ES444437A1 - Phenylalkylamines - Google Patents

Phenylalkylamines

Info

Publication number
ES444437A1
ES444437A1 ES444437A ES444437A ES444437A1 ES 444437 A1 ES444437 A1 ES 444437A1 ES 444437 A ES444437 A ES 444437A ES 444437 A ES444437 A ES 444437A ES 444437 A1 ES444437 A1 ES 444437A1
Authority
ES
Spain
Prior art keywords
see formula
compound
formula
see
lower alkyl
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
ES444437A
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.)
STWB Inc
Original Assignee
Sterling Drug 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
Priority claimed from US05/641,511 external-priority patent/US4069256A/en
Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of ES444437A1 publication Critical patent/ES444437A1/en
Expired legal-status Critical Current

Links

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
    • C07D213/06—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
    • 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
    • C07D207/06—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 radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • 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
    • C07D207/20—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
    • C07D211/08—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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/12—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
    • 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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • 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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/16—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
    • 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
    • C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic 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
    • C07D295/10—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 doubly bound oxygen or sulphur atoms
    • C07D295/112—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic 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
    • C07D295/135—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
    • 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

A procedure for preparing phenylalkyl amines having the formula I **(See formula)** wherein R1 represents hydrogen or one to two, either the same or different, from among lower alkyl, hydroxy, lower alkoxy, trifluoromethyl, lower alkylmercapto, lower alkylsulfinyl, lower alkylsulfonyl or halogen groups, selected from fluorine, chlorine and bromine; R2 represents hydrogen, or a lower alkoxy or hydroxy group at position 4, or lower alkyl at any of positions 2, 4, 5 or 6; R3 represents hydrogen or lower alkyl; the group (see formula) represents (see formula), (in which R3 is only hydrogen or methyl in the latter case); and N = B represents one of the groups **(See formula)** wherein R3 represents hydrogen or lower alkyl and is the same or different when it occurs more than once, R4 and R5 each represent lower alkyl; R6 and R7 each represent hydrogen, a lower alkyl, cyclohexyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl or benzyl group; Z represents O, S, or N-R8; R8 represents a lower alkyl or cyclohexyl group; and n is the integer 1, 2 or 3, or an acid addition salt thereof, characterized by: a) preparing a compound in which (see formula) represents (see formula) and R3 is H by reducing with an alkali metal hydride a corresponding compound having the formula V **(See formula)** or prepare a compound in which (see formula) represents (see formula) oxidizing the group (see formula) and the compound obtained by cetalizing the group (see formula) of the compound of formula V before the reduction step and then decetalize after the reduction step; b) preparing a compound in which (see formula) represents (see formula) and R2 represents a hydroxy or lower alkoxy group at position 4 reacting, in the presence of a Lewis acid, a compound having formula VI **(See formula)** with a compound having formula VII **(See formula)** where Hal represents halogen; c) preparing a compound in which (see formula) represents (see formula) reacting a compound of formula VIII **(See formula)** wherein Ts represents the p-toluenesulfonyl group, with an amine of the formula H-N = B in the presence of an acid acceptor; or d) preparing a compound in which (see formula) represents (see formula) reacting a compound of formula IXa **(See formula)** with a compound of the formula XX, XXI or XXII **(See formula)** where a compound of Formula I is produced where (see formula) is (see formula) (from XX); (see formula) (from XXI) (see formula) where R is lower alkyl (from XXII) respectively; and, if desired, reducing a compound obtained in which (see formula) is (see formula) to obtain the corresponding compound in which (see formula) is (see formula); and, if you want to obtain a compound in which (see formula) is (see formula), reduce with hydrogen on a catalyst in the presence of perchloric acid, a compound obtained in which (see formula) is (see formula); and, if desired, obtain a compound in which (see formula) is (see formula) reacting, with hydroxylamine, a compound obtained in which (see formula) is (see formula) and, if desired, obtain a compound in which (see formula) is (see formula) reducing a compound obtained in which (see formula) is (see formula) with sodium in a lower alkanol to obtain a compound in which both R3 in the radical are hydrogens, and, if desired, methylate the compound obtained to prepare the corresponding compound in which each of the R3 is methyl ; and, if desired, obtain a compound in which (see formula) represents (see formula) dehydrating a compound obtained where (see formula) is (see formula); and, if desired, converting a obtained free base to an acid addition salt thereof. (Machine-translation by Google Translate, not legally binding)
ES444437A 1975-01-20 1976-01-19 Phenylalkylamines Expired ES444437A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US54255375A 1975-01-20 1975-01-20
US05/641,511 US4069256A (en) 1975-01-20 1975-12-17 Anti-inflammatory phenyl-lower-alkylamines

