RU2002123882A - Производные индола, способ их получения и их применение - Google Patents

Производные индола, способ их получения и их применение

Info

Publication number
RU2002123882A
RU2002123882A RU2002123882/04A RU2002123882A RU2002123882A RU 2002123882 A RU2002123882 A RU 2002123882A RU 2002123882/04 A RU2002123882/04 A RU 2002123882/04A RU 2002123882 A RU2002123882 A RU 2002123882A RU 2002123882 A RU2002123882 A RU 2002123882A
Authority
RU
Russia
Prior art keywords
alkyl
substituted
cyano
alkoxy
hydroxy
Prior art date
Application number
RU2002123882/04A
Other languages
English (en)
Other versions
RU2259998C2 (ru
Inventor
Казухико ТОРИСУ (JP)
Казухико ТОРИСУ
Каору КОБАЯСИ (JP)
Каору КОБАЯСИ
Фумио НАМБУ (JP)
Фумио НАМБУ
Original Assignee
Оно Фармасьютикал Ко., Лтд. (Jp)
Оно Фармасьютикал Ко., Лтд.
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 Оно Фармасьютикал Ко., Лтд. (Jp), Оно Фармасьютикал Ко., Лтд. filed Critical Оно Фармасьютикал Ко., Лтд. (Jp)
Publication of RU2002123882A publication Critical patent/RU2002123882A/ru
Application granted granted Critical
Publication of RU2259998C2 publication Critical patent/RU2259998C2/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/423—Oxazoles condensed with carbocyclic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
    • 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
    • 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
    • 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
    • A61P17/04—Antipruritics
    • 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
    • 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
    • A61P27/12—Ophthalmic agents for cataracts
    • 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
    • A61P27/14—Decongestants or antiallergics
    • 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
    • A61P27/16—Otologicals
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • 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
    • 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
    • A61P9/10—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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pulmonology (AREA)
  • Dermatology (AREA)
  • Hematology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Anesthesiology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Claims (13)

