RU2003122341A - NEW Quinuclidine Carbamate Derivatives and Drug Compositions Containing Named Derivatives - Google Patents

NEW Quinuclidine Carbamate Derivatives and Drug Compositions Containing Named Derivatives

Info

Publication number
RU2003122341A
RU2003122341A RU2003122341/04A RU2003122341A RU2003122341A RU 2003122341 A RU2003122341 A RU 2003122341A RU 2003122341/04 A RU2003122341/04 A RU 2003122341/04A RU 2003122341 A RU2003122341 A RU 2003122341A RU 2003122341 A RU2003122341 A RU 2003122341A
Authority
RU
Russia
Prior art keywords
azoniabicyclo
octane
group
bromide
compound according
Prior art date
Application number
RU2003122341/04A
Other languages
Russian (ru)
Other versions
RU2296762C2 (en
Inventor
Альберо Мария Антония Буил
Форнер Мария Долорс Фернандес
Киньонес Мария Прат
Original Assignee
Альмиралль Продесфарма Аг
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 Альмиралль Продесфарма Аг filed Critical Альмиралль Продесфарма Аг
Publication of RU2003122341A publication Critical patent/RU2003122341A/en
Application granted granted Critical
Publication of RU2296762C2 publication Critical patent/RU2296762C2/en

Links

Claims (28)