Publications (1)

Publication Number Publication Date
ES444437A1 true ES444437A1 (en) 1977-10-01

Family

ID=27067067

Family Applications (2)

Application Number Title Priority Date Filing Date
ES444437A Expired ES444437A1 (en) 1975-01-20 1976-01-19 Phenylalkylamines
ES458807A Expired ES458807A1 (en) 1975-01-20 1977-05-14 Phenylalkylamines

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES458807A Expired ES458807A1 (en) 1975-01-20 1977-05-14 Phenylalkylamines

Country Status (18)

Country Link
JP (1) JPS51125364A (en)
AR (1) AR221467A1 (en)
AT (1) AT354454B (en)
AU (1) AU503063B2 (en)
CA (1) CA1053251A (en)
CH (4) CH612920A5 (en)
DE (1) DE2601923A1 (en)
DK (1) DK19176A (en)
ES (2) ES444437A1 (en)
FI (1) FI760112A (en)
FR (2) FR2297614A1 (en)
GB (2) GB1508392A (en)
IL (2) IL48863A (en)
MX (1) MX3819E (en)
NL (1) NL7600566A (en)
NO (3) NO142907C (en)
PT (1) PT64718B (en)
SE (2) SE7600505L (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4308382A (en) * 1975-01-20 1981-12-29 Sterling Drug Inc. 4-[[3-[α-Aminobenzyl]phenyl]methyl]morpholine and 4-[-[3-benzoylphenyl]ethyl]morpholine
US4339576A (en) 1980-11-19 1982-07-13 Sterling Drug Inc. Anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory 1-[(benzoylphenyl)-lower-alkyl]piperidines and analogs thereof
EP0052311A1 (en) * 1980-11-19 1982-05-26 Sterling Drug Inc. 1-((Benzoylphenyl) - lower-alkyl) piperidines and carbinol analogs and preparation thereof
US4396765A (en) 1981-08-24 1983-08-02 Sterling Drug Inc. Amino-1-[(halophenyl)-lower-alkyl]piperidines
US6495580B1 (en) 1998-01-29 2002-12-17 Viropharma Incorporated Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
NZ505894A (en) * 1998-01-29 2002-12-20 Viropharma Inc Methylenebisbenzaldehyde derivatives, methylidynetrisphenol derivative and pharmaceuticals thereof; useful for treating or preventing pneumovirus infection and associated diseases
EP1539691A2 (en) 2002-08-09 2005-06-15 Viropharma Incorporated Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
CA2495266A1 (en) 2002-08-09 2004-02-19 Viropharma Incorporated Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases

Also Published As

Publication number Publication date
NL7600566A (en) 1976-07-22
ES458807A1 (en) 1978-03-01
FI760112A (en) 1976-07-21
GB1508392A (en) 1978-04-26
CH619924A5 (en) 1980-10-31
FR2297614B1 (en) 1979-07-20
JPS51125364A (en) 1976-11-01
DK19176A (en) 1976-07-21
IL48863A (en) 1979-11-30
PT64718B (en) 1977-06-03
NO760169L (en) 1976-07-21
AU1047876A (en) 1977-07-28
SE7910737L (en) 1979-12-28
CH618677A5 (en) 1980-08-15
CH619923A5 (en) 1980-10-31
MX3819E (en) 1981-07-30
NO143902C (en) 1981-05-06
FR2320294A1 (en) 1977-03-04
FR2320294B1 (en) 1980-09-19
ATA304378A (en) 1979-06-15
NO142907B (en) 1980-08-04
NO142907C (en) 1980-11-12
FR2297614A1 (en) 1976-08-13
NO793447L (en) 1976-07-21
NO143902B (en) 1981-01-26
AT354454B (en) 1979-01-10
SE7600505L (en) 1976-09-02
NO793473L (en) 1976-07-21
CA1053251A (en) 1979-04-24
AR221467A1 (en) 1981-02-13
GB1508391A (en) 1978-04-26
DE2601923A1 (en) 1976-07-22
IL55523A0 (en) 1978-12-17
IL48863A0 (en) 1976-03-31
PT64718A (en) 1976-02-01
AU503063B2 (en) 1979-08-23
CH612920A5 (en) 1979-08-31

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