RU96102569A - Fluoroalkoxy substituted benzamides and their use as inhibitors of cyclic nucleotide phosphodiesters - Google Patents

Fluoroalkoxy substituted benzamides and their use as inhibitors of cyclic nucleotide phosphodiesters

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RU96102569A
RU96102569A RU96102569/04A RU96102569A RU96102569A RU 96102569 A RU96102569 A RU 96102569A RU 96102569/04 A RU96102569/04 A RU 96102569/04A RU 96102569 A RU96102569 A RU 96102569A RU 96102569 A RU96102569 A RU 96102569A
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halogen
alkoxy
hydrogen
alkyl
compounds
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RU96102569/04A
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RU2137754C1 (en
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Флокерци Дитер
Гуттерер Беате
Хатцельманн Армин
Шудт Кристиан
Беуме Рольф
Килиан Ульрих
П.О.Вольф Хорст
Амшлер Херманн
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Бик Гульден Ломберг Хемише Фабрик ГмбХ
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Priority claimed from PCT/EP1994/002169 external-priority patent/WO1995001338A1/en
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Claims (25)

1. Соединения формулы I
Figure 00000001

где один из заместителей R1 и R2 обозначает водород, 1-6С-алкокси, 3-7С-циклоалкилметокси, 3-7С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси, а другой - полностью или частично замещенный фтором 1-4С-алкокси;
R3 - фенил, пиридил, фенил, замещенный R3 1, R3 2 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают:
R3 1 - гидрокси, галоген, циано, карбоксил, трифторметил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил, С1С4-алкилкарбонил, 1-4С-алкилкарбонилокси, амино, моно- или ди-1-4С-алкиламино или 1-4С-алкилкарбониламино; R3 2 - водород, гидрокси, галоген, амино, трифторметил, 1-4С - алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; -R3 4 - гидрокси, галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил или амино; R3 5 - водород, галоген, амино или 1-4С-алкил; R3 6 - водород или галоген; R3 7 - водород или галоген,
соли этих соединений, а также N-оксиды пиридинов и их соли.1. The compounds of formula I
Figure 00000001

where one of the substituents R 1 and R 2 denotes hydrogen, 1-6C-alkoxy, 3-7C-cycloalkylmethoxy, 3-7C-cycloalkylmethoxy, benzyloxy or fully or partially substituted by fluorine 1-4C-alkoxy, and the other is fully or partially substituted fluorine 1-4C-alkoxy;
R 3 is phenyl, pyridyl, phenyl, substituted by R 3 1 , R 3 2 and R 3 3 , or pyridyl, substituted by R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively denote:
R 3 1 - hydroxy, halogen, cyano, carboxyl, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl, 1-4C-alkylcarbonyloxy, amino, mono- or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino; R 3 2 is hydrogen, hydroxy, halogen, amino, trifluoromethyl, 1-4C is alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; -R 3 4 - hydroxy, halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino; R 3 5 is hydrogen, halogen, amino or 1-4C-alkyl; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen,
salts of these compounds, as well as pyridine N-oxides and their salts. 2. Соединения формулы I по п.1, в которой R1 - водород, 1-6С-алкокси, 3-7С-циклоалкокси, 3-7С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R2 - полностью или частично замещенный фтором 1-4С-алкокси; R3 - фенил, пиридил, фенил, замещенный R3 1, R32 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают: R3 1 - гидрокси, галоген, циано, карбоксил, трифторметил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил, 1-4С-алкилкарбонил, 1-4С-алкилкарбонилокси, амино, моно- или ди-1-4С-алкиламино или 1-4С-алкилкарбониламино; R3 2 - водород, гидрокси, галоген, амино, трифторметил, 1-4С-алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - гидрокси, галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил или амино; R3 5 - водород, галоген, амино или 1-4С-алкил; R3 6 - водород или галоген; R3 7 - водород или галоген,
