NO166557B - Innretning for omstabling av en bladstabel. - Google Patents
Innretning for omstabling av en bladstabel. Download PDFInfo
- Publication number
- NO166557B NO166557B NO86862810A NO862810A NO166557B NO 166557 B NO166557 B NO 166557B NO 86862810 A NO86862810 A NO 86862810A NO 862810 A NO862810 A NO 862810A NO 166557 B NO166557 B NO 166557B
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- Prior art keywords
- housing
- derivatives
- acid
- compound
- diphenylcyclopropane
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- YHPLHTWUZJURAM-UHFFFAOYSA-N (1-phenylcyclopropyl)benzene Chemical class C1CC1(C=1C=CC=CC=1)C1=CC=CC=C1 YHPLHTWUZJURAM-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 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 class [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 230000000717 retained effect Effects 0.000 abstract 1
- 230000032258 transport Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VFSFCYAQBIPUSL-UHFFFAOYSA-N cyclopropylbenzene Chemical class C1CC1C1=CC=CC=C1 VFSFCYAQBIPUSL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002322 anti-exudative effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001152 anti-nicotinic effect Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 210000001103 thalamus Anatomy 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
- G03B23/00—Devices for changing pictures in viewing apparatus or projectors
- G03B23/02—Devices for changing pictures in viewing apparatus or projectors in which a picture is removed from a stock and returned to the same stock or another one; Magazines therefor
-
- 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
- Y10S414/00—Material or article handling
- Y10S414/10—Associated with forming or dispersing groups of intersupporting articles, e.g. stacking patterns
- Y10S414/112—Group formed or dispensed by reversible apparatus
Description
Fremgangsmåte ved fremstilling av nye, tera-
peutisk aktive difenylcyclopropanderivater.
Foreliggende oppfinnelse angår en fremgangsmåte til fremstill-
ing av nye, terapeutisk virksomme difenylcyclopropanderivater av den generelle formel:
hvor R^ er hydrogen, en forgrenet eller uforgrenet alkylgruppe med 1-4 carbonatomer, eller en hydroxyalkylgruppe med 1-3 carbon-
atomer,
R2 er en forgrenet eller uforgrenet alkylgruppe med 1 - q- carbonatomer, eller en cyclohexylgruppe, samt deres salter med i farmakologisk henseende akseptable organiske og uorganiske syrer og med lavere alkylhalogenider. .Forbindelsene som fremstilles i henhold til fremgangsmåten ifølge oppfinnelsen, kan foreligge som cis-cis-, cis-trans- og trans-trans-geometriske isomere og dessuten som d,l og dl optiske isomere. Oppfinnelsen omfatter fremstilling av de separerte geometriske isomere og deres isolerte optiske isomere såvel som blandinger derav.
Fremgangsmåten ifølge oppfinnelsen utmerker seg ved at en forbindelse av formelen:
hvor R^ har den ovenfor angitte betydning, omsettes med en forbindelse av formel R2V hvor R har den ovenfor angitte betydning, og Y ér halogen, og den erholdte forbindelse, om ønsket, omsettes med en syre eller et alkylhalogenid for dannelse av det tilsvarende salt.
Reaksjonen utføres fortrinnsvis i et forseglet rør ved tempera-turer høyere enn 50 oC i nærvær av et syrebindende middel og et egnet oppløsningsmiddel.
Syreaddisjonssaltene kan fremstilles på den vanlige måte, dvs. ved at man omsetter basen med enten den støkiometriske mengde organisk eller uorganisk syre i et med vann blandbart oppløsnings-middel, såsom aceton eller ethanol, med isolering av saltet ved kon-sentrering og avkjøling, eller med et overskudd av syren i et med vann ikke blandbart oppløsningsmiddel, såsom ethylether eller kloro-form, i hvilket tilfelle saltet utskilles direkte. Disse salter kan også fremstilles efter den konvensjonelle metode med dobbel spalt-ning av egnede salter, hvilken metode er vel kjent i faget.
De foretrukne syrer er de som danner ikke-toksiske salter. Eksempler på sådanne syrer er saltsyre, bromhydrogensyre, svovelsyre, sitronsyre, eddiksyre, vinsyre, maleinsyre og toluensulfonsyre.
