CA2436659C - Cannabinoid receptor ligands - Google Patents

Cannabinoid receptor ligands Download PDF

Info

Publication number
CA2436659C
CA2436659C CA2436659A CA2436659A CA2436659C CA 2436659 C CA2436659 C CA 2436659C CA 2436659 A CA2436659 A CA 2436659A CA 2436659 A CA2436659 A CA 2436659A CA 2436659 C CA2436659 C CA 2436659C
Authority
CA
Canada
Prior art keywords
compound
prodrug
pharmaceutically acceptable
soz
stereoisomer
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
CA2436659A
Other languages
English (en)
French (fr)
Other versions
CA2436659A1 (en
Inventor
Joseph A. Kozlowski
Neng-Yang Shih
Brian J. Lavey
Razia K. Rizvi
Bandarpalle B. Shankar
James M. Spitler
Ling Tong
Ronald Wolin
Michael K. Wong
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.)
Merck Sharp and Dohme LLC
Original Assignee
Schering Corp
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 Schering Corp filed Critical Schering Corp
Publication of CA2436659A1 publication Critical patent/CA2436659A1/en
Application granted granted Critical
Publication of CA2436659C publication Critical patent/CA2436659C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • 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
    • A61P11/16—Central respiratory analeptics
    • 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
    • A61P17/02—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
    • A61P19/08—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
    • 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
    • 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
    • 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
    • A61P31/04—Antibacterial 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/24—Tetrahydroxylic alcohols, e.g. pentaerythritol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom
    • 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
    • C07C323/64—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 sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/65—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 sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/36—Sulfur atoms
    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • 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
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/64—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Neurology (AREA)
  • Hematology (AREA)
  • Vascular Medicine (AREA)
  • Oncology (AREA)
  • Urology & Nephrology (AREA)
  • Transplantation (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Communicable Diseases (AREA)
  • Obesity (AREA)
  • Otolaryngology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Neurosurgery (AREA)
CA2436659A 2001-02-08 2002-02-07 Cannabinoid receptor ligands Expired - Fee Related CA2436659C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US26737501P 2001-02-08 2001-02-08
US60/267,375 2001-02-08
US29260001P 2001-05-22 2001-05-22
US60/292,600 2001-05-22
PCT/US2002/003672 WO2002062750A1 (en) 2001-02-08 2002-02-07 Cannabinoid receptor ligands

Publications (2)

Publication Number Publication Date
CA2436659A1 CA2436659A1 (en) 2002-08-15
CA2436659C true CA2436659C (en) 2010-07-27

Family

ID=26952402

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2436659A Expired - Fee Related CA2436659C (en) 2001-02-08 2002-02-07 Cannabinoid receptor ligands

Country Status (21)