соли этих соединений, а также N-оксиды пиридинов и их соли.2. The compounds of formula I according to claim 1, in which R 1 is hydrogen, 1-6C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, benzyloxy, or fully or partially substituted by fluorine 1-4C-alkoxy; R 2 is fully or partially substituted by fluorine 1-4C-alkoxy; R 3 is phenyl, pyridyl, phenyl, substituted with R 3 1 , R 32 and R 3 3 , or pyridyl, substituted with R 3 4 , R 3 5 , R 3 6 and R 3 7 , with R 3 1 being R 3 7 respectively denote: R 3 1 - hydroxy, halogen, cyano, carboxyl, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, amino, mono- or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino; R 3 2 is hydrogen, hydroxy, halogen, amino, trifluoromethyl, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 is hydroxy, halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino; R 3 5 is hydrogen, halogen, amino or 1-4C-alkyl; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen,
salts of these compounds, as well as pyridine N-oxides and their salts. 3. Соединения формулы I по п.1, в которой R1 - водород, 1-6С-алкокси, 3-7С-циклоалкокси, 3-7С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R2 - полностью или частично замещенный фтором метокси; R3 - фенил, пиридил, фенил, замещенный R3 1, R3 2 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают: R3 1 - гидрокси, галоген, циано, карбоксил, трифторметил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил, 1-4С-алкилкарбонил, 1-4С-алкилкарбонилокси, амино, моно- или ди-1-4С-алкиламино или 1-4С-алкилкарбониламино; R3 2 - водород, гидрокси, галоген, амино, трифторметил, 1-4С-алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - гидрокси, галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил или амино; R3 5 - водород, галоген, амино или 1-4С-алкил; R3 6 - водород или галоген; R3 7 - водород и галоген, соли этих соединений, а также N-оксиды пиридинов и их соли.3. The compounds of formula I according to claim 1, in which R 1 is hydrogen, 1-6C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, benzyloxy or fully or partially substituted by fluorine 1-4C-alkoxy; R 2 is fully or partially substituted by fluorine methoxy; R 3 is phenyl, pyridyl, phenyl, substituted by R 3 1 , R 3 2 and R 3 3 , or pyridyl, substituted by R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively denote: R 3 1 - hydroxy, halogen, cyano, carboxyl, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, amino, mono - or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino; R 3 2 is hydrogen, hydroxy, halogen, amino, trifluoromethyl, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 is hydroxy, halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino; R 3 5 is hydrogen, halogen, amino or 1-4C-alkyl; R 3 6 is hydrogen or halogen; R 3 7 - hydrogen and halogen, salts of these compounds, as well as pyridine N-oxides and their salts. 4. Соединения формулы I по п.1, в которой R1 обозначает 3-7С-циклоалкокси, 3-7С-циклоалкилметокси или бензилокси; R2 - полностью или частично замещенный фтором 1-4С-алкокси; R3 - фенил, пиридил, фенил, замещенный R3 1, R3 2 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают: R3 1 - гидрокси, галоген, циано, карбоксил, трифторметил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил, 1-4С-алкилкарбонил, 1-4С-алкилкарбонилокси, амино, моно- или ди-1-4С-алкиламино или 1-4С-алкилкарбониламино; R3 2 - водород, гидрокси, галоген, амино, трифторметил, 1-4С-алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - гидрокси, галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил или амино; R3 5 - водород, галоген, амино или 1-4С-алкил; R3 6- водород или галоген; R3 7 - водород или галоген,
соли этих соединений, а также N-оксиды пиридинов и их соли.4. The compounds of formula I according to claim 1, in which R 1 denotes 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy or benzyloxy; R 2 is fully or partially substituted by fluorine 1-4C-alkoxy; R 3 is phenyl, pyridyl, phenyl, substituted by R 3 1 , R 3 2 and R 3 3 , or pyridyl, substituted by R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively denote: R 3 1 - hydroxy, halogen, cyano, carboxyl, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, amino, mono - or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino; R 3 2 is hydrogen, hydroxy, halogen, amino, trifluoromethyl, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 is hydroxy, halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino; R 3 5 is hydrogen, halogen, amino or 1-4C-alkyl; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen,