1. Соединение, которое представляет собой карбамат формулы (I):1. The compound, which is a carbamate of the formula (I):
Figure 00000001
Figure 00000001
 в которойwherein R1 представляет собойR1 represents
Figure 00000002
Figure 00000002
 R3 означает атом водорода или галогена, или группу низшего алкила с прямой или разветвленной цепью, или цианогруппу;R3 represents a hydrogen or halogen atom, or a straight or branched chain lower alkyl group, or a cyano group; R2 означает группу бензила, фенетила, фуран-2-илметила, фуран-3-илметила, тиофен-2-илметила или тиофен-3-илметила или группу алкила с прямой или разветвленной цепью, содержащую от 3 до 8 атомов углерода, группу алкенила, содержащую от 3 до 8 атомов углерода, или циклоалкильную группу из 3-6 атомов углерода;R2 means a benzyl, phenethyl, furan-2-ylmethyl, furan-3-ylmethyl, thiophen-2-ylmethyl or thiophen-3-ylmethyl group or a straight or branched chain alkyl group containing from 3 to 8 carbon atoms, an alkenyl group, containing from 3 to 8 carbon atoms, or a cycloalkyl group of 3-6 carbon atoms; р равно 1 или 2, а замещение в азониабициклическом кольце может быть в положении 2, 3 или 4, включая все возможные конфигурации асимметричных атомов углерода;p is 1 or 2, and the substitution in the azoniabicyclic ring may be in position 2, 3 or 4, including all possible configurations of asymmetric carbon atoms; или его фармацевтически приемлемая соль.or a pharmaceutically acceptable salt thereof. 2. Соединение по п.1, которое изображается формулой (II):2. The compound according to claim 1, which is depicted by the formula (II):
Figure 00000003
Figure 00000003
 в которой R1, R2 и р определены как указано в п.1;in which R1, R2 and p are defined as indicated in claim 1; m означает целое число от 0 до 8;m is an integer from 0 to 8; А означает группу –СН2-, -СН=CR4-, -CR4=CH-, -CO-, -O-, -S-, -S(O)-, -SO2-, -NR4- или –CR4R5-, в которых R4 и R5, каждый независимо означает атом водорода, группу низшего алкила с прямой или разветвленной цепью, или R4 и R5 вместе образуют алициклическое кольцо;And means the group —CH 2 -, —CH = CR4-, -CR4 = CH-, -CO-, -O-, -S-, -S (O) -, -SO 2 -, -NR4- or –CR4R5 - in which R4 and R5 each independently represent a hydrogen atom, a straight or branched chain lower alkyl group, or R4 and R5 together form an alicyclic ring; n соответствует целому числу от 0 до 4;n corresponds to an integer from 0 to 4; В означает атом водорода, алкоксигруппу, циклоалкильную группу, -COOR4 или –OOCR4, в которых R4 определено как указано выше, или цианогруппу, группу нафталинила, группу 5,6,7,8-тетрагидронафталинила, бифенильную группу или группу формулы (i) или (ii)B means a hydrogen atom, an alkoxy group, a cycloalkyl group, —COOR4 or –OOCR4 in which R4 is as defined above, or a cyano group, a naphthalenyl group, a 5,6,7,8-tetrahydronaphthalenyl group, a biphenyl group or a group of formula (i) or (ii)
Figure 00000004
Figure 00000005
Figure 00000004
Figure 00000005
 где Z означает O, N или S;where Z is O, N or S; R3 определено как указано выше; иR3 is as defined above; and R6, R7 и R8, каждый независимо, означают атом водорода или галогена, или группу гидрокси, фенила, –OR4, -SR4, -NR4R5,R6, R7 and R8, each independently, represent a hydrogen or halogen atom, or a hydroxy, phenyl group, –OR4, —SR4, —NR4R5, -NHCOR4, -CONR4R5, -CN, -NO2, -COOR4 или –CF3, или замещенную либо незамещенную группу низшего алкила с прямой или разветвленной цепью;—NHCOR4, —CONR4R5, —CN, —NO 2 , —COOR4, or —CF 3 , or a substituted or unsubstituted straight or branched chain lower alkyl group; где R4 и R5, каждый независимо, означают атом водорода, группу низшего алкила с прямой или разветвленной цепью, или R4 и R5 вместе образуют алициклическое кольцо; или R6 и R7 вместе образуют ароматическое, алициклическое или гетероциклическое кольцо; иwhere R4 and R5 each independently represent a hydrogen atom, a straight or branched chain lower alkyl group, or R4 and R5 together form an alicyclic ring; or R6 and R7 together form an aromatic, alicyclic or heterocyclic ring; and Х- означает фармацевтически приемлемый анион моно- или поливалентной кислоты.X - means a pharmaceutically acceptable anion of mono - or polyvalent acid. 3. Соединение по п.1 или п.2, в котором р равно 2.3. The compound according to claim 1 or claim 2, in which p is 2. 4. Соединение по любому из пп.1–3, в котором R1 означает группу фенила, 4-фторфенила, 4-метилфенила, тиофен-2-илметила, тиенила или фуран-2-илметила.4. The compound according to any one of claims 1 to 3, in which R1 is a group of phenyl, 4-fluorophenyl, 4-methylphenyl, thiophen-2-ylmethyl, thienyl or furan-2-ylmethyl. 5. Соединение по любому из предшествующих пунктов, в котором R2 означает группу бензила, тиофен-2-илметила, тиофен-3-илметила, фуран-2-илметила, фенетила, пент-4-енила, пентила, бутила, аллила или циклопентила.5. The compound according to any one of the preceding paragraphs, wherein R2 is a group of benzyl, thiophen-2-ylmethyl, thiophen-3-ylmethyl, furan-2-ylmethyl, phenethyl, pent-4-enyl, pentyl, butyl, allyl or cyclopentyl. 6. Соединение по любому из предшествующих пунктов, в котором В представляет собой атом водорода или замещенную или незамещенную группу фенила, пирролила, тиенила или фурила, или группу бифенила, нафталинила, 5,6,7,8-тетрагидронафталинила или бензо[1,3]диоксолила.6. The compound according to any one of the preceding paragraphs, in which B represents a hydrogen atom or a substituted or unsubstituted phenyl, pyrrolyl, thienyl or furyl group, or a biphenyl, naphthalenyl, 5,6,7,8-tetrahydronaphthalenyl or benzo group [1,3 ] dioxolyl. 7. Соединение по п.6, в котором В означает замещенную или незамещенную группу фенила и R6, R7 и R8, каждый независимо, означают атом водорода или галогена, или группу гидроксила, метила, -СН2ОН, -OMe, -NMe2, -NHCOMe, -CONH2, -CN, -NO2, -COOMe или -CF3.7. The compound according to claim 6, in which B means a substituted or unsubstituted phenyl group and R6, R7 and R8 each independently represent a hydrogen or halogen atom, or a hydroxyl, methyl group, —CH 2 OH, —OMe, —NMe 2 , -NHCOMe, -CONH 2 , -CN, -NO 2 , -COOMe or -CF 3 . 8. Соединение по п.7, где В означает группу фенила, 4-фторфенила или 3-гидроксифенила.8. The compound of claim 7, wherein B is a phenyl, 4-fluorophenyl or 3-hydroxyphenyl group. 9. Соединение по любому из предшествующих пунктов, в котором n=0 или 1; m соответствует целому числу от 1 до 6; и А означает группу –СН2-, -СН=СН-, -СО-, -NMe, -O- или -S-.9. The compound according to any one of the preceding paragraphs, in which n = 0 or 1; m corresponds to an integer from 1 to 6; and A means the group —CH 2 -, —CH = CH—, —CO—, —NMe, —O— or —S—. 10. Соединение по п.9, в котором m равно 1, 2 или 3, а А означает группу –СН2-, -СН=СН- или –О-.10. The compound according to claim 9, in which m is 1, 2 or 3, and A means a group —CH 2 -, —CH = CH— or –O—. 11. Соединение по любому из предшествующих пунктов, в котором B-(CH2)n-A-(CH2)m- соответствует группе, выбранной из 3-феноксипропила, 2-феноксиэтила, 3-фенилаллила, фенетила, 3-фенилпропила, 3-(3-гидроксифенокси)пропила, 3-(4-фторфенокси)пропила, 3-тиофен-2-илпропила, 1-аллила и 1-гептила.11. The compound according to any one of the preceding paragraphs, in which B- (CH 2 ) n -A- (CH 2 ) m corresponds to a group selected from 3-phenoxypropyl, 2-phenoxyethyl, 3-phenylallyl, phenethyl, 3-phenylpropyl, 3- (3-hydroxyphenoxy) propyl, 3- (4-fluorophenoxy) propyl, 3-thiophen-2-ylpropyl, 1-allyl and 1-heptyl. 12. Соединение по любому из предшествующих пунктов, в котором Х- представляет собой анион хлорида, бромида или трифторацетата.12. The compound according to any one of the preceding paragraphs, in which X - represents the anion of chloride, bromide or trifluoroacetate. 13. Соединение по любому из предшествующих пунктов, в котором группа азониабицикло замещена в положении 3.13. A compound according to any one of the preceding claims wherein the azoniabicyclo group is substituted at position 3. 14. Соединение по п.13, в котором заместитель в положении 3 имеет (R)-конфигурацию.14. The compound of claim 13, wherein the substituent at position 3 has a (R) configuration. 15. Соединение по любому из предшествующих пунктов, которое является отдельным (одиночным) изомером.15. The compound according to any one of the preceding paragraphs, which is a separate (single) isomer. 16. Соединение по п.1, которое представляет собой:16. The compound according to claim 1, which is: 1-азабицикло[2.2.2]окт-3-(R)иловый эфир бензилфенилкарбаминовой кислоты;Benzylphenylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир бензил(4-фторфенил)карбаминовой кислоты;Benzyl (4-fluorophenyl) carbamic acid 1-azabicyclo [2.2.2] oct-3- (R) yl ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир бензил-п-толилкарбаминовой кислоты;Benzyl p-tolyl carbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир бутилфенилкарбаминовой кислоты;Butylphenylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир фенилтиофен-2-илметилкарбаминовой кислоты;Phenylthiophen-2-ylmethylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир фенетилфенилкарбаминовой кислоты;1-azabicyclo [2.2.2] oct-3- (R) phenyl phenylcarbamic acid ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир пентилфенилкарбаминовой кислоты;Pentylphenylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир пент-4-енилфенилкарбаминовой кислоты;Pent-4-enylphenylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир фенилтиофен-3-илметилкарбаминовой кислоты;Phenylthiophen-3-ylmethylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир бутилтиофен-2-илметилкарбаминовой кислоты;Butylthiophen-2-ylmethylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир бис-тиофен-2-илметилкарбаминовой кислоты;Bis-thiophen-2-ylmethylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир фуран-2-илметил-2-тиофен-2-илметилкарбаминовой кислоты;1-azabicyclo [2.2.2] oct-3- (R) yl ester of furan-2-ylmethyl-2-thiophen-2-ylmethylcarbamic acid; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир аллилтиофен-2-илметилкарбаминовой кислоты;Allylthiophen-2-ylmethylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир циклопентилтиофен-2-илметилкарбаминовой кислоты;Cyclopentylthiophen-2-ylmethylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир фуран-2-илметилфенилкарбаминовой кислоты;1-azabicyclo [2.2.2] oct-3- (R) yl ester of furan-2-ylmethylphenylcarbamic acid; 1-азабицикло[2.2.2]окт-3-(R)иловый эфир бис-фуран-2-илметилкарбаминовой кислоты;Bis-furan-2-ylmethylcarbamic acid 1-azabicyclo [2.2.2] oct-3- (R) ester; 1-азабицикло[2.2.1]гепт-4-(R)иловый эфир бензилфенилкарбаминовой кислоты;Benzylphenylcarbamic acid 1-azabicyclo [2.2.1] hept-4- (R) ester; 1-азабицикло[2.2.2]окт-4-(R)иловый эфир бензилфенилкарбаминовой кислоты;Benzylphenylcarbamic acid 1-azabicyclo [2.2.2] oct-4- (R) ester; или его фармацевтически приемлемая соль.or a pharmaceutically acceptable salt thereof. 