Også de kvartære ammoniumsalter kan fremstilles på konvensjonell måte ved at man omsetter det tertiære amin med et laverealkyl-halogenid, såsom methylbromid eller methyljodid i et forseglet rør med eller uten anvendelse av inert oppløsningsmiddel.
Den foretrukne metode for fremstilling av de som utgangsmateri-aler anvendte forbindelser av formel (II) er beskrevet i norsk patent-søknad nr. 166.556.
Fra nederlandsk patentansøkning nr, 64.12766 er kjent substituerte monofenylcyclopropanderivater. Disse substituerte amino-derivater utviser, avhengig av substituentenes natur, en stimulering av sentralnervesystemet og/eller påvirker den periferale neuro-vegetative seksjon og/eller fremkaller uterus-stimulerende aktivitet og/eller en utpreget ant i-exudativ aktivitet og/eller ant i-inflamma-torisk aktivitet og/eller appetittnedsettende aktivitet og/eller anti-nikotinisk aktivitet, og/eller anti-mikrobiell aktivitet .
De nye difenylcyclopropanderivater som fremstilles i henhold til, oppfinnelsen, oppviser verdifulle farmakologiske egenskaper og har temmelig lav toksisitet.
Forbindelsene virker stimulerende på sentralnervesystemet. Deres aktivitet er meget høy og er påvist på mus, rotter og kaniner enten ved endringer i dyrenes oppførsel eller på indirekte måte ved motvirkning av depresjonsvirkningen som fremkalles av reserpin, pargilin eller barbiturater. Denne antidepresjonsvirkning er ikke forbundet med monoamin-oxidase-inhiberende egenskaper.
Spesielt oppviser 1-(N-methyl)-aminomethyl-2 , 3-cis ,t rans-difenyl-cyclopropan en høy antidepressiv virkning. Denne forbindelse ble testet også ved at man målte endringene i pysostigmin-fremkalt EEG vekningsreaksjon i kaniner som var ved bevissthet og som var innpodet corticale og subcorticale (hippocampus, thalamus) elek-troder efter administrering av 2 - 5 mg/kg av den ovennevnte forbindelse. Den dødelige dose for mus er større enn lOO mg/kg kropps-vekt, mens en daglig oral dose på 50 mg/kg i to måneder tåles godt av rotter. Disse toksikologiske data er meget gunstige, tatt i be-traktning at den effektive enhetsdose er ca. 10 - 50 mg for mennesker.
Forbindelsene som fremstilles ifølge oppfinnelsen, og deres i farmakologisk henseende akseptable salter med organiske og uorganiske syrer og med laverealkylhalogenider kan administreres oralt, parenteralt eller rektalt og kan blandes med faste eller væskeformige bærere i de vanlige farmakologiske former såsom tabletter, kapsler, stikkpiller og.skåler.
De nye difenylcyclopropanderivater som fremstilles ifølge foreliggende oppfinnelse, utviser således følgende egenskaper: en depressiv, antihistaminisk, antiserotonisk og antiexudativ effekt.
I journal of Medicinal Chemistry, IO, 1091 (1967) er beskrevet egenskapene for monoarylcyclopropanderivatene samt metoder for vur-dering av disse.
Av det nevnte tidsskrift fremgår det at difenylcyclopropanderivatene ikke utviser de samme egenskaper.som monoarylcyclopropanderivatene, idet difenylcyclopropanderivatene utviser kun ganske få av de farmakologiske egenskaper som utvises av monofenylcyclopropan-derivatene.
I det følgende er det redegjort for. sammenlignende forsøk mellom difenylcyclopropanderivatene og de av monofenylcyclopropan-derivatene som utviser en tilnærmet lik aktivitet som de åpenbart for difenylcyclopropanderivatene.
Den stimulerende aktivitet på sentralnervesystemet er målt ved å bestemme effekten på den spontane motilitet. Denne metode og tolkning av samme er beskrevet i det ovenfor omtalte litteratursted, og de erholdte resultater er vist i tabellen som følger på side 6.
