DE60312016T2 - Cyclohexylsulfon-derivate als gamma-secretase-inhibitoren - Google Patents

Cyclohexylsulfon-derivate als gamma-secretase-inhibitoren Download PDF

Info

Publication number
DE60312016T2
DE60312016T2 DE60312016T DE60312016T DE60312016T2 DE 60312016 T2 DE60312016 T2 DE 60312016T2 DE 60312016 T DE60312016 T DE 60312016T DE 60312016 T DE60312016 T DE 60312016T DE 60312016 T2 DE60312016 T2 DE 60312016T2
Authority
DE
Germany
Prior art keywords
alkyl
sup
sub
cor
nhcor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
DE60312016T
Other languages
German (de)
English (en)
Other versions
DE60312016D1 (en
Inventor
Ian Harlow CHURCHER
Timothy Harlow HARRISON
Sonia Harlow KERRAD
Paul Joseph Harlow OAKLEY
Duncan Edward Harlow SHAW
Martin Richard Harlow TEALL
Susannah Harlow WILLIAMS
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.)
Organon Pharma UK Ltd
Original Assignee
Merck Sharp and Dohme Ltd
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 Merck Sharp and Dohme Ltd filed Critical Merck Sharp and Dohme Ltd
Publication of DE60312016D1 publication Critical patent/DE60312016D1/de
Application granted granted Critical
Publication of DE60312016T2 publication Critical patent/DE60312016T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/70Sulfur atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/14Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/16Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/16Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/20Sulfones; 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 rings other than six-membered aromatic rings of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/16Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22Sulfones; 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/24Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02Thiocyanates
    • C07C331/04Thiocyanates having sulfur atoms of thiocyanate groups bound to acyclic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D205/00Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/48Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/96Sulfur atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/70Sulfur atoms
    • C07D213/71Sulfur atoms to which a second hetero atom is attached
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/89Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic 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
    • C07D233/66Heterocyclic 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
    • C07D233/84Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/38One sulfur atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/101,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12Oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D257/00Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04Five-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic 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
    • C07D277/32Heterocyclic 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
    • C07D277/36Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01Five-membered rings
    • C07D285/02Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/121,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/1251,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/38Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/38Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40Radicals substituted by oxygen atoms
    • C07D307/46Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/38Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/56Heterocyclic 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
    • C07D307/64Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/56Heterocyclic 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
    • C07D307/68Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic 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
    • C07D333/06Heterocyclic 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
    • C07D333/14Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C07D333/48Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08Bridged systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/02Systems containing only non-condensed rings with a three-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/04Systems containing only non-condensed rings with a four-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Neurology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyridine Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyrrole Compounds (AREA)
DE60312016T 2002-10-04 2003-09-25 Cyclohexylsulfon-derivate als gamma-secretase-inhibitoren Expired - Lifetime DE60312016T2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0223039 2002-10-04
GBGB0223039.9A GB0223039D0 (en) 2002-10-04 2002-10-04 Therapeutic compounds
PCT/GB2003/004102 WO2004031137A1 (en) 2002-10-04 2003-09-25 Cyclohexyl sulphone derivatives as gamma-secretase inhibitors

Publications (2)

Publication Number Publication Date
DE60312016D1 DE60312016D1 (en) 2007-04-05
DE60312016T2 true DE60312016T2 (de) 2007-10-31

Family

ID=9945313

Family Applications (1)

Application Number Title Priority Date Filing Date
DE60312016T Expired - Lifetime DE60312016T2 (de) 2002-10-04 2003-09-25 Cyclohexylsulfon-derivate als gamma-secretase-inhibitoren

Country Status (10)

Country Link
US (1) US7101895B2 (https=)
EP (1) EP1551797B1 (https=)
JP (1) JP4653485B2 (https=)
AT (1) ATE354562T1 (https=)
AU (1) AU2003267614B2 (https=)
CA (1) CA2500964C (https=)
DE (1) DE60312016T2 (https=)
ES (1) ES2280774T3 (https=)
GB (1) GB0223039D0 (https=)
WO (1) WO2004031137A1 (https=)

Families Citing this family (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0108591D0 (en) * 2001-04-05 2001-05-23 Merck Sharp & Dohme Therapeutic agents
GB0120347D0 (en) 2001-08-21 2001-10-17 Merck Sharp & Dohme Therapeutic agents
CN100562516C (zh) 2001-12-27 2009-11-25 第一制药株式会社 β-淀粉样蛋白产生和分泌的抑制剂
US7521481B2 (en) 2003-02-27 2009-04-21 Mclaurin Joanne Methods of preventing, treating and diagnosing disorders of protein aggregation
CA2526487A1 (en) 2003-06-30 2005-01-06 Daiichi Pharmaceutical Co., Ltd. Heterocyclic methyl sulfone derivative
AR047666A1 (es) * 2004-02-20 2006-02-01 Merck Sharp & Dohme Sintesis estereoselectiva del acido ciclohexanopropanoico 4,4-disubstituido
US20090215775A1 (en) * 2005-05-17 2009-08-27 Huw David Lewis Sulphonamido-Substituted Cyclohexyl Sulphones for Treatment of Cancer
WO2006123182A2 (en) 2005-05-17 2006-11-23 Merck Sharp & Dohme Limited Cyclohexyl sulphones for treatment of cancer
PE20061490A1 (es) * 2005-06-06 2007-02-09 Merck Sharp & Dohme Derivados de ciclohexanosulfonilo como inhibidores del transportador de glicina glyt1
GB0513747D0 (en) * 2005-07-06 2005-08-10 Merck Sharp & Dohme Therapeutic compounds
KR20080095885A (ko) * 2006-01-20 2008-10-29 쉐링 코포레이션 벤젠설포닐-크로만, 티오크로만, 테트라하이드로나프탈렌 및 관련된 감마 세크라타제 억제제
EP2089383B1 (en) 2006-11-09 2015-09-16 Probiodrug AG 3-hydr0xy-1,5-dihydr0-pyrr0l-2-one derivatives as inhibitors of glutaminyl cyclase for the treatment of ulcer, cancer and other diseases
EP2094836B1 (en) 2006-11-15 2016-06-08 Massachusetts Eye & Ear Infirmary Generation of inner ear cells
US9126987B2 (en) 2006-11-30 2015-09-08 Probiodrug Ag Inhibitors of glutaminyl cyclase
CA2676715A1 (en) 2007-02-12 2008-08-21 Merck & Co., Inc. Piperazine derivatives for treatment of ad and related conditions
AU2008220785B2 (en) 2007-03-01 2013-02-21 Vivoryon Therapeutics N.V. New use of glutaminyl cyclase inhibitors
JP5667440B2 (ja) 2007-04-18 2015-02-12 プロビオドルグ エージー グルタミニルシクラーゼ阻害剤としてのチオ尿素誘導体
WO2009008980A2 (en) 2007-07-05 2009-01-15 Schering Corporation Tetrahydropyranochromene gamma secretase inhibitors
US8618123B2 (en) * 2007-07-17 2013-12-31 Merck Sharp & Dohme Corp. Benzenesulfonyl-chromane, thiochromane, tetrahydronaphthalene and related gamma secretase inhibitors
US8377886B2 (en) * 2007-09-14 2013-02-19 Albert Einstein College Of Medicine Of Yeshiva University Use of gamma secretase inhibitors and notch pathway inhibitors for treatment and prevention of renal disease
WO2009128057A2 (en) 2008-04-18 2009-10-22 UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN et al Psycho-pharmaceuticals
WO2010060088A2 (en) 2008-11-24 2010-05-27 Massachusetts Eye & Ear Infirmary Pathways to generate hair cells
US8609897B2 (en) * 2009-02-06 2013-12-17 Merck Sharp & Dohme Corp. Trifluoromethylsulfonamide gamma secretase inhibitor
WO2010114780A1 (en) 2009-04-01 2010-10-07 Merck Sharp & Dohme Corp. Inhibitors of akt activity
JP5934645B2 (ja) 2009-09-11 2016-06-15 プロビオドルグ エージー グルタミニルシクラーゼ阻害剤としてのヘテロ環式誘導体
US8859776B2 (en) 2009-10-14 2014-10-14 Merck Sharp & Dohme Corp. Substituted piperidines that increase p53 activity and the uses thereof
WO2011107530A2 (en) 2010-03-03 2011-09-09 Probiodrug Ag Novel inhibitors
JP5688745B2 (ja) 2010-03-10 2015-03-25 プロビオドルグ エージー グルタミニルシクラーゼ(qc、ec2.3.2.5)の複素環阻害剤
WO2011131748A2 (en) 2010-04-21 2011-10-27 Probiodrug Ag Novel inhibitors
US8999957B2 (en) 2010-06-24 2015-04-07 Merck Sharp & Dohme Corp. Heterocyclic compounds as ERK inhibitors
CA2805265A1 (en) 2010-08-02 2012-02-09 Merck Sharp & Dohme Corp. Rna interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (ctnnb1) gene expression using short interfering nucleic acid (sina)
WO2012024170A2 (en) 2010-08-17 2012-02-23 Merck Sharp & Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF HEPATITIS B VIRUS (HBV) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA)
WO2012030685A2 (en) 2010-09-01 2012-03-08 Schering Corporation Indazole derivatives useful as erk inhibitors
US9242981B2 (en) 2010-09-16 2016-01-26 Merck Sharp & Dohme Corp. Fused pyrazole derivatives as novel ERK inhibitors
WO2012058210A1 (en) 2010-10-29 2012-05-03 Merck Sharp & Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACIDS (siNA)
EP2654748B1 (en) 2010-12-21 2016-07-27 Merck Sharp & Dohme Corp. Indazole derivatives useful as erk inhibitors
EP2686313B1 (en) 2011-03-16 2016-02-03 Probiodrug AG Benzimidazole derivatives as inhibitors of glutaminyl cyclase
EP2770987B1 (en) 2011-10-27 2018-04-04 Merck Sharp & Dohme Corp. Novel compounds that are erk inhibitors
WO2013165816A2 (en) 2012-05-02 2013-11-07 Merck Sharp & Dohme Corp. SHORT INTERFERING NUCLEIC ACID (siNA) COMPOSITIONS
CA2883896C (en) 2012-09-07 2023-03-07 Massachusetts Eye & Ear Infirmary Treating hearing loss
CA2884309A1 (en) 2012-09-07 2014-03-13 Massachusetts Eye And Ear Infirmary Methods and compositions for regenerating hair cells and/or supporting cells from differentiated cochlear cells or differentiated utricular cells by modulation of notch and cmyc activity
WO2014052563A2 (en) 2012-09-28 2014-04-03 Merck Sharp & Dohme Corp. Novel compounds that are erk inhibitors
ME02925B (me) 2012-11-28 2018-04-20 Merck Sharp & Dohme Kompozicije i postupci za liječenje kancera
TW201429969A (zh) 2012-12-20 2014-08-01 Merck Sharp & Dohme 作爲hdm2抑制劑之經取代咪唑吡啶
WO2014120748A1 (en) 2013-01-30 2014-08-07 Merck Sharp & Dohme Corp. 2,6,7,8 substituted purines as hdm2 inhibitors
US8859286B2 (en) 2013-03-14 2014-10-14 Viacyte, Inc. In vitro differentiation of pluripotent stem cells to pancreatic endoderm cells (PEC) and endocrine cells
US20160194368A1 (en) 2013-09-03 2016-07-07 Moderna Therapeutics, Inc. Circular polynucleotides
CN106061947B (zh) * 2014-01-06 2019-12-03 百时美施贵宝公司 环己基砜RORγ调节剂
CA2952315A1 (en) 2014-07-11 2016-01-14 Genentech, Inc. Notch pathway inhibition
WO2016022776A2 (en) 2014-08-06 2016-02-11 Massachusetts Eye And Ear Infirmary Increasing atoh1 life to drive sensorineural hair cell differentiantion
AU2016297793A1 (en) 2015-07-24 2018-02-08 Oncotracker, Inc. Gamma secretase modulators for the treatment of immune system dysfunction
WO2017096233A1 (en) 2015-12-04 2017-06-08 Massachusetts Eye And Ear Infirmary Treatment of hearing loss by inhibition of casein kinase 1
CN109219439B (zh) 2016-01-29 2022-09-20 马萨诸塞眼科耳科诊所 内耳支持细胞的扩增和分化及其使用方法
JP6840774B2 (ja) 2016-05-16 2021-03-10 ザ ジェネラル ホスピタル コーポレイション 肺上皮エンジニアリングにおけるヒト気道幹細胞
US10975084B2 (en) 2016-10-12 2021-04-13 Merck Sharp & Dohme Corp. KDM5 inhibitors
MX390370B (es) 2016-12-16 2025-03-20 Pipeline Therapeutics Inc Metodos para tratar la sinaptopatia coclear
IL268349B2 (en) 2017-02-17 2024-08-01 Hutchinson Fred Cancer Res Combination therapies for treatment of bcma-related cancers and autoimmune disorders
ES2812698T3 (es) 2017-09-29 2021-03-18 Probiodrug Ag Inhibidores de glutaminil ciclasa
EP3706747B1 (en) 2017-11-08 2025-09-03 Merck Sharp & Dohme LLC Prmt5 inhibitors
US10947234B2 (en) 2017-11-08 2021-03-16 Merck Sharp & Dohme Corp. PRMT5 inhibitors
WO2020033288A1 (en) 2018-08-07 2020-02-13 Merck Sharp & Dohme Corp. Prmt5 inhibitors
EP3833669A4 (en) 2018-08-07 2022-05-11 Merck Sharp & Dohme Corp. PRMT5 INHIBITORS
WO2020033282A1 (en) 2018-08-07 2020-02-13 Merck Sharp & Dohme Corp. Prmt5 inhibitors
US11981701B2 (en) 2018-08-07 2024-05-14 Merck Sharp & Dohme Llc PRMT5 inhibitors
JP7589247B2 (ja) 2019-12-17 2024-11-25 メルク・シャープ・アンド・ドーム・エルエルシー Prmt5阻害剤
CN115003303B (zh) 2019-12-17 2024-03-08 默沙东公司 Prmt5抑制剂
EP4076460B1 (en) 2019-12-17 2026-01-21 Merck Sharp & Dohme LLC 1,4-dihydro-2h-spiro[isoquinoline-3,4'-piperidine derivatives as prmt5 inhibitors for the treatment of cancer
US12595248B2 (en) 2019-12-17 2026-04-07 Merck Sharp & Dohme Llc PRMT5 inhibitors
CN111205264A (zh) * 2020-02-25 2020-05-29 成都睿智化学研究有限公司 一种合成同位羟基和甲磺酰甲基化合物的新方法
BR112022018987A2 (pt) 2020-03-26 2022-11-01 Seagen Inc Métodos de tratamento de mieloma múltiplo
JP2025511436A (ja) 2022-09-02 2025-04-16 メルク・シャープ・アンド・ドーム・エルエルシー エキサテカン由来トポイソメラーゼ-1阻害薬医薬組成物及びその使用
CN120417935A (zh) 2022-10-25 2025-08-01 默沙东有限责任公司 依喜替康衍生的adc接头-载荷及其药物组合物和用途
US20240207425A1 (en) 2022-12-14 2024-06-27 Merck Sharp & Dohme Llc Auristatin linker-payloads, pharmaceutical compositions, and uses thereof

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2802013A (en) * 1954-02-12 1957-08-06 Searle & Co 2-(oxo and imino)-3-(phenyl and halophenyl)-tetrahydrofuransulfones and processes for the manufacture thereof
US2812330A (en) * 1956-05-02 1957-11-05 Searle & Co Sulfone derivatives of 2, 6-piperidinedione
JPS5625149A (en) 1979-08-08 1981-03-10 Sagami Chem Res Center Keto ester derivative and its preparation
JPS5626866A (en) 1979-08-13 1981-03-16 Sagami Chem Res Center Unsaturated ketoester derivative and its preparation
JPS5626847A (en) 1979-08-13 1981-03-16 Sagami Chem Res Center Preparation of substituted salicylic acid derivative
CA2191924A1 (en) * 1995-12-05 1997-06-06 Kevin Felsenstein 5-amino-6-cyclohexyl-4-hydroxy-hexanamide derivatives as inhibitors of .beta.-amyloid protein production
EP0863134A1 (en) 1997-03-07 1998-09-09 Merck Frosst Canada Inc. 2-(3,5-difluorophenyl)-3-(4-(methyl-sulfonyl)phenyl)-2-cyclopenten-1-one useful as an inhibitor of cyclooxygenase-2
HRP990246A2 (en) * 1998-08-07 2000-06-30 Du Pont Pharm Co Succinoylamino benzodiazepines as inhibitors of a beta protein production
WO2000050391A1 (en) 1999-02-26 2000-08-31 Merck & Co., Inc. Novel sulfonamide compounds and uses thereof
WO2001070677A1 (en) * 2000-03-20 2001-09-27 Merck Sharp & Dohme Limited Sulphonamido-substituted bridged bicycloalkyl derivatives
GB0108592D0 (en) 2001-04-05 2001-05-23 Merck Sharp & Dohme Therapeutic agents
GB0108591D0 (en) * 2001-04-05 2001-05-23 Merck Sharp & Dohme Therapeutic agents
JP2005504042A (ja) * 2001-08-03 2005-02-10 シェーリング コーポレイション γセクレターゼインヒビターのようなスルホンアミド誘導体
HUP0401241A3 (en) 2001-08-21 2008-03-28 Merck Sharp & Dohme Novel cyclohexyl sulphones, process for their preparation and pharmaceutical compositions containing them
CN100562516C (zh) 2001-12-27 2009-11-25 第一制药株式会社 β-淀粉样蛋白产生和分泌的抑制剂
DE10201392A1 (de) 2002-01-16 2003-07-31 Bayer Ag Phenylsulfoxide und-sulfone
GB0218041D0 (en) 2002-08-02 2002-09-11 Merck Sharp & Dohme Chemical process
JP3092689U (ja) * 2002-09-10 2003-03-20 船井電機株式会社 光ピックアップ
GB0223040D0 (en) 2002-10-04 2002-11-13 Merck Sharp & Dohme Therapeutic compounds
GB0223038D0 (en) * 2002-10-04 2002-11-13 Merck Sharp & Dohme Therapeutic compounds
DE10254875A1 (de) 2002-11-25 2004-06-03 Bayer Healthcare Ag Phenylsulfoxid und -sulfon-Derivate
GB0304524D0 (en) * 2003-02-27 2003-04-02 Merck Sharp & Dohme Therapeutic agents
EP1638951B1 (en) 2003-05-16 2008-02-13 MERCK SHARP & DOHME LTD. Cyclohexyl sulphones as gamma-secretase inhibitors
CA2526487A1 (en) 2003-06-30 2005-01-06 Daiichi Pharmaceutical Co., Ltd. Heterocyclic methyl sulfone derivative
GB0323258D0 (en) * 2003-10-04 2003-11-05 Merck Sharp & Dohme Therapeutic compounds

Also Published As

Publication number Publication date
JP2006501292A (ja) 2006-01-12
AU2003267614B2 (en) 2010-02-18
ATE354562T1 (de) 2007-03-15
GB0223039D0 (en) 2002-11-13
EP1551797B1 (en) 2007-02-21
DE60312016D1 (en) 2007-04-05
US20040122050A1 (en) 2004-06-24
WO2004031137A1 (en) 2004-04-15
AU2003267614A1 (en) 2004-04-23
JP4653485B2 (ja) 2011-03-16
CA2500964A1 (en) 2004-04-15
EP1551797A1 (en) 2005-07-13
CA2500964C (en) 2011-01-18
US7101895B2 (en) 2006-09-05
ES2280774T3 (es) 2007-09-16

Similar Documents

Publication Publication Date Title
DE60312016T2 (de) Cyclohexylsulfon-derivate als gamma-secretase-inhibitoren
AU2003269211C1 (en) Cyclohexyl sulphones as gamma-secretase inhibitors
DE60312017T2 (de) Sulfonderivate zur hemmung von gamma-secretase
DE69512797T2 (de) Prostaglandin-synthase hemmer
DE60319714T2 (de) Agonisten des cannabinoidrezeptors
DE602004007808T2 (de) Neue gamma-sekretase-inhibitoren
DE69920009T2 (de) Isothiazole derivate verwendbar als antikrebsmittel
DE69431517T2 (de) Hypolipemische verbindungen
DE69719538T2 (de) Thiol-sulfonen als metalloproteinaseinhibitoren
DE60129210T2 (de) Zyklische amid-derivate
DE69732571T2 (de) Beta-sulfonyl-hydroxamsäuren als matrix-metalloproteinaseinhibitoren
RU2304140C2 (ru) ИНГИБИТОРЫ ПРОДУЦИРОВАНИЯ / СЕКРЕЦИИ β-АМИЛОИДНОГО БЕЛКА
US7655675B2 (en) Gamma-secretase inhibitors
EP0414019B1 (de) Substituierte N-(Chinolin-2-yl-methoxy)benzylsulfonylharnstoffe
DE3877709T2 (de) Indan-derivate und verfahren zu deren herstellung.
DE69612037T2 (de) Thiopyran Derivate
DE69618050T2 (de) Substituierte Benzylthienylpiperazine, ihre Anwendung als Arzneimittel und Verfahren für ihre Herstellung
DE69810800T2 (de) Azetidinonderivate zur behandlung von hcmv entzündungen
DE68924221T2 (de) Imidazolderivate.
DE60010855T2 (de) Phenylsulphonylderivative als 5-ht rezeptorliganden
DE2553622A1 (de) Verfahren zur herstellung substituierter n-phenylcarbamatester
DE3889497T2 (de) 3,4-Dihydro-2-alkyl-3-oxo-N-aryl-2H-[1]benzothieno[3,2-e]-1,2-thiazine-4-carboxamid-1,1-dioxide.
DE2556045A1 (de) Verfahren zur herstellung von 3-methylencephamsulfoxiden
EP0156091A1 (de) Beta-Oxo-alpha-carbamoyl-pyrrolpropionitrile, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung

Legal Events

Date Code Title Description
8364 No opposition during term of opposition