salts of these compounds, as well as pyridine N-oxides and their salts. 5. Соединения формулы I по п.1, в которой R1 - полностью или частично замещенный фтором 1-4С-алкокси; R2 - водород, 1-6С-алкокси, 3-7С-циклоалкокси, 3-7С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R3 - фенил, пиридил, фенил, замещенный R3 1, R3 2 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно-обозначают: R3 1 - гидрокси, галоген, циано, карбоксил, трифторметил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил, 1-4С-алкилкарбонил, 1-4С-алкилкарбонилокси, амино, моно- или ди-1-4С-алкиламино или 1-4С-алкилкарбониламино; R3 2 - водород, гидрокси, галоген, амино, трифторметил, 1-4С-алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - гидрокси, галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил или амино; R3 5 - водород, галоген, амино или 1-4С-алкил; R3 6 - водород или галоген; R3 7 - водород или галоген,
соли этих соединений, а также N-оксиды пиридинов и их соли.5. The compounds of formula I according to claim 1, in which R 1 is fully or partially fluorine-substituted 1-4C-alkoxy; R 2 is hydrogen, 1-6C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, benzyloxy or 1-4C-alkoxy, completely or partially replaced by fluorine; R 3 is phenyl, pyridyl, phenyl, substituted by R 3 1 , R 3 2 and R 3 3 , or pyridyl, substituted by R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively denote: R 3 1 - hydroxy, halogen, cyano, carboxyl, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, amino, mono- or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino; R 3 2 is hydrogen, hydroxy, halogen, amino, trifluoromethyl, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 is hydroxy, halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino; R 3 5 is hydrogen, halogen, amino or 1-4C-alkyl; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen,
salts of these compounds, as well as pyridine N-oxides and their salts. 6. Соединения формулы I по п.1, в которой R1 - полностью или чатично замещенный фтором 1-4С алкокси; R2 - 3-7С-циклоалкилметокси или бензилокси; R3 - фенил, пиридил, фенил, замещенный R31, R32 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают: R3 1 - гидрокси, галоген, циано, карбоксил, трифторметил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил, 1-4С-алкилкарбонил, 1-4С-алкилкарбонилокси, амино, моно- или ди-1-4С-алкиламино или 1-4С-алкилкарбониламино; R3 2 - водород, гидрокси, галоген, амино, трифторметил, 1-4С-алкил или 1-4С-алкокси; R33 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - гидрокси, галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси, 1-4С-алкоксикарбонил или амино; R3 5 - водород, галоген, амино или 1-4С-алкил; R3 6 - водород или галоген; R3 7 - водород или галоген,
соли этих соединений, а также N-оксиды пиридинов и их соли.6. The compounds of formula I according to claim 1, in which R 1 is completely or partially substituted by fluorine 1-4C alkoxy; R 2 - 3-7C-cycloalkylmethoxy or benzyloxy; R 3 is phenyl, pyridyl, phenyl, substituted by R 31 , R 32 and R 3 3 , or pyridyl, substituted by R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively denote : R 3 1 - hydroxy, halogen, cyano, carboxyl, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, amino, mono- or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino; R 3 2 is hydrogen, hydroxy, halogen, amino, trifluoromethyl, 1-4C-alkyl or 1-4C-alkoxy; R 33 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 is hydroxy, halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino; R 3 5 is hydrogen, halogen, amino or 1-4C-alkyl; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen,
salts of these compounds, as well as pyridine N-oxides and their salts. 7. Соединения формулы I по п.1, в которых R1 - 1-4С-алкокси, 3-5С-циклоалкокси, 3-5С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R2 1-4С-Алкокси; R3и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают:
R3 1 - галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси или 1-4С-алкоксикарбонил; R3 2 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - галоген или 1-4С-алкил; R3 5 - водород или галоген; R3 7 - водород или галоген,
соли этих соединений, а также N-оксиды пиридинов и их соли.7. The compounds of formula I according to claim 1, in which R 1 is 1-4C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy, benzyloxy, or 1-4C-alkoxy which is completely or partially substituted by fluorine; R 2 1-4C-Alkoxy; R 3 and R 3 3 , or pyridyl, substituted by R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively represent:
R 3 1 - halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, or 1-4C-alkoxycarbonyl; R 3 2 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 - halogen or 1-4C-alkyl; R 3 5 is hydrogen or halogen; R 3 7 is hydrogen or halogen,