Fra de oppførte data i tabellen er det umiddelbart åpenbart at difenylcyclopropanderivatene i overraskende grad i det vesentlige er mere effektive enn de tilsvarende monofenylcyclopropanderivater, og at mange av de fremstilte difenylcyclopropanderivater ikke har noen korresponderende kjent forbindelse i monofenylcyclopropanderivatserien.
Forbindelsene som fremstilles ifølge oppfinnelsen, og deres i farmakologisk henseende akseptable salter med organiske og uorganiske syrer og med laverealkylhalogenider kan administeres oralt, parenteralt eller rektalt og kan blandes med faste eller væskeformige bærere i de vanlige farmasøytiske former såsom tabletter, kapsler, stikkpiller og skåler.
Eksempel 1
1-( N, N- diethyl)- aminomethyl- 2, 3- cis. trans- difenyl- hydroklorid
800 ml ethylether ble tilsatt 95 g (0,33 mol) l-(N-ethyl)-aminomethyl-2,3-cis,trans-difenyl-hydroklorid oppløst i 9O0 ml vann. Til denne blanding som ble holdt;avkjølt ved 5°C under omrøring, ble der tildryppet samtidig en oppløsning av 27 g (0,68 mol) natrium-
hydroxyd i 200 ml vann og 55,5 (0,35 mol) ethyljodid. Blandingen ble omrørt i ytterligere 1 time, mens temperaturen ble tillatt å øke til romtemperatur. Etherskiktét ble fraskilt og den vandige oppløs-ning vasket med ethylether. Etherekstraktet og ethervaske-væskene
ble slått sammen og vasket med vann, deretter tilsatt dråpevis kon-sentrert saltsyre, og det utskilte hydroklorid ble vasket med vann, og omkrystallisert fra isopropylalkohol.
Smp. = 175° - 177°C; "Acidimetrisk verdi" =99,7%
P<Ka>24,50°C<=> 9'65
Analyse: beregnet for C^H^CIN: C 76,05; H 8,30; N 4,43; Cl 11,22
funnet: C 75,73; H 8,33; n 4,44; Cl 11,25
Eksempel 2
Ved anvendelse av fremgangsmåten som beskrevet i eksempel 1 ble følgende forbindelser fremstilt: 1-( N- ethyl)- aminomethyl- 2, 3- cis, t rans- difenylcyclopropan Kp. = 120° - 130°C/0,1 mm; "Acidimetrisk verdi" = 99,24%
PKb26<o>c= 4,245;nJ° = 1,5753
Analyse: beregnet for C^H^N: C 86,01; H 8,42; N 5, 57
funnet: C 85,95; H 8,27; N 5,72
Hydrokloridsaltet smeltet ved 134° - 135°C (fra ethylalkohol).
1-( N, N- dimethyl)- aminomethyl- 2, 3- cis, t rans- difenylcyclopropan Kp. = 147° - 150°C/l mm; "Acidimetrisk verdi" = 99,43%
pKa26)5oc 8,00; n^° = 1,5768
Ultrafiolett absorpsjonstopp av en methanoloppløsning (3,06,10~^M/l)
ved 22 3 nm E = 19.620
Analyse: beregnet for C-^H^N: C 86,01; H 8,42; N 5,57
funnet: C 85,77; H 8,48; N 5,6l Hydrokloridsaltet smeltet ved 190° - 192°C (fra ethylalkohol).
