NO131698B - - Google Patents
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- Publication number
- NO131698B NO131698B NO2725/70A NO272570A NO131698B NO 131698 B NO131698 B NO 131698B NO 2725/70 A NO2725/70 A NO 2725/70A NO 272570 A NO272570 A NO 272570A NO 131698 B NO131698 B NO 131698B
- Authority
- NO
- Norway
- Prior art keywords
- pyridyl
- new
- compound
- ethyl
- ethylhydrazine
- Prior art date
Links
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- HMCWZAZLRFMRPY-UHFFFAOYSA-N 2-pyridin-4-ylethylhydrazine Chemical compound NNCCC1=CC=NC=C1 HMCWZAZLRFMRPY-UHFFFAOYSA-N 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 229940040102 levulinic acid Drugs 0.000 claims description 5
- NSLJAVZPTLLIER-UHFFFAOYSA-N 6-methyl-2-(2-pyridin-4-ylethyl)-4,5-dihydropyridazin-3-one Chemical compound O=C1CCC(C)=NN1CCC1=CC=NC=C1 NSLJAVZPTLLIER-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 15
- 230000003213 activating effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl levulinate Chemical compound 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 3
- 229960002456 hexobarbital Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000004913 activation Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940064790 dilantin Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940058352 levulinate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02K—DYNAMO-ELECTRIC MACHINES
- H02K44/00—Machines in which the dynamo-electric interaction between a plasma or flow of conductive liquid or of fluid-borne conductive or magnetic particles and a coil system or magnetic field converts energy of mass flow into electrical energy or vice versa
- H02K44/02—Electrodynamic pumps
- H02K44/06—Induction pumps
Landscapes
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Structures Of Non-Positive Displacement Pumps (AREA)
- General Induction Heating (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Filling Or Discharging Of Gas Storage Vessels (AREA)
- Press Drives And Press Lines (AREA)
- Extraction Or Liquid Replacement (AREA)
- Electromagnetic Pumps, Or The Like (AREA)
Description
Fremgangsmåte til fremstilling av et nytt pyridazinon. Process for the preparation of a new pyridazinone.
Denne oppfinnelse angår en fremgangsmåte til fremstilling av en ny kje-misk forbindelse som aktiverer legemidler som påvirker sentralnervesystemet. This invention relates to a method for producing a new chemical compound that activates drugs that affect the central nervous system.
Den nye forbindelse som fremstilles i henhold til oppfinnelsen og som aktiverer legemidler til påvirkning av sentralnervesystemet for å gjøre dette fysiologisk mer aktivt, er 2-[2-(4-pyridyl)ethyl]-6-me-thyl-4,5-dihydro-3-pyridazinon med formelen: The new compound which is produced according to the invention and which activates drugs to influence the central nervous system to make it physiologically more active, is 2-[2-(4-pyridyl)ethyl]-6-methyl-4,5-dihydro -3-pyridazinone with the formula:
Den aktiverende forbindelse 2-[2-(4-pyridyl)ethyl]-6-methyl-4,5-dihydro-3-pyridazinon med formel I fremstilles ved å la 2-(4-pyridyl)ethylhydrazin reagere med levulinsyre eller en alkylester av denne som f. eks. ethylesteren. The activating compound 2-[2-(4-pyridyl)ethyl]-6-methyl-4,5-dihydro-3-pyridazinone of formula I is prepared by reacting 2-(4-pyridyl)ethylhydrazine with levulinic acid or an alkyl ester of this as e.g. the ethyl ester.
Det skal bemerkes at fremstillingen av It should be noted that the manufacture of
pyridazinoner for å fremstille pyridylsub-stituerte pyridazinoner ved kondensering av et pyridylhydrazin med levulinsyre er i og for seg kjent. pyridazinones to prepare pyridyl-substituted pyridazinones by condensation of a pyridylhydrazine with levulinic acid is known per se.