salts of these compounds, as well as pyridine N-oxides and their salts. 8. Соединения формулы I по п.1, в которых R1 обозначает 1-4С-алкокси, 3-5С-циклоалкокси, 3-5С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R2 метокси; R3 - фенил, пиридил, фенил, замещенный R3 1, R3 2 R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7,
причем R3 1 - R3 7 соответственно обозначают: R3 1 - галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси или 1-4С-алкоксикарбонил; R3 2 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - галоген или 1-4С-алкил; R3 5 - водород или галоген; R3 6 - водород или галоген; R3 7 - водород или галоген;
соли этих соединений, а также N-оксиды пиридинов и их соли.8. The compounds of formula I according to claim 1, in which R 1 denotes 1-4C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy, benzyloxy or fully or partially substituted by fluorine 1-4C-alkoxy; R 2 methoxy; R 3 is phenyl, pyridyl, phenyl, substituted with R 3 1 , R 3 2 R 3 3 , or pyridyl, substituted with R 3 4 , R 3 5 , R 3 6 and R 3 7 ,
moreover, R 3 1 - R 3 7 respectively denote: R 3 1 - halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, or 1-4C-alkoxycarbonyl; R 3 2 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 - halogen or 1-4C-alkyl; R 3 5 is hydrogen or halogen; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen;
salts of these compounds, as well as pyridine N-oxides and their salts. 9. Соединения формулы I по п.1, в которых R1 - 3-5С-циклоалкокси, 3-5С-циклоалкилметокси или бензилокси; R2 - полностью или частично замещенный фтором 1-4С-алкокси; R3 - фенил, пиридил, фенил, замещенный R3 1, R3 2 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают: R3 1 - галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси или 1-4С-алкоксикарбонил; R3 2 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - галоген или 1-4С-алкил; R3 5 - водород или галоген; R3 6 - водород или галоген; R3 7 - водород или галоген;
соли этих соединений, а также N-оксиды пиридинов и их соли.9. The compounds of formula I according to claim 1, in which R 1 is 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy or benzyloxy; R 2 is fully or partially substituted by fluorine 1-4C-alkoxy; R 3 is phenyl, pyridyl, phenyl, substituted by R 3 1 , R 3 2 and R 3 3 , or pyridyl, substituted by R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively denote: R 3 1 - halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy or 1-4C-alkoxycarbonyl; R 3 2 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 - halogen or 1-4C-alkyl; R 3 5 is hydrogen or halogen; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen;
salts of these compounds, as well as pyridine N-oxides and their salts. 10. Соединения формулы I по п.1, в которых R1 обозначает полностью или частично замещенный фтором 1-4С-алкокси; R2 - 1-4С-алкокси, 3-5С-циклоалкокси, 3-5С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R3 - фенил, пиридил, фенил, замещенный R3 1, R3 2 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают: R31 - галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси или 1-4С-алкоксикарбонил; R3 2 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 3 - водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - галоген или 1-4С-алкил; R3 5 - водород или галоген; R3 6 - водород или галоген; R3 7 - водород или галоген;
соли этих соединений, а также N-оксиды пиридинов и их соли.10. The compounds of formula I according to claim 1, in which R 1 denotes fully or partially fluorine-substituted 1-4C-alkoxy; R 2 - 1-4C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy, benzyloxy or fully or partially fluorine-substituted 1-4C-alkoxy; R 3 is phenyl, pyridyl, phenyl, substituted by R 3 1 , R 3 2 and R 3 3 , or pyridyl, substituted by R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively denote: R 31 - halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, or 1-4C-alkoxycarbonyl; R 3 2 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 - halogen or 1-4C-alkyl; R 3 5 is hydrogen or halogen; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen;
salts of these compounds, as well as pyridine N-oxides and their salts. 11. Соединения формулы I по п.1, в которых R1 - полностью или частично замещенный фтором 1-4С-алкокси; R2 - 3-5С-циклоалкилметокси или бензилокси; R3 - обозначает фенил, пиридил, фенил, замещенный R3 1, R3 2 и R3 3, или пиридил, замещенный R3 4, R3 5, R3 6 и R3 7, причем R3 1 - R3 7 соответственно обозначают: R3 1 - галоген, циано, карбоксил, 1-4С-алкил, 1-4С-алкокси или 1-4С-алкоксикарбонил; R3 2-водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 3-водород, галоген, 1-4С-алкил или 1-4С-алкокси; R3 4 - галоген или 1-4С-алкил; R3 5 - водород или галоген; R3 6 - водород или галоген; R3 7 - водород или галоген;
