CA2402199C - Amidino compounds useful as nitric oxide synthase inhibitors - Google Patents

Amidino compounds useful as nitric oxide synthase inhibitors Download PDF

Info

Publication number
CA2402199C
CA2402199C CA2402199A CA2402199A CA2402199C CA 2402199 C CA2402199 C CA 2402199C CA 2402199 A CA2402199 A CA 2402199A CA 2402199 A CA2402199 A CA 2402199A CA 2402199 C CA2402199 C CA 2402199C
Authority
CA
Canada
Prior art keywords
group
alkyl
compound
acceptable salt
acid
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 - Fee Related
Application number
CA2402199A
Other languages
English (en)
French (fr)
Other versions
CA2402199A1 (en
Inventor
Ronald Keith Webber
Alok K. Awasthi
Arija A. Bergmanis
Richard C. Durley
Kam F. Fok
Scott S. Ganser
Timothy J. Hagen
Ann E. Hallinan
Donald W. Hansen
Brian S. Hickory
Pamela T. Manning
Michael Mao
Alan E. Moormann
Barnett S. Pitzele
Michelle A. Promo
Richard R. Schartman
Jeffrey A. Scholten
Jeffrey S. Snyder
Mihaly V. Toth
Mahima Trivedi
Sofya Tsymbalov
Foe Siong Tjoeng
Richard Vonder Embse
Gopichand Yalamanchili
W. Gary Phillips
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.)
Pharmacia LLC
Original Assignee
Pharmacia LLC
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 Pharmacia LLC filed Critical Pharmacia LLC
Publication of CA2402199A1 publication Critical patent/CA2402199A1/en
Application granted granted Critical
Publication of CA2402199C publication Critical patent/CA2402199C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P13/12—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
    • 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
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • 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
    • 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
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • 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
    • A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34—Tobacco-abuse
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • 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
    • 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
    • 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
    • A61P37/02—Immunomodulators
    • 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
    • A61P39/00—General protective or antinoxious agents
    • A61P39/02—Antidotes
    • 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
    • A61P7/06—Antianaemics
    • 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
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Diabetes (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • Pulmonology (AREA)
  • Dermatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Reproductive Health (AREA)
  • Rheumatology (AREA)
  • Obesity (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychology (AREA)
  • Emergency Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Transplantation (AREA)
  • Otolaryngology (AREA)
CA2402199A 2000-03-24 2001-03-23 Amidino compounds useful as nitric oxide synthase inhibitors Expired - Fee Related CA2402199C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US19192300P 2000-03-24 2000-03-24
US60/191,923 2000-03-24
PCT/US2001/009431 WO2001072702A2 (en) 2000-03-24 2001-03-23 Amidino compounds useful as nitric oxide synthase inhibitors

Publications (2)

Publication Number Publication Date
CA2402199A1 CA2402199A1 (en) 2001-10-04
CA2402199C true CA2402199C (en) 2010-08-03

Family

ID=22707469

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2402436A Expired - Fee Related CA2402436C (en) 2000-03-24 2001-03-23 Amidino compound and salts thereof useful as nitric oxide synthase inhibitors
CA2402199A Expired - Fee Related CA2402199C (en) 2000-03-24 2001-03-23 Amidino compounds useful as nitric oxide synthase inhibitors

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA2402436A Expired - Fee Related CA2402436C (en) 2000-03-24 2001-03-23 Amidino compound and salts thereof useful as nitric oxide synthase inhibitors

Country Status (21)

Country Link
US (5) US6586474B2 (enExample)
EP (2) EP1265860B1 (enExample)
JP (2) JP4205340B2 (enExample)
KR (1) KR100835265B1 (enExample)
CN (1) CN1294117C (enExample)
AR (1) AR033359A1 (enExample)
AT (2) ATE313525T1 (enExample)
AU (4) AU2001247745B2 (enExample)
BR (1) BR0109386A (enExample)
CA (2) CA2402436C (enExample)
DE (2) DE60110902T2 (enExample)
DK (2) DK1265859T3 (enExample)
ES (2) ES2256223T3 (enExample)
GE (1) GEP20094625B (enExample)
MX (1) MXPA02009282A (enExample)
MY (1) MY135721A (enExample)
NZ (4) NZ532073A (enExample)
PT (1) PT1265860E (enExample)
TW (1) TWI294417B (enExample)
WO (2) WO2001072702A2 (enExample)
ZA (2) ZA200206459B (enExample)

