http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-0663395-A1

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filingDate 1994-12-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_eab55fef5add107b5da782d6a88f26cc
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_a4892c2067057a2c8a1e163ac55acbc6
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publicationDate 1995-07-19-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber EP-0663395-A1
titleOfInvention 3-(phenylalkylaminoalkyloxy)-5-phenylpyrazole derivatives, process and intermediates for their preparation and their use as cardiac rhythm reduction agent
abstract n eine ganze Zahl von 1 bis 5 bedeutet, A für eine Gruppe der allgemeinen Formel an worin R¹ Wasserstoff oder eine niedere Alkylgruppe bedeutet und Q eine (CH₂) m -Gruppe, worin m 2 bis 8 bedeutet und welche gegebenenfalls in α-Stellung zu dem Sauerstoffatom durch 1 bis 2 niedere Alkylgruppen substituiert sein kann, oder die 2-Hydroxypropylenkette darstellt, steht, noder A für eine Gruppe der allgemeinen Formel bn worin p 4 bis 6 bedeutet und B eine (CH₂) r -Gruppe, worin r 1 bis 3 bedeutet und welche gegebenenfalls in α-Stellung zu dem Sauerstoffatom durch 1 bis 2 niedere Alkylgruppen substituiert sein kann, darstellt, steht, R² Wasserstoff, Halogen, niederes Alkyl, niederes Alkoxy, Hydroxy, Trifluormethyl oder Nitro oder, falls A keine OH-Gruppe enthält und R³, R⁶ und R⁷ nicht Hydroxy sind, auch niederes Alkanoyloxy bedeutet und R³ Wasserstoff, Halogen, niederes Alkyl, niederes Alkoxy, Hydroxy oder, falls A keine OH-Gruppe enthält und R², R⁶ und R⁷ nicht Hydroxy sind, auch niederes Alkanoyloxy bedeutet oder R² und R³ an zwei benachbarte Kohlenstoffatome gebunden sind und gemeinsam eine Alkylendioxygruppe mit 1 bis 2 Kohlenstoffatomen darstellen, R⁴ Wasserstoff oder niederes Alkyl bedeutet, R⁵ in 1- oder 2-Stellung angeordnet ist und Wasserstoff, niederes Alkyl oder eine Phenylniederalkylgruppe bedeutet, R⁶ Wasserstoff, niederes Alkyl, niederes Alkoxy, Hydroxy, Halogen, Trifluormethyl oder Nitro oder, falls A keine OH-Gruppe enthält und R², R³ und R⁷ nicht Hydroxy sind, auch niederes Alkanoyloxy bedeutet und R⁷ Wasserstoff, niederes Alkyl, niederes Alkoxy, Hydroxy oder Halogen oder, falls A keine OH-Gruppe enthält und R², R³ und R⁶ nicht Hydroxy sind, auch niederes Alkanoyloxy bedeutet oder R⁶ und R⁷ an zwei benachbarte Kohlenstoffatome gebunden sind und gemeinsam eine Alkylendioxygruppe mit 1 bis 2 Kohlenstoffatomen bilden, n sowie deren physiologisch verträgliche Säureadditionssalze sowie Zwischenprodukte der allgemeinen Formel XIn n worinn R¹' eine niedere Alkylgruppe oder eine Aminoschutzgruppe bedeutet, R²'' Wasserstoff, Halogen, niederes Alkyl, Trifluormethyl oder niederes Alkoxy bedeutet und R³' Wasserstoff, Halogen, niederes Alkyl oder niederes Alkoxy bedeutet oder R²'' und R³' an zwei benachbarte Kohlenstoffatome gebunden sind und gemeinsam eine Alkylendioxygruppe mit 1 bis 2 Kohlenstoffatomen darstellen, n eine ganze Zahl von 1 bis 5 bedeutet, Q' eine (CH₂) m' -Gruppe, worin m' 1 bis 7 bedeutet und welche gegebenenfalls in α-Stellung zu dem Sauerstoffatom durch 1 bis 2 niedere Alkylgruppen substituiert ist, darstellt, R⁴ Wasserstoff oder niederes Alkyl bedeutet, R⁵ in 1- oder 2-Stellung angeordnet ist und Wasserstoff, niederes Alkyl oder eine Phenylniederalkylgruppe bedeutet, R⁶'' Wasserstoff, niederes Alkyl, niederes Alkoxy, Halogen oder Trifluormethyl bedeutet und R⁷' Wasserstoff, niederes Alkyl, niederes Alkoxy, oder Halogen bedeutet oder R⁶'' und R⁷' an zwei benachbarte Kohlenstoffatome gebunden sind und gemeinsam eine Alkylendioxygruppe mit 1 bis 2 Kohlenstoffatomen bilden. 