если этих соединений, а также N-оксиды пиридинов и их соли.11. The compounds of formula I according to claim 1, in which R 1 is fully or partially fluorine-substituted 1-4C-alkoxy; R 2 - 3-5C-cycloalkylmethoxy or benzyloxy; R 3 - denotes phenyl, pyridyl, phenyl, substituted with R 3 1 , R 3 2 and R 3 3 , or pyridyl, substituted with R 3 4 , R 3 5 , R 3 6 and R 3 7 , and R 3 1 - R 3 7 respectively denote: R 3 1 - halogen, cyano, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, or 1-4C-alkoxycarbonyl; R 3 2 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy; R 3 4 - halogen or 1-4C-alkyl; R 3 5 is hydrogen or halogen; R 3 6 is hydrogen or halogen; R 3 7 is hydrogen or halogen;
if these compounds, as well as pyridine N-oxides and their salts. 12. Соединения формулы I по п.1, в которых R1 - 1-4С-алкокси, 3-5С-циклоалкокси, 3-5С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R2 - полностью или частично замещенный фтором 1-4С-алкокси; R3 - 2-бромфенил, 2,6-дихлор-4- этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил, 2,4,6-трифторфенил, 2-хлор-6-метилфенил, 2,6- диметилфенил, 2,6- дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирид-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6-трифторпирид- 4-ил, 3,5-дихлор-2,6- дифторпирид-4-ил или 2,6-дихлорпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.12. Compounds of formula I in accordance with claim 1, in which R 1 is 1-4C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy, benzyloxy or 1-4C-alkoxy which is completely or partially substituted by fluorine; R 2 is fully or partially substituted by fluorine 1-4C-alkoxy; R 3 - 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonyl, 2,6-dimethoxyphenyl, 4-cyano-2-fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6 - dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid-2-yl, 2-chloropyrid-3-yl, 3,5-dibromopyrid-2-yl , 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyrid-4-yl, 3,5-dichloro-2,6-difluorpyrid-4-yl or 2,6 dichloropyrid-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 13. Соединения формулы I по п.1, в которых R1 - 1-4С-алкокси, 3-5С- циклоалкокси, 3-5С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R2 - полностью или частично замещенный фтором метокси, и R3 - 2-бромфенил, 2,6-дихлор-4- этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил, 2,4,6-трифторфенил, 2-хлор-6-метилфенил, 2,6-диметилфенил, 2,6-дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирид-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6-трифторпирил-4-ил, 3,5-дихлор-2,6- дифторпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.13. Compounds of formula I in accordance with claim 1, in which R 1 is 1-4C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy, benzyloxy or 1-4C-alkoxy completely or partially substituted by fluorine; R 2 is fully or partially substituted by fluorine methoxy, and R 3 is 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonyl, phenyl, 2,6-dimethoxyphenyl, 4-cyano-2-fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6-dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid-2-yl, 2-chloropyrid-3- yl, 3,5-dibromopyrid-2-yl, 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyril-4-yl, 3,5-dichloro-2, 6-difluoride-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 14. Соединения формулы I по п.1, в которых R1 - 3-5С-циклоалкокси, 3-5С-циклоалкилметокси или бензилокси, R2 - полностью или частично замещенный фтором 1-4С-алкокси; R3 - 2-бромфенил, 2,6-дихлор-4-этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил,2,4,6- трифторфенил, 2-хлор-6-метилфенил, 2,6-диметилфенил, 2,6- дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирид-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6-трифторпирид-4-ил, 3,5-дихлор-2,6-дифторпирид-4-ил или 2,6-дихлорпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.14. The compounds of formula I according to claim 1, in which R 1 is 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy or benzyloxy, R 2 is 1-4C-alkoxy completely or partially substituted by fluorine; R 3 - 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonyl, 2,6-dimethoxyphenyl, 4-cyano-2-fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6 -dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid-2-yl, 2-chloropyrid-3-yl, 3,5-dibromopyrid-2-yl , 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyrid-4-yl, 