17. Соединение по п.2, которое представляет собой:17. The compound according to claim 2, which is: 3-(R)(Бензилфенилкарбамоил-окси)-1-(3-фенилаллил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Benzylphenylcarbamoyloxy) -1- (3-phenylallyl) -1-azoniabicyclo [2.2.2] octane, bromide; 1-Аллил-3-(R)(бензилфенилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, бромид;1-allyl-3- (R) (benzylphenylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бензилфенилкарбамоил-окси)-1-фенетил-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Benzylphenylcarbamoyloxy) -1-phenethyl-1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бензилфенилкарбамоил-окси)-1-(3-тиофен-2-илпропил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Benzylphenylcarbamoyloxy) -1- (3-thiophen-2-ylpropyl) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бензилфенилкарбамоил-окси)-1-(3-фенилпропил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Benzylphenylcarbamoyloxy) -1- (3-phenylpropyl) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бензилфенилкарбамоил-окси)-1-(2-феноксиэтил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Benzylphenylcarbamoyloxy) -1- (2-phenoxyethyl) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бензилфенилкарбамоил-окси)-1-(3-фенилаллил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Benzylphenylcarbamoyloxy) -1- (3-phenylallyl) -1-azoniabicyclo [2.2.2] octane, bromide; 1-Аллил-3-(R)(бензилфенилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, бромид;1-allyl-3- (R) (benzylphenylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бутилфенилкарбамоил-окси)-1-(2-феноксиэтил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Butylphenylcarbamoyloxy) -1- (2-phenoxyethyl) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бутилфенилкарбамоил-окси)-1-[3-(3-гидроксифенокси)пропил]-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Butylphenylcarbamoyloxy) -1- [3- (3-hydroxyphenoxy) propyl] -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бутилфенилкарбамоил-окси)-1-[3-(4-фторфенокси)пропил]-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Butylphenylcarbamoyloxy) -1- [3- (4-fluorophenoxy) propyl] -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бутилфенилкарбамоил-окси)-1-(3-тиофен-2-илпропил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Butylphenylcarbamoyloxy) -1- (3-thiophen-2-ylpropyl) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бутилфенилкарбамоил-окси)-1-(3-фенилпропил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Butylphenylcarbamoyloxy) -1- (3-phenylpropyl) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Фенилтиофен-2-илметилкарбамоил-окси)-1-(3-тиофен-2-илпропил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Phenylthiophen-2-ylmethylcarbamoyloxy) -1- (3-thiophen-2-ylpropyl) -1-azoniabicyclo [2.2.2] octane, bromide; 1-(2-Феноксиэтил)-3-(R)(фенилтиофен-2-илметилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, бромид;1- (2-Phenoxyethyl) -3- (R) (phenylthiophen-2-ylmethylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane; bromide; 1-Аллил-3-(R)(фенилтиофен-2-илметилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, бромид;1-allyl-3- (R) (phenylthiophen-2-ylmethylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Фенетилфенилкарбамоил-окси)-1-(2-феноксиэтил)-1-азониабицикло[2.2.2]октан, трифторацетат;3- (R) (Phenethylphenylcarbamoyloxy) -1- (2-phenoxyethyl) -1-azoniabicyclo [2.2.2] octane; trifluoroacetate; 1-Гептил-3-(R)(пент-4-енилфенилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, трифторацетат;1-Heptyl-3- (R) (pent-4-enylphenylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane, trifluoroacetate; 1-Аллил-3-(R)(фенилтиофен-3-илметилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, трифторацетат;1-allyl-3- (R) (phenylthiophen-3-ylmethylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane; trifluoroacetate; 3-(R)(Фенилтиофен-3-илметилкарбамоил-окси)-1-(3-тиофен-2-илпропил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Phenylthiophen-3-ylmethylcarbamoyloxy) -1- (3-thiophen-2-ylpropyl) -1-azoniabicyclo [2.2.2] octane, bromide; 1-(2-Феноксиэтил)-3-(R)(фенилтиофен-3-илметилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, бромид;1- (2-Phenoxyethyl) -3- (R) (phenylthiophen-3-ylmethylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бис-тиофен-2-илметилкарбамоил-окси)-1-(3-фенилпропил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (bis-thiophen-2-ylmethylcarbamoyloxy) -1- (3-phenylpropyl) -1-azoniabicyclo [2.2.2] octane, bromide; 3-(R)(Бис-тиофен-2-илметилкарбамоил-окси)-1-(3-тиофен-2-илпропил)-1-азониабицикло[2.2.2]октан, бромид;3- (R) (Bis-thiophen-2-ylmethylcarbamoyloxy) -1- (3-thiophen-2-ylpropyl) -1-azoniabicyclo [2.2.2] octane, bromide; 1-Аллил-3-(R)(аллилтиофен-2-илметилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, трифторацетат;1-Allyl-3- (R) (allylthiophen-2-ylmethylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane; trifluoroacetate; 3-(R)(Циклопентилтиофен-2-илметилкарбамоил-окси)-1-(3-фенилпропил)-1-азониабицикло[2.2.2]октан, трифторацетат;3- (R) (cyclopentylthiophen-2-ylmethylcarbamoyloxy) -1- (3-phenylpropyl) -1-azoniabicyclo [2.2.2] octane; trifluoroacetate; 3-(R)(Фуран-2-илметилфенилкарбамоил-окси)-1-(3-фенилпропил)-1-азониабицикло[2.2.2]октан, трифторацетат; или3- (R) (Furan-2-ylmethylphenylcarbamoyloxy) -1- (3-phenylpropyl) -1-azoniabicyclo [2.2.2] octane; trifluoroacetate; or 1-Аллил-3-(R)(бис-фуран-2-илметилкарбамоил-окси)-1-азониабицикло[2.2.2]октан, трифторацетат.1-Allyl-3- (R) (bis-furan-2-ylmethylcarbamoyloxy) -1-azoniabicyclo [2.2.2] octane, trifluoroacetate. 18. Соединение по любому из предшествующих пунктов, которое характеризуется тем, что имеет значение IC50 (нМ) для мускариновых рецепторов М3 менее 35.18. The compound according to any one of the preceding paragraphs, which is characterized in that it has an IC 50 (nM) for muscarinic M3 receptors of less than 35. 19. Способ получения карбамата формулы (I)19. A method of obtaining a carbamate of the formula (I)
Figure 00000006
Figure 00000006
 в которой R1, R2 и р определены как указано в любом из пп.1, 3-5 или 13-16, который включает взаимодействие соединения формулы (III):in which R1, R2 and p are defined as indicated in any one of claims 1, 3-5 or 13-16, which includes the interaction of the compounds of formula (III):
Figure 00000007
Figure 00000007
 с соединением формулы (IV):with the compound of formula (IV):
Figure 00000008
Figure 00000008
 где R1, R2 и р в формулах (III) и (IV) определены как указано в любом из пп.1, 3-5 или 13-16.where R1, R2 and p in formulas (III) and (IV) are defined as indicated in any one of claims 1, 3-5, or 13-16. 20. Способ получения соли формулы (II):20. A method of obtaining a salt of formula (II):
Figure 00000009
Figure 00000009
 в которой R1, R2, p, m, n, A, B и X определены как указано в любом из пп.1-17, который включает кватернизацию атома азота азониабициклического кольца соединения формулы (I):in which R1, R2, p, m, n, A, B and X are defined as indicated in any one of claims 1-17, which includes the quaternization of the nitrogen atom of the azoniabicyclic ring of the compound of formula (I):
Figure 00000010
Figure 00000010
 где R1, R2 и р определены как указано в любом из пп.1, 3-5 или 13-16,where R1, R2 and p are defined as indicated in any one of claims 1, 3-5 or 13-16, с алкилирующим агентом формулы (VI):with an alkylating agent of the formula (VI):
Figure 00000011
Figure 00000011
 в которой m, n, A и В определены как указано выше, а W означает уходящую группу.in which m, n, A and B are defined as described above, and W means a leaving group. 21. Способ по п.20, при котором W означает группу Х, которая определена в п.1 или 12.21. The method according to claim 20, in which W means a group X, which is defined in claim 1 or 12. 22. Способ по п.20 или п.21, в котором полученную реакционную смесь очищают экстракцией твердой фазы.22. The method according to claim 20 or claim 21, in which the resulting reaction mixture is purified by extraction of the solid phase. 23. Фармацевтическая композиция, содержащая соединение по любому из пп.1-18 в смеси с фармацевтически приемлемым носителем или разбавителем.23. A pharmaceutical composition comprising a compound according to any one of claims 1 to 18 in a mixture with a pharmaceutically acceptable carrier or diluent. 24. Соединение по любому из пп.1-18 или фармацевтическая композиция по п.23 для применения в способе терапевтического лечения человека или животного.24. The compound according to any one of claims 1 to 18 or the pharmaceutical composition according to item 23 for use in a method of therapeutic treatment of a human or animal. 25. Применение соединения по любому из пп.1-18 или фармацевтической композиции по п.23 в производстве лекарственного средства для лечения респираторного, урологического или желудочно-кишечного заболевания или нарушения.25. The use of a compound according to any one of claims 1 to 18 or a pharmaceutical composition according to claim 23 in the manufacture of a medicament for the treatment of a respiratory, urological or gastrointestinal disease or disorder. 26. Способ лечения респираторных, урологических или желудочно-кишечных заболеваний, который включает введение нуждающемуся в этом человеку или животному эффективного количества соединения по любому из пп.1-18 или фармацевтической композиции по п.23.26. A method for the treatment of respiratory, urological or gastrointestinal diseases, which comprises administering to a person or animal in need thereof an effective amount of a compound according to any one of claims 1 to 18 or a pharmaceutical composition according to claim 23. 27. Комбинированный продукт, содержащий соединение по любому из пп.1-18; и (iii) другое соединение, эффективное при лечении респираторного, урологического или желудочно-кишечного заболевания или нарушения для одновременного, раздельного или последовательного применения.27. The combined product containing the compound according to any one of claims 1 to 18; and (iii) another compound effective in treating a respiratory, urological or gastrointestinal disease or disorder for simultaneous, separate or sequential use. 28. Комбинированный продукт по п.27, содержащий соединение по любому из пп.1-18; и (iv) β2-агонист, стероид, антиаллергическое лекарственное средство, ингибитор фосфодиэстеразы IV и/или антагонист лейкотриена D4 (LTD4) для одновременного, раздельного или последовательного применения при лечении респираторного заболевания.28. The combined product according to item 27, containing the compound according to any one of claims 1 to 18; and (iv) a β 2 agonist, steroid, antiallergic drug, phosphodiesterase IV inhibitor and / or leukotriene D4 antagonist (LTD4) for simultaneous, separate or sequential use in the treatment of respiratory disease.
RU2003122341/04A 2000-12-22 2001-12-20 Quinuclidine carbamates, methods for their preparing and pharmaceutical composition based on thereof RU2296762C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES200003084 2000-12-22
ES200003084 2000-12-22

