Novel derivatives having 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or pharmaceutically acceptable salt thereof and pharmaceutical compositions comprising the same

Abstract

The present invention provides a novel compound having a 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or a pharmaceutically acceptable salt thereof, a method for preparing the same, a pharmaceutical composition containing the same, and uses thereof. The compound having a 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or a pharmaceutically acceptable salt thereof has inhibitory activity against glucosylceramide synthase (GCS), and thus can be usefully used for the treatment and prevention of various GCS-mediated diseases, such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease.

Description

Technology Field

[0001] The present invention relates to novel compounds having inhibitory activity against glucosylceramide synthase (GCS), namely derivatives having a 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or pharmaceutically acceptable salts thereof, methods for preparing the same, pharmaceutical compositions containing the same, and uses thereof. Background Technology

[0002] Lysosomal storage disorders (LSDs) are metabolic diseases characterized by various pathological symptoms throughout the body, resulting from the genetic deficiency or lack of specific enzymes within lysosomes, which prevent the breakdown of substrates that need to be metabolized and cause them to accumulate. Currently, about 50 types of LSDs are known, and they are broadly classified into diseases such as mucopolysaccharidosis, oligosaccharidosis, and sphingolipidoses, depending on the substances that accumulate.

[0003] Sphingolipidosis is a glycolipid storage disease in which enzymes involved in sphingolipid metabolism, such as beta-glucosidase and alpha-galactosidase, do not show normal activity, leading to the accumulation of their substrates, such as glucosylceramide and trihexosylceramide, and the resulting pathology; Gaucher disease and Fabry disease belong to this category.

[0004] There are two main treatments for these lysosomal storage diseases. The first method involves replacing or supplementing the deficient or missing metabolic enzymes. While this enzyme replacement therapy (ERT) is safe and effective, it requires periodic intravenous administration of the relevant enzymes, dosage adjustments based on the response, and is costly. In particular, it is often ineffective in treating neurological symptoms because it is difficult to distribute the enzymes to the nervous system, and there is a problem with the frequent formation of autoantibodies against the administered enzymes.

[0005] The second method is substrate reduction therapy (SRT), which inhibits the synthesis of accumulating substrates. Glucosylceramide synthase (GCS; UDP-glucose: ceramide glycosyltransferase, UDP-glucose: N-acylsphingosine D-glucosyltransferase, EC 2.4.1.80) is an enzyme involved in sphingolipid metabolism and is involved in the reaction in which ceramide combines with glucose to produce glucosylceramide. The produced glucosylceramide is converted into various GSLs. Glucosylceramide synthase (GCS) inhibitors inhibit the activity of GCS, thereby reducing the body's production of glucosylceramide and preventing the abnormal accumulation of related glycolipids, such as trihexosylceramide, GM1, and GM2, in cells or organs.

[0006] As such, GCS inhibitors inhibit GCS activity and prevent the accumulation of glycosphingolipids; thereby, they can be usefully employed in the treatment of lysosomal storage diseases, particularly glycosphingolipid storage diseases, such as GM1 gangliosidosis, Tay-Sachs disease, Sandhoff disease, Gaucher disease, Fabry disease, Niemann-Pick A and B diseases, metachromatic leukodystrophy, and Krabbe disease. Additionally, they can be usefully employed in the treatment of diseases that occur secondarily due to glycosphingolipid storage, such as Niemann-Pick C disease, mucopolysaccharidosis, and mucolipidosis type IV (Chen CS, et al., Abnormal transport along the lysosomal pathway in mucolipidosis, type IV disease). Proc Natl Acad Sci USA . 1998 May 26;95(11):6373-8; and Goodman LA, et al., Ectopic dendrites occur only on cortical pyramidal cells containing elevated GM2 ganglioside in alpha-mannosidosis, Proc Natl Acad Sci US A.1991 Dec 15;88(24):11330-4). In addition, it has been reported to be useful in the treatment of diseases involving glycosylceramide accumulation, e.g., renal hypertrophy (e.g., diabetic nephropathy), hyperglycemia or hyperinsulinemia; cancers in which glycosylceramide synthesis is abnormal; infectious diseases caused by organisms that use cell surface glycosylceramides as receptors; infectious diseases in which the synthesis of glucosylceramide is essential or important; diseases in which excessive glycosylceramide synthesis occurs (e.g., atherosclerosis, polycystic kidney disease, and renal hypertrophy); neurological disorders and neurological damage related to the replenishment and activation of macrophages (e.g., Alzheimer's disease, epilepsy, stroke, spinal cord disease, Parkinson's disease, etc.) and inflammatory diseases or conditions (e.g., rheumatoid arthritis, Crohn's disease, asthma, sepsis); and diabetes and obesity (WO 2006 / 053043). In addition, overexpression of GCS interferes with ceramide-induced apoptosis (Liu YY, et al., Uncoupling ceramide glycosylation by transfection of glucosylceramide synthase antisense reverses adriamycin resistance, J Biol Chem. 2000 Mar 10;275(10):7138-43). Therefore, GCS inhibitors can be useful for treating proliferative diseases such as cancer by inducing apoptosis in diseased cells.

[0007] Various studies have been conducted to develop GCS inhibitors, and for example, WO 2005 / 068426, WO 2006 / 053043, WO 2008 / 150486, WO 2009 / 117150, WO 2010 / 014554, WO 2014 / 043068 have disclosed various compounds having GCS inhibitory activity. The problem to be solved

[0008] The inventors have discovered that derivatives having a 5,6-fusion bicyclic moiety, namely 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety, or pharmaceutically acceptable salts thereof, have excellent inhibitory activity against GCS. Accordingly, derivatives having the 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or pharmaceutically acceptable salts thereof can be usefully employed in the treatment and prevention of various diseases mediated by glucosylceramide synthase (GCS), such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease.

[0009] Accordingly, the present invention aims to provide a derivative having the 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or a pharmaceutically acceptable salt thereof, a method for preparing the same, a pharmaceutical composition comprising the same, and uses thereof. means of solving the problem

[0010] According to one aspect of the present invention, a derivative having a 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or a pharmaceutically acceptable salt thereof is provided.

[0011] According to another aspect of the present invention, a method for preparing a derivative having the 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or a pharmaceutically acceptable salt thereof is provided.

[0012] According to another aspect of the present invention, a pharmaceutical composition is provided comprising, as an active ingredient, a derivative having the 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or a pharmaceutically acceptable salt thereof.

[0013] According to another aspect of the present invention, a therapeutic method is provided comprising administering a derivative having the 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or a pharmaceutically acceptable salt thereof.

[0014] According to another aspect of the present invention, the use of a derivative having the 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety or a pharmaceutically acceptable salt thereof is provided for use in the manufacture of a drug for inhibiting glucosylceramide synthase. Effects of the invention

[0015] It has been revealed by the present invention that derivatives having a 5,6-fusion bicyclic moiety, namely 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety, or pharmaceutically acceptable salts thereof, have excellent inhibitory activity against glucosylceramide synthase. Accordingly, compounds according to the present invention or pharmaceutically acceptable salts thereof can be usefully applied to the treatment and prevention of various diseases mediated by glucosylceramide synthase, such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease. Specific details for implementing the invention

[0016] In this specification, the term 'alkyl' refers to an aliphatic hydrocarbon radical and includes both straight-chain and branched hydrocarbon radicals. For example, C1-C6 alkyls are aliphatic hydrocarbons having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, n -Butyl, n -pentyl, n - Hexyl, isopropyl, isobutyl, sec -Butyl, tert - Includes butyl, neopentyl, isopentyl, etc.

[0017] In addition, the term 'hydroxy' is defined as -OH, and the term 'alkoxy' refers to a radical in which a hydrogen atom of the hydroxyl group is substituted with an alkyl group, unless otherwise defined. For example, C1–C6 alkoxys include methoxy, ethoxy, propoxy, n - Beautoxy, n -Pentyloxy, isopropoxy, sec - Beautoxy, tert - Includes butoxy, neopentyloxy, isopentyloxy, etc.

[0018] In addition, the term 'halogen' means fluorine, bromine, chlorine, or iodine.

[0019] Additionally, the term 'cycloalkyl' means a saturated aliphatic 3 to 10-membered ring, preferably 3 to 7-membered ring, unless otherwise defined. Typical cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.

[0020] Additionally, the term 'aryl' refers to an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, comprising a single or multiple fused ring system containing, suitably, 5 to 14 substituted or unsubstituted ring atoms in each ring, and including forms in which multiple aryls are connected by single bonds. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.

[0021] Additionally, the term 'heteroaryl' refers to a 5 to 12-membered aromatic radical containing 1 to 3 heteroatoms selected from the group consisting of N, O, and S atoms, and includes a 5 to 6-membered monocyclic heteroaryl radical and a bicyclic heteroaryl radical formed by fusing with a benzene ring or a pyridine ring. Additionally, the term 'heterocycle' refers to a 3 to 12-membered mono- or poly-cyclic ring containing one or more heteroatoms O, N, or S, preferably 1 to 4 identical or different heteroatoms, and does not include an aromatic ring. Non-limiting examples of heteroaryl rings or heterocyclic rings include oxetane, pyrrolidine, pyrrole, tetrahydrofuran, furan, tetrahydrothiophene, thiophene, imidazolidine, imidazole, pyrazolidine, pyrazol, pyrrolizine, oxazolidine, oxazole, isoxazolidine, isoxazole, thiazolidine, thiazole, isothiazolidine, isothiazol, dioxolane, dithiolan, oxadiazole, thiadiazole, dithiazole, tetrazole, oxatercole, thiatercole, piperidine, pyridine, pyrimidine, tetrahydropyran, pyran, thian, thiopyran, piperazine, diazine, morpholain, oxazine, dioxane, indole, indoline, benzodioxol, benzothiophene, benzofuran, benzimidazole, Examples include benzoxazole, benzisoxazole, benzothiaazole, benzothiadiazole, benzotriazole, quinoline, isoquinoline, purine, furopyridine, mono- or di-azabicyclo, e.g., quinuclidene, diazabicycloheptane, monoazabicyclooctane, diazspirondecan, hexahydropyrrolopyrrole, pyrrolopyrrole, pyrrolopyridine, imidazopyridazine, dihydrobenzodioxin, dihydrobenzofuran, etc., but are not limited to these.

[0022] Additionally, the term 'amino' is defined as -NH2, and the term 'alkylamino' means an amino substituted with a mono- or di-alkyl group. For example, C1–C6 alkylaminos include aminos substituted with a mono- or di-C1–C6 alkyl group.

[0023] In addition, the term 'alkylthio' is defined as -SR (where R is alkyl), and the term 'cyano' is defined as -CN.

[0024] The present invention provides a derivative having a 5,6-fusion bicyclic moiety, namely a 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety, or a pharmaceutically acceptable salt thereof, namely a compound of Formula 1 below or a pharmaceutically acceptable salt thereof:

[0025] <Chemical Formula 1>

[0026]

[0027] During the meal,

[0028] L is -O-, -CO-, -CR1R2-, or -NR3-, and

[0029] Y and Z are, independently of each other, -CR1R2-; -NR3-; -O-; or -S-, and

[0030] R1 and R2 are, independently of each other, hydrogen; halogen; C1–C6 alkyl; C1–C6 alkyl having a nitrogen, oxygen, or sulfur atom; C3–C 10 Cycloalkyl; ternary to twelve-membered heterocyclic; or C1 to C6 alkoxy; or R1 and R2 together with the carbon atom to which they are bonded are C3 to C 10 Forming a cycloalkyl group,

[0031] R3 is hydrogen; C1–C6 alkyl; C1–C6 alkyl having a nitrogen, oxygen, or sulfur atom; C3–C 10 Cycloalkyl; ternary to twelve-membered heterocyclic; or C1 to C6 alkoxy, and

[0032] X is hydrogen; halogen; C1–C6 alkyl; C1–C6 alkyl substituted with 1 to 3 halogens; C1–C6 alkyl having a nitrogen, oxygen, or sulfur atom; C1–C6 alkoxy; or C1–C6 alkoxy substituted with 1 to 3 halogens, and

[0033] W is a bond, -CH2-, -O-, -NH-, -CH2CH2-, -CH=CH-, or -C≡C-, and

[0034] A ring is a 6 to 12-membered aryl; a 5 to 12-membered heteroaryl; C3 to C 10 Cycloalkyl; or 3 to 12-membered heterocyclic, and

[0035] X1, X2, X3, and X4 are independently hydrogen; cyano; halogen; C1–C6 alkyl; C1–C6 alkoxy-C1–C6 alkyl; C1–C6 alkyl substituted with 1 to 3 halogens; C3–C 10 Cycloalkyl; ternary to twelve-membered heterocyclic; C1–C6 alkoxy; C1–C6 alkoxy substituted with 1 to 3 halogens; C1–C6 alkoxy-C1–C6 alkoxy; morpholineyl-C1–C6 alkoxy; mono- or di-C1–C6 alkylamino-C1–C6 alkoxy; C3–C 10 It is cycloalkyl-C1-C6 alkoxy; C1-C6 alkylthio; amino; mono- or di-C1-C6 alkylamino; C1-C6 alkylcarbonyl; hydroxy; or nitro.

[0036] In the compound of Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, preferably L may be -O-.

[0037] In addition, in the compound of Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, preferably Y and Z may be -O- or -CR1R2- independently of each other.

[0038] In addition, in the compound of Formula 1 according to the present invention or the pharmaceutically acceptable salt thereof, preferably, R1 and R2 are independently hydrogen or C1-C6 alkyl; or R1 and R2 are C3-C6 alkyl together with the carbon atom to which they are bonded. 10 A cycloalkyl group can be formed. In one embodiment, Y is -O-; and Z can be -CR1R2-.

[0039] In addition, in the compound of Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, preferably, X may be hydrogen, a halogen, or a C1-C6 alkoxy.

[0040] In addition, in the compound of Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, preferably, W may be a bond (i.e., the A ring is directly bonded to the 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety) or -CH=CH-.

[0041] In addition, in the compound of Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, preferably, the A ring may be a 6- to 12-membered aryl; a 5- to 12-membered heteroaryl; or a 3- to 12-membered heterocyclic. In one embodiment, the 6- to 12-membered aryl may be phenyl, naphthalenyl, or biphenyl. In another embodiment, the 5- to 12-membered heteroaryl may be benzodioxolyl, pyridineyl, thiopheneyl, quinolineyl, isoquinolineyl, benzofuranyl, benzo[b]thiopheneyl, quinoxalinyl, or furanyl. In another embodiment, the 3 to 12-membered heterocyclic may be 2,3-dihydrobenzodioxinyl, 2,3-dihydrobenzofuranyl, 3,4-dihydro-2H-benzo[b][1,4]oxazineyl, chromanyl, or 3,4-dihydro-2H-benzo[b][1,4]dioxepinyl.

[0042] In addition, in the compound of Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, preferably X1, X2, X3, and X4 are independently hydrogen; cyano; halogen; C1–C6 alkyl; C1–C6 alkoxy-C1–C6 alkyl; C1–C6 alkyl substituted with one to three halogens; C3–C 10Cycloalkyl; Morphoyl; C1–C6 alkoxy; C1–C6 alkoxy substituted with 1 to 3 halogens; C1–C6 alkoxy-C1–C6 alkoxy; Morphoyl-C1–C6 alkoxy; Mono- or di-C1–C6 alkylamino-C1–C6 alkoxy; C3–C 10 It may be cycloalkyl-C1-C6 alkoxy; C1-C6 alkylthio; mono- or di-C1-C6 alkylamino; or C1-C6 alkylcarbonyl.

[0043] In a preferred embodiment of the present invention,

[0044] L is -O- and,

[0045] Y and Z are, independently of each other, -O- or -CR1R2-, and

[0046] R1 and R2 are independently hydrogen or C1–C6 alkyl; or R1 and R2 are C3–C6 alkyl together with the carbon atom to which they are bonded. 10 Forming a cycloalkyl group,

[0047] X is hydrogen, a halogen, or a C1–C6 alkoxy, and

[0048] W is a bond or -CH=CH-, and

[0049] The A ring is a 6- to 12-membered aryl, a 5- to 12-membered heteroaryl, or a 3- to 12-membered heterocyclic, and

[0050] X1, X2, X3, and X4 are independently hydrogen; cyano; halogen; C1–C6 alkyl; C1–C6 alkoxy-C1–C6 alkyl; C1–C6 alkyl substituted with 1 to 3 halogens; C3–C 10 Cycloalkyl; Morphoyl; C1–C6 alkoxy; C1–C6 alkoxy substituted with 1 to 3 halogens; C1–C6 alkoxy-C1–C6 alkoxy; Morphoyl-C1–C6 alkoxy; Mono- or di-C1–C6 alkylamino-C1–C6 alkoxy; C3–C 10It is cycloalkyl-C1-C6 alkoxy; C1-C6 alkylthio; mono- or di-C1-C6 alkylamino; or C1-C6 alkylcarbonyl.

[0051] In the above embodiment, preferably Y is -O-; and Z may be -CR1R2-.

[0052] In the above embodiment, preferably, the A ring may be phenyl, naphthalenyl, or biphenyl.

[0053] In the above embodiment, preferably, the A ring may be benzodioxolyl, pyridineyl, thiopheneyl, quinolineyl, isoquinolineyl, benzofuranyl, benzo[b]thiopheneyl, quinoxalinyl, or furanyl.

[0054] In the above embodiment, preferably, the A ring may be 2,3-dihydrobenzodioxinyl, 2,3-dihydrobenzofuranyl, 3,4-dihydro-2H-benzo[b][1,4]oxazineyl, chromanyl, or 3,4-dihydro-2H-benzo[b][1,4]dioxepinyl.

[0055] In the compound of Formula 1 or a pharmaceutically acceptable salt thereof, the preferred compound may be a compound selected from the group consisting of the following compounds or a pharmaceutically acceptable salt thereof:

[0056] (S)-quinuclidin-3-yl (5-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0057] (S)-quinuclidin-3-yl (5-(4-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0058] (S)-quinuclidin-3-yl (5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0059] (S)-quinuclidin-3-yl (5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0060] (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0061] (S)-quinuclidin-3-yl (5-(3-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0062] (S)-quinuclidin-3-yl (5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0063] (S)-quinuclidin-3-yl (5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0064] (S)-quinuclidin-3-yl (5-(2-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0065] (S)-quinuclidin-3-yl (5-(2-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0066] (S)-quinuclidin-3-yl (5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0067] (S)-quinuclidin-3-yl (5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0068] (S)-quinuclidin-3-yl (5-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0069] (S)-quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0070] (S)-quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0071] (S)-quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0072] (S)-quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0073] (S)-quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0074] (S)-quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0075] (S)-quinuclidin-3-yl (5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0076] (S)-quinuclidin-3-yl (5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0077] (S)-quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0078] (S)-quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0079] (S)-quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0080] (S)-quinuclidin-3-yl (6-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0081] (S)-quinuclidin-3-yl (6-(4-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0082] (S)-quinuclidin-3-yl (6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0083] (S)-quinuclidin-3-yl (6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0084] (S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0085] (S)-quinuclidin-3-yl (6-(3-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0086] (S)-quinuclidin-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0087] (S)-quinuclidin-3-yl (6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0088] (S)-quinuclidin-3-yl (6-(2-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0089] (S)-quinuclidin-3-yl (6-(2-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0090] (S)-quinuclidin-3-yl (6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0091] (S)-quinuclidin-3-yl (6-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0092] (S)-quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0093] (S)-quinuclidin-3-yl (6-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0094] (S)-quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0095] (S)-quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0096] (S)-quinuclidin-3-yl (6-(2,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0097] (S)-quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0098] (S)-quinuclidin-3-yl (6-(2,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0099] (S)-quinuclidin-3-yl (6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0100] (S)-quinuclidin-3-yl (6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0101] (S)-quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0102] (S)-quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0103] (S)-quinuclidin-3-yl (6-(3,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0104] (S)-quinuclidin-3-yl (6-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0105] (S)-quinuclidin-3-yl (6-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0106] (S)-quinuclidin-3-yl(2,2-dimethyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0107] (S)-quinuclidin-3-yl(2,2-dimethyl-6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0108] (S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0109] (S)-quinuclidin-3-yl (6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0110] (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0111] (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0112] (S)-quinuclidin-3-yl (6-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0113] (S)-quinuclidin-3-yl (6-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0114] (S)-quinuclidin-3-yl(2,2-dimethyl-6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0115] (S)-quinuclidin-3-yl (2,2-dimethyl-6-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0116] (S)-quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0117] (S)-quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0118] (S)-quinuclidin-3-yl (6-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0119] (S)-quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0120] (S)-quinuclidin-3-yl (6-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0121] (S)-quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0122] (S)-quinuclidin-3-yl (2,2-dimethyl-6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0123] (S)-quinuclidin-3-yl(2,2-dimethyl-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0124] (S)-quinuclidin-3-yl (6-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0125] (S)-quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0126] (S)-quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0127] (S)-quinuclidin-3-yl (6-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0128] (S)-quinuclidin-3-yl (5-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0129] (S)-quinuclidin-3-yl (5-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0130] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0131] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0132] (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0133] (S)-quinuclidin-3-yl (5-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0134] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0135] (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0136] (S)-quinuclidin-3-yl (5-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0137] (S)-quinuclidin-3-yl (5-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0138] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0139] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0140] (S)-quinuclidin-3-yl (2,2-dimethyl-5-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0141] (S)-quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0142] (S)-quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0143] (S)-quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0144] (S)-quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0145] (S)-quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0146] (S)-quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0147] (S)-quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0148] (S)-quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0149] (S)-quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0150] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0151] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0152] (S)-quinuclidin-3-yl (5-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0153] (S)-quinuclidin-3-yl (5-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0154] (S)-quinuclidin-3-yl (5-(2-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0155] (S)-quinuclidin-3-yl (5-(4-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0156] (S)-quinuclidin-3-yl (5-(3-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0157] (S)-quinuclidin-3-yl (5-(2-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0158] (S)-quinuclidin-3-yl (5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0159] (S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0160] (S)-quinuclidin-3-yl (5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0161] (S)-quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0162] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-(methylthio)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0163] (S)-quinuclidin-3-yl (5-(3-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0164] (S)-quinuclidin-3-yl (5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0165] (S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0166] (S)-quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0167] (S)-quinuclidin-3-yl (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0168] (S)-quinuclidin-3-yl (5-(2,3-dihydrobenzofuran-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0169] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-(2-morphorinoethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0170] (S)-quinuclidin-3-yl (5-(4-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0171] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-(2,2,2-trifluoroethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0172] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-(2-morphorinoethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0173] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethyl)pyridine-4-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0174] (S)-quinuclidin-3-yl (5-(2,5-dichloropyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0175] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0176] (S)-quinuclidin-3-yl (5-(2-chloro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0177] (S)-quinuclidin-3-yl (5-(3-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0178] (S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0179] (S)-quinuclidin-3-yl (5-(2-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0180] (S)-quinuclidin-3-yl (5-(4-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0181] (S)-quinuclidin-3-yl (5-(2,3-dichloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0182] (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0183] (S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0184] (S)-quinuclidin-3-yl (5-(3-(dimethylamino)-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0185] (S)-quinuclidin-3-yl (5-(chroman-6-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0186] (S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0187] (S)-quinuclidin-3-yl (5-(4-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0188] (S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0189] (S)-quinuclidin-3-yl (5-(4-methoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0190] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0191] (S)-quinuclidin-3-yl (5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0192] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(thiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0193] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-methylthiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0194] (S)-quinuclidin-3-yl (5-(3-(2-(dimethylamino)ethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0195] (S)-quinuclidin-3-yl (5-(isoquinoline-8-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0196] (S)-quinuclidin-3-yl (5-(isoquinoline-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0197] (S)-quinuclidin-3-yl (5-(isoquinoline-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0198] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0199] (S)-quinuclidin-3-yl (5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0200] (S)-quinuclidin-3-yl (5-(2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0201] (S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0202] (S)-quinuclidin-3-yl (5-(4-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0203] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-morpholinophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0204] (S)-quinuclidin-3-yl (5-(4-(methoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0205] (S)-quinuclidin-3-yl (5-(4-(2,2-difluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0206] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-methyl-4-morpholinophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0207] (S)-quinuclidin-3-yl (5-(3-fluoro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0208] (S)-quinuclidin-3-yl (5-(3-chloro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0209] (S)-quinuclidin-3-yl (5-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0210] (S)-quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0211] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-8-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0212] (S)-quinuclidin-3-yl (5-(benzofuran-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0213] (S)-quinuclidin-3-yl (5-(benzofuran-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0214] (S)-quinuclidin-3-yl (5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0215] (S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0216] (S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0217] (S)-quinuclidin-3-yl (5-(2,4-dichloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0218] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0219] (S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0220] (S)-quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0221] (S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0222] (S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0223] (S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0224] (S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0225] (S)-quinuclidin-3-yl (5-(4-ethoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0226] (S)-quinuclidin-3-yl (5-(2,5-difluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0227] (S)-quinuclidin-3-yl (5-(2-fluoro-5-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0228] (S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0229] (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0230] (S)-quinuclidin-3-yl (5-(2-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0231] (S)-quinuclidin-3-yl (5-(2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0232] (S)-quinuclidin-3-yl (5-(2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0233] (S)-quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0234] (S)-quinuclidin-3-yl (5-(4-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0235] (S)-quinuclidin-3-yl (5-(4-methoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0236] (S)-quinuclidin-3-yl (5-(4-( tert -butoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0237] (S)-quinuclidin-3-yl (5-(2-chloro-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0238] (S)-quinuclidin-3-yl (5-(2-chloro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0239] (S)-quinuclidin-3-yl (5-(2,6-dimethoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0240] (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0241] (S)-quinuclidin-3-yl (5-(benzo[b]thiophene-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0242] (S)-quinuclidin-3-yl (5-(2-( tert -butoxy)pyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0243] (S)-quinuclidin-3-yl (5-(6-methoxy-5-(trifluoromethyl)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0244] (S)-quinuclidin-3-yl (5-(6-methoxynaphthalene-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0245] (S)-quinuclidin-3-yl (5-([1,1'-biphenyl]-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0246] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoxalin-6-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0247] (S)-quinuclidin-3-yl (5-(3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0248] (S)-quinuclidin-3-yl (5-(furan-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0249] (S)-quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0250] (S)-quinuclidin-3-yl (5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0251] (S)-quinuclidin-3-yl (5-(6-isopropoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0252] (S)-quinuclidin-3-yl (5-(3-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0253] (S)-quinuclidin-3-yl (5-(2-ethoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0254] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0255] (S)-quinuclidin-3-yl (5-(2-methoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0256] (S)-quinuclidin-3-yl (5-(2-butoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0257] (S)-quinuclidin-3-yl (5-(4-butoxy-3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0258] (S)-quinuclidin-3-yl (5-(2,4-dipropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0259] (S)-quinuclidin-3-yl (5-(3-chloro-4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0260] (S)-quinuclidin-3-yl (5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0261] (S)-quinuclidin-3-yl (5-(4-ethoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0262] (S)-quinuclidin-3-yl (5-(3-chloro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0263] (S)-quinuclidin-3-yl (5-(5-fluoro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0264] (S)-quinuclidin-3-yl (5-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0265] (S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0266] (S)-quinuclidin-3-yl (5-(2-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0267] (S)-quinuclidin-3-yl (5-(5-chloro-2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0268] (S)-quinuclidin-3-yl (5-(5-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0269] (S)-quinuclidin-3-yl (5-(2-fluoro-6-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0270] (S)-quinuclidin-3-yl (5-(3-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0271] (S)-quinuclidin-3-yl (5-(3-fluoro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0272] (S)-quinuclidin-3-yl (5-(5-chloro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0273] (S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0274] (S)-quinuclidin-3-yl (5-(3-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0275] (S)-quinuclidin-3-yl (5-(5-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0276] (S)-quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0277] (S)-quinuclidin-3-yl (5-(3-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0278] (S)-quinuclidin-3-yl (5-(2-chloro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0279] (S)-quinuclidin-3-yl (5-(3-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0280] (S)-quinuclidin-3-yl (5-(2-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0281] (S)-quinuclidin-3-yl (5-(4-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0282] (S)-quinuclidin-3-yl (5-(3,4-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0283] (S)-quinuclidin-3-yl (5-(4-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0284] (S)-quinuclidin-3-yl (5-(2-fluoro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0285] (S)-quinuclidin-3-yl (5-(2-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0286] (S)-quinuclidin-3-yl (5-(2-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0287] (S)-quinuclidin-3-yl (5-(5-isopropyl-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0288] (S)-quinuclidin-3-yl (5-(2-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0289] (S)-quinuclidin-3-yl (5-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0290] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(5-methylfuran-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0291] (S)-quinuclidin-3-yl (5-(3-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0292] (S)-quinuclidin-3-yl (5-(2-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0293] (S)-quinuclidin-3-yl (5-(benzo[b]thiophene-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0294] (S)-quinuclidin-3-yl (5-(4-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0295] (S)-quinuclidin-3-yl (5-(3-( tert -butyl)-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0296] (S)-quinuclidin-3-yl (5-(2-chloro-5-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0297] (S)-quinuclidin-3-yl (5-(4-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0298] (S)-quinuclidin-3-yl (5-(2-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0299] (S)-quinuclidin-3-yl (5-(5-cyano-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0300] (S)-quinuclidin-3-yl(5-(3-ethoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0301] (S)-quinuclidin-3-yl (5-(3-fluoro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0302] (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-methyl-4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0303] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-(methylthio)-5-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0304] (S)-quinuclidin-3-yl (5-(3-fluoro-4-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0305] (S)-quinuclidin-3-yl (5-(2-ethoxy-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0306] (S)-quinuclidin-3-yl (5-(2-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0307] (S)-quinuclidin-3-yl (5-(2,4-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0308] (S)-quinuclidin-3-yl (5-(3-chloro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0309] (S)-quinuclidin-3-yl (5-(3-methoxy-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0310] (S)-quinuclidin-3-yl (5-(4-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0311] (S)-quinuclidin-3-yl (5-(2-ethoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0312] (S)-quinuclidin-3-yl (5-(3-fluoro-5-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0313] (S)-quinuclidin-3-yl (5-(3,5-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0314] (S)-quinuclidin-3-yl (5-(3-chloro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0315] (S)-quinuclidin-3-yl (5-(2,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0316] (S)-quinuclidin-3-yl (5-(3-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0317] (S)-quinuclidin-3-yl (5-(6-ethoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0318] (S)-quinuclidin-3-yl (5-(2-ethoxypyridin-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0319] (S)-quinuclidin-3-yl (5-(2-isopropoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0320] (S)-quinuclidin-3-yl (2,2-dimethyl-5-(6-propoxypyridin-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0321] (S)-quinuclidin-3-yl (5-(6-butoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0322] (S)-quinuclidin-3-yl (5-(6-(2-methoxyethoxy)pyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0323] (S)-quinuclidin-3-yl (5-(6-isobutoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0324] (S)-quinuclidin-3-yl (5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0325] (S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0326] (S)-quinuclidin-3-yl (5-(2,4-dimethoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0327] (S)-quinuclidin-3-yl (5-(2-acetylthiophene-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0328] (S)-quinuclidin-3-yl (5-((E)-3-fluorostyryl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0329] (S)-quinuclidin-3-yl (5-((E)-4-ethylstyryl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0330] (S)-quinuclidin-3-yl (5-((E)-2-cyclohexylvinyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0331] (S)-quinuclidin-3-yl (2,2-diethyl-5-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0332] (S)-quinuclidin-3-yl (2,2-diethyl-5-(4-ethylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0333] (S)-quinuclidin-3-yl (2,2-diethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0334] (S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0335] (S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0336] (S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0337] (S)-quinuclidin-3-yl (2,2-diethyl-5-(4-isopropylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0338] (S)-quinuclidin-3-yl (2,2-diethyl-5-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0339] (S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0340] (S)-quinuclidin-3-yl (2,2-diethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0341] (S)-quinuclidene-3-yl (2,2-diethyl-5-(4-isopropoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0342] (S)-quinuclidin-3-yl (2,2-diethyl-5-(4-isobutylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0343] (S)-quinuclidin-3-yl (2,2-diethyl-5-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0344] (S)-quinuclidene-3-yl (2,2-diethyl-5-(3-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0345] (S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0346] (S)-quinuclidene-3-yl(2,2-diethyl-5-(3-isopropoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0347] (S)-quinuclidin-3-yl (2,2-diethyl-5-(3-ethylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0348] (S)-quinuclidin-3-yl (2,2-diethyl-5-(3-isopropylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0349] (S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0350] (S)-quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0351] (S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0352] (S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0353] (S)-quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0354] (S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0355] (S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0356] (S)-quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0357] (S)-quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0358] (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0359] (S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0360] (S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0361] (S)-quinuclidin-3-yl (2,2-diethyl-5-(thiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0362] (S)-quinuclidin-3-yl (2,2-diethyl-5-(furan-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0363] (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0364] (S)-quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0365] (S)-quinuclidin-3-yl (2,2-diethyl-5-(2-fluoro-4-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0366] (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0367] (S)-quinuclidin-3-yl (5-(4-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0368] (S)-quinuclidin-3-yl(6-methoxy-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0369] (S)-quinuclidin-3-yl (5-(4-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0370] (S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0371] (S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0372] (S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0373] (S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0374] (S)-quinuclidin-3-yl(6-methoxy-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0375] (S)-quinuclidin-3-yl (5-(4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0376] (S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0377] (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0378] (S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0379] (S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0380] (S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0381] (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0382] (S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0383] (S)-quinuclidin-3-yl (5-(4-butylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0384] (S)-quinuclidin-3-yl(6-methoxy-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0385] (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0386] (S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0387] (S)-quinuclidin-3-yl (6-methoxy-5-(2-methoxypyridin-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0388] (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0389] (S)-quinuclidin-3-yl (5-(3-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0390] (S)-quinuclidin-3-yl (5-(3-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0391] (S)-quinuclidin-3-yl (5-(3-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0392] (S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0393] (S)-quinuclidin-3-yl(6-methoxy-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0394] (S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0395] (S)-quinuclidin-3-yl(6-methoxy-2,2-methyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0396] (S)-quinuclidin-3-yl (5-(3-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0397] (S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0398] (S)-quinuclidin-3-yl (5-(3-isobutoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0399] (S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0400] (S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0401] (S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0402] (S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0403] (S)-quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0404] (S)-quinuclidin-3-yl (5-(4-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0405] (S)-quinuclidin-3-yl(6-fluoro-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0406] (S)-quinuclidin-3-yl(6-fluoro-5-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0407] (S)-quinuclidin-3-yl(6-fluoro-5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0408] (S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0409] (S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0410] (S)-quinuclidin-3-yl(6-fluoro-5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0411] (S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0412] (S)-quinuclidin-3-yl(6-fluoro-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0413] (S)-quinuclidin-3-yl(6-fluoro-5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0414] (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0415] (S)-quinuclidin-3-yl(6-fluoro-5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0416] (S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0417] (S)-quinuclidin-3-yl(6-fluoro-5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0418] (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0419] (S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0420] (S)-quinuclidin-3-yl (5-(4-butylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0421] (S)-quinuclidin-3-yl(6-fluoro-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0422] (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0423] (S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0424] (S)-quinuclidin-3-yl (6-fluoro-5-(2-methoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0425] (S)-quinuclidin-3-yl(6-fluoro-5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0426] (S)-quinuclidin-3-yl (5-(3-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0427] (S)-quinuclidin-3-yl(6-fluoro-5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0428] (S)-quinuclidin-3-yl(6-fluoro-5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0429] (S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0430] (S)-quinuclidin-3-yl(6-fluoro-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0431] (S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0432] (S)-quinuclidin-3-yl(6-fluoro-2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0433] (S)-quinuclidin-3-yl(6-fluoro-5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0434] (S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0435] (S)-quinuclidin-3-yl(6-fluoro-5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0436] (S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0437] (S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0438] (S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0439] (S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0440] (S)-quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0441] (S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0442] (S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0443] (S)-quinuclidin-3-yl(6-fluoro-5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0444] (S)-quinuclidin-3-yl (5'-(4-fluorophenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0445] (S)-quinuclidein-3-yl (5'-(4-chlorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0446] (S)-quinuclidin-3-yl (5'-(4-(trifluoromethyl)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0447] (S)-quinuclidein-3-yl (5'-(4-(trifluoromethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0448] (S)-quinuclidein-3-yl (5'-(3-chlorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0449] (S)-quinuclidin-3-yl (5'-(3-(trifluoromethyl)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0450] (S)-quinuclidein-3-yl (5'-(4-(2-methoxyethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0451] (S)-quinuclidein-3-yl (5'-(3-(2-methoxyethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0452] (S)-quinuclidein-3-yl (5'-(4-(methoxymethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0453] (S)-quinuclidein-3-yl (5'-(3-(methoxymethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;

[0454] (S)-quinuclidin-3-yl (5-(3-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0455] (S)-quinuclidin-3-yl (5-(2-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;

[0456] (S)-quinuclidin-3-yl(3,3-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0457] (S)-quinuclidin-3-yl(3,3-dimethyl-5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0458] (S)-quinuclidin-3-yl(3,3-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;

[0459] (S)-quinuclidin-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate;

[0460] (S)-quinuclidin-3-yl (6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate;

[0461] (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate;

[0462] (S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate;

[0463] (S)-quinuclidin-3-yl (6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate;

[0464] (S)-quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate;

[0465] (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate; and

[0466] (S)-quinuclidin-3-yl (6-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate.