Claims (1)
- Fremgangsmåte ved fremstilling av nye terapeutisk virksomme difenylcyclopropanderivater av den generelle formel:hvor R^ betegner hydrogen, én uforgrenet eller forgrenet alkylgruppe med 1-4 carbonatomer, eller en hydroxyalkylgruppe med 1-3 carbonatomer,R2 betegner en uforgrenet eller forgrenet alkylgruppe med 1-4 carbonatomer, eller en cyclohexylgruppe, samt deres salter med i farmakologisk henseende akseptable organiske og uorganiske syrer og med laverealkylhalogenider,karakterisert ved at en forbindelse av formelenhvor R^ har den ovenfor gitte betydning, omsettes med en forbindelse av formelenhvor R2 har den ovenfor gitte betydning, og Y er halogen, i nærvær av en syrebindende forbindelse, og eventuelt omsetter den erholdte forbindelse med en syre eller et alkylhalogenid for fremstilling av det tilsvarende salt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843441464 DE3441464A1 (de) | 1984-11-13 | 1984-11-13 | Vorrichtung zum zyklischen umschichten eines blattstapels |
| PCT/EP1985/000606 WO1986003020A1 (en) | 1984-11-13 | 1985-11-12 | Device for rearranging a pile of sheets |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO862810D0 NO862810D0 (no) | 1986-07-11 |
| NO862810L NO862810L (no) | 1986-07-11 |
| NO166557B true NO166557B (no) | 1991-04-29 |
| NO166557C NO166557C (no) | 1991-08-07 |
Family
ID=6250188
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO86862813A NO166980C (no) | 1984-11-13 | 1986-07-11 | Beholder for opptak av en bildestabel. |
| NO86862809A NO166060C (no) | 1984-11-13 | 1986-07-11 | Innretning for syklisk omstabling av en bladstabel. |
| NO86862815A NO166429C (no) | 1984-11-13 | 1986-07-11 | Beholder for en bladstabel. |
| NO86862819A NO862819L (no) | 1984-11-13 | 1986-07-11 | Innretning for omstabling av en stabel bilder. |
| NO86862810A NO166557C (no) | 1984-11-13 | 1986-07-11 | Innretning for omstabling av en bladstabel. |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO86862813A NO166980C (no) | 1984-11-13 | 1986-07-11 | Beholder for opptak av en bildestabel. |
| NO86862809A NO166060C (no) | 1984-11-13 | 1986-07-11 | Innretning for syklisk omstabling av en bladstabel. |
| NO86862815A NO166429C (no) | 1984-11-13 | 1986-07-11 | Beholder for en bladstabel. |
| NO86862819A NO862819L (no) | 1984-11-13 | 1986-07-11 | Innretning for omstabling av en stabel bilder. |
Country Status (15)
| Country | Link |
|---|---|
| US (7) | US4745697A (no) |
| EP (6) | EP0201550B1 (no) |
| JP (5) | JPS62500812A (no) |
| KR (5) | KR880700309A (no) |
| AT (4) | ATE49811T1 (no) |
| AU (5) | AU574253B2 (no) |
| BR (5) | BR8507044A (no) |
| CA (4) | CA1258972A (no) |
| DE (5) | DE3441464A1 (no) |
| DK (5) | DK152314C (no) |
| ES (5) | ES296326Y (no) |
| GB (5) | GB2182021A (no) |
| NO (5) | NO166980C (no) |
| WO (5) | WO1986003021A1 (no) |
| ZA (5) | ZA858711B (no) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3441464A1 (de) * | 1984-11-13 | 1986-10-02 | Licinvest Ag, Chur | Vorrichtung zum zyklischen umschichten eines blattstapels |
| DE3441488A1 (de) * | 1984-11-13 | 1986-08-21 | Licinvest Ag, Chur | Vorrichtung zum zyklischen umschichten eines blattstapels |
| US4939860A (en) * | 1984-11-13 | 1990-07-10 | Licinvest Ag | Cyclic rearrangement device for stacked rectangular sheets |
| DE3539339A1 (de) * | 1985-11-06 | 1987-05-07 | Licinvest Ag | Behaelter fuer einen bilderstapel |
