NL186633C - Werkwijze voor de bereiding van een geneesmiddel met anti-aritmische werking en werkwijze voor de bereiding van daarin toegepaste benzamidederivaten. - Google Patents

Werkwijze voor de bereiding van een geneesmiddel met anti-aritmische werking en werkwijze voor de bereiding van daarin toegepaste benzamidederivaten.

Info

Publication number
NL186633C
NL186633C NLAANVRAGE7503389,A NL7503389A NL186633C NL 186633 C NL186633 C NL 186633C NL 7503389 A NL7503389 A NL 7503389A NL 186633 C NL186633 C NL 186633C
Authority
NL
Netherlands
Prior art keywords
preparation
arrhythic
effect
medicinal product
derivatives used
Prior art date
Application number
NLAANVRAGE7503389,A
Other languages
English (en)
Dutch (nl)
Other versions
NL7503389A (nl
NL186633B (nl
Original Assignee
Riker Laboratories Inc
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 Riker Laboratories Inc filed Critical Riker Laboratories Inc
Publication of NL7503389A publication Critical patent/NL7503389A/xx
Publication of NL186633B publication Critical patent/NL186633B/xx
Application granted granted Critical
Publication of NL186633C publication Critical patent/NL186633C/xx

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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
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—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 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
NLAANVRAGE7503389,A 1974-04-01 1975-03-21 Werkwijze voor de bereiding van een geneesmiddel met anti-aritmische werking en werkwijze voor de bereiding van daarin toegepaste benzamidederivaten. NL186633C (nl)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US457099A US3900481A (en) 1974-04-01 1974-04-01 Derivatives of pyrrolidine and piperidine

Publications (3)

Publication Number Publication Date
NL7503389A NL7503389A (nl) 1975-10-03
NL186633B NL186633B (nl) 1990-08-16
NL186633C true NL186633C (nl) 1991-01-16

Family

ID=23815433

Family Applications (1)

Application Number Title Priority Date Filing Date
NLAANVRAGE7503389,A NL186633C (nl) 1974-04-01 1975-03-21 Werkwijze voor de bereiding van een geneesmiddel met anti-aritmische werking en werkwijze voor de bereiding van daarin toegepaste benzamidederivaten.

Country Status (22)

