PL92131B1 - - Google Patents
Download PDFInfo
- Publication number
- PL92131B1 PL92131B1 PL1975178230A PL17823075A PL92131B1 PL 92131 B1 PL92131 B1 PL 92131B1 PL 1975178230 A PL1975178230 A PL 1975178230A PL 17823075 A PL17823075 A PL 17823075A PL 92131 B1 PL92131 B1 PL 92131B1
- Authority
- PL
- Poland
- Prior art keywords
- piperazine
- naphthyloxy
- mole
- methoxyphenyl
- formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych pochodnych l-[3-/l-naftyloksy/-2-hy- droksypropylo]-piperazyny o wzorze 1, ich farma- kalogicznie dopuszczalnych soli. Nowe zwiazki znajduja zastosowanie w wytwarzaniu srodków leczniczych o dzialaniu obnizajacym cisnienie krwi.Nowe zwiazki wybitnie obnizaja cisnienie krwi, przez co posiadaja wlasnosci antyhypertoniczne.Oprócz tego hamuja one reakcje anafilaksji u szczurów wywolane podaniem dekstranu.W publikacji w J. Org. Chem. 23 (1958) str. 1915 opisano niektóre pochodne l-[3-/l-naftyloksy/-2- -hydroksypropylo]-piperazyny, ale nie podano ich farmakologicznego dzialania. Jak wykazaly dos¬ wiadczenia, nowe zwiazki posiadaja niespodziewa¬ nie znacznie lepsze dzialanie antyhypertoniczne niz opisane uprzednio substancje.Wedlug wynalazku sposób wytwarzania zwiaz¬ ków o wzorze 1 polega na tym, ze zwiazek o ogól¬ nym wzorze 2, w którym R: oznacza atom wodoru, a R2 oznacza atom chlorowca, przy czym reszty Rx i R2 razem moga oznaczac kreske obrazujaca wartosciowosc, poddaje sie reakcji z metoksy- fenylopiperazyna o wzorze 3, albo 1-naftol poddaje sie reakcji ze zwiazkiem o pgólnym wzorze 4 w którym RL i R2 posiadaja wyzej podane znaczenie, a otrzymane zwiazki o wzorze 1 ewentualnie przeprowadza sde w ich farmakologicznie dopusz¬ czalne sole. 2 Jako atom chlorowca reszty Ra korzystnie wy¬ stepuje atom chloru. Reakcje prowadzi sie przez zmieszanie molowych ilosci komponentów reakcji i pozostawienie w temperaturze pokojowej. Reak¬ cje mozna przyspieszyc przez krótkie ogrzewanie ewentualnie w naczyniu cisnieniowym. Mozna tak¬ ze w razie potrzeby dodawac rozpuszczalniki takie jak nizsze alkohole.W celu wytworzenia soli traktuje sie zwiazki otrzymane sposobem wedlug wynalazku farma¬ kologicznie dopuszczalnymi kwasami organicznymi lub nieorganicznymi zwlaszcza kwasem solnym, siarkowym, fosforowym, mlekowym, cytrynowym albo alkilosulfonowym.W celu wytworzenia srodków leczniczych sub¬ stancje o wzorze 1 miesza sie w znany sposób z odpowiednim farmaceutycznym nosnikiem, sub¬ stancje zapachowa, smakowa i barwnikiem i na przyklad tabletkuje albo drazuje albo po dodaniu odpowiednich substancji pomocniczych, zawiesza albo rozpuszcza w wodzie lub oleju, zwykle w oleju z oliwek.Przyklad I. l-/2-metoksyfenylo/-4-[3-/l-nafty- loksy/j2-hydroksypropylo]Hpiperazyna.Mieszanine skladajaca sie z 30,0 g (0,15 mola) 2,3-epoksy-l-/l-naftyloksy/-propanu i 28,8 g (0,15 mola) l-/2-metoksyfenylo/-piperazyny, ogrzewa sie do 120°C i pozostawia w tej temperaturze przez godzin. Po ochlodzeniu otrzymuje sie czerwony i skrzeply produkt, który po przekrystalizowaniu 92 13192 3 z izopropariolu topnieje w temperaturze 125—126°C. " Wydajnosc: 46,5 g (79% wydajnosci teoretycznej), temperatura topnienia dwuchlorowodorku: 212— 213°C (metanol/etanol 1:2).Przyklad