Families Citing this family (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA200206459B (en) * 2000-03-24 2003-08-13 Pharmacia Corp Amidino compound and salts thereof useful as nitric oxide synthase inhibitors.
US7879840B2 (en) 2005-08-25 2011-02-01 The Trustees Of Columbia University In The City Of New York Agents for preventing and treating disorders involving modulation of the RyR receptors
US8022058B2 (en) 2000-05-10 2011-09-20 The Trustees Of Columbia University In The City Of New York Agents for preventing and treating disorders involving modulation of the RyR receptors
US7718644B2 (en) 2004-01-22 2010-05-18 The Trustees Of Columbia University In The City Of New York Anti-arrhythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) and uses thereof
US7393652B2 (en) 2000-05-10 2008-07-01 The Trustees Of Columbia University In The City Of New York Methods for identifying a chemical compound that directly enhances binding of FKBP12.6 to PKA-phosphorylated type 2 ryanodine receptor (RyR2)
US7012098B2 (en) * 2001-03-23 2006-03-14 Pharmacia Corporation Inhibitors of inducible nitric oxide synthase for chemoprevention and treatment of cancers
WO2002078617A2 (en) 2001-03-28 2002-10-10 University Of South Florida Materials and methods for treatment of cancer and identification of anti-cancer compounds
PE20021017A1 (es) * 2001-04-03 2002-11-24 Pharmacia Corp Composicion parenteral reconstituible
DE10141650C1 (de) 2001-08-24 2002-11-28 Lohmann Therapie Syst Lts Transdermales Therapeutisches System mit Fentanyl bzw. verwandten Substanzen
US20030109522A1 (en) * 2001-09-24 2003-06-12 Manning Pamela T. Ophthalmologic treatment methods using selective iNOS inhibitors
US20030119826A1 (en) * 2001-09-24 2003-06-26 Pharmacia Corporation Neuroprotective treatment methods using selective iNOS inhibitors
RU2004114552A (ru) * 2001-11-13 2005-02-20 Фармация Корпорейшн (Us) Пероральная дозированная форма сульфонамидного пролекарства
PL373952A1 (en) * 2002-05-16 2005-09-19 Pharmacia Corporation Methods for the treatment of respiratory diseases and conditions using a selective inos inhibitor
WO2003097050A2 (en) * 2002-05-16 2003-11-27 Pharmacia Corporation A selective inos inhibitor and a pde inhibitor in combination for the treatment of respiratory diseases
EP2287152B1 (en) 2002-06-05 2015-01-14 Kaneka Corporation Process for producing optically active alpha-methylcysteine derivative
BR0313204A (pt) * 2002-08-02 2005-06-28 Pharmacia Corp Métodos para tratamento e prevenção de condições gastrointestinais
AU2003269406A1 (en) * 2002-11-01 2004-05-25 Pharmacia & Upjohn Company Llc Process for preparing s-(2-aminoethyl)-2-methyl-l-cysteine
US7544678B2 (en) 2002-11-05 2009-06-09 The Trustees Of Columbia University In The City Of New York Anti-arrythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2)
JP2006513238A (ja) * 2002-12-19 2006-04-20 ファルマシア・コーポレーション 吸湿性薬物を含む非‐吸湿性製剤
WO2004064767A2 (en) * 2003-01-23 2004-08-05 Kahn Nighat N Nitric oxide inducing agents
DE10308580B3 (de) * 2003-02-27 2004-09-09 Consortium für elektrochemische Industrie GmbH Verfahren zur elektrophilen Substitution von Thiazolidinen oder Oxazolidinen
EP1603450A4 (en) 2003-03-07 2009-07-29 Univ Columbia PROCEDURE BASED ON TYPE 1 RYANODIN RECEPTOR
JP2006519835A (ja) * 2003-03-11 2006-08-31 ファルマシア コーポレイション Ｓ−［２−〔（１−イミノエチル）アミノ〕エチル］−２−メチル−ｌ−システインサリチル酸１水和物の結晶質塩
MXPA05009302A (es) * 2003-03-11 2005-10-05 Pharmacia Corp Sal cristalina de maleato de s-[2-[(1-iminoetil)amino]etil]-2-metil-l-cisteina.
JP2006519832A (ja) * 2003-03-11 2006-08-31 ファルマシア・コーポレーション 化合物から対イオンを選択的に除去するための方法およびそのような方法から誘導される化合物
KR20090048521A (ko) * 2003-03-11 2009-05-13 파마시아 코포레이션 에스-[2-[(1-이미노에틸)아미노]에틸]-2-메틸-엘-시스테인 말레에이트 히드로클로라이드 결정질 염
WO2004080954A1 (en) * 2003-03-11 2004-09-23 Pharmacia Corporation S-[2-[(1-iminoethyl)amino]ethyl]-2-methyl-l-cysteine maleate form ii crystalline salt
US20040186046A1 (en) * 2003-03-17 2004-09-23 Pfizer Inc Treatment of type 1 diabetes with PDE5 inhibitors
