NO146198B - Mellomprodukt for fremstilling av 5-fluor-2-methyl-1-(p-methylsulfinylbenzyliden)-ind-2-en-3-yl-eddiksyre - Google Patents
Mellomprodukt for fremstilling av 5-fluor-2-methyl-1-(p-methylsulfinylbenzyliden)-ind-2-en-3-yl-eddiksyre Download PDFInfo
- Publication number
- NO146198B NO146198B NO791267A NO791267A NO146198B NO 146198 B NO146198 B NO 146198B NO 791267 A NO791267 A NO 791267A NO 791267 A NO791267 A NO 791267A NO 146198 B NO146198 B NO 146198B
- Authority
- NO
- Norway
- Prior art keywords
- fluoro
- acetic acid
- methyl
- ind
- methylsulphinylbenzylide
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 8
- -1 5-fluoro-2-methyl-indan-l-ol -3-yl-acetic acid Chemical group 0.000 claims description 6
- MLKXDPUZXIRXEP-UHFFFAOYSA-N 2-[6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]-1-indenyl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2C1=CC1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000012448 Lithium borohydride Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
-
- 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
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Foreliggende oppfinnelse angår et mellomprodukt, 5-fluor-2-methyl-indan-l-ol-3-yl-eddiksyre for anvendelse ved en ny og forbedret fremgangsmåte ved fremstilling av 5-fluor-2-methyl-l-(p-methylsulfinylbenzyliden)-ind-2-en-3-yl-eddiksyre som er en kjent forbindelse med antiinflammatorisk aktivitet beskrevet i US patent 3 654 349.
Anvendelsen av foreliggende mellomprodukt er beskrevet
i norsk patent 141 050.
Foreliggende mellomprodukt kan fremstilles ved å redusere 5-fluor-2-methyl-indanon-3-eddiksyren (kjent fra US patent 3 692 825) enten ved kjemiske eller katalytiske midler til 5-fluor-2-methyl-indan-l-ol-3-yl-eddiksyre. Passende reagenser innbefatter alkalimetallborhydrider, aluminiumisopropoxyd og hydrogen under anvendelse av en passende hydrogeneringskatalysator, som findelt nikkel, platina eller palladium. Den kjemiske reaksjon utføres i et passende inert oppløsningsmiddel som vann, alkohol eller blandinger derav, avhengig av naturen av reduksjonsmidlet. Det foretrukne reduksjonsmiddel er natriumborhydrid i vann som er gjort alkalisk. Reduksjonsmidlet er tilstede i en konsentrasjon på fra 0,25 til 3 mol pr. mol indanon, fortrinnsvis fra 1,2 til 2,0 mol. Eksempler på passende oppløsningsmidler er alkalisk vann, methanol, ethanol og særlig isopropanol. Reaksjonen kan utføres ved en temperatur fra 0° til 85°C, fortrinnsvis mellom 40°C og 82°C. Reaksjonshastigheten er avhengig av temperaturen ved hvilken den utføres. Reaksjonstiden er ikke kritisk, og i alminnelighet utføres reaksjonen inntil den er i det vesentlige fullstendig. Trykket er ikke kritisk for den kjemiske reduksjon. I alminnelighet utføres reaksjonen under atmosfæretrykk i et åpent system.
Reduksjonen av 5-fluor-2-methyl-indanon-3-eddiksyre kan også utføres ved katalytisk hydrogenering. Reaksjonen ut-føres under anvendelse av en <p>assende hydrogeneringskatalysator som findelt nikkel, iridium, rhenium, ruthenium, rhodium, platina eller palladium eller et redusert metalloxyd derav, og hydrogen under et trykk fra atmosfæretrykk til 200 atmosfærer, fortrinnsvis atmosfæretrykk til 10 atmosfærer i et lukket system. Katalysatorkonsentrasjonen er fra 0,1 til 10 vekt% av indanonet, fortrinnsvis fra 1 til 5%. Reaksjonen kan utføres med et oppløsningsmiddel. Passende oppløsnings-midler innbefatter mettede hydrocarboner, alkoholer, estere og alkalisk vann og blandinger derav, som hexån, methanol, ethanol, ethylacetat og alkalisk vann. Katalysatoren kan være enten anbrakt på en bærer som trekull eller det findelte metallpulver eller reduserte metalloxyd derav. Reaksjonshastigheten er avhengig av temperaturen ved hvilken den ut-føres. Reaksjonstiden er ikke kritisk, og i alminnelighet ut-føres reaksjonen inntil den er i det'vesentlige fullstendig. Foreliggende mellomprodukt isoleres vanligvis ikke fra oppløs-ningsmiddelblandingen, men omsettes som den er i det neste reaksjonstrinn, beskrevet i norsk patent 141 050.
