NO156328B - Konstruksjon med keramisk overflatebelegg samt fremgangsmaate til fremstilling av samme. - Google Patents
Konstruksjon med keramisk overflatebelegg samt fremgangsmaate til fremstilling av samme. Download PDFInfo
- Publication number
- NO156328B NO156328B NO801084A NO801084A NO156328B NO 156328 B NO156328 B NO 156328B NO 801084 A NO801084 A NO 801084A NO 801084 A NO801084 A NO 801084A NO 156328 B NO156328 B NO 156328B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- benzodiazepine
- methyl
- hydrazine hydrate
- chloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000919 ceramic Substances 0.000 title 1
- 239000011248 coating agent Substances 0.000 title 1
- 238000000576 coating method Methods 0.000 title 1
- 238000010276 construction Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 18
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000010992 reflux Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- DHZYXWMZLAKTQV-UHFFFAOYSA-N diazepin-3-one Chemical class O=C1C=CC=CN=N1 DHZYXWMZLAKTQV-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- -1 cyclic ketimine Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- VEJJCRAVOYFKAU-UHFFFAOYSA-N n-(2-benzoylphenyl)-2-(1,3-dioxoisoindol-2-yl)acetamide Chemical class O=C1C2=CC=CC=C2C(=O)N1CC(=O)NC1=CC=CC=C1C(=O)C1=CC=CC=C1 VEJJCRAVOYFKAU-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IKWQWOFXRCUIFT-UHFFFAOYSA-N benzene-1,2-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C(=O)NN IKWQWOFXRCUIFT-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RHZBRCQIKQUQHQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetyl chloride Chemical compound C1=CC=C2C(=O)N(CC(=O)Cl)C(=O)C2=C1 RHZBRCQIKQUQHQ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- SZZBOLKXOKEKAN-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-2-(1,3-dioxoisoindol-2-yl)acetamide Chemical compound C=1C(Cl)=CC=C(NC(=O)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 SZZBOLKXOKEKAN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- ABEVIHIQUUXDMS-UHFFFAOYSA-N (2-bromophenyl)-phenylmethanone Chemical compound BrC1=CC=CC=C1C(=O)C1=CC=CC=C1 ABEVIHIQUUXDMS-UHFFFAOYSA-N 0.000 description 1
- KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 description 1
- IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 229960001269 glycine hydrochloride Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SSODIFRMVIJEQE-UHFFFAOYSA-N n-(2-benzoyl-4-bromophenyl)-2-(1,3-dioxoisoindol-2-yl)acetamide Chemical compound C=1C(Br)=CC=C(NC(=O)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 SSODIFRMVIJEQE-UHFFFAOYSA-N 0.000 description 1
- WGHYEZDVCKTDJE-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-2-(1,3-dioxoisoindol-2-yl)-n-methylacetamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC(=O)N(C)C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WGHYEZDVCKTDJE-UHFFFAOYSA-N 0.000 description 1
- OTLLGSKNXHICKC-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-2-(1,3-dioxoisoindol-2-yl)propanamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C)C(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OTLLGSKNXHICKC-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
- F01D—NON-POSITIVE DISPLACEMENT MACHINES OR ENGINES, e.g. STEAM TURBINES
- F01D25/00—Component parts, details, or accessories, not provided for in, or of interest apart from, other groups
- F01D25/08—Cooling; Heating; Heat-insulation
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B37/00—Joining burned ceramic articles with other burned ceramic articles or other articles by heating
- C04B37/02—Joining burned ceramic articles with other burned ceramic articles or other articles by heating with metallic articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/18—Layered products comprising a layer of metal comprising iron or steel
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C4/00—Coating by spraying the coating material in the molten state, e.g. by flame, plasma or electric discharge
- C23C4/02—Pretreatment of the material to be coated, e.g. for coating on selected surface areas
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C4/00—Coating by spraying the coating material in the molten state, e.g. by flame, plasma or electric discharge