Publications (2)

Publication Number Publication Date
RU2003122341A true RU2003122341A (en) 2004-12-27
RU2296762C2 RU2296762C2 (en) 2007-04-10

Family

ID=8496114

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2003122341/04A RU2296762C2 (en) 2000-12-22 2001-12-20 Quinuclidine carbamates, methods for their preparing and pharmaceutical composition based on thereof

Country Status (33)

Country Link
US (3) US7208501B2 (en)
EP (1) EP1345937B1 (en)
JP (1) JP4445704B2 (en)
KR (1) KR100869722B1 (en)
CN (1) CN1298717C (en)
AR (1) AR035410A1 (en)
AT (1) ATE305468T1 (en)
AU (1) AU2002228015B2 (en)
BG (1) BG107930A (en)
BR (1) BR0116450A (en)
CA (1) CA2441896A1 (en)
CZ (1) CZ301323B6 (en)
DE (1) DE60113719T2 (en)
DK (1) DK1345937T3 (en)
EC (1) ECSP034660A (en)
EE (1) EE200300295A (en)
ES (1) ES2248409T3 (en)
HK (1) HK1055120A1 (en)
HU (1) HUP0303529A3 (en)
IL (1) IL156499A0 (en)
MX (1) MXPA03005583A (en)
MY (1) MY136674A (en)
NO (1) NO328707B1 (en)
NZ (1) NZ526580A (en)
PE (1) PE20020719A1 (en)
PL (1) PL362989A1 (en)
RU (1) RU2296762C2 (en)
SI (1) SI1345937T1 (en)
SK (1) SK8002003A3 (en)
UA (1) UA76131C2 (en)
UY (1) UY27092A1 (en)
WO (1) WO2002051841A1 (en)
ZA (1) ZA200304769B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2456286C2 (en) * 2006-11-14 2012-07-20 Астразенека Аб Quinuclidine derivatives of (hetero) arylcycloheptane carboxylic acids as muscarine receptor antagonists

