ES2329181T3 - Compuestos intermedios para la produccion de dioxano-2-alquil-carbamatos. - Google Patents

Compuestos intermedios para la produccion de dioxano-2-alquil-carbamatos. Download PDF

Info

Publication number
ES2329181T3
ES2329181T3 ES07013954T ES07013954T ES2329181T3 ES 2329181 T3 ES2329181 T3 ES 2329181T3 ES 07013954 T ES07013954 T ES 07013954T ES 07013954 T ES07013954 T ES 07013954T ES 2329181 T3 ES2329181 T3 ES 2329181T3
Authority
ES
Spain
Prior art keywords
group
general formula
compounds
mmol
methyl
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.)
Expired - Lifetime
Application number
ES07013954T
Other languages
English (en)
Inventor
Ahmed Abouabdellah
Michele Bas
Gihad Dargazanli
Christian Hoornaert
Adrien Tak Li
Florence Medaisko
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.)
Sanofi Aventis France
Original Assignee
Sanofi Aventis France
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 Aventis France filed Critical Sanofi Aventis France
Application granted granted Critical
Publication of ES2329181T3 publication Critical patent/ES2329181T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A61P1/12—Antidiarrhoeals
    • 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
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • 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
    • A61P11/06—Antiasthmatics
    • 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
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • 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
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • 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
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • 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
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Immunology (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Urology & Nephrology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychiatry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Otolaryngology (AREA)
  • Hospice & Palliative Care (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Psychology (AREA)
  • AIDS & HIV (AREA)
  • Nutrition Science (AREA)

Abstract

Compuesto que responde a la fórmula general (III): ** ver fórmula** en la que: R 2 representa un grupo de fórmula general CHR 3CONHR 4 en la que R 3 representa un átomo de hidrógeno o un grupo metilo y R4 representa un átomo de hidrógeno o un grupo alquilo C1-3, cicloalquilo C3-5 o (piridin-4-il) metilo; y U representa un átomo de hidrógeno o un grupo nitro.

