Novel derivatives having a 2,3-dihydro-1H-indene group or a 2,3-dihydrobenzofuran group, or pharmaceutically acceptable salts thereof, and pharmaceutical compositions containing the same.

Abstract

To provide a compound having an inhibitory activity against glucosylceramide synthase, a method for producing the same, a pharmaceutical composition containing the same, and uses thereof.SOLUTION: A novel compound having a 2,3-dihydro-1H-indene or 2,3-dihydrobenzofuran moiety represented by the following <chemical formula 1a> or pharmaceutically acceptable salt thereof has an inhibitory activity against glucosylceramide synthase (GCS), and therefore can be usefully applied for preventing or treating various diseases associated with GCS, such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease.SELECTED DRAWING: None

Description

[Technical 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 group or a 2,3-dihydrobenzofuran group, or pharmaceutically acceptable salts thereof, methods for producing the same, pharmaceutical compositions containing the same, and uses thereof. [Background technology]

[0002] Lysosomal storage disorders (LSDs) are metabolic disorders caused by a genetic deficiency or lack of specific enzymes within lysosomes. Because LSDs involve the accumulation of unmetabolized or undegraded substrates, they manifest as a variety of pathological symptoms throughout the body. Currently, approximately 50 types of LSDs are known, and they are broadly classified into diseases such as mucopolysaccaridosis, oligosaccharidosis, and sphingolipidosis, depending on the substances that accumulate.

[0003] Among diseases, sphingolipidosis, a type of glucose-lipid storage disorder related to sphingolipid metabolism, exhibits symptoms due to the accumulation of various membrane sphingoglycolipids (GSLs) such as glucosylceramide and trihexosylceramide. For example, if enzymes related to sphingolipid metabolism, such as beta-glucosidase and alpha-galactosidase, do not have normal activity, their substrates (e.g., glucosylceramide, trihexosylceramide, etc.) accumulate, leading to the appearance of various symptoms such as Gaucher disease and Fabry disease.

[0004] Two types of treatments are known for LSD. The first method involves replacing or supplementing insufficient or deficient metabolic enzymes. While such enzyme replacement therapy (ERT) is safe and effective, it requires regular intravenous administration of the relevant enzymes; the dosage must be adjusted according to the enzymatic reaction; and the cost is relatively high. In particular, ERT is not sufficiently effective in treating symptoms related to the nervous system because it is difficult to deliver the enzymes to the nervous system. Furthermore, there is the problem of frequent production of autoantibodies against the administered enzymes.

[0005] The second method is substrate reduction therapy (SRT) to inhibit the synthesis of accumulating substrates. Glucosylceramide synthase (GCS) (also known as "UDP-glucose:ceramide glycosyltransferase," "UDP-glucose:N-acylsphingosine D-glucosyltransferase," or "EC2.4.1.80"), an enzyme involved in sphingolipid metabolism, participates in the reaction of ceramide and glucose to produce glucosylceramide. The resulting glucosylceramide is converted into various GSLs. Glucosylceramide synthase (GCS) inhibitors inhibit the activity of GCS, thereby reducing the production of glucosylceramide in the body and preventing the abnormal accumulation of glycolipids (trihexosylceramide, GM1, GM2, etc.) in cells and organs.