| DE3539297A1 (de) * | 1985-11-06 | 1987-05-07 | Licinvest Ag | Behaelter zur aufnahme eines bilderstapels |
| DE3631212A1 (de) * | 1986-07-18 | 1988-03-24 | Licinvest Ag | Schuber fuer eine fotokassette |
| US5193795A (en) * | 1987-11-21 | 1993-03-16 | Licinvest Ag | Device for the cyclic rearrangement of a pile of sheets |
| DE3739499A1 (de) * | 1987-11-21 | 1989-06-01 | Licinvest Ag | Blattwechsler |
| DE3739500A1 (de) * | 1987-11-21 | 1989-06-01 | Licinvest Ag | Vorrichtung zum zyklischen umschichten eines blattstapels |
| GB2243457A (en) * | 1990-04-27 | 1991-10-30 | Brilliant Enterprise Corp | A picture display frame |
| US5301443A (en) * | 1990-09-12 | 1994-04-12 | Gori Leon M | Shopping cart handle advertising display device |
| BR9303963A (pt) * | 1992-01-25 | 1994-08-02 | Licinvest Ag | Dispositivo para reagrupar ciclicamente uma pilha de folhas |
| DE4215019A1 (de) * | 1992-05-13 | 1993-11-18 | Licinvest Ag Landquart | Vorrichtung zum zyklischen Umschichten eines Blattstapels |
| US5609252A (en) * | 1995-04-21 | 1997-03-11 | View 'n Store, Inc. | Photograph display and storage tray system |
| BR9805193A (pt) * | 1998-11-18 | 2000-06-06 | Vanderlei Francisco Ventrici | Porta retrato múltiplo |
| US7320413B2 (en) * | 2004-06-08 | 2008-01-22 | Fusi John C | Self-closing dispensing container |
| JP4729313B2 (ja) * | 2005-02-08 | 2011-07-20 | エム・エフ・ヴィ株式会社 | シート状物収納容器 |
| CN103692815B (zh) * | 2014-01-04 | 2016-03-23 | 华北理工大学 | 移动式文件盒 |
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| US2577366A (en) * | 1947-03-26 | 1951-12-04 | Dev & Design Inc | Machine for displaying rugs |
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| US3234673A (en) * | 1964-06-01 | 1966-02-15 | Robert H Cook | Card index case |
| US3377727A (en) * | 1966-06-01 | 1968-04-16 | John H. Weggeland | Picture viewer |
| US3495345A (en) * | 1967-05-12 | 1970-02-17 | John H Weggeland | Picture viewer |
| GB1221442A (en) * | 1967-08-02 | 1971-02-03 | Maurice Grosse | Improvements in or relating to display devices |
| GB1200387A (en) * | 1967-11-06 | 1970-07-29 | Cincinnati Milling Machine Co | Copper clad plastic panel |
| US3500679A (en) * | 1968-07-29 | 1970-03-17 | William P Smith | Weld testing device |
| US3696537A (en) * | 1969-11-04 | 1972-10-10 | Ronald D Alleman | Skip frame visual display device |
| GB1377607A (en) * | 1970-11-27 | 1974-12-18 | Measuring Process Control Ltd | Testing and grading of timber |
| FR2134724A5 (no) * | 1971-04-19 | 1972-12-08 | Naguet Pierre | |
| DE2240452B2 (de) * | 1971-08-26 | 1979-10-04 | Polyair Maschinenbau Gmbh, Kittsee, Burgenland (Oesterreich) | Meßanordnung zur Prüfung der Biegebeanspruchung elastischer Stoffe |
| US3797144A (en) * | 1972-09-07 | 1974-03-19 | Wml | Display-type picture viewer |
| US4057920A (en) * | 1975-11-24 | 1977-11-15 | Weggeland John H | Picture viewer with successive feed means |
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| DE2742346C3 (de) * | 1977-09-20 | 1980-04-17 | Licinvest Ag, Chur (Schweiz) | Bildbetrachtungsgerät |
| DE2742345C3 (de) * | 1977-09-20 | 1981-08-06 | Licinvest Ag, Chur | Bildbetrachtungsgerät mit Wechselmechanik |
| DE2742349C3 (de) * | 1977-09-20 | 1981-06-25 | Licinvest Ag, Chur | Bildbetrachtungsgerät |
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| DE2742347C2 (de) * | 1977-09-20 | 1984-01-26 | Licinvest AG, 7002 Chur | Behälter für Fotoabzüge |
