# US 2014/0155427 A1 · Novel compounds

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0155427 A1
- Document ID: US20140155427A1
- Status: Published application
- Kind: A1
- Application number: 14/097,586
- Filed: 2013-12-05
- Published: 2014-06-05
- Earliest claimed: 2012-12-05
- Assignees: Chiesi Farmaceutici S.p.A.
- Applicants: CHIESI FARMACEUTICI S.p.A.
- Inventors: Elisabetta Armani; Gabriele Amari; Mauro Riccaboni; Andrea Rizzi; Charles Baker-Glenn; Wesley Blackaby; Herve' Van de Poel; Ben Whittaker
- Web page: https://patentgrep.com/patent/US20140155427A1

## CPC

- C07D 453/02: containing not further condensed quinuclidine ring systems
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 11/08: Bronchodilators
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 453/00: Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- A61K 9/0075: {for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles}
- A61K 31/439: the ring forming part of a bridged ring system, e.g. quinuclidine (8-azabicyclo [3.2.1] octanes A61K31/46)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

Compounds of formula (I) described herein are inhibitors of the phosphodiesterase 4 (PDE4) enzyme and muscarinic M3 receptor antagonists and are useful for the prevention and/or treatment of diseases of the respiratory tract characterized by airway obstruction.

## Claims

### Claim 1

A compound represented by formula (I):
wherein
W is aryl or heteroaryl;
each R1 is independently hydrogen, halogen, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) haloalkyl, hydroxy, —SO2NR6R7, —CN, —NR8SO2R9, —NR6R7, —CONR6R7, or —NR8COR9, and wherein said (C1-C4) alkyl is optionally substituted by one or more groups selected from the group consisting of (C3-C7) cycloalkyl, hydroxyl, and —NR6R7 and said (C1-C4) alkoxy is optionally substituted by one or more halogen atoms or (C3-C7) cycloalkyl groups, and
wherein,
R6 is hydrogen or (C1-C6) alkyl;
R7 is hydrogen or (C1-C6) alkyl;
R8 is hydrogen or (C1-C6) alkyl;
R9 is hydrogen or (C1-C6) alkyl;
n is an integer ranging from 1 to 3;
each R2 is independently hydrogen, halogen, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4)haloalkyl, hydroxy, —SO2NR10R11, —CN, or —NR12SO2R13, and wherein said (C1-C4) alkyl and (C1-C4) alkoxy are optionally substituted by one (C3-C7) cycloalkyl group,
R10 is hydrogen or (C1-C6) alkyl;
R11 is hydrogen or (C1-C6) alkyl;
R12 is hydrogen or (C1-C6) alkyl;
R13 is hydrogen or (C1-C6) alkyl;
m is an integer ranging from 1 to 3;
p is zero or 1;
L1 is a group (CH2)t wherein t is 0 or an integer ranging from 1 to 3;
L2 is:
(CH2)q wherein q is an integer ranging from 1 to 3,
divalent ortho-benzyl (o-C6H4—CH2—),
divalent meta-benzyl (m-C6H4—CH2—),
divalent para-benzyl (p-C6H4—CH2—),
divalent ortho-methyleneoxy-benzyl (o-CH2—O—C6H4—CH2—),
divalent meta-methyleneoxy-benzyl (m-CH2—O—C6H4—CH2—), or
divalent para-methylenoxy-benzyl (p-CH2—O—C6H4—CH2—), wherein the carbon chain atom of the benzyl group is linked to the nitrogen atom and the respective aromatic carbon atom or the methylene carbon atom of the methylene oxy group is linked to the phenyl group;
R3 and R4 are different or the same and are each independently:
H;
(C3-C7) cycloalkylcarbonyl;
(C1-C6) alkyl, optionally substituted by one or more substituents selected from (C3-C7) cycloalkyl or (C5-C7) cycloalkenyl;
(C1-C6) haloalkyl;
(C3-C7) cycloalkyl;
(C5-C7) cycloalkenyl;
(C2-C6) alkenyl; or
(C2-C6) alkynyl;
or R3 and R4, together with the interconnecting atoms, form a 2,2-difluoro-1,3-dioxolane ring of formula (r) fused to the phenyl moiety which bears groups —OR3 and —OR4, wherein asterisks indicate carbon atoms shared with the phenyl ring:
each R5 is independently CN, NO2, CF3 or a halogen atom;
k is an integer ranging from 1 to 3; and
A is a nitrogen containing group which may be:
a group (a) which is —(CH2)s—NR14R15 wherein s is an integer ranging from 1 to 4 and R14 and R15 are independently hydrogen or (C1-C4) alkyl; or
a group (b) which is a saturated monocyclic, bicyclic, or tricyclic heterocyclic ring system optionally substituted by one or two groups R16 which are at each occurrence independently (C1-C4) alkyl or benzyl;
an N-oxide on the pyridine ring, deuterated derivative, or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound, N-oxide, deuterated derivative, or a pharmaceutically acceptable salt according to claim 1, which is represented by formula (IB):