[0467] The compound of Formula 1 or its pharmaceutically acceptable salt may exist as geometric isomers of cis or trans structures. Therefore, unless otherwise indicated, the compound of Formula 1 or its salt comprises both geometric isomers of cis and trans structures. Additionally, the compound of Formula 1 or its pharmaceutically acceptable salt may have substituents containing asymmetric atoms; in this case, the compound of Formula 1 or its pharmaceutically acceptable salt may exist as a racemic (RS) or optical isomer, such as (R) or (S). Therefore, unless otherwise indicated, the compound of Formula 1 or its pharmaceutically acceptable salt comprises both the racemic (RS) and optical isomers, such as the (R) or (S) isomers. Additionally, the compound of Formula 1 or a pharmaceutically acceptable salt thereof may have two or more chiral centers, and unless otherwise indicated, the compound of Formula 1 or a pharmaceutically acceptable salt thereof may exist as one or more diastereomers or a mixture thereof. Thus, unless otherwise indicated, the compound of Formula 1 or a pharmaceutically acceptable salt thereof comprises each of the diastereomers or a mixture thereof.

[0468] The compound of Formula 1 of the present invention may be in the form of a pharmaceutically acceptable salt. The salt comprises conventional acid addition salts, for example, salts derived from inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid, and bromic acid, and salts derived from organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, succinic acid, benzoic acid, citric acid, maleic acid, malonic acid, malic acid, tartaric acid, gluconic acid, lactic acid, gestic acid, fumaric acid, lactobionic acid, salicylic acid, phthalic acid, emvonic acid, aspartic acid, glutamic acid, and acetylsalicylic acid. Additionally, the salt may be glycine, alanine, valine, isoleucine, serine, cysteine, cystine, aspartic acid, glutamine, lysine, It includes salts derived from amino acids such as arginine, tyrosine, and proline. In addition, the salts include salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, and toluenesulfonic acid.

[0469] The compound of Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof can be prepared in various ways.

[0470] For example, the compound of Formula 1a or a pharmaceutically acceptable salt thereof according to the present invention may be prepared by a method comprising the steps of: reacting a compound of Formula 2 or a salt thereof with ethyl chloroformate to obtain a compound of Formula 3, as shown in Reaction Scheme 1 below; coupling the compound of Formula 3 with a compound of Formula 4 to obtain a compound of Formula 5; reacting the compound of Formula 5 with an AW-boronic acid substituted with X1, X2, X3, or X4 to obtain a compound of Formula 1a; and optionally, converting the compound of Formula 1a into a pharmaceutically acceptable salt thereof.

[0471] <Reaction Equation 1>

[0472]

[0473] In the above reaction scheme 1, X, Y, Z, W, A ring, X1, X2, X3, and X4 are the same as defined above.

[0474] The compound of Formula 2 above may be commercially purchased or synthesized from known compounds according to the literature. The reaction of the compound of Formula 2 or its salt with ethyl chloroformate yields triethylamine, N,N - It may be carried out in the presence of an organic base such as diisopropylethylamine or an inorganic base such as potassium carbonate. The base may be used in a range of 1 to 1.5 equivalents per 1 equivalent of the compound of Formula 2 or in a range of 3 to 5 equivalents per 1 equivalent of the salt of the compound of Formula 2 (e.g., hydrochloride). The reaction may be carried out in a solvent such as dichloromethane or tetrahydrofuran, preferably at 0°C to room temperature.

[0475] The coupling of the compound of Formula 3 and the compound of Formula 4 (i.e., quinuclideinol) can be carried out through a condensation reaction that removes ethanol. The reaction can preferably be carried out in the presence of a base such as sodium hydride. Additionally, the reaction can be carried out in a non-polar organic solvent such as toluene at 120°C to 140°C.

[0476] The reaction between the compound of Chemical Formula 5 and AW-boronic acid substituted with X1, X2, X3, or X4 can be carried out via a Suzuki reaction. The Suzuki reaction can be carried out using a palladium catalyst, and the palladium catalyst may be, for example, tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4), palladium(II) acetate (Pd(OAc)2), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(Pd(dppf)Cl2), etc. Additionally, the Suzuki reaction can be carried out in the presence of inorganic bases such as cesium carbonate (Cs2CO3), sodium carbonate (Na2CO3), potassium carbonate (K2CO3), and potassium phosphate (K3PO4). The above Suzuki reaction uses a non-polar organic solvent such as toluene or 1,4-dioxane, tetrahydrofuran, acetonitrile, 1,2-dimethoxyethane, or as a reaction solvent. N,N - It can be carried out in a polar organic solvent such as dimethylformamide at 50°C to 150°C, preferably 80°C to 120°C. Other reaction conditions, including reaction time, can be carried out according to known methods for the Suzuki reaction.

[0477] The conversion of the compound of Formula 1a into a pharmaceutically acceptable salt can be carried out according to ordinary methods. For example, a pharmaceutically acceptable salt of the compound of Formula 1a can be prepared by dissolving the compound of Formula 1a in a water-miscible solvent such as methanol, ethanol, acetone, or 1,4-dioxane, and then adding a free acid or free base to crystallize it.

[0478] In addition, the compound of Formula 1a or a pharmaceutically acceptable salt thereof according to the present invention may be prepared by a manufacturing method comprising the steps of: reacting a compound of Formula 4 with a bis(4-nitrophenyl) carbonate to obtain a compound of Formula 7, as shown in Reaction Scheme 2 below; reacting the compound of Formula 7 with a compound of Formula 2 to obtain a compound of Formula 5; reacting the compound of Formula 5 with an AW-boronic acid substituted with X1, X2, X3, or X4 to obtain a compound of Formula 1a; and optionally, converting the compound of Formula 1a into a pharmaceutically acceptable salt thereof.

[0479] <Reaction Equation 2>

[0480]

[0481] In the above reaction scheme 2, X, Y, Z, W, A ring, X1, X2, X3, and X4 are the same as defined above.

[0482] The reaction between the compound of chemical formula 4 (i.e., quinuclideinol) and bis(4-nitrophenyl) carbonate is N,N - It can be carried out in a polar solvent such as dimethylformamide, preferably at 0°C to 25°C. The compound of Formula 7 can also be prepared by reacting the compound of Formula 4 with 4-nitrophenyl chloroformate in the presence of a base such as triethylamine, for example, in a solvent such as dichloromethane or acetonitrile.

[0483] The reaction between the compound of Chemical Formula 7 and the compound of Chemical Formula 2 is N,N - It can be carried out in a solvent such as dimethylformamide, tetrahydrofuran, or acetonitrile, and N,N - It can be carried out at 0°C to 25°C in the presence of a base such as diisopropylethylamine or triethylamine.

[0484] The reaction between the compound of Formula 5 and AW-boronic acid substituted with X1, X2, X3, or X4 can be carried out via the Suzuki reaction as described above. Additionally, the conversion of the compound of Formula 1a into a pharmaceutically acceptable salt can be carried out according to conventional methods as described above.

[0485] Derivatives having a 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety according to the present invention, i.e., compounds of Formula 1 or pharmaceutically acceptable salts thereof, have excellent inhibitory activity against glucosylceramide synthase, and thus can be usefully used for the treatment and prevention of various diseases mediated by glucosylceramide synthase.

[0486] Accordingly, the present invention comprises a pharmaceutical composition for inhibiting glucosylceramide synthase, comprising a therapeutically effective amount of the compound of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient. In one embodiment, the present invention provides a pharmaceutical composition for the prevention or treatment of diseases associated with GCS activity, such as Gaucher disease, Fabry disease, Tay-Sachs disease, Parkinson's disease, etc., comprising a therapeutically effective amount of the compound of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.

[0487] The pharmaceutical composition of the present invention may include pharmaceutically acceptable carriers such as commonly used excipients, disintegrants, sweeteners, lubricants, or flavoring agents, and may be formulated according to conventional methods into oral preparations such as tablets, capsules, powders, granules, suspensions, emulsions, or syrups; or into parenteral preparations such as external liquids, external suspensions, external emulsions, gels (ointments, etc.), inhalants, sprays, or injections. The preparations may be formulated in various forms, for example, as single-dose or multi-dose dosage forms.

[0488] The pharmaceutical composition of the present invention may include excipients such as lactose and corn starch, lubricants such as magnesium stearate, emulsifiers, suspending agents, stabilizers, and isotonic agents. If necessary, sweeteners and / or flavoring agents may be added.

[0489] The compositions of the present invention may be administered orally or parenterally, including by inhalation, intravenous, intraperitoneal, subcutaneous, rectal, and topical administration. Accordingly, the compositions of the present invention may be formulated in various forms, such as tablets, capsules, aqueous solutions, or suspensions. For oral tablets, carriers such as lactose or corn starch and lubricants such as magnesium stearate may typically be added. For oral capsules, lactose and / or dried corn starch may be used as diluents. If an oral aqueous suspension is required, the active ingredient may be combined with an emulsifier and / or suspending agent. If necessary, specific sweeteners and / or flavoring agents may be added. For intramuscular, intraperitoneal, subcutaneous, and intravenous administration, a sterile solution of the active ingredient is typically prepared, and the pH of the solution must be appropriately adjusted and buffered. For intravenous administration, the total concentration of the solute must be adjusted to impart isotonicity to the formulation. The composition according to the present invention may be in the form of an aqueous solution containing a pharmaceutically acceptable carrier, such as saline solution with a pH of 7.4. The solution may be introduced into the intramuscular bloodstream of a patient by local bolus injection.

[0490] The compound of Formula 1 or a pharmaceutically acceptable salt thereof may be administered to a patient in an effective amount of about 0.0001 mg / kg to about 100 mg / kg per day. Of course, the above dose may be changed depending on the patient's age, body weight, sensitivity, symptoms, or the pharmacological effect of the compound.

[0491] The present invention also includes a method for inhibiting glucosylceramide synthase in mammals, comprising administering a therapeutically effective amount of the compound of Formula 1 or a pharmaceutically acceptable salt thereof to a mammal. In one embodiment, the present invention provides a method for treating diseases associated with GCS activity, such as Gaucher disease, Fabry disease, Tay-Sachs disease, Parkinson's disease, etc., comprising administering a therapeutically effective amount of the compound of Formula 1 or a pharmaceutically acceptable salt thereof to a mammal.

[0492] The present invention also provides a use of the compound of Formula 1 or a pharmaceutically acceptable salt thereof for use in the manufacture of a drug that inhibits glucosylceramide synthase in mammals. In one embodiment, the present invention provides a use of the compound of Formula 1 or a pharmaceutically acceptable salt thereof for use in the manufacture of a drug for the prevention or treatment of diseases associated with GCS activity, such as Gaucher disease, Fabry disease, Tay-Sachs disease, Parkinson's disease, etc.

[0493] The present invention will be explained in more detail below through examples and test examples. However, these examples and test examples are illustrative of the present invention and are not limited thereto.

[0494] In the following examples, brine refers to an aqueous solution of saturated sodium chloride. Unless otherwise specified, all temperatures are in °C (degrees). All reactions were performed at room temperature unless otherwise specified.

[0495] The compounds prepared in the following reference examples and examples were analyzed as follows: Nuclear magnetic resonance (NMR) spectral analysis was performed on a Bruker 400 MHz spectrometer, and chemical shifts were analyzed in ppm. Column chromatography was performed on silica gel (Merck, 70-230 mesh). Additionally, each starting material was a known compound, synthesized according to the literature, or purchased commercially. All reaction and column chromatography fractions were analyzed by thin-layer chromatography (TLC) on 250 nm silica gel plates and visualized by ultraviolet light or iodine (I2) staining.

[0497] Reference Example 1. (S)-quinuclidin-3-yl(5-bromo-2,3-dihydro-1H-indene-1-yl)carbamate

[0498] Step 1. Ethyl (5-bromo-2,3-dihydro-1H-indene-1-yl)carbamate

[0499] 5-bromo-2,3-dihydro-1H-indene-1-amine (2 g, 9.4 mmol) was dissolved in dichloromethane (50 ml), then triethylamine (1.45 ml, 10.4 mmol) and ethyl chloroformate (1 ml, 10.4 mmol) were added dropwise in sequence, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and it was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting pale yellow oily residue (2.6 g) was used in the following reaction without further purification.

[0500] Step 2. (S)-quinuclidin-3-yl(5-bromo-2,3-dihydro-1H-indene-1-yl)carbamate

[0501] (S)-(+)-3-quinuclidinol (3.5 g, 27.5 mmol) was dissolved in toluene (80 ml), sodium hydride (219.6 mg, 9.2 mmol) was added at 0°C and stirred for 15 minutes. Ethyl (5-bromo-2,3-dihydro-1H-indene-1-yl)carbamate (2.6 g, 9.2 mmol) prepared in Step 1 was added to the reaction mixture, and the mixture was refluxed and stirred at 140°C for 21 hours. After cooling the reaction mixture to room temperature, brine was added and extracted with ethyl acetate. The organic layer was washed twice with brine, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography (ethyl acetate / (methanol / ammonia water=1 / 1)= 9 / 1, v / v) to prepare the white solid title compound. (1.3 g, yield: 46%)

[0502] 1 H-NMR (400MHz, CDCl3) δ 7.34(s, 1H), 7.30(m, 1H), 7.15(m, 1H), 5.50(br, 1H), 5.13(m, 1H), 4.75(m, 2H), 3.18(m, 2H), 2.82~2.68(m, 7H), 1.96(m, 1H), 1.80(m, 1H), 1.66(m, 1H), 1.55(m, 1H), 1.37(m, 1H)

[0504] Reference Example 2. (S)-quinuclidin-3-yl(6-bromo-2,3-dihydro-1H-indene-1-yl)carbamate

[0505] The title compound was prepared using 6-bromo-2,3-dihydro-1H-indene-1-amine as a starting material in the same manner as in Reference Example 1.

[0506] 1H-NMR (400MHz, CDCl3) δ 7.40(s, 1H), 7.30(m, 1H), 7.08(d, 1H), 5.51(br, 1H), 5.19(m, 1H), 4.75(m, 2H), 3.20(m, 2H), 2.82~2.69(m, 7H), 1.97(m, 1H), 1.80(m, 1H), 1.67(m, 1H), 1.55(m, 1H), 1.38(m, 1H)

[0508] Reference Example 3. (S)-quinuclidin-3-yl(6-bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0509] The title compound was prepared using 6-bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-amine as a starting material in the same manner as in Reference Example 1.

[0510] 1 H-NMR (400MHz, CDCl3) δ 7.28(m, 2H), 7.00(d, 1H), 4.89(m, 1H), 4.73(m, 2H), 3.15(m, 1H), 2.81~2.70(m, 7H), 1.95(m, 1H), 1.80(br, 1H), 1.64(br, 1H), 1.53(br, 1H), 1.39(br, 1H), 0.85(d, 6H)

[0512] Reference Example 4. (S)-quinuclidin-3-yl(5-bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0513] Step 1. 5-Bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-amine hydrochloride

[0514] 5-bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-one (100 g, 418.2 mmol) was dissolved in methanol (500 ml) and isopropanol (500 ml), and then ammonium acetate (515.8 g, 6691.5 mmol) and sodium cyanoborohydride (157.7 g, 2509.3 mmol) were added dropwise at room temperature. The reaction mixture was stirred at room temperature for 4 hours, followed by reflux stirring at 80°C for 22 hours. After cooling the reaction mixture to room temperature, it was basicized to pH > 12 using a 1N aqueous sodium hydroxide solution, and then extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. Ethyl acetate was added to the obtained residue, followed by the addition of a 4M hydrochloric acid solution in 1,4-dioxane, and the mixture was stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure, washed with ethyl acetate, and dried to prepare the white solid title compound. (100 g, yield: 86.5%).

[0515] 1 H-NMR (400MHz, CD3OD) δ 7.50(m, 2H), 7.39(d, 1H), 4.28(s, 1H), 3.02~2.82(m, 2H), 1.24(s, 3H), 1.20(s, 3H)

[0516] Step 2. (S)-quinuclidin-3-yl(5-bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0517] (S)-(+)-3-quinuclideinol (38.6 g, 303.7 mmol) and bis(4-nitrophenyl) carbonate (92.4 g, 303.7 mmol) N,NAfter dissolving in dimethylformamide (700 ml), the mixture was stirred at room temperature for 8 hours. 5-bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-amine hydrochloride (70 g, 253.1 mmol) and diisopropylethylamine (132.3 ml, 759.2 mmol) prepared in Step 1 were added to the solution, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water (500 ml), acidified to pH 1–2 using a 1N aqueous hydrochloric acid solution, and then extracted using diisopropyl ether (300 ml × 2). The aqueous layer was based to approximately pH 12 using ammonia and extracted with ethyl acetate. The extract was washed with water, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was dissolved in isopropyl acetate, heptane was added, and the mixture was stirred overnight at room temperature. The resulting solid was filtered under reduced pressure, washed with heptane, and dried to prepare the white solid title compound. (56 g, Yield: 56.3%)

[0518] 1 H-NMR (400MHz, CDCl3) δ 7.32(m, 2H), 7.09(m, 1H), 4.89(m, 1H), 4.86(m, 1H), 4.77(m, 1H), 3.25(m, 1H), 2.87~2.75(m, 2H), 2.74~2.69(m, 5H), 2.07(m, 1H), 1.83(br, 1H), 1.69(br, 1H), 1.57(br, 1H), 1.41(br, 1H), 1.27(s, 3H), 0.92(s, 3H)

[0520] Reference Example 5. (S)-quinuclidin-3-yl(5-bromo-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0521] Step 1. 5-Bromo-2,2-diethyl-2,3-dihydro-1H-indene-1-one

[0522] 5-bromo-1-indane (20 g, 94.8 mmol) was dissolved in tetrahydrofuran (100 ml), and then 60% sodium hydride (19 g, 473.8 mmol) was added at 0°C and stirred for 15 minutes. At the same temperature, iodoethane (19.1 ml, 236.9 mmol) was added dropwise to the reaction mixture and stirred overnight at room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was column chromatographed ( n The white solid title compound was prepared by purification with -hexane / ethyl acetate (10 / 1, v / v). (17 g, yield: 67%)

[0523] 1 H-NMR (400MHz, CDCl3) δ 7.61(s, 1H), 7.58(m, 1H), 7.51(m, 1H), 2.97(s, 2H), 1.65(m, 2H), 1.62(m, 2H), 0.77(t, 6H)

[0524] Step 2. 5-Bromo-2,2-diethyl-2,3-dihydro-1H-indene-1-amine hydrochloride

[0525] The title compound was prepared using the 5-bromo-2,2-diethyl-2,3-dihydro-1H-indene-1-one prepared in Step 1 in the same manner as in Step 1 of Reference Example 4.

[0526] 1 H-NMR (400MHz, MeOD) δ 7.49(s, 1H), 7.45(m, 2H), 4.38(s, 1H), 3.07(m, 1H), 2.83(m, 1H), 1.70(m, 2H), 1.40(m, 2H), 1.09(t, 3H), 0.88(t, 3H)

[0527] Step 3. (S)-quinuclidin-3-yl(5-bromo-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0528] The title compound was prepared using the 5-bromo-2,2-diethyl-2,3-dihydro-1H-indene-1-amine hydrochloride prepared in Step 2 in the same manner as in Step 2 of Reference Example 4.

[0529] 1 H-NMR (400MHz, CDCl3) δ 7.32(m, 2H), 7.09(m, 1H), 5.01(m, 1H), 4.85(m, 1H), 4.76(m, 1H), 3.25(m, 1H), 2.89~2.70(m, 7H), 2.10(br, 1H), 1.80(br, 1H), 1.69(br, 1H), 1.55(m, 3H), 1.49(m, 2H), 1.40(br, 1H), 0.95(m, 3H), 0.81(m, 3H)

[0531] Reference Example 6. (S)-quinuclidin-3-yl(5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0532] Step 1. 5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-one

[0533] 5-bromo-6-methoxy-2,3-dihydro-1H-indene-1-one (10 g, 43.7 mmol) was dissolved in tetrahydrofuran (50 ml), and then 60% sodium hydride (8.7 g, 218.3 mmol) was added at 0°C and stirred for 15 minutes. At the same temperature, iodomethane (10.9 ml, 174.6 mmol) was added dropwise to the reaction mixture and stirred overnight at room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography ( n The white solid title compound was prepared by purification with -hexane / ethyl acetate (10 / 1, v / v). (10 g, yield: 89%)

[0534] 1H-NMR (400MHz, CDCl3) δ 7.66(s, 1H), 7.21(s, 1H), 3.94(s, 3H), 2.93(s, 2H), 1.24(s, 6H)

[0535] Step 2. 5-Bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-amine hydrochloride

[0536] The title compound was prepared using the 5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-one prepared in Step 1 in the same manner as in Step 1 of Reference Example 4.

[0537] 1 H-NMR (400MHz, MeOD) δ 7.47(s, 1H), 7.23(s, 1H), 4.29(s, 1H), 4.11(s, 3H), 2.95~2.92(m, 1H), 2.78~2.74(m, 1H), 1.29(m, 3H), 0.98(m, 3H)

[0538] Step 3. (S)-quinuclidin-3-yl(5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0539] The title compound was prepared using the 5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-amine hydrochloride prepared in Step 2 in the same manner as in Step 2 of Reference Example 4.

[0540] 1 H-NMR (400MHz, CDCl3) δ 7.34(s, 1H), 6.77(m, 1H), 4.87(s, 2H), 4.78(m, 1H), 3.85(m, 3H), 3.25(m, 1H), 2.78~2.61(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.57(br, 1H), 1.44(br, 1H), 1.21(m, 3H), 0.95(m, 3H)

[0542] Reference Example 7. (S)-quinuclidin-3-yl(5-bromo-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0543] The title compound was prepared using 5-bromo-6-fluoro-2,3-dihydro-1H-indene-1-one as a starting material in the same manner as in Reference Example 6.

[0544] 1 H-NMR (400MHz, CDCl3) δ 7.34(d, 1H), 7.01(d, 1H), 4.91(m, 1H), 4.84(m, 1H), 4.69(m, 1H), 3.25(m, 1H), 2.93~2.72(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.40(br, 1H), 1.27(m, 3H), 0.92(m, 3H)

[0546] Reference Example 8. (S)-quinuclidin-3-yl (5'-bromo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[0547] Step 1. 5'-Bromospiro[cyclopropane-1,2'-indene]-1'(3'H)-on

[0548] 5-bromo-1-indane (5 g, 23.7 mmol) N,N After dissolving in dimethylformamide (100 ml), 60% sodium hydride (2.7 g, 35.5 mmol) was added at 0°C and stirred for 15 minutes. At the same temperature, 1,2-dibromomethane (5.1 ml, 35.5 mmol) was added dropwise to the reaction mixture and stirred overnight at room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography ( n The white solid title compound was prepared by purification with hexane / ethyl acetate (10 / 1, v / v). (3.5 g, yield: 62%)

[0549] 1 H-NMR (400MHz, CDCl3) δ 7.69(s, 1H), 7.65(m, 1H), 7.55(d, 1H), 3.15(s, 2H), 1.47(d, 2H), 1.19(d, 2H)

[0550] Step 2. 5'-Bromo-1',3'-Dihydropyro[cyclopropane-1,2'-indene]-1'-amine hydrochloride

[0551] Using the 5'-bromospyro[cyclopropane-1,2'-indene]-1'(3'H)-one prepared in Step 1, the title compound was prepared in the same manner as in Step 1 of Reference Example 4.

[0552] 1 H-NMR (400MHz, MeOD) δ 7.56(s, 1H), 7.52(m, 1H), 7.45(m, 1H), 4.25(s, 1H), 3.45(m, 1H), 2.71(m, 1H), 1.15(m, 1H), 0.92(m, 2H), 0.82(m, 1H)

[0553] Step 3. (S)-quinuclidein-3-yl (5'-bromo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[0554] Using the 5'-bromo-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-amine hydrochloride prepared in Step 2, the title compound was prepared in the same manner as in Reference Example 1.

[0555] 1H-NMR (400MHz, CDCl3) δ 7.36(m, 2H), 7.24(m, 1H), 4.92(m, 1H), 4.91(m, 1H), 4.74(m, 1H), 3.25(m, 1H), 3.00(m, 2H), 2.87~2.68(m, 5H), 1.97(br, 1H), 1.79(m, 1H), 1.67(br, 1H), 1.56(m, 1H), 1.41(br, 1H), 0.91(m, 2H), 0.81(m, 1H), 0.59(m, 1H)

[0557] Reference Example 9. (S)-quinuclidin-3-yl(5-bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0558] Step 1. 6-Bromo-1,1-dimethyl-2,3-dihydro-1H-indene

[0559] Under a nitrogen atmosphere, a 1.0 M titanium(IV) chloride solution in dichloromethane (28.4 ml) was slowly added dropwise to dichloromethane (20 ml) at -30°C. To the resulting solution, a 2.0 M dimethyl zinc solution in toluene (16.6 ml) was slowly added dropwise at the same temperature and stirred for 30 minutes. To the reaction mixture, a solution of 6-bromo-2,3-dihydro-1H-indene-1-one (2 g, 9.5 mmol) in dichloromethane (10 ml) was slowly added dropwise and stirred at -10°C for 4 hours. The reaction was stopped by adding ice water to the reaction mixture, and then extracted with ethyl acetate. The organic layer was washed with salt water, the extract was dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography ( n The white solid title compound was prepared by purification with -hexane / ethyl acetate (5 / 1, v / v) (2.1 g, yield: 99%).

[0560] 1H NMR (400 MHz, CDCl3) δ 7.28(s, 1H), 7.20(d, 1H), 7.07(d, 1H), 2.85(t, 2H), 1.94(t, 2H), 1.26(s, 6H)

[0561] Step 2. 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-one

[0562] 6-bromo-1,1-dimethyl-2,3-dihydro-1H-indene (1.9 g, 8.4 mmol) prepared in Step 1 was dissolved in acetone (20 ml), and then a solution of anhydrous magnesium sulfate (2.5 g, 21.1 mmol) in water (10 ml) was added dropwise. Potassium permanganate (4 g, 25.3 mmol) was slowly added dropwise to the reaction mixture, and the mixture was stirred under reflux for 5 hours. After cooling the reaction mixture to room temperature, it was filtered and concentrated under reduced pressure. The resulting residue was diluted with an ethyl acetate solution, washed with salt water, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography ( n The white solid title compound was prepared by purification with -hexane / ethyl acetate (5 / 1, v / v). (1.85 g, yield: 92%)

[0563] 1 H NMR (400 MHz, CDCl3) δ 7.65(s, 1H), 7.58~7.47(m, 2H), 2.58(s, 2H), 1.42(s, 6H)

[0564] Step 3. 5-Bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-amine hydrochloride

[0565] Using the 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-one prepared in Step 2, the title compound was prepared in the same manner as in Step 1 of Reference Example 4. The obtained product was used in the following reaction without further purification.

[0566] Step 4. Ethyl (5-bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0567] Using the 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-amine hydrochloride prepared in Step 3, the title compound was prepared in the same manner as in Step 1 of Reference Example 1.

[0568] 1 H NMR (400 MHz, CDCl3) δ 7.35(d, 1H), 7.30(s, 1H), 7.16(d, 1H), 5.24(q, 1H), 4.81(brd, 1H), 4.17(q, 2H), 2.46(m, 1H), 1.73~1.68(m, 1H), 1.37(s, 3H), 1.28(t, 3H), 1.22(s, 3H)

[0569] Step 5. (S)-quinuclidin-3-yl(5-bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0570] The title compound was prepared using the ethyl (5-bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Step 4 in the same manner as in Step 2 of Reference Example 1.

[0571] 1 H NMR (400 MHz, MeOD) δ 7.38~7.33(m, 2H), 7.14(dd, 1H), 5.14(t, 1H), 4.80~4.75(m, 1H), 3.30~3.21(m, 1H), 2.90~2.69(m, 5H), 2.39~2.32(m, 1H), 2.11~2.04(m, 1H), 1.99~1.90(m, 1H), 1.84~1.74(m, 2H), 1.70~1.61(m, 1H), 1.55~1.45(m, 1H), 1.39(s, 3H), 1.22(s, 3H)

[0573] Reference Example 10. (S)-quinuclidin-3-yl(6-bromo-2,3-dihydrobenzofuran-3-yl)carbamate

[0574] The title compound was prepared using 6-bromo-2,3-dihydrobenzofuran-3-amine as a starting material in the same manner as in Reference Example 1.

[0575] 1 H-NMR (400MHz, CDCl3) δ 7.21(t, 1H), 7.08~7.06(m, 1H), 7.02(s, 1H), 5.35~5.31(m, 2H), 4.73~4.68(m, 2H), 4.41~4.37(m, 1H), 3.24~3.19(m, 1H), 2.82~2.66(m, 5H), 2.05~1.98(m, 1H), 1.75~1.66(m, 2H), 1.56~1.55(m, 1H), 1.40~1.38(m, 1H)

[0577] Reference Example 11. (S)-quinuclidin-3-yl(5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate

[0578] Step 1. 5-Bromo-2,2-dimethylbenzofuran-3(2H)-one

[0579] 5-Bromobenzofuran-3-one (2.75 g, 12.9 mmol) was dissolved in tetrahydrofuran (43 ml), and then 60% sodium hydride (2.07 g, 51.6 mmol) was added at 0°C and stirred for 15 minutes. At the same temperature, iodomethane (9.15 g, 64.5 mmol) was added dropwise to the reaction mixture and stirred overnight at room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography ( n The white solid title compound was prepared by purification with -hexane / ethyl acetate (10 / 1, v / v). (2.5 g, yield: 80%)

[0580] 1 H-NMR (400MHz, CDCl3) δ 7.81(s, 1H), 7.79(d, 1H), 6.98(d, 1H), 1.47(s, 6H)

[0581] Step 2. 5-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-amine

[0582] The title compound was prepared using the 5-bromo-2,2-dimethylbenzofuran-3(2H)-one prepared in Step 1 in the same manner as in Step 1 of Reference Example 4.

[0583] 1 H-NMR (400MHz, CDCl3) δ 7.40(s, 1H), 7.27(d, 1H), 6.63(d, 1H), 4.12(s, 1H), 1.41(d, 6H)

[0584] Step 3. (S)-quinuclidin-3-yl(5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate

[0585] Using the 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-amine prepared in Step 2, the title compound was prepared in the same manner as in Reference Example 1.

[0586] 1 H-NMR (400MHz, CDCl3) δ 7.40(d, 1H), 7.31(d, 1H), 6.65(d, 1H), 5.36(t, 1H), 5.00(d, 1H), 4.78~4.69(m, 1H), 3.25~3.15(m, 1H), 2.89~2.59(m, 5H), 2.06~2.00(m, 1H), 1.83~1.74(m, 1H), 1.72~1.63(m, 1H), 1.60~1.51(m, 1H), 1.48(s, 3H), 1.41~1.36(m, 4H)

[0588] Reference Example 12. (S)-quinuclidin-3-yl(6-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate

[0589] Step 1. 6-bromo-2,2-dimethylbenzofuran-3(2H)-one

[0590] The title compound was prepared using 6-bromobenzofuran-3(2H)-one as a starting material in the same manner as Step 1 of Reference Example 11.