Families Citing this family (117)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2165768B1 (en) 1999-07-14 2003-04-01 Almirall Prodesfarma Sa NEW DERIVATIVES OF QUINUCLIDINE AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM.
KR100751981B1 (en) 2000-06-27 2007-08-28 라보라토리오스 살바트, 에스.에이. Carbamates derived from arylalkylamines
CA2441896A1 (en) 2000-12-22 2002-07-04 Almirall Prodesfarma Ag Quinuclidine carbamate derivatives and their use as m3 antagonists
CN1250545C (en) 2000-12-28 2006-04-12 阿尔米雷尔普罗迪斯制药有限公司 Quinuclidine derivatives and their use as M3 antagonists
PL374384A1 (en) 2001-12-14 2005-10-17 Targacept, Inc. Methods and compositions for treatment of central nervous system disorders
IL162596A0 (en) * 2001-12-20 2005-11-20 S A L V A T Lab Sa 1-Alkyl-1-azoniabicyclo Ä2.2.2Ü octane carbamate derivatives and their use as muscarinic receptor ntagonists
ES2203327B1 (en) * 2002-06-21 2005-06-16 Almirall Prodesfarma, S.A. NEW QUINUCLIDINE CARBAMATES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
ES2204295B1 (en) 2002-07-02 2005-08-01 Almirall Prodesfarma, S.A. NEW DERIVATIVES OF QUINUCLIDINE-AMIDE.
AU2002345266B2 (en) 2002-07-08 2009-07-02 Ranbaxy Laboratories Limited 3,6-disubstituted azabicyclo [3.1.0]hexane derivatives useful as muscarinic receptor antagonists
TW200800953A (en) 2002-10-30 2008-01-01 Theravance Inc Intermediates for preparing substituted 4-amino-1-(pyridylmethyl) piperidine
PE20040950A1 (en) 2003-02-14 2005-01-01 Theravance Inc BIPHENYL DERIVATIVES AS AGONISTS OF ß2-ADRENERGIC RECEPTORS AND AS ANTAGONISTS OF MUSCARINAL RECEPTORS
US7517905B2 (en) 2003-04-09 2009-04-14 Ranbaxy Laboratories Limited Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists
BRPI0409302A (en) 2003-04-11 2006-04-11 Ranbaxy Lab Ltd azabicyclic derivatives as muscarinic receptor antagonists, method for their preparation and pharmaceutical composition containing them
TW200519106A (en) 2003-05-02 2005-06-16 Novartis Ag Organic compounds
ATE435862T1 (en) 2003-05-28 2009-07-15 Theravance Inc AZABICYCLOALKAN COMPOUNDS AS MUSCARINE RECEPTOR ANTAGONISTS
JP2007524641A (en) 2003-07-11 2007-08-30 セラヴァンス， インコーポレーテッド Substituted 4-amino-1-benzylpiperidine compounds
CN100569760C (en) 2003-11-21 2009-12-16 施万制药 Has β 2The active compound of 3 adrenergic receptor agonists and muscarinic receptor antagonist
GB0401334D0 (en) 2004-01-21 2004-02-25 Novartis Ag Organic compounds
JP2007528415A (en) 2004-03-11 2007-10-11 セラヴァンス， インコーポレーテッド Useful biphenyl compounds as muscarinic receptor antagonists
EP1723115A1 (en) 2004-03-11 2006-11-22 Theravance, Inc. Biphenyl compounds useful as muscarinic receptor antagonists
US7456199B2 (en) 2004-03-11 2008-11-25 Theravance, Inc. Biphenyl compounds useful as muscarinic receptor antagonists
TWI341836B (en) 2004-03-11 2011-05-11 Theravance Inc Biphenyl compounds useful as muscarinic receptor antagonists
JP2007528412A (en) 2004-03-11 2007-10-11 セラヴァンス， インコーポレーテッド Biphenyl compounds useful as muscarinic receptor antagonists
TW200538095A (en) 2004-03-11 2005-12-01 Theravance Inc Biphenyl compounds useful as muscarinic receptor antagonists
WO2005087739A1 (en) 2004-03-11 2005-09-22 Theravance, Inc. Biphenyl compounds useful as muscarinic receptor antagonists
JP2007528408A (en) 2004-03-11 2007-10-11 セラヴァンス， インコーポレーテッド Useful biphenyl compounds as muscarinic receptor antagonists
GB0411056D0 (en) 2004-05-18 2004-06-23 Novartis Ag Organic compounds
ES2246170B1 (en) * 2004-07-29 2007-04-01 Almirall Prodesfarma, S.A. NEW PROCEDURE TO PREPARE DERIVATIVES OF QUINUCLIDIN CARBAMATE.
GT200500281A (en) 2004-10-22 2006-04-24 Novartis Ag ORGANIC COMPOUNDS.
GB0424284D0 (en) 2004-11-02 2004-12-01 Novartis Ag Organic compounds
GB0426164D0 (en) 2004-11-29 2004-12-29 Novartis Ag Organic compounds
US7659403B2 (en) 2005-03-10 2010-02-09 Theravance, Inc. Biphenyl compounds useful as muscarinic receptor antagonists
EP1856112A1 (en) 2005-03-10 2007-11-21 Theravance, Inc. Biphenyl compounds useful as muscarinic receptor antagonists
WO2006099031A1 (en) 2005-03-10 2006-09-21 Theravance, Inc. Biphenyl compounds useful as muscarinic receptor antagonists
TW200714587A (en) 2005-03-10 2007-04-16 Theravance Inc Biphenyl compounds useful as muscarinic receptor antagonists
US7642355B2 (en) 2005-03-10 2010-01-05 Theravance, Inc. Biphenyl compounds useful as muscarinic receptor antagonists
GB0507577D0 (en) 2005-04-14 2005-05-18 Novartis Ag Organic compounds
GB0510390D0 (en) 2005-05-20 2005-06-29 Novartis Ag Organic compounds
JP2008546695A (en) 2005-06-13 2008-12-25 セラヴァンス， インコーポレーテッド Biphenyl compounds useful as muscarinic receptor antagonists
WO2007024814A1 (en) 2005-08-22 2007-03-01 Targacept, Inc. HETEROARYL-SUBSTiTUTED DIAZATRICYCLOALKANES, METHODS FOR ITS PREPARATION AND USE THEREOF
EP2532678A1 (en) 2005-10-21 2012-12-12 Novartis AG Human antibodies against il13 and therapeutic uses
US20090137623A1 (en) * 2005-12-30 2009-05-28 Naresh Kumar Muscarinic receptor antagonists
GB0601951D0 (en) 2006-01-31 2006-03-15 Novartis Ag Organic compounds
GB0602778D0 (en) 2006-02-10 2006-03-22 Glaxo Group Ltd Novel compound
PT2013211E (en) 2006-04-21 2012-06-21 Novartis Ag Purine derivatives for use as adenosin a2a receptor agonists
ES2298049B1 (en) 2006-07-21 2009-10-20 Laboratorios Almirall S.A. PROCEDURE FOR MANUFACTURING BROMIDE OF 3 (R) - (2-HIDROXI-2,2-DITIEN-2-ILACETOXI) -1- (3-PHENOXIPROPIL) -1-AZONIABICICLO (2.2.2) OCTANO.
EP1882691A1 (en) * 2006-07-26 2008-01-30 CHIESI FARMACEUTICI S.p.A. Quinuclidine derivatives as M3 antagonists
ATE502943T1 (en) 2006-09-29 2011-04-15 Novartis Ag PYRAZOLOPYRIMIDINES AS PI3K LIPID KINASE INHIBITORS
WO2008085608A1 (en) 2007-01-10 2008-07-17 Irm Llc Compounds and compositions as channel activating protease inhibitors
JP5293192B2 (en) 2007-02-09 2013-09-18 アステラス製薬株式会社 Aza-bridged ring compounds
US20090010923A1 (en) * 2007-04-24 2009-01-08 University Of Maryland, Baltimore Treatment of cancer with anti-muscarinic receptor agents
PL2155721T3 (en) 2007-05-07 2011-07-29 Novartis Ag Organic compounds
SA08290475B1 (en) 2007-08-02 2013-06-22 Targacept Inc (2S,3R)-N-(2-((3-Pyridinyl)Methyl)-1-Azabicyclo[2.2.2]Oct-3-yl)Benzofuran-2-Carboxamide, Novel Salt forms, and Methods of Use Thereof
WO2009046025A1 (en) 2007-10-01 2009-04-09 Comentis, Inc. Quinuclidin-4-ylmethyl 1h-indole-3-carboxylate derivatives as alpha 7 nicotinic acetylcholine receptor ligands for the treatment of alzheimer's disease
EP2065385A1 (en) * 2007-11-28 2009-06-03 Laboratorios SALVAT, S.A. Stable crystalline salt of (R)-3-fluorophenyl-3,4,5-trifluorobenzylcarbamic acid 1-azabiciyclo [2.2.2]oct-3-yl ester
CL2008003651A1 (en) 2007-12-10 2009-06-19 Novartis Ag Substituted 3,5-diamino-6-chloropyrazinamide derivative compounds; pharmaceutical composition; pharmaceutical combination; and use in the treatment of an inflammatory or allergic condition, in particular an inflammatory or obstructive disease of the airways.
PL2231642T3 (en) 2008-01-11 2014-04-30 Novartis Ag Pyrimidines as kinase inhibitors