[0006] Thus, GCS inhibitors inhibit GCS activity and prevent the accumulation of glycolipids, making them useful in treating lysosomal storage disorders, particularly GM1 gangliosidosis, Tay-Sachs disease, Sandhoff disease, Gaucher disease, Fabry disease, Niemann-Pick disease (types A and B), metachromatic leukodystrophy, and Krabbe disease, which are all impaired glycolipid storage. GCS inhibitors can also be used to treat secondary diseases associated with glycolipid storage, such as Niemann-Pick disease (type C), mucopolysaccharides, and type IV mucolipidosis (see Chen CS, et al., Abnormal transport along the lysosomal pathway in mucolipidosis, type IV disease Proc Natl Acad Sci US A. 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). Furthermore, it has been reported to be useful in the treatment of diseases associated with the accumulation of glycolipids, such as renal hypertrophy (e.g., diabetic nephropathy); hyperglycemia or hyperinsulinemia; cancers with abnormal glycolipid synthesis; infections caused by organisms that use cell surface glycolipids as receptors; infections in which glucosylceramide synthesis is essential or important; diseases in which excessive glycolipid synthesis occurs (e.g., atherosclerosis, polycystic kidney disease, and renal hypertrophy); neuropathy and / or injury associated with macrophage recruitment and activation (e.g., Alzheimer's disease, epilepsy, stroke, spinal cord disease, Parkinson's disease, etc.); inflammatory diseases or disorders (e.g., rheumatoid arthritis, Crohn's disease, asthma, sepsis); and diabetes and obesity (see WO2006 / 053043).Furthermore, overexpression of GCS inhibits ceramide-induced apoptosis (see 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 may be useful in treating proliferative diseases such as cancer by inducing apoptosis in diseased cells.

[0007] Various studies have been conducted to develop GCS inhibitors. For example, various compounds exhibiting inhibitory activity against GCS are disclosed in WO2005 / 068426, WO2006 / 053043, WO2008 / 150486, WO2009 / 117150, WO2010 / 014554, WO2014 / 043068, etc. [Overview of the Initiative] [Problems that the invention aims to solve]

[0008] The inventors have found that derivatives having a 5,6-condensed bicyclic group, namely a 2,3-dihydro-1H-indene group or a 2,3-dihydrobenzofuran group, or pharmaceutically acceptable salts thereof, exhibit excellent inhibitory activity against glucosylceramide synthase (GCS). Therefore, the derivatives having a 2,3-dihydro-1H-indene group or a 2,3-dihydrobenzofuran group, or pharmaceutically acceptable salts thereof, can be usefully applied to prevent or treat various GCS-related diseases such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease.

[0009] Accordingly, the present invention provides derivatives having a 2,3-dihydro-1H-indene group or a 2,3-dihydrobenzofuran group, pharmaceutically acceptable salts thereof, methods for producing the same, pharmaceutical compositions containing the same, and uses thereof. [Means for solving the problem]

[0010] One embodiment of the present invention provides a derivative having a 2,3-dihydro-1H-indene group or a 2,3-dihydrobenzofuran group, or a pharmaceutically acceptable salt thereof.

[0011] Another embodiment of the present invention provides a method for producing a derivative having the 2,3-dihydro-1H-indene group or the 2,3-dihydrobenzofuran group or a pharmaceutically acceptable salt thereof.

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

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

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

[0015] The present invention has revealed that derivatives having a 5,6-condensed bicyclic group, i.e., a 2,3-dihydro-1H-indene group or a 2,3-dihydrobenzofuran group, or pharmaceutically acceptable salts thereof, exhibit excellent inhibitory activity against glucosylceramide synthase (GCS). Therefore, the compounds according to the present invention or pharmaceutically acceptable salts thereof can be usefully applied to prevent or treat various GCS-related diseases, such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease. [Modes for carrying out the invention]

[0016] In this specification, the term "alkyl" means a linear or branched aliphatic hydrocarbon group. For example, C1-C6 alkyl refers to linear or branched aliphatic hydrocarbons having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, and isopentyl.

[0017] The term "hydroxyl" refers to the "-OH" group. The term "alkoxy" refers to a group formed by substituting a hydrogen atom of a hydroxyl group with an alkyl group. For example, C1-C6 alkoxys include methoxy, ethoxy, propoxy, n-butoxy, n-pentyloxy, isopropoxy, sec-butoxy, tert-butoxy, neopentyloxy, and isopentyloxy.

[0018] The term "halogen" refers to a fluoro group, bromo group, chloro group, or iodine group.

