UY26111A1 - DERIVATIVES OF CICLOBUTEN-3, 4-DIONA, ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS - Google Patents

DERIVATIVES OF CICLOBUTEN-3, 4-DIONA, ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS

Info

Publication number
UY26111A1
UY26111A1 UY26111A UY26111A UY26111A1 UY 26111 A1 UY26111 A1 UY 26111A1 UY 26111 A UY26111 A UY 26111A UY 26111 A UY26111 A UY 26111A UY 26111 A1 UY26111 A1 UY 26111A1
Authority
UY
Uruguay
Prior art keywords
indole
methyl
group
dioxocyclobut
dihydro
Prior art date
Application number
UY26111A
Other languages
Spanish (es)
Inventor
Philippo Christophe
Philippe R Bovy
Original Assignee
Sanofi Synthelabo
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 Sanofi Synthelabo filed Critical Sanofi Synthelabo
Publication of UY26111A1 publication Critical patent/UY26111A1/en

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Classifications

    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Urology & Nephrology (AREA)
  • Endocrinology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Reproductive Health (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Compuestos de fórmula general (I) (representada en la figura 1), así como procedimientos de preparación de los mismos, caracterizados porque: R1 y R2 representan, independientemente entre sí, un átomo de hidrógeno o un grupo alquilo de 1 a 6 átomos de carbono, un grupo C2-6 alquenilo, un grupo -(CH2)n-C3-6 cicloalquilo ; R3 representa un átomo de hidrógeno o un grupo alquilo de 1 a 6 átomos de carbono; W representa un grupo NR4R5, en el cual; R4 representa un grupo fenilo cuando R5 representa un átomo de hidrógeno, un grupo C1-6 alquilo o un grupo C2-6 alquenilo, R4 y R5 forman junto con el nitrógeno que lo s lleva un indol, una indolina o una quinoleína, y n representa 0, 1 o 2. Ejemplos de compuestos de fórmula general (I): -4-[[[2-(2,3-dihidro-1-H-indol-1-il)-3,4- dioxociclobut-1-en-1-il]amino]metil]ciclohexan-1-N-etil-carboxamida; -4-[[[2-(2,3-dihidro-1-H-indol-1-il)-3,4- dioxociclobut-1-en-1-il]amino]metil]ciclohexan-1-N-metil-carboxamida; -4-[[[2-(2,3-dihidro-1-H-indol-1-il)-3,4- dioxociclobut-1-en-1-il]amino]metil]ciclohexan-1-N-isopropil-carboxamida; entre otros. Los compuestos de fórmula (I) son de utilidad para la preparación de un medicamento destinado a tratar una patología donde la inhibición de la fosfodiesterasa 5 aporta un beneficio terapéutico, y más particularmente donde la patología consiste en: hipertrofia benigna de próstata, incontinencia, vesícula obstruida, dismenorrea, parto precoz o prematuro, disfunciones eréctiles, disfunciones sexuales en el hombre, disfunciones sexuales en la mujer, angina de pecho, hipertensión pulmonar, ataque de apoplejía, arteriosclerosis, insuficiencia ventricular, desórdenes vasculares periféricos, asma, bronquitis, rinitis alérgica, glaucoma o desórdenes de la mortalidad intestinal.Compounds of general formula (I) (represented in figure 1), as well as preparation processes thereof, characterized in that: R1 and R2 represent, independently of each other, a hydrogen atom or an alkyl group of 1 to 6 atoms of carbon, a C2-6 alkenyl group, a - (CH2) n-C3-6 cycloalkyl group; R3 represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms; W represents an NR4R5 group, in which; R4 represents a phenyl group when R5 represents a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group, R4 and R5 together with the nitrogen carried by an indole, indole or quinoline, and n represents 0, 1 or 2. Examples of compounds of general formula (I): -4 - [[[2- (2,3-dihydro-1-H-indole-1-yl) -3,4-dioxocyclobut-1- en-1-yl] amino] methyl] cyclohexan-1-N-ethyl-carboxamide; -4 - [[[2- (2,3-dihydro-1-H-indole-1-yl) -3,4- dioxocyclobut-1-en-1-yl] amino] methyl] cyclohexane-1-N- methyl carboxamide; -4 - [[[2- (2,3-dihydro-1-H-indole-1-yl) -3,4- dioxocyclobut-1-en-1-yl] amino] methyl] cyclohexane-1-N- isopropyl-carboxamide; among others. The compounds of formula (I) are useful for the preparation of a medicine intended to treat a pathology where the inhibition of phosphodiesterase 5 provides a therapeutic benefit, and more particularly where the pathology consists of: benign hypertrophy of the prostate, incontinence, gallbladder obstructed, dysmenorrhoea, early or premature labor, erectile dysfunction, sexual dysfunction in men, sexual dysfunction in woman, angina, pulmonary hypertension, stroke, arteriosclerosis, ventricular failure, peripheral vascular disorders, asthma, bronchitis, allergic rhinitis , glaucoma or disorders of intestinal mortality.

UY26111A 1999-04-20 2000-04-19 DERIVATIVES OF CICLOBUTEN-3, 4-DIONA, ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS UY26111A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9904944A FR2792635B1 (en) 1999-04-20 1999-04-20 CYCLOBUTENE-3,4-DIONE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION

Publications (1)

Publication Number Publication Date
UY26111A1 true UY26111A1 (en) 2000-12-29

Family

ID=9544619

Family Applications (1)

Application Number Title Priority Date Filing Date
UY26111A UY26111A1 (en) 1999-04-20 2000-04-19 DERIVATIVES OF CICLOBUTEN-3, 4-DIONA, ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS

Country Status (6)

Country Link
AR (1) AR023528A1 (en)
AU (1) AU3971700A (en)
CO (1) CO5170443A1 (en)
FR (1) FR2792635B1 (en)
UY (1) UY26111A1 (en)
WO (1) WO2000063170A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6403597B1 (en) 1997-10-28 2002-06-11 Vivus, Inc. Administration of phosphodiesterase inhibitors for the treatment of premature ejaculation
US6548490B1 (en) * 1997-10-28 2003-04-15 Vivus, Inc. Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction
DE10058663A1 (en) * 2000-11-25 2002-05-29 Merck Patent Gmbh Use of thienopyrimidines
US20040106794A1 (en) * 2001-04-16 2004-06-03 Schering Corporation 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
AR068509A1 (en) * 2007-09-19 2009-11-18 Jerini Ag BRADIQUININE B1 RECEIVER ANTAGOSNIST

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9312210D0 (en) * 1993-06-14 1993-07-28 Smithkline Beecham Plc Chemical compounds
BR9612434A (en) * 1995-12-28 1999-12-28 Fujiwasa Pharmaceutical Co Ltd Benzimidazole derivatives

Also Published As

Publication number Publication date
WO2000063170A1 (en) 2000-10-26
FR2792635A1 (en) 2000-10-27
AR023528A1 (en) 2002-09-04
AU3971700A (en) 2000-11-02
CO5170443A1 (en) 2002-06-27
FR2792635B1 (en) 2001-06-01

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Legal Events

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Effective date: 20100426