EP2080507A1 (en) * 2008-01-15 2009-07-22 CHIESI FARMACEUTICI S.p.A. Pharmaceutical formulations comprising an anticholinergic drug
US20110059947A1 (en) 2008-02-13 2011-03-10 Targacept, Inc. Alpha 7 nicotinic agonists and antipsychotics
US20100055045A1 (en) 2008-02-26 2010-03-04 William Gerhart Method and system for the treatment of chronic obstructive pulmonary disease with nebulized anticholinergic administrations
GB2468073B (en) * 2008-02-26 2012-09-05 Elevation Pharmaceuticals Inc Method and system for the treatment of chronic obstructive pulmonary disease with nebulized anticholinergic administrations
EP2100599A1 (en) 2008-03-13 2009-09-16 Laboratorios Almirall, S.A. Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease
EP2100598A1 (en) 2008-03-13 2009-09-16 Laboratorios Almirall, S.A. Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease
US8268834B2 (en) 2008-03-19 2012-09-18 Novartis Ag Pyrazine derivatives that inhibit phosphatidylinositol 3-kinase enzyme
BRPI0915018A2 (en) 2008-06-10 2015-10-27 Novartis Ag organic compounds
EP2154136A1 (en) 2008-08-08 2010-02-17 CHIESI FARMACEUTICI S.p.A. Quinuclidine carbonate derivatives and medicinal compositions thereof
US20100112606A1 (en) * 2008-10-17 2010-05-06 Michael Armstrong Measurement and analysis of leukotrienes
EP2206712A1 (en) 2008-12-23 2010-07-14 CHIESI FARMACEUTICI S.p.A. "Alkaloid aminoester derivatives and medicinal composition thereof"
TW201031664A (en) 2009-01-26 2010-09-01 Targacept Inc Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide
US20110281917A1 (en) 2009-01-29 2011-11-17 Darrin Stuart Substituted Benzimidazoles for the Treatment of Astrocytomas
US8389526B2 (en) 2009-08-07 2013-03-05 Novartis Ag 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives
EA201200260A1 (en) 2009-08-12 2012-09-28 Новартис Аг HETEROCYCLIC HYDRAZONES AND THEIR APPLICATION FOR THE TREATMENT OF CANCER AND INFLAMMATION
MX2012002066A (en) 2009-08-17 2012-03-29 Intellikine Inc Heterocyclic compounds and uses thereof.
EA201200318A1 (en) 2009-08-20 2012-09-28 Новартис Аг Heterocyclic oximes
AU2010310449A1 (en) 2009-10-22 2012-05-03 Vertex Pharmaceuticals Incorporated Compositions for treatment of cystic fibrosis and other chronic diseases
US8247436B2 (en) 2010-03-19 2012-08-21 Novartis Ag Pyridine and pyrazine derivative for the treatment of CF
EP2585458B1 (en) * 2010-06-22 2015-01-07 Chiesi Farmaceutici S.p.A. Alkaloid aminoester derivatives and medicinal compositions thereof
EP2585457B1 (en) * 2010-06-22 2015-07-22 Chiesi Farmaceutici S.p.A. Alkaloid aminoester derivatives and medicinal composition thereof
RU2580835C2 (en) * 2010-06-22 2016-04-10 КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. Alkaloid derivatives based on aminoesters and compositions of medications containing them
CN102946868B (en) 2010-06-22 2014-10-29 奇斯药制品公司 Dry powder formulation comprising an antimuscarinic drug
US8637516B2 (en) 2010-09-09 2014-01-28 Irm Llc Compounds and compositions as TRK inhibitors
WO2012034095A1 (en) 2010-09-09 2012-03-15 Irm Llc Compounds and compositions as trk inhibitors
US8372845B2 (en) 2010-09-17 2013-02-12 Novartis Ag Pyrazine derivatives as enac blockers
KR20130141534A (en) 2010-11-26 2013-12-26 키에시 파르마슈티시 엣스. 피. 에이. Glycine derivatives and their use as muscarinic receptor antagonists
KR101928505B1 (en) * 2011-01-28 2018-12-12 에스케이바이오팜 주식회사 Pharmaceutical composition comprising pyridone derivatives
WO2012107500A1 (en) 2011-02-10 2012-08-16 Novartis Ag [1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase
US20120220557A1 (en) 2011-02-17 2012-08-30 Chiesi Farmaceutici S.P.A. Liquid propellant-free formulation comprising an antimuscarinic drug
US9127000B2 (en) 2011-02-23 2015-09-08 Intellikine, LLC. Heterocyclic compounds and uses thereof
CA2828219A1 (en) 2011-02-25 2012-08-30 Irm Llc Pyrazolo [1,5-a] pyridines as trk inhibitors
PT2685986T (en) * 2011-03-18 2020-03-05 Genzyme Corp Glucosylceramide synthase inhibitors
EP2510928A1 (en) 2011-04-15 2012-10-17 Almirall, S.A. Aclidinium for use in improving the quality of sleep in respiratory patients
EP2702041A1 (en) 2011-04-29 2014-03-05 Chiesi Farmaceutici S.p.A. Alkaloid ester and carbamate derivatives and medicinal compositions thereof
UY34305A (en) 2011-09-01 2013-04-30 Novartis Ag DERIVATIVES OF BICYCLIC HETEROCICLES FOR THE TREATMENT OF PULMONARY ARTERIAL HYPERTENSION
MX339302B (en) 2011-09-15 2016-05-19 Novartis Ag 6 - substituted 3 - (quinolin- 6 - ylthio) - [1,2,4] triazolo [4, 3 -a] pyradines as tyrosine kinase.
WO2013038381A1 (en) 2011-09-16 2013-03-21 Novartis Ag Pyridine/pyrazine amide derivatives
WO2013038390A1 (en) 2011-09-16 2013-03-21 Novartis Ag N-substituted heterocyclyl carboxamides
WO2013038378A1 (en) 2011-09-16 2013-03-21 Novartis Ag Pyridine amide derivatives
WO2013038373A1 (en) 2011-09-16 2013-03-21 Novartis Ag Pyridine amide derivatives
WO2013038386A1 (en) 2011-09-16 2013-03-21 Novartis Ag Heterocyclic compounds for the treatment of cystic fibrosis
WO2013078440A2 (en) 2011-11-23 2013-05-30 Intellikine, Llc Enhanced treatment regimens using mtor inhibitors
CA2862008A1 (en) 2011-12-30 2013-07-04 Chiesi Farmaceutici S.P.A. Quinuclidine esters of 1-azaheterocyclylacetic acid as antimuscarinic agents, process for their preparation and medicinal compositions thereof
US8809340B2 (en) 2012-03-19 2014-08-19 Novartis Ag Crystalline form
WO2013149581A1 (en) 2012-04-03 2013-10-10 Novartis Ag Combination products with tyrosine kinase inhibitors and their use
US9073921B2 (en) 2013-03-01 2015-07-07 Novartis Ag Salt forms of bicyclic heterocyclic derivatives
WO2014151147A1 (en) 2013-03-15 2014-09-25 Intellikine, Llc Combination of kinase inhibitors and uses thereof
WO2015084804A1 (en) 2013-12-03 2015-06-11 Novartis Ag Combination of mdm2 inhibitor and braf inhibitor and their use
CA2945257A1 (en) 2014-04-24 2015-10-29 Novartis Ag Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors
BR112016024484A2 (en) 2014-04-24 2017-08-15 Novartis Ag aminopyridine derivatives as phosphatidylinositol 3-kinase inhibitors
EA032075B1 (en) 2014-04-24 2019-04-30 Новартис Аг Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors
WO2016007630A1 (en) 2014-07-11 2016-01-14 Alpharmagen, Llc Quinuclidine compounds for modulating alpha7 -nicotinic acetylcholine receptor activity
WO2016011658A1 (en) 2014-07-25 2016-01-28 Novartis Ag Combination therapy
RU2695230C2 (en) 2014-07-31 2019-07-22 Новартис Аг Combined therapy
US9724340B2 (en) 2015-07-31 2017-08-08 Attenua, Inc. Antitussive compositions and methods
CN113891744A (en) 2019-06-10 2022-01-04 诺华股份有限公司 Pyridine and pyrazine derivatives for the treatment of CF, COPD and bronchiectasis
EP4021572A1 (en) 2019-08-28 2022-07-06 Novartis AG Substituted 1,3-phenyl heteroaryl derivatives and their use in the treatment of disease
TW202140550A (en) 2020-01-29 2021-11-01 瑞士商諾華公司 Methods of treating an inflammatory or obstructive airway disease using anti-tslp antibody
AU2021311131A1 (en) 2020-07-24 2023-03-23 Genzyme Corporation Pharmaceutical compositions comprising venglustat