[0591] 1 H-NMR (400MHz, CDCl3) δ 7.53(d, 1H), 7.30~7.27(m, 1H), 7.21(dd, 1H), 1.47(s, 6H)

[0592] Step 2. (S)-quinuclidin-3-yl(6-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate

[0593] Using the 6-bromo-2,2-dimethylbenzofuran-3(2H)-one prepared in Step 1, the title compound was prepared in the same manner as in Reference Example 4.

[0594] 1 H-NMR (400MHz, CDCl3) δ 7.14(dd, 1H), 7.05~6.99(m, 1H), 6.91(s, 1H), 5.59~5.46(m, 1H), 4.94(d, 1H), 4.77~4.66(m, 1H), 3.27~3.14(m, 1H), 2.91~2.61(m, 5H), 2.12~2.01(m, 1H), 1.86~1.64(m, 2H), 1.61~1.52(m, 1H), 1.45(s, 3H), 1.43~1.32(m, 4H)

[0596] Example 1. (S)-quinuclidin-3-yl(5-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0597] 1,4-dioxane (1 ml) and water (0.5 ml) were added dropwise to a mixture of (S)-quinuclidene-3-yl (5-bromo-2,3-dihydro-1H-indene-1-yl)carbamate (30 mg, 0.082 mmol), 4-fluorophenylboronic acid (17.2 mg, 0.12 mmol), potassium phosphate (52.3 mg, 0.25 mmol), and tetrakis(triphenylphosphine)palladium (0) (9.4 mg, 10 mol%) prepared in Reference Example 1. The reaction mixture was refluxed and stirred overnight at 120°C. After cooling the reaction mixture to room temperature, water was added and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate / (methanol / ammonia water=1 / 1)= 9 / 1, v / v) to prepare the white solid title compound. (19 mg, yield: 64%)

[0598] 1 H-NMR (400MHz, CDCl3) δ 7.55(m, 2H), 7.42(m, 3H), 7.13(m, 2H), 5.29(m, 1H), 5.00(m, 1H), 4.81(br, 1H), 3.28(m, 1H), 3.05(m, 1H), 2.94(m, 3H), 2.82(m, 3H), 2.65(m, 1H), 2.06(m, 1H), 1.93~1.88(m, 2H), 1.71(m, 1H), 1.60(br, 1H), 1.42(br, 1H)

[0600] Examples 2 to 24

[0601] The title compounds of Examples 2 to 24 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl(5-bromo-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Reference Example 1 and the corresponding substituted-phenylboronic acid.

[0603] Example 2. (S)-quinuclidin-3-yl(5-(4-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0604] 1H-NMR (400MHz, CDCl3) δ 7.52(m, 2H), 7.42(m, 5H), 5.29(m, 1H), 5.01(m, 1H), 4.80(br, 1H), 3.28(m, 1H), 3.03(m, 1H), 2.85(m, 3H), 2.78~2.67(m, 4H), 2.09(m, 1H), 1.98(m, 1H), 1.87(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0606] Example 3. (S)-quinuclidin-3-yl(5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0607] 1 H-NMR (400MHz, CDCl3) δ 7.69(s, 4H), 7.47(m, 3H), 5.31(m, 1H), 5.01(m, 1H), 4.81(br, 1H), 3.31(m, 1H), 3.04(m, 1H), 2.94(m, 3H), 2.78(m, 4H), 2.03(m, 2H), 1,91(m, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0609] Example 4. (S)-quinuclidin-3-yl (5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0610] 1 H-NMR (400MHz, CDCl3) δ 7.58(d, 2H), 7.43(m, 3H), 7.29(d, 2H), 5.29(m, 1H), 4.99(m, 1H), 4.80(br, 1H), 3.31(m, 1H), 3.05(m, 1H), 2.95~2.75(m, 7H), 2.07(m, 1H), 1.84(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0612] Example 5. (S)-quinuclidin-3-yl(5-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0613] 1H-NMR (400MHz, CDCl3) δ 7.70(m, 1H), 7.45(m, 5H), 7.05(m, 1H), 5.28(m, 1H), 4.98(m, 1H), 4.80(br, 1H), 3.31(m, 1H), 2.94(m, 1H), 2.82~2.75(m, 7H), 2.09(m, 1H), 1.82(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H)

[0615] Example 6. (S)-quinuclidin-3-yl (5-(3-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0616] 1 H-NMR (400MHz, CDCl3) δ 7.57(s, 1H), 7.45(m, 4H), 7.34(m, 2H), 5.29(m, 1H), 4.98(m, 1H), 4.81(m, 1H), 3.30(m, 1H), 3.04(m, 1H), 2.95~2.66(m, 7H), 2.09(m, 1H), 1.82(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H)

[0618] Example 7. (S)-quinuclidin-3-yl (5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0619] 1 H-NMR (400MHz, CDCl3) δ 7.82(s, 1H), 7.76(d, 1H), 7.58(m, 2H), 7.47(m, 3H), 5.30(m, 1H), 4.98(m, 1H), 4.81(m, 1H), 3.30(m, 1H), 3.05(m, 1H), 3.05~2.68(m, 7H), 2.09(m, 1H), 1.91(br, 1H), 1.79(m, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.42(br, 1H)

[0621] Example 8. (S)-quinuclidin-3-yl(5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0622] 1H-NMR (400MHz, CDCl3) δ 7.52~7.42(m, 6H), 7.21(m, 1H), 5.29(m, 1H), 5.01(m, 1H), 4.81(m, 1H), 3.31(m, 1H), 3.04(m, 1H), 2.95~2.75(m, 7H), 2.09(m, 1H), 1.92(m, 1H), 1.84(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0624] Example 9. (S)-quinuclidin-3-yl (5-(2-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0625] 1 H-NMR (400MHz, CDCl3) δ 7.42(m, 3H), 7.28~7.16(m, 4H), 5.29(m, 1H), 4.98(m, 1H), 4.81(m, 1H), 3.29(m, 1H), 2.95(m, 1H), 2.89~2.66(m, 7H), 2.06(m, 1H), 1.83(m, 1H), 1.74(m, 2H), 1.60(br, 1H), 1.41(br, 1H)

[0627] Example 10. (S)-quinuclidin-3-yl (5-(2-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0628] 1 H-NMR (400MHz, CDCl3) δ 7.49(d, 1H), 7.41(d, 1H), 7.32(m, 5H), 5.32(m, 1H), 4.99(m, 1H), 4.81(br, 1H), 3.30(m, 1H), 3.03(m, 1H), 2.95~2.67(m, 7H), 2.06(m, 1H), 1.91(br, 1H), 1.83(br, 1H), 1.73(m, 1H), 1.61(br, 1H), 1.41(br, 1H)

[0630] Example 11. (S)-quinuclidin-3-yl (5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0631] 1H-NMR (400MHz, CDCl3) δ 7.75(d, 1H), 7.54(m, 1H), 7.49(m, 1H), 7.36(m, 4H), 5.31(m, 1H), 5.12(m, 1H), 4.81(br, 1H), 3.29(m, 1H), 3.01(m, 1H), 2.93~2.66(m, 7H), 2.09(br, 1H), 1.95(m, 1H), 1.88(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0633] Example 12. (S)-quinuclidin-3-yl(5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0634] 1 H-NMR (400MHz, CDCl3) δ 7.41(m, 6H), 7.26(m, 1H), 5.29(m, 1H), 5.04(m, 1H), 4.81(m, 1H), 3.31(m, 1H), 3.02(m, 1H), 2.94~2.76(m, 7H), 2.06(m, 1H), 1.84(m, 2H), 1.71(br, 1H), 1.61(br, 1H), 1.42(br, 1H)

[0636] Example 13. (S)-quinuclidin-3-yl (5-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0637] 1 H-NMR (400MHz, CDCl3) δ 7.46(m, 5H), 7.25(m, 2H), 5.29(m, 1H), 4.98(m, 1H), 4.80(m, 1H), 3.30(m, 1H), 3.04(m, 1H), 2.96~2.67(m, 7H), 2.40(s, 3H), 2.09(m, 1H), 1.85(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H)

[0639] Example 14. (S)-quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0640] 1H-NMR (400MHz, CDCl3) δ 7.58(m, 2H), 7.41(m, 3H), 7.20(d, 2H), 6.75~6.38(t, 1H), 5.29(m, 1H), 4.98(m, 1H), 4.80(m, 1H), 3.30(m, 1H), 2.95~2.66(m, 7H), 2.08(m, 1H), 1.85(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H)

[0642] Example 15. (S)-quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0643] 1 H-NMR (400MHz, CDCl3) δ 7.40(m, 4H), 7.23(m, 2H), 5.28(m, 1H), 5.00(m, 1H), 4.80(m, 1H), 3.30(m, 1H), 3.03(m, 1H), 2.94~2.66(m, 7H), 2.06(m, 1H), 1.87(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0645] Example 16. (S)-quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0646] 1 H-NMR (400MHz, CDCl3) δ 7.40(m, 4H), 6.96(m, 2H), 5.30(m, 1H), 5.00(m, 1H), 4.80(m, 1H), 3.28(m, 1H), 3.03(m, 1H), 2.95~2.66(m, 7H), 2.06(m, 1H), 1.82(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0648] Example 17. (S)-quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0649] 1H-NMR (400MHz, CDCl3) δ 7.42(m, 3H), 7.16(m, 3H), 5.31(m, 1H), 5.00(m, 1H), 4.81(m, 1H), 3.27(m, 1H), 3.04(m, 1H), 2.95~2.67(m, 7H), 2.09(m, 1H), 1.86(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0651] Example 18. (S)-quinuclidin-3-yl(5-(2,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0652] 1 H-NMR (400MHz, CDCl3) δ 7.41(m, 3H), 7.12(m, 2H), 7.01(m, 1H), 5.30(m, 1H), 5.02(m, 1H), 4.81(m, 1H), 3.30(m, 1H), 3.03(m, 1H), 2.95~2.66(m, 7H), 2.09(m, 1H), 1.89(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0654] Example 19. (S)-quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0655] 1 H-NMR (400MHz, CDCl3) δ 7.42(m, 3H), 7.09(d, 2H), 6.79(t, 1H), 5.29(m, 1H), 4.98(m, 1H), 4.81(m, 1H), 3.30(m, 1H), 3.04(m, 1H), 2.97~2.67(m, 7H), 2.09(m, 1H), 1.90(m, 1H), 1.82(m, 1H), 1.71(br, 1H), 1.61(br, 1H), 1.42(br, 1H)

[0657] Example 20. (S)-quinuclidin-3-yl (5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0658] 1H-NMR (400MHz, CDCl3) δ 7.43(m, 1H), 7.37(m, 2H), 7.13(m, 1H), 7.04(m, 1H), 5.29(m, 1H), 5.02(m, 1H), 4.80(m, 1H), 3.28(m, 1H), 3.03(m, 1H), 2.97~2.67(m, 7H), 2.06(m, 1H), 1.91(m, 1H), 1.84(m, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H)

[0660] Example 21. (S)-quinuclidin-3-yl (5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0661] 1 H-NMR (400MHz, CDCl3) δ 7.45(d, 1H), 7.36(s, 2H), 7.21(m, 1H), 7.02(m, 1H), 5.30(m, 1H), 5.01(m, 1H), 4.81(m, 1H), 3.28(m, 1H), 3.04(m, 1H), 2.95~2.67(m, 7H), 2.09(m, 1H), 1.90(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0663] Example 22. (S)-quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0664] 1 H-NMR (400MHz, CDCl3) δ 7.57(m, 1H), 7.49~7.42(m, 5H), 5.29(m, 1H), 5.00(m, 1H), 4.81(m, 1H), 3.28(m, 1H), 3.05(m, 1H), 2.89~2.67(m, 7H), 2.06(m, 1H), 1.83(m, 2H), 1.71(br, 1H), 1.61(br, 1H), 1.42(br, 1H)

[0666] Example 23. (S)-quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0667] 1H-NMR (400MHz, CDCl3) δ 7.66(s, 1H), 7.52(m, 2H), 7.42(m, 4H), 5.30(m, 1H), 4.98(m, 1H), 4.81(m, 1H), 3.29(m, 1H), 3.05(m, 1H), 2.97~2.67(m, 7H), 2.06(m, 1H), 1.93(m, 1H), 1.80(m, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.41(br, 1H)

[0669] Example 24. (S)-quinuclidin-3-yl(5-(2,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0670] 1 H-NMR (400MHz, CDCl3) δ 7.42(m, 1H), 7.32(m, 2H), 7.28(m, 3H), 5.31(m, 1H), 5.07(m, 1H), 4.80(m, 1H), 3.28(m, 1H), 3.03(m, 1H), 2.94~2.66(m, 7H), 2.06(m, 1H), 1.94(m, 1H), 1.87(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0672] Examples 25 to 48

[0673] The title compounds of Examples 25 to 48 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl(6-bromo-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Reference Example 2 and the corresponding substituted-phenylboronic acid.

[0675] Example 25. (S)-quinuclidin-3-yl (6-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0676] 1H-NMR (400MHz, CDCl3) δ 7.54(m, 3H), 7.42(m, 1H), 7.33(m, 1H), 7.13(t, 2H), 5.31(m, 1H), 5.00(m, 1H), 4.80(m, 1H), 3.28(m, 1H), 3.02(m, 1H), 3.00~2.72(m, 7H), 2.06(m, 2H), 1.93(m, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0678] Example 26. (S)-quinuclidin-3-yl (6-(4-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0679] 1 H-NMR (400MHz, CDCl3) δ 7.52(m, 3H), 7.40(m, 3H), 7.33(m, 1H), 5.31(m, 1H), 5.03(m, 1H), 4.80(br, 1H), 3.28(m, 1H), 3.00(m, 1H), 2.93~2.66(m, 7H), 1.91(m, 2H), 1.85(m, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.40(br, 1H)

[0681] Example 27. (S)-quinuclidin-3-yl (6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0682] 1 H-NMR (400MHz, CDCl3) δ 7.69(s, 4H), 7.55(s, 1H), 7.49(d, 1H), 7.36(d, 1H), 5.33(m, 1H), 5.04(m, 1H), 4.81(br, 1H), 3.28(m, 1H), 3.02(m, 1H), 2.94~2.67(m, 7H), 1.93(m, 2H), 1.83(m, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0684] Example 28. (S)-quinuclidin-3-yl (6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0685] 1H-NMR (400MHz, CDCl3) δ 7.60(d, 2H), 7.58(s, 1H), 7.46(d, 1H), 7.34(d, 1H), 7.28(d, 2H), 5.32(m, 1H), 5.04(m, 1H), 4.80(br, 1H), 3.28(m, 1H), 3.09(m, 1H), 2.93~2.86(m, 3H), 2.76(m, 4H), 1.97(m, 1H), 1.90(m, 1H), 1.83(m, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.39(br, 1H)

[0687] Example 29. (S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0688] 1 H-NMR (400MHz, CDCl3) δ 7.52(s, 1H), 7.46(d, 1H), 7.37(m, 3H), 7.28(m, 1H), 7.04(m, 1H), 5.31(m, 1H), 5.02(m, 1H), 4.81(br, 1H), 3.31(m, 1H), 3.04(m, 1H), 2.88(m, 3H), 2.77(m, 4H), 2.06(m, 1H), 1.93(m, 1H), 1.84(m, 1H), 1.68(m, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0690] Example 30. (S)-quinuclidin-3-yl (6-(3-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0691] 1 H-NMR (400MHz, CDCl3) δ 7.56~7.45(m, 4H), 7.37~7.28(m, 3H), 5.32(m, 1H), 5.02(m, 1H), 4.81(br, 1H), 3.27(m, 1H), 3.03(m, 1H), 2.93(m, 3H), 2.77(m, 4H), 1.92(m, 1H), 1.86(m, 1H), 1.85(m, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0693] Example 31. (S)-quinuclidin-3-yl(6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0694] 1 H-NMR (400MHz, CDCl3) δ 7.81(s, 1H), 7.77(m, 1H), 7.60~7.54(m, 3H), 7.50(m, 1H), 7.36(m, 1H), 5.33(m, 1H), 5.04(m, 1H), 4.80(br, 1H), 3.27(m, 1H), 3.03(m, 1H), 2.94(m, 3H), 2.76(m, 4H), 2.09(m, 1H), 1.96(m, 1H), 1.83(m, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0696] Example 32. (S)-quinuclidin-3-yl(6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0697] 1 H-NMR (400MHz, CDCl3) δ 7.51(d, 2H), 7.46(m, 2H), 7.42(s, 1H), 7.35(d, 1H), 7.21(d, 1H), 5.30(m, 1H), 5.05(m, 1H), 4.80(br, 1H), 3.30(m, 1H), 3.02(m, 1H), 2.87(m, 3H), 2.70(m, 4H), 2.08(m, 1H), 2.00(m, 1H), 1.90(m, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H)

[0699] Example 33. (S)-quinuclidin-3-yl(6-(2-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0700] 1 H-NMR (400MHz, CDCl3) δ 7.49(s, 1H), 7.43(s, 2H), 7.33(m, 2H), 7.22(m, 1H), 7.18(m, 1H), 5.31(m, 1H), 5.05(m, 1H), 4,78(br, 1H), 3.27(m, 1H), 3.03(m, 1H), 2,91(m, 3H), 2.75(m, 4H), 1.95(m, 2H), 1.88(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.39(br, 1H)

[0702] Example 34. (S)-quinuclidin-3-yl(6-(2-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0703] 1 H-NMR (400MHz, CDCl3) δ 7.48(d, 1H), 7.39(s, 1H), 7.32(m, 5H), 5.31(m, 1H), 5.07(m, 1H), 4.77(br, 1H), 3.24(m, 1H), 3.04(m, 1H), 2.94~2.71(m, 7H), 1.99(m, 1H), 1.90(m, 1H), 1.81(br, 1H), 1.68(br, 1H), 1.57(br, 1H), 1.38(br, 1H)

[0705] Example 35. (S)-quinuclidin-3-yl(6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0706] 1 H-NMR (400MHz, CDCl3) δ 7.76(d, 1H), 7.56(m, 1H), 7.49(m, 1H), 7.34(m, 1H), 7.27(m, 2H), 7.22(m, 1H), 5.31(m, 1H), 5.06(m, 1H), 4.76(br, 1H), 3.25(m, 1H), 2.94(m, 1H), 2.84(m, 2H), 2.75~2.71(m, 5H), 1.93(m, 1H), 1.91(m, 1H), 1.81(m, 1H), 1.67(m, 1H), 1.56(br, 1H), 1.37(br, 1H)

[0708] Example 36. (S)-quinuclidin-3-yl(6-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0709] 1 H-NMR (400MHz, CDCl3) δ 7.42(s, 2H), 7.36(m, 4H), 7.28(s, 1H), 5.32(m, 1H), 5.00(m, 1H), 4.78(br, 1H), 3.27(m, 1H), 3.04(m, 1H), 2.94(m, 3H), 2.72(m, 4H), 1.92(m, 2H), 1.82(m, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.39(br, 1H)

[0711] Example 37. (S)-quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0712] 1H-NMR (400MHz, CDCl3) δ 7.58(d, 2H), 7.50(s, 1H), 7.45(d, 1H), 7.33(d, 1H), 7.21(d, 2H), 6.75~6.38(t, 1H), 5.31(m, 1H), 5.02(m, 1H), 4.79(br, 1H), 3.28(m, 1H), 3.01(m, 1H), 2.90(m, 3H), 2.72(m, 4H), 2.06(m, 1H), 1.93(br, 1H), 1.83(m, 1H), 1.70(m, 1H), 1.58(m, 1H), 1.40(br, 1H)

[0714] Example 38. (S)-quinuclidin-3-yl (6-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0715] 1 H-NMR (400MHz, CDCl3) δ 7.53(s, 1H), 7.48(m, 3H), 7.32(d, 1H), 7.25(m, 2H), 5.31(m, 1H), 5.01(m, 1H), 4.80(br, 1H), 3.28(m, 1H), 3.00(m, 1H), 2.76(m, 3H), 2.68(m, 4H), 2.41(s, 3H), 2.06(m, 1H), 1.92~1.82(m, 2H), 1.69(m, 1H), 1.59(br, 1H), 1.40(br, 1H)

[0717] Example 39. (S)-quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0718] 1 H-NMR (400MHz, CDCl3) δ 7.47(s, 1H), 7.42(m, 2H), 7.37(m, 2H), 7.21(m, 1H), 5.31(m, 1H), 5.01(m, 1H), 4.80(br, 1H), 3.27(m, 1H), 3.02(m, 1H), 2.93(m, 3H), 2.76(m, 4H), 2.08(m, 1H), 1.93(m, 1H), 1.89(m, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H)

[0720] Example 40. (S)-quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0721] 1 H-NMR (400MHz, CDCl3) δ 7.50(s, 1H), 7.44(d, 1H), 7.32(d, 1H), 7.10(d, 2H), 6.79(m, 1H), 5.31(m, 1H), 5.03(m, 1H), 4.80(br, 1H), 3.28(m, 1H), 3.03(m, 1H), 2.93~2.67(m, 7H), 2.09(m, 1H), 1.92(m, 1H), 1.84(m, 1H), 1.70(m, 1H), 1.61(br, 1H), 1.40(br, 1H)

[0723] Example 41. (S)-quinuclidin-3-yl(6-(2,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0724] 1 H-NMR (400MHz, CDCl3) δ 7.47(s, 1H), 7.42(d, 1H), 7.34(m, 1H), 7.10(m, 2H), 7.01(m, 1H), 5.30(m, 1H), 5.04(m, 1H), 4.79(m, 1H), 3.26(m, 1H), 3.04(m, 1H), 2.87~2.75(m, 7H), 2.06(s, 1H), 1.93(m, 1H), 1.88(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.40(br, 1H)

[0726] Example 42. (S)-quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0727] 1 H-NMR (400MHz, CDCl3) δ 7.48(s, 1H), 7.43(m, 1H), 7.34(d, 1H), 7.15(m, 3H), 5.31(m, 1H), 5.04(m, 1H), 4.79(m, 1H), 3.26(m, 1H), 3.04(m, 1H), 2.94~2.67(m, 7H), 2.09(m, 1H), 1.93(m, 1H), 1.83(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.39(br, 1H)

[0729] Example 43. (S)-quinuclidin-3-yl(6-(2,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0730] 1 H-NMR (400MHz, CDCl3) δ 7.44(s, 1H), 7.40(m, 2H), 7.32(m, 1H), 6.94(m, 2H), 5.31(m, 1H), 5.02(m, 1H), 4.78(m, 1H), 3.27(m, 1H), 3.03(m, 1H), 2.93~2.66(m, 7H), 2.06(m, 1H), 1.89(m, 1H), 1.83(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.40(br, 1H)

[0732] Example 44. (S)-quinuclidin-3-yl (6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0733] 1 H-NMR (400MHz, CDCl3) δ 7.43(s, 1H), 7.36(m, 2H), 7.23(m, 1H), 7.04(m, 1H), 5.31(m, 1H), 5.02(m, 1H), 4.79(m, 1H), 3.26(m, 1H), 3.02(m, 1H), 2.93~2.72(m, 7H), 2.06(m, 1H), 1.88(m, 1H), 1.83(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H)

[0735] Example 45. (S)-quinuclidin-3-yl (6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0736] 1 H-NMR (400MHz, CDCl3) δ 7.44(s, 1H), 7.33(m, 2H), 7.13(m, 1H), 7.04(m, 1H), 5.31(m, 1H), 5.01(, 1H), 4.79(m, 1H), 3.29(m, 1H), 3.05(m, 1H), 2.96~2.67(m, 7H), 2.06(m, 1H), 1.88(m, 1H), 1.84(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.40(br, 1H)

[0738] Example 46. (S)-quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0739] 1 H-NMR (400MHz, CDCl3) δ 7.49(m, 2H), 7.32(m, 3H), 7.25(m, 1H), 5.32(m, 1H), 5.01(m, 1H), 4.79(m, 1H), 3.27(m, 1H), 3.04(m, 1H), 2.97~2.68(m, 7H), 2.06(m, 1H), 1.93(br, 1H), 1.88(m, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.39(br, 1H)

[0741] Example 47. (S)-quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0742] 1 H-NMR (400MHz, CDCl3) δ 7.66(s, 1H), 7.52(m, 2H), 7.44(m, 2H), 7.34(m, 1H), 5.31(m, 1H), 4.99(m, 1H), 4.81(br, 1H), 3.28(m, 1H), 3.01(m, 1H), 2.88(m, 3H), 2.77(m, 4H), 2.08(m, 1H), 1.89(m, 1H), 1.81(m, 1H), 1.71(m, 1H), 1.61(m, 1H), 1.42(br, 1H)

[0744] Example 48. (S)-quinuclidin-3-yl(6-(3,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0745] 1 H-NMR (400MHz, CDCl3) δ 7.48(m, 2H), 7.45(m, 2H), 7.34(m, 2H), 5.31(m, 1H), 5.00(m, 1H), 4.81(m, 1H), 3.30(m, 1H), 3.03(m, 1H), 2.95~2.68(m, 7H), 2.10(m, 1H), 1.91(m, 1H), 1.82(m, 1H), 1.70(m, 1H), 1.59(br, 1H), 1.41(br, 1H)

[0747] Examples 49 to 72

[0748] The title compounds of Examples 49 to 72 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl(6-bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Reference Example 3 and the corresponding substituted-phenylboronic acid.

[0750] Example 49. (S)-quinuclidin-3-yl (6-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0751] 1 H-NMR (400MHz, CDCl3) δ 7.54(m, 2H), 7.40(m, 2H), 7.24(t, 1H), 7.14(t, 2H), 5.01(m, 1H), 4.88(m, 1H), 4.81(m, 1H), 3.31(m, 1H), 2.81(m, 2H), 2.77(m, 5H), 2.10(m, 1H), 1.80(br, 1H), 1.75(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0753] Example 50. (S)-quinuclidin-3-yl (6-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0754] 1 H-NMR (400MHz, CDCl3) δ 7.50(m, 2H), 7.42(m, 3H), 7.26(m, 2H), 5.02(m, 1H), 4.89(m, 1H), 4.81(m, 1H), 3.30(m, 1H), 2.89(m, 2H), 2.77(m, 5H), 2.14(m, 1H), 1.86(br, 1H), 1.73(br, 1H), 1.62(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0756] Example 51. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0757] 1H-NMR (400MHz, CDCl3) δ 7.69(s, 4H), 7.45(m, 2H), 7.29(d, 1H), 5.04(m, 1H), 4.94(m, 1H), 4.80(m, 1H), 3.30(m, 1H), 2.91~2.66(m, 6H), 2.09(s, 1H), 2.00(br, 1H), 1.84(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(d, 3H), 0.99(d, 3H)

[0759] Example 52. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0760] 1 H-NMR (400MHz, CDCl3) δ 7.60(m, 2H), 7.41(m, 2H), 7.29(m, 3H), 5.03(m, 1H), 4.95(m, 1H), 4.80(m, 1H), 3.29(m, 1H), 2.88~2.66(m, 6H), 2.09(s, 1H), 2.00(br, 1H), 1.85(br, 1H), 1.71(br, 1H), 1.59(br, 1H), 1.42(br, 1H), 1.34(d, 3H), 0.99(d, 3H)

[0762] Example 53. (S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0763] 1 H-NMR (400MHz, CDCl3) δ 7.43(s, 2H), 7.39(m, 2H), 7.25(m, 2H), 7.04(t, 1H), 5.03(m, 1H), 4.89(m, 1H), 4.82(m, 1H), 3.30(m, 1H), 2.90(m, 2H), 2.78(m, 5H), 2.14(m, 1H), 1.85(br, 1H), 1.76(br, 1H), 1.61(br, 1H), 1.41(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0765] Example 54. (S)-quinuclidin-3-yl(6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0766] 1H-NMR (400MHz, CDCl3) δ 7.57(s, 1H), 7.43(m, 2H), 7.38(m, 1H), 7.33(t, 1H), 7.25(m, 2H), 5.03(m, 1H), 4.90(m, 1H), 4.83(m, 1H), 3.31(m, 1H), 2.83(m, 2H), 2.78(m, 5H), 2.14(m, 1H), 1.88(br, 1H), 1.75(br, 1H), 1.60(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0768] Example 55. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0769] 1 H-NMR (400MHz, CDCl3) δ 7.82(s, 1H), 7.76(m, 1H), 7.58(m, 2H), 7.45(m, 2H), 7.30(m, 1H), 5.04(m, 1H), 4.91(m, 1H), 4.81(m, 1H), 3.29(m, 1H), 2.87(m, 2H), 2.79(m, 5H), 2.14(m, 1H), 1.85(br, 1H), 1.76(br, 1H), 1.61(br, 1H), 1.42(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0771] Example 56. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0772] 1 H-NMR (400MHz, CDCl3) δ 7.48(m, 5H), 7.21(m, 2H), 5.04(m, 1H), 4.90(m, 1H), 4.82(m, 1H), 3.30(m, 1H), 2.89(m, 2H), 2.78(m, 5H), 2.11(m, 1H), 1.86(br, 1H), 1.75(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0774] Example 57. (S)-quinuclidin-3-yl (6-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0775] 1H-NMR (400MHz, CDCl3) δ 7.43(m, 2H), 7.31~7.16(m, 5H), 5.03(m, 1H), 4.91(m, 1H), 4.80(m, 1H), 3.30(m, 1H), 2.89(m, 2H), 2.78(m, 5H), 2.09(br, 1H), 1.85(br, 1H), 1.74(br, 1H), 1.59(br, 1H), 1.42(br, 1H), 1.31(d, 3H), 1.00(d, 3H)

[0777] Example 58. (S)-quinuclidin-3-yl (6-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0778] 1 H-NMR (400MHz, CDCl3) δ 7.48(m, 1H), 7.30(m, 6H), 5.04(m, 1H), 4.91(m, 1H), 4.79(br, 1H), 3.30(m, 1H), 2.87~2.75(m, 7H), 2.08(br, 1H), 1.79(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.42(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0780] Example 59. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0781] 1 H-NMR (400MHz, CDCl3) δ 7.76(d, 1H), 7.56(m, 1H), 7.49(m, 1H), 7.34(m, 1H), 7.20(m, 3H), 5.03(m, 1H), 4.89(m, 1H), 4.79(m, 1H), 3.26(m, 1H), 2.88~2.71(m, 7H), 2.09(m, 1H), 1.81(br, 1H), 1.71(br, 1H), 1.58(br, 1H), 1.41(br, 1H), 1.33(d, 3H), 0.99(d, 3H)

[0783] Example 60. (S)-quinuclidin-3-yl(2,2-dimethyl-6-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0784] 1H-NMR (400MHz, CDCl3) δ 7.44(m, 4H), 7.26(m, 3H), 5.02(m, 1H), 4.88(m, 1H), 4.82(m, 1H), 3.29(m, 1H), 2.89~2.77(m, 7H), 2.41(s, 3H), 2.08(br, 1H), 1.85(br, 1H), 1.75(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.31(d, 3H), 0.99(d, 3H)

[0786] Example 61. (S)-quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0787] 1 H-NMR (400MHz, CDCl3) δ 7.58(m, 2H), 7.50(m, 2H), 7.25(m, 1H), 7.20(m, 2H), 6.75~6.38(t, 1H), 5.03(m, 1H), 4.89(m, 1H), 4.81(m, 1H), 3.31(m, 1H), 2.90(m, 2H), 2.78(m, 5H), 2.11(m, 1H), 1.87(m, 1H), 1.71(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.31(d, 3H), 1.00(d, 3H)

[0789] Example 62. (S)-quinuclidin-3-yl(6-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0790] 1 H-NMR (400MHz, CDCl3) δ 7.69(m, 1H), 7.50(m, 1H), 7.38(m, 3H), 7.21(m, 1H), 5.02(m, 1H), 4.89(m, 1H), 4.83(m, 1H), 3.30(m, 1H), 2.86(m, 2H), 2.78(m, 5H), 2.14(m, 1H), 1.87(br, 1H), 1.73(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0792] Example 63. (S)-quinuclidin-3-yl(6-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0793] 1H-NMR (400MHz, CDCl3) δ 7.48(m, 3H), 7.28(m, 1H), 6.94(m, 2H), 5.03(m, 1H), 4.90(m, 1H), 4.81(m, 1H), 3.28(m, 1H), 2.88(m, 3H), 2.78(m, 4H), 2.14(m, 1H), 1.87(br, 1H), 1.75(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0795] Example 64. (S)-quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0796] 1 H-NMR (400MHz, CDCl3) δ 7.49(m, 1H), 7.39(m, 2H), 7.16(m, 3H), 5.04(m, 1H), 4.91(m, 1H), 4.88(m, 1H), 3.29(m, 1H), 2.86(m, 2H), 2.79(m, 5H), 2.10(m, 1H), 1.85(br, 1H), 1.73(br, 1H), 1.59(br, 1H), 1.43(br, 1H), 1.35(d, 3H), 0.99(d, 3H)

[0798] Example 65. (S)-quinuclidin-3-yl(6-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0799] 1 H-NMR (400MHz, CDCl3) δ 7.60(m, 1H), 7.39(m, 2H), 7.13(m, 2H), 7.02(m, 1H), 5.03(m, 1H), 4.91(m, 1H), 4.81(m, 1H), 3.31(m, 1H), 2.86(m, 2H), 2.78(m, 5H), 2.14(m, 1H), 1.87(br, 1H), 1.75(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0801] Example 66. (S)-quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0802] 1H-NMR (400MHz, CDCl3) δ 7.69~7.49(m, 1H), 7.42(m, 2H), 7.09(m, 2H), 6.79(m, 1H), 5.03(m, 1H), 4.90(m, 1H), 4.82(m, 1H), 3.31(m, 1H), 2.95(m, 2H), 2.78(m, 5H), 2.14(m, 1H), 1.86(br, 1H), 1.73(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0804] Example 67. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0805] 1 H-NMR (400MHz, CDCl3) δ 7.34(m, 1H), 7.28(m, 2H), 7.13(m, 1H), 7.07(m, 1H), 5.03(m, 1H), 4.91(m, 1H), 4.80(m, 1H), 3.29(m, 1H), 2.88(m, 2H), 2.79(m, 5H), 2.10(m, 1H), 1.85(br, 1H), 1.70(m, 1H), 1.61(br, 1H), 1.42(br, 1H), 1.31(d, 3H), 1.00(d, 3H)

[0807] Example 68. (S)-quinuclidin-3-yl(2,2-dimethyl-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0808] 1 H-NMR (400MHz, CDCl3) δ 7.34(m, 2H), 7.28(m, 2H), 7.04(m, 1H), 5.03(m, 1H), 4.90(m, 1H), 4.80(m, 1H), 3.28(m, 1H), 2.98(m, 2H), 2.78(m, 5H), 2.10(m, 1H), 1.85(br, 1H), 1.73(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 0.98(d, 3H)

[0810] Example 69. (S)-quinuclidin-3-yl(6-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0811] 1H-NMR (400MHz, CDCl3) δ 7.71(m, 1H), 7.66(m, 1H), 7.50(m, 1H), 7.45(m, 1H), 7.40(m, 1H), 7.33(m, 1H), 5.03(m, 1H), 4.89(m, 1H), 4.82(m, 1H), 3.30(m, 1H), 2.91~2.74(m, 7H), 2.14(m, 1H), 1.88(br, 1H), 1.72(br, 1H), 1.67(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0813] Example 70. (S)-quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0814] 1 H-NMR (400MHz, CDCl3) δ 7.69(m, 2H), 7.50(m, 2H), 7.39(m, 2H), 5.02(m, 1H), 4.89(m, 1H), 4.82(m, 1H), 3.31(m, 1H), 2.90(m, 2H), 2.78(m, 5H), 2.14(m, 1H), 1.87(br, 1H), 1.74(br, 1H), 1.62(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0816] Example 71. (S)-quinuclidin-3-yl(6-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0817] 1 H-NMR (400MHz, CDCl3) δ 7.41(m, 1H), 7.39(m, 1H), 7.28(m, 4H), 5.01(m, 1H), 4.92(m, 1H), 4.80(m, 1H), 3.27(m, 1H), 2.78(m, 7H), 2.09(m, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.41(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0819] Example 72. (S)-quinuclidin-3-yl(6-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0820] 1H-NMR (400MHz, CDCl3) δ 7.51(m, 2H), 7.40(m, 2H), 7.21(d, 1H), 6.99(m, 2H), 4.98(m, 1H), 4.84(m, 1H), 4.80(br, 1H), 4.17(m, 2H), 3.78(m, 2H), 3.47(s, 3H), 3.25(m, 1H), 2.88~2.71(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0822] Examples 73 to 275

[0823] The title compounds of Examples 73 to 275 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl (5-bromo-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Reference Example 4 and the corresponding substituted-boronic acid.