Eksempel 1
5- f1uor- 2- methy1- i ndan- 1- o1- 3- y1- eddiksyre ( V)
En oppløsning av 390 mg (1,8 mmol) 5-fluor-2-methyl-indanon-3-eddiksyre i 6 ml isopropanol gjøres alkalisk ved til-setning av 2,5M natriumhydroxyd (til pH 9 til 10). Til denne oppløsning tilsettes 100 mg (2,6 mmol) natriumborhydrid. Oppløsningen omrøres ved værelsetemperatur i 80 minutter og ved 60°C i 45 minutter. Oppløsningen helles i 2M saltsyre og ekstraheres med methylendiklorid. Det organiske skikt tørres, og inndampes, hvorved man får 5-fluor-2-methyl-indan-l-ol-3-yl-eddiksyre.
På tilsvarende måte fåes, når en ekvivalent mengde lithiumborhydrid eller kaliumborhydrid anvendes istedenfor natriumborhydrid i ovenstående eksempel, tilsvarende resultater.
Eksempel 2
5- fluor- 2- methyl- indan- l- ol- 3- yl- eddiksyre
Til en oppløsning av 390 mg (1,8 mmol) 5-fluor-2-methyl-indanon-3-eddiksyre i 6 ml isopropanol tilsettes 250 mg platinaoxyd. Hydrogeneringen utføres på et Paar-apparat ved værelsetemperatur og 2,8 kg/cm 2 inntil reaksjonen er fullstendig (30 minutter). Oppløsningen filtreres, tørres og inndampes-, hvorved man får 5-fluor-2-methyl-indan-l-ol-3-yl-eddiksyre.
På lignende måte fåes, når en ekvivalent mengde nikkel eller palladium anvendes istedenfor platinaoxyd i ovenstående eksempel, tilsvarende resultater.
Claims (1)
- Mellomprodukt for fremstilling av 5-fluor-2-methyl-1-(p-methylsulfinylbenzyliden)-ind-2-en-3-yl-eddiksyre, karakterisert ved at det er 5-fluor-2-methyl-indan-l-ol-3-yl-eddiksyre med formelen:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/511,349 US3998875A (en) | 1974-10-02 | 1974-10-02 | Process of preparing 5-fluoro-2-methyl-1-(paramethylsulfinylbenzylidene)-indenyl-3-acetic acid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO791267L NO791267L (no) | 1976-04-05 |
| NO146198B true NO146198B (no) | 1982-05-10 |
| NO146198C NO146198C (no) | 1982-08-18 |
Family
ID=24034513
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753179A NO141050C (no) | 1974-10-02 | 1975-09-18 | Fremgangsmaate ved fremstilling av 5-fluor-2-methyl-1-(p-methylsulfinylbenzyliden)-ind-2-en-3-yl-eddiksyre |
| NO791267A NO146198C (no) | 1974-10-02 | 1979-04-17 | Mellomprodukt for fremstilling av 5-fluor-2-methyl-1-(p-methylsulfinylbenzyliden)-ind-2-en-3-yl-eddiksyre |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753179A NO141050C (no) | 1974-10-02 | 1975-09-18 | Fremgangsmaate ved fremstilling av 5-fluor-2-methyl-1-(p-methylsulfinylbenzyliden)-ind-2-en-3-yl-eddiksyre |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US3998875A (no) |
| JP (1) | JPS51105049A (no) |
| AT (1) | AT344154B (no) |
| BE (1) | BE834080A (no) |
| CH (1) | CH615158A5 (no) |
| CS (2) | CS183850B2 (no) |
| DD (1) | DD125639A5 (no) |
| DE (1) | DE2543870A1 (no) |
| DK (1) | DK416975A (no) |
| ES (1) | ES441404A1 (no) |
| FI (1) | FI61690C (no) |