[0019] The term "cycloalkyl" refers to a saturated aliphatic ring with 3 to 10 members, preferably 3 to 7 members, unless otherwise specified. Typical cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0020] The term "aryl" refers to an organic group derived from an aromatic hydrocarbon, obtained by removing one hydrogen atom from an aromatic hydrocarbon. This includes monocyclic or polycyclic condensed systems such as substituted or unsubstituted rings with 5 to 14 members, and forms in which multiple aryls are linked by single bonds. Examples of "aryls" include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perilenyl, crisenyl, naphthacenyl, and fluoranthenyl.

[0021] The term "heteroaryl" refers to a 5-12 member aromatic group having 1-3 heteroatoms selected from the group consisting of nitrogen (N), oxygen (O), and sulfur (S), and includes 5 or 6 member monocyclic heteroaryl groups and bicyclic heteroaryl groups formed by the condensation of a 5 or 6 member monocyclic heteroaryl group with a benzene ring or pyridine ring. The term "heterocyclic" refers to a 3-12 member monocyclic or polycyclic ring having one or more, preferably 1-4, identical or different heteroatoms selected from the group consisting of oxygen (O), nitrogen (N), and sulfur (S), but excluding aromatic rings. Non-limiting examples of heteroaryl or heterocyclic compounds include oxetane, pyrrolidine, pyrrole, tetrahydrofuran, furan, tetrahydrothiophene, thiophene, imidazolidine, imidazole, pyrazolidine, pyrazole, pyrrolidine, oxazolidine, oxazole, isoxazolidine, isoxazole, thiazolidine, thiazol, isothiazolidine, isothiazol, dioxolane, dithiolan, oxadiazole, thiadiazole, dithiazol, tetrazole, oxatetrazole, thiatetrazole, piperidine, pyridine, pyrimidine, tetrahydropyran, pyran, thian, thiopyran, piperazine, diazine, morpho This includes, but is not limited to, phosphorus, oxazine, dioxane, indole, indoline, benzodioxol, benzothiophene, benzofuran, benzimidazole, benzoxazole, benzisoxazole, benzothiazole, benzothiadiazole, benzotriazole, quinoline, isoquinoline, purine, phlopyridine, mono- or di-azabicycle (e.g., quinuclidine, diazabicycloheptane, monoazabicyclooctane, diazaspirondecane, etc.), hexahydropyrrolopyrrole, pyrrolopyrrole, pyrrolopyridine, imidazopyridazine, dihydrobenzodioxin, dihydrobenzofuran, etc.

[0022] The term "amino" refers to the "-NH2" group. The term "alkylamino" refers to an amino group that is substituted with a mono- or di-alkyl group. For example, C1-C6 alkylamino groups include amino groups that are substituted with a mono- or di-C1-C6 alkyl group.

[0023] The term "alkylthio" refers to the "-SR" group where R is alkyl. The term "cyano" refers to the "-CN" group.

[0024] The present invention relates to derivatives having a 5,6-condensed bicyclic group, i.e., a 2,3-dihydro-1H-indene group or a 2,3-dihydrobenzofuran group, or a pharmaceutically acceptable salt thereof, i.e., Chemical Formula 1: [ka]

