1976-11-24
CH616674A5 (el) 1980-04-15
SE417516B (sv) 1981-03-23
ES444730A1 (es) 1977-05-16
CH616675A5 (el) 1980-04-15
FR2211252A1 (el) 1974-07-19
CH616667A5 (el) 1980-04-15
ES444736A1 (es) 1977-05-16
ES444731A1 (es) 1977-05-16
JPS5976074A (ja) 1984-04-28
US3941789A (en) 1976-03-02
JPS5976067A (ja) 1984-04-28
CH605872A5 (el) 1978-10-13
IE38679B1 (en) 1978-05-10
FI59990B (fi) 1981-07-31
CH616668A5 (el) 1980-04-15
ES444734A1 (es) 1977-05-16
CH616670A5 (el) 1980-04-15
LU69064A1 (el) 1975-08-20
ES444735A1 (es) 1977-05-16
NL7317469A (el) 1974-06-25
AU6397773A (en) 1975-07-03
JPS4994688A (el) 1974-09-09
CH616673A5 (el) 1980-04-15
DE2263211A1 (de) 1974-07-04
ES444732A1 (es) 1977-05-16
ES444738A1 (es) 1977-05-16
ES444737A1 (es) 1977-05-16
FR2211252B1 (el) 1977-01-28
ATA1072773A (de) 1976-12-15
BE809041A (fr) 1974-06-21
CH616669A5 (el) 1980-04-15
CH616677A5 (el) 1980-04-15
NO140381C (no) 1979-08-22
FI59990C (fi) 1981-11-10
ES444733A1 (es) 1977-05-16
NO140381B (no) 1979-05-14
JPS5976070A (ja) 1984-04-28
ES421751A1 (es) 1976-12-16

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Date Code Title Description
PL Patent ceased