Country Link
US (1) US3900481A (enExample)
JP (2) JPS5827268B2 (enExample)
AR (1) AR210990A1 (enExample)
BE (1) BE827354A (enExample)
CA (1) CA1054602A (enExample)
CH (1) CH618425A5 (enExample)
CS (1) CS209846B2 (enExample)
DE (1) DE2513916C2 (enExample)
DK (1) DK158980C (enExample)
ES (1) ES435870A1 (enExample)
FR (1) FR2265366B1 (enExample)
GB (1) GB1508015A (enExample)
HU (1) HU169762B (enExample)
IE (1) IE41224B1 (enExample)
IL (1) IL46967A (enExample)
NL (1) NL186633C (enExample)
NO (1) NO144262C (enExample)
OA (1) OA04912A (enExample)
PL (1) PL95576B1 (enExample)
SE (1) SE391336B (enExample)
SU (1) SU668599A3 (enExample)
ZA (1) ZA751040B (enExample)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1520584A (en) * 1975-04-02 1978-08-09 Yamanouchi Pharma Co Ltd 2 - alkoxy - 5 substituted benzamide derivatives and their use in pharmaceutical compositions
US4197243A (en) * 1975-04-02 1980-04-08 Yamanouchi Pharmaceutical Co., Ltd. N-1-Benzyl-3-pyrrolidinyl-4-dimethylamino benzamide derivatives
NL7611713A (nl) * 1975-11-03 1977-05-05 Thomae Gmbh Dr K Werkwijze voor de bereiding van verbindingen en preparaten met waardevolle farmacologische eigen- schappen.
US4071524A (en) * 1976-11-08 1978-01-31 Riker Laboratories, Inc. Derivatives of urea
US4097481A (en) * 1976-11-08 1978-06-27 Riker Laboratories, Inc. Tertiary amide derivatives of pyrrolidine and piperidine
US4642384A (en) * 1979-03-19 1987-02-10 Riker Laboratories, Inc. Process for the preparation of derivatives of pyrrolidine and piperidine
US4684733A (en) * 1979-03-19 1987-08-04 Riker Laboratories, Inc. Process for the preparation of intermediates of derivatives of pyrrolidine and piperidine
ZA801565B (en) * 1979-03-19 1981-05-27 Riker Laboratories Inc Process for the preparation of 2,5-bis(2,2,2-trifluoroethoxy)-n-(2-piperidylmethyl)benzamide
GB2097000B (en) * 1979-03-19 1983-11-30 Riker Laboratories Inc Process for the preparation of 1,4-bis(2,2,2-trifluoroethoxy) benzene
US4617396A (en) * 1979-03-19 1986-10-14 Riker Laboratories, Inc. Process for the preparation of derivatives of piperidine
US4390716A (en) * 1981-06-08 1983-06-28 Riker Laboratories, Inc. Phenolic derivative
US4339587A (en) * 1981-06-08 1982-07-13 Riker Laboratories, Inc. 5-Benzyloxy or 5-hydroxy-2-(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide
US4452983A (en) * 1981-06-08 1984-06-05 Riker Laboratories, Inc. Phenolic derivative
JPS5970666A (ja) * 1982-10-15 1984-04-21 Kyowa Hakko Kogyo Co Ltd １，４−ジヒドロピリジン誘導体
US4656285A (en) * 1983-11-15 1987-04-07 Riker Laboratories, Inc. Compound 2-acetamidomethyl-6-methoxy-pyridine
US4496734A (en) * 1983-11-15 1985-01-29 Riker Laboratories, Inc. Metabolite
US4555573A (en) * 1983-11-15 1985-11-26 Riker Laboratories, Inc. Certain 6-benzamidomethyl-2(1H)-pyridone derivatives
US4497954A (en) * 1983-11-15 1985-02-05 Riker Laboratories, Inc. Cyclopentanone derivatives
US4599434A (en) * 1983-11-15 1986-07-08 Riker Laboratories, Inc. Cyclopentanone derivatives
US5336622A (en) * 1986-04-25 1994-08-09 Abbott Laboratories Tracers for use in flecainide fluorescence polarization immunoassay
NZ219913A (en) * 1986-04-25 1990-08-28 Riker Laboratories Inc Various flecainide derivatives and antibodies raised thereto
DE3786037T2 (de) * 1986-04-25 1993-11-25 Abbott Lab Tracer zur Benutzung in immunologischen Fluoreszenz-Polarisationsverfahren zum Nachweis von Flecainid.
US4952574A (en) * 1988-09-26 1990-08-28 Riker Laboratories, Inc. Antiarrhythmic substituted N-(2-piperidylmethyl)benzamides
US4938966A (en) * 1988-11-30 1990-07-03 Riker Laboratories, Inc. Controlled release flecainide acetate formulation
US5254569A (en) * 1991-01-14 1993-10-19 The Du Pont Merck Pharmaceutical Company (Amidomethyl)nitrogen heterocyclic analgesics
IL121288A (en) * 1997-07-11 2000-10-31 Finetech Ltd Process and a novel intermediate for the preparation of flecainide
ITMI20011772A1 (it) * 2001-08-10 2003-02-10 A M S A Anonima Materie Sint E Processo per la preparazione della 2,5-bis-(2,2,2-trifluoroetossi)-n-(2-piperidilmetil)-benzamide(flecainide)
EP1500651A1 (en) * 2003-07-25 2005-01-26 Bayer CropScience S.A. N-[2-(2-Pyridinyl)ethyl]benzamide compounds and their use as fungicides
US7196197B2 (en) * 2003-09-17 2007-03-27 Apotex Pharmachem Inc. Process for the preparation of Flecainide, its pharmaceutically acceptable salts and important intermediates thereof
EP1918280A1 (en) * 2006-11-06 2008-05-07 "Joint Stock Company Grindeks" Process for the preparation of 2,5-bis-(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide and salts thereof
KR20090082507A (ko) 2006-11-20 2009-07-30 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 통증 및 소양증 치료용 방법, 조성물 및 키트
JP4946482B2 (ja) 2007-02-08 2012-06-06 船井電機株式会社 緩衝用梱包材及びｔｖ受像機の緩衝用梱包材
WO2011006073A1 (en) 2009-07-10 2011-01-13 President And Fellows Of Harvard College Permanently charged sodium and calcium channel blockers as anti-inflammatory agents
US11021443B2 (en) 2015-08-03 2021-06-01 President And Fellows Of Harvard College Charged ion channel blockers and methods for use
US10828287B2 (en) 2019-03-11 2020-11-10 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
CN113811305A (zh) 2019-03-11 2021-12-17 诺西恩医疗公司 带电的离子通道阻滞剂及其使用方法
US10780083B1 (en) 2019-03-11 2020-09-22 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US11377422B2 (en) 2019-03-11 2022-07-05 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
CA3129089A1 (en) 2019-03-11 2020-09-17 Bridget Mccarthy Cole Ester substituted ion channel blockers and methods for use
CA3155568A1 (en) 2019-11-06 2021-05-14 Bridget Mccarthy Cole Charged ion channel blockers and methods for use
AU2020380118B2 (en) 2019-11-06 2026-06-11 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US12162851B2 (en) 2020-03-11 2024-12-10 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US11332446B2 (en) 2020-03-11 2022-05-17 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US20260207488A1 (en) 2022-12-22 2026-07-23 Colonis Pharma Ltd Liquid pharmaceutical composition containing flecainide and process for the preparation thereof

