NO152968B - PROCEDURE FOR REGULATING THE PROGRAMMING MACHINERY IN A VESSEL WITH A STANDABLE PROPELLER - Google Patents
PROCEDURE FOR REGULATING THE PROGRAMMING MACHINERY IN A VESSEL WITH A STANDABLE PROPELLER Download PDFInfo
- Publication number
- NO152968B NO152968B NO830013A NO830013A NO152968B NO 152968 B NO152968 B NO 152968B NO 830013 A NO830013 A NO 830013A NO 830013 A NO830013 A NO 830013A NO 152968 B NO152968 B NO 152968B
- Authority
- NO
- Norway
- Prior art keywords
- dimethyl
- benzaldehyde
- residue
- iso
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 230000001105 regulatory effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims description 7
- UYHCMAZIKNVDSX-UHFFFAOYSA-N (benzylideneamino)thiourea Chemical class NC(=S)NN=CC1=CC=CC=C1 UYHCMAZIKNVDSX-UHFFFAOYSA-N 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000003935 benzaldehydes Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- -1 2,6-dimethyl-4-iso-propylbenzaldehyde thiosemicarbazone Chemical compound 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 125000003876 thiosemicarbazone group Chemical group 0.000 description 4
- AJQQOAYOYHVFEY-UHFFFAOYSA-N 2,6-dimethyl-4-propan-2-ylbenzaldehyde Chemical compound CC(C)C1=CC(C)=C(C=O)C(C)=C1 AJQQOAYOYHVFEY-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000000973 chemotherapeutic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- KNZSPKGFNVVCLS-UHFFFAOYSA-N 1,3,5-trimethylcyclohexa-2,4-diene-1-carbaldehyde Chemical compound CC1=CC(C)=CC(C)(C=O)C1 KNZSPKGFNVVCLS-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- CZLPCLANGIXFIE-UHFFFAOYSA-N 1-amino-3-prop-2-enylthiourea Chemical compound NNC(=S)NCC=C CZLPCLANGIXFIE-UHFFFAOYSA-N 0.000 description 1
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- FQUDPIIGGVBZEQ-UHFFFAOYSA-N acetone thiosemicarbazone Chemical compound CC(C)=NNC(N)=S FQUDPIIGGVBZEQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
- 239000012493 hydrazine sulfate Substances 0.000 description 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63H—MARINE PROPULSION OR STEERING
- B63H3/00—Propeller-blade pitch changing
- B63H3/10—Propeller-blade pitch changing characterised by having pitch control conjoint with propulsion plant control
Landscapes
- Engineering & Computer Science (AREA)
- Aviation & Aerospace Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- Ocean & Marine Engineering (AREA)
- Control Of Vehicle Engines Or Engines For Specific Uses (AREA)
- Beans For Foods Or Fodder (AREA)
- Toys (AREA)
- Liquid Developers In Electrophotography (AREA)
Description
Fremgangsmåte til fremstilling av kjemoterapeutisk virksomme benzaldehydtiosemikarbazoner. Process for the production of chemotherapeutically active benzaldehyde thiosemicarbazones.
Nærværende oppfinnelse vedrører en fremgangsmåte til fremstilling av terapeu-tisk virksomme benzaldehydtiosemikarbazoner med den generelle formel: The present invention relates to a method for the production of therapeutically active benzaldehyde thiosemicarbazones with the general formula:
hvor R,, R2 og R:i er like eller forskjellige lavere alkylrester, idet R,, R, og R., ikke samtidig er methyl i 2, 3 og 4-stilling, og Rj er hydrogen, en alkyl- eller alkenylrest, eller en cykloalkylrest eller en morfolingruppe. Fremgangsmåten ifølge oppfinnelsen er karakterisert ved at et med lavere alkylrester trisubstituert benzaldehyd om-settes med et alkalimetallrodanid, tiosemi-karbazid, aldehydtiosemikarbazon, som eventuelt kan være substituert med en alkyl- eller alkenylrest, eller cykloalkylrest eller morfolingruppe. where R1, R2 and R:i are the same or different lower alkyl residues, with R1, R1 and R1 not being methyl in the 2, 3 and 4-position at the same time, and Rj is hydrogen, an alkyl or alkenyl residue, or a cycloalkyl residue or a morpholine group. The process according to the invention is characterized in that a trisubstituted benzaldehyde with lower alkyl residues is reacted with an alkali metal rhodanide, thiosemicarbazide, aldehyde thiosemicarbazone, which may optionally be substituted with an alkyl or alkenyl residue, or cycloalkyl residue or morpholine group.