EP1634957B1 (en) * 2003-04-08 2008-10-08 Mitsubishi Gas Chemical Company, Inc. 2-alkylcysteinamide or salt thereof, process for producing these, and use of these
JP4735263B2 (ja) * 2003-11-18 2011-07-27 三菱瓦斯化学株式会社 光学活性２−アルキルシステインの製造方法、並びにその誘導体及び製造方法
US8710045B2 (en) 2004-01-22 2014-04-29 The Trustees Of Columbia University In The City Of New York Agents for preventing and treating disorders involving modulation of the ryanodine receptors
US20060154981A1 (en) * 2005-01-12 2006-07-13 Alcon, Inc. Method of reducing intraocular pressure and treating glaucoma
US7704990B2 (en) 2005-08-25 2010-04-27 The Trustees Of Columbia University In The City Of New York Agents for preventing and treating disorders involving modulation of the RyR receptors
EP1986656A4 (en) * 2006-02-02 2012-05-16 Univ South Florida WITHACNISTINE COMPOUNDS FOR THE TREATMENT OF CANCER
CA2644613A1 (en) * 2006-03-07 2007-09-13 Endacea, Inc. Compositions and methods for treating respiratory disorders
US20090186854A1 (en) * 2006-03-23 2009-07-23 Meditor Pharmaceuticals Ltd. S-alkylisothiouronium derivatives for the treatment of inflammatory diseases
US7820689B2 (en) * 2006-08-10 2010-10-26 Hua-Lin Wu Methods and compositions for preventing or treating cardiovascular disease
CN101758337B (zh) 2009-12-03 2012-02-15 湖南阿斯达生化科技有限公司 一种助焊剂用非卤素活性剂
US20150231215A1 (en) 2012-06-22 2015-08-20 Randolph J. Noelle VISTA Antagonist and Methods of Use
BR112012024565B1 (pt) 2010-03-26 2022-02-08 Trustees Of Dartmouth College Proteína de fusão vista imunossupressora multimérica isolada ou recombinante e composição
US10745467B2 (en) 2010-03-26 2020-08-18 The Trustees Of Dartmouth College VISTA-Ig for treatment of autoimmune, allergic and inflammatory disorders
US9293197B2 (en) 2011-08-15 2016-03-22 Lockheed Martin Corporation Reconfigurable phase change material masks for electro-optical compressive sensing
FI3421486T3 (fi) 2012-06-22 2023-12-15 Dartmouth College Uusia vista-ig-rakenteita ja vista-ig:n käyttö autoimmuuni-, allergia- ja tulehdushäiriöiden hoitamiseksi
US9890215B2 (en) 2012-06-22 2018-02-13 King's College London Vista modulators for diagnosis and treatment of cancer
JP6368308B2 (ja) 2012-09-07 2018-08-01 トラスティーズ・オブ・ダートマス・カレッジ 癌の診断および治療のためのｖｉｓｔａ調節剤
US9340446B1 (en) 2013-02-04 2016-05-17 Lockheed Martin Corporation Optical apparatus and method of forming a gradient index device
WO2014178433A1 (ja) 2013-05-02 2014-11-06 株式会社エーピーアイ コーポレーション α－置換システインもしくはその塩又はα－置換システイン合成中間体の製造方法
EP3043788B1 (en) 2013-09-13 2023-06-07 Replicon Health OY D-glyceric acid or dl-glyceric acid for use in the treatment of degeneration diseases related to aging
US10273301B2 (en) 2013-12-24 2019-04-30 Janssen Pharmaceutica Nv Anti-vista antibodies and fragments
US11014987B2 (en) 2013-12-24 2021-05-25 Janssen Pharmaceutics Nv Anti-vista antibodies and fragments, uses thereof, and methods of identifying same
WO2015191881A2 (en) 2014-06-11 2015-12-17 Green Kathy A Use of vista agonists and antagonists to suppress or enhance humoral immunity
US10437083B1 (en) 2014-10-20 2019-10-08 Lockheed Martin Corporation Individually addressable infrared mask array
WO2016090347A1 (en) 2014-12-05 2016-06-09 Immunext, Inc. Identification of vsig8 as the putative vista receptor and its use thereof to produce vista/vsig8 modulators
EP3722314A1 (en) 2015-06-24 2020-10-14 Janssen Pharmaceutica NV Anti-vista antibodies and fragments
GB201512635D0 (en) 2015-07-17 2015-08-26 Ucl Business Plc Uses of therapeutic compounds
CN109069626A (zh) 2016-02-12 2018-12-21 詹森药业有限公司 抗-vista(b7h5)抗体
US11525000B2 (en) 2016-04-15 2022-12-13 Immunext, Inc. Anti-human VISTA antibodies and use thereof
US9969647B2 (en) 2016-05-17 2018-05-15 Lockheed Martin Energy, Llc Glass composites having a gradient index of refraction and methods for production thereof
US9908808B1 (en) 2016-08-18 2018-03-06 Lockheed Martin Corporation Ternary glass materials with low refractive index variability
EP3398941A1 (en) * 2017-05-03 2018-11-07 AXXAM S.p.A. Heterocyclic p2x7 antagonists