Description

Compuestos intermedios para la producción de dioxano-2-alquil-carbamatos.
La invención tiene como objetivo compuestos que responden a la fórmula general (III):
\vskip1.000000\baselineskip
1 
\vskip1.000000\baselineskip
en la que:
R_{2} representa un grupo de fórmula general CHR_{3}CONHR_{4} en la que R_{3} representa un átomo de hidrógeno o un grupo metilo y R_{4} representa un átomo de hidrógeno o un grupo alquilo C_{1-3}, cicloalquilo C_{3-5} o (piridin-4-il)metilo; y U representa un átomo de hidrógeno o un grupo nitro.
Los compuestos de fórmula general (III) pueden ser útiles, por ejemplo, como intermedios de síntesis de los compuestos de fórmula general (I):
\vskip1.000000\baselineskip
2 
\vskip1.000000\baselineskip
en la que:
R_{1} representa un grupo fenilo o naftalenilo opcionalmente sustituido con uno o varios átomos de halógeno o grupos hidroxi, ciano, nitro, alquilo C_{1-3}, alcoxi C_{1-3}, trifluorometilo, trifluorometoxi, benciloxi, cicloalquil C_{3-6}-O- o cicloalquil C_{3-6}-alcoxi C_{1-3};
R_{2} representa:
-
bien un grupo de fórmula general CHR_{3}CONHR_{4} en la que R_{3} representa un átomo de hidrógeno o un grupo metilo y R_{4} representa un átomo de hidrógeno o un grupo alquilo C_{1-3}, cicloalquilo C_{3-5} o (piridin-4-il)metilo,
-
bien un grupo 2,2,2-trifluoroetilo,
-
bien un grupo (imidazol-2-il)metilo,
-
bien un grupo (bencimidazol-2-il)metilo, o
-
bien un grupo fenilo opcionalmente sustituido con uno o varios átomos de halógeno o grupos ciano, nitro, alquilo C_{1-3}, alcoxi C_{1-3}, trifluorometilo o trifluorometoxi, y
n representa un número que va de1 a 3.
\vskip1.000000\baselineskip
Los compuestos de fórmula general (I) pueden contener uno o varios átomos de carbono asimétricos. Pueden existir en forma de enantiómeros o de diastereoisómeros. Los compuestos de fórmula general (I) pueden existir igualmente en forma de estereoisómeros cis o trans. Estos enantiómeros, diastereoisómeros y estereoisómeros, así como sus mezclas, incluyendo las mezclas racémicas, forman parte de la invención.
Los compuestos de fórmula (I) pueden existir en estado de bases o de sales de adición a ácidos. Tales sales de adición forman parte de la invención.
Estas sales se preparan ventajosamente con ácidos farmacéuticamente aceptables, si bien las sales de otros ácidos útiles, por ejemplo para la purificación o el aislamiento de los compuestos de fórmula (I), forman parte igualmente de la invención. Los compuestos de fórmula general (I) pueden encontrarse en forma de hidratos o de solvatos, es decir en forma de asociaciones o de combinaciones con una o varias moléculas de agua o con un disolvente. Tales hidratos y solvatos también forman parte de la invención.
\vskip1.000000\baselineskip
En el marco de la invención, se entiende por:
- C_{t-z}, donde t y z pueden tener los valores de 1 a 6, una cadena carbonada que puede tener de t a z átomos de carbono, por ejemplo, C_{1-3} una cadena carbonada que puede tener de 1 a 3 átomos de carbono;
- alquilo, un grupo alifático saturado, lineal o ramificado; por ejemplo un grupo alquilo C_{1-3} representa una cadena carbonada de 1 a 3 átomos de carbono, lineal o ramificada, más particularmente un metilo, etilo, propilo o isopropilo;
- cicloalquilo, un grupo alquilo cíclico, por ejemplo un grupo cicloalquilo C_{3-5} representa una cadena carbonada cíclica de 3 a 5 átomos de carbono, más particularmente un ciclopropilo, ciclobutilo o ciclopentilo;
- alcoxi, un grupo alquiloxi de cadena alifática saturada, lineal o ramificada;
- átomo de halógeno, un flúor, un cloro, un bromo o un yodo.
\vskip1.000000\baselineskip
Así, un método de preparación de los compuestos de fórmula general (I) (esquema 1) consiste en hacer reaccionar una amina de fórmula general (II), en la que R_{1} y n son tales como se han definido en la fórmula general (I), con un carbonato de fórmula general (III), en la que U representa un átomo de hidrógeno o un grupo nitro y R_{2} es tal como se ha definido en la fórmula general (I), en un disolvente tal como tolueno o dicloroetano, a una temperatura comprendida entre 0 y 80ºC.
Esquema 1
3
Los carbonatos de fórmula general (III) se pueden preparar según cualquier método descrito en la bibliografía, por ejemplo por reacción de un alcohol de fórmula general HOR_{2} con cloroformiato de fenilo o de 4-nitrofenilo, en presencia de una base tal como la trietilamina o la diisopropiletilamina.
