IE39098B1 - Polyene derivatives - Google Patents

Polyene derivatives

Info

Publication number
IE39098B1
IE39098B1 IE643/74A IE64374A IE39098B1 IE 39098 B1 IE39098 B1 IE 39098B1 IE 643/74 A IE643/74 A IE 643/74A IE 64374 A IE64374 A IE 64374A IE 39098 B1 IE39098 B1 IE 39098B1
Authority
IE
Ireland
Prior art keywords
amino
lower alkyl
alkenoxy
nitro
mono
Prior art date
Application number
IE643/74A
Other versions
IE39098L (en
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of IE39098L publication Critical patent/IE39098L/en
Publication of IE39098B1 publication Critical patent/IE39098B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
    • C07C317/10—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C07C57/48—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5428—Acyclic unsaturated phosphonium compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1468402 Triarylphosphonium salts F HOFFMANNLA ROCHE & CO AG 29 March 1974 [30 March 1973] Divided out of 1468401 09185/76 Heading C2P The invention comprises triaryl phosphonium salts of the general formula wherein R 1 and R 2 each represent a lower alkyl group, R 3 represents a hydrogen or halogen atom or a lower alkyl, lower alkoxy, lower alkenoxy, nitro, amino, mono(lower alkyl)- amino, di(lower alkyl)amino, lower alkanoylamino or N-heterocyclic group, R 4 represents a lower alkenyl, lower alkoxy, lower alkenoxy, nitro, amino, mono(lower alkyl)amino, di(lower alkyl)amino, lower alkanoylamino or N-heterocyclic group and R 5 represents a hydrogen or halogen atom or a lower alkyl, lower alkenyl, lower alkoxy, lower alkenoxy, nitro, amino, mono(lower alkyl)amino, di(lower alkul)amino, lower alkanoylamino or N-heterocyclic group provided that when R 3 or R 5 is a halogen atom R 4 is other than a lower alkoxy group, m is 0 or 1, X is aryl and Y is the anion of an organic or inorganic acid, the lower alkyl, lower alkenyl, lower alkoxy, lower alkenoxy, and lower alkanoyl groups being defined as those containing up to 6 carbon atoms in each case. The aryl group X includes C 1 -C 6 alkylphenyl and C 1 - C 6 alkoxyphenyl and the preferred anions Y are Cl, Br, I, hydrosulphate and tosyloxy. Specified N-heterocyclic groups are pyrrolidino, piperidino, morpholino and thiamorpholino. The compounds in which m is zero and Y is a halide anion may be obtained by treating a corresponding (R 1 -R 5 )-benzene with formaldehyde in the presence of a hydrohalic acid, e.g. cone. HCI, if desired in a solvent and reacting the resulting (R 1 -R 5 )-benzyl halide with a triaryl phosphine in a solvent. Compounds in which m is 1 and Y is a halide anion can be obtained by reacting a formylating agent with the corresponding (R 1 - R 5 )-benzene, e.g. by reaction with orthoformic acid, formyl chloride or dimethyl formamide in the presence of a Lewis acid, reacting the resulting (R 1 -R 5 )-benzaldehyde with acetone in the presence of alkali to form a 4-(R 1 -R 5 )-phenylbut-3-en-2-one, converting the latter to the corresponding acetylenic alcohol (5-(R 1 -R 5 )- phenyl - 3 - methyl - 3 - hydroxy - penta - 4 - en- 1-yne) by a Grignard reaction with addition of acetylene, partially hydrogenating the acetylenic alcohol to form the corresponding diolefinic alcohol and then converting the latter to a triarylphosphonium salt by treating with a triaryl phosphine in the presence of a hydrohalide, e.g. HCl or HBr, in a solvent, e.g. benzene. The products are useful as intermediates in the production of polyene derivatives having therapeutic properties. (From GB1468402 A) [FR2223037A1]
IE643/74A 1973-03-30 1974-03-25 Polyene derivatives IE39098B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH460373A CH585166A5 (en) 1973-03-30 1973-03-30

Publications (2)

Publication Number Publication Date
IE39098L IE39098L (en) 1974-09-30
IE39098B1 true IE39098B1 (en) 1978-08-02

Family

ID=4279174

Family Applications (1)

Application Number Title Priority Date Filing Date
IE643/74A IE39098B1 (en) 1973-03-30 1974-03-25 Polyene derivatives

Country Status (32)