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2036770C (en) 1990-02-26 2003-09-09 Jeffrey P. Whitten Inhibitors of nitric oxide biosynthesis
US5132453A (en) 1991-03-22 1992-07-21 Cornell Research Foundation, Inc. N6 -(hydrazinoiminomethyl)lysine and method of inhibiting nitric oxide formation in body
JP2648897B2 (ja) 1991-07-01 1997-09-03 塩野義製薬株式会社 ピリミジン誘導体
GB9127376D0 (en) 1991-12-24 1992-02-19 Wellcome Found Amidino derivatives
GB9203347D0 (en) 1992-02-17 1992-04-01 Wellcome Found Hypolipidaemic compounds
DE4234867A1 (de) * 1992-10-16 1994-04-21 Degussa Verfahren zur Herstellung von Aminoalkylhydantoin und Aminoalkyl-alpha-aminosäuren
AU5533094A (en) 1992-11-27 1994-06-22 Wellcome Foundation Limited, The Enzyme inhibitors
JPH08504798A (ja) 1992-12-18 1996-05-21 ザ ウエルカム ファウンデーション リミテッド 酵素阻害薬としての，ピリミジン，ピリジン，プテリジノンおよびインダゾール誘導体
DE4324088A1 (de) * 1993-07-17 1995-01-19 Hoechst Ag Hochtemperatursupraleitende Massivkörper und Verfahren zu ihrer Herstellung
AU8078394A (en) 1993-10-21 1995-05-08 G.D. Searle & Co. Amidino derivatives useful as nitric oxide synthase inhibitors
CA2173468A1 (en) 1993-10-21 1995-04-27 Donald W. Hansen, Jr. Amidino derivatives useful as nitric oxide synthase inhibitors
GB9405211D0 (en) 1994-03-17 1994-04-27 Deas Alexander R Noise cancellation apparatus
DK0751930T3 (da) 1994-03-24 2000-04-17 Searle & Co Amidinoderivater anvendelige som nitrogenoxid-synthase-inhibitorer
EP0957087B1 (en) * 1994-06-15 2002-12-04 The Wellcome Foundation Limited Intermediates useful in the preparation of enzyme inhibitors
US5994391A (en) 1994-09-13 1999-11-30 G.D. Searle And Company Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
US5684008A (en) 1994-11-09 1997-11-04 G. D. Searle & Co. Aminotetrazole derivatives useful as nitric oxide synthase inhibitors
EP0821674B1 (en) 1995-04-20 2003-08-06 G.D. SEARLE & CO. Cyclic amidino agents useful as nitric oxide synthase inhibitors
CN1190390A (zh) 1995-05-10 1998-08-12 G.D.瑟尔公司 由环状脒衍生的氧化氮合成酶抑制剂
GB9516709D0 (en) 1995-08-15 1995-10-18 Zeneca Ltd Medicament
US5830917A (en) 1995-09-11 1998-11-03 G. D. Searle & Co. L-N6 -(1-iminoethyl) lysine derivatives useful as nitric oxide synthase inhibitors
US5981511A (en) 1996-03-06 1999-11-09 G.D. Searle & Co. Hydroxyamidino derivatives useful as nitric oxide synthase inhibitors
US5945408A (en) 1996-03-06 1999-08-31 G.D. Searle & Co. Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors
MY117948A (en) * 1997-01-13 2004-08-30 Glaxo Group Ltd Nitride oxide synthase inhibitors.
WO1999029865A2 (en) 1997-12-12 1999-06-17 The Rockefeller University A protein belonging to the tnf superfamily, nucleic acids encoding same, and methods of use thereof
SI1062201T1 (en) 1998-03-11 2005-10-31 G.D. Searle Llc Halogenated amidino amino acid derivatives useful as nitric oxide synthase inhibitors
GB9811599D0 (en) 1998-05-30 1998-07-29 Glaxo Group Ltd Nitric oxide synthase inhibitors
ZA200206459B (en) * 2000-03-24 2003-08-13 Pharmacia Corp Amidino compound and salts thereof useful as nitric oxide synthase inhibitors.