II. l-/4-metoksyfenylo/-4-[3-/l-naf- tyloksy/-2-hydroksypropylo]-piperazyna.Miesza sie 20,0 g (0,1 mola) 2,3-epoksy-l-/l-naf- tyloksy/-propanu z 30 ml etanolu i 19,2 g (0,1 mola) l-/4-metoksyfenylo/-piperazyine utrzymuje przez 6 godzin temperature 60°C, pozostawia przez noc i nastepnie odparowuje etanol. Oleista pozostalosc rozpuszcza sie w chloroformie, wysyca gazowym chlorowodorem a potem dodaje eter, przy czym wypada dwuchlorowodorek. Odsaczac sie go i przekrystalizowuje z mieszaniny metanol/etanol (1:3). Temperatura topnienia: 237—238°C. Wy¬ dajnosc: 76% wydajnosci teoretycznej.Przyklad III. l-/4-metoksyfenylo/-4-[3-/l- -naftyloksy/-2-hydroksypropylo]-piperazyna.Mieszanine skladajaca sie z 27,8 g (0,3 mola) eprichlorohydryny, 45 g (0,3 mola) suchego jodku sodowego i 100 ml bezwodnego acetonu pozostawia przez 24 godziny w ciemnosci, saczy, a przesacz miesza z 28,8 g (0,15 mola) l-/4-metoksyfenylo/- -piperazyna. Po 24 godzinach wrzenia zateza sie w temperaturze lazni 35°C przy 12 ton, przy czym zostaje ciemnobrazowy olej. Do tego oleju dodaje sie 14,4 g (0,1 mola) dojbrze sproszkowanego a-naftolu, ogrzewa do temperatury 70°C i wtedy powoli wkrapla sie (roztwór 4,0 g (0,1 mola) wodoro¬ tlenku sodowego w 25 ml wody. Temperature utrzymuje sie przez lekkie ochlodzenie, w gra¬ nicach 72—75°C. Potem utrzymuje sie przez dalsze 4 godziny temperature 75°C. Po schlodzeniu otrzymuje sie brazowa ciagnaca mase, która roz- 131 4 ciera sie kilkakrotnie z woda. Nastepnie rozpusz¬ cza w chloroformie, saczy i przemywa warstwe/ chloroformowa kolejno 2n-NaOH, woda i ln-HCl f woda. Po wysuszeniu siarczanem sodowym do¬ prowadza sie chlorowodór i dodaje eter. Zanie¬ czyszczony nieco dwuchlorowodorek odsacza sie- pod zmniejszonym cisnieniem i przekrystalizowuje kilkakrotnie z metanolu z dodatkiem wegla aktywnego. Temperatura topnienia: 235—237°C. 1C Wydajnosc: 13,4 g co stanowi 29% wydajnosci teoretycznej. ^ ;*; PL PL PL PL PL PL PL PL PL PL
Claims (1)
1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2408804A DE2408804C2 (de) | 1974-02-23 | 1974-02-23 | 1-(2-Methoxyphenyl)-4-[3-(naphth-1-yl-oxy)-2-hydroxy-propyl]-piperazin, dessen Salze, Verfahren zu ihrer Herstellung sowie Arzneimittel, die diese Verbindungen enthalten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL92131B1 true PL92131B1 (pl) | 1977-03-31 |
Family
ID=5908286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975178230A PL92131B1 (pl) | 1974-02-23 | 1975-02-21 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3997666A (pl) |
| JP (1) | JPS6029712B2 (pl) |
| AR (1) | AR206339A1 (pl) |
| AT (1) | AT340937B (pl) |
| BE (1) | BE825755A (pl) |
| CA (1) | CA1039282A (pl) |
| CH (2) | CH612958A5 (pl) |
| DE (1) | DE2408804C2 (pl) |
| DK (1) | DK135124C (pl) |
| ES (1) | ES434829A1 (pl) |
| FI (1) | FI59248C (pl) |
| FR (1) | FR2261770B1 (pl) |
| GB (1) | GB1445548A (pl) |
| IE (1) | IE40678B1 (pl) |
| NL (2) | NL175059B (pl) |
| PL (1) | PL92131B1 (pl) |
| SE (1) | SE405601B (pl) |
| SU (2) | SU549085A3 (pl) |
| YU (2) | YU37156B (pl) |
| ZA (1) | ZA751031B (pl) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2387971A1 (fr) * | 1977-04-19 | 1978-11-17 | Delalande Sa | Nouvelles trimethoxy cinnamoyles piperazines, leur procede de preparation et leur application en therapeutique |