- C23C4/04—Coating by spraying the coating material in the molten state, e.g. by flame, plasma or electric discharge characterised by the coating material
- C23C4/10—Oxides, borides, carbides, nitrides or silicides; Mixtures thereof
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C4/00—Coating by spraying the coating material in the molten state, e.g. by flame, plasma or electric discharge
- C23C4/04—Coating by spraying the coating material in the molten state, e.g. by flame, plasma or electric discharge characterised by the coating material
- C23C4/10—Oxides, borides, carbides, nitrides or silicides; Mixtures thereof
- C23C4/11—Oxides
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
- F01D—NON-POSITIVE DISPLACEMENT MACHINES OR ENGINES, e.g. STEAM TURBINES
- F01D5/00—Blades; Blade-carrying members; Heating, heat-insulating, cooling or antivibration means on the blades or the members
- F01D5/12—Blades
- F01D5/28—Selecting particular materials; Particular measures relating thereto; Measures against erosion or corrosion
- F01D5/284—Selection of ceramic materials
-
- 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
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T50/00—Aeronautics or air transport
- Y02T50/60—Efficient propulsion technologies, e.g. for aircraft
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S277/00—Seal for a joint or juncture
- Y10S277/935—Seal made of a particular material
- Y10S277/939—Containing metal
- Y10S277/941—Aluminum or copper
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S277/00—Seal for a joint or juncture
- Y10S277/935—Seal made of a particular material
- Y10S277/943—Ceramic or glass
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/922—Static electricity metal bleed-off metallic stock
- Y10S428/9335—Product by special process
- Y10S428/937—Sprayed metal
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/12—All metal or with adjacent metals
- Y10T428/12014—All metal or with adjacent metals having metal particles
- Y10T428/12028—Composite; i.e., plural, adjacent, spatially distinct metal components [e.g., layers, etc.]
- Y10T428/12042—Porous component
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/12—All metal or with adjacent metals
- Y10T428/12493—Composite; i.e., plural, adjacent, spatially distinct metal components [e.g., layers, joint, etc.]
- Y10T428/12736—Al-base component
- Y10T428/12764—Next to Al-base component
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/12—All metal or with adjacent metals
- Y10T428/12493—Composite; i.e., plural, adjacent, spatially distinct metal components [e.g., layers, joint, etc.]
- Y10T428/12771—Transition metal-base component
- Y10T428/12806—Refractory [Group IVB, VB, or VIB] metal-base component
- Y10T428/12812—Diverse refractory group metal-base components: alternative to or next to each other
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/10—Scrim [e.g., open net or mesh, gauze, loose or open weave or knit, etc.]
- Y10T442/102—Woven scrim
- Y10T442/109—Metal or metal-coated fiber-containing scrim
- Y10T442/11—Including an additional free metal or alloy constituent
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Plasma & Fusion (AREA)
- Metallurgy (AREA)
- General Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Structural Engineering (AREA)
- Coating By Spraying Or Casting (AREA)
- Turbine Rotor Nozzle Sealing (AREA)
- Other Surface Treatments For Metallic Materials (AREA)
- Laminated Bodies (AREA)
- Ceramic Products (AREA)
- Road Signs Or Road Markings (AREA)
Description
Fremgangsmåte ved fremstilling av
5-fenyl-1,4-3H-benzodiazepin-2(1H)-oner.
Foreliggende oppfinnelse angår en forbedret fremgangsmåte ved fremstilling av 5-fenyl-1,4-3H-benzodiazepin-2(1H)-oner og substituerte 5-fenyl-1,4-3H-benzodiazepin-2(1H)-oner og mere spesielt fremstilling av 5-f enyl-1 ,Z4.-3H-benzodiazepin-2( 1H)-oner substituert på den ene og/eller den annen av de aromatiske ringer. Den angår videre en forbedret fremgangsmåte ved fremstilling av nevnte forbindelser som er substituert på amido-N-atomet og/eller i 3-stilling.
Disse diazepinonforbindelser har følgende generelle formel:
hvor R^ er hydrogen, methyl eller ethyl, og R2 og R^ er hydrogen, methyl, halogenmethyl, methoxy, nitro eller halogen, og er hydrogen, lavere alkyl, aryl eller aralkyl med 1 eller 2 carbonatomer i alkylenheten.