Also Published As

Publication number Publication date
WO2001072702A3 (en) 2002-09-19
ATE295832T1 (de) 2005-06-15
US20030199701A1 (en) 2003-10-23
HK1056161A1 (en) 2004-02-06
AU4774501A (en) 2001-10-08
AU2001249415B8 (en) 2001-10-08
US6586474B2 (en) 2003-07-01
US7102013B2 (en) 2006-09-05
MY135721A (en) 2008-06-30
WO2001072703A1 (en) 2001-10-04
BR0109386A (pt) 2003-04-15
NZ520813A (en) 2004-05-28
US20040186178A1 (en) 2004-09-23
US6403830B2 (en) 2002-06-11
ZA200206459B (en) 2003-08-13
JP4216502B2 (ja) 2009-01-28
DK1265860T3 (da) 2005-07-11
KR100835265B1 (ko) 2008-06-09
DE60110902T2 (de) 2006-04-27
NZ520812A (en) 2004-04-30
US20050165106A1 (en) 2005-07-28
US20020019563A1 (en) 2002-02-14
NZ532073A (en) 2005-12-23
DE60110902D1 (de) 2005-06-23
PT1265860E (pt) 2005-10-31
EP1265860A1 (en) 2002-12-18
ES2256223T3 (es) 2006-07-16
GEP20094625B (en) 2009-03-10
DE60116067T2 (de) 2006-08-31
MXPA02009282A (es) 2004-06-18
US7196118B2 (en) 2007-03-27
CN1294117C (zh) 2007-01-10
AU2001247745B2 (en) 2006-08-31
JP2003528852A (ja) 2003-09-30
ATE313525T1 (de) 2006-01-15
CA2402199A1 (en) 2001-10-04
EP1265860B1 (en) 2005-05-18
US20020111493A1 (en) 2002-08-15
AU4941501A (en) 2001-10-08
CA2402436C (en) 2010-02-16
KR20020091138A (ko) 2002-12-05
US6914158B2 (en) 2005-07-05
TWI294417B (en) 2008-03-11
AU2001249415B2 (en) 2007-01-04
EP1265859A2 (en) 2002-12-18
HK1050521A1 (en) 2003-06-27
ES2240445T3 (es) 2005-10-16
NZ542734A (en) 2007-06-29
EP1265859B1 (en) 2005-12-21
JP4205340B2 (ja) 2009-01-07
CA2402436A1 (en) 2001-10-04
DK1265859T3 (da) 2006-05-01
CN1419539A (zh) 2003-05-21
AR033359A1 (es) 2003-12-17
DE60116067D1 (de) 2006-01-26
WO2001072702A2 (en) 2001-10-04
JP2003528853A (ja) 2003-09-30
ZA200206455B (en) 2003-08-13

Similar Documents

Publication Publication Date Title
CA2402199C (en) Amidino compounds useful as nitric oxide synthase inhibitors
US6465686B2 (en) Halogenated 2-amino-5,6 heptenoic acid derivatives useful as nitric oxide synthase inhibitors
AU2001247745A1 (en) Amidino compounds useful as nitric oxide synthase inhibitors
AU2001249415A1 (en) Amidino compound and salts thereof useful as nitric oxide synthase inhibitors
WO2001079156A1 (en) Halogenated 2-amino-4, 5 heptenoic acid derivatives useful as nitric oxide synthase inhibitors
US6586471B1 (en) Halogenated 2-amino-3, 4 heptenoic acid derivatives useful as nitric oxide synthase inhibitors
HK1050521B (en) Amidino compounds useful as nitric oxide synthase inhibitors

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20190325