Country Link
US (2) US7507767B2 (https=)
EP (1) EP1368308A1 (https=)
JP (2) JP4330341B2 (https=)
KR (1) KR20030075175A (https=)
CN (1) CN1285572C (https=)
AR (1) AR032569A1 (https=)
AU (1) AU2002306450B2 (https=)
BR (1) BR0206955A (https=)
CA (1) CA2436659C (https=)
CZ (1) CZ20032122A3 (https=)
HU (1) HUP0304060A3 (https=)
IL (1) IL156829A0 (https=)
MX (1) MXPA03007078A (https=)
NO (1) NO20033505L (https=)
NZ (1) NZ526782A (https=)
PE (1) PE20020851A1 (https=)
PL (1) PL364624A1 (https=)
RU (1) RU2003127368A (https=)
SK (1) SK9952003A3 (https=)
WO (1) WO2002062750A1 (https=)
ZA (1) ZA200305933B (https=)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7067539B2 (en) * 2001-02-08 2006-06-27 Schering Corporation Cannabinoid receptor ligands
US6897220B2 (en) * 2001-09-14 2005-05-24 Methylgene, Inc. Inhibitors of histone deacetylase
US7868204B2 (en) * 2001-09-14 2011-01-11 Methylgene Inc. Inhibitors of histone deacetylase
EP1429765A2 (en) * 2001-09-14 2004-06-23 Methylgene, Inc. Inhibitors of histone deacetylase
RU2004117907A (ru) 2001-11-14 2006-01-10 Шеринг Корпорейшн (US) Лиганды каннабиноидных рецепторов
WO2003061699A1 (en) * 2001-12-27 2003-07-31 Japan Tobacco, Inc. Remedies for allergic diseases
AU2003217961B2 (en) 2002-03-08 2008-02-28 Signal Pharmaceuticals, Llc Combination therapy for treating, preventing or managing proliferative disorders and cancers
MXPA04012704A (es) 2002-06-19 2005-03-23 Schering Corp Agonistas de los receptores canabinoides.
UY27939A1 (es) 2002-08-21 2004-03-31 Glaxo Group Ltd Compuestos
KR101025633B1 (ko) * 2002-09-19 2011-03-30 일라이 릴리 앤드 캄파니 오피오이드 수용체 안타고니스트로서의 디아릴 에테르
GB0222495D0 (en) * 2002-09-27 2002-11-06 Glaxo Group Ltd Compounds
GB0222493D0 (en) * 2002-09-27 2002-11-06 Glaxo Group Ltd Compounds
JP4690889B2 (ja) * 2002-10-24 2011-06-01 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング メチレン尿素誘導体
WO2004048322A1 (en) * 2002-11-25 2004-06-10 Schering Corporation Cannabinoid receptor ligands
EP1606019A1 (en) * 2003-03-07 2005-12-21 The University Court of The University of Aberdeen Cannabinoid receptor inverse agonists and neutral antagonists as therapeutic agents for the treatment of bone disorders
TW200505902A (en) 2003-03-20 2005-02-16 Schering Corp Cannabinoid receptor ligands
US6916852B2 (en) * 2003-05-12 2005-07-12 University Of Tennessee Research Foundation Method for regulation of microvascular tone
US7169942B2 (en) * 2003-05-20 2007-01-30 University Of Tennessee Research Foundation Cannabinoid derivatives, methods of making, and use thereof
KR101153335B1 (ko) * 2003-09-24 2012-07-05 메틸진 인코포레이티드 히스톤 데아세틸라제의 억제제
US7320805B2 (en) * 2003-10-01 2008-01-22 Institut National De La Sante Et De La Recherche Medicale CB2 receptors blocks accumulation of human hepatic myofibroblasts: a novel artifibrogenic pathway in the liver
WO2005044785A1 (en) * 2003-10-30 2005-05-19 Merck & Co., Inc. Aralkyl amines as cannabinoid receptor modulators