Diazepinoner av den generelle formel I er nyttige som kjemoterapeutiske midler, særlig for behandling av nervøse lid-elser.
Kjente fremgangsmåter for fremstilling av disse forbindelser innbefatter bl.a. kondensasjon av en 2-aminobenzofenon med gly-cinethylester eller glycinhydroklorid og cyclisering av amino-acetylamid-mellomproduktet (Kanadisk patent nr. 660.724). Det er imidlertid vel kjent at aminolyse av carboxylsyreestere med aromatiske aminer gir dårlige utbytter av de ønskede amider. En annen fremgangsmåte (Kanadisk patent nr. 647.703) beskriver behandling av 2-halogenqacetylamidobenzofenoner med vandige eller organiske oppløsningsmiddeloppløsninger av ammoniakk. Her igjen er utbyttene dårlige på grunn av det velkjente forhold at alkyl-ering av ammoniakk resulterer i en blanding av mono-) di- og tri-substituerte aminer. Nok en metode går ut på å behandle 2-halogenoacetylamidobenzofenoner med flytende ammoniakk ved til-bakeløpstemperaturen av sistnevnte. Skjønt det hevdes at utbyttene er bedre enn for de to tidligere nevnte fremgangsmåter, er prosessen åpenbart upraktisk i stor skala.
I henhold til foreliggende oppfinnelse fremstilles diazepinoner med den generelle formel I ved å behandle fthalimidoacetamider av den generelle formel III
hvor , R^, R^ og R^ har samme betydning som ovenfor angitt,
med hydrazinhydrat,
Denne behandling utføres ved oppvarmnmg, og fortrinnsvis kokning under tilbakeløp, av en blanding av fthalirnidoacetamidet og et passende oppløsningsraiddel i nærvær av minst l molarekvi-valent og fortrinnsvis minst 2 molarekvivalenter, neist. ca. 3 molarekvivalenter av hydrazinhydrat, beregnet på det spesielle fthalimidoacetamid som anvendes. Dette er et forbausende forhold, da det hittil har vært akseptert at en molekvivalent hydrazinhydrat var tilstrekkelig til å fjerne fthaloy1gruppen fra substituerte fthalimider og gi utbytter p°i 90 - 95% primæic? aminei, (ref. H. R» Ing on R. H„ F. Manske - Journal of th>' Chemical Society, 1926, s, 2342). Nar denne metode ble anv<y>ndt for A fjerne fthaloylgruppen fra 2-fthalimidoacetamidobenzofenoner,
fikk man tilbake uforandret utgangsmater ia le nesten kvantitativt selv eftei flere timers kokning under tilbakeløp \ ethnnol. Det viste seg imidlertid at når mengden av hydrazinhydr at ble øke' til minst ca. 2 molekvivalenter eller mere, fikk man høye utbytter av diazepinoner efter bare ca. 15 minutters reaksjonstide Det synes derfor at den første molekvivalent hydrazinhydrat brukes opp til dannelsen av et kortlivet hydrazon og derfor ikke kan utnyttes for å spalte av fthaloylgruppen, idet bare overskuddet av hydrazinhydrat vil bevirke dette. Den således dannede fri aminogruppe erstatter så hydrazinhydratet ved å danne et mere stabilt cyclisk ketimin. Reaksjonsgangen kan anskueliggjøres som følgers
Egnede oppløsningsmidler er bl.a. de vanlige organiske oppløsningsmidler i hvilke både fthalimidoacetamidet og hydrazinhydratet er i det minste delvis oppløselig, og som er inerte overfor begge disse komponenter. Foretrukne oppløsningsmidler er de lavtkokende lavere alifatiske alkoholer, fortrinnsvis ethanol.