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FR6209M (enExample) * 1967-04-03 1968-07-29
US3719687A (en) * 1970-07-22 1973-03-06 Riker Laboratories Inc N-(2-dialkylaminoalkylene)amides of 1,1-dihydroperfluoroalkoxy-substituted aryl acids and salts thereof
US3655728A (en) * 1970-07-22 1972-04-11 Riker Laboratories Inc N-(2 - dialkylaminoalkylene)-esters of fluoroalkoxy-substituted aryl carboxylic acid and salts thereof

Also Published As

Publication number Publication date
OA04912A (fr) 1980-10-31
NO750976L (enExample) 1975-10-02
GB1508015A (en) 1978-04-19
NL7503389A (nl) 1975-10-03
SE7503262L (enExample) 1975-10-02
DK119675A (enExample) 1975-10-02
NO144262C (no) 1981-07-29
CA1054602A (en) 1979-05-15
IL46967A0 (en) 1975-05-22
CS209846B2 (en) 1981-12-31
IE41224L (en) 1975-10-01
DK158980C (da) 1991-01-07
DE2513916C2 (de) 1982-12-23
US3900481A (en) 1975-08-19
HU169762B (enExample) 1977-02-28
ZA751040B (en) 1976-01-28
FR2265366B1 (enExample) 1980-01-11
JPS50137975A (enExample) 1975-11-01
BE827354A (fr) 1975-09-29
PL95576B1 (pl) 1977-10-31
IE41224B1 (en) 1979-11-21
SU668599A3 (ru) 1979-06-15
FR2265366A1 (enExample) 1975-10-24
DK158980B (da) 1990-08-13
JPS5858347B2 (ja) 1983-12-24
NL186633B (nl) 1990-08-16
AU7957875A (en) 1976-09-30
JPS5827268B2 (ja) 1983-06-08
ES435870A1 (es) 1976-12-16
NO144262B (no) 1981-04-21
CH618425A5 (enExample) 1980-07-31
SE391336B (sv) 1977-02-14
JPS5865268A (ja) 1983-04-18
IL46967A (en) 1978-09-29
DE2513916A1 (de) 1975-10-09
AR210990A1 (es) 1977-10-14

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