| DE2745214C3 (de) * | 1977-10-07 | 1984-07-26 | Licinvest Ag, Chur | Vorrichtung zum wechselweisen Exponieren einzelner Blätter aus einem Blattstapel, insbesondere Photobetrachtungswechsler |
| DE2742350C3 (de) * | 1977-09-20 | 1981-06-25 | Licinvest Ag, Chur | Bildbetrachtungsgerät |
| DE2822851A1 (de) * | 1978-05-24 | 1979-11-29 | Licinvest Ag | Vorrichtung zum wechselweisen exponieren einzelner blaetter aus einem blattstapel, insbesondere fotobetrachtungswechsler |
| DE2833410A1 (de) * | 1978-07-29 | 1980-02-14 | Licinvest Ag | Vorrichtung zum wechselweisen exponieren einzelner blaetter aus einem blattstapel, insbesondere photobetrachtungswechsler |
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| DE3441482A1 (de) * | 1984-11-13 | 1986-08-21 | Licinvest Ag, Chur | Vorrichtung zum zyklischen umschichten eines blattstapels |
| DE3441464A1 (de) * | 1984-11-13 | 1986-10-02 | Licinvest Ag, Chur | Vorrichtung zum zyklischen umschichten eines blattstapels |
| DE3441456A1 (de) * | 1984-11-13 | 1986-09-04 | Licinvest Ag, Chur | Vorrichtung zum zyklischen umschichten eines blattstapels |
| US4797144A (en) * | 1987-07-20 | 1989-01-10 | Corning Glass Works | Deep pressing mold and process for molded optical elements |
-
1984
- 1984-11-13 DE DE19843441464 patent/DE3441464A1/de not_active Withdrawn
-
1985
- 1985-11-12 BR BR8507044A patent/BR8507044A/pt not_active IP Right Cessation
- 1985-11-12 BR BR8507040A patent/BR8507040A/pt not_active IP Right Cessation
- 1985-11-12 BR BR8507038A patent/BR8507038A/pt not_active IP Right Cessation
- 1985-11-12 US US06/901,530 patent/US4745697A/en not_active Expired - Fee Related
- 1985-11-12 WO PCT/EP1985/000607 patent/WO1986003021A1/de not_active Application Discontinuation
- 1985-11-12 BR BR8507041A patent/BR8507041A/pt not_active IP Right Cessation
- 1985-11-12 GB GB08616632A patent/GB2182021A/en not_active Withdrawn
- 1985-11-12 WO PCT/EP1985/000609 patent/WO1986003023A1/de active IP Right Grant
- 1985-11-12 JP JP61500006A patent/JPS62500812A/ja active Pending
- 1985-11-12 DE DE8585905626T patent/DE3575615D1/de not_active Expired - Fee Related
- 1985-11-12 AU AU52046/86A patent/AU574253B2/en not_active Ceased
- 1985-11-12 AU AU50672/85A patent/AU580818B2/en not_active Ceased
- 1985-11-12 JP JP60505054A patent/JPS62500808A/ja active Pending
- 1985-11-12 AU AU50197/85A patent/AU582403B2/en not_active Ceased
- 1985-11-12 AT AT85905626T patent/ATE49811T1/de not_active IP Right Cessation
- 1985-11-12 AT AT86900086T patent/ATE50650T1/de not_active IP Right Cessation
- 1985-11-12 WO PCT/EP1985/000610 patent/WO1986003024A1/de active IP Right Grant
- 1985-11-12 GB GB8616656A patent/GB2182022B/en not_active Expired
- 1985-11-12 AU AU52051/86A patent/AU5205186A/en not_active Abandoned
- 1985-11-12 JP JP86500409A patent/JPS62500819A/ja active Pending
- 1985-11-12 EP EP85905626A patent/EP0201550B1/de not_active Expired - Lifetime
- 1985-11-12 EP EP85906052A patent/EP0201595A1/de not_active Withdrawn
- 1985-11-12 CA CA000495142A patent/CA1258972A/en not_active Expired
- 1985-11-12 EP EP85906053A patent/EP0202307B1/de not_active Expired - Lifetime
- 1985-11-12 BR BR8507047A patent/BR8507047A/pt unknown
- 1985-11-12 CA CA000495109A patent/CA1255098A/en not_active Expired
- 1985-11-12 DE DE8686900086T patent/DE3576218D1/de not_active Expired - Fee Related
- 1985-11-12 WO PCT/EP1985/000611 patent/WO1986003025A1/de active IP Right Grant
- 1985-11-12 AU AU53085/86A patent/AU581493B2/en not_active Ceased