De forbindelser som foreliggende fremgangsmåte særlig tar sikte på å fremstille, er 7-klor-l-methyl-5-fenyl-1,4-3H-benzodiazepin-2(1H)-on, 7-klor-5-fenyl-1,4-3H-benzodiazepin-2(1H)-on og 7-klor-l-methyl-3-(p-hydroxybenzyl)-5-fenyl-1,4-3H-benzodiazepin-2(lH)-on som fåes ved som utgangsmateriale å anvende hen-holdsvis 2-(N-methyl)-fthalimidoacetamido-5-klorbenzofenon, 2-fthalimidoacetamido-5-klorbenzofenon og 2-[N-methyl-a-fthalimido-p-( p-hydroxyf enyl) -propionamido ]-5-klorbenzofenon.
Diazepinoner av høy renhet og i utmerket utbytte fåes under ideelle betingelser (dvs. tilbakeløpstemperaturer for oppløs-ningsmidler som ethanol) ved foreliggende fremgangsmåte. Frem-gangsmåtens overlegenhet fremgår klart av følgende sammenligning
av utbytter av 7-klor-l-methyl-5-fenyl-1,4-3H-benzodiazepin-2(lH)-on når det fremstilles ved kjente metoder og metoden ifølge foreliggende oppfinnelse;
Målet for foreliggende oppfinnelse er derfor å skaffe en forbedret fremgangsmåte ved fremstilling av diazepinoner av den generelle formel I.
De nye fthalimidoacetamid-utgangsmateriaJer av den generelle formel II kan fremstilles ved å kondensere en 2-aminobenzofenon av den generelle formel III: hvor R^, R2 og R^ er som angitt ved formel I med et halogenid av en a-fthalimido-carboxylsyre av den generelle formel IV:
hvor R^ er som angitt ved formel I og hvor X er halogen, fortrinnsvis klor eller brom, i nærvær eller i fravær av en alkalisk hydrohalogenid-binder. Kondensasjonene utføres i passende opp-løsningsmidler i hvilke minst én komponent er oppløselig, f,eks. kloroform, methylenklorid eller pyridin, idet oppløsningsmidlet er inert overfor reaktantene, ved temperaturer fra værelsetemperatur til tilbakeløpstemperaturen for det anvendte oppløsnings-middel. Reaksjonsproduktene isoleres lett fra reaksjonsbland-ingene ved kjente fremgangsmåter, f.eks. ved å xedusere volumet av oppløsningsmidlet og avkjøle, hvorved de lett krystalliserer og kan fraskilles ved filtrering. Eller oppløsningsmidlet fjernes helt fra reaksjonsblandingen og krystallisasjonen av residuet bevirkes ved behandling med et annet oppløsningsmiddel. I alminnelighet behøves bare en omkrystallisasjon for å få pro-dukter av analytisk renhet.
De nye fthalimidoacetamider ifølge den generelle formel II kan også fåes ved kondensasjon av en acylert 2-aminobenzofenon i hvilken acylgruppen har et halogenatom i a-stilling, som angitt ved følgende generelle formel Vs hvor R^f R2, R^ og R^ er som angitt for formel I, og hvor X er halogen, fortrinnsvis klor eller brom, med fthalimid eller fortrinnsvis et alkalimetallsalt derav, såsom fthalimidkalium. Produktene isoleres ved de vanlige metoder som beskrevet ovenfor, og er i alle henseender identisk med dem som fåes ved den første metode.
De følgende eksempler er for å belyse oppfinnelsen.
Eksempel 1
7- klor- l- methyl- 5- fenyl- 1, 4- 3H- benzodiazepin- 2( 1H)- on
En oppløsning av 0,5 g 2-(N-methylfthalimidoacetamido)-5-klorbenzofenon i 25 ml 95%-ig ethanol inneholdende 0,174 9 hydrazinhydrat ble oppvarmet under tilbakeløp i 2 timer. Ca.