| US4882330A (en) * | 1986-11-21 | 1989-11-21 | A. H. Robins Company, Incorporated | 1-aryloxy-4-[((4-aryl)-1-piperazinyl]-2-butanols useful as antiallergy agents |
| EP0269383A3 (en) * | 1986-11-21 | 1990-05-02 | A.H. Robins Company, Incorporated | 1-Aryloxy-4-[(4-aryl)-1-piperazinyl]-2-butanols useful as antiallergy agents |
| DE3918543A1 (de) * | 1989-06-07 | 1990-12-13 | Boehringer Mannheim Gmbh | Verwendung von naftopidil zur therapie der dysurie bei benigner prostata-hypertrophie |
| DE3918542A1 (de) * | 1989-06-07 | 1990-12-13 | Boehringer Mannheim Gmbh | Hydroxylierte 1-phenyl-4-(3-(napthth-1-yl-oxy)-2-hydroxy -propyl)-piperazine, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
| US5932538A (en) * | 1996-02-02 | 1999-08-03 | Nitromed, Inc. | Nitrosated and nitrosylated α-adrenergic receptor antagonist compounds, compositions and their uses |
| US20050065161A1 (en) * | 1996-02-02 | 2005-03-24 | Nitromed, Inc. | Nitrosated and nitrosylated alpha-adrenergic receptor antagonist compounds, compositions and their uses |
| US20020143007A1 (en) * | 1996-02-02 | 2002-10-03 | Garvey David S. | Nitrosated and nitrosylated alpha-adrenergic receptor antagonists, compositions and methods of use |
| KR20000070507A (ko) | 1997-01-30 | 2000-11-25 | 요시다 쇼지 | 하이드로퀴논 유도체 |
| CN1768745A (zh) | 1998-09-30 | 2006-05-10 | 武田药品工业株式会社 | 改善膀胱排泄能力的药物 |
| US20020065286A1 (en) * | 2000-08-21 | 2002-05-30 | Davies Michael John | Treatment of wounds |
| US20020091129A1 (en) * | 2000-11-20 | 2002-07-11 | Mitradev Boolell | Treatment of premature ejaculation |
| US20030229001A1 (en) * | 2002-01-31 | 2003-12-11 | Pfizer Inc. | Treatment of male sexual dysfunction |
| BR0313593A (pt) | 2002-08-19 | 2005-07-12 | Pfizer Prod Inc | Terapia de combinação para doenças hiperproliferativas |
| GB0219961D0 (en) | 2002-08-28 | 2002-10-02 | Pfizer Ltd | Oxytocin inhibitors |
| US7323462B2 (en) * | 2002-12-10 | 2008-01-29 | Pfizer Inc. | Morpholine dopamine agonists |
| EP1572173B1 (en) | 2002-12-13 | 2010-04-28 | Warner-Lambert Company LLC | Alpha-2-delta ligand to treat lower urinary tract symptoms |
| CA2451267A1 (en) * | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
| PA8597401A1 (es) * | 2003-03-14 | 2005-05-24 | Pfizer | Derivados del acido 3-(1-[3-(1,3-benzotiazol-6-il) propilcarbamoil] cicloalquil) propanoico como inhibidores de nep |
| US20040220186A1 (en) * | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
| OA13174A (en) | 2003-05-30 | 2006-12-13 | Ranbaxy Lab Ltd | Substituted pyrrole derivatives and their use as HMG-Co inhibitors. |
| US20050065158A1 (en) * | 2003-07-16 | 2005-03-24 | Pfizer Inc. | Treatment of sexual dysfunction |
| US7291640B2 (en) * | 2003-09-22 | 2007-11-06 | Pfizer Inc. | Substituted triazole derivatives as oxytocin antagonists |
| WO2006100557A1 (en) | 2005-03-21 | 2006-09-28 | Pfizer Limited | Substituted triazole derivatives as oxytocin antagonists |
| WO2007017752A1 (en) * | 2005-08-10 | 2007-02-15 | Pfizer Limited | Substituted triazole derivatives as oxytocin antagonists |
| GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| WO2007054896A1 (en) | 2005-11-08 | 2007-05-18 | Ranbaxy Laboratories Limited | Process for (3r, 5r)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4- [(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3, 5-dihydroxy-heptanoic acid hemi calcium salt |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| US8383660B2 (en) | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| US7919506B2 (en) | 2006-03-10 | 2011-04-05 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| EP2077262A4 (en) * | 2006-10-23 | 2011-12-28 | Takeda Pharmaceutical | IMINOPYRIDINE DERIVATIVE AND USE THEREOF |
| CN101663262B (zh) | 2006-12-01 | 2014-03-26 | 百时美施贵宝公司 | 用于治疗动脉粥样硬化和心血管疾病的作为cetp抑制剂的n-(3-苄基)-2,2-(二苯基)-丙-1胺衍生物 |
| US8481569B2 (en) * | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
| US20110039892A1 (en) | 2008-04-23 | 2011-02-17 | Takeda Pharmaceutical Company Limited | Iminopyridine derivative and use thereof |
| CN101671317B (zh) * | 2009-10-09 | 2011-04-27 | 蚌埠丰原涂山制药有限公司 | 一种萘哌地尔的制备方法 |
| CN101747293B (zh) * | 2009-12-29 | 2011-12-07 | 蚌埠丰原涂山制药有限公司 | 萘哌地尔的制备方法 |
| JP5807423B2 (ja) * | 2011-07-21 | 2015-11-10 | 大日本印刷株式会社 | ナフトピジルの製造方法 |
| CN102816136A (zh) * | 2012-09-18 | 2012-12-12 | 通化吉通药业有限公司 | 萘哌地尔制备方法 |
| JP2016516804A (ja) | 2013-04-17 | 2016-06-09 | ファイザー・インク | 心血管疾患を治療するためのｎ−ピペリジン−３−イルベンズアミド誘導体 |
| US9272980B2 (en) | 2014-06-06 | 2016-03-01 | Ktn Biotec, Inc. | Anticancer agent |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| AU2020209215B2 (en) | 2019-01-18 | 2023-02-02 | Astrazeneca Ab | PCSK9 inhibitors and methods of use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA967965A (en) * | 1968-12-24 | 1975-05-20 | Hoffmann-La Roche Limited | Aromatic ethers and process for the manufacture thereof |
| GB1317479A (en) * | 1970-11-10 | 1973-05-16 | Pfizer Ltd | 1-2-hydroxy-3-phenoxy or phenylthiopropyl-4-phenyl-piperazine derivatives |
| DE2235597A1 (de) * | 1972-07-20 | 1974-01-31 | Boehringer Mannheim Gmbh | 1-eckige klammer auf 3-(5,6,7,8tetrahydronaphth-1-yl-oxy) -propyl eckige klammer zu -piperazin-derivate und verfahren zu ihrer herstellung |
-
0
- NL NLAANVRAGE7501877,A patent/NL175059C/xx active
-
1974
- 1974-02-23 DE DE2408804A patent/DE2408804C2/de not_active Expired
-
1975
- 1975-01-01 AR AR257639A patent/AR206339A1/es active
- 1975-01-28 US US05/544,719 patent/US3997666A/en not_active Expired - Lifetime
- 1975-02-12 CA CA219,883A patent/CA1039282A/en not_active Expired
- 1975-02-17 GB GB656975A patent/GB1445548A/en not_active Expired
- 1975-02-18 ES ES434829A patent/ES434829A1/es not_active Expired
- 1975-02-18 FI FI750449A patent/FI59248C/fi not_active IP Right Cessation
- 1975-02-18 YU YU0382/75A patent/YU37156B/xx unknown
- 1975-02-18 NL NLAANVRAGE7501877,A patent/NL175059B/xx not_active IP Right Cessation
- 1975-02-18 DK DK58175A patent/DK135124C/da not_active IP Right Cessation
- 1975-02-19 ZA ZA00751031A patent/ZA751031B/xx unknown
- 1975-02-20 SE SE7501911A patent/SE405601B/xx not_active IP Right Cessation
- 1975-02-20 BE BE153540A patent/BE825755A/xx not_active IP Right Cessation
- 1975-02-20 JP JP50021386A patent/JPS6029712B2/ja not_active Expired
- 1975-02-21 SU SU2112509A patent/SU549085A3/ru active