[0025] (In the formula, L is -O-, -CO-, -CR1R2-, or -NR3-, Y and Z are independently -CR1R2-;-NR3-;-O-; or -S-, R1 and R2 are independently hydrogen; halogen; C1-C6 alkyl; C1-C6 alkyl having a nitrogen atom, oxygen atom, or sulfur atom; C3-C 10 Cycloalkyl; a 3-12 membered heterocyclic group; or a C1-C6 alkoxy, or R1 and R2 together with the carbon atom to which they are bonded, C3-C 10 Forming a cycloalkyl group, R3 is hydrogen; C1-C6 alkyl; C1-C6 alkyl having a nitrogen atom, oxygen atom, or sulfur atom; C3-C 10 Cycloalkyl; 3-12 membered heterocyclic group; or C1-C6 alkoxy, X is hydrogen; halogen; C1-C6 alkyl; C1-C6 alkyl substituted with 1-3 halogens; C1-C6 alkyl having a nitrogen atom, oxygen atom, or sulfur atom; C1-C6 alkoxy; or C1-C6 alkoxy substituted with 1-3 halogens. W is a bond, -CH2-, -O-, -NH-, -CH2CH2-, -CH=CH-, or -C≡C-. Ring A consists of 6-12 member aryls; 5-12 member heteroaryls; and C3-C3 rings. 10Cycloalkyl; or a 3-12 membered heterocyclic group, X1, X2, X3, and X4 are independently hydrogen; cyano; halogen; C1-C6 alkyl; C1-C6 alkoxy-C1-C6 alkyl; C1-C6 alkyl substituted with 1-3 halogens; C3-C 10 Cycloalkyl; 3-12 membered heterocyclic group; C1-C6 alkoxy; C1-C6 alkoxy substituted with 1-3 halogens; C1-C6 alkoxy-C1-C6 alkoxy; Morpholinyl-C1-C6 alkoxy; Mono- or di-C1-C6 alkylamino-C1-C6 alkoxy; C3-C 10 (Cycloalkyl-C1~C6 alkoxy; C1~C6 alkylthio; amino; mono- or di-C1~C6 alkylamino; C1~C6 alkylcarbonyl; hydroxy; or nitro) The present invention provides a compound represented by or a pharmaceutically acceptable salt thereof.

[0026] In the compound of chemical formula 1 or a pharmaceutically acceptable salt thereof according to the present invention, L may be -O-.

[0027] In the compound of chemical formula 1 or a pharmaceutically acceptable salt thereof according to the present invention, Y and Z may each be independently -O- or -CR1R2-.

[0028] In the compound of chemical formula 1 or a pharmaceutically acceptable salt thereof according to the present invention, R1 and R2 are each independently hydrogen or a C1-C6 alkyl group, or R1 and R2 together with the carbon atom to which they are bonded are C3-C6 10 A cycloalkyl group may be formed. In one embodiment, Y may be -O- and Z may be -CR1R2-.

[0029] In the compound of chemical formula 1 or a pharmaceutically acceptable salt thereof according to the present invention, X may be hydrogen, a halogen, or a C1-C6 alkoxy.

[0030] In the compound of Chemical Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, W may be a bond (i.e., the A ring is directly bonded to a 2,3-dihydro-1H-indenyl group or a 2,3-dihydrobenzofuranyl group) or -CH=CH-.

[0031] In the compound of Chemical Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, the A ring may be a 6- to 12-membered aryl; a 5- to 12-membered heteroaryl; or a 3- to 12-membered heterocyclic group. 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, pyridinyl, thienyl, quinolinyl, isoquinolinyl, benzofuranyl, benzo[b]thienyl, quinoxalinyl, or furanyl. In yet another embodiment, the 3- to 12-membered heterocyclic group may be 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.

[0032] In the compound of Chemical Formula 1 according to the present invention or a pharmaceutically acceptable salt thereof, X1, X2, X3, and X4 are each 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; morpholinyl; C1-C6 alkoxy; C1-C6 alkoxy substituted with 1 to 3 halogens; C1-C6 alkoxy-C1-C6 alkoxy; morpholinyl-C1-C6 alkoxy; mono- or di-C1-C6 alkylamino-C1-C6 alkoxy; C3-C 10 cycloalkyl-C1-C6 alkoxy; C1-C6 alkylthio; mono- or di-C1-C6 alkylamino; or C1-C6 alkylcarbonyl.