De ifølge oppfinnelsen fremstilte benzaldehydtiosemikarbazoner har kjemitera-peutisk effekt overfor virus. Forbindelsene ifølge oppfinnelsen har også aktivitet overfor et flertall seg imellom ikke beslek-tede viruser, samt også overfor bakterielle infeksjoner. Således har benzaldehydtio-semikarbazonene, hvor den aromatiske del er trisubstituert med samme eller forskjellige alkylrester, og hvor tiosemikarbazondelen eventuelt kan være substituert, fortrinnsvis med alkylrester, en høy kjemoterapeutisk aktivitet med lav toxisitet og gunstige reservasjonsforhold ved tilførsel i preparater bestemt for oral administrasjon. En særlig god aktivitet har alkyltrisubstitu-erte oxoaromatiske tiosemikarbazoner som er symmetrisk trialkylsubstituert, og hvor de to like alkylrester er bundet på begge sider av den avvikende tredje alkylsubsti-tuent som bør inneholde en forgrenet kjede. Substitusjonen i tiosemikarbazondelen øker fettoppløseligheten i sammenligning med tilsvarende forbindelser som er trisubstitu-erte i den aromatiske del. Som eksempel på forbindelser med spesielt gunstige biolog-iske egenskaper kan anføres 2,6-dimethyl-4-iso-propylbenzaldehydtiosemikarbazon og dets i tiosemikarbazondelen allyl-/isobutylsubstituerte derivat, samt 2,6-dimethyl-4-(sek./tert.)-butylbenzaldehydtiosemi-karbazon og dets i tiosemikarbazondelen allyl-/isobutylsubstituerte derivat. The benzaldehyde thiosemicarbazones produced according to the invention have a chemotherapeutic effect against viruses. The compounds according to the invention also have activity against a majority of unrelated viruses, as well as against bacterial infections. Thus, the benzaldehyde thio-semicarbazones, where the aromatic part is trisubstituted with the same or different alkyl residues, and where the thiosemicarbazone part may optionally be substituted, preferably with alkyl residues, have a high chemotherapeutic activity with low toxicity and favorable storage conditions when supplied in preparations intended for oral administration. Alkyl trisubstituted oxoaromatic thiosemicarbazones which are symmetrically trialkyl substituted, and where the two identical alkyl residues are bound on both sides by the deviating third alkyl substituent, which should contain a branched chain, have a particularly good activity. The substitution in the thiosemicarbazone part increases the fat solubility in comparison with corresponding compounds that are trisubstituted in the aromatic part. Examples of compounds with particularly favorable biological properties include 2,6-dimethyl-4-iso-propylbenzaldehyde thiosemicarbazone and its allyl-/isobutyl-substituted derivative in the thiosemicarbazone part, as well as 2,6-dimethyl-4-(sec./tert.) -butylbenzaldehyde thiosemi-carbazone and its in the thiosemicarbazone part allyl-/isobutyl-substituted derivative.
De følgende eksempler vil tjene til å belyse oppfinnelsen nærmere. The following examples will serve to illustrate the invention in more detail.