[0825] Example 73. (S)-quinuclidin-3-yl (5-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0826] 1 H-NMR (400MHz, CDCl3) δ 7.53(m, 2H), 7.40(m, 2H), 7.30(m, 1H), 7.13(t, 2H), 5.00(m, 1H), 4.88(m, 1H), 4.83(m, 1H), 3.29(m, 1H), 2.91~2.86(m, 2H), 2.82~2.75(m, 5H), 2.12(br, 1H), 1.82(br, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.31(d, 3H), 0.99(d, 3H)

[0828] Example 74. (S)-quinuclidin-3-yl (5-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0829] 1H-NMR (400MHz, CDCl3) δ 7.51(d, 2H), 7.41(d, 2H), 7.36(m, 2H), 7.31(m, 1H), 5.00(m, 1H), 4.90(m, 1H), 4.81(br, 1H), 3.31(m, 1H), 2.91~2.87(m, 2H), 2.82~2.75(m, 5H), 2.12(br, 1H), 1.86(br, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.31(d, 3H), 0.99(d, 3H)

[0831] Example 75. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0832] 1 H-NMR (400MHz, CDCl3) δ 7.67(s, 4H), 7.46~7.44(m, 1H), 7.42(s, 1H), 7.35~7.27(m, 1H), 5.02(m, 1H), 4.89(m, 1H), 4.82(m, 1H), 3.29(m, 1H), 2.90~2.85(m, 2H), 2.81~2.77(m, 5H), 2.13(br, 1H), 1.83(br, 1H), 1.72(br, 1H), 1.62(br, 1H), 1.46(br, 1H), 1.33(d, 3H), 1.01(d, 3H)

[0834] Example 76. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0835] 1 H-NMR (400MHz, CDCl3) δ 7.58(d, 2H), 7.42~7.37(m, 2H), 7.29(m, 3H), 5.01(m, 1H), 4.89(m, 1H), 4.82(m, 1H), 3.29(m, 1H), 2.90~2.87(m, 2H), 2.83~2.77(m, 5H), 2.12(br, 1H), 1.83(br, 1H), 1.73(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0837] Example 77. (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0838] 1 H-NMR (400MHz, CDCl3) δ 7.44~7.37(m, 3H), 7.34(m, 1H), 7.31(m, 2H), 7.04(t, 1H), 5.01(m, 1H), 4.90(m, 1H), 4.81(m, 1H), 3.29(m, 1H), 2.89~2.87(m, 2H), 2.83~2.75(m, 5H), 2.11(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0840] Example 78. (S)-quinuclidin-3-yl(5-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0841] 1 H-NMR (400MHz, CDCl3) δ 7.56(s, 1H), 7.45(m, 2H), 7.40(m, 2H), 7.34(m, 1H), 7.30(m, 1H), 5.01(m, 1H), 4.96(m, 1H), 4.81(m, 1H), 3.28(m, 1H), 2.89~2.86(m, 2H), 2.82~2.75(m, 5H), 2.11(br, 1H), 1.86(br, 1H), 1,72(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0843] Example 79. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0844] 1H-NMR (400MHz, CDCl3) δ 7.82(s, 1H), 7.75(d, 1H), 7.60~7.56(m, 2H), 7.43(m, 2H), 7.35(m, 1H), 5.03(m, 1H), 4.92(m, 1H), 4.81(br, 1H), 3.29(m, 1H), 2.89~2.84(m, 2H), 2.81~2.77(m, 5H), 2.12(br, 1H), 1.84(br, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.33(d, 3H), 1.00(d, 3H)

[0846] Example 80. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0847] 1 H-NMR (400MHz, CDCl3) δ 7.52~7.45(m, 1H), 7.41(m, 4H), 7.32(m, 1H), 7.20(d, 1H), 5.02(m, 1H), 4.89(m, 1H), 4.82(m, 1H), 3.28(m, 1H), 2.90~2.84(m, 2H), 2.79~2.76(m, 5H), 2.12(br, 1H), 1.82(br, 1H), 1.70(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0849] Example 81. (S)-quinuclidin-3-yl (5-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0850] 1 H-NMR (400MHz, CDCl3) δ 7.43~7.37(m, 3H), 7.33~7.28(m, 2H), 7.23(m, 1H), 7.18(m, 1H), 5.01(m, 1H), 4.91(m, 1H), 4.81(br, 1H), 3.30(m, 1H), 2.89~2.87(m, 2H), 2.83~2.76(m, 5H), 2.12(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0852] Example 82. (S)-quinuclidin-3-yl (5-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0853] 1 H-NMR (400MHz, CDCl3) δ 7.47(d, 1H), 7.33~7.25(m, 6H), 5.02(m, 1H), 4.94(m, 1H), 4.82(br, 1H), 3.28(m, 1H), 2.89~2.87(m, 2H), 2.83~2.75(m, 5H), 2.13(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.34(d, 3H), 1.00(d, 3H)

[0855] Example 83. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0856] 1 H-NMR (400MHz, CDCl3) δ 7.74(d, 1H), 7.55(m, 1H), 7.48(m, 1H), 7.33(d, 1H), 7.27(m, 1H), 7.17(m, 1H), 7.14(s, 1H), 5.03(m, 2H), 4.82(br, 1H), 3.31(m, 1H), 2.89~2.85(m, 2H), 2.82~2.73(m, 5H), 2.11(br, 1H), 1.85(br, 1H), 1.71(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0858] Example 84. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0859] 1H-NMR (400MHz, CDCl3) δ 7.42(m, 1H), 7.36(m, 3H), 7.27(m, 3H), 5.03(m, 1H), 4.94(m, 1H), 4.82(m, 1H), 3.28(m, 1H), 2.90~2.87(m 2H), 2.83~2.75(m, 5H), 2.12(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.62(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0861] Example 85. (S)-quinuclidin-3-yl (2,2-dimethyl-5-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0862] 1 H-NMR (400MHz, CDCl3) δ 7.49(d, 2H), 7.42(m, 2H), 7.26(m, 3H), 5.00(m, 1H), 4.89(m, 1H), 4.80(m, 1H), 3.29(m, 1H), 2.89~2.85(m, 2H), 2.82~2.75(m, 5H), 2.41(s, 3H), 2.11(br, 1H), 1.82(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.44(br, 1H), 1.31(d, 3H), 1.00(d, 3H)

[0864] Example 86. (S)-quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0865] 1 H-NMR (400MHz, CDCl3) δ 7.56(d, 2H), 7.37(m, 2H), 7.32(m, 1H), 7.19(d, 2H), 6.75~6.38(t, 1H), 4.99(m, 1H), 2.90(m, 1H), 4.82(br, 1H), 3.29(m, 1H), 2.90~2.87(m, 2H), 2.83~2.79(m, 5H), 2.11(br, 1H), 1.82(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.44(br, 1H), 1.32(s, 3H), 0.99(d, 3H)

[0867] Example 87. (S)-quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0868] 1 H-NMR (400MHz, CDCl3) δ 7.37(m, 3H), 7.29(m, 2H), 7.23(m, 1H), 5.01(m, 1H), 4.90(m, 1H), 4.82(m, 1H), 3.32(m, 1H), 2.89~2.86(m, 2H), 2.82~2.75(m, 5H), 2.11(m, 1H), 1.90(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.34(d, 3H), 0.99(d, 3H)

[0870] Example 88. (S)-quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0871] 1 H-NMR (400MHz, CDCl3) δ 7.36(m, 3H), 7.12(m, 2H), 6.99(m, 1H), 5.02(m, 1H), 4.90(m, 1H), 4.80(m, 1H), 3.29(m, 1H), 2.89~2.87(m, 2H), 2.83~2.75(m, 5H), 2.11(m, 1H), 1.86(br, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 1.00(d, 3H)

[0873] Example 89. (S)-quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0874] 1 H-NMR (400MHz, CDCl3) δ 7.40(m, 1H), 7.35(m, 3H), 6.95(m, 2H), 5.01(m, 1H), 4.91(m, 1H), 4.80(m, 1H), 3.29(m, 1H), 2.89~2.86(m, 2H), 2.83~2.75(m, 5H), 2.11(m, 1H), 1.85(br, 1H), 1.75(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0876] Example 90. (S)-quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0877] 1 H-NMR (400MHz, CDCl3) δ 7.50(m, 3H), 7.10(m, 2H), 6.78((m, 1H), 5.02(m, 1H), 4.89(m, 1H), 4.81(m, 1H), 3.30(m, 1H), 2.90~2.87(m, 2H), 2.83~2.75(m, 5H), 2.12(m, 1H), 1.86(br, 1H), 1.75(br, 1H), 1.61(br, 1H), 1.45(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0879] Example 91. (S)-quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0880] 1 H-NMR (400MHz, CDCl3) δ 7.38~7.28(m, 3H), 7.16(m, 3H), 5.02(m, 1H), 4.91(m, 1H), 4.82(m, 1H), 3.30(m, 1H), 2.88(m, 2H), 2.83~2.76(m, 5H), 2.12(m, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0882] Example 92. (S)-quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0883] 1 H-NMR (400MHz, CDCl3) δ 7.71(m, 2H), 7.56(m, 1H), 7.48(m, 2H), 7.39(m, 1H), 5.03(m, 1H), 4.86(m, 2H), 3.31(m, 1H), 2.91(m, 2H), 2.86~2.78(m, 5H), 2.13(m, 1H), 1.86(br, 1H), 1.75(br, 1H), 1.68(br, 1H), 1.46(br, 1H), 1.32(d 3H), 0.99(d, 3H)

[0885] Example 93. (S)-quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0886] 1 H-NMR (400MHz, CDCl3) δ 7.41(d, 1H), 7.33~7.23(m, 5H), 5.03(m, 1H), 4.94(m, 1H), 4.82(m, 1H), 3.28(m, 1H), 2.90~2.87(m, 2H), 2.83~2.75(m, 5H), 2.11(m, 1H), 1.85(br, 1H), 1.71(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0888] Example 94. (S)-quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0889] 1 H-NMR (400MHz, CDCl3) δ 7.50(m, 1H), 7.45(m, 1H), 7.39(s, 2H), 7.35(d, 2H), 5.02(m, 1H), 4.87(m, 2H), 3.30(m, 1H), 2.90~2.82(m, 2H), 2.83~2.79(m, 5H), 2.13(br, 1H), 2.06(br, 1H), 1.88(br, 1H), 1.69(br, 1H), 1.48(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0891] Example 95. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0892] 1 H-NMR (400MHz, CDCl3) δ 7.31(m, 3H), 7.13(m, 1H), 7.06(m, 1H), 5.02(m, 1H), 4.90(m, 1H), 4.83(m, 1H), 3.30(m, 1H), 2.94~2.88(m, 2H), 2.83~2.76(m, 5H), 2.12(m, 1H), 1.87(br, 1H), 1.73(m, 1H), 1.61(br, 1H), 1.47(br, 1H), 1.31(d, 3H), 1.00(d, 3H)

[0894] Example 96. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0895] 1 H-NMR (400MHz, CDCl3) δ 7.32(m, 3H), 7.23(m, 1H), 7.03(m, 1H), 5.02(m, 1H), 4.89(m, 1H), 4.81(m, 1H), 3.32(m, 1H), 2.91~2.87(m, 2H), 2.83~2.75(m, 5H), 2.11(m, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.32(d, 3H), 0.99(d, 3H)

[0897] Example 97. (S)-quinuclidin-3-yl (5-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0898] 1 H-NMR (400MHz, CDCl3) δ 7.49(d, 2H), 7.39(m, 1H), 7.36(s, 1H), 7.27(m, 1H), 7.00(d, 2H), 4.98(m, 1H), 4.84(m, 1H), 4.80(br, 1H), 4.18(m, 2H), 3.78(m, 2H), 3.48(s, 3H), 3.25(m, 1H), 2.90~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0900] Example 98. (S)-quinuclidin-3-yl(5-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0901] 1H-NMR (400MHz, CDCl3) δ 7.42(m, 1H), 7.36(s, 1H), 7.31~7.27(m, 2H), 7.18(m, 2H), 6.91(d, 1H), 4.99(m, 1H), 4.84~4.80(m, 2H), 4.18(m, 2H), 3.79(m, 2H), 3.48(s, 3H), 3.25(m, 1H), 2.90~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0903] Example 99. (S)-quinuclidin-3-yl (5-(2-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0904] 1 H-NMR (400MHz, CDCl3) δ 7.40(m, 2H), 7.32~7.27(m, 3H), 7.04~7.98(m, 2H), 4.99(m, 1H), 4.84(m, 1H), 4.80(m, 1H), 4.10(m, 2H), 3.68(m, 2H), 3.38(s, 3H), 3.25(m, 1H), 2.90~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0906] Example 100. (S)-quinuclidin-3-yl (5-(4-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0907] 1H-NMR (400MHz, CDCl3) δ 7.51(d, 2H), 7.38(m, 1H), 7.35(s, 1H), 7.27(m, 1H), 7.10(d, 2H), 5.22(s, 2H), 4.99(m, 1H), 4.84(m, 1H), 4.80(m, 1H), 3.31(s, 3H), 3.25(m, 1H), 2.90~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0909] Example 101. (S)-quinuclidin-3-yl (5-(3-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0910] 1 H-NMR (400MHz, MeOD) δ 7.41(m, 2H), 7.28(m, 1H), 7.26(m, 1H), 7.05(d, 1H), 7.00(s, 1H), 6.75(d, 1H), 5.07(br, 1H), 4.87(s, 2H), 3.72(m, 1H), 3.67(s, 3H), 3.39(m, 2H), 3.39~3.29(m, 5H), 2.81(s, 2H), 2.45(m, 1H), 2.30(br, 1H), 2.10(br, 1H), 1.93(br, 1H), 1.24(d, 3H), 0.98(d, 3H)

[0912] Example 102. (S)-quinuclidin-3-yl (5-(2-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0913] 1H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.35(m, 4H), 7.21(m, 1H), 7.09(m, 1H), 5.12(s, 2H), 4.99(m, 1H), 4.84(m, 1H), 4.80(m, 1H), 3.41(s, 3H), 3.25(m, 1H), 2.90~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0915] Example 103. (S)-quinuclidin-3-yl (5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0916] 1 H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.39(s, 1H), 7.31~7.27(m, 2H), 7.15(d, 1H), 7.10(s, 1H), 6.89(d, 1H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 3.87(s, 3H), 3.25(m, 1H), 2.90~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0918] Example 104. (S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0919] 1H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.39(s, 1H), 7.31~7.27(m, 2H), 7.15(d, 1H), 7.10(s, 1H), 6.89(d, 1H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.11(m, 2H), 3.25(m, 1H), 2.90~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.45(t, 4H), 1.29(m, 3H), 0.98(m, 3H)

[0921] Example 105. (S)-quinuclidin-3-yl (5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0922] 1 H-NMR (400MHz, CDCl3) δ 7.43(m, 1H), 7.39(s, 1H), 7.35~7.27(m, 2H), 7.14(d, 1H), 7.10(s, 1H), 6.88(d, 1H), 5.00(m, 1H), 4.85(m, 1H), 4.80(br, 1H), 4.62(m, 1H), 3.25(m, 1H), 2.90~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.38(d, 6H), 1.29(m, 3H), 0.98(m, 3H)

[0924] Example 106. (S)-quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0925] 1H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.40(s, 1H), 7.32~7.27(m, 2H), 6.91(m, 2H), 6.74(d, 1H), 4.99(m, 1H), 4.86(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 3.01(s, 6H), 2.92~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.97(m, 3H)

[0927] Example 107. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-(methylthio)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0928] 1 H-NMR (400MHz, CDCl3) δ 7.45(s, 1H), 7.41~7.23(m, 6H), 4.99(m, 1H), 4.87(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.92~2.75(m, 7H), 2.54(s, 3H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[0930] Example 108. (S)-quinuclidin-3-yl (5-(3-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0931] 1 H-NMR (400MHz, CDCl3) δ 7.45(d, 1H), 7.42(s, 2H), 7.40~7.28(m, 3H), 7.19(d, 1H), 5.00(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.92~2.75(m, 7H), 2.70(m, 2H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(t, 3H), 1.29(m, 3H), 0.98(m, 3H)

[0933] Example 109. (S)-quinuclidin-3-yl (5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0934] 1 H-NMR (400MHz, CDCl3) δ 7.43~7.34(m, 5H), 7.28(m, 1H), 7.22(d, 1H), 5.00(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.98(m, 1H), 2.92~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 9H), 0.98(m, 3H)

[0936] Example 110. (S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0937] 1 H-NMR (400MHz, CDCl3) δ 7.58(s, 1H), 7.44(d, 1H), 7.38(s, 4H), 7.28(m, 1H), 5.00(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.92~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.38(s, 9H), 1.29(m, 3H), 0.98(m, 3H)

[0939] Example 111. (S)-quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0940] 1 H-NMR (400MHz, CDCl3) δ 7.34~7.27(m, 3H), 7.25(m, 2H), 7.10(d, 1H), 5.00(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.92~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0942] Example 112. (S)-quinuclidin-3-yl (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0943] 1 H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.36(s, 1H), 7.25(m, 1H), 7.09(s, 1H), 7.05(d, 1H), 6.91(d, 1H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.29(s, 4H), 3.25(m, 1H), 2.92~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.29(m, 3H), 0.97(m, 3H)

[0945] Example 113. (S)-quinuclidin-3-yl (5-(2,3-dihydrobenzofuran-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0946] 1 H-NMR (400MHz, CDCl3) δ 7.41(s, 1H), 7.36~7.30(m, 3H), 7.25(m, 1H), 6.84(d, 1H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.62(t, 2H), 3.25(m, 3H), 2.92~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.29(m, 3H), 0.97(m, 3H)

[0948] Example 114. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-(2-morpholinothoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0949] 1H-NMR (400MHz, CDCl3) δ 7.43(d, 1H), 7.39(s, 1H), 7.38~7.30(m, 2H), 7.17(d, 1H), 7.11(s, 1H), 6.89(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.19(t, 2H), 3.75(m, 4H), 3.25(m, 3H), 2.92~2.73(m, 9H), 2.60(m, 4H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0951] Example 115. (S)-quinuclidin-3-yl (5-(4-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0952] 1 H-NMR (400MHz, CDCl3) δ 7.52(d, 2H), 7.35(m, 2H), 7.26(m, 1H), 7.00(d, 2H), 4.99(m, 1H), 4.87(m, 2H), 4.81(m, 1H), 4.71(br, 1H), 4.31~4.22(m, 2H), 3.25(m, 3H), 2.90~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.59(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0954] Example 116. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-(2,2,2-trifluoroethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0955] 1H-NMR (400MHz, CDCl3) δ 7.43~7.36(m, 3H), 7.31~7.25(m, 2H), 7.15(s, 1H), 6.91(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.42(q, 2H), 3.25(m, 3H), 2.92~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0957] Example 117. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-(2-morpholinothoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0958] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.39(m, 2H), 7.24(m, 1H), 6.97(d, 2H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.16(t, 2H), 3.76(m, 4H), 3.25(m, 3H), 2.92~2.73(m, 9H), 2.60(m, 4H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0960] Example 118. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethyl)pyridine-4-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0961] 1 H-NMR (400MHz, CDCl3) δ 8.76(d, 1H), 7.87(s, 1H), 7.67(d, 1H), 7.49(m, 2H), 7.37(m, 1H), 5.00(m, 1H), 4.93(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.92~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[0963] Example 119. (S)-quinuclidin-3-yl (5-(2,5-dichloropyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0964] 1 H-NMR (400MHz, CDCl3) δ 8.44(s, 1H), 7.30(m, 1H), 7.19(m, 3H), 4.96(m, 1H), 4.86(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.92~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[0966] Example 120 . (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[0967] 1 H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.33(s, 1H), 7.25(m, 1H), 7.07(d, 1H), 7.03(s, 1H), 6.72(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.33(m, 2H), 3.29(m, 2H), 3.25(m, 1H), 2.92(s, 3H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0969] Example 121. (S)-quinuclidin-3-yl (5-(2-chloro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0970] 1H-NMR (400MHz, CDCl3) δ 7.36(d, 1H), 7.28(m, 3H), 6.86(m, 1H), 6.81(m, 1H), 5.00(m, 2H), 4.80(br, 1H), 3.81(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(m, 3H), 0.99(m, 3H)

[0972] Example 122. (S)-quinuclidin-3-yl (5-(3-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0973] 1 H-NMR (400MHz, CDCl3) δ 7.59(d, 1H), 7.44(d, 1H), 7.37(m, 1H), 7.25(m, 1H), 6.98(d, 1H), 4.98(m, 2H), 4.80(br, 1H), 3.94(s, 3H), 3.25(m, 1H), 2.88~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[0975] Example 123. (S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0976] 1 H-NMR (400MHz, CDCl3) δ 7.24(m, 1H), 7.22(m, 3H), 7.01(s, 1H), 6.85(d, 1H), 4.99(s, 2H), 4.79(br, 1H), 3.84(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(m, 3H), 0.97(m, 3H)

[0978] Example 124. (S)-quinuclidin-3-yl (5-(2-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0979] 1 H-NMR (400MHz, CDCl3) δ 7.31~7.22(m, 4H), 6.94(d, 2H), 4.99(s, 2H), 4.79(br, 1H), 3.95(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[0981] Example 125. (S)-quinuclidin-3-yl (5-(4-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0982] 1 H-NMR (400MHz, CDCl3) δ 7.41~7.37(m, 3H), 7.27(m, 1H), 7.08(m, 2H), 5.00(m, 1H), 4.91(m, 1H), 4.80(br, 1H), 3.97(s, 3H), 3.25(m, 1H), 2.91~2.75(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0984] Example 126. (S)-quinuclidin-3-yl (5-(2,3-dichloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0985] 1 H-NMR (400MHz, CDCl3) δ 7.27(m, 1H), 7.21(m, 1H), 7.19(d, 2H), 6.90(d, 1H), 5.00(s, 2H), 4.80(br, 1H), 3.95(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0987] Example 127. (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0988] 1H-NMR (400MHz, CDCl3) δ 7.59(s, 1H), 7.39(m, 2H), 7.33(s, 1H), 7.26(m, 1H), 7.00(d, 1H), 4.96(m, 2H), 4.79(br, 1H), 4.60(m, 1H), 3.25(m, 1H), 2.88~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.38(d, 6H), 1.30(m, 3H), 0.97(m, 3H)

[0990] Example 128. (S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0991] 1 H-NMR (400MHz, CDCl3) δ 7.35~7.27(m, 4H), 6.77(d, 1H), 6.69(d, 1H), 4.97(m, 2H), 4.80(br, 1H), 3.84(s, 3H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.38(d, 6H), 1.30(m, 3H), 0.98(m, 3H)

[0993] Example 129. (S)-quinuclidin-3-yl (5-(3-(dimethylamino)-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0994] 1 H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.30(s, 1H), 7.25(m, 1H), 7.09(s, 1H), 7.04(m, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.90(s, 6H), 2.89~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.38(d, 6H), 1.30(m, 3H), 0.98(m, 3H)

[0996] Example 130. (S)-quinuclidin-3-yl (5-(chroman-6-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[0997] 1 H-NMR (400MHz, CDCl3) δ 7.37(m, 1H), 7.33(s, 1H), 7.25(m, 3H), 6.85(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 4.23(m, 2H), 3.25(m, 1H), 2.89~2.74(m, 9H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[0999] Example 131. (S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1000] 1 H-NMR (400MHz, CDCl3) δ 7.47(d, 2H), 7.42(m, 1H), 7.38(s, 1H), 7.25(m, 1H), 7.13(d, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.89~2.74(m, 7H), 2.10(br, 1H), 1.91(m, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 6H), 0.74(m, 2H)

[1002] Example 132. (S)-quinuclidin-3-yl (5-(4-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1003] 1H-NMR (400MHz, CDCl3) δ 7.48(d, 2H), 7.39(m, 1H), 7.36(s, 1H), 7.21(m, 2H), 6.80(d, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 3.00(s, 6H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1005] Example 133. (S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1006] 1 H-NMR (400MHz, CDCl3) δ 7.38~7.32(m, 2H), 7.27(m, 3H), 6.99(t, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 4.15(m, 2H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.48(t, 3H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1008] Example 134. (S)-quinuclidin-3-yl (5-(4-methoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1009] 1 H-NMR (400MHz, CDCl3) δ 7.76(s, 1H), 7.69(d, 1H), 7.31(m, 2H), 7.27(m, 1H), 7.07(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 4.95(s, 3H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[1011] Example 135. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1012] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.38(m, 1H), 7.35(s, 1H), 7.26(m, 1H), 6.96(d, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.96(q, 2H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.84(m, 2H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 1.06(t, 3H), 0.98(m, 3H)

[1014] Example 136. (S)-quinuclidin-3-yl(5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1015] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.39(m, 1H), 7.36(s, 1H), 7.26(m, 1H), 6.96(d, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.77(d, 2H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(m, 2H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 1.05(d, 6H), 0.98(m, 3H)

[1017] Example 137. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(thiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1018] 1H-NMR (400MHz, CDCl3) δ 7.46~7.41(m, 3H), 7.38(m, 2H), 7.21(m, 1H), 4.98(m, 1H), 4.87(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[1020] Example 138. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-methylthiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1021] 1 H-NMR (400MHz, CDCl3) δ 7.28~7.16(m, 4H), 7.02(s, 1H), 4.99(m, 1H), 4.87(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.26(s, 3H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[1023] Example 139. (S)-quinuclidin-3-yl (5-(3-(2-(dimethylamino)ethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1024] 1 H-NMR (400MHz, CDCl3) δ 7.28(m, 1H), 7.24(m, 4H), 6.94(m, 2H), 4.99(m, 1H), 4.87(m, 1H), 4.80(br, 1H), 4.07(m, 2H), 3.25(m, 1H), 2.89~2.73(m, 9H), 2.35(s, 6H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 0.98(m, 3H)

[1026] Example 140. (S)-quinuclidin-3-yl (5-(isoquinoline-8-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1027] 1H-NMR (400MHz, CDCl3) δ 9.31(s, 1H), 8.51(d, 1H), 7.82(d, 1H), 7.72(m, 2H), 7.52(d, 1H), 7.36(m, 3H), 5.24(m, 1H), 5.07(m, 1H), 4.81(m, 1H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.35(m, 3H), 0.98(m, 3H)

[1029] Example 141. (S)-quinuclidin-3-yl (5-(isoquinoline-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1030] 1 H-NMR (400MHz, CDCl3) δ 9.31(s, 1H), 8.47(d, 1H), 7.99(d, 1H), 7.71(d, 1H), 7.65(m, 2H), 7.39~7.27(m, 3H), 5.05(m, 2H), 4.82(m, 1H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.34(m, 3H), 0.98(m, 3H)

[1032] Example 142. (S)-quinuclidin-3-yl (5-(isoquinoline-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1033] 1 H-NMR (400MHz, CDCl3) δ 9.25(s, 1H), 8.44(s, 1H), 8.04(d, 1H), 7.91(d, 1H), 7.65(m, 2H), 7.38(m, 3H), 5.09(m, 2H), 4.82(m, 1H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.35(m, 3H), 0.99(m, 3H)

[1035] Example 143. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1036] 1 H-NMR (400MHz, CDCl3) δ 9.16(s, 1H), 8.30(s, 1H), 8.14(d, 1H), 7.88(d, 1H), 7.72(m, 1H), 7.61~7.53(m, 3H), 7.39(m, 1H), 5.05~4.94(m, 2H), 4.82(m, 1H), 3.25(m, 1H), 2.91~2.77(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.34(m, 3H), 1.00(m, 3H)

[1038] Example 144. (S)-quinuclidin-3-yl (5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1039] 1 H-NMR (400MHz, CDCl3) δ 7.48(d, 1H), 7.37(m, 1H), 7.35(s, 1H), 7.25(m, 1H), 6.95(d, 2H), 4.98(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 4.61(m, 1H), 3.25(m, 1H), 2.89~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.36(d, 6H), 1.30(m, 3H), 0.98(m, 3H)

[1041] Example 145. (S)-quinuclidin-3-yl (5-(2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1042] 1H-NMR (400MHz, CDCl3) δ 7.42(m, 1H), 7.36(s, 1H), 7.30~7.21(m, 3H), 7.01(m, 2H), 4.98(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 4.42(m, 1H), 3.25(m, 1H), 2.91~2.72(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 1.26(d, 6H), 0.98(m, 3H)

[1044] Example 146. (S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1045] 1 H-NMR (400MHz, CDCl3) δ 7.53(m, 2H), 7.47(m, 2H), 7.26(m, 2H), 7.24(m, 1H), 4.98(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.91~2.72(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.36(s, 9H), 1.29(m, 3H), 0.98(m, 3H)

[1047] Example 147. (S)-quinuclidin-3-yl (5-(4-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1048] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.43(m, 1H), 7.38(s, 1H), 7.27(m, 3H), 4.98(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.91~2.72(m, 7H), 2.69(m, 2H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 6H), 0.98(m, 3H)

[1050] Example 148. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-morpholinophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1051] 1 H-NMR (400MHz, CDCl3) δ 7.51(d, 2H), 7.39(m, 1H), 7.36(s, 1H), 7.27(m, 1H), 6.97(d, 2H), 4.98(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 3.89(m, 4H), 3.25(m, 1H), 3.21(m, 4H), 2.91~2.72(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1053] Example 149. (S)-quinuclidin-3-yl (5-(4-(methoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1054] 1 H-NMR (400MHz, CDCl3) δ 7.56(d, 2H), 7.42(m, 4H), 7.27(m, 1H), 4.98(m, 1H), 4.88(m, 1H), 4.80(br, 1H), 4.50(s, 2H), 3.42(s, 3H), 3.25(m, 1H), 2.89~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1056] Example 150. (S)-quinuclidin-3-yl (5-(4-(2,2-difluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1057] 1H-NMR (400MHz, CDCl3) δ 7.53(d, 2H), 7.39(m, 2H), 7.27(m, 1H), 6.99(d, 2H), 6.25~5.98(t, 1H), 4.98(m, 2H), 4.79(br, 1H), 4.21(m, 2H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 0.97(m, 3H)

[1059] Example 151. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-methyl-4-morpholinophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1060] 1 H-NMR (400MHz, CDCl3) δ 7.40~7.36(m, 4H), 7.24(m, 1H), 7.07(d, 1H), 4.95(m, 2H), 4.78(br, 1H), 3.89(m, 4H), 3.25(m, 1H), 2.95(m, 4H), 2.91~2.73(m, 7H), 2.38(s, 3H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1062] Example 152. (S)-quinuclidin-3-yl (5-(3-fluoro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1063] 1 H-NMR (400MHz, CDCl3) δ 7.34(m, 2H), 7.26(m, 2H), 7.23(m, 1H), 6.98(t, 1H), 4.96(m, 1H), 4.91(br, 1H), 4.78(br, 1H), 3.90(m, 4H), 3.25(m, 1H), 3.14(m, 4H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1065] Example 153. (S)-quinuclidin-3-yl (5-(3-chloro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1066] 1 H-NMR (400MHz, CDCl3) δ 7.60(s, 1H), 7.45(d, 1H), 7.36(m, 2H), 7.26(m, 1H), 7.10(d, 1H), 4.99(m, 1H), 4.91(br, 1H), 4.78(br, 1H), 3.90(m, 4H), 3.25(m, 1H), 3.09(m, 4H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1068] Example 154. (S)-quinuclidin-3-yl (5-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1069] 1 H-NMR (400MHz, CDCl3) δ 7.37(m, 1H), 7.34(s, 1H), 7.24(m, 1H), 7.20(s, 1H), 7.15(d, 1H), 7.02(d, 1H), 4.99(m, 1H), 4.91(br, 1H), 4.78(br, 1H), 4.23(m, 4H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.22(m, 2H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 0.97(m, 3H)