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2762796A (en) * 1956-09-11 Iminodibenzyl derivative
GB1219606A (en) 1968-07-15 1971-01-20 Rech S Et D Applic Scient Soge Quinuclidinol derivatives and preparation thereof
GB1246606A (en) 1969-04-28 1971-09-15 Starogardzkie Zakl Farma Dibenzo-azepine derivatives
IL72788A (en) * 1984-08-28 1989-07-31 Israel State Bis quaternary oxy-bis methylene(or trimethylene)bis-n-quinuclidines,pyridines and piperidines,their preparation and antidotes against organophosphorus and carbamate poisoning containing them
GB2225574B (en) * 1987-12-24 1991-04-24 Wyeth John & Brother Ltd Heterocyclic compounds
US5066680A (en) * 1989-02-14 1991-11-19 Fujisawa Pharmaceutical Co., Ltd. Novel substituted-acetamide compound and a process for the preparation thereof
GB8923590D0 (en) 1989-10-19 1989-12-06 Pfizer Ltd Antimuscarinic bronchodilators
GB9119705D0 (en) 1991-09-14 1991-10-30 Pfizer Ltd Therapeutic compounds
GB9201751D0 (en) 1992-01-28 1992-03-11 Smithkline Beecham Plc Compounds
GB9202443D0 (en) 1992-02-05 1992-03-18 Fujisawa Pharmaceutical Co A novel substituted-acetamide compound and a process for the preparation thereof
CN1140447A (en) * 1994-02-10 1997-01-15 山之内制药株式会社 Novel carbamate deriv. and medicinal composition contg. the same
KR970701174A (en) * 1994-02-10 1997-03-17 오노다 마사요시 Novel carbamate derivative and medicinal composition containing the same
NO2005012I1 (en) * 1994-12-28 2005-06-06 Debio Rech Pharma Sa Triptorelin and pharmaceutically acceptable salts thereof
JPH08198751A (en) * 1995-01-19 1996-08-06 Yamanouchi Pharmaceut Co Ltd Carbamate derivative
WO1997013766A1 (en) 1995-10-13 1997-04-17 Banyu Pharmaceutical Co., Ltd. Substituted heteroaromatic derivatives
AUPN862996A0 (en) 1996-03-13 1996-04-04 Fujisawa Pharmaceutical Co., Ltd. A novel substituted-acetamide compound
PE92198A1 (en) 1996-08-01 1999-01-09 Banyu Pharma Co Ltd DERIVATIVES OF FLUORINE-CONTAINED 1,4-PIPERIDINE
ES2165768B1 (en) * 1999-07-14 2003-04-01 Almirall Prodesfarma Sa NEW DERIVATIVES OF QUINUCLIDINE AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM.
KR100751981B1 (en) * 2000-06-27 2007-08-28 라보라토리오스 살바트, 에스.에이. Carbamates derived from arylalkylamines
CA2441896A1 (en) 2000-12-22 2002-07-04 Almirall Prodesfarma Ag Quinuclidine carbamate derivatives and their use as m3 antagonists
CN1250545C (en) 2000-12-28 2006-04-12 阿尔米雷尔普罗迪斯制药有限公司 Quinuclidine derivatives and their use as M3 antagonists
IL162596A0 (en) 2001-12-20 2005-11-20 S A L V A T Lab Sa 1-Alkyl-1-azoniabicyclo Ä2.2.2Ü octane carbamate derivatives and their use as muscarinic receptor ntagonists
ES2203327B1 (en) 2002-06-21 2005-06-16 Almirall Prodesfarma, S.A. NEW QUINUCLIDINE CARBAMATES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
ES2204295B1 (en) 2002-07-02 2005-08-01 Almirall Prodesfarma, S.A. NEW DERIVATIVES OF QUINUCLIDINE-AMIDE.
US6946828B1 (en) * 2003-05-20 2005-09-20 Ami Semiconductor, Inc. Bi-directional current measurement circuit that uses a transconductance amplifier to generate a copy current
ES2246170B1 (en) 2004-07-29 2007-04-01 Almirall Prodesfarma, S.A. NEW PROCEDURE TO PREPARE DERIVATIVES OF QUINUCLIDIN CARBAMATE.
WO2006060346A2 (en) 2004-12-03 2006-06-08 Merck & Co., Inc. 8-phenyl-5,6,7,8-hydroquinoline tachykinin receptor antagonists
EP1882691A1 (en) 2006-07-26 2008-01-30 CHIESI FARMACEUTICI S.p.A. Quinuclidine derivatives as M3 antagonists
EP2065385A1 (en) 2007-11-28 2009-06-03 Laboratorios SALVAT, S.A. Stable crystalline salt of (R)-3-fluorophenyl-3,4,5-trifluorobenzylcarbamic acid 1-azabiciyclo [2.2.2]oct-3-yl ester
EP2080523A1 (en) 2008-01-15 2009-07-22 CHIESI FARMACEUTICI S.p.A. Compositions comprising an antimuscarinic and a long-acting beta-agonist