Las aminas de fórmula general (II) se pueden preparar según los métodos de preparación descritos en las solicitudes de patente EP0461958, WO97/20836 y WO98/55474, opcionalmente adaptadas siguiendo técnicas conocidas por los expertos en la técnica.
Los ejemplos siguientes ilustran la preparación de algunos compuestos de la invención. Estos ejemplos no son limitantes y solamente ilustran la invención. Los microanálisis, los espectros de IR y de RMN y/o los análisis por CL-EM (cromatografía líquida acoplada con espectrometría de masas) confirman las estructuras y las purezas de los compuestos obtenidos.
Los números indicados entre paréntesis en los títulos de los ejemplos corresponden a los de la 1ª columna de la tabla siguiente.
\vskip1.000000\baselineskip
Ejemplo 1 trans-3-[5-(6-metoxinaftalen-1-il)-1,3-dioxan-2-il]propilcarbamato de 1H-imidazol-2-ilmetilo 1.1 (1-trifenilmetil-1H-imidazol-2-il)metilcarbonato de fenilo
A partir de 3 g (8,80 mmoles) de 1-trifenilmetil-1H-imidazol-2-metanol (J. Het. Chem., (1995), 32, 903-906) y 1,1 ml (8,80 mmoles) de cloroformiato de fenilo, se obtienen 3,9 g del producto que se usa tal cual en la etapa siguiente.
1.2 trans-3-[5-(6-metoxinaftalen-1-il)-1,3-dioxan-2-il]propilcarbamato de (1-trifenilmetil-1H-imidazol-2-il)metilo
A partir de 2,5 g (8,28 mmoles) de trans-3-[5-(6-metoxinaftalen-1-il)-1,3-dioxan-2-il]propanamina y 3,8 g (8,28 mmoles) de (1-trifenilmetil-1H-imidazol-2-il)metilcarbonato de fenilo, obtenido en la etapa 1.1, se obtienen 3,2 g de un sólido en forma amorfa.
1.3 trans-3-[5-(6-metoxinaftalen-1-il)-1,3-dioxan-2-il]propilcarbamato de 1H-imidazol-2-ilmetilo
A una disolución de 1,9 g (2,83 mmoles) de trans-3-[5-(6-metoxinaftalen-1-il)-1,3-dioxan-2-il]propilcarbamato de (1-trifenilmetil-1H-imidazol-2-il)metilo, obtenido en la etapa 1.2, en 150 ml de diclorometano, se le añade gota a gota, a temperatura ambiente, una disolución de 0,6 ml (2,83 mmoles) de ácido trifluoroacético en 2 ml de diclorometano y se agita la mezcla a temperatura ambiente durante 12 horas. Se concentra a presión reducida, se recoge el residuo con diclorometano y una disolución acuosa saturada de hidrógenocarbonato de sodio, se separa la fase orgánica, se la lava con una disolución acuosa saturada de cloruro de sodio, se la seca sobre sulfato de sodio, se concentra a presión reducida y se purifica el residuo por cromatografía sobre gel de sílice eluyendo con una mezcla 98/2/0,2 de diclorometano, metanol y amoniaco.
Después de recristalización en acetato de etilo se obtienen finalmente 0,820 g de producto puro.
Punto de fusión: 130-132ºC.
RMN ^{1}H: (CDCl_{3}) \delta (ppm) 10,0 (m ancho, 1H); 8,10 (d, 1H); 7,65 (d, 1H); 7,35 (dd, 1H); 7,25 (d, 1H); 7,15 (dd, 1H); 7,05 (dd, 1H); 7,00 (s, 2H); 5,15 (m+s, 3H); 4,70 (t, 1H); 4,30 (m, 2H); 3,95-3,90 (m, 6H); 3,30 (m, 2H); 1,85 (m, 4H).
\vskip1.000000\baselineskip
Ejemplo 2 trans-3-[5-(6-ciclopropilmetoxi-naftalen-1-il)-1,3-dioxan-2-il]-propilcarbamato de 2,2,2-trifluoroetilo
A una suspensión de 0,205 g (1,01 mmoles) de cloroformiato de 4-nitrofenilo y de 0,555 g (2,02 mmoles) de N,N-diisopropilaminoetilpoliestireno (Ps-DIEA, 2% DVB, título = 3,66 mmoles/g) en 7,1 ml de diclorometano, se le añaden, gota a gota y a temperatura ambiente, 0,075 ml (1,01 mmoles) de 2,2,2-trifluoroetanol. Se agita la mezcla de reacción con agitación orbital y a temperatura ambiente durante 16 horas. Se filtra la resina a través de un cartucho provisto de una frita y se lava con 4 ml de diclorometano. Se concentra el filtrado a presión reducida y se recoge el residuo oleoso así obtenido en 3,5 ml de 1,2-diclorometano. Se añaden sucesivamente 0,134 ml (0,78 mmoles) de N,N-diisopropiletilamina y 0,205 g (0,6 mmoles) de 3-[5-(6-ciclopropilmetoxi-naftalen-1-il)-1,3-dioxan-2-il]propilamina. Se calienta esta mezcla de reacción a 60ºC durante 16 horas. Después de enfriamiento, se lava con 20 ml de una disolución de sosa 1N. Se separan las fases y se filtra la fase orgánica a través de una frita hidrófoba. Se concentra el filtrado a presión reducida y se purifica el residuo obtenido mediante cromatografía en gel de sílice eluyendo con una mezcla 80/20 de ciclohexano y de acetato de etilo. Después de lavado con 5 ml de diisopropiléter, se obtienen 0,076 g de un sólido blanco.
LC-MS: M+H = 468
Punto de fusión: 105-107ºC
RMN ^{1}H: (CDCl_{3}) \delta (ppm): 8,15 (d, 1H); 7,65 (d, 1H); 7, 35 (dd, 1H); 7,25 (m, 1H); 7,15 (d, 1H); 7,10 (d, 1H); 5,15 (m ancho, 1H); 4,75 (t, 1H); 4,50 (c, 2H); 4,30 (dd, 2H); 4,10-3,80 (m, 5H); 3,40-3,20 (m, 2H); 1,90-1,65 (m, 4H); 1,45-1,20 (m, 1H); 0,75-0,60 (m, 2H); 0,50 -0,35 (m, 2H).