[1071] Example 155. (S)-quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1072] 1H-NMR (400MHz, CDCl3) δ 7.71(m, 2H), 7.54(m, 2H), 7.41(m, 2H), 7.30(m, 1H), 6.85~6.57(t, 1H), 5.01(m, 1H), 4.92(br, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 0.97(m, 3H)

[1074] Example 156. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-8-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1075] 1 H-NMR (400MHz, CDCl3) δ 8.96(m, 1H), 8.22(d, 1H), 7.84(d, 1H), 7.72(m, 1H), 7.62(d, 1H), 7.58(m, 1H), 7.50(s, 1H), 7.44(d, 1H), 7.35(d, 1H), 5.00(m, 1H), 4.92(br, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.28(m, 3H), 0.95(m, 3H)

[1077] Example 157. (S)-quinuclidin-3-yl (5-(benzofuran-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1078] 1H-NMR (400MHz, CDCl3) δ 7.84(d, 1H), 7.78(s, 1H), 7.55(d, 1H), 7.49(m, 1H), 7.45(s, 1H), 7.34(m, 3H), 5.02(m, 1H), 4.92(br, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.32(m, 3H), 0.97(m, 3H)

[1080] Example 158. (S)-quinuclidin-3-yl (5-(benzofuran-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1081] 1 H-NMR (400MHz, CDCl3) δ 7.73(d, 1H), 7.71(s, 1H), 7.59(d, 1H), 7.53(d, 1H), 7.26(m, 3H), 5.02(m, 1H), 4.92(br, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 0.97(m, 3H)

[1083] Example 159. (S)-quinuclidin-3-yl (5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1084] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.38(m, 1H), 7.35(s, 1H), 7.26(m, 1H), 6.97(d, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.85(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1086] Example 160. (S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1087] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.38(m, 1H), 7.35(s, 1H), 7.26(m, 1H), 6.95(d, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 4.08(m, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.42(t, 3H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1089] Example 161. (S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1090] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.44(m, 1H), 7.39(s, 1H), 7.26(m, 1H), 7.20(d, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.51(d, 2H), 2.10(br, 1H), 1.90(m, 1H), 1.87(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H), 0.93(d, 6H)

[1092] Example 162. (S)-quinuclidin-3-yl (5-(2,4-dichloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1093] 1H-NMR (400MHz, CDCl3) δ 7.34(d, 2H), 7.26(m, 2H), 7.20(s, 1H),7.02(d, 1H), 4.99(m, 2H), 4.79(br, 1H), 3.94(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1095] Example 163. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1096] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.42(m, 1H), 7.39(s, 1H), 7.25(m, 3H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.61(m, 2H), 2.10(br, 1H), 1.87(br, 1H), 1.67(m, 3H), 1.59(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 6H)

[1098] Example 164. (S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1099] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.42(m, 1H), 7.39(s, 1H), 7.25(m, 3H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.65(m, 2H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(m, 3H), 1.40(m, 3H), 1.30(m, 3H), 0.98(m, 6H)

[1101] Example 165. (S)-quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1102] 1 H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.36(s, 1H), 7.23(m, 1H), 7.10(m, 1H), 6.92(d, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.91(s, 3H), 3.58(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1104] Example 166. (S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1105] 1 H-NMR (400MHz, CDCl3) δ 7.35(m, 1H), 7.33(s, 1H), 7.23(m, 1H), 7.20(d, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.85(s, 3H), 3.80(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1107] Example 167. (S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1108] 1H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.33(s, 1H), 7.26(m, 1H), 6.87(m, 3H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.81(s, 3H), 3.76(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1110] Example 168. (S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1111] 1 H-NMR (400MHz, CDCl3) δ 7.26(m, 2H), 7.19(m, 1H), 7.15(s, 1H), 6.65(d, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.71(s, 6H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1113] Example 169. (S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1114] 1 H-NMR (400MHz, CDCl3) δ 7.43(m, 1H), 7.38(s, 1H), 7.26(m, 1H), 6.71(s, 2H), 6.46(s, 1H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.85(s, 6H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1116] Example 170. (S)-quinuclidin-3-yl (5-(4-ethoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1117] 1 H-NMR (400MHz, CDCl3) δ 7.75(s, 1H), 7.66(d, 1H), 7.34(m, 2H), 7.26(m, 1H), 7.04(d, 1H), 5.00(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 4.16(m, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.45(t, 3H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1119] Example 171. (S)-quinuclidin-3-yl (5-(2,5-difluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1120] 1 H-NMR (400MHz, CDCl3) δ 7.32(m, 3H), 7.16(m, 1H), 6.78(m, 1H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.91(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1122] Example 172. (S)-quinuclidin-3-yl (5-(2-fluoro-5-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1123] 1H-NMR (400MHz, CDCl3) δ 7.37(m, 2H), 7.26(m, 1H), 7.04(t, 1H), 6.91(m, 1H), 6.80(m, 1H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 4.51(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.87(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.33(d, 6H), 1.30(m, 3H), 0.98(m, 3H)

[1125] Example 173. (S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1126] 1 H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.35(s, 1H), 7.25(m, 1H), 7.21(s, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.78(t, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.34(s, 6H), 2.10(br, 1H), 1.85(m, 3H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 1.10(t, 3H), 0.98(m, 3H)

[1128] Example 174. (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1129] 1H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.35(s, 1H), 7.25(m, 1H), 7.22(s, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.91(q, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.34(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.44(t, 3H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1131] Example 175. (S)-quinuclidin-3-yl (5-(2-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1132] 1 H-NMR (400MHz, CDCl3) δ 7.31(d, 2H), 7.25(m, 2H), 7.18(m, 2H), 7.11(s, 1H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 4.12(q, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 1.10(t, 3H), 0.98(m, 3H)

[1134] Example 176. (S)-quinuclidin-3-yl (5-(2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1135] 1 H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.37~7.25(m, 4H), 7.04~6.78(m, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.82(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1137] Example 177. (S)-quinuclidin-3-yl (5-(2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1138] 1 H-NMR (400MHz, CDCl3) δ 7.43(m, 1H), 7.35(s, 1H), 7.32~7.23(m, 3H), 7.03~6.96(m, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 4.05(q, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.37(t, 3H), 1.30(m, 3H), 0.98(m, 3H)

[1140] Example 178. (S)-quinuclidin-3-yl(5-(2-chloro-5-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1141] 1 H-NMR (400MHz, CDCl3) δ 7.48(d, 1H), 7.26(m, 2H), 7.21(d, 2H), 7.14(d, 1H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1143] Example 179. (S)-quinuclidin-3-yl (5-(4-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1144] 1H-NMR (400MHz, CDCl3) δ 7.27(m, 1H), 7.25(m, 3H), 6.70(m, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.80(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1146] Example 180. (S)-quinuclidin-3-yl (5-(4-methoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1147] 1 H-NMR (400MHz, CDCl3) δ 7.26(m, 1H), 7.15(m, 3H), 6.77(m, 2H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 3.84(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.26(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1149] Example 181. (S)-quinuclidin-3-yl (5-(4-( tert -butoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1150] 1 H-NMR (400MHz, CDCl3) δ 7.54(d, 2H), 7.40(m, 4H), 7.26(m, 1H), 4.99(m, 1H), 4.92(br, 1H), 4.79(br, 1H), 4.48(s, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.32(s, 9H), 1.30(m, 3H), 0.99(m, 3H)

[1152] Example 182. (S)-quinuclidin-3-yl (5-(2-chloro-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1153] 1 H-NMR (400MHz, CDCl3) δ 7.72(d, 1H), 7.49(d, 1H), 7.40(m, 1H), 7.32(m, 1H), 7.22(m, 2H), 5.00(m, 2H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1155] Example 183. (S)-quinuclidin-3-yl (5-(2-chloro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1156] 1 H-NMR (400MHz, CDCl3) δ 7.74(s, 1H), 7.57(d, 1H), 7.43(d, 1H), 7.33~7.23(m, 3H), 5.00(m, 2H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1158] Example 184. (S)-quinuclidin-3-yl (5-(2,6-dimethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1159] 1 H-NMR (400MHz, CDCl3) δ 7.56(d, 1H), 7.36(m, 1H), 7.49(m, 1H), 7.32(s, 1H), 6.38(d, 1H), 4.99(m, 1H), 4.86(br, 1H), 4.79(br, 1H), 3.97(s, 6H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1161] Example 185. (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1162] 1 H-NMR (400MHz, CDCl3) δ 8.32(s, 1H), 7.78(d, 1H), 7.33(m, 3H), 6.83(d, 1H), 4.99(m, 1H), 4.86(br, 1H), 4.79(br, 1H), 4.15(d, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H), 0.63(m, 2H), 0.37(m, 2H)

[1164] Example 186. (S)-quinuclidin-3-yl (5-(benzo[b]thiophene-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1165] 1 H-NMR (400MHz, CDCl3) δ 7.67(m, 2H), 7.57(m, 3H), 7.48(m, 2H), 7.30(m, 1H), 4.99(m, 1H), 4.86(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1167] Example 187. (S)-quinuclidin-3-yl (5-(2-( tert -butoxy)pyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1168] 1H-NMR (400MHz, CDCl3) δ 8.16(d, 1H), 7.45(m, 2H), 7.28(m, 1H), 7.03(d, 1H), 6.85(s, 1H), 5.00(m, 1H), 4.86(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.61(s, 9H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1170] Example 188. (S)-quinuclidin-3-yl (5-(6-methoxy-5-(trifluoromethyl)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1171] 1 H-NMR (400MHz, CDCl3) δ 8.50(s, 1H), 8.03(s, 1H), 7.33(m, 3H), 5.00(m, 1H), 4.86(br, 1H), 4.79(br, 1H), 4.09(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.61(s, 9H), 1.40(br, 1H), 1.30(m, 3H), 0.98(m, 3H)

[1173] Example 189. (S)-quinuclidin-3-yl (5-(6-methoxynaphthalene-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1174] 1 H-NMR (400MHz, CDCl3) δ 7.96(s, 1H), 7.81(m, 2H), 7.70(m, 1H), 7.54(m, 2H), 7.32(m, 1H), 7.18(m, 2H), 5.02(m, 1H), 4.86(br, 1H), 4.79(br, 1H), 3.96(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.32(m, 3H), 1.00(m, 3H)

[1176] Example 190. (S)-quinuclidin-3-yl (5-([1,1'-biphenyl]-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1177] 1 H-NMR (400MHz, CDCl3) δ 7.78(s, 1H), 7.66(m, 2H), 7.56(m, 1H), 7.50(m, 5H), 7.39(m, 2H), 7.33(m, 1H), 5.05(m, 1H), 4.92(br, 1H), 4.82(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.32(m, 3H), 1.00(m, 3H)

[1179] Example 191. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoxalin-6-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1180] 1 H-NMR (400MHz, CDCl3) δ 8.85(d, 2H), 8.28(s, 1H), 8.16(m, 1H), 8.04(m, 1H), 7.59(m, 2H), 7.33(m, 1H), 5.02(m, 2H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.32(m, 3H), 1.00(m, 3H)

[1182] Example 192. (S)-quinuclidin-3-yl (5-(3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1183] 1H-NMR (400MHz, CDCl3) δ 7.41(m, 2H), 7.26(m, 1H), 7.19(s, 2H), 6.99(s, 1H), 4.99(m, 1H), 4.81(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.38(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 0.99(m, 3H)

[1185] Example 193. (S)-quinuclidin-3-yl (5-(furan-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1186] 1 H-NMR (400MHz, CDCl3) δ 7.54(m, 1H), 7.49(s, 1H), 7.45(s, 1H), 7.23(m, 1H), 6.63(m, 1H), 6.47(m, 1H), 4.99(m, 1H), 4.81(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.38(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 0.99(m, 3H)

[1188] Example 194. (S)-quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1189] 1 H-NMR (400MHz, CDCl3) δ 7.40(m, 1H), 7.36(s, 1H), 7.25(m, 3H), 4.98(m, 1H), 4.81(br, 1H), 4.79(br, 1H), 4.13(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.33(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.33(d, 6H), 1.31(m, 3H), 0.99(m, 3H)

[1191] Example 195. (S)-quinuclidin-3-yl (5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1192] 1 H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.35(s, 1H), 7.27(m, 3H), 4.99(m, 1H), 4.81(br, 1H), 4.79(br, 1H), 3.76(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.35(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.33(d, 6H), 1.31(m, 3H), 0.99(m, 3H)

[1194] Example 196. (S)-quinuclidin-3-yl (5-(6-isopropoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1195] 1 H-NMR (400MHz, CDCl3) δ 8.34(s, 1H), 7.76(d, 1H), 7.30(m, 3H), 6.74(d, 1H), 5.35(m, 1H), 4.99(m, 1H), 4.81(br, 1H), 4.79(br, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.64(br, 1H), 1.40(br, 1H), 1.38(d, 6H), 1.31(m, 3H), 0.99(m, 3H)

[1197] Example 197. (S)-quinuclidin-3-yl (5-(3-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1198] 1H-NMR (400MHz, CDCl3) δ 7.42(m, 1H), 7.34(m, 1H), 7.27(m, 1H), 7.19(d, 1H), 7.14(s, 1H), 6.91(d, 1H), 5.00(m, 1H), 4.96(m, 3H), 4.79(m, 1H), 4.33(m, 1H), 4.25(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 1.00(m, 3H)

[1200] Example 198. (S)-quinuclidin-3-yl (5-(2-ethoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1201] 1 H-NMR (400MHz, CDCl3) δ 7.41(m, 1H), 7.34(s, 1H), 7.22(m, 1H), 7.09(s, 1H), 7.07(d, 1H), 6.88(d, 1H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.00(m, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.33(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 1.29(m, 3H), 1.00(m, 3H)

[1203] Example 199. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1204] 1H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.35(s, 1H), 7.31(m, 2H), 7.15(m, 1H), 7.11(s, 1H), 6.88(m, 1H), 5.00(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.01(t, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(m, 3H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 1.06(t, 3H), 0.99(m, 3H)

[1206] Example 200. (S)-quinuclidin-3-yl (5-(2-methoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1207] 1 H-NMR (400MHz, CDCl3) δ 7.36(m, 1H), 7.31(s, 1H), 7.27(m, 1H), 7.10(m, 2H), 6.98(d, 1H), 4.98(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.79(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.33(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1209] Example 201. (S)-quinuclidin-3-yl (5-(2-butoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1210] 1H-NMR (400MHz, CDCl3) δ 7.36(m, 1H), 7.34(s, 1H), 7.25(m, 1H), 7.05(m, 1H), 6.95(m, 1H), 6.89(m, 1H), 4.98(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.90(t, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(m, 3H), 1.60(br, 1H), 1.40(m, 3H), 1.30(m, 3H), 0.99(m, 3H), 0.91(t, 3H)

[1212] Example 202. (S)-quinuclidin-3-yl (5-(4-butoxy-3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamey 트

[1213] 1 H-NMR (400MHz, CDCl3) δ 7.59(s, 1H), 7.39(m, 2H), 7.33(s, 1H), 7.26(m, 1H), 6.97(d, 1H), 4.98(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.09(t, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(m, 3H), 1.70(br, 1H), 1.60(m, 3H), 1.40(br, 3H), 1.30(m, 3H), 0.99(m, 3H), 0.97(t, 3H)

[1215] Example 203. (S)-quinuclidin-3-yl (5-(2,4-dipropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1216] 1H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.33(s, 1H), 7.22(m, 2H), 6.55(s, 1H), 6.54(m, 1H), 4.98(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.95(m, 2H), 3.91(m, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(m, 3H), 1.70(m, 3H), 1.60(br, 1H), 1.40(br, 3H), 1.30(m, 3H), 1.05(t, 3H), 0.99(m, 6H)

[1218] Example 204. (S)-quinuclidin-3-yl (5-(3-chloro-4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1219] 1 H-NMR (400MHz, CDCl3) δ 7.60(s, 1H), 7.41(m, 2H), 7.33(s, 1H), 7.26(m, 1H), 6.97(d, 1H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.15(m, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.50(t, 3H), 1.40(br, 3H), 1.30(m, 3H), 0.99(m, 3H)

[1221] Example 205. (S)-quinuclidin-3-yl (5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1222] 1H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.39(s, 1H), 7.31~7.26(m, 2H), 7.14(d, 1H), 7.11(s, 1H), 6.87(d, 1H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.78(d, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(m, 2H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 3H), 1.30(m, 3H), 1.06(d, 6H), 0.99(m, 3H)

[1224] Example 206. (S)-quinuclidin-3-yl (5-(4-ethoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1225] 1 H-NMR (400MHz, CDCl3) δ 7.25(m, 1H), 7.14(m, 3H), 6.81(s, 1H), 6.76(d, 1H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.06(m, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.24(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.43(m, 4H), 1.30(m, 3H), 1.00(m, 3H)

[1227] Example 207. (S)-quinuclidin-3-yl (5-(3-chloro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1228] 1H-NMR (400MHz, CDCl3) δ 7.59(s, 1H), 7.38(m, 3H), 7.25(m, 1H), 6.97(d, 1H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.05(m, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(m, 3H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 1.11(t, 3H), 0.99(m, 3H)

[1230] Example 208. (S)-quinuclidin-3-yl (5-(5-fluoro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1231] 1 H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.34(s, 1H), 7.25(m, 1H), 7.02(d, 1H), 6.92(m, 2H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.24(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 1.20(d, 6H), 0.99(m, 3H)

[1233] Example 209. (S)-quinuclidin-3-yl (5-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1234] 1H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.36(s, 1H), 7.32~7.24(m, 3H), 7.01(t, 1H), 6.92(m, 2H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.57(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.38(d, 6H), 1.30(m, 3H), 0.99(m, 3H)

[1236] Example 210. (S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1237] 1 H-NMR (400MHz, CDCl3) δ 7.36(m, 1H), 7.27(m, 4H), 6.90(d, 1H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.80(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1239] Example 211. (S)-quinuclidin-3-yl (5-(2-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1240] 1 H-NMR (400MHz, CDCl3) δ 7.37(m, 2H), 7.29(m, 1H), 7.20(d, 1H), 7.07(m, 1H), 7.00(m, 1H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.36(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1242] Example 212. (S)-quinuclidin-3-yl (5-(5-chloro-2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1243] 1 H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.31~7.25(m, 3H), 7.21(m, 1H), 6.88(d, 1H), 4.99(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.00(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 6H), 0.99(m, 3H)

[1245] Example 213. (S)-quinuclidin-3-yl (5-(5-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1246] 1 H-NMR (400MHz, CDCl3) δ 7.37(m, 1H), 7.34(s, 1H), 7.25(m, 1H), 7.03(d, 1H), 6.93(m, 1H), 6.88(m, 1H), 5.00(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.88(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(m, 3H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 6H)

[1248] Example 214. (S)-quinuclidin-3-yl (5-(2-fluoro-6-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1249] 1H-NMR (400MHz, CDCl3) δ 7.25(m, 4H), 6.76(m, 2H), 5.00(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.91(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(m, 3H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H), 0.91(t, 3H)

[1251] Example 215. (S)-quinuclidin-3-yl (5-(3-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1252] 1 H-NMR (400MHz, CDCl3) δ 7.40(m, 1H), 7.36(s, 1H), 7.25(m, 4H), 5.00(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.31(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1254] Example 216. (S)-quinuclidin-3-yl (5-(3-fluoro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1255] 1 H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.33(s, 1H), 7.25(m, 3H), 7.01(t, 1H), 5.00(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.05(t, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(m, 3H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 1.07(t, 3H), 0.99(m, 3H)

[1257] Example 217. (S)-quinuclidin-3-yl (5-(5-chloro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1258] 1 H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.31(s, 1H), 7.28(m,1H), 7.20(d, 2H), 6.89(d, 1H), 5.00(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.36(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 1.28(d, 6H), 0.99(m, 3H)

[1260] Example 218. (S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1261] 1 H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.34(s, 1H), 7.32(m, 2H), 7.15(d, 1H), 7.10(s, 1H), 6.87(m, 1H), 5.00(m, 1H), 4.96(m, 1H), 4.79(m, 1H), 4.03(t, 2H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(m, 3H), 1.70(br, 1H), 1.60(m, 3H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1263] Example 219. (S)-quinuclidin-3-yl (5-(3-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1264] 1H-NMR (400MHz, CDCl3) δ 7.41(m, 1H), 7.36(s, 1H), 7.27(m, 1H), 7.16(s, 1H), 7.05(d, 1H), 6.85(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.41(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1266] Example 220. (S)-quinuclidin-3-yl (5-(5-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1267] 1 H-NMR (400MHz, CDCl3) δ 7.27(m, 1H), 7.25(m, 1H), 7.18(m, 1H), 7.13(s, 1H), 6.96(m, 1H), 6.92(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.21(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1269] Example 221. (S)-quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1270] 1 H-NMR (400MHz, CDCl3) δ 7.65(m, 2H), 7.51(m, 1H), 7.26(m, 3H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1272] Example 222. (S)-quinuclidin-3-yl (5-(3-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1273] 1 H-NMR (400MHz, CDCl3) δ 7.41(m, 1H), 7.36(s, 1H), 7.26(m, 1H), 6.89(m, 2H), 6.58(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.86(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1275] Example 223. (S)-quinuclidin-3-yl (5-(2-chloro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1276] 1 H-NMR (400MHz, CDCl3) δ 7.33(d, 1H), 7.26(m, 2H), 7.23(s, 1H), 7.14(s, 1H), 7.07(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.34(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1278] Example 224. (S)-quinuclidin-3-yl (5-(3-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1279] 1H-NMR (400MHz, CDCl3) δ 7.43(m, 3H), 7.28(m, 1H), 7.25(s, 1H), 7.10(s, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.91(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.45(t, 3H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1281] Example 225. (S)-quinuclidin-3-yl (5-(2-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1282] 1 H-NMR (400MHz, CDCl3) δ 7.29(m, 2H), 2.22(m, 3H), 7.02(m, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.31(m, 3H), 0.99(m, 3H)

[1284] Example 226. (S)-quinuclidin-3-yl (5-(4-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1285] 1 H-NMR (400MHz, CDCl3) δ 7.37(m, 2H), 7.28(m, 1H), 7.13(m, 2H), 7.08(m, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.96(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1287] Example 227. (S)-quinuclidin-3-yl (5-(3,4-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1288] 1 H-NMR (400MHz, CDCl3) δ 7.41(m, 1H), 7.38(m, 2H), 7.27(m, 2H), 7.19(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.33(s, 3H), 2.31(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1290] Example 228. (S)-quinuclidin-3-yl (5-(4-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1291] 1 H-NMR (400MHz, CDCl3) δ 7.25(m, 1H), 7.17~7.08(m, 3H), 6.98~6.90(m, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.25(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1293] Example 229. (S)-quinuclidin-3-yl (5-(2-fluoro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1294] 1 H-NMR (400MHz, CDCl3) δ 7.54(m, 1H), 7.46(m, 1H), 7.41~7.36(m, 4H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1296] Example 230. (S)-quinuclidin-3-yl (5-(2-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1297] 1 H-NMR (400MHz, CDCl3) δ 7.39~7.27(m, 3H), 7.04(t, 1H), 6.91(m, 1H), 6.83(m, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.83(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1299] Example 231. (S)-quinuclidin-3-yl (5-(2-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1300] 1 H-NMR (400MHz, CDCl3) δ 7.40~7.27(m, 3H), 7.12(t, 1H), 6.97(m, 2H),4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.93(s, 3H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1302] Example 232. (S)-quinuclidin-3-yl (5-(5-isopropyl-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1303] 1H-NMR (400MHz, CDCl3) δ 7.40(m, 1H), 7.36(s, 1H), 7.27(m, 1H), 7.18(m, 2H), 6.91(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.80(s, 3H), 3.25(m, 1H), 2.91(m, 1H), 2.90~2.75(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 1.26(d, 6H), 0.99(m, 3H)

[1305] Example 233. (S)-quinuclidin-3-yl (5-(2-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1306] 1 H-NMR (400MHz, CDCl3) δ 7.36~7.27(m, 4H), 6.98(m, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.39(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1308] Example 234. (S)-quinuclidin-3-yl (5-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamey 트

[1309] 1 H-NMR (400MHz, CDCl3) δ 7.37(m, 1H), 7.31(s, 1H), 7.27(m, 1H), 7.02(m, 1H), 6.97(m, 1H), 6.91(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.79(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1311] Example 235. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(5-methylfuran-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1312] 1 H-NMR (400MHz, CDCl3) δ 7.47(m, 1H), 7.45(s, 1H), 7.19(m, 1H), 6.51(s, 1H), 6.04(s, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.31(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1314] Example 236. (S)-quinuclidin-3-yl (5-(3-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1315] 1 H-NMR (400MHz, CDCl3) δ 7.36~7.26(m, 3H), 7.07(m, 3H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.73(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 6H)

[1317] Example 237. (S)-quinuclidin-3-yl (5-(2-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1318] 1 H-NMR (400MHz, CDCl3) δ 7.30~7.23(m, 4H), 7.13(m, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 6H)

[1320] Example 238. (S)-quinuclidin-3-yl (5-(benzo[b]thiophene-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1321] 1 H-NMR (400MHz, CDCl3) δ 7.92(m, 2H), 7.46~7.33(m, 6H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1323] Example 239. (S)-quinuclidin-3-yl (5-(4-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1324] 1 H-NMR (400MHz, CDCl3) δ 7.35(m, 1H), 7.30(s, 1H), 7.25(m, 2H), 6.70(m, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.91(t, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(m, 3H), 1.60(br, 1H), 1.40(br, 1H), 1.30(m, 3H), 0.99(m, 6H)

[1326] Example 240. (S)-quinuclidin-3-yl (5-(3-( tert -butyl)-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1327] 1H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.40(s, 2H), 7.26(m, 1H), 7.20(s, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.42(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(m, 3H), 1.60(br, 1H), 1.40(br, 1H), 1.37(s, 9H), 1.30(m, 3H), 0.99(m, 6H)

[1329] Example 241. (S)-quinuclidin-3-yl (5-(2-chloro-5-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1330] 1 H-NMR (400MHz, CDCl3) δ 7.34(d, 1H), 7.28(d, 2H), 7.23(s, 1H), 6.85(s, 1H), 6.81(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 4.00(q, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(m, 3H), 1.60(br, 1H), 1.41(m, 4H), 1.30(m, 3H), 0.99(m, 6H)

[1332] Example 242. (S)-quinuclidin-3-yl (5-(4-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1333] 1 H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.37(m, 3H), 7.28(m, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1335] Example 243. (S)-quinuclidin-3-yl (5-(2-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1336] 1 H-NMR (400MHz, CDCl3) δ 7.38(m, 2H), 7.35~7.23(m, 2H), 7.14(m, 1H), 7.08(t, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.34(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1338] Example 244. (S)-quinuclidin-3-yl (5-(5-cyano-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1339] 1 H-NMR (400MHz, CDCl3) δ 7.64(d, 1H), 7.57(s, 1H), 7.31(m, 3H), 7.02(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.88(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1341] Example 245. (S)-quinuclidin-3-yl(5-(3-ethoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1342] 1 H-NMR (400MHz, CDCl3) δ 7.43(d, 1H), 7.38(s, 2H), 7.30(m, 2H), 7.09(s, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 4.13(m, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(m, 3H), 1.30(m, 3H), 0.99(m, 3H)

[1344] Example 246. (S)-quinuclidin-3-yl (5-(3-fluoro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamey 트

[1345] 1 H-NMR (400MHz, CDCl3) δ 7.61(s, 1H), 7.45(m, 2H), 7.32(s, 1H), 7.30~7.27(m, 2H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1347] Example 247. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-methyl-4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1348] 1 H-NMR (400MHz, CDCl3) δ 7.43(s, 1H), 7.38(m, 3H), 7.26(m, 3H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.38(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1350] Example 248. (S)-quinuclidin-3-yl(2,2-dimethyl-5-(3-(methylthio)-5-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1351] 1 H-NMR (400MHz, CDCl3) δ 7.57(d, 2H), 7.38(m, 3H), 7.29(m, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.57(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1353] Example 249. (S)-quinuclidin-3-yl (5-(3-fluoro-4-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1354] 1 H-NMR (400MHz, CDCl3) δ 7.41~7.27(m, 6H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1356] Example 250. (S)-quinuclidin-3-yl(5-(2-ethoxy-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1357] 1 H-NMR (400MHz, CDCl3) δ 7.40(m, 2H), 7.33(s, 1H), 7.26(m, 2H), 7.17(s, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 4.10(m, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.60(br, 1H), 1.41(m, 4H), 1.30(m, 3H), 0.99(m, 3H)

[1359] Example 251. (S)-quinuclidin-3-yl (5-(2-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1360] 1 H-NMR (400MHz, CDCl3) δ 7.57(d, 1H), 7.54(s, 1H), 7.37(m, 1H), 7.29(s, 2H), 7.02(d, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.86(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1362] Example 252. (S)-quinuclidin-3-yl (5-(2,4-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1363] 1 H-NMR (400MHz, CDCl3) δ 8.00(s, 1H), 7.81(d, 1H), 7.48(d, 1H), 7.26(m, 1H), 7.14(m, 1H), 7.12(s, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1365] Example 253. (S)-quinuclidin-3-yl (5-(3-chloro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1366] 1 H-NMR (400MHz, CDCl3) δ 7.36(d, 1H), 7,26(m, 1H), 7.17~7.08(m, 4H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.25(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1368] Example 254. (S)-quinuclidin-3-yl (5-(3-methoxy-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1369] 1H-NMR (400MHz, CDCl3) δ 7.44(m, 1H), 7.40(s, 1H), 7,26(m, 1H), 7.18(d, 1H), 7.06(d, 1H), 7.02(s, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.90(s, 3H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1371] Example 255. (S)-quinuclidin-3-yl (5-(4-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1372] 1 H-NMR (400MHz, CDCl3) δ 7.38~7.29(m, 4H), 7,26(m, 1H), 7.03(t, 1H), 7.02(s, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.34(s, 3H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1374] Example 256. (S)-quinuclidin-3-yl (5-(2-ethoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1375] 1 H-NMR (400MHz, CDCl3) δ 7.40(m, 1H), 7.33(s, 1H), 7.25(m, 1H), 7.05(m, 1H), 6.95(m, 1H), 6.88(m, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.99(m, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H), 1.30(m, 6H), 0.99(m, 3H)

[1377] Example 257. (S)-quinuclidin-3-yl (5-(3-fluoro-5-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1378] 1 H-NMR (400MHz, CDCl3) δ 7.37(m, 1H), 7.35(s, 1H), 7.27(m, 1H), 7.02(t, 1H), 6.92(m, 1H), 6.81(m, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.93(m, 2H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(m, 3H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 1.05(t, 3H), 0.99(m, 3H)

[1380] Example 258. (S)-quinuclidin-3-yl (5-(3,5-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1381] 1 H-NMR (400MHz, CDCl3) δ 7.99(s, 2H), 7.85(s, 1H), 7.44(m, 2H), 7.32(m, 1H), 4.99(m, 1H), 4.88(m, 1H), 4.80(m, 1H), 3.25(m, 1H), 2.91~2.74(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.41(br, 1H), 1.30(m, 3H), 0.99(m, 3H)

[1383] Example 259. (S)-quinuclidin-3-yl (5-(3-chloro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1384] 1H-NMR (400MHz, CDCl3) δ 7.56(s, 1H), 7.36(m, 3H), 7.28(m, 2H), 4.96(s, 2H), 4.80(br, 1H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.39(s, 3H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1386] Example 260. (S)-quinuclidin-3-yl (5-(2,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1387] 1 H-NMR (400MHz, CDCl3) δ 7.25(m, 1H), 7.16(t, 3H), 7.06(m, 2H), 4.96(s, 2H), 4.80(br, 1H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.34(s, 3H), 2.20(s, 3H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1389] Example 261. (S)-quinuclidin-3-yl (5-(3-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1390] 1 H-NMR (400MHz, CDCl3) δ 7.60(d, 1H), 7.42(m, 1H), 7.35(m, 3H), 7.19(t, 1H), 4.96(s, 2H), 4.80(br, 1H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1392] Example 262. (S)-quinuclidin-3-yl (5-(6-ethoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1393] 1H-NMR (400MHz, CDCl3) δ 8.33(s, 1H), 7.76(d, 1H), 7.69(m, 1H), 7.51(m, 1H), 7.46(m, 1H), 7.36~7.27(m, 1H), 6.77(d, 1H), 4.96(s, 2H), 4.80(br, 1H), 4.37(m, 2H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(br, 1H), 1.39(m, 4H), 1.29(m, 3H), 0.98(m, 3H)

[1395] Example 263. (S)-quinuclidin-3-yl (5-(2-ethoxypyridin-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1396] 1 H-NMR (400MHz, CDCl3) δ 8.17(d, 1H), 7.46(m, 2H), 7.30(m, 1H), 7.06(d, 1H), 6.91(s, 1H), 4.97(m, 2H), 4.80(br, 1H), 4.38(m, 2H), 3.24(m, 1H), 2.89~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(br, 1H), 1.40(m, 4H), 1.30(m, 3H), 0.96(m, 3H)

[1398] Example 264. (S)-quinuclidin-3-yl (5-(2-isopropoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1399] 1 H-NMR (400MHz, CDCl3) δ 8.17(d, 1H), 7.44(m, 2H), 7.31(m, 1H), 7.04(d, 1H), 6.87(s, 1H), 5.34(m, 1H), 4.97(s, 2H), 4.80(br, 1H), 3.24(m, 1H), 2.89~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(br, 1H), 1.40(br, 1H), 1.36(d, 6H), 1.28(m, 3H), 0.97(m, 3H)

[1401] Example 265. (S)-quinuclidin-3-yl (2,2-dimethyl-5-(6-propoxypyridine-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1402] 1 H-NMR (400MHz, CDCl3) δ 8.34(s, 1H), 7.76(d, 1H), 7.34~7.32(m, 3H), 6.79(d, 1H), 4.96(m, 2H), 4.80(br, 1H), 4.28(m, 2H), 3.25(m, 1H), 2.89~2.74(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.81(m, 2H), 1.68(br, 1H), 1.58(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 1.06(t, 3H), 0.98(m, 3H)

[1404] Example 266. (S)-quinuclidin-3-yl (5-(6-butoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1405] 1 H-NMR (400MHz, CDCl3) δ 8.33(s, 1H), 7.76(d, 1H), 7.34~7.31(m, 3H), 6.78(d, 1H), 4.96(s, 2H), 4.80(br, 1H), 4.31(m, 2H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.78(m, 2H), 1.68(br, 1H), 1.58(br, 1H), 1.48(m, 2H), 1.40(br, 1H), 1.29(m, 3H), 1.06(t, 3H), 0.98(m, 6H)

[1407] Example 267. (S)-quinuclidin-3-yl (5-(6-(2-methoxyethoxy)pyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1408] 1H-NMR (400MHz, CDCl3) δ 8.32(s, 1H), 7.76(d, 1H), 7.36~7.28(m, 3H), 6.86(d, 1H), 4.96(m, 2H), 4.80(br, 1H), 4.51(m, 2H), 3.78(m, 2H), 3.45(s, 3H), 3.25(m, 1H), 2.89~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(br, 1H), 1.40(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1410] Example 268. (S)-quinuclidin-3-yl (5-(6-isobutoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1411] 1 H-NMR (400MHz, CDCl3) δ 8.34(s, 1H), 7.76(d, 1H), 7.35~7.27(m, 3H), 6.80(d, 1H), 4.96(m, 2H), 4.78(br, 1H), 4.10(m, 2H), 3.27(m, 1H), 2.89~2.74(m, 7H), 2.08(br, 1H), 1.86(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.42(br, 1H), 1.29(m, 3H), 1.00(d, 6H), 0.98(m, 3H)

[1413] Example 269. (S)-quinuclidin-3-yl (5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1414] 1 H-NMR (400MHz, CDCl3) δ 7.45~7.27(m, 6H), 7.12(d, 1H), 4.97(m, 2H), 4.80(br, 1H), 3.27(m, 1H), 2.89~2.74(m, 7H), 2.53(d, 2H), 2.08(br, 1H), 1.86(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.42(br, 1H), 1.29(m, 3H), 0.98(m, 3H), 0.93(d, 6H)

[1416] Example 270. (S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1417] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.39(m, 2H), 7.28(m, 1H), 6.96(d, 2H), 4.97(m, 2H), 4.80(br, 1H), 4.02(m, 1H), 3.27(m, 1H), 2.89~2.74(m, 7H), 2.53(d, 2H), 2.08(br, 1H), 1.86(br, 1H), 1.77(m, 2H), 1.69(br, 1H), 1.58(br, 1H), 1.52(m, 2H), 1.42(br, 1H), 1.29(m, 3H), 0.98(m, 6H)

[1419] Example 271. (S)-quinuclidin-3-yl (5-(2,4-dimethoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1420] 1 H-NMR(400MHz, CDCl3) δ 7.56(d, 1H), 7.38(m, 1H), 7.30(s, 1H), 7.28(m, 1H), 6.38(d, 1H), 4.97(m, 2H), 4.80(br, 1H), 3.96(s, 6H), 3.27(m, 1H), 2.89~2.74(m, 7H), 2.08(br, 1H), 1.86(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.42(br, 1H), 1.28(m, 3H), 0.97(m, 3H)

[1422] Example 272. (S)-quinuclidin-3-yl (5-(2-acetylthiophene-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1423] 1 H-NMR(400MHz, CDCl3) δ 7.53(d, 1H), 7.30~7.19(m, 3H), 7.03(d, 1H), 5.02(m, 1H), 4.94(m, 1H), 4.79(br, 1H), 3.28(m, 1H), 2.89~2.72(m, 7H), 2.16(s, 3H), 2.08(br, 1H), 1.86(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.42(br, 1H), 1.30(m, 3H), 0.97(m, 3H)

[1425] Example 273. (S)-quinuclidin-3-yl (5-((E)-3-fluorostyryl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1426] 1 H-NMR (400MHz, CDCl3) δ 7.35~7.19(m, 6H), 7.06(d, 2H), 6.97(m, 1H), 4.94(m, 2H), 4.79(br, 1H), 3.28(m, 1H), 2.89~2.71(m, 7H), 2.08(br, 1H), 1.86(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.42(br, 1H), 1.29(m, 3H), 0.96(m, 3H)

[1428] Example 274. (S)-quinuclidin-3-yl (5-((E)-4-ethylstyryl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1429] 1 H-NMR(400MHz, CDCl3) δ 7.44(d, 2H), 7.34(s, 1H), 7.21(m, 4H), 7.07(s, 2H), 4.94(m, 2H), 4.79(br, 1H), 3.28(m, 1H), 2.89~2.71(m, 7H), 2.63(m, 2H), 2.08(br, 1H), 1.86(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.42(br, 1H), 1.27(m, 6H), 0.94(m, 3H)

[1431] Example 275. (S)-quinuclidin-3-yl (5-((E)-2-cyclohexylvinyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1432] 1 H-NMR(400MHz, CDCl3) δ 7.18~7.12(m, 3H), 6.35(m, 1H), 6.16(m, 1H), 4.94(m, 2H), 4.79(br, 1H), 3.28(m, 1H), 2.89~2.71(m, 7H), 2.08(br, 1H), 1.86(br, 1H), 1.76(m, 5H), 1.69(br, 2H), 1.58(br, 1H), 1.42(br, 1H), 1.27(m, 3H), 1.15(m, 3H), 0.94(m, 3H)

[1434] Examples 276 to 311

[1435] The title compounds of Examples 276 to 311 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl (5-bromo-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Reference Example 5 and the corresponding substituted-boronic acid.