1. Производное индола, представленное формулой (I)
Figure 00000001
где R1 представляет гидрокси, (С1-6)-алкокси или NR8R9, где R8 и R9, каждый независимо, представляет атом водорода, (С1-6)-алкил или SO2R13, где R13 представляет (С1-6)-алкил, насыщенное или ненасыщенное карбоциклическое кольцо (С3-15) или 4-15-членное гетероциклическое кольцо, содержащее 1-5 атомов азота, атомов серы и/или атомов кислорода;
R2 представляет атом водорода, (С1-6)-алкил, (С1-6)-алкокси, (С2-6)-алкоксиалкил, атом галогена, амино, тригалогенметил, циано, гидрокси, бензил или 4-метоксибензил;
R3 представляет атом водорода, (С1-6)-алкил, (С1-6)-алкокси, атом галогена, тригалогенметил, циано или гидрокси;
R4 и R5, каждый независимо, представляет атом водорода, (С1-6)-алкил, (С1-6)-алкокси, (С2-6)-алкоксиалкил, атом галогена, нитро, амино, тригалогенметил, циано или гидрокси;
D представляет простую связь, (С1-6)-алкилен, (С2-6)-алкенилен или (С1-6)-оксиалкилен;
в -G-R6:
1) G представляет простую связь, (С1-6)-алкилен, который может быть замещен 1-2 атомами кислорода и/или атомами серы, (С2-6)-алкенилен, который может быть замещен 1-2 атомами кислорода и/или атомами серы, где алкилен и алкенилен могут быть замещены гидрокси или (С1-4)-алкокси, -C(O)NH-, -NHC(O)-, -SO2NH-, -NHSO2- или диазо;
R6 представляет насыщенное или ненасыщенное карбоциклическое кольцо (С3-15) или 4-15-членное гетероциклическое кольцо, содержащее 1-5 атомов азота, атомов серы и/или атомов кислорода, где кольцо может быть замещено 1-5 заместителями, выбранными из (С1-6)-алкила, (С1-10)-алкокси, (С2-6)-алкоксиалкила, атома галогена, гидрокси, тригалогенметила, нитро, амино, фенила, фенокси, оксо, (С2-6)-ацила, (С1-6)-алкансульфонила и циано;
2) G и R6, взятые вместе, представляют (i) (C1-15)-алкил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, (ii) (С2-15)-алкенил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, или (iii) (C2-15)-алкинил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, где алкил, алкенил или алкинил могут быть замещены 1-12 заместителями, выбранными из числа (С1-6)-алкокси, атома галогена, гидрокси, циано, оксо и NR11R12, где R11 и R12, каждый независимо, представляет атом водорода, (С1-6)-алкил, (С2-6)-алкенил, фенил, бензоил, нафтил, фенил, замещенный (С1-6)-алкилом, или (С1-6)-алкил, замещенный фенилом или циано;
n=1-3;
m=1-3;
i=1-4;
Figure 00000002
Figure 00000003
представляет простую связь или двойную связь,
или его нетоксичная соль.
2. Производное индола по п.1, где D представляет простую связь, или его нетоксичная соль.
3. Производное индола по п.1, где D представляет (С1-6)-алкилен, или его нетоксичная соль.
4. Производное индола по п.1, где D представляет (С2-6)-алкенилен, или его нетоксичная соль.
5. Производное индола по п.1, где D представляет (С1-6)-оксиалкилен, или его нетоксичная соль.
6. Производное индола по п.1, где R6 представляет насыщенное или ненасыщенное карбоциклическое кольцо (С3-15), где кольцо может быть замещено 1-5 группами, выбранными из группы, состоящей из (С1-6)-алкила, (С1-10)-алкокси, (С2-6)-алкоксиалкила, атома галогена, тригалогенметила, гидрокси, нитро, амино, фенила, фенокси, оксо, (С2-6)-ацила, (С1-6)-алкансульфонила и циано, или его нетоксичная соль.
7. Производное индола по п.1, где R6 представляет 4-15-членное гетероциклическое кольцо, содержащее 1-5 атомов азота, атомов серы и/или атомов кислорода, где кольцо может быть замещено 1-5 группами, выбранными из группы, состоящей из (С1-6)-алкила, (С1-10)-алкокси, (С2-6)-алкоксиалкила, атома галогена, тригалогенметила, гидрокси, нитро, амино, фенила, фенокси, оксо, (С2-6)-ацила, (С1-6)-алкансульфонила и циано, или его нетоксичная соль.
8. Производное индола по п.1, где G и R6, взятые вместе, представляют (i) (C1-15)-алкил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, (ii) (С2-15)-алкенил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, или (iii) (С2-15)-алкинил, который может быть замещен 1-5 атомами кислорода и/или атомами серы, где алкил, алкенил или алкинил могут быть замещены 1-12 заместителями, выбранными из группы, состоящей из (С1-6)-алкокси, атома галогена, гидрокси, циано, оксо и NR11R12, где R11 и R12, каждый независимо, представляет атом водорода, (С1-6)-алкил, (С2-6)-алкенил, фенил, бензоил, нафтил, фенил, замещенный (С1-6)-алкилом, или (С1-6)-алкил, замещенный фенилом или циано, или его нетоксичная соль.
9. Способ получения карбоновой кислоты, представленной формулой (Iа)
Figure 00000004
где все символы имеют значения, указанные ниже,
включающий реакцию удаления защитной группы соединения, представленного формулой (IV)
Figure 00000005
где R20 представляет аллильную или бензильную группу, и другие символы имеют значения, указанные в п.1.
10. Способ получения соединения, представленного формулой (Ib)
Figure 00000006
где все символы имеют значения, указанные ниже,
включающий реакцию этерификации карбоновой кислоты, представленной формулой (Iа)
Figure 00000007
где все символы имеют значения, указанные ниже, спиртом, представленным формулой
R10-OH, (III)
где R10 представляет (С1-6)-алкил,
с последующей, необязательно, реакцией удаления защитной группы.
11. Способ получения соединения, представленного формулой (Iс)
Figure 00000008
где все символы имеют значения, указанные ниже,
включающий реакцию амидирования карбоновой кислоты, представленной формулой (Iа)
Figure 00000009
где все символы имеют значения, указанные в п.1,
амином, представленным формулой (II)
NR10R11, (II)
где все символы имеют значения, указанные в п.1,
с последующей, необязательно, реакцией удаления защитной группы.
12. Антагонист DP-рецептора, содержащий в качестве активного ингредиента производное индола формулы (I) или его нетоксичную соль.
13. 2-Метилиндол-4-уксусная кислота.
RU2002123882/04A 2000-03-09 2001-03-08 Производные индола, способ их получения и их применение RU2259998C2 (ru)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2000-64696 2000-03-09
JP2000064696 2000-03-09
JP2000-231857 2000-07-31
JP2000231857 2000-07-31

Publications (2)

Publication Number Publication Date
RU2002123882A true RU2002123882A (ru) 2004-03-20
RU2259998C2 RU2259998C2 (ru) 2005-09-10

Family

ID=26587084

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2002123882/04A RU2259998C2 (ru) 2000-03-09 2001-03-08 Производные индола, способ их получения и их применение

