CA2181581A1 - Derives de benzylamine contenant des groupes nitroxy et leur utilisation pour traiter les maladies cardio-vasculaires et l'hypertension intra-oculaire - Google Patents

Derives de benzylamine contenant des groupes nitroxy et leur utilisation pour traiter les maladies cardio-vasculaires et l'hypertension intra-oculaire

Info

Publication number
CA2181581A1
CA2181581A1 CA002181581A CA2181581A CA2181581A1 CA 2181581 A1 CA2181581 A1 CA 2181581A1 CA 002181581 A CA002181581 A CA 002181581A CA 2181581 A CA2181581 A CA 2181581A CA 2181581 A1 CA2181581 A1 CA 2181581A1
Authority
CA
Canada
Prior art keywords
substituted
alkyl
phenyl
radical
benzyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002181581A
Other languages
English (en)
Inventor
Jan Bron
Geert Jan Sterk
Hendrik Timmerman
Meta E. J. Veerman
Jan Fetze Van Der Werf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Altana Pharma BV
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2181581A1 publication Critical patent/CA2181581A1/fr
Abandoned legal-status Critical Current

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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
    • 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
    • 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
    • C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
    • C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Vascular Medicine (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Des composés ont la formule (I), dans laquelle R1 désigne alcylène C¿1-15?, cycloalkylène C¿5-7? ou di-1-4C-alcylène-5-7C-cycloalcane; R1 désigne hydrogène, alcoyle C¿1-7? ou cycloalcoyle C¿3-8? et R2 désigne hydrogène, alcoyle C¿1-7?, cycloalcoyle C¿3-8? ou A2-Y. Ensemble, R1 et R2, avec l'atome d'azote auquel ils sont tous les deux liés, désignent un hétérocycle pentagonal, hexagonal ou heptagonal substitué ou non sélectionné dans le groupe constitué par la pyrrolidine, la pipéridine, la pipérazine, la morpholine et l'homopipérazine. A2 désigne alcylène C¿1-15?, cycloalcylène C¿5-7? ou di-1-4C-alcylène-5-7C-cycloalcane; Y désigne R3, NH¿2?, NH-R4 ou S-R5. Un résidu pyrrolidine substitué est substitué par un ou deux substituants identiques ou différents sélectionnés dans le groupe constitué par alcoyle C¿1-4?, alcoxy C¿1-4? et hydroxyle. Un résidu pipéridine substitué est substitué par un ou deux substituants identiques ou différents sélectionnés dans le groupe constitué d'alcoyle C¿1-4?, alcoxy C¿1-4? et hydroxyle. Un résidu pipérazine substitué peut être substitué en 2e, 3e, 5e ou 6e position par un résidu alcoyle C¿1-4? et est substitué en 4e position par un substituant sélectionné dans le groupe constitué d'alcoyle C¿1-4?, alcoxycarbonyle C¿1-4?, alcoylcarbonyle C¿1-4?, phényle substitué par R6, R7 et R8, phényl-1-4C-alcoyle substitué dans le résidu phényle par R7 et R8, benzoyle, picolinoyle, nicotinoyle, isonicotinoyle substitués dans le résidu phényle par R6, R7 et R8, benzhydryle substitué le cas échéant par halogène ou alcoyle C¿1-4? et le résidu R4. Un résidu morpholine substitué est substitué par un ou deux résidus alcoyle C¿1-4? identiques ou différents. Un résidu homopipérazine substitué est substitué en 4e position par un substituant sélectionné dans le groupe constitué d'alcoyle C¿1-4?, alcoxycarbonyle C¿1-4?, alcoylcarbonyle C¿1-4?, phényle substitué par R6, R7 et R8, phényl-1-4C-alcoyle substitué dans le résidu phényle par R6, R7 et R8 et benzoyle substitué dans le résidu phényle par R6, R7 et R8. Ces composés sont utiles pour traiter les maladies cardio-vasculaires ainsi que l'hypertension intra-oculaire.
CA002181581A 1994-01-19 1995-01-18 Derives de benzylamine contenant des groupes nitroxy et leur utilisation pour traiter les maladies cardio-vasculaires et l'hypertension intra-oculaire Abandoned CA2181581A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH15794 1994-01-19
CH157/94-2 1994-01-19

Publications (1)

Publication Number Publication Date
CA2181581A1 true CA2181581A1 (fr) 1995-07-20

Family

ID=4180558

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002181581A Abandoned CA2181581A1 (fr) 1994-01-19 1995-01-18 Derives de benzylamine contenant des groupes nitroxy et leur utilisation pour traiter les maladies cardio-vasculaires et l'hypertension intra-oculaire

Country Status (8)