Ved å arbeide etter oppfinnelsen lar By working according to the invention lar
man fortrinsvis 2-(4-pyridyl)ethylhydra-zin reagere med levulinsyre, hvorpå man one preferably reacts 2-(4-pyridyl)ethylhydrazine with levulinic acid, after which one
fjerner det vann som er dannet ved reak-sjonen, f. eks. ved destillasjon under redusert trykk, og deretter destillerer reaksjonsproduktet. En annen egnet fremgangsmåte består i at man lar 2-(4-pyri-dyl)ethylhydrazin reagere med et alkyl-levulinat; alkoholen fjernes ved destillasjon, og reaksjonsproduktet destilleres. Derpå kan reaksjonsproduktet omkrystalliseres, om ønskes. removes the water formed during the reaction, e.g. by distillation under reduced pressure, and then distills the reaction product. Another suitable method consists in allowing 2-(4-pyridyl)ethylhydrazine to react with an alkyl levulinate; the alcohol is removed by distillation, and the reaction product is distilled. The reaction product can then be recrystallized, if desired.
Man har funnet at den nye forbindelse med formel I kan aktivere legemidler som pentobarbital, hexobarbital, kloralhydrat, klorpromazin, mephenezin, stryknin og di-fenylhydantoin (Dilantin), som påvirker sentralnervesystemet, ved å øke varighe-ten av deres virkning eller ved å gjøre dem virksomme i mindre mengder enn de som kan anvendes når de brukes uten den nye aktiverende forbindelse. It has been found that the new compound of formula I can activate drugs such as pentobarbital, hexobarbital, chloral hydrate, chlorpromazine, mephenezine, strychnine and di-phenylhydantoin (Dilantin), which affect the central nervous system, by increasing the duration of their action or by making them active in smaller amounts than those that can be used when used without the new activating compound.
Den forlengelse av virkningstiden for disse sentralt virkende legemidler som kommer i stand ved at man samtidig med dem eller like før de administreres tilfører dem nye aktiverende forbindelse, er av særlig verdi i forbindelse med kirurgiske og obstetriske arbeider. Senkningen av den dose som normalt kreves for kjente sentralt virkende legemidler for å fremkalle en virkning, således at man oppnår denne virkning med en mindre dose, er en meget verdifull egenskap når der oppstår medi-sinske nødstilstander. The extension of the duration of action of these centrally acting drugs, which is achieved by adding a new activating compound at the same time as them or just before they are administered, is of particular value in connection with surgical and obstetric work. The lowering of the dose that is normally required for known centrally acting drugs to induce an effect, so that this effect is achieved with a smaller dose, is a very valuable property when medical emergencies arise.
Den nye aktiverende forbindelse med formel I viser i seg selv ingen synlig virkning på sentralnervesystemet, og man har ikke iakttatt noen toksiske virkninger som følge av at den er administrert. Dens ver-difulle fysiologiske virkning gjør seg gjel-dende når den tilføres dyr i forbindelse med kjente, sentralt virkende legemidler. Doser av denne forbindelse i en størrelses-orden omkring 40 til ca. 220 mg/kg legems-vekt administrert til mus per os eller intraperitonealt er sikre og effektive. Dette doseringsområde kan varieres avhengig av den grad av aktivering som søkes, og det spesielle legemiddel til påvirkning av sentralnervesystemet som det dreier seg om. The new activating compound of formula I itself shows no visible effect on the central nervous system, and no toxic effects have been observed as a result of its administration. Its valuable physiological effect becomes apparent when it is administered to animals in conjunction with known, centrally acting drugs. Doses of this compound in an order of magnitude of around 40 to approx. 220 mg/kg body weight administered to mice orally or intraperitoneally is safe and effective. This dosage range can be varied depending on the degree of activation that is sought, and the particular drug for affecting the central nervous system that is involved.
I den følgende tabell I er gjengitt data som er representative for den aktivering som fremkalles av den nye forbindelse med formel I, idet man har demonstrert for-lengelsen av hexobarbital-narkosen hos mus. In the following Table I are given data which are representative of the activation induced by the new compound of formula I, having demonstrated the prolongation of hexobarbital anesthesia in mice.