Country Link
JP (1) JPS5724333B2 (en)
AR (1) AR207004A1 (en)
AT (1) AT340397B (en)
AU (1) AU472475B2 (en)
BE (1) BE813002A (en)
BR (1) BR7402525D0 (en)
CA (1) CA1030975A (en)
CH (4) CH585166A5 (en)
CU (1) CU34050A (en)
DD (1) DD111368A5 (en)
DE (1) DE2414619C2 (en)
DK (1) DK155043C (en)
ES (1) ES424750A1 (en)
FI (1) FI62280C (en)
FR (1) FR2223037B1 (en)
GB (2) GB1468402A (en)
HK (1) HK28780A (en)
HU (1) HU172655B (en)
IE (1) IE39098B1 (en)
IL (1) IL44368A (en)
KE (1) KE3047A (en)
LU (2) LU69733A1 (en)
MX (1) MX152550A (en)
MY (1) MY8100064A (en)
NL (2) NL161429C (en)
NO (2) NO143426C (en)
PH (1) PH13081A (en)
PL (1) PL96105B1 (en)
SE (1) SE419752B (en)
SU (1) SU613718A3 (en)
YU (1) YU40253B (en)
ZA (1) ZA741580B (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH604705A5 (en) * 1974-09-24 1978-09-15 Hoffmann La Roche
CH619437A5 (en) * 1975-08-22 1980-09-30 Hoffmann La Roche Process for the preparation of polyene compounds.
US4335248A (en) 1975-11-14 1982-06-15 Hoffmann-La Roche Inc. Fluorinated polyenes
US4169100A (en) * 1975-11-14 1979-09-25 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4137246A (en) * 1976-09-13 1979-01-30 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4266073A (en) * 1975-11-14 1981-05-05 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4395575A (en) 1975-11-14 1983-07-26 Hoffmann-La Roche, Inc. 5(Halophenyl)-2-fluoro-pentadienals
US4299995A (en) 1979-05-10 1981-11-10 Hoffmann-La Roche Inc. Fluorinated polyenes
CH624373A5 (en) * 1975-11-14 1981-07-31 Hoffmann La Roche Process for the preparation of polyene compounds
US4201727A (en) 1976-11-14 1980-05-06 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4321209A (en) 1975-11-14 1982-03-23 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4338253A (en) 1975-11-14 1982-07-06 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4375563A (en) 1975-11-14 1983-03-01 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
CA1111441A (en) 1976-12-20 1981-10-27 Werner Bollag Polyene compounds
US4200647A (en) * 1977-12-21 1980-04-29 Hoffmann-La Roche Inc. Vitamin A compositions to treat rheumatic disease
US4642318A (en) * 1982-11-17 1987-02-10 Klaus Wolff Method for decreasing radiation load in PUVA therapy
CH661516A5 (en) * 1983-12-08 1987-07-31 Hoffmann La Roche PHENYLNONATETRAENOYL SUGAR DERIVATIVES.
ZA854828B (en) * 1984-07-27 1986-03-26 Hoffmann La Roche Phenyl nonatetraenoic acid derivatives
US5250562A (en) * 1988-02-24 1993-10-05 Hoffmann-La Roche Inc. Stilbene derivatives
JPH10158192A (en) * 1996-10-03 1998-06-16 Eisai Co Ltd Medicine composition for treating graft-versus-host disease (gvhd) and for suppressing graft rejection in organ transplantation
JP4584384B2 (en) * 1999-09-28 2010-11-17 扶桑薬品工業株式会社 New antitumor agent
DE102008002302A1 (en) 2007-06-13 2008-12-18 Basf Se Preparing etretinate, useful to treat severe psoriasis and ichthyosis vulgaris, comprises reacting acitretin with active reagent e.g. 1,1'-carbonyldiimidazole, followed by reacting with ethanol and/or alkali or alkaline earth ethanolate
WO2009086490A2 (en) * 2007-12-28 2009-07-09 Bridgestone Corporation Hydroxyaryl functionalized polymers

Also Published As

Publication number Publication date
NO143426C (en) 1981-02-25
AT340397B (en) 1977-12-12
GB1468401A (en) 1977-03-23
CH616135A5 (en) 1980-03-14
JPS5724333B2 (en) 1982-05-24
FR2223037A1 (en) 1974-10-25
ATA260174A (en) 1977-04-15
NL161429C (en) 1980-02-15
GB1468402A (en) 1977-03-23
DK155043B (en) 1989-01-30
ES424750A1 (en) 1976-06-01
LU88313I2 (en) 1994-09-09
CH616134A5 (en) 1980-03-14
NO741144L (en) 1974-10-01
CA1030975A (en) 1978-05-09
PL96105B1 (en) 1977-12-31
AR207004A1 (en) 1976-09-09
IL44368A (en) 1978-07-31
CH585166A5 (en) 1977-02-28
KE3047A (en) 1980-06-06
DD111368A5 (en) 1975-02-12
SE419752B (en) 1981-08-24
HU172655B (en) 1978-11-28
CH616136A5 (en) 1980-03-14
DE2414619C2 (en) 1983-06-01
NL161429B (en) 1979-09-17
IE39098L (en) 1974-09-30
SU613718A3 (en) 1978-06-30
LU69733A1 (en) 1976-02-04
DK155043C (en) 1989-07-03
ZA741580B (en) 1975-02-26
AU6656674A (en) 1975-09-18
NL930081I1 (en) 1993-09-16
PH13081A (en) 1979-11-23
YU88374A (en) 1983-01-21
JPS49126637A (en) 1974-12-04
BR7402525D0 (en) 1974-11-19
NL930081I2 (en) 1994-05-02
YU40253B (en) 1985-10-31
NL7404324A (en) 1974-10-02
MX152550A (en) 1985-08-23
DE2414619A1 (en) 1974-10-17
FI62280B (en) 1982-08-31
BE813002A (en) 1974-09-30
AU472475B2 (en) 1976-05-27
FI62280C (en) 1982-12-10
NO143426B (en) 1980-11-03
HK28780A (en) 1980-05-30
NO1994004I1 (en) 1994-07-07
FR2223037B1 (en) 1978-07-21
MY8100064A (en) 1981-12-31
SE7404312L (en) 1974-10-01
IL44368A0 (en) 1974-06-30
CU34050A (en) 1981-09-09

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