[1437] Example 276. (S)-quinuclidin-3-yl(2,2-diethyl-5-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1438] 1 H-NMR (400 MHz, CDCl3) δ 7.52 (m, 2H), 7.50~7.27 (m, 3H), 7.11 (t, 2H), 5.13 (m, 1H), 4.90 (m, 1H), 4.78 (m, 1H), 3.26 (m, 1H), 2.87~2.73(m, 7H), 2.11(br, 1H), 1.88(br, 1H), 1.61(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.95(m, 3H), 0.85(m, 3H)

[1440] Example 277. (S)-quinuclidin-3-yl (2,2-diethyl-5-(4-ethylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1441] 1 H-NMR (400MHz, CDCl3) δ 7.49(d, 2H), 7.40(m, 1H), 7.25(m, 3H), 5.12(m, 1H), 4.93(m, 1H), 4.78(m, 1H), 3.26(m, 1H), 2.87~2.69(m, 7H), 2.67(m, 2H), 2.11(br, 1H), 1.88(br, 1H), 1.61(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 1.26(t, 3H), 0.95(m, 3H), 0.86(m, 3H)

[1443] Example 278. (S)-quinuclidin-3-yl(2,2-diethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1444] 1H-NMR (400MHz, CDCl3) δ 7.48(d, 2H), 7.40(m, 1H), 7.27(m, 1H), 7.25(d, 2H), 5.11(m, 1H), 4.96(m, 1H), 4.78(m, 1H), 3.26(m, 1H), 2.87~2.72(m, 7H), 2.62(m, 2H), 2.11(br, 1H), 1.88(br, 1H), 1.69(m, 3H), 1.58(m, 3H), 1.37(br, 1H), 0.97(m, 6H), 0.85(m, 3H)

[1446] Example 279. (S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1447] 1 H-NMR (400MHz, CDCl3) δ 7.51(d, 2H), 7.45(d, 3H), 7.37(m, 1H), 7.27(m, 1H), 5.12(m, 1H), 4.94(m, 1H), 4.78(m, 1H), 3.26(m, 1H), 2.87~2.71(m, 7H), 2.11(br, 1H), 1.88(br, 1H), 1.69(br, 1H), 1.58(m, 3H), 1.38(br, 1H), 1.36(s, 9H), 0.97(m, 6H), 0.86(m, 3H)

[1449] Example 280. (S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1450] 1 H-NMR (400MHz, CDCl3) δ 7.48(d, 2H), 7.42(m, 2H), 7.30(m, 1H), 7.26(d, 2H), 5.11(m, 1H), 4.94(m, 1H), 4.78(m, 1H), 3.26(m, 1H), 2.87~2.71(m, 7H), 2.63(m, 2H), 2.11(br, 1H), 1.85(br, 1H), 1.69~1.57(m, 6H), 1.38(m, 3H), 0.94(m, 6H), 0.87(m, 3H)

[1452] Example 281. (S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1453] 1 H-NMR (400MHz, CDCl3) δ 7.46(d, 2H), 7.40(m, 1H), 7.30(m, 1H), 7.28(m, 1H), 7.14(d, 2H), 5.12(m, 1H), 4.94(m, 1H), 4.78(m, 1H), 3.26(m, 1H), 2.87~2.71(m, 7H), 2.11(br, 1H), 1.94(m, 1H), 1.85(br, 1H), 1.60(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.95(m, 5H), 0.87(m, 3H), 0.74(m, 2H)

[1455] Example 282. (S)-quinuclidin-3-yl(2,2-diethyl-5-(4-isopropylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1456] 1 H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.41(m, 1H), 7.30(m, 1H), 7.28(m, 3H), 5.11(m, 1H), 4.95(m, 1H), 4.78(m, 1H), 3.26(m, 1H), 2.94(m, 1H), 2.88~2.73(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 1.29(d, 6H), 0.98(m, 3H), 0.87(m, 3H)

[1458] Example 283. (S)-quinuclidin-3-yl(2,2-diethyl-5-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1459] 1H-NMR (400MHz, CDCl3) δ 7.50(d, 2H), 7.38(m, 1H), 7.30(m, 2H), 6.96(d, 2H), 5.12(m, 1H), 4.91(m, 1H), 4.88(m, 1H), 3.85(s, 3H), 3.26(m, 1H), 2.88~2.71(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.97(m, 3H), 0.87(m, 3H)

[1461] Example 284. (S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1462] 1 H-NMR (400MHz, CDCl3) δ 7.49(d, 2H), 7.35(m, 1H), 7.28(m, 2H), 6.95(d, 2H), 5.12(m, 1H), 4.91(m, 1H), 4.88(m, 1H), 4.10(m, 2H), 3.26(m, 1H), 2.88~2.71(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.41(t, 3H), 1.37(br, 1H), 0.97(m, 3H), 0.87(m, 3H)

[1464] Example 285. (S)-quinuclidene-3-yl(2,2-diethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1465] 1 H-NMR (400MHz, CDCl3) δ 7.49(d, 2H), 7.35(m, 1H), 7.28(m, 2H), 6.96(d, 2H), 5.12(m, 1H), 4.91(m, 1H), 4.88(m, 1H), 3.98(t, 2H), 3.26(m, 1H), 2.88~2.71(m, 7H), 2.11(br, 1H), 1.85(m, 3H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 1.06(t, 3H), 0.97(m, 3H), 0.87(m, 3H)

[1467] Example 286. (S)-quinuclidene-3-yl(2,2-diethyl-5-(4-isopropoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1468] 1 H-NMR (400MHz, CDCl3) δ 7.49(d, 2H), 7.35(m, 1H), 7.28(m, 2H), 6.96(d, 2H), 5.12(m, 1H), 4.91(m, 1H), 4.78(m, 1H), 4.77(m, 1H), 3.26(m, 1H), 2.88~2.71(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 1.36(d, 6H), 0.96(m, 3H), 0.87(m, 3H)

[1470] Example 287. (S)-quinuclidin-3-yl(2,2-diethyl-5-(4-isobutylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1471] 1 H-NMR (400MHz, CDCl3) δ 7.48(d, 2H), 7.38(m, 1H), 7.28(m, 2H), 7.20(d, 2H), 5.13(m, 1H), 4.92(m, 1H), 4.78(m, 1H), 3.26(m, 1H), 2.88~2.73(m, 7H), 2.51(d, 2H), 2.11(br, 1H), 1.92(m, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.93(d, 6H), 0.86(m, 3H)

[1473] Example 288. (S)-quinuclidin-3-yl(2,2-diethyl-5-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1474] 1 H-NMR (400MHz, CDCl3) δ 7.41~7.02(m, 6H), 7.02(t, 1H), 5.14(m, 1H), 4.92(m, 1H), 4.79(m, 1H), 3.24(m, 1H), 2.88~2.74(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.86(m, 3H)

[1476] Example 289. (S)-quinuclidene-3-yl(2,2-diethyl-5-(3-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1477] 1 H-NMR (400MHz, CDCl3) δ 7.43(m, 1H), 7.37~7.27(m, 3H), 7.17(d, 1H), 7.15(s, 1H), 6.88(d, 1H), 5.13(m, 1H), 4.91(m, 1H), 4.79(m, 1H), 3.87(s, 3H), 3.25(m, 1H), 2.88~2.74(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.86(m, 3H)

[1479] Example 290. (S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1480] 1 H-NMR (400MHz, CDCl3) δ 7.41(m, 1H), 7.38~7.27(m, 3H), 7.15(d, 1H), 7.13(s, 1H), 6.89(d, 1H), 5.13(m, 1H), 4.91(m, 1H), 4.79(m, 1H), 4.12(m, 2H), 3.25(m, 1H), 2.88~2.74(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.43(t, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.87(m, 3H)

[1482] Example 291. (S)-quinuclidene-3-yl(2,2-diethyl-5-(3-isopropoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1483] 1H-NMR (400MHz, CDCl3) δ 7.41(m, 1H), 7.39~7.27(m, 3H), 7.12(d, 1H), 7.09(s, 1H), 6.88(d, 1H), 5.13(m, 1H), 4.91(m, 1H), 4.78(m, 1H), 4.62(m, 1H), 3.25(m, 1H), 2.88~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.29(br, 1H), 1.26(d, 6H), 0.97(m, 3H), 0.86(m, 3H)

[1485] Example 292. (S)-quinuclidin-3-yl (2,2-diethyl-5-(3-ethylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1486] 1 H-NMR (400MHz, CDCl3) δ 7.44~7.27(m, 6H), 7.18(d, 1H), 5.13(m, 1H), 4.93(m, 1H), 4.78(m, 1H), 3.27(m, 1H), 2.85~2.71(m, 7H), 2.68(m, 2H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.39(br, 1H), 1.29(t, 3H), 0.97(m, 3H), 0.86(m, 3H)

[1488] Example 293. (S)-quinuclidin-3-yl(2,2-diethyl-5-(3-isopropylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1489] 1 H-NMR (400MHz, CDCl3) δ 7.44~7.27(m, 6H), 7.21(d, 1H), 5.14(m, 1H), 4.92(m, 1H), 4.79(m, 1H), 3.27(m, 1H), 2.99(m, 1H), 2.85~2.71(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.39(br, 1H), 1.27(d, 6H), 0.98(m, 3H), 0.86(m, 3H)

[1491] Example 294. (S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1492] 1 H-NMR (400MHz, CDCl3) δ 7.58(s, 1H), 7.41~7.27(m, 6H), 5.11(m, 1H), 4.92(m, 1H), 4.79(m, 1H), 3.27(m, 1H), 2.86~2.75(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.39(br, 1H), 1.38(s, 9H), 0.96(m, 3H), 0.87(m, 3H)

[1494] Example 295. (S)-quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1495] 1 H-NMR (400MHz, CDCl3) δ 7.37~7.26(m, 3H), 7.10(m, 1H), 6.92(d, 2H), 5.14(m, 1H), 4.92(m, 1H), 4.77(m, 1H), 3.91(s, 3H), 3.59(s, 3H), 3.25(m, 1H), 2.86~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.85(m, 3H)

[1497] Example 296. (S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1498] 1 H-NMR (400MHz, CDCl3) δ 7.33(m, 1H), 7.28~7.21(m, 3H), 6.57(m, 2H), 5.11(m, 1H), 4.90(m, 1H), 4.85(m, 1H), 3.85(s, 3H), 3.80(s, 3H), 3.24(m, 1H), 2.86~2.71(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.95(m, 3H), 0.87(m, 3H)

[1500] Example 297 . (S)-quinuclidene-3-yl (5-(2,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1501] 1 H-NMR (400MHz, CDCl3) δ 7.35(m, 1H), 7.30~7.27(m, 2H), 6.92~6.83(m, 3H), 5.12(m, 1H), 4.90(m, 1H), 4.85(m, 1H), 3.80(s, 3H), 3.75(s, 3H), 3.24(m, 1H), 2.86~2.72(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.87(m, 3H)

[1503] Example 298. (S)-quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1504] 1 H-NMR (400MHz, CDCl3) δ 7.39(m, 1H), 7.31(s, 1H), 7.28(m, 1H), 7.13(d, 1H), 7.08(s, 1H), 6.93(d, 1H), 5.12(m, 1H), 4.91(m, 1H), 4.85(m, 1H), 3.95(s, 3H), 3.92(s, 3H), 3.24(m, 1H), 2.86~2.72(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.95(m, 3H), 0.86(m, 3H)

[1506] Example 299. (S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1507] 1H-NMR (400MHz, CDCl3) δ 7.40(m, 1H), 7.39(s, 1H), 7.29(m, 1H), 6.70(s, 2H), 6.45(m, 1H), 5.13(m, 1H), 4.92(m, 1H), 4.85(brs, 1H), 3.85(s, 6H), 3.24(m, 1H), 2.86~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.87(m, 3H)

[1509] Example 300. (S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1510] 1 H-NMR (400MHz, CDCl3) δ 7.30~7.26(m, 2H), 7.18(d, 1H), 7.14(s, 1H), 6.65(d, 2H), 5.12(m, 1H), 4.92(m, 1H), 4.77(m, 1H), 3.73(s, 6H), 3.24(m, 1H), 2.85~2.71(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.88(m, 3H)

[1512] Example 301. (S)-quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1513] 1 H-NMR (400MHz, CDCl3) δ 7.70(m, 2H), 7.53~7.39(m, 4H), 7.31(m, 1H), 6.85~6.56(t, 1H), 5.15(m, 1H), 4.92(m, 1H), 4.79(m, 1H), 3.24(m, 1H), 2.85~2.74(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.86(m, 3H)

[1515] Example 302. (S)-quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1516] 1 H-NMR (400MHz, CDCl3) δ 7.43(m, 1H), 7.38(s, 1H), 7.27(m, 2H), 6.91(m, 2H), 6.73(d, 1H), 5.13(m, 1H), 4.88(m, 1H), 4.79(m, 1H), 3.24(m, 1H), 3.00(s, 6H), 2.85~2.74(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.87(m, 3H)

[1518] Example 303. (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1519] 1 H-NMR (400MHz, CDCl3) δ 7.38~7.33(m, 2H), 7.28(m, 1H), 7.21(s, 2H), 5.12(m, 1H), 4.88(m, 1H), 4.79(m, 1H), 3.89(q, 2H), 3.25(m, 1H), 2.85~2.74(m, 7H), 2.33(s, 6H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.41(t, 3H), 1.37(br, 1H), 0.95(m, 3H), 0.85(m, 3H)

[1521] Example 304. (S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1522] 1H-NMR(400MHz, CDCl3) δ 7.38~7.30(m, 2H), 7.28(m, 1H), 7.20(s, 2H), 5.11(m, 1H), 4.93(m, 1H), 4.79(m, 1H), 3.77(t, 2H), 3.25(m, 1H), 2.85~2.74(m, 7H), 2.33(s, 6H), 2.05(br, 1H), 1.85(m, 3H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 1.09(t, 3H), 0.95(m, 3H), 0.85(m, 3H)

[1524] Example 305. (S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1525] 1 H-NMR (400MHz, CDCl3) δ 7.38~7.30(m, 2H), 7.28(m, 1H), 7.20(s, 2H), 5.12(m, 1H), 4.91(m, 1H), 4.79(m, 1H), 3.78(t, 2H), 3.25(m, 1H), 2.85~2.74(m, 7H), 2.33(s, 6H), 2.05(br, 1H), 1.85(m, 3H), 1.68(br, 1H), 1.58(m, 5H), 1.37(br, 1H), 0.99(t, 3H), 0.95(m, 3H), 0.86(m, 3H)

[1527] Example 306. (S)-quinuclidin-3-yl (2,2-diethyl-5-(thiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1528] 1 H-NMR (400MHz, CDCl3) δ 7.45~7.36(m, 5H), 7.26(m, 1H), 5.11(m, 1H), 4.88(m, 1H), 4.77(m, 1H), 3.25(m, 1H), 2.85~2.72(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.95(m, 3H), 0.85(m, 3H)

[1530] Example 307. (S)-quinuclidin-3-yl (2,2-diethyl-5-(furan-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1531] 1 H-NMR (400MHz, CDCl3) δ 7.70(s, 1H), 7.46(s, 1H), 7.30~7.20(m, 3H), 6.68(s, 1H), 5.10(m, 1H), 4.88(m, 1H), 4.78(m, 1H), 3.25(m, 1H), 2.85~2.69(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.94(m, 3H), 0.85(m, 3H)

[1533] Example 308. (S)-quinuclidean-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1534] 1 H-NMR (400MHz, CDCl3) δ 8.31(s, 1H), 7.77(d, 1H), 7.31(m, 3H), 6.82(d, 1H), 5.12(m, 1H), 4.93(m, 1H), 4.78(m, 1H), 4.16(m, 2H), 3.25(m, 1H), 2.85~2.72(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.94(m, 3H), 0.85(m, 3H), 0.63(m, 2H), 0.37(m, 2H)

[1536] Example 309. (S)-quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1537] 1 H-NMR (400MHz, CDCl3) δ 7.33~7.24(m, 5H), 7.10(m, 1H), 5.14(m, 1H), 4.91(m, 1H), 4.87(m, 1H), 3.25(m, 1H), 2.85~2.73(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.86(m, 3H)

[1539] Example 310. (S)-quinuclidin-3-yl(2,2-diethyl-5-(2-fluoro-4-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1540] 1 H-NMR (400MHz, CDCl3) δ 7.34~7.27(m, 4H), 6.74(m, 2H), 5.12(m, 1H), 4.94(m, 1H), 4.77(m, 1H), 3.83(s, 3H), 3.25(m, 1H), 2.85~2.72(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.86(m, 3H)

[1542] Example 311. (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1543] 1 H-NMR (400MHz, CDCl3) δ 7.59(s, 1H), 7.40~7.01(m, 4H), 7.00(d, 1H), 5.13(m, 1H), 4.94(m, 1H), 4.77(m, 1H), 3.83(s, 3H), 3.25(m, 1H), 2.85~2.72(m, 7H), 2.05(br, 1H), 1.85(br, 1H), 1.68(br, 1H), 1.58(m, 3H), 1.37(br, 1H), 0.96(m, 3H), 0.86(m, 3H)

[1545] Examples 312 to 348

[1546] The title compounds of Examples 312 to 348 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl (5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Reference Example 6 and the corresponding substituted-boronic acid.

[1548] Example 312. (S)-quinuclidin-3-yl (5-(4-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1549] 1H-NMR (400MHz, CDCl3) δ 7.42(d, 2H), 7.24(m, 3H), 6.85(d, 1H), 4.94(m, 1H), 4.82(m, 1H), 4.74(br, 1H), 3.79(d, 3H), 3.29(m, 1H), 2.91(m, 2H), 2.89~2.70(m, 5H),2.69(m, 2H), 2.11(br, 1H), 1.88(br, 1H), 1.72(br, 1H), 1.61(br, 1H), 1.44(br, 1H), 1.30(m, 6H), 1.00(m, 3H)

[1551] Example 313. (S)-quinuclidin-3-yl(6-methoxy-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1552] 1 H-NMR (400MHz, CDCl3) δ 7.41(d, 2H), 7.22(d, 2H), 7.11(s, 1H), 6.85(d, 1H), 4.95(m, 1H), 4.82(m, 1H), 4.74(br, 1H), 3.79(d, 3H), 3.29(m, 1H), 2.90(m, 2H), 2.89~2.71(m, 5H), 2.62(m, 2H), 2.11(br, 1H), 1.88(br, 1H), 1.72~1.67(m, 3H), 1.61(br, 1H), 1.43(br, 1H), 1.32(m, 3H), 1.00(m, 6H)

[1554] Example 314. (S)-quinuclidin-3-yl (5-(4-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1555] 1 H-NMR (400MHz, CDCl3) δ 7.43(d, 2H), 7.26(d, 2H), 7.11(s, 1H), 6.85(d, 1H), 4.95(m, 1H), 4.82(m, 1H), 4.74(br, 1H), 3.80(d, 3H), 3.29(m, 1H), 2.92(m, 3H), 2.89~2.71(m, 5H), 2.11(br, 1H), 1.88(br, 1H), 1.71(br, 1H), 1.62(br, 1H), 1.44(br, 1H), 1.30(m, 9H), 1.00(m, 3H)

[1557] Example 315. (S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1558] 1 H-NMR (400MHz, CDCl3) δ 7.41(d, 2H), 7.17(d, 2H), 7.11(s, 1H),6.85(d, 1H), 4.95(m, 1H), 4.82(m, 1H), 4.74(br, 1H), 3.80(d, 3H), 3.29(m, 1H), 2.90~2.71(m, 7H), 2.50(d, 2H), 2.11(br, 1H), 1.92(m, 2H), 1.71(br, 1H), 1.62(br, 1H), 1.44(br, 1H), 1.30(m, 3H), 1.00(m, 3H), 0.99(d, 6H)

[1560] Example 316. (S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1561] 1 H-NMR (400MHz, CDCl3) δ 7.46(m, 4H), 7.12(s, 1H), 6.85(d, 1H), 4.95(m, 1H), 4.82(m, 1H), 4.74(br, 1H), 3.81(d, 3H), 3.29(m, 1H), 2.93~2.66(m, 7H), 2.50(d, 2H), 2.11(br, 1H), 1.88(br, 1H), 1.71(br, 1H), 1.62(br, 1H),1.44(br, 1H), 1.40(s, 9H), 1.30(m, 3H), 1.00(m, 3H)

[1563] Example 317. (S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1564] 1H-NMR (400MHz, CDCl3) δ 7.39(d, 2H), 7.10(d, 3H), 6.85(d, 1H), 4.95(m, 1H), 4.82(m, 1H), 4.74(br, 1H), 3.81(d, 3H), 3.29(m, 1H), 2.93~2.66(m, 7H), 2.50(d, 2H), 2.11(br, 1H), 1.90(m, 1H), 1.88(br, 1H), 1.71(br, 1H), 1.62(br, 1H), 1.44(br, 1H), 1.30(m, 3H), 1.00(m, 3H), 0.98(d, 2H), 0.75(m, 2H)

[1566] Example 318. (S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1567] 1 H-NMR (400MHz, CDCl3) δ 7.42(d, 2H), 7.09(s, 1H), 6.93(d, 2H), 6.81(d, 1H), 4.94(m, 2H), 4.81(m, 1H), 4.09(m, 2H), 3.80(d, 3H), 3.28(m, 1H), 2.90~2.671(m, 7H), 2.11(br, 1H), 1.90(m, 1H), 1.88(br, 1H), 1.71(br, 1H), 1.62(br, 1H), 1.43(t, 4H), 1.26(m, 3H), 0.97(m, 3H)

[1569] Example 319. (S)-quinuclidin-3-yl(6-methoxy-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1570] 1H-NMR (400MHz, CDCl3) δ 7.42(d, 2H), 7.09(s, 1H), 6.94(d, 2H), 6.82(d, 1H), 4.94(m, 2H), 4.81(m, 1H), 3.95(m, 2H), 3.80(d, 3H), 3.28(m, 1H), 2.90~2.67(m, 7H), 2.11(br, 1H), 1.90(m, 1H), 1.88(br, 1H), 1.83(m, 2H), 1.71(br, 1H), 1.62(br, 1H), 1.43(br, 1H), 1.26(m, 3H), 1.07(t, 3H), 0.97(m, 3H)

[1572] Example 320. (S)-quinuclidin-3-yl (5-(4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1573] 1 H-NMR (400MHz, CDCl3) δ 7.42(d, 2H), 7.09(s, 1H), 6.90(d, 2H), 6.85(d, 1H), 4.93(m, 2H), 4.81(m, 1H), 4.59(m, 1H), 3.80(d, 3H), 3.28(m, 1H), 2.90~2.72(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.37(d, 6H), 1.28(m, 3H), 0.97(m, 3H)

[1575] Example 321. (S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1576] 1H-NMR (400MHz, CDCl3) δ 7.13(s, 2H), 7.07(s, 1H), 6.82(d, 1H), 4.93(m, 2H), 4.81(m, 1H), 3.78(m, 5H), 3.27(m, 1H), 2.90~2.69(m, 7H), 2.31(s, 6H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.69(m, 2H), 1.60(br, 1H), 1.43(br, 1H), 1.28(m, 3H), 1.09(t, 3H), 0.93(m, 3H)

[1578] Example 322. (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1579] 1 H-NMR (400MHz, CDCl3) δ 7.52(s, 1H), 7.33(d, 1H), 7.07(s, 1H), 6.96(d, 1H), 6.83(d, 1H), 4.93(m, 2H), 4.81(m, 1H), 4.58(m, 1H), 3.78(m, 3H), 3.27(m, 1H), 2.90~2.70(m, 7H), 2.10(br, 1H), 1.86(br, 1H), 1.71(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.40(d, 6H), 1.28(m, 3H), 0.96(m, 3H)

[1581] Example 323. (S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1582] 1 H-NMR (400MHz, CDCl3) δ 7.24(m, 1H), 7.03(s, 1H), 6.87(d, 1H), 6.75~6.67(m, 2H), 4.96(m, 2H), 4.81(m, 1H), 3.80(s, 3H), 3.78(m, 3H), 3.27(m, 1H), 2.90~2.70(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.58(br, 1H), 1.41(br, 1H), 1.28(m, 3H), 0.97(m, 3H)

[1584] Example 324. (S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1585] 1 H-NMR (400MHz, CDCl3) δ 7.42(d, 2H), 7.09(s, 1H), 6.93(d, 2H), 6.83(d, 1H), 4.93(m, 2H), 4.81(m, 1H), 3.98(m, 2H), 3.79(m, 3H), 3.27(m, 1H), 2.90~2.71(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.71(m, 2H), 1.69(br, 1H), 1.59(br, 1H), 1.52(m, 2H), 1.43(br, 1H), 1.27(m, 3H), 0.99(m, 6H)

[1587] Example 325. (S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1588] 1 H-NMR (400MHz, CDCl3) δ 7.42(d, 2H), 7.09(s, 1H), 6.93(d, 2H), 6.83(d, 1H), 4.93(m, 2H), 4.81(m, 1H), 3.79(m, 5H), 3.27(m, 1H), 2.90~2.71(m, 7H), 2.10(m, 2H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.43(br, 1H), 1.27(m, 3H), 0.99(m, 6H)

[1590] Example 326. (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1591] 1H-NMR (400MHz, CDCl3) δ 8.24(s, 1H), 7.74(d, 1H), 7.07(s, 1H), 6.86(d, 1H), 6.80(d, 1H), 4.93(m, 2H), 4.81(m, 1H), 4.15(m, 2H), 3.79(m, 3H), 3.27(m, 1H), 2.90~2.71(m, 7H), 2.10(m, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.43(br, 1H), 1.27(m, 3H), 0.97(m, 3H), 0.62(m, 2H), 0.38(m, 2H)

[1593] Example 327. (S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1594] 1 H-NMR (400MHz, CDCl3) δ 7.25(s, 1H) 7.19(m, 1H), 7.00(s, 1H), 6.89~6.82(m, 2H), 4.93(m, 2H), 4.81(m, 1H), 3.79(m, 6H), 3.29(m, 1H), 2.92~2.65(m, 7H), 2.10(m, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.43(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1596] Example 328. (S)-quinuclidin-3-yl (5-(4-butylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1597] 1 H-NMR (400MHz, CDCl3) δ 7.40(d, 2H) 7.20(d, 2H), 7.10(s, 1H), 6.84(d, 1H), 4.95(s, 2H), 4.80(br, 1H), 3.78(d, 3H), 3.25(m, 1H), 2.92~2.65(m, 7H), 2.64(m, 2H), 2.10(m, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.60(m, 2H), 1.59(br, 1H), 1.43(m, 3H), 1.29(m, 3H), 0.98(m, 3H), 0.92(t, 3H)

[1599] Example 329. (S)-quinuclidin-3-yl(6-methoxy-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1600] 1 H-NMR (400MHz, CDCl3) δ 7.14(s, 2H) 7.07(s, 1H), 6.82(d, 1H), 4.94(s, 2H), 4.80(br, 1H), 3.78(d, 3H), 3.76(s, 3H), 3.25(m, 1H), 2.92~2.65(m, 7H), 2.32(s, 6H), 2.10(m, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.40(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1602] Example 330. (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1603] 1 H-NMR (400MHz, CDCl3) δ 7.14(s, 2H) 7.07(s, 1H), 6.83(d, 1H), 4.94(s, 2H), 4.80(br, 1H), 3.89(m, 2H), 3.78(d, 3H), 3.25(m, 1H), 2.92~2.65(m, 7H), 2.31(s, 6H), 2.10(m, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.43(t, 4H), 1.28(m, 3H), 0.98(m, 3H)

[1605] Example 331. (S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1606] 1H-NMR (400MHz, CDCl3) δ 7.13(s, 2H), 7.07(s, 1H), 6.83(d, 1H), 4.93(m, 2H), 4.80(br, 1H), 3.80(m, 3H), 3.25(m, 1H), 2.92~2.71(m, 7H), 2.69(m, 2H), 2.31(s, 6H), 2.10(m, 1H), 1.85(br, 1H), 1.77(m, 2H), 1.69(br, 1H), 1.60(m, 2H), 1.59(m, 3H), 1.43(br, 1H), 1.29(m, 3H), 0.98(m, 6H)

[1608] Example 332. (S)-quinuclidin-3-yl(6-methoxy-5-(2-methoxypyridin-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1609] 1 H-NMR (400MHz, CDCl3) δ 8.15(d, 1H), 7.11(s, 1H), 7.03(d, 1H), 6.89(s, 1H), 6.85(d, 1H), 4.93(m, 2H), 4.80(br, 1H), 3.97(s, 3H), 3.79(d, 3H), 3.25(m, 1H), 2.92~2.71(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.43(br, 1H), 1.29(m, 3H), 0.98(m, 6H)

[1611] Example 333 . (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1612] 1 H-NMR (400MHz, CDCl3) δ 7.34(m, 1H), 7.25(m, 2H), 7.10(s, 1H), 7.02(m, 1H), 6.86(m, 1H), 4.95(s, 2H), 4.80(br, 1H), 3.81(m, 3H), 3.25(m, 1H), 2.90~2.71(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1614] Example 334. (S)-quinuclidin-3-yl (5-(3-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1615] 1 H-NMR (400MHz, CDCl3) δ 7.33(s, 3H), 7.17(m, 1H), 7.16(s, 1H), 6.86(m, 1H), 4.95(m, 2H), 4.80(br, 1H), 3.80(m, 3H), 3.25(m, 1H), 2.90~2.80(m, 7H), 2.70(m, 2H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 6H), 0.98(m, 3H)