3- (Phenylalkylaminoalkyloxy) -5-phenylpyrazole compounds with heart rate-lowering effects and their preparation are described. The compounds have the general formula I. wherein n means an integer from 1 to 5, A for a group of the general formula a wherein R¹ is hydrogen or a lower alkyl group and Q is a (CH₂) m group, in which m is 2 to 8 and which may optionally be substituted in the α-position to the oxygen atom by 1 to 2 lower alkyl groups, or the 2-hydroxypropylene chain , stands, or A for a group of the general formula b where p is 4 to 6 and B is a (CH₂) r group, in which r is 1 to 3 and which may optionally be substituted in the α-position to the oxygen atom by 1 or 2 lower alkyl groups, R² Hydrogen, halogen, lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or nitro or, if A contains no OH group and R³, R⁶ and R⁷ are not hydroxy, also means lower alkanoyloxy and R³ Is hydrogen, halogen, lower alkyl, lower alkoxy, hydroxy or, if A contains no OH group and R², R⁶ and R⁷ are not hydroxy, also means lower alkanoyloxy or R² and R³ are bonded to two adjacent carbon atoms and together represent an alkylenedioxy group with 1 to 2 carbon atoms, R⁴ Means hydrogen or lower alkyl, R⁵ is arranged in the 1- or 2-position and denotes hydrogen, lower alkyl or a phenyl-lower alkyl group, R⁶ Is hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, trifluoromethyl or nitro or, if A contains no OH group and R², R³ and R⁷ are not hydroxy, also means lower alkanoyloxy and R⁷ Is hydrogen, lower alkyl, lower alkoxy, hydroxy or halogen or, if A contains no OH group and R², R³ and R⁶ are not hydroxy, also means lower alkanoyloxy or R⁶ and R⁷ are bonded to two adjacent carbon atoms and together form an alkylenedioxy group with 1 to 2 carbon atoms, as well as their physiologically acceptable acid addition salts and intermediates of the general formula XI wherein R¹ ' represents a lower alkyl group or an amino protecting group, R² '' Is hydrogen, halogen, lower alkyl, trifluoromethyl or lower alkoxy and R³ ' Is hydrogen, halogen, lower alkyl or lower alkoxy or R² '' and R³ ' are bonded to two adjacent carbon atoms and together represent an alkylenedioxy group with 1 to 2 carbon atoms, n means an integer from 1 to 5, Q ' represents a (CH₂) m ' group, in which m' represents 1 to 7 and which is optionally substituted in the α-position to the oxygen atom by 1 or 2 lower alkyl groups, R⁴ Means hydrogen or lower alkyl, R⁵ is arranged in the 1- or 2-position and denotes hydrogen, lower alkyl or a phenyl-lower alkyl group, R⁶ '' Is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R⁷ ' Is hydrogen, lower alkyl, lower alkoxy, or halogen or R⁶ '' and R⁷ ' are bonded to two adjacent carbon atoms and together form an alkylenedioxy group having 1 to 2 carbon atoms.
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Total number of triples: 417.