- 1985-11-12 EP EP88110192A patent/EP0315733A1/de not_active Withdrawn
- 1985-11-12 US US06/900,149 patent/US4776119A/en not_active Expired - Fee Related
- 1985-11-12 DE DE8585906053T patent/DE3576415D1/de not_active Expired - Fee Related
- 1985-11-12 JP JP60505077A patent/JPS62500809A/ja active Pending
- 1985-11-12 US US06/901,531 patent/US4780976A/en not_active Expired - Fee Related
- 1985-11-12 GB GB8616631A patent/GB2179924B/en not_active Expired
- 1985-11-12 US US06/888,324 patent/US4772168A/en not_active Expired - Fee Related
- 1985-11-12 WO PCT/EP1985/000606 patent/WO1986003020A1/de active IP Right Grant
- 1985-11-12 AT AT85905628T patent/ATE49813T1/de not_active IP Right Cessation
- 1985-11-12 AT AT85906053T patent/ATE50873T1/de not_active IP Right Cessation
- 1985-11-12 EP EP85905628A patent/EP0204729B1/de not_active Expired - Lifetime
- 1985-11-12 DE DE8585905628T patent/DE3575617D1/de not_active Expired - Fee Related
- 1985-11-12 GB GB08616655A patent/GB2179750A/en not_active Withdrawn
- 1985-11-12 JP JP61500001A patent/JPS62500851A/ja active Pending
- 1985-11-12 CA CA000495141A patent/CA1253339A/en not_active Expired
- 1985-11-12 GB GB08616657A patent/GB2179175B/en not_active Expired
- 1985-11-12 CA CA000495130A patent/CA1308557C/en not_active Expired - Fee Related
- 1985-11-12 EP EP86900086A patent/EP0203168B1/de not_active Expired - Lifetime
- 1985-11-13 ZA ZA858711A patent/ZA858711B/xx unknown
- 1985-11-13 ES ES1985296326U patent/ES296326Y/es not_active Expired
- 1985-11-13 ZA ZA858712A patent/ZA858712B/xx unknown
- 1985-11-13 ES ES548828A patent/ES8701673A1/es not_active Expired
- 1985-11-13 ZA ZA858710A patent/ZA858710B/xx unknown
- 1985-11-13 ES ES548835A patent/ES8701120A1/es not_active Expired
- 1985-11-13 ES ES1985296324U patent/ES296324Y/es not_active Expired
- 1985-11-13 ZA ZA858709A patent/ZA858709B/xx unknown
- 1985-11-13 ES ES1985296325U patent/ES296325Y/es not_active Expired
- 1985-11-13 ZA ZA858708A patent/ZA858708B/xx unknown
-
1986
- 1986-07-10 DK DK327986A patent/DK152314C/da not_active IP Right Cessation
- 1986-07-10 DK DK328086A patent/DK155768C/da not_active IP Right Cessation
- 1986-07-10 DK DK328186A patent/DK154108C/da not_active IP Right Cessation
- 1986-07-11 KR KR1019860700447A patent/KR880700309A/ko not_active Application Discontinuation
- 1986-07-11 KR KR1019860700444A patent/KR880700306A/ko not_active Application Discontinuation
- 1986-07-11 KR KR1019860700448A patent/KR880700310A/ko not_active Application Discontinuation
- 1986-07-11 KR KR1019860700446A patent/KR880700308A/ko not_active Application Discontinuation
- 1986-07-11 NO NO86862813A patent/NO166980C/no unknown
- 1986-07-11 NO NO86862809A patent/NO166060C/no unknown
- 1986-07-11 DK DK331186A patent/DK152460C/da not_active IP Right Cessation
- 1986-07-11 KR KR1019860700443A patent/KR880700305A/ko not_active Application Discontinuation
- 1986-07-11 NO NO86862815A patent/NO166429C/no unknown
- 1986-07-11 NO NO86862819A patent/NO862819L/no unknown
- 1986-07-11 NO NO86862810A patent/NO166557C/no unknown
- 1986-07-11 DK DK331686A patent/DK331686D0/da not_active Application Discontinuation
-
1988
- 1988-05-19 US US07/197,304 patent/US4869006A/en not_active Expired - Fee Related
- 1988-07-07 US US07/216,414 patent/US4899475A/en not_active Expired - Fee Related
-
1991
- 1991-01-17 US US07/642,151 patent/US5101588A/en not_active Expired - Fee Related
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