GB0402355D0 (en) * 2004-02-03 2004-03-10 Glaxo Group Ltd Novel compounds
GB0402357D0 (en) * 2004-02-03 2004-03-10 Glaxo Group Ltd Novel compounds
US7253204B2 (en) * 2004-03-26 2007-08-07 Methylgene Inc. Inhibitors of histone deacetylase
JP4646984B2 (ja) 2004-09-30 2011-03-09 メルク・シャープ・エンド・ドーム・コーポレイション シクロプロピルピペリジングリシン輸送体阻害剤
CA2632030A1 (en) 2005-12-15 2007-06-21 Boehringer Ingelheim International Gmbh Compounds which modulate the cb2 receptor
KR101495611B1 (ko) * 2006-04-07 2015-02-25 메틸진 인코포레이티드 히스톤 데아세틸라아제의 억제제
EP2081905B1 (en) 2006-07-28 2012-09-12 Boehringer Ingelheim International GmbH Sulfonyl compounds which modulate the cb2 receptor
KR20090051778A (ko) * 2006-09-08 2009-05-22 화이자 프로덕츠 인코포레이티드 다이아릴 에터 유도체 및 이의 용도
CA2664310A1 (en) 2006-09-25 2008-04-03 Boehringer Ingelheim International Gmbh Compounds which modulate the cb2 receptor
GB0702862D0 (en) * 2007-02-14 2007-03-28 Univ Aberdeen Therapeutic compounds
WO2010036630A2 (en) 2008-09-25 2010-04-01 Boehringer Ingelheim International Gmbh Compounds which selectively modulate the cb2 receptor
BRPI1011247A2 (pt) 2009-06-09 2016-06-21 California Capital Equity Llc derivados de isoquinolina, quinolina e quinazolina como inibidores de sinalização de hedgehog
WO2010144394A1 (en) 2009-06-09 2010-12-16 Abraxis Bioscience, Llc Benzyl substituted triazine derivatives and their therapeutical applications
KR101457027B1 (ko) 2009-06-09 2014-10-31 캘리포니아 캐피탈 에쿼티, 엘엘씨 트리아진 유도체와 이들의 치료적 용도
US9315454B2 (en) 2010-01-15 2016-04-19 Boehringer Ingelheim International Gmbh Compounds which modulate the CB2 receptor
JP5746764B2 (ja) 2010-07-22 2015-07-08 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ｃｂ２受容体を調節する化合物
US20120309820A1 (en) * 2011-06-04 2012-12-06 Jb Therapeutics Inc. Methods of treating fibrotic diseases using tetrahydrocannabinol-11-oic acids
TW201329025A (zh) 2011-11-01 2013-07-16 Astex Therapeutics Ltd 醫藥化合物
CA2859842C (en) 2012-03-14 2016-11-08 Sinochem Corporation Substitute diphenylamine compounds use thereof as antitumor agents
KR20190139327A (ko) 2013-02-12 2019-12-17 코버스 파마수티컬스, 아이엔씨. 초고순도 테트라하이드로카나비놀-11-오익산
TW201512171A (zh) 2013-04-19 2015-04-01 Pfizer Ltd 化學化合物
CN103265480B (zh) * 2013-05-11 2015-10-07 浙江大学 喹啉二酮类衍生物及其制备方法和用途
EP2803668A1 (en) 2013-05-17 2014-11-19 Boehringer Ingelheim International Gmbh Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles
US9636298B2 (en) 2014-01-17 2017-05-02 Methylgene Inc. Prodrugs of compounds that enhance antifungal activity and compositions of said prodrugs
US9763992B2 (en) 2014-02-13 2017-09-19 Father Flanagan's Boys' Home Treatment of noise induced hearing loss
KR102431436B1 (ko) 2014-08-29 2022-08-10 테스 파마 에스.알.엘. α-아미노-β-카복시뮤콘산 세미알데히드 데카복실라제의 억제제
CN108752375A (zh) * 2018-07-17 2018-11-06 成都睿智化学研究有限公司 一种4-溴甲基-2-三甲基硅乙炔基苯-1-磺酰氟的制备方法
US12257307B2 (en) 2019-06-24 2025-03-25 Diverse Biotech, Inc. β-lactam-cannabinoid conjugate molecules
CN112552200B (zh) * 2019-09-10 2024-03-12 烟台药物研究所 一种光学纯4-(1-氨基)乙基苯甲酸酯及其盐的制备方法