Eksempel 1 Example 1
En varm oppløsning av 3,6 g tiosemi-karbazid i 50 ml vann tilsettes 7 g 2,6-dimethyl-4-iso-propylbenzaldehyd i 70 ml ethanol og reaksjonsblandingen kokes under tilbakeløp i 2 timer. Dannede kry-staller skilles fra og omkrystalliseres fra eddiksyre, hvorved 2,6-dimethyl-4-isopro-pylbenzaldehydtiosemikarbazon oppnås. Smeltepunkt 216°C. A hot solution of 3.6 g of thiosemicarbazide in 50 ml of water is added to 7 g of 2,6-dimethyl-4-isopropylbenzaldehyde in 70 ml of ethanol and the reaction mixture is refluxed for 2 hours. Crystals formed are separated and recrystallized from acetic acid, whereby 2,6-dimethyl-4-isopropylbenzaldehyde thiosemicarbazone is obtained. Melting point 216°C.
Eksempel 2 Example 2
En blanding av 12 g hydrazinsulfat og 6,5 g kaliumkarbonat i 75 ml ethanol var-mes opp og tilsettes 9 g kaliumrodanid samt 12 g 2,6-dimethyl-4-sek.-butylbenzaldehyd. Reaksjonsblandingen kokes under tilbake-løp i 10 timer, fellingen skilles fra, vaskes med ethanol og slemmes opp i vann. Etter omkrystallisasjon fra eddiksyre oppnås 2,6-dimethyl-4-sek. -butylbenzaldehydtiosemi-karbazon. Smeltepunkt 200° C. A mixture of 12 g of hydrazine sulfate and 6.5 g of potassium carbonate in 75 ml of ethanol is heated and 9 g of potassium rhodanide and 12 g of 2,6-dimethyl-4-sec.-butylbenzaldehyde are added. The reaction mixture is refluxed for 10 hours, the precipitate is separated, washed with ethanol and slurried in water. After recrystallization from acetic acid, 2,6-dimethyl-4-sec is obtained. -butylbenzaldehyde thiosemi-carbazone. Melting point 200° C.
Eksempel 3 Example 3
I 150 ml varm 50 pst. eddiksyre opp-løses 15 g acetontiosemikarbazon og 26,5 g 2,6-dimethyl-4-tert. -butylbenzaldehyd i 40 ml vann tilsettes, hvoretter blandingen kokes under tilbakeløp i 1 time og avkjøles. Etter nøytralisasjon med konsentrert am-moniakk samles fellingen opp og omkrystalliseres fra dioxan-vann, hvorved 2,6-dimethyl-4-tert. -butylbenzaldehydtiosemi-karbazon oppnås. Smeltepunkt 240°C. 15 g of acetone thiosemicarbazone and 26.5 g of 2,6-dimethyl-4-tert are dissolved in 150 ml of warm 50% acetic acid. -butylbenzaldehyde in 40 ml of water is added, after which the mixture is boiled under reflux for 1 hour and cooled. After neutralization with concentrated ammonia, the precipitate is collected and recrystallized from dioxane-water, whereby 2,6-dimethyl-4-tert. -butylbenzaldehyde thiosemi-carbazone is obtained. Melting point 240°C.
Eksempel 4 Example 4
Til en blanding av 10 g 2,6-dimethyl-4-isopropyl-benzaldehyd i 70 ml ethanol og 2 ml eddiksyre tilsettes 8 g isobutyltiose-mikarbazid i 60 ml vann, og blandingen kokes under tilbakeløp i 1 time og kjøles av. Dannet krystallmasse skilles fra og omkrystalliseres fra sprit-vann, hvorved 2,6-dimethyl-4-iso-propylbenzaldehyd-iso-butyltiosemikarbazon isoleres. Smeltepunkt 117°C. To a mixture of 10 g of 2,6-dimethyl-4-isopropyl-benzaldehyde in 70 ml of ethanol and 2 ml of acetic acid, 8 g of isobutylthiose-micarbazide in 60 ml of water are added, and the mixture is boiled under reflux for 1 hour and cooled. The crystal mass formed is separated and recrystallized from alcohol-water, whereby 2,6-dimethyl-4-iso-propylbenzaldehyde-iso-butylthiosemicarbazone is isolated. Melting point 117°C.