10 ml ethanol ble så avdestillert. Den blakkede reaksjonsbland-ing ble avkjølt til værelsetemperatur og filtrert. Filtratet ble gjort surt ved tilsetning av 5%-ig saltsyre, blandingen ble oppvarmet til 70 - 80°C og straks avkjølt til værelsetemperatur. Den ble gjort alkalisk med fortynnet natriumhydroxyd og grundig ekstrahert med methylenklorid. Ekstraktet ble vasket med vann, oppløsningsmidlet fjernet ved destillasjon, og den gjenværende 7-klor-l-methyl-5-f enyl-1,4-3H-benzodiazep.in-2( 1H) -on (0,27 g, 82% av det teoretiske) ble omkryst allisert fra ether. Det rene produkt smeltet ved 130°Co
Eksempel 2
7- klor- 5- fenyl- 1, 4- 3H- benzodiazepin- 2( 1H)- on
En suspensjon av 3»02 g 2-fthalimidoacetamido-5-klor-benzofenon i 75 ml ethanol inneholdende 1,08 g hydrazinhydrat ble omrørt og oppvarmet under tilbakeløp i 90 minutter. Efter av-kjøling til værelsetemperatur ble reaksjonsblandingen gjort sur med fortynnet saltsyre, varmet i vannbad i 15 minutter, avkjølt til værelsetemperatur og filtrert. Filtratet ble gjort alkalisk med fortynnet natriumhydroxyd og grundig ekstrahert med kloroform. Fjernelse av oppløsningsmidlet efterlot et høyt utbytte av 7-klor-5-f enyl-1,4-3H-benzodiazepin-2( 1H)->on, som ble omkryst allisert fra aceton. Smeltepunkt 200 - 201°C.
Eksempel 3
7- klor- »3. 5- dif enyl- 1, 4- 3H- benzodiazepin- 2 ( 1H) - on
En oppløsning av 28 g 2-fthalimido-fenylacetamido-5-klor-benzofenon i 300 ii ethanol inneholdende 9,2 g hydrazinhydrat ble oppvarmet under tilbakeløp i 2 timer. Efter avkjøling ble det utfelte, krystallinske materiale oppsamlet ved filtrering, suspendert i 15%-ig vandig natriumhydroxyd og omrørt i 30 minutter ved værelsetemperatur, hvorved fthalylhydrazin gikk i opp-løsning. De uoppløste 13,4 9 7-klor-3,5-difenyl-1,4-3H-benzodiazepin-2(1H)-on ble vasket med vann og ænset ved krystallisasjon fra "Cellosolve". Smeltepunkt 273°C.
Eksempel 4
7- klo r- 1- met hy1- 3. 5- difenyl- 1, 4- 3H- benzodiazepin- 2( 1H)- on
En oppløsning av 13,1 9 2-(N-methyl)-fthaliraidofenylacet-amido-5-klorbenzofenon i 150 ml ethanol inneholdende 4,15 9 hydrazinhydrat ble oppvarmet under tilbakeløp i 90 minutter. Reaksjonsblandingen ble avkjølt, det krystallinske bunnfall oppsamlet ved filtrering, suspendert i fortynnet, vandig natriumhydroxyd og omrørt i 30 minutter ved værelsetemperatur. Det u-oppløste produkt ble oppsamlet ved filtrering og \asket med vann. Utbyttet var 6,5 g« Den rene 7-klor-l-methyl-3,5-difenyl-1,4-3H-benzodiazepin-2(1H)-on hadde et smeltepunkt på 223-224°C
efter krystallisasjon fra methanol-benzen.
Eksempel 5
7- klor- 3- methyl- 5- fenyl- 1. 4- 3H- benzodiazepin- 2( lH)- on
En oppløsning av 17,3 9 2-(a-fthalimido-propionamido)-5-klorbenzofenon i 200 ml ethanol inneholdende 6,85 9 hydrazinhydrat ble oppvarmet under tilbakeløp i 2 timer. Det krystallinske bunnfall ble fjernet ved filtrering og vasket med ethanol. For-tynning av det forenede filtrat og vaskevann med vann bevirket feining av reaksjonsproduktet (3,1 g), som hadde et smeltepunkt på 2l6°C. Ytterligere 3,5 g av det samme produkt ble erholdt når det første krystallinske bunnfall, som for det meste inneholdt fthalylhydrazid, ble suspendert i fortynnet, vandig natriumhydroxyd og omrørt for å fjerne hydrazidet. De forenede utbytter av 7-klor-3-methyl-5-fenyl-l,4-3H-benzodiazepin-2(lH)-on ble renset ved krystallisasjon fra ethanol og hadde smeltepunkt 224 - 225°C.