Den forlengelse av hexobarbital-narkosen hos mus som fremstilles med den aktiverende forbindelse når den administreres samtidig med og i forskjellige tidsin-tervaller forut for tilførselen av den sentralt virkende legemiddel er eksempelvis fremstilt i tabell II: Den aktiverende virkning som vår nye forbindelse viser overfor det krampedem-pende middel «Dilantin» i dets kjente be-skyttende rolle mot elektrosjokk hos mus, er fremstilt i den etterfølgende tabell III: Videre demonstrasjoner av de aktiverende virkninger av den nye kjemiske forbindelse med formel I på sentralt virkende midler, administrert ad forskjellig vei, er fremstilt i den følgende tabell IV: The prolongation of the hexobarbital narcosis in mice which is produced with the activating compound when it is administered simultaneously with and at different time intervals prior to the administration of the centrally acting drug is shown, for example, in Table II: The activating effect which our new compound shows against the The anticonvulsant "Dilantin" in its known protective role against electroshock in mice is shown in the following table III: Further demonstrations of the activating effects of the new chemical compound of formula I on centrally acting agents, administered by different routes , is presented in the following table IV:
Administrasjonen av den nye aktiverende forbindelse per se eller sammensatt med sentralt virkende legemidler som den skal aktivere, kan lett utføres ved bruk av passende farmasøytiske tilsetninger og for-tynnere i form av tabletter, kapsler, pul-vere, eliksirer, suspensjoner og injiserbare væsker såsom vann og vandige polyhy-driske alkoholer. Det er ikke nødvendig at den aktiverende forbindelse og det sentralt virkende middel administreres i samme form eller ad samme vei. Man kan for eksempel etter valg tilføre det ene per os og det annet intraperitonealt, eller ett intravenøst og det annet per os. Kort sagt har man adgang til å velge mellom former og veier for administreringen, så man kan tilpasse seg de krav som stilles av en fore-liggende situasjon. The administration of the new activating compound per se or in combination with centrally acting drugs which it is to activate can be easily carried out using suitable pharmaceutical additives and diluents in the form of tablets, capsules, powders, elixirs, suspensions and injectable liquids such as water and aqueous polyhydric alcohols. It is not necessary that the activating compound and the centrally acting agent are administered in the same form or by the same route. One can, for example, choose to administer one per os and the other intraperitoneally, or one intravenously and the other per os. In short, you have access to choose between forms and ways of administration, so you can adapt to the requirements of a given situation.
For at fremstillingen av den nye kjemiske forbindelse skal være fullt tilgjen-gelig for folk innen bransjen, er følgende eksempler gitt som illustrasjon: Eksempel 1. In order for the production of the new chemical compound to be fully accessible to people in the industry, the following examples are given as illustrations: Example 1.
Til 116 g (1 mol) levulinsyre settes langsomt under omrøring og avkjøling 147 g (1 mol) 2-(4-pyridyl)-ethylhydrazin. Re-aksjonsblandingen befries for vann ved oppvarmning på dampbad under redusert trykk. Residuet destilleres under vakuum og gir 200 g (92 pst.) 2-[2-(4-pyridyl)-ethyl]-6-methyl-4,5-dihydro-3-pyridazinon som har et kokepunkt ved 157,5° C ved 0,3 mm trykk. Destillatet kan omkrystalliseres fra isopropylether (15 ml/g) under bruk av trekull (Darco) så at man gjenvinner 86 pst. renset produkt med smeltepunkt 91— 92° C. 147 g (1 mol) of 2-(4-pyridyl)-ethylhydrazine are slowly added to 116 g (1 mol) of levulinic acid while stirring and cooling. The reaction mixture is freed from water by heating in a steam bath under reduced pressure. The residue is distilled under vacuum and yields 200 g (92 percent) of 2-[2-(4-pyridyl)-ethyl]-6-methyl-4,5-dihydro-3-pyridazinone which has a boiling point of 157.5° C at 0.3 mm pressure. The distillate can be recrystallized from isopropyl ether (15 ml/g) using charcoal (Darco) so that 86 per cent of the purified product with a melting point of 91-92° C is recovered.
Eksempel 2. Example 2.
