ES453304A1 - Amino acid derivatives - Google Patents

Amino acid derivatives

Info

Publication number
ES453304A1
ES453304A1 ES453304A ES453304A ES453304A1 ES 453304 A1 ES453304 A1 ES 453304A1 ES 453304 A ES453304 A ES 453304A ES 453304 A ES453304 A ES 453304A ES 453304 A1 ES453304 A1 ES 453304A1
Authority
ES
Spain
Prior art keywords
group
compounds
general formula
formula
see formula
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
ES453304A
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 HU74FE00000928A external-priority patent/HU171576B/en
Priority claimed from HU74CI1558A external-priority patent/HU174114B/en
Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of ES453304A1 publication Critical patent/ES453304A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
    • A61K35/55—Glands not provided for in groups A61K35/22 - A61K35/545, e.g. thyroids, parathyroids or pineal glands
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A61K8/981—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of mammals or bird
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • 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
    • 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
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
    • A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Birds (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biophysics (AREA)
  • Developmental Biology & Embryology (AREA)
  • Virology (AREA)
  • Biotechnology (AREA)
  • Nutrition Science (AREA)
  • Biomedical Technology (AREA)
  • Cell Biology (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

A procedure for the preparation of new amino acid derivatives of the general formula (I) ** (See formula) ** where R is a hydrogen atom or an alcohol group with 1 to 4 carbon atoms, n is an integer from 1 to 3, and m is 2 or 3, as well as the optically active salts and isomers of these compounds, characterized in that compounds of the general formula (II) are reacted ** (See formula) ** wherein R7 signifies an aralkoxy, formyl, trifluoroacetyl or p-toluenesulfonyl group, a benzyloxycarbonyl group, a -CO- group or a group of the formula (see formula) (in which R15 means an alcohol group with 1 to 4 carbon atoms, a cycloalcohyl group, an optionally substituted aralcohyl group or an optionally substituted aryl group), R8 means a hydrogen atom or a -CO- group, provided that in case R7 = R8 = -CO- group, R7 and R8 are closed on an orthophenylene group to form the ring, A4 means an aralkoxy group, preferably a benzyloxy group, a substituted aralkoxy group, preferably a p-methoxybenzyl xi group, or a p-nitrobenzyloxy group, and A7 means a hydroxyl, azide, succinimidoxy, p-nitrophenyloxy or pentachlorophenyloxy group or an alkoxycarbonyloxy group with 2 to 4 carbon atoms, with compounds of the general formula (III) ** (See formula) ** the compounds obtained from the general formula are oxidized ** (See formula) ** and is separated from the compounds obtained from the general formula (V) ** (See formula) ** the protecting group of the α-carboxyl group and are cleaved from the compounds obtained of the general formula (VI) ** (See formula) ** the protecting groups of the nitrogen atom by acidolysis, hydrogenolysis or with a dilute solution of ammonium hydroxide, sodium, sodium amide or hydrazine or by means of enzymatic hydrolysis, preferably with leucine aminopeptidase, and the obtained compounds are converted into their salts or liberated of their salts and/or the compounds are prepared in the form of their optically active isomers by using optically active reagents in any reaction step or by subjecting the compounds to racemate separation. (Machine-translation by Google Translate, not legally binding)
ES453304A 1974-04-29 1976-11-13 Amino acid derivatives Expired ES453304A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU74FE00000928A HU171576B (en) 1974-04-29 1974-04-29 Process for the isolation of gamma-l-glutamyl-taurine
HU74CI1558A HU174114B (en) 1975-03-26 1975-03-26 Process for producing new aminoacid derivatives

Publications (1)

Publication Number Publication Date
ES453304A1 true ES453304A1 (en) 1977-11-16

Family

ID=26318406

Family Applications (4)

Application Number Title Priority Date Filing Date
ES436986A Expired ES436986A1 (en) 1974-04-29 1975-04-25 Amino acid derivatives
ES453305A Expired ES453305A1 (en) 1974-04-29 1976-11-13 Amino acid derivatives
ES453304A Expired ES453304A1 (en) 1974-04-29 1976-11-13 Amino acid derivatives
ES453306A Expired ES453306A1 (en) 1974-04-29 1976-11-13 Amino acid derivatives

Family Applications Before (2)

Application Number Title Priority Date Filing Date
ES436986A Expired ES436986A1 (en) 1974-04-29 1975-04-25 Amino acid derivatives
ES453305A Expired ES453305A1 (en) 1974-04-29 1976-11-13 Amino acid derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES453306A Expired ES453306A1 (en) 1974-04-29 1976-11-13 Amino acid derivatives

Country Status (23)