Family Cites Families (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3715375A (en) * 1970-09-17 1973-02-06 Merck & Co Inc New diphenyl sulfones
US3712888A (en) * 1970-12-14 1973-01-23 American Cyanamid Co Bis-pyridoxazole-stilbene derivatives for optical brightening
US4170648A (en) * 1972-05-26 1979-10-09 Rohm And Haas Company Phosphonothioureide anthelmintics
DE3039208A1 (de) 1980-10-17 1982-05-13 Basf Ag, 6700 Ludwigshafen Neue sulfone, deren herstellung und verwendung
DE3118126A1 (de) 1981-05-07 1982-12-02 Bayer Ag, 5090 Leverkusen Sulfenamide zur verwendung in arzneimitteln
US4618363A (en) 1982-01-25 1986-10-21 Ciba-Geigy Corporation N-phenylsulfonyl-N'-triazinylureas
US4468389A (en) * 1982-05-21 1984-08-28 Rohm And Haas Company Pesticidal N-sulfonyl phosphorodiamido(di)thioates
US4466965A (en) * 1982-07-26 1984-08-21 American Hospital Supply Corporation Phthalazine compounds, compositions and use
US4468965A (en) * 1982-11-05 1984-09-04 Union Carbide Corporation Test method for acetylene cylinders
US4567184A (en) * 1982-12-01 1986-01-28 Usv Pharmaceutical Corporation Certain aryl or hetero-aryl derivatives of 1-hydroxy-pentane or 1-hydroxy-hexane which are useful for treating inflammation and allergies
NO174506B (no) 1984-10-30 1994-02-07 Usv Pharma Corp Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser
US4764889A (en) 1984-12-19 1988-08-16 American Telephone And Telegraph Company, At&T Bell Laboratories Optical logic arrangement with self electro-optic effect devices
US4781866A (en) * 1985-03-15 1988-11-01 Mcneilab, Inc. Process for producing amidine sulfonic acid intermediates for guanidines
US4678855A (en) 1985-10-09 1987-07-07 Merck & Co., Inc. Substituted benzenesulfonamides
SK278455B6 (en) 1986-03-31 1997-06-04 Rhone Poulenc Bv Agent for growth regulation of plants
HU201448B (en) 1986-03-31 1990-11-28 Rhone Poulenc Bv Plant growth reducing compositions comprising malonic acid derivatives and process for producing new malonic acid derivatives
DE3634926A1 (de) 1986-10-14 1988-04-21 Bayer Ag Verfahren zur herstellung von o-aryl-n'-pyrimidin-2-yl-isoharnstoffen
DE3634927A1 (de) 1986-10-14 1988-04-21 Bayer Ag Verfahren zur herstellung von sulfonylisothioharnstoffen
US4851423A (en) 1986-12-10 1989-07-25 Schering Corporation Pharmaceutically active compounds
CA1293516C (en) 1987-02-10 1991-12-24 Izumi Fujimoto Benzoylurea derivative and its production and use
NZ232493A (en) 1989-02-14 1992-06-25 Toyama Chemical Co Ltd Aryl- or heterocyclyl-substituted 1,2-ethanediol derivatives and pharmaceutical compositions
US5064825A (en) 1989-06-01 1991-11-12 Merck & Co., Inc. Angiotensin ii antagonists
IE902465A1 (en) 1989-07-07 1991-02-13 Schering Corp Pharmaceutically active compounds
IT1240676B (it) 1990-04-24 1993-12-17 Agrimont Spa Composizioni ad attivita' erbicida
NZ239846A (en) 1990-09-27 1994-11-25 Merck & Co Inc Sulphonamide derivatives and pharmaceutical compositions thereof
US5332820A (en) * 1991-05-20 1994-07-26 E. I. Du Pont De Nemours And Company Dibenzobicyclo(2.2.2) octane angiotensin II antagonists
WO1993000313A2 (en) 1991-06-27 1993-01-07 Virginia Commonwealth University Sigma receptor ligands and the use thereof
US5506227A (en) 1992-04-13 1996-04-09 Merck Frosst Canada, Inc. Pyridine-substituted benzyl alcohols as leukotriene antagonists
US5338753A (en) * 1992-07-14 1994-08-16 Sumner H. Burstein (3R,4R)-Δ6 -tetrahydrocannabinol-7-oic acids useful as antiinflammatory agents and analgesics
GB9218834D0 (en) 1992-09-05 1992-10-21 Procter & Gamble Nasal spray products
WO1995000491A1 (en) 1993-06-17 1995-01-05 Dunlena Pty Ltd. Arthropodicidal sulfonates
US5486525A (en) * 1993-12-16 1996-01-23 Abbott Laboratories Platelet activating factor antagonists: imidazopyridine indoles
FR2714057B1 (fr) * 1993-12-17 1996-03-08 Sanofi Elf Nouveaux dérivés du 3-pyrazolecarboxamide, procédé pour leur préparation et compositions pharmaceutiques les contenant.
WO1995027693A1 (en) 1994-04-06 1995-10-19 Shionogi & Co., Ltd. α-SUBSTITUTED PHENYLACETIC ACID DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND AGRICULTURAL BACTERICIDE CONTAINING THE SAME