Claims (1)

1. Compuesto que responde a la fórmula general (III):
4
en la que:
\quad
R_{2} representa un grupo de fórmula general CHR_{3}CONHR_{4} en la que R_{3} representa un átomo de hidrógeno o un grupo metilo y R_{4} representa un átomo de hidrógeno o un grupo alquilo C_{1-3}, cicloalquilo C_{3-5} o (piridin-4-il)metilo; y
\quad
U representa un átomo de hidrógeno o un grupo nitro.
ES07013954T 2002-08-29 2003-08-27 Compuestos intermedios para la produccion de dioxano-2-alquil-carbamatos. Expired - Lifetime ES2329181T3 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0210707 2002-08-29
FR0210707A FR2843964B1 (fr) 2002-08-29 2002-08-29 Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique

Publications (1)

Publication Number Publication Date
ES2329181T3 true ES2329181T3 (es) 2009-11-23

Family

ID=31502974

Family Applications (2)

Application Number Title Priority Date Filing Date
ES07013954T Expired - Lifetime ES2329181T3 (es) 2002-08-29 2003-08-27 Compuestos intermedios para la produccion de dioxano-2-alquil-carbamatos.
ES03758282T Expired - Lifetime ES2312808T3 (es) 2002-08-29 2003-08-27 Derivados de dioxano-2-alquilcarbamatos, su preparacion y su aplicacion en terapeutica.

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES03758282T Expired - Lifetime ES2312808T3 (es) 2002-08-29 2003-08-27 Derivados de dioxano-2-alquilcarbamatos, su preparacion y su aplicacion en terapeutica.

Country Status (35)