Country Status (14)

Country Link
US (2) US6743793B2 (ru)
EP (1) EP1262475A4 (ru)
JP (1) JP4292742B2 (ru)
KR (1) KR20030010589A (ru)
CN (1) CN1179945C (ru)
AU (1) AU2001241068A1 (ru)
BR (1) BR0109050A (ru)
CA (1) CA2402174A1 (ru)
HU (1) HUP0301493A2 (ru)
MX (1) MXPA02008801A (ru)
NO (1) NO20024281L (ru)
NZ (1) NZ521192A (ru)
RU (1) RU2259998C2 (ru)
WO (1) WO2001066520A1 (ru)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2573830C2 (ru) * 2010-03-25 2016-01-27 Вертекс Фармасьютикалз Инкорпорейтед ТВЕРДЫЕ ФОРМЫ (R)-1-(2,2-ДИФТОРБЕНЗО[d][1,3]ДИОКСОЛ-5-ИЛ)-N-(2,3-ДИГИДРОКСИПРОПИЛ)-6-ФТОР-2-(1-ГИДРОКСИ-2-МЕТИЛПРОПАН-2-ИЛ)-1H-ИНДОЛ-5-ИЛ)ЦИКЛОПРОПАНКАРБОКСАМИДА

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7135495B2 (en) * 2000-03-09 2006-11-14 Ono Pharmaceutical Co., Ltd. Indole derivatives
US20040092750A1 (en) * 2001-03-01 2004-05-13 Tomoyuki Hasegawa 2-methylindole-4-acetic acid, process for producing the same, and process for producing intermediate therefor
JPWO2003022814A1 (ja) * 2001-09-07 2004-12-24 小野薬品工業株式会社 インドール誘導体化合物
JP4292402B2 (ja) * 2001-09-07 2009-07-08 小野薬品工業株式会社 インドール誘導体化合物、それらの製造方法およびそれらを有効成分として含有する薬剤
CA2476936A1 (en) * 2002-02-20 2003-08-28 Chih-Hung Lee Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (vr1) receptor
MXPA04009095A (es) 2002-03-19 2004-12-06 Ono Pharmaceutical Co Compuesto de acido carboxilico y agente farmaceutico que comprende el compuesto como ingrediente activo.
EP2423190A1 (en) 2002-05-16 2012-02-29 Shionogi&Co., Ltd. Compounds Exhibiting PGD 2 Receptor Antagonism
JP2004010601A (ja) * 2002-06-11 2004-01-15 Nippon Steel Chem Co Ltd インドール誘導体の製造方法及びそのための有用な中間体
DE60333762D1 (de) * 2002-08-23 2010-09-23 Novartis Vaccines & Diagnostic Pyrrolverbindungen als glykogen synthase kinase 3 inhibitoren
WO2004030674A1 (ja) * 2002-09-30 2004-04-15 Shionogi & Co., Ltd. プロスタグランジンｄ２、プロスタグランジンｄ２アゴニストおよびプロスタグランジンｄ２アンタゴニストの新規用途
GB0224557D0 (en) * 2002-10-22 2002-11-27 Glaxo Group Ltd Novel compounds
US6933311B2 (en) * 2003-02-11 2005-08-23 Abbott Laboratories Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
JPWO2004078719A1 (ja) * 2003-03-06 2006-06-08 小野薬品工業株式会社 インドール誘導体化合物およびその化合物を有効成分とする薬剤
AR041089A1 (es) 2003-05-15 2005-05-04 Merck & Co Inc Procedimiento y composiciones farmaceutiicas para tratar aterosclerosis, dislipidemias y afecciones relacionadas
TWI341838B (en) * 2003-09-17 2011-05-11 Ono Pharmaceutical Co Carboxylic acid compound and pharmaceutical composition containg same as active ingredient
US7268159B2 (en) * 2003-09-25 2007-09-11 Wyeth Substituted indoles
PE20050483A1 (es) 2003-10-31 2005-08-25 Arena Pharm Inc Derivados de tetrazol de formula (i), sus composiciones farmaceuticas y procesos para producir composiciones farmaceuticas
US20070244107A1 (en) * 2004-08-25 2007-10-18 Waters M Gerard Method of Treating Atherosclerosis, Dyslipidemias and Related Conditions
CN101056635A (zh) * 2004-11-04 2007-10-17 默克公司 烟酸受体激动剂、含有该化合物的组合物及治疗方法
WO2006057922A2 (en) * 2004-11-23 2006-06-01 Merck & Co., Inc. Niacin receptor agonists, compositions containing such compounds and methods of treatment
PE20060949A1 (es) 2004-12-23 2006-10-11 Arena Pharm Inc Derivados fusionados de pirazol como agonistas del receptor de niacina
WO2006068162A1 (ja) * 2004-12-24 2006-06-29 Shionogi & Co., Ltd. 慢性閉塞性肺疾患の治療剤