### Claim 3 (depends on 1)

A compound, N-oxide, deuterated derivative, or a pharmaceutically acceptable salt according to claim 1, which is represented by the formula (ID):

### Claim 4 (depends on 1)

A compound N-oxide, deuterated derivative, or a pharmaceutically acceptable salt according to claim 1, which is represented by formula (IA):

### Claim 5 (depends on 1)

A compound, N-oxide, deuterated derivative, or a pharmaceutically acceptable salt according to claim 1, which is represented by formula (IE):
wherein L2 and L1 are located in the ortho, meta or para position on the phenyl ring they are linked to;
L1 is selected from a group (CH2)t wherein t is 0 or an integer ranging from 1 to 3; and
L2 is:
(CH2)q wherein q is an integer ranging from 1 to 3,
divalent meta-benzyl (m-C6H4—CH2—),
divalent para-benzyl (p-C6H4—CH2—),
divalent meta-methyleneoxy-benzyl (m-CH2—O—C6H4—CH2—), or
divalent para-methylenoxy-benzyl (p-CH2—O—C6H4—CH2—), wherein the carbon chain atom of the benzyl group is linked to the nitrogen atom and the respective aromatic carbon atom or the methylene carbon atom of the methylene oxy group is linked to the phenyl group.

### Claim 6 (depends on 1)

A compound, N-oxide, deuterated derivative, or a pharmaceutically acceptable salt according to claim 1, which has the absolute configuration of carbon (1) shown in formula (I)′:

### Claim 7 (depends on 1)

A compound, N-oxide, deuterated derivative, or a pharmaceutically acceptable salt according to claim 1 which is a compound selected from the group consisting of:
(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(4-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(3-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(3-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(4-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(4-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(3-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-methyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]benzoate;
[(1R)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(3-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1R)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(3-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(4-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1R)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(4-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-bromo-5-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[4-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]phenyl]acetate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]2-[4-[(N-[(3R)-quinuclidyl]oxycarbonylanilino)methyl]phenyl]acetate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]phenyl]acetate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(3-chloro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2,3-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2,5-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(3-methyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[[N-[(3R)-quinuclidin-3-yl]oxycarbonyl-3-(trifluoromethyl)anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-methyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(3-cyano-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-methoxy-phenyl]ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-isopropoxy-phenyl]ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-ethoxy-phenyl]ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-methoxy-phenyl]ethyl]3-[(3-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-isopropoxy-phenyl]ethyl]3-[(3-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-ethoxy-phenyl]ethyl]3-[(3-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-methoxy-phenyl]ethyl]4-[(2-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-isopropoxy-phenyl]ethyl]4-[(2-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-ethoxy-phenyl]ethyl]4-[(2-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2,3-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2,4-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2,5-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2,5-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(3-methyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(3-methyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(3-cyano-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-fluoro-4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-fluoro-4-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-fluoro-5-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-fluoro-4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-(trideuteriomethoxy)phenyl]ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-(trideuteriomethoxy)phenyl]ethyl]3-[(3-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-(trideuteriomethoxy)phenyl]ethyl]4-[(2-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[2-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[2-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-1-[3-(cyclopentoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3-(cyclopentoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[[3-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]phenoxy]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[3-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]phenoxy]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[[4-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]phenoxy]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[4-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]phenoxy]methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-isopropoxy-phenyl]ethyl]4-[[2-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-(trideuteriomethoxy)phenyl]ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-methoxy-phenyl]ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-ethoxy-phenyl]ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-isopropoxy-phenyl]ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-fluoro-5-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[2-(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)ethyl]benzoate;
[2-(3,5-dichloro-4-pyridyl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[2-(3,5-dichloro-4-pyridyl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]-5-methyl-benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]2-[3-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]phenyl]acetate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]phenyl]acetate;
[(1R)-1-[3-(cyclopropylmethoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1R)-1-[3,4-bis(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3,4-bis(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1R)-1-[3,4-bis(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3,4-bis(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1R)-1-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1R)-1-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1R)-1-[3-(cyclopropylmethoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1R)-1-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[2-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-1-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[2-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-1-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1R)-1-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1R)-1-[3-(cyclopropylmethoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[2-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1R)-1-[3-(cyclopropylmethoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[2-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-chloro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2,4-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-fluoro-3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-fluoro-3-[(N-[(3R)-quinuclidin-3-yl]oxycarbonylanilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-fluoro-4-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[2-(difluoromethoxy)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-fluoro-6-methoxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(3-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[(5-fluoro-3-pyridyl)-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[(4-fluoro-2-pyridyl)-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[3-(dimethylcarbamoyl)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[(2-methoxy-3-pyridyl)-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[(5-methoxy-3-pyridyl)-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[(6-hydroxy-3-pyridyl)-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-cyano-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-isopropoxy-phenyl]ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[1-[3-(cyclopropylmethoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[1-[3-(cyclopentoxy)-4-methoxy-phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]phenyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]phenyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]phenyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]phenyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[[(3R)-quinuclidin-3-yl]oxycarbonyl-thiazol-2-yl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[1H-indazol-7-yl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[1H-indazol-7-yl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[1H-indol-7-yl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]4-[(2-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(2-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[3-(difluoromethyl)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(3-fluoro-5-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-methoxy-3-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-methyl-3-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-chloro-5-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-fluoro-5-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(5-hydroxy-2-methyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-chloro-3-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-Dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(3-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2,6-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(3-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[[2-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-chloro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2,6-difluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[[3-pyridyl-[(3R)-quinuclidin-3-yl]oxycarbonyl-amino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-fluoro-4-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(4-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[[4-(methanesulfonamido)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(3-tert-butyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-propoxy-phenyl]ethyl]4-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-[4-(difluoromethoxy)-3-propoxy-phenyl]ethyl]4-[(3-pyridyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[[3-(methanesulfonamido)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[4-(methanesulfonamido)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[2-(cyclopropylmethoxy)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[2-(cyclopropylmethoxy)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-fluoro-6-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[3-(hydroxymethyl)-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino]methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2-carbamoyl-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2,3-dihydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[(2,3-dihydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]4-[[[(3R)-quinuclidin-3-yl]oxycarbonyl-(1H-tetrazol-5-yl)amino]methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(2-fluoro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate;
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]3-[(N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate; and
[(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)ethyl]2-hydroxy-3-[(2-hydroxy-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate
or a pharmaceutically acceptable salt of said compound.

### Claim 8 (depends on 1)

A pharmaceutical composition, comprising a compound, N-oxide, deuterated derivative, or a pharmaceutically acceptable salt according to claim 1 and one or more pharmaceutically acceptable carriers.

### Claim 9 (depends on 8)

A pharmaceutical composition according to claim 8, further comprising another active ingredient.

### Claim 10 (depends on 1)

A method for the prevention and/or treatment of a disease of the respiratory tract characterized by airway obstruction, comprising administering an effective amount of a compound, N-oxide, deuterated derivative, or a pharmaceutically acceptable salt according to claim 1 to a subject in need thereof.

### Claim 11 (depends on 10)

A method according to claim 10, wherein said disease of the respiratory tract is asthma or COPD.

### Claim 12 (depends on 8)

An inhalation device comprising a pharmaceutical composition according to claim 8.

### Claim 13 (depends on 8)

A kit, comprising a pharmaceutical composition according to claim 8 and a device which is a single- or multi-dose dry powder inhaler, a metered dose inhaler, or a nebulizer.