Country Link
US (4) US7119116B2 (es)
EP (2) EP1537096B1 (es)
JP (2) JP4585854B2 (es)
KR (2) KR101051192B1 (es)
CN (3) CN101906071A (es)
AR (1) AR041053A1 (es)
AT (2) ATE434598T1 (es)
AU (1) AU2003274292B2 (es)
BR (1) BR0313846A (es)
CA (2) CA2700319C (es)
CO (1) CO5700820A2 (es)
CY (2) CY1108792T1 (es)
DE (2) DE60328138D1 (es)
DK (2) DK1537096T3 (es)
EA (1) EA008218B1 (es)
ES (2) ES2329181T3 (es)
FR (1) FR2843964B1 (es)
HK (2) HK1108157A1 (es)
HR (2) HRP20050190B1 (es)
IL (1) IL166882A (es)
IS (1) IS2733B (es)
MA (1) MA27390A1 (es)
ME (2) MEP24208A (es)
MX (1) MXPA05002319A (es)
NO (2) NO331165B1 (es)
NZ (1) NZ538404A (es)
PL (1) PL209339B1 (es)
PT (2) PT1840125E (es)
RS (2) RS20100169A (es)
SI (2) SI1840125T1 (es)
TN (1) TNSN05057A1 (es)
TW (2) TWI294878B (es)
UA (1) UA82847C2 (es)
WO (1) WO2004020430A2 (es)
ZA (1) ZA200501537B (es)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2843964B1 (fr) * 2002-08-29 2004-10-01 Sanofi Synthelabo Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique
CA2501506C (en) * 2002-10-07 2014-02-11 Daniele Piomelli Modulation of anxiety through blockade of anandamide hydrolysis
FR2854633B1 (fr) * 2003-05-07 2005-06-24 Sanofi Synthelabo Derives de piperidinyl-et piperazinyl-alkylcarbamates, leur preparation et leur application en therapeutique
FR2865205B1 (fr) * 2004-01-16 2006-02-24 Sanofi Synthelabo Derives de type aryloxyalkylcarbamates, leur preparation et leur application en therapeutique
FR2866886B1 (fr) 2004-02-26 2007-08-31 Sanofi Synthelabo Derives d'aryl-et d'heteroaryl-akylcarbamates, leur preparation et leur application en therapeutique
FR2866884B1 (fr) * 2004-02-26 2007-08-31 Sanofi Synthelabo Derives d'aryl-et d'heteroaryl-piperidinecarboxylates, leur preparation et leur application en therapeutique
FR2866885B1 (fr) * 2004-02-26 2007-08-31 Sanofi Synthelabo Derives de piperidinylalkylcarbamates, leur prepation et leur application en therapeutique
FR2866888B1 (fr) * 2004-02-26 2006-05-05 Sanofi Synthelabo Derives de alkylpiperazine- et alkylhomopiperazine- carboxylates, leur preparation et leur application en therapeutique
US7269708B2 (en) * 2004-04-20 2007-09-11 Rambus Inc. Memory controller for non-homogenous memory system
US20080103209A1 (en) * 2004-04-23 2008-05-01 The Regents Of The University Of California Compounds And Methods For Treating Non-Inflammatory Pain Using Ppar Alpha Agonists
DE102004039326A1 (de) * 2004-08-12 2006-02-16 Abbott Gmbh & Co. Kg Neue medizinische Verwendungen und Verfahren
MX2007010076A (es) 2005-02-17 2007-10-16 Astellas Pharma Inc Derivado de heterociclico-1-carboxilato que contiene nitrogeno no aromatico de piridilo.
FR2885364B1 (fr) * 2005-05-03 2007-06-29 Sanofi Aventis Sa Derives d'alkyl-, alkenyl-et alkynylcarbamates, leur preparation et leur application en therapeutique
US20080045513A1 (en) * 2006-08-18 2008-02-21 N.V. Organon Combination faah inhibitor and analgesic, anti-inflammatory or anti-pyretic agent
US20080089845A1 (en) * 2006-09-07 2008-04-17 N.V. Organon Methods for determining effective doses of fatty acid amide hydrolase inhibitors in vivo
US20090099240A1 (en) * 2006-10-02 2009-04-16 N.V. Organon Methods for treating energy metabolism disorders by inhibiting fatty acid amide hydrolase activity
CA2674359A1 (en) * 2006-11-20 2008-05-29 N.V. Organon Metabolically-stabilized inhibitors of fatty acid amide hydrolase
US8207226B1 (en) 2008-06-03 2012-06-26 Alcon Research, Ltd. Use of FAAH antagonists for treating dry eye and ocular pain
FR2941696B1 (fr) * 2009-02-05 2011-04-15 Sanofi Aventis Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique
TW201044234A (en) * 2009-06-08 2010-12-16 Chunghwa Picture Tubes Ltd Method of scanning touch panel
KR101820541B1 (ko) 2009-09-09 2018-02-28 다이닛본 스미토모 세이야꾸 가부시끼가이샤 8-옥소디히드로퓨린 유도체
US8274566B2 (en) * 2009-10-09 2012-09-25 John Mezzalingua Associates, Inc. Modulation analyzer and level measurement device
EP2545915A1 (en) 2011-07-11 2013-01-16 Sanofi 2-amino-2-oxoethyl trans-3-[5-(6-methoxy-naphtalen-1-yl)-1,3-dioxan-2-yl]propyl-carbamate for use in the treatment of persistent cancer pain
EP2545914A1 (en) 2011-07-11 2013-01-16 Sanofi 2-amino-2-oxoethyl trans-3-[5-(6-methoxy-naphtalen-1-yl)-1,3-dioxan-2-yl]propyl-carbamate for use in the treatment of persistent cancer pain
KR101653473B1 (ko) * 2012-01-06 2016-09-01 어바이드 테라퓨틱스, 인크. 카르바메이트 화합물 및 그의 제조 및 이용 방법
CN114835726B (zh) * 2022-03-24 2024-01-26 上海诺精生物科技有限公司 一类抑制肿瘤细胞干性的化合物及用途