- 1975-02-21 PL PL1975178230A patent/PL92131B1/pl unknown
- 1975-02-21 IE IE359/75A patent/IE40678B1/xx unknown
- 1975-02-21 CH CH1023478A patent/CH612958A5/xx not_active IP Right Cessation
- 1975-02-21 AT AT132375A patent/AT340937B/de not_active IP Right Cessation
- 1975-02-21 FR FR7505511A patent/FR2261770B1/fr not_active Expired
- 1975-02-21 CH CH218575A patent/CH609342A5/xx not_active IP Right Cessation
-
1976
- 1976-01-07 SU SU2308659A patent/SU561514A3/ru active
-
1981
- 1981-04-21 YU YU1044/81A patent/YU37157B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL92131B1 (pl) | ||
| EP0159566B1 (en) | Novel piperazine derivatives, processes for production thereof, and pharmaceutical compositions comprising said compounds as active ingredient | |
| CA1238636A (en) | Piperazine derivatives and their acid addition salts | |
| CA1168232A (en) | Isoquinoline derivatives, a process for their preparation, pharmaceutical formulations containing them and their use | |
| PL117515B1 (en) | Process for preparing novel,substituted aminothiazoles | |
| DE2847693A1 (de) | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen | |
| Klayman et al. | 2-Acetylpyridine thiosemicarbazones. 8. Derivatives of 1-acetylisoquinoline as potential antimalarial agents | |
| EP0612738A1 (en) | Diphenylpiperazine derivative and drug for circulatory organ containing the same | |
| EP0120558B1 (en) | Antihypertensive n-piperazinylalkanoylanilides | |
| NZ229144A (en) | Substituted pyrimidinedione derivatives and pharmaceutical compositions, and 1-(1-piperazinyl) isoquinoline as an intermediate reagent | |
| US3947446A (en) | Novel 1-[3-(5,6,7,8-tetrahydronaphth-1-yloxy)-propyl]-piperazine compounds and therapeutic compositions | |
| PL125663B1 (en) | Process for preparing novel derivatives of n-(trimethoxybenzyl)-piperazine | |
| CA1084918A (en) | New, in 11-position substituted 5,11-dihydro-6h- pyrido 2,3-b - 1,4 benzodiazepine-6-ones, processes for their preparation and pharmaceutical compositions containing such compounds | |
| JPS6350353B2 (pl) | ||
| PL102327B1 (pl) | A method of producing new 2-anilinoxazolines | |
| US3932411A (en) | 3,4-Dihydro-2H-naphthalene-1-one-5-oxypropyl-piperazine compounds | |
| NZ234789A (en) | Piperazinyl substituted pyridine and oxazolo(4,5-b)pyridine derivatives and pharmaceutical compositions thereof | |
| EP0056866A2 (de) | Phenylpiperazinderivate von Hetarylphenolen und Hetarylanilinen, ihre Herstellung und diese enthaltende therapeutische Mittel | |
| US3657276A (en) | Dibenzo (c f) thiazepine (1 2) compounds | |
| DE2514334A1 (de) | Neue pyridinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazeutischen zusammensetzungen | |
| FI61484B (fi) | Foerfarande foer framstaellning av z-3-(4-bromfenyl)-n-metyl-3-(3-pyridyl)-allylamin med antidepressiv och aongestdaempande verkan | |
| US3951961A (en) | Xanthene and thioxanthene derivatives, compositions thereof and a method of preparation thereof | |
| DE2114884A1 (de) | Basisch substituierte Derivate des 1(2H)-Phthalazinons | |
| US2695293A (en) | N, n'-substituted diamine compounds and method of making the same | |
| CA1041098A (en) | 1-(3-(naphthyl-1-yl-oxy)-propyl)-piperazine derivatives |