[0033] In a preferred embodiment of the present invention, L is -O-, Y and Z are independently -O- or -CR1R2-, R1 and R2 are either 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, X is hydrogen, a halogen, or a C1-C6 alkoxy. W is a bond or -CH=CH-, The A ring is a 6-12 membered aryl group; a 5-12 membered heteroaryl group; or a 3-12 membered heterocyclic group. X1, X2, X3, and X4 are independently hydrogen; cyano; halogen; C1-C6 alkyl; C1-C6 alkoxy-C1-C6 alkyl; C1-C6 alkyl substituted with 1-3 halogens; C3-C 10 Cycloalkyl; Morpholinyl; C1-C6 alkoxy; C1-C6 alkoxy substituted with 1-3 halogens; C1-C6 alkoxy-C1-C6 alkoxy; Morpholinyl-C1-C6 alkoxy; Mono- or di-C1-C6 alkylamino-C1-C6 alkoxy; C3-C 10 These are cycloalkyl-C1~C6 alkoxy; C1~C6 alkylthio; mono- or di-C1~C6 alkylamino; or C1~C6 alkylcarbonyl.

[0034] In the above embodiment, Y may be -O- and Z may be -CR1R2-.

[0035] In the above embodiment, ring A may be phenyl, naphthalenyl, or biphenyl.

[0036] In the above embodiment, the A ring may be benzodioxolyl, pyridinyl, thienyl, quinolinyl, isoquinolinyl, benzofuranyl, benzo[b]thienyl, quinoxalinyl, or furanyl.

[0037] In the above embodiment, the A ring may be 2,3-dihydrobenzodioxynyl, 2,3-dihydrobenzofuranyl, 3,4-dihydro-2H-benzo[b][1,4]oxazinyl, chromanil, or 3,4-dihydro-2H-benzo[b][1,4]dioxepinyl.

[0038] In compounds of chemical formula 1 or pharmaceutically acceptable salts thereof, preferred compounds include compounds selected from the group consisting of the following (including pharmaceutically acceptable salts thereof): (S)-Quinuclidin-3-yl (5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(p-tolyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(p-tolyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,5-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,4-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3,5-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(p-tolyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(p-tolyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-(methylthio)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,3-dihydrobenzofuran-5-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-(2-morpholinoethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-(2,2,2-trifluoroethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-(2-morpholinoethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethyl)pyridine-4-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-dichloropyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,3-dichloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(dimethylamino)-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(chroman-6-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-Methoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(thiophen-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-methylthiophen-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(2-(dimethylamino)ethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(isoquinoline-8-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(Isoquinoline-5-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(isoquinoline-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(tert-butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-morpholinophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(methoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(2,2-difluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-methyl-4-morpholinophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-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-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-8-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(benzofuran-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(benzofuran-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-dichloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-difluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-5-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-methoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(tert-butoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,6-dimethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(benzo[b]thiophen-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-(tert-butoxy)pyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (5-(6-methoxy-5-(trifluoromethyl)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (5-(6-methoxynaphthalene-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-([1,1'-biphenyl]-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(quinoxaline-6-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(Fran-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(6-isopropoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-ethoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-methoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-butoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butoxy-3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-dipropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-fluoro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-chloro-2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-6-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-chloro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (5-(3-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,4-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-isopropyl-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(5-methylfuran-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(benzo[b]thiophen-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-5-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-cyano-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-ethoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-methyl-4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(3-(methylthio)-5-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-4-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-ethoxy-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-methoxy-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-ethoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluoro-5-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(6-ethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-ethoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-isopropoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(6-propoxypyridine-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(6-butoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (5-(6-(2-methoxyethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(6-isobutoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-dimethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-acetylthiophen-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-((E)-3-fluorostyryl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-((E)-4-ethylstyryl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-((E)-2-cyclohexylvinyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-ethylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(tert-butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butylphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-isopropylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-isopropoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-isobutylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(3-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(3-isopropoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(3-ethylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(3-isopropylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(thiophen-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(furan-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridin-3-yl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (2,2-diethyl-5-(2-fluoro-4-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-Methoxy-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(tert-butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-Methoxy-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-Methoxy-5-(4-Methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-Methoxy-5-(2-Methoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl (6-Methoxy-5-(3-Methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-Methoxy-2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-isobutoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-(tert-butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(6-(cyclopropylmethoxy)pyridin-3-yl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(2-methoxypyridin-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(4-fluorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(4-chlorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(4-(trifluoromethyl)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(4-(trifluoromethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-inden]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(3-chlorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(3-(trifluoromethyl)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(4-(2-methoxyethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-inden]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(3-(2-methoxyethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-inden]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(4-(methoxymethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5'-(3-(methoxymethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate; (S)-Quinuclidin-3-yl (5-(3-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (5-(2-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (3,3-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (3,3-dimethyl-5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (3,3-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate; (S)-Quinuclidine-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)-Quinuclidine-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate; and (S)-Quinuclidine-3-yl (6-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate.