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0461958B1 (fr) * 1990-06-15 1994-09-14 Synthelabo Dérivés de 2-(aminoalkyl)-5-(arylalkyl)-1,3-dioxanes, leur préparation et leur application en thérapeutique
US5173506A (en) * 1990-08-16 1992-12-22 Schering Corporation N-(mercaptoalkyl)ureas and carbamates
FR2742152B1 (fr) * 1995-12-06 1998-01-16 Synthelabo Derives de 5-naphtalen-1-yl-1,3-dioxanes, leur preparation et leur application en therapeutique
AT403579B (de) * 1995-12-07 1998-03-25 Agrolinz Melamin Gmbh Verfahren zur herstellung von hochreinem melamin
KR20010013435A (ko) 1997-06-05 2001-02-26 고든 라이트 5-나프탈렌-1-일-1,3-디옥산 유도체, 제조 및 치료에의 이용
KR20010042704A (ko) * 1998-04-16 2001-05-25 데이비드 비. 맥윌리암스 인테그린이 인테그린 수용체에 결합하는 것을 억제하는ｎ,ｎ-이치환된 아미드
FR2816938B1 (fr) * 2000-11-22 2003-01-03 Sanofi Synthelabo Derives de 3-aroylindole, leur procede de preparation et les compositions pharmaceutiques en contenant
FR2843964B1 (fr) * 2002-08-29 2004-10-01 Sanofi Synthelabo Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique

Also Published As

Publication number Publication date
PL209339B1 (pl) 2011-08-31
SI1840125T1 (sl) 2009-12-31
TWI337606B (en) 2011-02-21
US20100280076A1 (en) 2010-11-04
RS20050182A (en) 2007-09-21
TW200422294A (en) 2004-11-01
PL375753A1 (en) 2005-12-12
NZ538404A (en) 2007-07-27
JP4585854B2 (ja) 2010-11-24
ME00108B (me) 2010-10-10
FR2843964A1 (fr) 2004-03-05
US20060247290A1 (en) 2006-11-02
DK1840125T3 (da) 2009-11-09
BR0313846A (pt) 2005-09-27
PT1537096E (pt) 2008-12-11
KR20050059108A (ko) 2005-06-17
ES2312808T3 (es) 2009-03-01
NO331165B1 (no) 2011-10-24
KR101051192B1 (ko) 2011-07-21
NO20051051L (no) 2005-03-29
US20090286868A1 (en) 2009-11-19
CN1777595A (zh) 2006-05-24
EP1537096B1 (fr) 2008-09-24
AR041053A1 (es) 2005-04-27
DE60323754D1 (de) 2008-11-06
WO2004020430A3 (fr) 2004-04-22
US7119116B2 (en) 2006-10-10
KR20100134807A (ko) 2010-12-23
TW200738667A (en) 2007-10-16
ATE409184T1 (de) 2008-10-15
IS2733B (is) 2011-04-15
DE60328138D1 (de) 2009-08-06
KR101139160B1 (ko) 2012-04-26
HRP20050190A2 (en) 2005-10-31
TNSN05057A1 (fr) 2007-05-14
CN101445504B (zh) 2010-12-29
CA2496040A1 (en) 2004-03-11
EA200500268A1 (ru) 2005-10-27
AU2003274292A1 (en) 2004-03-19
WO2004020430A2 (fr) 2004-03-11
IS7699A (is) 2005-02-17
AU2003274292B2 (en) 2009-05-28
JP5244863B2 (ja) 2013-07-24
HK1108157A1 (en) 2008-05-02
MEP24208A (en) 2010-06-10
RS20100169A (en) 2011-04-30
TWI294878B (en) 2008-03-21
EP1840125B1 (fr) 2009-06-24
SI1537096T1 (sl) 2009-02-28
HRP20090270A2 (hr) 2009-09-30
HRP20050190B1 (hr) 2013-10-25
MA27390A1 (fr) 2005-06-01
CA2700319A1 (en) 2004-03-11
CY1108792T1 (el) 2014-04-09
US7777057B2 (en) 2010-08-17
PT1840125E (pt) 2009-09-29
US8119687B2 (en) 2012-02-21
EA008218B1 (ru) 2007-04-27
US20050182130A1 (en) 2005-08-18
DK1537096T3 (da) 2009-02-02
IL166882A (en) 2010-12-30
EP1840125A3 (fr) 2007-11-21
EP1840125A2 (fr) 2007-10-03
CN101445504A (zh) 2009-06-03
JP2010248218A (ja) 2010-11-04
EP1537096A2 (fr) 2005-06-08
CA2700319C (en) 2012-07-17
HRP20090270B1 (hr) 2015-12-04
MXPA05002319A (es) 2005-06-08
FR2843964B1 (fr) 2004-10-01
HK1074445A1 (en) 2005-11-11
NO335866B1 (no) 2015-03-09
RS51085B (sr) 2010-10-31
JP2005539045A (ja) 2005-12-22
CO5700820A2 (es) 2006-11-30
CA2496040C (en) 2011-04-05
UA82847C2 (en) 2008-05-26
ZA200501537B (en) 2006-10-25
NO20110598L (no) 2005-03-29
CY1109441T1 (el) 2014-08-13
CN100491368C (zh) 2009-05-27
ATE434598T1 (de) 2009-07-15
CN101906071A (zh) 2010-12-08