Country Link
EP (1) EP0740649A1 (fr)
JP (1) JPH09507672A (fr)
KR (1) KR970700646A (fr)
CN (1) CN1143950A (fr)
AU (1) AU679834B2 (fr)
BR (1) BR9506549A (fr)
CA (1) CA2181581A1 (fr)
WO (1) WO1995019952A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8067464B2 (en) 2004-10-04 2011-11-29 Nitromed, Inc. Compositions and methods using apocynin compounds and nitric oxide donors
CN101889017B (zh) 2007-10-05 2013-11-27 奥克塞拉有限公司 用于治疗疾病的烷氧基化合物
GB2455176A (en) 2007-11-01 2009-06-03 Acucela Inc Amine derivatives useful for treating ophthalmic diseases and disorders
EP2448569B1 (fr) 2009-07-02 2021-10-27 Acucela, Inc. Pharmacologie de modulateurs du cycle visuel
AU2010328230B2 (en) * 2009-12-07 2016-06-02 Cardioxyl Pharmaceuticals, Inc. Bis-acylated hydroxylamine derivatives
EP2804605A4 (fr) 2012-01-20 2015-07-08 Acucela Inc Composés hétérocycliques substitués pour le traitement d'une maladie
US9446015B2 (en) * 2012-10-23 2016-09-20 Nicox Science Ireland Quinone based nitric oxide donating compounds for ophthalmic use
HUE046722T2 (hu) * 2013-01-18 2020-03-30 Cardioxyl Pharmaceuticals Inc Javított terápiás indexû nitroxil donorok

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56113748A (en) * 1980-02-13 1981-09-07 Kowa Co Aminoethanol derivative and its preparation
NL8802276A (nl) * 1988-09-15 1990-04-02 Cedona Pharm Bv Geneesmiddel met relaxerende werking, dat als aktieve stof een nitraatester bevat.
NL9001955A (nl) * 1990-09-05 1992-04-01 Cedona Pharm Bv Nieuwe thiazolidinederivaten.

Also Published As

Publication number Publication date
AU679834B2 (en) 1997-07-10
JPH09507672A (ja) 1997-08-05
EP0740649A1 (fr) 1996-11-06
CN1143950A (zh) 1997-02-26
BR9506549A (pt) 1997-10-14
KR970700646A (ko) 1997-02-12
AU1535095A (en) 1995-08-08
MX9602847A (es) 1997-12-31
WO1995019952A1 (fr) 1995-07-27

Similar Documents

Publication Publication Date Title
US3900481A (en) Derivatives of pyrrolidine and piperidine
US5859246A (en) 1-phenyl-4-benzylpiperazines: dopamine receptor subtype specific ligands
ZA200006136B (en) Nitrate salts of antihypersensive medicines.
WO2001089528A1 (fr) Derives thio-uree de dihydropyridines possedant une activite d'antagonistes de npy
TW442456B (en) Diaryl antimicrobial agents
HU191643B (en) Process for preparing new n-phenyl-n'-cycloalkyl-alkanoyl-piperazine derivatives
GB2158065A (en) Dihydropyridines
CA2181581A1 (fr) Derives de benzylamine contenant des groupes nitroxy et leur utilisation pour traiter les maladies cardio-vasculaires et l'hypertension intra-oculaire
US5852019A (en) Pyrimidinylpyrazole derivatives
IE912492A1 (en) 1,4-disubstituted piperazines
HU185975B (en) Process forproducing new, benzoaxazolinone derivatives substituted with an aminoalkohol- or aminoketone chain at the 6 position and pharmaceutically acceptable salts thereof
CS229924B2 (en) Production method of new phenylalkylamine
AU731638B2 (en) Novel terephthalamide derivatives
US5095022A (en) Piperidine derivatives and pharmaceutical compositions comprising the same
IE911774A1 (en) Pyridinylpiperazine derivatives
US9273027B2 (en) Arylpiperazine opioid receptor antagonists
US4556656A (en) 2-Benzoxepins
IE45051B1 (en) 2-substituted-4-amino-6,7-dimethoxy-quinazolines
EP0799210A1 (fr) Derives de la piperazine-2,5-dione employes comme modulateurs de la resistance multiple aux anticancereux
JP3041834B2 (ja) Ｎ―アミノアルキル―２―アントラキノンカルボキサミド；ドーパミンレセプターサブタイプに特異的な新しい配位子
JPS6069089A (ja) ジヒドロピリジン−５−ホスホネ−ト誘導体およびその製造法
US4029790A (en) 1-Benzoyl-2 or 4 [2-(4-phenyl-piperazino)-ethyl]-piperidines
US4220603A (en) Pharmaceutically active (omega-aminoalkoxy)bibenzyls
EP0266549B1 (fr) Cinnamylamines, leur procédé de préparation et compositions pharmaceutiques les contenant
KR100373957B1 (ko) 신규한아민유도체,그의제조방법및항부정맥제로서의용도

Legal Events

Date Code Title Description
FZDE Dead