[1617] Example 335. (S)-quinuclidin-3-yl (5-(3-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1618] 1 H-NMR (400MHz, CDCl3) δ 7.32~7.27(m, 3H), 7.11(m, 2H), 6.85(m, 1H), 4.95(m, 2H), 4.80(br, 1H), 3.79(m, 3H), 3.25(m, 1H), 2.90~2.72(m, 7H), 2.53(d, 2H), 2.10(br, 1H), 1.90(m, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H), 0.90(d, 6H)

[1620] Example 336. (S)-quinuclidin-3-yl (5-(3-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1621] 1H-NMR (400MHz, CDCl3) δ 7.33(m, 3H), 7.20(m, 1H), 7.12(s, 1H), 6.85(m, 1H), 4.95(m, 2H), 4.80(br, 1H), 3.80(m, 3H), 3.25(m, 1H), 2.95(m, 1H), 2.90~2.72(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 9H), 0.98(m, 3H)

[1623] Example 337. (S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1624] 1 H-NMR (400MHz, CDCl3) δ 7.52(s, 1H), 7.33(m, 3H), 7.12(s, 1H), 6.86(m, 1H), 4.95(m, 2H), 4.80(br, 1H), 3.80(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.37(s, 9H), 1.28(m, 3H), 0.98(m, 3H)

[1626] Example 338. (S)-quinuclidin-3-yl(6-methoxy-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1627] 1 H-NMR (400MHz, CDCl3) δ 7.31(m, 1H), 7.11~7.06(m, 3H), 6.87(m, 2H), 4.95(m, 2H), 4.80(br, 1H), 3.84(s, 3H), 3.80(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1629] Example 339. (S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1630] 1 H-NMR (400MHz, CDCl3) δ 7.30(m, 1H), 7.11(s, 1H), 7.07(m, 2H), 6.85(m, 2H), 4.95(m, 2H), 4.80(br, 1H), 4.08(m, 2H), 3.79(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.43(t, 3H), 1.28(m, 3H), 0.98(m, 3H)

[1632] Example 340. (S)-quinuclidin-3-yl(6-methoxy-2,2-methyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1633] 1 H-NMR (400MHz, CDCl3) δ 7.28(m, 1H), 7.11(s, 1H), 7.06(m, 2H), 6.86(m, 2H), 4.95(m, 2H), 4.80(br, 1H), 3.96(m, 2H), 3.79(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.80(m, 2H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 6H)

[1635] Example 341. (S)-quinuclidin-3-yl (5-(3-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1636] 1H-NMR (400MHz, CDCl3) δ 7.28(m, 1H), 7.11(s, 1H), 7.05(m, 2H), 6.85(d, 2H), 4.95(m, 2H), 4.80(br, 1H), 4.59(m, 1H), 3.80(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.35(d, 6H), 1.28(m, 3H), 0.98(m, 3H)

[1638] Example 342. (S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1639] 1 H-NMR (400MHz, CDCl3) δ 7.28(m, 1H), 7.10(s, 1H), 7.05(m, 2H), 6.86(d, 2H), 4.95(m, 2H), 4.80(br, 1H), 3.98(m, 2H), 3.80(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.78(m, 2H), 1.70(br, 1H), 1.59(br, 1H), 1.55(m, 2H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 6H)

[1641] Example 343. (S)-quinuclidin-3-yl (5-(3-isobutoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1642] 1 H-NMR (400MHz, CDCl3) δ 7.28(m, 1H), 7.11(s, 1H), 7.05(m, 2H), 6.85(d, 2H), 4.95(m, 2H), 4.80(br, 1H), 3.80(m, 3H), 3.75(d, 2H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(m, 2H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 9H)

[1644] Example 344. (S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1645] 1 H-NMR (400MHz, CDCl3) δ 7.03(s, 1H), 7.03~6.80(m, 4H), 4.95(s, 2H), 4.80(br, 1H), 3.78(m, 6H), 3.73(s, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1647] Example 345. (S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1648] 1 H-NMR (400MHz, CDCl3) δ 7.11(s, 1H), 6.85(m, 1H), 6.65(s, 2H), 6.45(s, 1H), 4.95(s, 2H), 4.80(br, 1H), 3.80(m, 9H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1650] Example 346 . (S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1651] 1 H-NMR (400MHz, CDCl3) δ 7.17(d, 1H), 7.00(s, 1H), 6.96(s, 1H), 6.84(m, 2H), 4.95(s, 2H), 4.80(br, 1H), 3.82(s, 3H), 3.75(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1653] Example 347 . (S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1654] 1 H-NMR (400MHz, CDCl3) δ 7.30(m 1H), 7.18(d, 1H), 7.08(s, 1H), 6.98(t, 1H), 6.84(d, 1H), 4.95(s, 2H), 4.80(br, 1H), 4.14(m, 2H), 3.79(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.47(t, 3H), 1.45(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1656] Example 348 . (S)-quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1657] 1 H-NMR (400MHz, CDCl3) δ 7.13(s, 2H), 7.08(s, 1H), 6.82(d, 1H), 4.95(s, 2H), 4.80(br, 1H), 4.22(m, 1H), 3.78(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.30(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.45(br, 1H), 1.30(d, 6H), 1.28(m, 3H), 0.98(m, 3H)

[1659] Examples 349 to 388

[1660] The title compounds of Examples 349 to 388 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl (5-bromo-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Reference Example 7 and the corresponding substituted-boronic acid.

[1662] Example 349. (S)-quinuclidin-3-yl (5-(4-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1663] 1 H-NMR (400MHz, CDCl3) δ 7.44(d, 2H), 7.27(d, 2H), 7.20(d, 1H), 7.03~6.97(m, 1H), 4.93(m, 2H), 4.79(br, 1H), 3.28(m, 1H), 2.90~2.71(m, 7H), 2.69(m, 2H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.59(br, 1H), 1.43(br, 1H), 1.32(m, 6H), 0.97(m, 3H)

[1665] Example 350. (S)-quinuclidin-3-yl(6-fluoro-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1666] 1 H-NMR (400MHz, CDCl3) δ 7.44(d, 2H), 7.27(m, 2H), 7.00(m, 1H), 7.03~6.97(m, 1H), 4.92(m, 2H), 4.79(br, 1H), 3.28(m, 1H), 2.90~2.71(m, 7H), 2.63(m, 2H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.68(m, 2H), 1.60(br, 1H), 1.43(br, 1H), 1.32(m, 6H), 0.97(m, 3H)

[1668] Example 351. (S)-quinuclidin-3-yl(6-fluoro-5-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1669] 1 H-NMR (400MHz, CDCl3) δ 7.44(d, 2H), 7.27(m, 2H), 7.00(m, 1H), 7.03~6.97(m, 1H), 4.92(m, 2H), 4.79(br, 1H), 3.28(m, 1H), 2.96(m, 1H), 2.90~2.72(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.28(m, 9H), 0.97(m, 3H)

[1671] Example 352. (S)-quinuclidin-3-yl(6-fluoro-5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1672] 1 H-NMR (400MHz, CDCl3) δ 7.44(d, 2H), 7.22(d, 3H), 7.03~6.97(m, 1H), 4.92(m, 2H), 4.79(br, 1H), 3.28(m, 1H), 2.90~2.72(m, 7H), 2.52(d, 2H), 2.11(br, 1H), 1.94(m, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.30(m, 3H), 0.98(m, 3H), 0.94(d, 6H)

[1674] Example 353. (S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1675] 1 H-NMR (400MHz, CDCl3) δ 7.46(s, 4H), 7.21(d, 1H), 7.03~6.97(m, 1H), 4.99~4.90(m, 2H), 4.79(br, 1H), 3.29(m, 1H), 2.90~2.69(m, 7H), 2.11(br, 1H), 1.94(m, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.33(s, 9H), 1.30(m, 3H), 0.98(m, 3H)

[1677] Example 354. (S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1678] 1 H-NMR (400MHz, CDCl3) δ 7.42(d, 2H), 7.20(d, 1H), 7.13(d, 2H), 7.02~6.99(m, 1H), 4.98~4.88(m, 2H), 4.79(br, 1H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.95(m, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.29(m, 3H), 1.00(m, 2H), 0.98(m, 3H), 0.75(m, 2H)

[1680] Example 355. (S)-quinuclidin-3-yl(6-fluoro-5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1681] 1 H-NMR (400MHz, CDCl3) δ 7.46(d, 2H), 7.19(d, 1H), 6.99(m, 3H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 3.96(s, 3H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1683] Example 356. (S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1684] 1 H-NMR (400MHz, CDCl3) δ 7.44(d, 2H), 7.18(d, 1H), 6.98(m, 3H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.11(m, 2H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.45(t, 3H), 1.44(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1686] Example 357. (S)-quinuclidin-3-yl(6-fluoro-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1687] 1 H-NMR (400MHz, CDCl3) δ 7.44(d, 2H), 7.18(d, 1H), 6.98(m, 3H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 3.97(t, 2H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(m, 3H), 1.72(br, 1H), 1.60(br, 1H), 1.45(t, 3H), 1.44(br, 1H), 1.29(m, 3H), 1.05(t, 3H), 0.98(m, 3H)

[1689] Example 358. (S)-quinuclidin-3-yl(6-fluoro-5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1690] 1 H-NMR (400MHz, CDCl3) δ 7.43(d, 2H), 7.18(d, 1H), 7.02(m, 1H), 6.94(d, 2H), 4.98(m, 1H), 4.88(m, 1H), 4.79(br, 1H), 4.58(m, 1H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.44(br, 1H), 1.31(d, 6H), 1.29(m, 3H), 0.98(m, 3H)

[1692] Example 359. (S)-quinuclidin-3-yl(5-(3-chloro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1693] 1 H-NMR (400MHz, CDCl3) δ 7.54(s, 1H), 7.37(d, 1H), 7.18(d, 1H), 7.02(m, 2H), 4.98(m, 2H), 4.79(br, 1H), 4.57(m, 1H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.44(br, 1H), 1.42(d, 6H), 1.28(m, 3H), 0.98(m, 3H)

[1695] Example 360. (S)-quinuclidin-3-yl(6-fluoro-5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1696] 1 H-NMR (400MHz, CDCl3) δ 7.28(m, 1H), 7.14(d, 1H), 7.00(m, 1H), 6.75(m, 2H), 4.98(m, 2H), 4.79(br, 1H), 3.84(s, 3H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1698] Example 361. (S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1699] 1 H-NMR (400MHz, CDCl3) δ 7.44(d, 12), 7.18(d, 1H), 6.98(m, 3H), 4.98(m, 2H), 4.79(br, 1H), 4.01(t, 2H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.81(m, 2H), 1.72(br, 1H), 1.60(br, 1H), 1.51(m, 2H), 1.43(br, 1H), 1.29(m, 3H), 0.98(m, 6H)

[1701] Example 362. (S)-quinuclidin-3-yl(6-fluoro-5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1702] 1 H-NMR (400MHz, CDCl3) δ 7.44(d, 2H), 7.18(d, 1H), 6.97(m, 3H), 4.98(m, 2H), 4.79(br, 1H), 3.77(d, 2H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(m, 3H), 1.85(br, 1H), 1.81(m, 2H), 1.72(br, 1H), 1.60(br, 1H), 1.51(m, 2H), 1.43(br, 1H), 1.29(m, 3H), 1.05(d, 6H), 0.98(m, 6H)

[1704] Example 363. (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1705] 1H-NMR (400MHz, CDCl3) δ 8.27(s, 1H), 7.74(d, 1H), 7.16(d, 1H), 7.00(m, 1H), 6.83(d, 1H), 4.98(m, 1H), 4.90(m, 1H), 4.79(br, 1H), 4.18(d, 2H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.29(m, 4H), 0.98(m, 3H), 0.64(m, 2H), 0.37(m, 2H)

[1707] Example 364. (S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1708] 1 H-NMR (400MHz, CDCl3) δ 7.31(m, 2H), 7.09(d, 1H), 6.97(m, 1H), 6.89(d, 1H), 4.98(m, 1H), 4.90(m, 1H), 4.79(br, 1H), 3,78(s, 3H), 3.28(m, 1H), 2.88~2.68(m, 7H), 2.11(br, 1H), 1.85(br, 1H), 1.72(br, 1H), 1.60(br, 1H), 1.43(br, 1H), 1.29(m, 4H), 0.98(m, 3H), 0.64(m, 2H), 0.37(m, 2H)

[1710] Example 365. (S)-quinuclidin-3-yl (5-(4-butylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1711] 1H-NMR (400MHz, CDCl3) δ 7.42(d, 2H) 7.25(m, 3H), 6.97(m, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.92~2.65(m, 7H), 2.64(m, 2H), 2.10(m, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.60(m, 2H), 1.59(br, 1H), 1.43(m, 3H), 1.29(m, 3H), 0.98(m, 6H)

[1713] Example 366. (S)-quinuclidin-3-yl(6-fluoro-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1714] 1 H-NMR (400MHz, CDCl3) δ 7.17(s, 4H), 7.98(m, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.77(s, 3H), 3.25(m, 1H), 2.92~2.65(m, 7H), 2.34(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.58(br, 1H), 1.40(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1716] Example 367. (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1717] 1 H-NMR (400MHz, CDCl3) δ 7.17(s, 4H), 6.98(m, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.88(d, 3H), 3.25(m, 1H), 2.92~2.65(m, 7H), 2.32(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.44(t, 4H), 1.28(m, 3H), 0.98(m, 3H)

[1719] Example 368. (S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1720] 1 H-NMR (400MHz, CDCl3) δ δ 7.18(s, 4H), 6.98(m, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.80(m, 2H), 3.25(m, 1H), 2.92~2.71(m, 7H), 2.31(s, 6H), 2.10(m, 1H), 1.85(br, 1H), 1.77(m, 2H), 1.69(br, 1H), 1.60(m, 2H), 1.59(m, 3H), 1.43(br, 1H), 1.29(m, 3H), 0.98(m, 6H)

[1722] Example 369. (S)-quinuclidin-3-yl(6-fluoro-5-(2-methoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1723] 1 H-NMR (400MHz, CDCl3) δ 8.19(d, 1H), 7.23(m, 1H), 7.03(m, 1H), 6.89(s, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.97(s, 3H), 3.25(m, 1H), 2.92~2.71(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.43(br, 1H), 1.29(m, 3H), 0.98(m, 3H)

[1725] Example 370. (S)-quinuclidin-3-yl(6-fluoro-5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1726] 1 H-NMR (400MHz, CDCl3) δ 7.38(m, 1H), 7.36~7.19(m, 3H), 7.05(m, 2H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.90~2.71(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1728] Example 371. (S)-quinuclidin-3-yl (5-(3-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1729] 1 H-NMR (400MHz, CDCl3) δ 7.34(m, 3H), 7.20(m, 2H), 7.00(m, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.90~2.70(m, 7H), 2.68(m, 2H), 2.10(br, 1H), 1.85(br, 1H), 1.69(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 6H), 0.98(m, 3H)

[1731] Example 372. (S)-quinuclidin-3-yl(6-fluoro-5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1732] 1 H-NMR (400MHz, CDCl3) δ 7.34(m, 2H), 7.27(m, 1H), 7.21(m, 1H), 7.15(m, 1H), 6.99(m, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.90~2.72(m, 7H), 2.52(d, 2H), 2.10(br, 1H), 1.90(m, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H), 0.90(d, 6H)

[1734] Example 373. (S)-quinuclidin-3-yl(6-fluoro-5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1735] 1 H-NMR (400MHz, CDCl3) δ 7.37~7.34(m, 3H), 7.22(m, 2H), 6.99(m, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.25(m, 1H), 2.95(m, 1H), 2.90~2.72(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 9H), 0.98(m, 3H)

[1737] Example 374. (S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1738] 1 H-NMR (400MHz, CDCl3) δ 7.53(s, 1H), 7.41(m, 1H), 7.35(m, 1H), 7.22(d, 1H), 7.01(m, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.80(m, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.37(s, 9H), 1.28(m, 3H), 0.98(m, 3H)

[1740] Example 375. (S)-quinuclidin-3-yl(6-fluoro-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1741] 1 H-NMR (400MHz, CDCl3) δ 7.35(m, 1H), 7.22(m, 1H), 7.11(m, 1H), 7.09(s, 1H), 7.01(m, 1H), 6.91(d, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.85(s, 3H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1743] Example 376. (S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamey 트

[1744] 1H-NMR (400MHz, CDCl3) δ 7.35(m, 1H), 7.22(m, 1H), 7.11(m, 1H), 7.09(s, 1H), 7.01(m, 1H), 6.89(d, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 4.09(m, 2H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.45(t, 3H), 1.28(m, 3H), 0.98(m, 3H)

[1746] Example 377. (S)-quinuclidin-3-yl(6-fluoro-2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1747] 1 H-NMR (400MHz, CDCl3) δ 7.33(m, 1H), 7.22(d, 1H), 7.11(m, 1H), 7.09(s, 1H), 7.01(m, 1H), 6.90(d, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.96(m, 2H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.80(m, 2H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 1.15(t, 3H), 0.98(m, 3H)

[1749] Example 378. (S)-quinuclidin-3-yl(6-fluoro-5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1750] 1H-NMR (400MHz, CDCl3) δ 7.32(m, 1H), 7.22(d, 1H), 7.11(m, 1H), 7.09(s, 1H), 7.01(m, 1H), 6.87(d, 1H), 4.95(m, 2H), 4.80(br, 1H), 4.57(m, 1H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.35(d, 6H), 1.28(m, 3H), 0.98(m, 3H)

[1752] Example 379. (S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1753] 1 H-NMR (400MHz, CDCl3) δ 7.34(m, 1H), 7.22(d, 1H), 7.10~7.01(m, 3H), 6.89(d, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 4.00(m, 2H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.78(m, 2H), 1.70(br, 1H), 1.59(br, 1H), 1.53(m, 2H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 6H)

[1755] Example 380. (S)-quinuclidin-3-yl(6-fluoro-5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1756] 1H-NMR (400MHz, CDCl3) δ 7.33(m, 1H), 7.22(d, 1H), 7.11~6.91(m, 3H), 6.89(d, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.76(d, 2H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(m, 2H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 1.05(d, 6H), 0.97(m, 3H)

[1758] Example 381. (S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1759] 1 H-NMR (400MHz, CDCl3) δ 7.16(d 1H), 7.09(d, 1H), 6.97(m, 1H), 6.56(m, 2H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.85(s, 3H), 3.79(s, 3H), 3.25(m, 1H), 2.92~2.71(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1761] Example 382. (S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1762] 1 H-NMR (400MHz, CDCl3) δ 7.12(d, 1H), 7.01(m, 1H), 6.96(m, 2H), 6.87(s, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.79(s, 3H), 3.76(s, 3H), 3.25(m, 1H), 2.93~2.72(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1764] Example 383. (S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1765] 1 H-NMR (400MHz, CDCl3) δ 7.33(m, 1H), 7.05(d, 1H), 6.98(m, 1H), 6.65(d, 2H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.75(s, 6H), 3.25(m, 1H), 2.93~2.72(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1767] Example 384. (S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1768] 1 H-NMR (400MHz, CDCl3) δ 7.20(d, 1H), 7.02(m, 1H), 6.65(s, 2H), 6.48(s, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.83(s, 6H), 3.25(m, 1H), 2.89~2.72(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1770] Example 385. (S)-quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1771] 1H-NMR (400MHz, CDCl3) δ 7.20(d, 1H), 7.08~6.92(m, 3H), 6.93(d, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.93(s, 6H), 3.25(m, 1H), 2.93~2.72(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1773] Example 386. (S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1774] 1 H-NMR (400MHz, CDCl3) δ 7.21(d, 1H), 7.06(d, 1H), 7.03~7.00(m, 2H), 6.86(d, 1H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 3.84(s, 3H), 3.25(m, 1H), 2.90~2.72(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.46(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1776] Example 387. (S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1777] 1 H-NMR (400MHz, CDCl3) δ 7.29(m, 1H), 7.23(m, 1H), 7.17(d, 1H), 7.01(m, 2H), 4.95(s, 1H), 4.85(m, 1H), 4.80(br, 1H), 4.15(m, 2H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.47(t, 3H), 1.45(br, 1H), 1.28(m, 3H), 0.98(m, 3H)

[1779] Example 388. (S)-quinuclidin-3-yl(6-fluoro-5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1780] 1 H-NMR (400MHz, CDCl3) δ 7.19~7.00(m, 3H), 6.97(m, 1H), 4.95(m, 1H), 4.85(m, 1H), 4.80(br, 1H), 4.21(m, 1H), 3.25(m, 1H), 2.90~2.73(m, 7H), 2.31(s, 6H), 2.10(br, 1H), 1.85(br, 1H), 1.70(br, 1H), 1.59(br, 1H), 1.45(br, 1H), 1.30(d, 6H), 1.28(m, 3H), 0.98(m, 3H)

[1782] Examples 389 to 398

[1783] The title compounds of Examples 389 to 398 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl (5'-bromo-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate prepared in Reference Example 8 and the corresponding substituted-phenylboronic acid.

[1785] Example 389. (S)-quinuclidin-3-yl (5'-(4-fluorophenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1786] 1 H-NMR (400MHz, CDCl3) δ 7.54(m, 2H), 7.42(m, 2H), 7.38(s, 1H), 7.13(t, 2H), 5.02(m, 1H), 4.93(m, 1H), 4.74(m, 1H), 3.25(m, 1H), 3.10(m, 1H), 2.91~2.72(m, 6H), 2.09(m, 1H), 1.82(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.92(m, 2H), 0.81(m, 1H), 0.59(m, 1H)

[1788] Example 390. (S)-quinuclidein-3-yl (5'-(4-chlorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1789] 1H-NMR (400MHz, CDCl3) δ 7.55(d, 2H), 7.47(m, 5H), 5.02(m, 1H), 4.91(m, 1H), 4.77(m, 1H), 3.25(m, 1H), 3.10(m, 1H), 2.91~2.72(m, 6H), 2.09(m, 1H), 1.82(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.92(m, 2H), 0.81(m, 1H), 0.59(m, 1H)

[1791] Example 391. (S)-quinuclidin-3-yl (5'-(4-(trifluoromethyl)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1792] 1 H-NMR (400MHz, CDCl3) δ 7.69(s, 4H), 7.47(m, 3H), 5.04(m, 1H), 4.95(m, 1H), 4.77(m, 1H), 3.25(m, 1H), 3.10(m, 1H), 2.91~2.72(m, 6H), 2.09(m, 1H), 1.82(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.91(m, 2H), 0.81(m, 1H), 0.59(m, 1H)

[1794] Example 392. (S)-quinuclidein-3-yl (5'-(4-(trifluoromethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1795] 1 H-NMR (400MHz, CDCl3) δ 7.58(d, 2H), 7.46(m, 2H), 7.40(s, 1H), 7.29(d, 2H), 5.03(m, 1H), 4.94(m, 1H), 4.76(m, 1H), 3.25(m, 1H), 3.09(m, 1H), 2.95~2.76(m, 6H), 2.09(m, 1H), 1.82(m, 1H), 1.72(br, 1H), 1,62(m, 1H), 1.43(br, 1H), 0.92(m, 2H), 0.81(m, 1H), 0.59(m, 1H)

[1797] Example 393. (S)-quinuclidein-3-yl (5'-(3-chlorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1798] 1 H-NMR (400MHz, CDCl3) δ 7.56(s, 1H), 7.44(m, 2H), 7.37(m, 1H), 7.33(m, 1H), 5.02(m, 1H), 4.91(m, 1H), 4.77(m, 1H), 3.25(m, 1H), 2.91~2.72(m, 7H), 2.09(m, 1H), 1.80(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.91(m, 2H), 0.80(m, 1H), 0.59(m, 1H)

[1800] Example 394. (S)-quinuclidin-3-yl (5'-(3-(trifluoromethyl)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1801] 1 H-NMR (400MHz, CDCl3) δ 7.56(s, 1H), 7.44(m, 2H), 7.37(m, 1H), 7.33(m, 1H), 5.02(m, 1H), 4.91(m, 1H), 4.77(m, 1H), 3.25(m, 1H), 2.91~2.72(m, 7H), 2.09(m, 1H), 1.80(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.91(m, 2H), 0.80(m, 1H), 0.59(m, 1H)

[1803] Example 395. (S)-quinuclidein-3-yl (5'-(4-(2-methoxyethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1804] 1 H-NMR (400MHz, CDCl3) δ 7.51(d, 2H), 7.41(m, 3H), 7.01(d, 2H), 5.02(m, 1H), 4.90(m, 1H), 4.75(m, 1H), 4.18(m, 2H), 3.80(m, 2H), 3.48(s, 3H), 3.25(m, 1H), 3.08(m, 1H), 2.91~2.72(m, 5H), 2.09(m, 1H), 1.85(br, 1H), 1.80(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.91(m, 2H), 0.81(m, 1H), 0.59(m, 1H)

[1806] Example 396. (S)-quinuclidin-3-yl (5'-(3-(2-methoxyethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1807] 1 H-NMR (400MHz, CDCl3) δ 7.46(m, 2H), 7.45(s, 1H), 7.35(t, 1H), 7.18(m, 2H), 6.93(d, 1H), 5.04(m, 1H), 4.91(m, 1H), 4.75(m, 1H), 4.19(m, 2H), 3.79(m, 2H), 3.48(s, 3H), 3.25(m, 1H), 3.08(m, 1H), 2.91~2.72(m, 5H), 2.09(m, 1H), 1.85(br, 1H), 1.80(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.91(m, 2H), 0.81(m, 1H), 0.59(m, 1H)

[1809] Example 397. (S)-quinuclidein-3-yl (5'-(4-(methoxymethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1810] 1 H-NMR (400MHz, CDCl3) δ 7.51(d, 2H), 7.43(d, 2H), 7.39(s, 1H), 7.11(d, 2H), 5.22(s, 2H), 5.02(m, 1H), 4.92(m, 1H), 4.75(m, 1H), 3.52(s, 3H), 3.25(m, 1H), 3.08(m, 1H), 2.91~2.72(m, 5H), 2.09(m, 1H), 1.85(br, 1H), 1.80(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.91(m, 2H), 0.79(m, 1H), 0.59(m, 1H)

[1812] Example 398. (S)-quinuclidein-3-yl (5'-(3-(methoxymethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate

[1813] 1H-NMR (400MHz, CDCl3) δ 7.46(m, 2H), 7.45(s, 1H), 7.35(t, 1H), 7.18(m, 2H), 6.93(d, 1H), 5.22(s, 2H), 5.02(m, 1H), 4.92(m, 1H), 4.75(m, 1H), 3.51(s, 3H), 3.25(m, 1H), 3.08(m, 1H), 2.91~2.72(m, 5H), 2.09(m, 1H), 1.85(br, 1H), 1.80(m, 1H), 1.70(br, 1H), 1,60(m, 1H), 1.43(br, 1H), 0.91(m, 2H), 0.80(m, 1H), 0.59(m, 1H)

[1815] Examples 399 to 403

[1816] The title compounds of Examples 399 to 403 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl (5-bromo-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate prepared in Reference Example 9 and the corresponding substituted-phenylboronic acid.

[1818] Example 399. (S)-quinuclidin-3-yl (5-(3-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1819] 1 H NMR (400MHz, CD3OD) δ 7.62~7.49(m, 2H), 7.48~7.29(m, 5H), 5.23(d, 1H), 4.80(brs, 1H), 4.14~4.08(m, 1H), 3.29~3.24(m, 1H), 2.92~2.72(m, 5H), 2.43~2.37(m, 1H), 2.12~2.05(m, 1H), 2.00~1.93(m, 1H), 1.88~1.75(m, 2H), 1.70~1.63(m, 1H), 1.54~1.43(m, 4H), 1.26(brs, 3H)

[1821] Example 400. (S)-quinuclidin-3-yl(5-(2-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate

[1822] 1H NMR (400MHz, CD3OD) δ 7.52~7.45(m, 1H), 7.38~7.22(m, 6H), 5.29~5.21(m, 1H), 4.94~4.90(m, 7H), 4.86~4.77(m, 1H), 4.15~4.07(m, 1H), 3.31~3.22(m, 1H), 2.93~2.71(m, 4H), 2.46~2.37(m, 1H), 2.14~2.05(m, 1H), 2.01~1.93(m, 1H), 1.90~1.74(m, 2H), 1.73~1.61(m, 1H), 1.57~1.48(m, 1H), 1.48~1.40(m, 3H), 1.28~1.24(m, 3H)

[1824] Example 401. (S)-quinuclidin-3-yl(3,3-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1825] 1 H NMR (400MHz, CD3OD) δ 7.89~7.84(m, 2H), 7.66~7.63(m, 2H), 7.53~7.46(m, 2H), 7.35(dd, 1H), 5.26(t, 1H), 4.83~4.78(m, 1H), 3.30~3.26(m, 1H), 2.92~2.73(m, 5H), 2.42(ddd, 1H), 2.14~2.06(m, 1H), 1.96(dd, 1H), 1.89~1.76(m, 2H), 1.71~1.65(m, 1H), 1.55~1.46(m, 4H), 1.30~1.27(m, 3H)

[1827] Example 402. (S)-quinuclidin-3-yl(3,3-dimethyl-5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1828] 1 H NMR (400MHz, CD3OD) δ 7.62(d, 1H), 7.56~7.43(m, 4H), 7.36~7.24(m, 2H), 5.24(brs, 1H), 4.85~4.78(m, 1H), 3.29~3.19(m, 1H), 2.92~2.72(m, 5H), 2.41(dd, 1H), 2.10(d, 1H), 2.03~1.94(m, 1H), 1.88~1.76(m, 2H), 1.71~1.64(m, 1H), 1.54~1.44(m, 4H), 1.28(brs, 3H)

[1830] Example 403. (S)-quinuclidin-3-yl(3,3-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate

[1831] 1 H NMR (400MHz, CD3OD) δ 7.50~7.38(m, 4H), 7.34~7.28(m, 3H), 5.26(t, 1H), 4.83~4.78(m, 1H), 3.29~3.26(m, 1H), 2.92~2.73(m, 5H), 2.42(dt, 1H), 2.10(dd, 1H), 2.00~1.96(m, 1H), 1.88~1.77(m, 2H), 1.70~1.66(m, 1H), 1.52(brs, 1H), 1.43(s, 3H), 1.26(s, 3H)

[1833] Examples 404 and 405

[1834] The title compounds of Examples 404 and 405 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl(6-bromo-dihydrobenzofuran-3-yl)carbamate prepared in Reference Example 10 and the corresponding substituted-phenylboronic acid.

[1836] Example 404. (S)-quinuclidin-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate

[1837] 1 H-NMR (400MHz, CDCl3) δ 7.78(s, 1H), 7.30~7.11(d, 1H), 7.62~7.60(d, 1H), 7.56~7.52(t, 1H), 7.45~7.41(t, 1H), 7.17~7.14(m, 1H), 7.06(s, 1H), 5.42(m, 2H), 4.76~4.72(m, 2H), 4.44~4.41(m, 1H), 3.25~3.19(m, 1H), 2.82~2.69(m, 5H), 2.03~2.00(m, 1H), 1.77~1.65(m, 2H), 1.59~1.57(m, 1H), 1.45~1.30(m, 1H)

[1839] Example 405. (S)-quinuclidin-3-yl (6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate

[1840] 1H-NMR (400MHz, CDCl3) δ 7.48~7.38(m, 4H), 7.21~7.20(d, 1H), 7.15~7.12(m, 1H), 7.04(s, 1H), 5.43~5.38(m, 2H), 4.76~4.71(m, 2H), 4.44~4.41(m, 1H), 3.25~3.19(m, 1H), 2.82~2.66(m, 5H), 2.03~2.01(m, 1H), 1.77~1.65(m, 2H), 1.59~1.55(m, 1H), 1.39(m, 1H)

[1842] Example 406. (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate

[1843] The title compound was prepared in the same manner as in Example 1 using (S)-quinuclidin-3-yl (5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate prepared in Reference Example 11 and 3-fluorophenylboronic acid.

[1844] 1 H-NMR (400MHz, CDCl3) δ 7.52~7.44(m, 2H), 7.38~7.27(m, 2H), 7.23~7.21(d, 1H), 7.02~6.98(t, 1H), 6.85~6.83(d, 1H), 5.22~5.19(m, 1H), 5.09~5.07(m, 1H), 4.76~4.74(m, 1H), 3.26~3.20(m, 1H), 2.82~2.64(m, 5H), 1.77~1.68(m, 2H), 1.66~1.53(m, 4H), 1.46~1.39(m, 4H), 1.27(m, 1H)

[1846] Examples 407 to 411

[1847] The title compounds of Examples 407 to 411 were prepared in the same manner as in Example 1 using the (S)-quinuclidin-3-yl (6-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate prepared in Reference Example 12 and the corresponding substituted-phenylboronic acid.