Country Link
JP (1) JPS6012347B2 (en)
AR (3) AR218221A1 (en)
AT (6) AT361902B (en)
AU (1) AU499173B2 (en)
BE (1) BE828546A (en)
BG (4) BG26517A4 (en)
CA (1) CA1051802A (en)
CH (4) CH617183A5 (en)
CS (4) CS209855B2 (en)
DD (2) DD122377A5 (en)
DE (2) DE2518160A1 (en)
DK (10) DK155433C (en)
EG (1) EG11847A (en)
ES (4) ES436986A1 (en)
FI (1) FI65990C (en)
FR (1) FR2279388A1 (en)
GB (1) GB1504541A (en)
IL (1) IL47149A (en)
NL (1) NL183186C (en)
NO (2) NO146430C (en)
PL (2) PL111745B1 (en)
SE (2) SE430164B (en)
SU (1) SU747419A3 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU178199B (en) * 1976-05-06 1982-03-28 Chinoin Gyogyszer Es Vegyeszet New process for producing amides of omega-amino-carboxylic acids
HU180443B (en) * 1979-04-02 1983-03-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing a pharmaceutical preparation with synergetic action against radiation
HU185632B (en) * 1981-03-27 1985-03-28 Chinoin Gyogyszer Es Vegyeszet New process for preparing gamma-glutamyl-taurine
CH665645A5 (en) * 1981-07-09 1988-05-31 Michel Flork DIPEPTIDE DERIVATIVES AND THEIR PREPARATION PROCESS.
HU208072B (en) * 1990-02-28 1993-08-30 Chinoin Gyogyszer Es Vegyeszet Process for producing pharmaceutical composition suitable for preventing and curing autoimmune diseases and skin affections caused by heat and light radiacion
JPH0680964A (en) * 1991-12-27 1994-03-22 Sogo Yatsukou Kk Active-oxygen scavenger
JPH11180846A (en) * 1997-12-15 1999-07-06 Sogo Pharmaceut Co Ltd Cosmetic
DE10133197A1 (en) * 2001-07-07 2003-01-23 Beiersdorf Ag Use of topical compositions containing beta-amino acids, guanidinoethanesulfonate, homotaurine and their precursors and derivatives e.g. to improve skin condition and to treat or prevent skin disorders
DK2089417T3 (en) 2006-10-12 2015-03-23 Bhi Ltd Partnership Methods, Compounds, Compositions and Vehicles for Delivery of 3-Amion-1-Propanesulfonic Acid
US9662304B1 (en) * 2013-06-13 2017-05-30 Thermolife International, Llc Substituted glutaurine compounds and substituted glutaurine derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU169462B (en) * 1971-08-04 1976-11-28

Also Published As

Publication number Publication date
NO146430C (en) 1982-09-29
NO149036B (en) 1983-10-24
BG26370A4 (en) 1979-03-15
DK442777A (en) 1977-10-06
DK182875A (en) 1975-10-30
DK155732B (en) 1989-05-08
JPS514121A (en) 1976-01-14
SE441356B (en) 1985-09-30
CA1051802A (en) 1979-04-03
SE7812884L (en) 1978-12-14
JPS6012347B2 (en) 1985-04-01
DK158676C (en) 1991-01-14
DE2559989B1 (en) 1981-02-05
DE2559989C3 (en) 1981-11-19
BG26368A3 (en) 1979-03-15
CS209857B2 (en) 1981-12-31
AR218222A1 (en) 1980-05-30
ATA624777A (en) 1980-03-15
DK245783A (en) 1983-05-31
AR218221A1 (en) 1980-05-30
DE2518160C2 (en) 1993-05-06
ATA624977A (en) 1978-12-15
FI751256A (en) 1975-10-30
NO810816L (en) 1975-10-30
DE2518160A1 (en) 1975-11-20
CS209855B2 (en) 1981-12-31
DK159267B (en) 1990-09-24
DK442577A (en) 1977-10-06
ATA314075A (en) 1980-09-15
DK443077A (en) 1977-10-06
CH624098A5 (en) 1981-07-15
DK159654B (en) 1990-11-12
FI65990B (en) 1984-04-30
DD122377A5 (en) 1976-10-05
FR2279388B1 (en) 1978-07-28
AT374484B (en) 1984-04-25
DK442677A (en) 1977-10-06
DK245783D0 (en) 1983-05-31
DK155433C (en) 1989-10-16
AT351007B (en) 1979-07-10
DK442877A (en) 1977-10-06
AT361902B (en) 1981-04-10
ATA323079A (en) 1983-09-15
BE828546A (en) 1975-08-18
DK158676B (en) 1990-07-02
EG11847A (en) 1979-06-30
ATA624877A (en) 1980-03-15
DK155433B (en) 1989-04-10
AT359084B (en) 1980-10-27
DK442477A (en) 1977-10-06
DK155520B (en) 1989-04-17
GB1504541A (en) 1978-03-22
AT359085B (en) 1980-10-27
CH621334A5 (en) 1981-01-30
NL183186C (en) 1988-08-16
AU499173B2 (en) 1979-04-05
DK155672C (en) 1989-10-09
CH617183A5 (en) 1980-05-14
DK442377A (en) 1977-10-06
NL7505075A (en) 1975-10-31
SE430164B (en) 1983-10-24
IL47149A (en) 1979-05-31
CS209856B2 (en) 1981-12-31
SE7504828L (en) 1975-10-30
AT370724B (en) 1983-04-25
NO751504L (en) 1975-10-30
ES436986A1 (en) 1977-06-16
DK155732C (en) 1989-10-02
DK159267C (en) 1991-02-18
NO149036C (en) 1984-02-01
BG26369A4 (en) 1979-03-15
BG26517A4 (en) 1979-04-12
FR2279388A1 (en) 1976-02-20
IL47149A0 (en) 1975-06-25
DK159654C (en) 1991-04-08
CH621333A5 (en) 1981-01-30
CS209858B2 (en) 1981-12-31
FI65990C (en) 1984-08-10
ES453306A1 (en) 1977-11-16
AU8056475A (en) 1976-11-04
ATA323179A (en) 1982-09-15
NO146430B (en) 1982-06-21
ES453305A1 (en) 1977-11-16
DK442977A (en) 1977-10-06
PL111745B1 (en) 1980-09-30
AR217236A1 (en) 1980-03-14
SU747419A3 (en) 1980-07-23
DK155520C (en) 1989-10-16
PL111746B1 (en) 1980-09-30
DK155672B (en) 1989-05-01
DD125070A5 (en) 1977-03-30

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