CA2598273A1 (en) * 2005-02-17 2006-08-24 Merck & Co., Inc. Method of treating atherosclerosis, dyslipidemias and related conditions
EP1931658A2 (en) * 2005-09-07 2008-06-18 Plexxikon, Inc. 1 , 4 and 1 , 5-disubstituted indole derivatives for use as ppar active compounds
GB2431927B (en) 2005-11-04 2010-03-17 Amira Pharmaceuticals Inc 5-Lipoxygenase-activating protein (FLAP) inhibitors
US7977359B2 (en) 2005-11-04 2011-07-12 Amira Pharmaceuticals, Inc. 5-lipdxygenase-activating protein (FLAP) inhibitors
US8399666B2 (en) 2005-11-04 2013-03-19 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
EP2007756B1 (en) * 2006-04-07 2015-08-26 Vertex Pharmaceuticals Incorporated Modulators of atp-binding cassette transporters
EP2037967B1 (en) 2006-06-16 2016-12-07 The Trustees Of The University Of Pennsylvania Prostaglandin d2 receptor antagonists for treating androgenetic alopecia
KR20090025367A (ko) * 2006-06-28 2009-03-10 가부시키가이샤산와카가쿠켄큐쇼 신규 6-5계 이환식 복소환 유도체 및 그 의약용도
EP2054390B1 (en) * 2006-08-25 2012-04-11 Abbott Laboratories Indazole derivatives that inhibit trpv1 and uses thereof
CN101622230B (zh) 2007-02-26 2012-08-22 默克弗罗斯特加拿大有限公司 作为ep4受体拮抗剂的吲哚和二氢吲哚环丙基酰胺衍生物
TWI410410B (zh) 2007-08-10 2013-10-01 Ono Pharmaceutical Co Phenylacetic acid compounds
EP2285803A4 (en) 2008-05-23 2011-10-05 Amira Pharmaceuticals Inc Inhibitor of 5-Lipoxygenase Activating Protein
WO2010030360A1 (en) 2008-09-11 2010-03-18 Arena Pharmaceuticals, Inc. 3H-IMIDAZO[4,5-b]PYRIDIN-5-OL DERIVATIVES USEFUL IN THE TREATMENT OF GPR81 RECEPTOR DISORDERS
WO2010070021A1 (en) * 2008-12-18 2010-06-24 Glaxo Group Limited Novel compounds
US8367660B2 (en) * 2008-12-30 2013-02-05 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
US8906951B1 (en) 2013-06-24 2014-12-09 Tigercat Pharma, Inc. Use of NK-1 receptor antagonists in pruritus
US9198898B2 (en) 2013-06-24 2015-12-01 Tigercat Pharma, Inc. Use of NK-1 receptor antagonists in pruritus
PE20180573A1 (es) * 2015-07-20 2018-04-04 Genzyme Corp Inhibidores del receptor del factor estimulador de colonias 1 (csf-1r)
EP4267573A1 (en) 2020-12-23 2023-11-01 Genzyme Corporation Deuterated colony stimulating factor-1 receptor (csf-1r) inhibitors

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT290523B (de) * 1962-01-05 1971-06-11 Merck & Co Inc Verfahren zur Herstellung neuer α-(3-Indolyl)-carbonsäuren
GB8704158D0 (en) 1987-02-23 1987-04-01 Wellcome Found Substituted hydantoin compounds
GB9011589D0 (en) 1990-05-24 1990-07-11 Wellcome Found Amino bicyclic compounds
JPH0764841B2 (ja) * 1990-10-03 1995-07-12 ファイザー製薬株式会社 インドール誘導体およびその用途
CA2225250C (en) 1995-06-21 2005-03-22 Shionogi & Co., Ltd. Bicyclic amino derivatives and pgd2 antagonist containing the same
JPH09176162A (ja) * 1995-12-22 1997-07-08 Toubishi Yakuhin Kogyo Kk チアゾリジンジオン誘導体及びその製造法並びにそれを含む医薬組成物
DE19641681A1 (de) 1996-10-10 1998-07-23 Peter Dr Bracher Verfahren zur Abwasserreinigung in Kleinkläranlagen
WO1998025915A1 (fr) 1996-12-12 1998-06-18 Shionogi & Co., Ltd. Derives d'amide d'acide benzenecarboxylique condenses heterocycliques et antagonistes pgd2 renfermant ces derives
BR9714016A (pt) 1996-12-13 2000-02-29 Shionogi & Co Derivados de benzotiofenocarboxamida e antagonistas a pgd2, que compreendem os mesmos