3,5-dichloro-2,6-difluorpyrid-4-yl or 2,6 dichloropyrid-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 15. Соединения формулы I по п.1, в которых R1 - полностью или частично замещенный фтором 1-4С-алкокси, R3 - 1-4С-алкокси, 3-5С-циклоалкокси, 3-5С-циклоалкилметокси, бензилокси или полностью или частично замещенный фтором 1-4С-алкокси; R3 - 2-бромфенил, 2,6-дихлор-4- этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил, 2,4,6- трифторфенил, 2-хлор-6-метилфенил, 2,6-диметилфенил, 2,6- дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирид-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6-трифторпирид-4-ил, 3,5-дихлор-2,6-дифторпирид-4-ил или 2,6-дихлорпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.15. The compounds of formula I according to claim 1, in which R 1 is fully or partially substituted by fluorine 1-4C-alkoxy, R 3 - 1-4C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy, benzyloxy or or partially substituted by fluorine 1-4C-alkoxy; R 3 - 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonyl, 2,6-dimethoxyphenyl, 4-cyano-2-fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6 -dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid-2-yl, 2-chloropyrid-3-yl, 3,5-dibromopyrid-2-yl , 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyrid-4-yl, 3,5-dichloro-2,6-difluorpyrid-4-yl or 2,6 dichloropyrid-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 16. Соединения формулы I по п.1, в которых R1 - полностью или частично замещенный фтором 1-4С-алкокси; R2 - 3-5С-циклоалкилметокси или бензилокси; R3 - 2-бромфенил, 2,6-дихлор-4-этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил, 2,4,6-трифторфенил, 2-хлор-6-метилфенил, 2,6-диметилфенил, 2,6- дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирид-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6-трифторпирид-4-ил, 3,5-дихлор-2,6-дифторпирид-4-ил или 2,6-дихлорпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.16. The compounds of formula I according to claim 1, in which R 1 is fully or partially fluorine-substituted 1-4C-alkoxy; R 2 - 3-5C-cycloalkylmethoxy or benzyloxy; R 3 - 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonyl, 2,6-dimethoxyphenyl, 4-cyano-2-fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6 -dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid-2-yl, 2-chloropyrid-3-yl, 3,5-dibromopyrid-2-yl , 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyrid-4-yl, 3,5-dichloro-2,6-difluorpyrid-4-yl or 2,6 dichloropyrid-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 17. Соединения формулы I по п.1, в которых R1 - дифторметокси; R2 - метокси, этокси, изопропокси, циклопентилокси, циклопропилметокси, циклобутилметокси, дифторметокси или 2,2,2-трифторэтокси; R3 - 2-бромфенил, 2,6-дихлор-4-этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил, 2,4,6-трифторфенил, 2-хлор-6-метилфенил, 2,6-диметилфенил,2,6-дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирид-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6-трифторпирил-4-ил, 3,5-дихлор-2,6-дифторпирид-4-ил или 2,6-дихлорпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.17. The compounds of formula I according to claim 1, in which R 1 is difluoromethoxy; R 2 is methoxy, ethoxy, isopropoxy, cyclopentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, difluoromethoxy or 2,2,2-trifluoroethoxy; R 3 - 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonyl, 2,6-dimethoxyphenyl, 4-cyano-2-fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6 -dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid-2-yl, 2-chloropyrid-3-yl, 3,5-dibromopyrid-2-yl , 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyril-4-yl, 3,5-dichloro-2,6-difluoropyrid-4-yl or 2,6 dichloropyrid-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 18. Соединения формулы I по п.1, в которых R1 - дифторметокси; R2 - метокси, циклопропилметокси, циклобутилметокси или дифторметокси; R3 - 2-бромфенил, 2,6-дихлор-4- этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил, 2,4,6-трифторфенил, 2-хлор-6-метилфенил, 2,6-диметилфенил,2,6- дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирил-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6-трифторпирид-4-ил, 3,5-дихлор-2,6-дифторпирид -4-ил или 2,6-дихлорпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.18. The compounds of formula I according to claim 1, in which R 1 - difluoromethoxy; R 2 is methoxy, cyclopropylmethoxy, cyclobutylmethoxy or difluoromethoxy; R 3 - 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonyl, 