Eksempel 5 Example 5
Til en blanding av 21 g 2,6-dimethyl-4-iso-propylbenzaldehyd i 200 ml ethanol og 6 ml eddiksyre tilsettes 15,6 g allyltiosemi-karbazid i 150 ml vann og reaksjonsblandingen kokes under tilbakeløp i 3 timer og avkjøles. De dannede krystallene omkrystalliseres fra iso-propanol, hvorved 2,6-dimethyl-4-iso-propyl-benzaldehyd-allyl-tiosemikarbazon oppnås. Smeltepunkt 115° C. To a mixture of 21 g of 2,6-dimethyl-4-isopropylbenzaldehyde in 200 ml of ethanol and 6 ml of acetic acid, 15.6 g of allylthiosemicarbazide in 150 ml of water are added and the reaction mixture is boiled under reflux for 3 hours and cooled. The formed crystals are recrystallized from iso-propanol, whereby 2,6-dimethyl-4-iso-propyl-benzaldehyde-allyl-thiosemicarbazone is obtained. Melting point 115° C.
Ifølge eksempel 1—5 fremstilles også følgende forbindelser: 1,3,5-tri-iso-propylbenzaldehydtiosemi-karbazon, smeltepunkt 139°C. 1,3,5-trimethylbenzaldehydtiosemikarba- zon, smeltepunkt 237°C. According to examples 1-5, the following compounds are also prepared: 1,3,5-tri-iso-propylbenzaldehyde thiosemi-carbazone, melting point 139°C. 1,3,5-trimethylbenzaldehyde thiosemicarba- zone, melting point 237°C.
2,6-dimethyl-4-iso-propylbenzaldehyd-oktadecyltiosemikarbazon, sm.p. 60°C. 2,6-dimethyl-4-iso-propylbenzaldehyde-octadecylthiosemicarbazone, m.p. 60°C.
2,6-dimethyl-4-iso-propylbenzaldehyd-heptadecyltiosemikarbazon, sm.p. 57°C. 2,6-dimethyl-4-iso-propylbenzaldehyde-heptadecylthiosemicarbazone, m.p. 57°C.
2,6-dimethyl-4-iso-propylbenzaldehyd-oleyltiosemikarbazon, olje 2,6-dimethyl-4-iso-propylbenzaldehyd-dodecyltiosemikarbazon, sm.p. 54°C. 2,6-dimethyl-4-iso-propylbenzaldehyd-undecyltiosemikarbazon, sm.p. 49°C. 2,6-dimethyl-4-iso-propylbenzaldehyde-oleylthiosemicarbazone, oil 2,6-dimethyl-4-iso-propylbenzaldehyde-dodecylthiosemicarbazone, m.p. 54°C. 2,6-dimethyl-4-iso-propylbenzaldehyde-undecylthiosemicarbazone, m.p. 49°C.
2,6-dimethyl-4-iso-propylbenzaldehyd-decyl-tiosemikarbazon, sm.p. 63°C. 2,6-dimethyl-4-iso-propylbenzaldehyde-decyl-thiosemicarbazone, m.p. 63°C.
2,6-dimethyl-4-iso-propylbenzaldehyd-l',3'-dimethylpentantiosemikarbazon, olje 2,6-dimethyl-4-iso-propylbenzaldehyde-1',3'-dimethylpentanthiosemicarbazone, oil
2,6-dimethyl-4-iso-propylbenzaldehyd-cyklohexyltiosemikarbazon, sm.p. 112°C. 2,6-dimethyl-4-iso-propylbenzaldehyde-cyclohexylthiosemicarbazone, m.p. 112°C.