| FR (1) | FR2286817A1 (no) |
| GB (1) | GB1483980A (no) |
| HU (1) | HU171805B (no) |
| LU (1) | LU73496A1 (no) |
| NL (1) | NL7510944A (no) |
| NO (2) | NO141050C (no) |
| PL (2) | PL103093B1 (no) |
| SE (1) | SE7510329L (no) |
| SU (3) | SU860695A1 (no) |
| YU (2) | YU239875A (no) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4368127A (en) * | 1979-07-02 | 1983-01-11 | Akzona Incorporated | Fabric softening compounds and method |
| DE3266350D1 (en) * | 1981-06-11 | 1985-10-24 | Sumitomo Chemical Co | Tetrahydronaphthalene derivatives and their production |
| IT1190371B (it) * | 1985-06-19 | 1988-02-16 | Zambon Spa | Processo per la preparazione dell'acido cis-5-fluoro-2-metil-1-(4-metiltiobenziliden)-indenil-3-acetico |
| US5965619A (en) * | 1996-06-13 | 1999-10-12 | Cell Pathways Inc. | Method for treating patients having precancerous lesions with substituted indene derivatives |
| US6121321A (en) * | 1996-06-13 | 2000-09-19 | Cell Pathways, Inc. | Substituted methoxy benzylidene indenyl acetic and propionic acids for treating patients with precancerous lesions |
| US6063818A (en) * | 1996-06-13 | 2000-05-16 | Cell Pathways Inc. | Substituted benzylidene indenyl formamides, acetamides and propionamides |
| US5998477A (en) * | 1996-06-13 | 1999-12-07 | Cell Pathways Inc. | Substituted methoxy benzylidene indenyl-acetic and propionic acids for treating patients with precancerous lesions |
| AU3515397A (en) * | 1996-07-01 | 1998-01-21 | Procter & Gamble Company, The | Dehydrated potato flakes |
| US5948779A (en) * | 1997-12-12 | 1999-09-07 | Cell Pathways, Inc. | Substituted condensation products of n-benzyl-3-indenyl acetamides with heterocyclic aldehydes |
| US6028116A (en) * | 1998-04-03 | 2000-02-22 | Cell Pathways, Inc. | Substituted condensation products of 1H-indenyl-hydroxyalkanes with aldehydes for neoplasia |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532752A (en) * | 1965-12-30 | 1970-10-06 | Merck & Co Inc | 1-alkylidene-3-indenyl aliphatic amines |
| US3547923A (en) * | 1968-03-25 | 1970-12-15 | Bristol Myers Co | Piperazyl ethyl 7h-benzocycloheptenes |
| US3692825A (en) * | 1970-05-01 | 1972-09-19 | Merck & Co Inc | Indanyl acetic acids |
| US3766259A (en) * | 1970-05-01 | 1973-10-16 | Merck & Co Inc | Preparation of 1-aryl-3-indenyl acetic acids |
| US3654349A (en) * | 1970-05-01 | 1972-04-04 | Merck & Co Inc | Substituted indenyl acetic acids |
| US3725548A (en) * | 1970-05-01 | 1973-04-03 | Merck & Co Inc | Substituted indenyl acetic acids in the treatment of pain, fever or inflammation |
| US3870753A (en) * | 1973-12-20 | 1975-03-11 | Merck & Co Inc | Process for preparing indenyl acetic acids |
-
1974
- 1974-10-02 US US05/511,349 patent/US3998875A/en not_active Expired - Lifetime
-
1975
- 1975-09-15 FI FI752573A patent/FI61690C/fi not_active IP Right Cessation