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2456286C2 (en) * 2006-11-14 2012-07-20 Астразенека Аб Quinuclidine derivatives of (hetero) arylcycloheptane carboxylic acids as muscarine receptor antagonists

Similar Documents

Publication Publication Date Title
RU2003122341A (en) NEW Quinuclidine Carbamate Derivatives and Drug Compositions Containing Named Derivatives
RU2321588C2 (en) Carbamate derivatives of quinuclidine, pharmaceutical composition based on thereof and using
RU2002103605A (en) Quinuclidine derivatives and their use as ligands of the muscarinic receptor MH
RU2003123120A (en) NEW DERIVATIVES OF HINUCLIDINE AND THEIR MEDICINAL COMPOSITIONS
KR100869722B1 (en) Quinuclidine carbamate derivatives and their use as m3 antagonists
KR100773844B1 (en) Quinuclidine derivatives and their use as muscarinic m3 receptor ligands
JP2005533826A5 (en)
AU2003242757B2 (en) New quinuclidine amide derivatives
JP2005533799A5 (en)
PL211250B1 (en) 1-alkyl-1-azoniabicyclo (2.2.2) octane carbamate derivatives and their use as muscarinic receptor antagonists
KR910009699A (en) New Tricyclic Compounds
RU2005104435A (en) DERIVATIVES OF 1-HETEROCYCLYLalkyl-3-SULFONILAZINDOL OR - AZAINDAZOLE AS 5-HYDROXYTRIPTAMINE-6 LIGANDS
JP2006504766A5 (en)
JP2002506047A (en) An analgesic composition comprising an NMDA receptor antagonist and a narcotic analgesic.
RU2004133371A (en) NEW PYRROLIDINIA DERIVATIVES
RU2138261C1 (en) Use of 2-phenyl-3-aroylbenzothiophenes for inhibition of central nervous system disorder in women in postmenopause
RU2006104851A (en) MUSCARINE ACETYLCHOLINE RECEPTOR ANTAGONISTS
US5340826A (en) Pharmaceutical agents for treatment of urinary incontinence
AU700520B2 (en) NK-1 receptor antagonists for the treatment of cancer
CA2136801C (en) Pharmaceutical agents for the treatment of disorders caused by helicobacter pylori or other spiral urease-positive gram-negative bacteria
AU2004206846A1 (en) Quaternary antimuscarinic compounds for the treatment of bladder diseases
CZ378597A3 (en) Application of pyrrolidine derivatives for treating alcoholism
EP0439320A1 (en) Erectile dysfunction treatment
KR101063605B1 (en) Schizophrenia Treatment
JP2002520364A (en) Method of treatment