Eksempel 6
7-klor-l-methyl-3-(p-hydroxybenzyl.)-5-f enyl-1,4-3H-benzodiazepin-2( lH)- on
En oppløsning av 7 9 2-(N-methyl-a-f thalimido-|3-(p-hydroxyfenyl)-propionamido)-5-klorbenzofenon i 100 ml ethanol inneholdende 2,1 g hydrazinhydrat ble oppvarmet under tilbakeløp i 2 timer. Efter avkjøling ble det hvite bunnfall fjernet ved filtrering og vasket med alkohol. De forenede filtrater og vaskevann ble syret med 5%-ig saltsyre, oppløsningen ble oppvarmet til 6o°C, avkjølt til værelsetemperatur, fortynnet med vann og gjort basisk med vandig natriumhydroxyd. Den krystallinske 7-klor-l-methyl-3-(p-hydroxybenzyl)-5-fenyl-1,4-3H-benzodiazepin-2(lH)-on (4,7 g) ble renset ved krystallisasjon fra methanol og hadde smeltepunkt 217 - 2l8°C.
Eksempel 7
5- fenyl- l. 4- 3H- benzodiazepin- 2f1H)- on
Utqanqsmateriale; 2- fthalimidoacet amidobenzof enon
Til 150 ml av en toluenoppløsning av 22,3 g fthalimidoacetylklorid ble tilsatt 19,7 g 2-aminobenzofenon. Efter tilbake-løpskokning i 2 timer ble reaksjonsblandingen inndampet, og det krystallinske 2-fthalimidoacetamidobenzofenon som utgjorde 31 9 (83%) og smeltet ved 148 - 151<0>C,ble frafiltrert.
Sluttprodukt: 5- fenyl- l . 4- 3, H- Denzodiazepin- 2( 1H) - on
En suspensjon av 30,3 9 2-fthalimidoacetamidobenzofenon i 300 ml ethanol inneholdende 14 g 85%-ig hydrazinhydrat ble om-rørt og oppvarmet under tilbakeløp i 2 timer. Efter avkjøling til værelsetemperatur ble det utfelte fthalylhydrazid frafiltrert. Filtratet ble fortynnet med vann, gjort alkalisk med vandig natriumhydroxyd og ekstrahert med kloroform. Oppløsningsmidlet ble fordampet i vakuum og residuet krystallisert fra ethylacetat. Det erholdte 5-fenyl-l,4-3H-benzodiazepin-2(1H)-on som utgjorde 15 g (80%), hadde et smeltepunkt på 182 - l83°C efter omkrystallisasjon fra aceton.
E^ ksempel 8
7- brom- 5- fenyl- 1. 4- 3H- benzodiazepin- 2( lH)- on
Utqanqsmateriale: 2- fthalimidoacetamido- 5- brombenzofenon
Til 50 ml av en toluenoppløsning inneholdende 6,7 g fthalimidoacetylklorid ble tilsatt 8,3 g 2-amino-5-brombenzo-
fenon. Efter tilbakeløpskokning i 2 timer ble reaksjonsbland-
ingen avkjølt, og det krystallinske 2-fthalimidoacetamido-5-
brombenzofenon ble frafiltrert. Utbytte: 11,8 g (85%) med smelte-
punkt 236 - 238°C.
Sluttprodukt: 7- orom- 5- fenyl - 1, 4- 3H- benzodiazepin- 2( 1H)- on
En suspensjon av 10 g 2-fthalimidoacetamido-5-brombenzo-
fenon i 100 ml ethanol inneholdende 5 g 85%-ig hydrazinhydrat ble omrørt og oppvarmet under tilbakeløp i 2 timer. Efter avkjøling til værelsetemperatur ble det utfelte fthalylhydrazid frafil-
trert. Filtratet ble fortynnet med vann, gjort alkalisk med vandig natriumhydroxyd og ekstrahert med kloroform. Kloroformen ble fjernet i vakuum, og residuet ble krystallisert fra methanol„
Man fikk 4,58 g (67,3%) 7-brora-5-fenyl-1,4-3H-benzodiazepin-
2(lH)-on med smeltepunkt 220 - 221°C.