IT1271266B (it) * 1994-12-14 1997-05-27 Valle Francesco Della Impiego terapeutico di ammidi di acidi mono e bicarbossilici con amminoalcoli,selettivamente attive sul recettore periferico dei cannabinoidi
RO115522B1 (ro) 1995-02-02 2000-03-30 Smithkline Beecham P.L.C. Derivaţi de indolină, procedee pentru prepararea acestora, compoziţii farmaceutice care îi conţin şi metodă de tratament
US5532237A (en) * 1995-02-15 1996-07-02 Merck Frosst Canada, Inc. Indole derivatives with affinity for the cannabinoid receptor
US5700816A (en) 1995-06-12 1997-12-23 Isakson; Peter C. Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor
FR2735774B1 (fr) * 1995-06-21 1997-09-12 Sanofi Sa Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant
DE59605948D1 (de) 1995-07-21 2000-11-02 Nycomed Austria Gmbh Linz Derivate von benzosulfonamiden als hemmer des enzym cyclooxygenase ii
DE19533644A1 (de) 1995-09-12 1997-03-13 Nycomed Arzneimittel Gmbh Neue Benzolsulfonamide
FR2742148B1 (fr) * 1995-12-08 1999-10-22 Sanofi Sa Nouveaux derives du pyrazole-3-carboxamide, procede pour leur preparation et compositions pharmaceutiques les contenant
EP0887340A4 (en) * 1996-02-06 2000-03-29 Japan Tobacco Inc CHEMICAL COMPOUNDS AND THEIR PHARMACEUTICAL USE
SE9602646D0 (sv) 1996-07-04 1996-07-04 Astra Ab Pharmaceutically-useful compounds
CA2264037A1 (en) 1996-09-13 1998-03-19 Merck & Co., Inc. Thrombin inhibitors
JP3426890B2 (ja) 1996-12-25 2003-07-14 アルプス電気株式会社 入力ペン
DE69822449T2 (de) 1997-01-21 2005-01-27 Smithkline Beecham Corp. Neue cannabinoidrezeptor-modulatoren
ATA16597A (de) 1997-02-03 1998-04-15 Nycomed Austria Gmbh Neue substituierte p-sulfonylaminobenzol- sulfonsäureamide
TR199902012T2 (xx) 1997-02-21 2000-01-21 Bayer Aktiengesellschaft Arils�lfonamidler ve analoglar�
DE19740785A1 (de) 1997-02-21 1998-08-27 Bayer Ag Arylsulfonamide und Analoga
EP0979228A4 (en) 1997-03-18 2000-05-03 Smithkline Beecham Corp CANNABINOID RECEPTOR AGONISTS
DE69842143D1 (de) 1997-10-24 2011-04-07 Nissan Chemical Ind Ltd Sulfamoyl-verbindungen und bakterizide für landwirtschaft oder gartenbau
WO1999026612A1 (en) 1997-11-21 1999-06-03 Smithkline Beecham Corporation Novel cannabinoid receptor modulators
PL343249A1 (en) 1998-03-26 2001-07-30 Shionogi & Co Indole derivatives with antiviral activity
BR9912406A (pt) 1998-07-28 2001-04-24 Smithkline Beecham Corp Compostos de anilida substituida e métodos
JP2000143650A (ja) 1998-11-13 2000-05-26 Takeda Chem Ind Ltd 新規チアゾリジン誘導体、その製造法および用途
WO2000056707A1 (en) 1999-03-24 2000-09-28 Sepracor, Inc. Diaryl thioethers, compositions and uses thereof
JP4618845B2 (ja) 1999-06-09 2011-01-26 杏林製薬株式会社 ヒトペルオキシゾーム増殖薬活性化受容体（ＰＰＡＲ）αアゴニストとしての置換フェニルプロピオン酸誘導体
WO2001014351A1 (en) * 1999-08-23 2001-03-01 Kyorin Pharmaceutical Co., Ltd. Substituted benzylthiazolidine-2,4-dione derivatives
US6818640B1 (en) 1999-09-14 2004-11-16 Shionogi & Co., Ltd. 2-imino-1,3-thiazine derivatives
DE60030303T2 (de) 1999-10-18 2007-10-11 The University Of Connecticut, Farmington Cannabimimetische indolderivate
CA2389681C (en) 1999-11-26 2010-11-02 Shionogi & Co., Ltd. Npy y5 antagonist
DE60030764T2 (de) 1999-12-15 2007-09-13 Bristol-Myers Squibb Co. Biphenyl - sulfonamide als duale angiotensin - endothelin - rezeptor - antagonisten
AU2108601A (en) 1999-12-15 2001-06-25 Axys Pharmaceuticals, Inc. Salicylamides as serine protease inhibitors
EP1257157B1 (en) 1999-12-31 2004-11-24 Lear Automotive (EEDS) Spain, S.L. Method for manufacturing printed circuit boards
AU2001250783A1 (en) 2000-02-29 2001-09-12 Cor Therapeutics, Inc. Benzamides and related inhibitors of factor xa
JP2003528106A (ja) 2000-03-22 2003-09-24 メルク フロスト カナダ アンド カンパニー Ｐｔｐ−１ｂ阻害薬としての硫黄置換アリールジフルオロメチルホスホン酸類
US7132567B2 (en) 2000-04-03 2006-11-07 Cerno Biosciences, Llc Generation of combinatorial synthetic libraries and screening for proadhesins and nonadhesins
CN1251671C (zh) 2000-05-19 2006-04-19 武田药品工业株式会社 β分泌酶抑制剂
GB0028702D0 (en) 2000-11-24 2001-01-10 Novartis Ag Organic compounds
US7067539B2 (en) * 2001-02-08 2006-06-27 Schering Corporation Cannabinoid receptor ligands
RU2004117907A (ru) 2001-11-14 2006-01-10 Шеринг Корпорейшн (US) Лиганды каннабиноидных рецепторов