Similar Documents

Publication Publication Date Title
ES2329181T3 (es) Compuestos intermedios para la produccion de dioxano-2-alquil-carbamatos.
ES2218173T3 (es) Acidos 2-alquil-5-halogano-pent-4-enocarboxilicos y su fabricacion.
JP3235448B2 (ja) １，４−ベンゾジオキサン誘導体の製法
JP2011042690A (ja) ナプロキセンのニトロキシアルキルエステル
ES2847239T3 (es) Procedimientos para la preparación de 4-alcoxi-3-(acil o alquil)oxipicolinamidas
US10538539B2 (en) Method for preparing 3-((2S, 5S)-4-methylene-5-(3-oxopropyl)tetrahydrofurane-2-yl) propanol derivative, and intermediate therefor
EP0023097A1 (en) De-arylmethylation of N-mono- or N-diarylmethyl-beta-lactams; novel azetizinones having anti-bacterial activity
US4882429A (en) Stereospecific preparation of (3S,4R,5R)-3-(1-hydroxyethyl)-4-benzoyloxy-azeridinones from L-(-)-theonine
EP0111326B1 (en) Process for the manufacture of chiral azetidinones
EP1029856B1 (en) Process for the preparation of (2r, 3s)-3-amino-1,2-oxirane
WO2010097350A1 (en) A process for the preparation of an aldehyde beta-lactam compound
SU615854A3 (ru) Способ получени -диуретанов
JPS6135194B2 (es)
EP0255278B1 (en) Synthesis of azetidinones
WO2004002973A1 (ja) 光学活性１−置換アミノー２，３−エポキシプロパンの製造方法並びにその合成中間体およびそれらの製造方法
JP2005526826A (ja) キラル２−メチル−４−保護化ピペラジンの立体選択的アルキル化
SU1169527A3 (ru) Способ получени хлорформиатов @ - @ -алкиловых эфиров @ - @ - @ -алкилтартроновой кислоты
JP6158168B2 (ja) 光学活性２−ビニルシクロプロパン−１，１−ジカルボン酸エステルの製造法
US6388083B2 (en) Process for the synthesis of (2S)-phenyl-3-piperidone
Yamauchi et al. First highly stereoselective synthesis of (+)-dihydrosesamin, a trisubstituted tetrahydrofuran-type of lignan, by using highly erythro-selective aldol condensation
AU623306B2 (en) Process for producing isoxazole derivative
ES2363017T3 (es) Método para la producción de derivados de monoacetal de ciclopropano y sus compuestos intermedios.
JP3787809B2 (ja) オキサチアゼピン環の合成方法
KR100404685B1 (ko) 4-히드록시페닐글리신 무수물을 이용한 세팔로스포린화합물의 제조방법
CN102442948B (zh) 孟鲁司特钠中间体的制备方法