[1849] Example 407. (S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate

[1850] 1 H-NMR (400MHz, CDCl3) δ 7.39~7.31(m, 3H), 7.27~7.22(t, 1H), 7.12~7.09(t, 1H), 7.06~7.02(t, 1H), 6.95(s, 1H), 5.36~5.30(m, 1H), 5.06~5.04(d, 1H), 4.76~4.74(m, 1H), 3.24~3.19(m, 1H), 2.81~2.69(m, 5H), 1.76~1.67(m, 2H), 1.54~1.49(m, 4H), 1.45~1.43(m, 4H), 1.40~1.26(m, 1H)

[1852] Example 408. (S)-quinuclidin-3-yl (6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate

[1853] 1 H-NMR (400MHz, CDCl3) δ 7.53(s, 1H), 7.43~7.31(m, 4H), 7.1~7.09(m, 1H), 6.95(s, 1H), 5.18~5.14(m, 1H), 5.07~5.05(m, 1H), 4.77~4.75(m, 1H), 3.26~3.21(m, 1H), 2.89~2.65(m, 5H), 1.77~1.73(m, 2H), 1.69~1.68(m, 4H), 1.56~1.44(m, 4H), 1.40(m, 1H)

[1855] Example 409. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate

[1856] 1 H-NMR (400MHz, CDCl3) δ 7.79(s, 1H), 7.73~7.71(d, 1H), 7.62~7.60(d, 1H), 7.57~7.53(t, 1H), 7.41~7.37(t, 1H), 7.15~7.12(t, 1H), 6.98(s, 1H), 5.23~5.19(t, 1H), 5.08~5.06(d, 1H), 4.77~4.75(m, 1H), 3.26~3.21(m, 1H), 2.89~2.65(m, 5H), 1.78~1.69(m, 2H), 1.57~1.53(m, 3H), 1.46~1.40(m, 4H), 1.40~1.27(m, 1H)

[1858] Example 410. (S)-quinuclidin-3-yl(2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate

[1859] 1 H-NMR (400MHz, CDCl3) δ 7.47~7.43(m, 2H), 7.39~7.35(m, 2H), 7.22~7.20(d, 1H), 7.13~7.09(t, 1H), 6.96(s, 1H), 5.19~5.14(t, 1H), 5.08~5.06(d, 1H), 4.76~4.75(m, 1H), 3.27~3.21(m, 1H), 2.84~2.66(m, 5H), 1.77~1.68(m, 2H), 1.56~1.53(m, 4H), 1.46~1.40(m, 4H), 1.39~1.27(m, 1H)

[1861] Example 411. (S)-quinuclidin-3-yl (6-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate

[1862] 1 H-NMR (400MHz, CDCl3) δ 7.35~7.27(m, 2H), 7.23~7.22(m, 2H), 7.19~7.17(m, 1H), 7.03(m, 1H), 6.97(s, 1H), 5.21~5.18(m, 3H), 5.05~5.00(m, 1H), 4.74~4.73(m, 1H), 3.49(s, 3H), 3.23~3.18(m, 1H), 2.80~2.66(m, 5H), 2.04(m, 1H), 1.76~1.67(m, 2H), 1.56~1.38(m, 8H)

[1864] Test Example 1: Evaluation of inhibitory activity against GCS

[1865] The inhibitory activity of the compounds according to the present invention against GCS is described in the known literature (Hayashi Y et al., A sensitive and reproducible assay to measure the activity of glucosylceramide synthase and lactosylceramide synthase using HPLC and fluorescent substrates, Analytical BiochemistryIt was evaluated as follows according to the method described in 345 (2005) 181-186). Ibiglustat, known as a GCS inhibitor, was used as a control substance.

[1866] (1) material

[1867] A549 cells (ATCC, CCL-185)

[1868] NBD C6-ceramide (Thermo Fisher, N1154)

[1869] UDP-glucose (Sigma, U4625)

[1870] Potassium chloride (Sigma, P9333)

[1871] Ultra Pure 0.5 M EDTA (Invitrogen, 15575-038)

[1872] BCA Protein Assay Kit (thermo, 23227)

[1873] Ibiglustat (Shanghai Systeam Biochem Co., ltd, Genz-682452)

[1874] HEPES (sigma, H3375)

[1875] Protease Phosphatase Inhibitor Cocktail (CST, 5872s)

[1876] DMEM (GIBCO, 11995-065)

[1877] FBS (GIBCO, 16000-044)

[1878] Antibiotic-Antimycotic (100X) (GIBCO, 15240-112)

[1879] 200 mM L-glutamine (GIBCO, 25030081)

[1880] PBS (GIBCO, 10010-023)

[1881] 0.25% Trypsin-EDTA (GIBCO, 25200-056)

[1882] Dimethyl sulfoxide (Sigma, 34869)

[1883] 2-Propanol, HPLC grade (Burdick & Jackson, AH323-4)

[1884] Hexane, HPLC grade (Burdick & Jackson, AH216-4)

[1885] Chloroform (Sigma, C2432)

[1886] Methanol (Merck, 1.06009.1011)

[1887] (2) Protocol

[1888] <1> Preparation of cell lysates

[1889] A549 cells (ATCC, CCL-185) were cultured in DMEM medium supplemented with 10% fetal bovine serum (FBS), 1x antibiotic-antimycotic, and 1x L-glutamine at 37°C in a 5% CO2 incubator. Cells attached to the culture dish were washed with phosphate-buffered saline (PBS), scraped off with a cell scraper, and collected in 50 ml tubes by centrifugation (4000 rpm, 3 min, 4°C). The cell pellet was suspended in lysis buffer (50 mM HEPES, pH 7.3, containing 1x protase phosphatase inhibitor cocktail), lysed by sonication, and the lysate was centrifuged (13000 rpm, 10 min, 4°C). The obtained supernatant was used for protein quantification analysis. Protein levels were measured using a BCA protein assay kit, with bovine serum albumin used as the standard.

[1890] <2> GCS enzyme reaction

[1891] The following reaction substances were sequentially added to a deep 96-well plate to initiate the enzymatic reaction. Subsequently, the enzymatic reaction was carried out at 37°C for 90 minutes.

[1892]

[1893] <3> lipid extraction

[1894] 100 µl of chloroform / methanol (2:1, v / v) was added to stop the enzymatic reaction. After vortexing for 15 seconds, the mixture was centrifuged (4000 rpm, 10 min, 18°C). 50 µl of the lower layer was transferred to a new dip 96-well plate and dried using a vacuum concentrator.

[1895] <4> HPLC analysis

[1896] Lipids in 100 µl of isopropyl alcohol / n - After dissolving in hexane / H2O (55:44:1, v / v / v), it was transferred to a glass vial for HPLC (Agilent, 8004-HP-H / i3u). 100 µl of the sample was autoloaded onto a normal-phase column (Intersil SIL 150A-5, 4.6x250mm, GL Sciences, Japan), and isopropyl alcohol / n After eluting with hexane / H2O (55:44:1, v / v / v) at a flow rate of 2.0 ml / min, fluorescence was measured using a fluorescence detector (Agilent, 1260 FLD Spectra). At this time, the excitation and emission wavelengths were set to 470 nm and 530 nm, respectively.

[1897] <5> Data analysis

[1898] Data analysis was performed using the following formula.

[1899] % Area (Sample) = Area (GlcCer) / [Area (Cer) + Area (GlcCer)] X 100

[1900] % GCS Activity = [Area (Sample) - Area (Ibiglustat)] / [Area (DMSO) - Area (Ibiglustat)] X 100

[1901] The obtained % GCS active data was analyzed using the software GraphPad Prism (Ver 5.01), and IC 50Values ​​were calculated. The results are as shown in Tables 1 to 4 below.

[1902] Examples IC 50 (nM) Examples IC 50 (nM) Examples IC 50 (nM) 1 9.8 41 16.9 81 2.8 2 17.2 42 23.6 82 2.5 3 21.7 43 33.4 83 7.5 4 11.0 44 18.6 84 7.3 5 3.8 45 33.3 85 3.1 6 1.7 46 8.9 86 3.6 7 1.1 47 37.5 87 9.4 8 1.2 48 58.2 88 2.9 9 2.4 49 9.3 89 8.5 10 2.9 50 9.7 90 11.0 11 22.2 51 7.1 91 2.3 12 14.8 52 14.9 92 16.1 13 9.5 53 8.1 93 1.4 14 8.9 54 20.65 94 9.5 15 11.8 55 32.42 95 11.2 16 12.7 56 32.1 96 6.9 17 3.7 57 2.5 97 3.0 18 5.3 58 2.8 98 2.8 19 12.7 59 5.44 99 6.0 20 16.0 60 16.9 100 2.1 21 12.3 61 12.7 101 1.9 22 15.1 62 13.13 102 4.6 23 10.2 63 7.55 103 1.7 24 1.6 64 3.9 104 1.9 25 65.7 65 5.5 105 1.8 26 48.1 66 30.9 106 1.2 27 55.3 67 12.3 107 1.1 28 79.2 68 15.2 108 2.3 29 38.0 69 108.8 109 3.6 30 34.0 70 20.1 110 6.0 31 41.5 71 13.0 111 3.5 32 71.2 72 10.7 112 2.5 33 25.8 73 22.5 113 6.4 34 13.7 74 24.1 114 3.8 35 20.29 75 14.9 115 3.6 36 14.28 76 5.9 116 1.8 37 33.9 77 2.9 117 3.5 38 33.9 78 2.1 118 14.2 39 26.9 79 2.6 119 10.9 40 40.4 80 3.0 120 4.2

[1904] Examples IC 50 (nM) Examples IC 50 (nM) Examples IC 50 (nM) 121 0.7 161 1.6 201 3.9 122 6.8 162 7.0 202 6.1 123 0.9 163 0.6 203 1.2 124 3.1 164 0.6 204 8.3 125 17.0 165 13.7 205 1.0 126 14.0 166 1.6 206 0.6 127 5.9 167 0.5 207 6.2 128 2.8 168 2.7 208 3.7 129 5.1 169 1.9 209 3.0 130 1.3 170 6.1 210 0.6 131 2.1 171 2.5 211 1.2 132 3.7 172 1.8 212 1.2 133 4.3 173 7.2 213 2.0 134 6.8 174 4.5 214 1.7 135 1.4 175 2.3 215 1.4 136 0.7 176 1.7 216 0.7 137 2.9 177 3.2 217 2.4 138 1.3 178 3.2 218 0.6 139 10.0 179 4.3 219 2.9 140 1.0 180 1.4 220 1.2 141 3.0 181 0.3 221 1.5 142 1.5 182 2.1 222 2.9 143 4.5 183 2.8 223 0.9 144 1.0 184 6.5 224 2.9 145 4.6 185 0.5 225 2.9 146 3.3 186 9.5 226 6.3 147 1.9 187 4.5 227 2.2 148 1.4 188 8.4 228 3.8 149 1.6 189 2.2 229 4.4 150 0.7 190 2.1 230 1.2 151 2.2 191 9.3 231 0.5 152 1.7 192 3.7 232 0.8 153 2.8 193 2.0 233 1.2 154 1.7 194 10.1 234 0.6 155 1.1 195 6.4 235 0.9 156 2.6 196 0.9 236 3.4 157 0.6 197 1.7 237 5.2 158 3.4 198 1.2 238 2.4 159 4.3 199 0.7 239 7.6 160 2.0 200 0.6 240 3.5

[1906] Examples IC 50 (nM) Examples IC 50 (nM) Examples IC 50 (nM) 241 1.3 281 0.6 321 4.3 242 5.9 282 0.7 322 4.4 243 1.4 283 1.3 323 5.4 244 1.8 284 0.8 324 0.8 245 3.0 285 0.5 325 0.8 246 3.9 286 0.4 326 0.7 247 11.9 287 0.7 327 1.8 248 3.0 288 1.2 328 0.4 249 9.0 289 0.8 329 4.9 250 4.8 290 1.4 330 5.1 251 1.1 291 1.7 331 3.7 252 7.4 292 1.6 332 5.1 253 3.4 293 2.0 333 1.7 254 7.0 294 4.0 334 0.1 255 6.2 295 2.7 335 4.3 256 1.9 296 1.2 336 4.0 257 2.1 297 0.7 337 8.9 258 5.9 298 6.6 338 1.3 259 2.8 299 2.2 339 2.1 260 1.0 300 1.4 340 1.3 261 3.1 301 1.2 341 3.2 262 1.5 302 1.4 342 1.2 263 2.6 303 4.4 343 2.3 264 3.6 304 3.5 344 2.1 265 0.7 305 4.1 345 3.8 266 0.7 306 0.8 346 2.4 267 2.8 307 1.5 347 2.6 268 0.7 308 0.3 348 6.7 269 5.2 309 0.6 349 0.8 270 1.1 310 0.7 350 0.4 271 5.1 311 2.4 351 0.5 272 9.9 312 2.2 352 0.7 273 5.2 313 1.3 353 1.2 274 2.7 314 0.9 354 0.3 275 5.1 315 0.9 355 1.1 276 1.3 316 1.9 356 0.5 277 0.8 317 2.0 357 0.3 278 0.6 318 2.3 358 0.3 279 0.8 319 1.0 359 2.4 280 0.4 320 0.9 360 0.7

[1908] Examples IC 50 (nM) Examples IC 50 (nM) Examples IC 50 (nM) 361 0.1 381 1.6 401 73 362 0.2 382 0.5 402 74.5 363 0.1 383 1.9 403 155.2 364 0.1 384 1.3 404 5.3 365 0.3 385 6.9 405 7.1 366 5.3 386 0.2 406 31.1 367 4.3 387 1.8 407 4.8 368 6.2 388 11.5 408 3.0 369 2.8 389 19.0 409 3.3 370 1.8 390 18.6 410 3.0 371 2.6 391 21.4 411 10.9 372 3.9 392 10.2 373 3.9 393 4.8 374 7.7 394 5.6 375 0.9 395 2.4 376 2.6 396 2.7 377 1.4 397 0.8 378 1.7 398 0.9 379 0.6 399 103.7 380 1.7 400 65.6

[1909] From the results of Tables 1 to 4 above, it can be seen that the compounds of the present invention exhibit excellent inhibitory activity against GCS.

[1911] Test Example 2: Evaluation of inhibitory activity on GM1 production

[1912] GM1 is the end product of sphingolipid metabolism and is expressed on the cell membrane, making it easy to detect. Furthermore, the amount of GM1 represents the conversion of ceramide to glucosylceramide. Therefore, the inhibitory activity of the compounds of the present invention on GM1 production is based on the known literature (Dijkhuis et al., Gangliosides do not affect ABC transporter function in human neuroblastoma cells. The Journal of Lipid Research It was evaluated as follows according to the method described in 47 (2006). 1187-1195). Ibiglustat, known as a GCS inhibitor, was used as a control substance.

[1913] (1) material

[1914] Jurkat cells, clone E6-1 (ATCC, TIB-152)

[1915] Cholera toxin subunit (CTB), FITC (Sigma, C1655)

[1916] Ibiglustat (Shanghai Systeam Biochem Co., ltd, Genz-682452)

[1917] DMSO (Sigma, D2650)

[1918] Fixed buffer (BD, 554655)

[1919] RPMI 1640 (Gibco, A1049101)

[1920] FBS (Gibco, 16000-044)

[1921] Antibiotic-Antimycotic (100X) (Gibco, 15240-122)

[1922] FACS Sheath Fluid (BD, 342003)

[1923] Jurkat cells were cultured in RPMI 1640 medium supplemented with 10% FBS and 1X Antibiotic-Antimycotic. The wash solution was prepared by adding 10 ml of FBS to 490 ml of FACS Sheath Fluid. The CTB-FITC solution was prepared by diluting the stock CTB-FITC solution (10 mg / ml) with the wash solution to a final concentration of 2 μg / ml.

[1924] (2) Protocol

[1925] Cell suspension (1X10⁶ 5After preparing cells / ml, 200 µl was dispensed into each well of a 96-well plate (20,000 cells / well). The compound was added to each well to achieve a final concentration of 0.05–3000 nM (3 fold, 11 points), and then cultured in a CO2 incubator at 37°C for 72 hours. The medium was removed by centrifugation at 1500 rpm for 3 minutes, and the cells were resuspended in 200 µl of wash solution per well. The wash solution was removed by centrifugation at 1500 rpm for 3 minutes, and the cells were resuspended by adding 200 µl of 2 µg / ml CTB-FITC solution. The resulting suspension was incubated at 4°C for 60 minutes while protecting it from light. After removing the CTB-FITC solution by centrifugation at 1500 rpm for 3 minutes, the plates were washed with 200 µl of washing solution, and the washing process was repeated twice. After washing, the plates were centrifuged at 1500 rpm for 3 minutes to remove the washing solution, and 200 µl of fixation buffer was added to completely resuspend the cells. Guava TM IC from the value obtained by quantifying FITC fluorescence using easyCyte 5HT (Merck Milipore, 0500-4005) 50 Decided.

[1926] Data analysis was performed using the following formula.

[1927] % MFI (Mean Fluorescence Intensity) = (Fluorescence value of drug-treated group / Fluorescence value of DMSO-treated group) X 100

[1928] % Cells = (Cell concentration in well / Cell concentration in DMSO-treated group) X 100

[1929] % MFI and % cell data were analyzed using the software GraphPad Prism (Ver 5.01), and IC 50 The values ​​were calculated. The results are as shown in Tables 5 to 8 below.

[1930] Examples IC 50 (nM) Examples IC 50 (nM) Examples IC 50 (nM) 1 139.2 48 65.7 88 11.1 2 201.8 49 61.4 89 50.0 3 142.5 50 52.3 90 37.9 4 95.8 51 30.2 91 25.1 5 70.2 52 82.3 92 43.9 6 39.4 53 80.0 93 10.5 7 36.8 54 161 94 23.6 8 27.4 55 172.8 95 49.7 9 93.1 56 209.9 96 16.2 10 65.5 57 49.9 97 9.3 11 123.0 58 87.8 98 7.5 12 73.0 59 164.5 99 22.2 13 41.7 60 111.7 100 21.5 14 54.3 61 39.6 101 8.7 15 34.4 62 103 102 17.4 16 56.1 63 116.7 103 19.5 17 27.6 64 74.7 104 16.9 18 31.6 65 56.2 105 15.2 19 20.3 66 127.7 106 5.8 20 125.9 67 144.0 107 6.3 21 126.6 68 91.8 108 7.6 22 89.6 69 399.8 109 7.8 23 63.7 70 70.9 110 15.1 24 17.4 71 64.3 111 32.0 25 105.9 72 58.2 112 35.6 26 67.2 73 26.0 113 54.8 27 35.7 74 13.0 114 33.7 28 52.0 75 8.3 115 38.3 29 63.0 76 3.7 116 16.7 30 106.8 77 6.3 117 41.8 31 65.5 78 3.5 118 38.4 32 120.2 79 3.9 119 38.3 37 55.2 80 4.1 120 28.4 38 62.0 81 12.2 121 4.7 39 51.9 82 3.2 122 50.8 43 182.8 83 3.7 123 9.3 44 35.2 84 4.9 124 22.3 45 57.3 85 11.6 125 9.5 46 19.2 86 13.8 126 50.5 47 26.6 87 42.8 127 18.2

[1932] Examples IC 50 (nM) Examples IC 50 (nM) Examples IC 50 (nM) 128 18.4 168 9.6 208 67.4 129 36.8 169 9.8 209 32.1 130 10.0 170 13.0 210 7.5 131 10.6 171 17.0 211 13.2 132 29.2 172 48.5 212 19.1 133 22.6 173 34.8 213 39.8 134 43.2 174 40.2 214 64.2 135 8.1 175 42.8 215 14.9 136 1.7 176 27.6 216 28.7 137 12.1 177 22.9 217 72.1 138 9.1 178 26.9 218 6.7 139 74.4 179 41.0 219 30.4 140 10.5 180 28.1 220 17.6 141 39.9 181 5.5 221 16.9 142 20.5 182 20.9 222 25.6 143 25.2 183 18.6 223 5.2 144 6.2 184 40.0 224 18.8 145 23.0 185 11.1 225 21.3 146 14.1 186 82.6 226 57.0 147 14.0 187 31.7 227 10.2 148 30.0 188 46.2 228 48.6 149 27.6 189 23.0 229 56.2 150 6.8 190 13.3 230 30.8 151 37.9 191 123.4 231 24.3 152 32.5 192 25.8 232 12.5 153 41.4 193 15.3 233 23.3 154 27.4 194 47.6 234 13.6 155 8.4 195 36.1 235 6.5 156 46.7 196 23.2 236 32.4 157 2.8 197 8.7 237 29.2 158 17.1 198 11.7 238 13.2 159 12.7 199 5.5 239 48.9 160 22.7 200 3.7 240 51.3 161 10.8 201 38.2 241 51.3 162 38.8 202 26.3 242 64.4 163 12.2 203 8.2 243 21.4 164 6.5 204 57.2 244 38.0 165 15.6 205 7.6 245 23.0 166 26.3 206 14.0 246 14.7 167 3.8 207 58.6 247 41.0

[1934] Examples IC 50 (nM) Examples IC 50 (nM) Examples IC 50 (nM) 248 14.9 288 11.2 328 11.4 249 37.0 289 7.4 329 65.8 250 33.0 290 12.3 330 52.7 251 7.2 291 13.5 331 22.6 252 43.9 292 7.8 332 158.4 253 37.2 293 8.7 333 45 254 45.2 294 10.4 334 20.9 255 35.8 295 35.0 335 50.4 256 24.6 296 15.6 336 48 257 27.4 297 3.0 337 65 258 17.4 298 63.2 338 53.7 259 10.2 299 25.3 339 62.5 260 14.4 300 23.0 340 43.8 261 51.5 301 9.6 341 61.9 262 34.4 302 4.0 342 21.6 263 34.9 303 27.2 343 45.7 264 14.4 304 23.5 344 51 265 6.7 305 9.8 345 45.7 266 4.7 306 27.5 346 38.3 267 83.1 307 30.2 347 46.8 268 2.5 308 5.5 348 44.1 269 6.5 309 11.2 349 10.3 270 2.3 310 16.3 350 4.5 271 30.6 311 27.0 351 7.4 272 49.3 312 13.1 352 5.7 273 13.4 313 7.3 353 12.7 274 10.3 314 7.7 354 5.9 275 25.0 315 11.3 355 62.8 276 33.2 316 13.3 356 21.6 277 2.7 317 10.3 357 5.3 278 6.0 318 20.0 358 7.7 279 7.3 319 7.7 359 33.1 280 1.6 320 8.5 360 39.0 281 5.0 321 31.9 361 2.1 282 5.6 322 24.4 362 2.5 283 17.2 323 78.9 363 8.7 284 8.5 324 5.8 364 17.2 285 3.7 325 2.1 365 2.4 286 4.1 326 10.8 366 79.4 287 4.1 327 16.8 367 68.2

[1936] Examples IC 50 (nM) Examples IC 50 (nM) Examples IC 50 (nM) 368 22.9 388 93.1 408 15.8 369 171.7 389 76.5 409 14.9 370 39.3 390 44.1 410 13.0 371 24.8 391 55.3 411 79.3 372 46.2 392 41.9 373 31.2 393 54.9 374 26.5 394 48.8 375 23 395 30.9 376 85.9 396 39.6 377 35.5 397 17.4 378 87.5 398 36.6 379 15.8 399 43.59 380 36.5 400 107.5 381 59.9 401 15.13 382 31.3 402 19.5 383 123.1 403 85.31 384 83.2 404 25.9 385 331.6 405 44.7 386 29.5 406 119.7 387 48.2 407 44.4

[1937] From the results of Tables 5 to 8 above, it can be seen that the compounds of the present invention exhibit excellent inhibitory activity against GM1 production.

Claims

Claim 1 Compound of Chemical Formula 1 below or a pharmaceutically acceptable salt thereof: <Chemical Formula 1> In the formula, L is -O-, -CO-, -CR1R2-, or -NR3-, Y and Z are independently -CR1R2-; -NR3-; -O-; or -S-, and R1 and R2 are independently hydrogen; halogen; C1–C6 alkyl; C1–C6 alkyl having a nitrogen, oxygen, or sulfur atom; C3–C 10 Cycloalkyl; ternary to twelve-membered heterocyclic; or C1 to C6 alkoxy; or R1 and R2 together with the carbon atom to which they are bonded are C3 to C 10 Forming a cycloalkyl group, where R3 is hydrogen; C1–C6 alkyl; C1–C6 alkyl having a nitrogen, oxygen, or sulfur atom; C3–C 10 cycloalkyl; 3 to 12-membered heterocyclic; or C1 to C6 alkoxy, where X is hydrogen; halogen; C1 to C6 alkyl; C1 to C6 alkyl substituted with 1 to 3 halogens; C1 to C6 alkyl having a nitrogen, oxygen, or sulfur atom; C1 to C6 alkoxy; or C1 to C6 alkoxy substituted with 1 to 3 halogens, and W is a bond, -CH2-, -O-, -NH-, -CH2CH2-, -CH=CH-, or -C≡C-, and ring A is a 6 to 12-membered aryl; 5 to 12-membered heteroaryl; C3 to C 10 Cycloalkyl; or 3 to 12-membered heterocyclic, wherein X1, X2, X3, and X4 are independently hydrogen; cyano; halogen; C1–C6 alkyl; C1–C6 alkoxy-C1–C6 alkyl; C1–C6 alkyl substituted with 1 to 3 halogens; C3–C 10 Cycloalkyl; ternary to twelve-membered heterocyclic; C1–C6 alkoxy; C1–C6 alkoxy substituted with 1 to 3 halogens; C1–C6 alkoxy-C1–C6 alkoxy; morpholineyl-C1–C6 alkoxy; mono- or di-C1–C6 alkylamino-C1–C6 alkoxy; C3–C 10 It is cycloalkyl-C1~C6 alkoxy; C1~C6 alkylthio; amino; mono- or di-C1~C6 alkylamino; C1~C6 alkylcarbonyl; hydroxy; or nitro. Claim 2 A compound or a pharmaceutically acceptable salt thereof characterized in that L is -O- in claim 1. Claim 3 A compound or a pharmaceutically acceptable salt thereof, characterized in that, in claim 1, Y and Z are independently -O- or -CR1R2-. Claim 4 In paragraph 3, R1 and R2 are independently hydrogen or C1-C6 alkyl; or R1 and R2 are C3-C6 alkyl together with the carbon atom to which they are bonded. 10 A compound characterized by forming a cycloalkyl group or a pharmaceutically acceptable salt thereof. Claim 5 A compound or a pharmaceutically acceptable salt thereof, characterized in that, in claim 1, Y is -O- and Z is -CR1R2-. Claim 6 A compound or a pharmaceutically acceptable salt thereof, characterized in that X is hydrogen, a halogen, or a C1-C6 alkoxy in claim 1. Claim 7 A compound or a pharmaceutically acceptable salt thereof characterized in that W is bonded or -CH=CH- in claim 1. Claim 8 A compound or a pharmaceutically acceptable salt thereof, characterized in that the A ring is a 6- to 12-membered aryl in claim 1. Claim 9 In claim 8, a compound or a pharmaceutically acceptable salt thereof characterized in that the A ring is phenyl, naphthalenyl, or biphenyl. Claim 10 A compound or a pharmaceutically acceptable salt thereof, characterized in that the A ring is a 5 to 12-membered heteroaryl in claim 1. Claim 11 A compound or a pharmaceutically acceptable salt thereof, characterized in that the A ring is benzodioxolyl, pyridinyl, thiopheneyl, quinolineyl, isoquinolineyl, benzofuranyl, benzo[b]thiopheneyl, quinoxalinyl, or furanyl, in accordance with claim 10. Claim 12 A compound or a pharmaceutically acceptable salt thereof, characterized in that the A ring is a heterocyclic ring of 3 to 12 members in claim 1. Claim 13 A compound or a pharmaceutically acceptable salt thereof, characterized in that the A ring is 2,3-dihydrobenzodioxinyl, 2,3-dihydrobenzofuranyl, 3,4-dihydro-2H-benzo[b][1,4]oxazinyl, chromanyl, or 3,4-dihydro-2H-benzo[b][1,4]dioxepinyl. Claim 14 In claim 1, X1, X2, X3, and X4 are independently hydrogen; cyano; halogen; C1–C6 alkyl; C1–C6 alkoxy-C1–C6 alkyl; C1–C6 alkyl substituted with 1 to 3 halogens; C3–C 10 Cycloalkyl; Morphoyl; C1–C6 alkoxy; C1–C6 alkoxy substituted with 1 to 3 halogens; C1–C6 alkoxy-C1–C6 alkoxy; Morphoyl-C1–C6 alkoxy; Mono- or di-C1–C6 alkylamino-C1–C6 alkoxy; C3–C 10 A compound characterized by being cycloalkyl-C1-C6 alkoxy; C1-C6 alkylthio; mono- or di-C1-C6 alkylamino; or C1-C6 alkylcarbonyl, or a pharmaceutically acceptable salt thereof. Claim 15 In claim 1, L is -O-, Y and Z are independently -O- or -CR1R2-, and R1 and R2 are independently hydrogen or C1-C6 alkyl; or R1 and R2 are C3-C6 alkyl together with the carbon atom to which they are bonded. 10 Forming a cycloalkyl group, where X is hydrogen, a halogen, or a C1-C6 alkoxy, W is a bond or -CH=CH-, A ring is a 6- to 12-membered aryl, a 5- to 12-membered heteroaryl, or a 3- to 12-membered heterocyclic, and X1, X2, X3, and X4 are independently hydrogen; cyano; halogen; C1-C6 alkyl; C1-C6 alkoxy-C1-C6 alkyl; C1-C6 alkyl substituted with 1 to 3 halogens; C3-C 10 Cycloalkyl; Morphoyl; C1–C6 alkoxy; C1–C6 alkoxy substituted with 1 to 3 halogens; C1–C6 alkoxy-C1–C6 alkoxy; Morphoyl-C1–C6 alkoxy; Mono- or di-C1–C6 alkylamino-C1–C6 alkoxy; C3–C 10 A compound characterized by being cycloalkyl-C1-C6 alkoxy; C1-C6 alkylthio; mono- or di-C1-C6 alkylamino; or C1-C6 alkylcarbonyl, or a pharmaceutically acceptable salt thereof. Claim 16 A compound or a pharmaceutically acceptable salt thereof characterized in that, in paragraph 15, Y is -O- and Z is -CR1R2-. Claim 17 In paragraph 15, a compound or a pharmaceutically acceptable salt thereof characterized in that the A ring is phenyl, naphthalenyl, or biphenyl. Claim 18 A compound or a pharmaceutically acceptable salt thereof, characterized in that the A ring is benzodioxolyl, pyridinyl, thiopheneyl, quinolineyl, isoquinolineyl, benzofuranyl, benzo[b]thiopheneyl, quinoxalinyl, or furanyl, in accordance with claim 15. Claim 19 A compound or a pharmaceutically acceptable salt thereof, characterized in that the A ring is 2,3-dihydrobenzodioxinyl, 2,3-dihydrobenzofuranyl, 3,4-dihydro-2H-benzo[b][1,4]oxazinyl, chromanyl, or 3,4-dihydro-2H-benzo[b][1,4]dioxepinyl. Claim 20 In claim 1, a compound selected from the group consisting of the following compounds or a pharmaceutically acceptable salt thereof: (S)-quinuclidin-3-yl (5-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-( p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2-chlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(; p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,5-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,4-difluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3,5-dichlorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (6-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (6-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-6-(; p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(; p -tolyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-(methylthio)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(; tert -butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,3-dihydrobenzofuran-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-(2-morphorinoethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-(2,2,2-trifluoroethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-(2-morphorinoethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethyl)pyridine-4-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-dichloropyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,3-dichloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(dimethylamino)-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(chroman-6-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-methoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(thiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-methylthiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-(2-(dimethylamino)ethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(isoquinoline-8-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(isoquinoline-5-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(isoquinoline-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(; tert -butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-morpholinophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(methoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(2,2-difluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-methyl-4-morpholinophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluoro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-8-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(benzofuran-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(benzofuran-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2,4-dichloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-difluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-5-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-methoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(; tert -butoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,6-dimethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(benzo[b]thiophene-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-( tert -butoxy)pyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-methoxy-5-(trifluoromethyl)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-methoxynaphthalene-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-([1,1'-biphenyl]-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(quinoxalin-6-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(furan-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-isopropoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-ethoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-methoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-butoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-butoxy-3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2,4-dipropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-chloro-4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-fluoro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-chloro-2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-6-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-fluoro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(5-chloro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,4-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-isopropyl-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(5-methylfuran-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(benzo[b]thiophene-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(; tert -butyl)-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-5-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-cyano-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-ethoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluoro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-methyl-4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(3-(methylthio)-5-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluoro-4-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-ethoxy-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,4-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-methoxy-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2-ethoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-fluoro-5-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-ethoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-ethoxypyridin-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-isopropoxypyridin-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(6-propoxypyridine-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-butoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-(2-methoxyethoxy)pyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-isobutoxypyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,4-dimethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-acetylthiophene-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-((E)-3-fluorostyryl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-((E)-4-ethylstyryl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-((E)-2-cyclohexylvinyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-ethylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(; tert -butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-isopropylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-isopropoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-isobutylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(3-fluorophenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(3-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(3-isopropoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(3-ethylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(3-isopropylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-( tert -butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(thiophene-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(furan-3-yl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(2-fluoro-4-methoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-methoxy-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(; tert -butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-methoxy-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-butylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-methoxy-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (6-methoxy-5-(2-methoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(; tert -butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-methoxy-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-methoxy-2,2-methyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-isobutoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-(; tert -butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-butylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (6-fluoro-5-(2-methoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-(; tert -butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-fluoro-5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (6-fluoro-5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5'-(4-fluorophenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate; (S)-quinuclidin-3-yl (5'-(4-chlorophenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5'-(4-(trifluoromethyl)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5'-(4-(trifluoromethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5'-(3-chlorophenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5'-(3-(trifluoromethyl)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5'-(4-(2-methoxyethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5'-(3-(2-methoxymethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5'-(4-(methoxymethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5'-(3-(methoxymethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (3,3-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (3,3-dimethyl-5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (3,3-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate;(S)-quinuclidin-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate;(S)-quinuclidin-3-yl (6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate; and (S)-quinuclidin-3-yl (6-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate.; Claim 21 delete Claim 22 delete Claim 23 delete Claim 24 In claim 1, a compound selected from the group consisting of the following compounds or a pharmaceutically acceptable salt thereof: (S)-quinuclidin-3-yl (5-(3-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-( tert -butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (2,2-diethyl-5-(4-ethylphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate;(S)-quinuclidin-3-yl (5-(4-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5'-(4-chlorophenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate; and (S)-quinuclidin-3-yl (5'-(3-(methoxymethoxy)phenyl)-1',3'-dihydropyro[cyclopropane-1,2'-indene]-1'-yl)carbamate. Claim 25 In claim 1, a compound selected from the group consisting of the following compounds or a pharmaceutically acceptable salt thereof: (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate; (S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate; and (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate. Claim 26 (S)-quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate. Claim 27 (S)-quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate. Claim 28 (S)-quinuclidin-3-yl (2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-indene-1-yl)carbamate. Claim 29 (S)-quinuclidin-3-yl (5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate. Claim 30 (S)-quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridin-3-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-1-yl)carbamate. Claim 31 A pharmaceutical composition for the prevention or treatment of Gaucher disease, Fabry disease, Tay-Sachs disease or Parkinson's disease comprising, as an active ingredient, a compound according to any one of claims 1 to 20 and claims 24 to 30 or a pharmaceutically acceptable salt thereof.

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