Also Published As

Publication number Publication date
CZ20032122A3 (cs) 2003-10-15
KR20030075175A (ko) 2003-09-22
CN1489576A (zh) 2004-04-14
EP1368308A1 (en) 2003-12-10
JP2009024011A (ja) 2009-02-05
SK9952003A3 (en) 2004-01-08
US20060009528A1 (en) 2006-01-12
CN1285572C (zh) 2006-11-22
HUP0304060A3 (en) 2005-05-30
CA2436659A1 (en) 2002-08-15
AR032569A1 (es) 2003-11-12
RU2003127368A (ru) 2005-03-27
US20030096844A1 (en) 2003-05-22
JP2004530649A (ja) 2004-10-07
BR0206955A (pt) 2004-03-09
JP4330341B2 (ja) 2009-09-16
US7718702B2 (en) 2010-05-18
NO20033505D0 (no) 2003-08-07
MXPA03007078A (es) 2003-11-18
NO20033505L (no) 2003-10-07
NZ526782A (en) 2005-05-27
US7507767B2 (en) 2009-03-24
PE20020851A1 (es) 2002-12-04
WO2002062750A9 (en) 2003-09-18
HUP0304060A2 (hu) 2004-04-28
ZA200305933B (en) 2005-01-26
WO2002062750A1 (en) 2002-08-15
PL364624A1 (en) 2004-12-13
IL156829A0 (en) 2004-02-08
AU2002306450B2 (en) 2005-09-22

Similar Documents

Publication Publication Date Title
CA2436659C (en) Cannabinoid receptor ligands
CA2494827A1 (en) Cannabinoid receptor ligands
AU2002306450A1 (en) Cannabinoid receptor ligands
US7439242B2 (en) PPARγ modulators
TWI409247B (zh) ４-取代之苯氧基苯基乙酸衍生物
CA2487346A1 (en) Cannabinoid receptor agonists
EP1565431B1 (en) Cannabinoid receptor ligands
HK1074040B (en) Cannabinoid receptor ligands

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed