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US 7,842,695 B2Granted
Substituted pyrazole compounds
AssigneeMerck Patent GmbH
InventorsOliver Schadt, Michael Arlt, Dirk Finsinger, Kai Schiemann, Christoph Van Amsterdam, Gerd Bartoszyk, Christoph Seyfried
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I) and salts thereof, in which the following definitions apply: X is N or CH; R1 is H, A, Hal, (CH2)nHet, (CH2)nAr, C3-7-cycloalkyl, CF3, NO2, CN, C(NH)(OH), or OCF3; R2 is (CH2)nHet, (CH2)nAr, or C3-7-cycloalkyl, or CF3; R3 and R4 denote H or an organic radical. Compounds of formula (I) are useful as ligands of 5-HT receptors and useful in the treatment of disorders such as anxiety, depression, obsessive-compulsive disorder and pain.
Claims23
A compound of formula I
- in which
- R1 denotes (CH2)nHet1, or (CH2)nAr,
- Het1 is 4-pyridyl, thiophen-2-yl or thiophen-3-yl, which is unsubstituted or mono- or polysubstituted by CN, A and/or Hal,
- R2 denotes Het2
- Het2 is 2- or 3-furanyl, which is unsubstituted or mono- or polysubstituted by A and/or Hal,
- R3, R4 one of the radicals R3 or R4 denotes H, and the other of the radicals R3 or R4 denotes (CH2)nCO2R5, (CH2)nCOHet3, CHO, (CH2)nOR5, (CH2)nHet3, (CH2)nN(R5)2, CH═N—OA, CH2CH═N—OA, (CH2)nNHOA, (CH2)nN(R5)Het3, (CH2)nCH═N-Het3, (CH2)nOCOR5, (CH2)nN(R5)CH2CH2OR5, (CH2)nN(R5)CH2CH2OCF3, (CH2)nN(R5)C(R5)HCOOR5, (CH2)nN(R5)CH2CO Het3, (CH2)nN(R5)CH2 Het3, (CH2)nN(R5)CH2CH2 Het3, (CH2)nN(R5)CH2CH2N(R5)CH2COOR5, (CH2)nN(R5)CH2CHNR5)2, CH═CHCOOR5, CH═CHCH2NR5 Het3, CH═CHCH2N(R5)2, CH═CHCH2OR5 or (CH2)nN(R5)Ar,
- Het3 is 1-piperidyl, 1-piperazyl, 1-(4-methyl)piperazyl, 4-methylpiperazin-1-ylamine, 1-pyrrolidinyl, 1-pyrazolidinyl, 1-(2-methyl)pyrazolidinyl, 1-imidazolidinyl or 1-(3-methyl)imidazolidinyl or 4-pyridyl, which may be unsubstituted or substituted by one or more CN groups, 2- or 4-pyridazyl, 2-, 4- or 5-pyrimidyl, or 2- or 3-pyrazinyl or one of the following groups
- R5 denotes H or A,
- A denotes straight-chain or branched alkyl or alkoxy having 1 to 10 C atoms, alkenyl or alkoxyalkyl having 2 to 10 C atoms,
- Ar denotes a phenyl radical which is unsubstituted or mono- or polysubstituted by A and/or Hal, OR5, OOCR5, COOR5, CON(R5)2, CN, NO2, NH2, NHCOR5, CF3 or SO2CH3,
- n denotes 0, 1, 2, 3, 4 or 5,
- Hal denotes F, Cl, Br or I, and
- X denotes N, or
- in the case where R1 denotes one of the following groups
- and/or R2 denotes
- in which R denotes H or an alkyl group having 1 to 6 C atoms,
- alternatively denotes CH,
- or an enantiomer, racemate, or a mixture of enantiomers thereof,
- or a pharmaceutically acceptable salt thereof.
16 more elements
Dependencies are inferred from the claim text.