2,6-dimethyl-4-iso-propylbenzaldehyd-morfolinotiosemikarbazon, sm.p. 174° C. 2,6-dimethyl-4-iso-propylbenzaldehyde-morpholinothiosemicarbazone, m.p. 174°C.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8102848A SE428792B (en) | 1981-05-07 | 1981-05-07 | PROCEDURE FOR REGULATING THE PROJECTING MACHINERY IN A VESSEL WITH ADJUSTABLE PROPELLER |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO830013L NO830013L (en) | 1983-01-04 |
| NO152968B true NO152968B (en) | 1985-09-16 |
| NO152968C NO152968C (en) | 1986-09-30 |
Family
ID=20343749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO83830013A NO152968C (en) | 1981-05-07 | 1983-01-04 | PROCEDURE FOR REGULATING THE PROGRAMMING MACHINERY IN A VESSEL WITH POSITIVE PROPELLER. |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0089960B1 (en) |
| DE (1) | DE3276696D1 (en) |
| DK (1) | DK157071C (en) |
| FI (1) | FI74246B (en) |
| NO (1) | NO152968C (en) |
| SE (1) | SE428792B (en) |
| WO (1) | WO1982003831A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3938567C1 (en) * | 1989-11-21 | 1991-04-11 | Urs Wollerau Ch Morgenthaler | |
| NO170722C (en) * | 1990-10-12 | 1992-11-25 | Oddvard Johnsen | PROCEDURE AND DEVICE FOR THE OPTION OF OPTIMAL USE OF A VESSEL'S PROGRAMMING MACHINERY |
| DE4441604C2 (en) * | 1994-11-23 | 1997-09-04 | Stn Atlas Elektronik Gmbh | Ship propulsion system with two coaxial, counter-rotating propellers |
| CA2921006C (en) * | 2015-02-27 | 2017-07-18 | Honda Motor Co., Ltd. | Control apparatus for outboard motor |
| SG11201708109SA (en) * | 2015-04-20 | 2017-10-30 | Lean Marine Sweden Ab | Method for controlling the fuel comsumption of a ship |
| DE102015014857A1 (en) * | 2015-11-17 | 2017-05-18 | Man Diesel & Turbo Se | A method of operating a marine propulsion system and marine propulsion system |
| DK179755B1 (en) * | 2017-11-02 | 2019-05-08 | Frugal Technologies Aps | Procedure for progress control using a progress control system and its use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3069548A (en) * | 1958-12-17 | 1962-12-18 | Machlett Lab Inc | Protective circuits for electron tubes |
| US3110348A (en) * | 1959-12-04 | 1963-11-12 | Escher Wyss Ag | Control device for adjusting a variablepitch marine propeller |
| SE215146C1 (en) * | 1963-12-11 | 1967-09-05 | ||
| DE1531750A1 (en) * | 1967-10-05 | 1970-02-12 | Inst Schiffbau Rostock | Arrangement for optimizing the operation of ships driven by controllable pitch propellers |
| DE1531730A1 (en) * | 1967-11-25 | 1970-02-05 | Arthur Kuppert | Wind turbine sailor |
| JPS5756639A (en) * | 1980-09-19 | 1982-04-05 | Nippon Kokan Kk <Nkk> | Constant speed control for ship |
-
1981
- 1981-05-07 SE SE8102848A patent/SE428792B/en unknown
-
1982
- 1982-05-05 DE DE8282901550T patent/DE3276696D1/en not_active Expired
- 1982-05-05 WO PCT/SE1982/000150 patent/WO1982003831A1/en active IP Right Grant
- 1982-05-05 EP EP82901550A patent/EP0089960B1/en not_active Expired
-
1983
- 1983-01-04 NO NO83830013A patent/NO152968C/en unknown
- 1983-01-07 DK DK005483A patent/DK157071C/en not_active IP Right Cessation
- 1983-06-01 FI FI831965A patent/FI74246B/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FI831965L (en) | 1983-06-01 |
| DK5483A (en) | 1983-01-07 |
| DK157071B (en) | 1989-11-06 |
| FI831965A0 (en) | 1983-06-01 |
| EP0089960A1 (en) | 1983-10-05 |
| DE3276696D1 (en) | 1987-08-13 |
| DK5483D0 (en) | 1983-01-07 |
| NO152968C (en) | 1986-09-30 |
| DK157071C (en) | 1990-04-16 |
| WO1982003831A1 (en) | 1982-11-11 |
| SE8102848L (en) | 1982-11-08 |
| NO830013L (en) | 1983-01-04 |
| SE428792B (en) | 1983-07-25 |
| EP0089960B1 (en) | 1987-07-08 |
| FI74246B (en) | 1987-09-30 |
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