Claims (2)
1. Fremgangsmåte ved fremstilling av 5-fenyl-1,4-3H-benzo-d:Lazepin-2( 1H)-oner av den generelle formel I:
hvor Rj^ er hydrogen, methyl eller ethyl, R2 og R- er hydrogen, methyl, halogenmethyl, methoxy, nit ro eller halogen, og R^ er hydrogen, lavere alkyl, aryl eller aralkyl med 1 eller 2 carbonatomer i alkylenheten,
karakterisert ved at en 2-fthalimidoacyl-amidobenzofenon av den generelle formel II:
hvor R^, R2, R^ og R/^ er som ovenfor angitt, behandles med minst 1 molekvivalent hydrazinhydrat, fortrinnsvis i et egnet oppløs-ningsmiddel, spesielt ethanol*
2. Fremgangsmåte ifølge krav 1,
karakterisert ved at blandingen oppvarmes i nærvær av minst 2, fortrinnsvis ca. 3 molekvivalenter hydrazinhydrat, beregnet på 2-fthalimido-acylamidobenzofenonen.
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-
1979
- 1979-05-11 US US06/038,042 patent/US4273824A/en not_active Expired - Lifetime
-
1980
- 1980-03-12 CA CA000347540A patent/CA1162796A/en not_active Expired
- 1980-04-02 BE BE0/200082A patent/BE882592A/fr not_active IP Right Cessation
- 1980-04-03 AU AU57176/80A patent/AU530303B2/en not_active Ceased
- 1980-04-11 GB GB8012060A patent/GB2049484B/en not_active Expired
- 1980-04-15 NO NO801084A patent/NO156328C/no unknown
- 1980-04-15 FR FR8008365A patent/FR2456079A1/fr active Granted
- 1980-04-16 IL IL59849A patent/IL59849A/xx unknown
- 1980-04-18 NL NL8002263A patent/NL8002263A/nl active Search and Examination
- 1980-04-24 DE DE19803015867 patent/DE3015867A1/de active Granted
- 1980-04-29 SE SE8003254A patent/SE445452B/sv not_active IP Right Cessation
- 1980-04-30 JP JP55058574A patent/JPS6037788B2/ja not_active Expired
- 1980-05-02 IT IT21734/80A patent/IT1131119B/it active
- 1980-05-05 DK DK195280A patent/DK195280A/da unknown
- 1980-05-10 KR KR1019800001846A patent/KR830001651B1/ko active
- 1980-05-10 ES ES491380A patent/ES491380A0/es active Granted
Also Published As
Publication number | Publication date |
---|---|
KR830001651B1 (ko) | 1983-08-22 |
IL59849A0 (en) | 1980-06-30 |
SE8003254L (sv) | 1980-11-12 |
IT1131119B (it) | 1986-06-18 |
NO801084L (no) | 1980-11-12 |
DK195280A (da) | 1980-11-12 |
DE3015867C2 (no) | 1991-11-14 |
DE3015867A1 (de) | 1980-11-20 |
IL59849A (en) | 1984-02-29 |
IT8021734A0 (it) | 1980-05-02 |
KR830002660A (ko) | 1983-05-30 |
CA1162796A (en) | 1984-02-28 |
NL8002263A (nl) | 1980-11-13 |
GB2049484B (en) | 1983-12-14 |
JPS6037788B2 (ja) | 1985-08-28 |
BE882592A (fr) | 1980-07-31 |
FR2456079B1 (no) | 1984-12-21 |
AU530303B2 (en) | 1983-07-07 |
GB2049484A (en) | 1980-12-31 |
JPS55154587A (en) | 1980-12-02 |
FR2456079A1 (fr) | 1980-12-05 |
NO156328C (no) | 1987-09-02 |
ES8104753A1 (es) | 1981-05-16 |
ES491380A0 (es) | 1981-05-16 |
US4273824A (en) | 1981-06-16 |
SE445452B (sv) | 1986-06-23 |
AU5717680A (en) | 1980-11-13 |
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