En blanding av 41,1 g (0,3 mol) 2-(4-pyridyl)-ethylhydrazin fremstilt som i eksempel 1, 50 ml vann, 43,2 g (0,3 mol) ethyllevulinat og 25 ml alkohol varmes med tilbakeløpskjøling på dampbad i en time. Alkohol og vann fjernes derpå så full-stendig som mulig under vakuum. Det 68 g gjenværende råprodukt krystalliserer ved avkjøling. Ettter to omkrystalliserin-ger fra ligroin av 60—90° C under bruk av trekull, idet man lar oppløsningen avkjø-les langsomt mens man rører, fåes et ut-bytte på 32 g (49 pst.) 2-[2-4(pyridyl)et-hyl]-6-methyl-4,'5-dihydro-3-p<y>ridazinon. Smeltepunkt 91—93° C. A mixture of 41.1 g (0.3 mol) of 2-(4-pyridyl)-ethylhydrazine prepared as in Example 1, 50 ml of water, 43.2 g (0.3 mol) of ethyl levulinate and 25 ml of alcohol is heated under reflux in a steam bath for an hour. Alcohol and water are then removed as completely as possible under vacuum. The 68 g of remaining crude product crystallizes on cooling. After two recrystallizations from ligroin at 60-90° C using charcoal, allowing the solution to cool slowly while stirring, a yield of 32 g (49 per cent) is obtained 2-[2-4( pyridyl)ethyl]-6-methyl-4,'5-dihydro-3-pyridazinone. Melting point 91-93° C.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR6924241A FR2052105A6 (en) | 1969-07-16 | 1969-07-16 |
Publications (2)
Publication Number | Publication Date |
---|---|
NO131698B true NO131698B (en) | 1975-04-01 |
NO131698C NO131698C (en) | 1975-07-09 |
Family
ID=9037545
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO2725/70A NO131698C (en) | 1969-07-16 | 1970-07-10 |
Country Status (8)
Country | Link |
---|---|
US (1) | US3656867A (en) |
JP (1) | JPS5434164B1 (en) |
CA (1) | CA946903A (en) |
CH (1) | CH528176A (en) |
DE (1) | DE7026816U (en) |
FR (1) | FR2052105A6 (en) |
GB (1) | GB1313374A (en) |
NO (1) | NO131698C (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH604422A5 (en) * | 1973-02-09 | 1978-09-15 | Alsacienne Atom | |
JPS49133802U (en) * | 1973-03-14 | 1974-11-18 | ||
JPS5121211A (en) * | 1974-08-15 | 1976-02-20 | Doryokuro Kakunenryo | DENJIHONPU |
JPS5219307A (en) * | 1975-08-06 | 1977-02-14 | Toshiba Corp | Ring shaped straight line induction type electro magetic pump |
US4255877A (en) * | 1978-09-25 | 1981-03-17 | Brs, Inc. | Athletic shoe having external heel counter |
JP2014096895A (en) * | 2012-11-08 | 2014-05-22 | Toshiba Corp | Electromagnetic pump |
US11049624B2 (en) | 2015-12-07 | 2021-06-29 | Ge-Hitachi Nuclear Energy Americas Llc | Nuclear reactor liquid metal coolant backflow control |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2764095A (en) * | 1954-02-05 | 1956-09-25 | Mine Safety Appliances Co | Polyphase electromagnetic induction pump |
US3005116A (en) * | 1957-06-04 | 1961-10-17 | English Electric Co Ltd | Discontinuous induction type dynamoelectric machines |
-
1969
- 1969-07-16 FR FR6924241A patent/FR2052105A6/fr not_active Expired
-
1970
- 1970-07-10 NO NO2725/70A patent/NO131698C/no unknown
- 1970-07-14 CH CH1062770A patent/CH528176A/en not_active IP Right Cessation
- 1970-07-15 CA CA088,331*7A patent/CA946903A/en not_active Expired
- 1970-07-15 US US54946A patent/US3656867A/en not_active Expired - Lifetime
- 1970-07-16 JP JP6179970A patent/JPS5434164B1/ja active Pending
- 1970-07-16 GB GB3463470A patent/GB1313374A/en not_active Expired
- 1970-07-16 DE DE7026816U patent/DE7026816U/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE2035329A1 (en) | 1971-02-18 |
CA946903A (en) | 1974-05-07 |
JPS5434164B1 (en) | 1979-10-25 |
DE2035329B2 (en) | 1976-05-13 |
CH528176A (en) | 1972-09-15 |
NO131698C (en) | 1975-07-09 |
FR2052105A6 (en) | 1971-04-09 |
US3656867A (en) | 1972-04-18 |
DE7026816U (en) | 1977-11-17 |
GB1313374A (en) | 1973-04-11 |
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