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2573830C2 (ru) * 2010-03-25 2016-01-27 Вертекс Фармасьютикалз Инкорпорейтед ТВЕРДЫЕ ФОРМЫ (R)-1-(2,2-ДИФТОРБЕНЗО[d][1,3]ДИОКСОЛ-5-ИЛ)-N-(2,3-ДИГИДРОКСИПРОПИЛ)-6-ФТОР-2-(1-ГИДРОКСИ-2-МЕТИЛПРОПАН-2-ИЛ)-1H-ИНДОЛ-5-ИЛ)ЦИКЛОПРОПАНКАРБОКСАМИДА

Also Published As

Publication number Publication date
CA2402174A1 (en) 2001-09-13
CN1427824A (zh) 2003-07-02
US20030176400A1 (en) 2003-09-18
EP1262475A4 (en) 2005-01-05
WO2001066520A1 (fr) 2001-09-13
US6743793B2 (en) 2004-06-01
EP1262475A1 (en) 2002-12-04
MXPA02008801A (es) 2003-07-07
RU2259998C2 (ru) 2005-09-10
NZ521192A (en) 2005-01-28
JP4292742B2 (ja) 2009-07-08
NO20024281L (no) 2002-11-08
HUP0301493A2 (hu) 2003-08-28
US7098234B2 (en) 2006-08-29
KR20030010589A (ko) 2003-02-05
BR0109050A (pt) 2004-04-27
US20040180885A1 (en) 2004-09-16
AU2001241068A1 (en) 2001-09-17
CN1179945C (zh) 2004-12-15
NO20024281D0 (no) 2002-09-06

Similar Documents

Publication Publication Date Title
RU2002123882A (ru) Производные индола, способ их получения и их применение
RU2397171C2 (ru) 9-замещенное производное 8-оксоаденина и лекарственное средство
RU2009102832A (ru) С-фенил-1-тилоглюцитолы
RU2012140011A (ru) Получение 6'-о-сиалиллактозы и промежуточные соединения
JP2008520630A5 (ru)
RU95117719A (ru) Производные ароил-пиперидина
RU2007138582A (ru) Пероральные дозированные формы производных гемцитабина
KR900016186A (ko) 5-알킬퀴놀론 카복실산
RU2013112946A (ru) Способ получения промежуточных соединений для получения ингибиторов nep
DE3751764T2 (de) Verfahren zur Herstellung von N1,N4-Diethylspermin
KR920703560A (ko) 시스-β-페닐글리시딘-(2R,3R)산의 제조방법
EP2289888A3 (en) Epoxycarboxylic acid amides, azides and amino alcohols and processes for preparation of alpha-keto amides by using them
RU2004121776A (ru) Производные тетрагидрокарбазола, способ получения производных тетрагидрокарбазола (варианты), их применение (варианты) и фармацевтическая композиция, обладающая активностью антагониста гонадотропин-рилизинг-гормона (варианты)
RU2002102551A (ru) Новые производные пиперазинилалкилтиопиримидина, содержащие их фармацевтические композиции и способ получения активного вещества
RU2007106927A (ru) Синтез амидов 6,7,-дигидро-5н-имидазо [1.2-а] имидазол-3-сульфоновой кислоты
HU212494B (en) Process for producing new tetraline derivatives and pharmaceutical compositions containing them as active components
KR927003533A (ko) 피페라진 유도체
KR910002891A (ko) 신규한 s-아데노실 메티오닌 디카르복실라제 억제제
RU2002118320A (ru) Новый способ получения α-(2,4-дисульфофенил)-N-трет-бутилнитрона и его фармакологически приемлемых солей
RU2000108477A (ru) Стереоизомерные индольные соединения, способ их получения и их использование
JP2005538151A5 (ru)
BRPI0702865A2 (pt) processos para preparaÇço do Ácido 3-isobutilglutÁrico e de (s)- pregabalin, a partir de combinaÇÕes de composiÇÕes com fàrmulas especÍficas para uso na dita preparaÇço
JP2004529156A5 (ru)
DE69831612D1 (de) Verfahren zu herstellung von 3(2h)pyridazinon-4-substituierte amino-5-chloro derivate
DE69809205T2 (de) Verfahren zur herstellung von azyklischen nukleosiden

Legal Events

Date Code Title Description
MM4A The patent is invalid due to non-payment of fees

Effective date: 20060309