2,6-dimethoxyphenyl, 4-cyano-2-fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6 -dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid-2-yl, 2-chloropyril-3-yl, 3,5-dibromopyrid-2-yl , 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyrid-4-yl, 3,5-dichloro-2,6-difluorpyrid-4-yl or 2,6 dichloropyrid-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 19. Соединения формулы I по п.1, в которых R1 - метокси, н-пропокси, н-бутокси, циклопропилметокси или 2,2,2-трифторэтокси, R2 - дифторметокси; R - 2-бромфенил, 2,6-дихлор-4- этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил, 2,4,6-трифторфенил, 2-хлор-6-метилфенил, 2,6-диметилфенил, 2,6-дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирид-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6-трифторпирид-4-ил, 3,5-дихлор-2,6-дифторпирид-4-ил или 2,6-дихлорпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.19. Compounds of formula I in accordance with claim 1, in which R 1 is methoxy, n-propoxy, n-butoxy, cyclopropylmethoxy or 2,2,2-trifluoroethoxy, R 2 is difluoromethoxy; R - 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonylphenyl, 2,6-dimethoxyphenyl, 4-cyano-2-fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6- dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid-2-yl, 2-chloropyrid-3-yl, 3,5-dibromopyrid-2-yl, 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyrid-4-yl, 3,5-dichloro-2,6-difluorpyrid-4-yl or 2,6- dichloropyrid-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 20. Соединения формулы I по п.1, в которых R1 - дифторметокси, R2 - циклопропилметокси и R3 - 2-бромфенил, 2,6-дихлор-4- этоксикарбонилфенил, 2,6-диметоксифенил, 4-циано-2-фторфенил,2,4,6 -трифторфенил, 2-хлор-6-метилфенил, 2,6-диметилфенил,2,6- дифторфенил, 2,6-дихлорфенил, 3,5-дихлорпирид-4-ил, 3-метилпирид-2-ил, 2-хлорпирид-3-ил, 3,5-дибромпирид-2-ил, 2,3,5,6-тетрафторпирид-4-ил, 3-хлор-2,5,6- трифторпирид-4-ил, 3,5-дихлор-2,6- дифторпирид-4-ил или 2,6-дихлорпирид-3-ил,
соли этих соединений, а также N-оксиды пиридинов и их соли.20. Compounds of formula I according to claim 1, in which R 1 is difluoromethoxy, R 2 is cyclopropylmethoxy and R 3 is 2-bromophenyl, 2,6-dichloro-4-ethoxycarbonylphenyl, 2,6-dimethoxyphenyl, 4-cyano-2 -fluorophenyl, 2,4,6-trifluorophenyl, 2-chloro-6-methylphenyl, 2,6-dimethylphenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 3,5-dichloropyrid-4-yl, 3-methylpyrid -2-yl, 2-chloropyrid-3-yl, 3,5-dibromopyrid-2-yl, 2,3,5,6-tetrafluoropyrid-4-yl, 3-chloro-2,5,6-trifluoropyrid-4 -yl, 3,5-dichloro-2,6-difluoropyrid-4-yl or 2,6-dichloropyrid-3-yl,
salts of these compounds, as well as pyridine N-oxides and their salts. 21. Способ получения соединений формулы I по п.1 и их солей, а также N-оксидов пиридинов и их солей, отличающийся тем, что соединения формулы II
Figure 00000002

где R1 и R2 имеют значения, указанные в п.1, а Х - подходящая удаляемая группа,
подвергают взаимодействию с аминами Р3-NH2 и что при желании полученные соединения формулы I затем переводят в их соли и/или переводят полученные пиридины в N-оксиды и что при желании затем переводят полученные соли соединений 1 в свободные соединения.21. The method of producing compounds of formula I according to claim 1 and their salts, as well as pyridine N-oxides and their salts, characterized in that the compounds of formula II
Figure 00000002

where R 1 and R 2 have the meanings indicated in claim 1, and X is a suitable leaving group,
is reacted with amines P 3 -NH 2 and that, if desired, the obtained compounds of formula I are then converted to their salts and / or the resulting pyridines are converted to N-oxides and that, if desired, then the obtained salts of compounds 1 are converted to free compounds. 22. Лекарственное средство, содержащее одно или несколько соединений по п.1. 22. Drug containing one or more compounds according to claim 1. 23. Соединения по п.1, для применения при лечении болезней. 23. Compounds according to claim 1, for use in the treatment of diseases. 24. Применение соединений по п.1 для получения лекарственных средств для лечения заболеваний дыхательных путей. 24. The use of compounds according to claim 1 for obtaining drugs for the treatment of diseases of the respiratory tract. 25. Применение соединения по п.1 для получения лекарственных средств для лечения дерматозов. 25. The use of a compound according to claim 1 for the preparation of a medicament for the treatment of dermatoses.
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