- 1975-09-16 SE SE7510329A patent/SE7510329L/xx unknown
- 1975-09-17 DK DK416975A patent/DK416975A/da unknown
- 1975-09-17 NL NL7510944A patent/NL7510944A/xx not_active Application Discontinuation
- 1975-09-18 NO NO753179A patent/NO141050C/no unknown
- 1975-09-23 FR FR7529068A patent/FR2286817A1/fr active Granted
- 1975-09-24 YU YU02398/75A patent/YU239875A/xx unknown
- 1975-09-24 SU SU752175253A patent/SU860695A1/ru active
- 1975-09-25 AT AT734575A patent/AT344154B/de not_active IP Right Cessation
- 1975-09-26 PL PL1975183608A patent/PL103093B1/pl unknown
- 1975-09-26 PL PL1975207885A patent/PL103733B1/pl unknown
- 1975-09-30 DD DD188629A patent/DD125639A5/xx unknown
- 1975-09-30 CH CH1268975A patent/CH615158A5/de not_active IP Right Cessation
- 1975-09-30 ES ES441404A patent/ES441404A1/es not_active Expired
- 1975-10-01 CS CS7700000967A patent/CS183850B2/cs unknown
- 1975-10-01 GB GB40159/75A patent/GB1483980A/en not_active Expired
- 1975-10-01 BE BE160596A patent/BE834080A/xx unknown
- 1975-10-01 LU LU73496A patent/LU73496A1/xx unknown
- 1975-10-01 HU HU75ME00001904A patent/HU171805B/hu unknown
- 1975-10-01 DE DE19752543870 patent/DE2543870A1/de not_active Withdrawn
- 1975-10-01 CS CS7500006632A patent/CS183821B2/cs unknown
- 1975-10-02 JP JP50118311A patent/JPS51105049A/ja active Pending
-
1976
- 1976-09-22 US US05/725,593 patent/US4123457A/en not_active Expired - Lifetime
-
1979
- 1979-04-17 NO NO791267A patent/NO146198C/no unknown
- 1979-10-25 SU SU792832510A patent/SU957760A3/ru active
-
1980
- 1980-07-30 SU SU802953010A patent/SU995705A3/ru active
-
1981
- 1981-06-04 YU YU01414/81A patent/YU141481A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK416975A (da) | 1976-04-03 |
| LU73496A1 (no) | 1976-08-19 |
| DE2543870A1 (de) | 1976-04-22 |
| ATA734575A (de) | 1977-11-15 |
| GB1483980A (en) | 1977-08-24 |
| NO753179L (no) | 1976-04-05 |
| YU239875A (en) | 1982-06-30 |
| SU860695A1 (ru) | 1981-08-30 |
| FI752573A (no) | 1976-04-03 |
| US4123457A (en) | 1978-10-31 |
| AT344154B (de) | 1978-07-10 |
| JPS51105049A (en) | 1976-09-17 |
| NO146198C (no) | 1982-08-18 |
| PL103093B1 (pl) | 1979-05-31 |
| FI61690B (fi) | 1982-05-31 |
| SE7510329L (sv) | 1976-04-05 |
| US3998875A (en) | 1976-12-21 |
| DD125639A5 (no) | 1977-05-04 |
| SU995705A3 (ru) | 1983-02-07 |
| CS183821B2 (en) | 1978-07-31 |
| CH615158A5 (no) | 1980-01-15 |
| NO141050B (no) | 1979-09-24 |
| ES441404A1 (es) | 1977-03-01 |
| SU957760A3 (ru) | 1982-09-07 |
| FI61690C (fi) | 1982-09-10 |
| PL103733B1 (pl) | 1979-07-31 |
| CS183850B2 (en) | 1978-07-31 |
| FR2286817B1 (no) | 1979-01-05 |
| BE834080A (fr) | 1976-04-01 |
| NL7510944A (nl) | 1976-04-06 |
| YU141481A (en) | 1982-02-28 |
| FR2286817A1 (fr) | 1976-04-30 |
| NO791267L (no) | 1976-04-05 |
| HU171805B (hu) | 1978-03-28 |
| NO141050C (no) | 1980-01-02 |
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