[0039] Compounds of chemical formula 1 or their pharmaceutically acceptable salts may be in the form of cis- or trans-geometric isomers. Unless otherwise specified, compounds of chemical formula 1 or their pharmaceutically acceptable salts may include both cis- and trans-geometric isomers. Furthermore, compounds of chemical formula 1 or their pharmaceutically acceptable salts may have substituents containing chiral atoms. Thus, they may be in the form of racemic mixtures (RS) or optical isomers such as (R) or (S) isomers. Unless otherwise specified, compounds of chemical formula 1 or their pharmaceutically acceptable salts may include both racemic mixtures (RS) and each optical isomer such as the (R) or (S) isomer. In addition, compounds of chemical formula 1 or their pharmaceutically acceptable salts may have two or more chiral centers. Thus, they may be in the form of one or more diastereomers or mixtures thereof. Unless otherwise specified, compounds of chemical formula 1 or their pharmaceutically acceptable salts may include both each diastereomer and mixtures thereof.

[0040] The compound of Chemical Formula 1 of the present invention may be in the form of a pharmaceutically acceptable salt. The salt may be in the form of a conventional acid addition salt, and may include salts derived from inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid, or hydrobromic 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, gentisic acid, fumaric acid, lactobionic acid, salicylic acid, phthalic acid, embonic acid, aspartic acid, glutamic acid, or acetylsalicylic acid. The salt may also include salts derived from amino acids such as glycine, alanine, valine, isoleucine, serine, cysteine, cystine, aspartic acid, glutamine, lysine, arginine, tyrosine, or proline. Furthermore, the salt includes, for example, salts derived from sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, or toluenesulfonic acid.

[0041] The compound of chemical formula 1 or a pharmaceutically acceptable salt thereof according to the present invention can be produced by various methods.

[0042] For example, as shown in Reaction Equation 1 below, the compound of Chemical Formula 1a or a pharmaceutically acceptable salt thereof according to the present invention can be produced by a manufacturing method comprising: reacting the compound of Chemical Formula 2 or a salt thereof with ethyl chloroformate to obtain the compound of Chemical Formula 3; coupling the compound of Chemical Formula 3 with the compound of Chemical Formula 4 to obtain the compound of Chemical Formula 5; reacting the compound of Chemical Formula 5 with AW-boronic acid substituted with X1, X2, X3, or X4 to obtain the compound of Chemical Formula 1a; and optionally, converting the compound of Chemical Formula 1a into a pharmaceutically acceptable salt thereof.

[0043] [ka]

[0044] In reaction equation 1, X, Y, Z, W, A ring, X1, X2, X3, and X4 are the same as those defined above.

[0045] The compound of chemical formula 2 may be a commercially available or known compound, or it may be synthesized according to the literature. The reaction of the compound of chemical formula 2 or a salt thereof with ethyl chloroformate may be carried out in the presence of an organic base such as triethylamine or N,N-diisopropylethylamine, or an inorganic base such as potassium carbonate. The base may be used in an amount ranging from 1 to 1.5 equivalents per equivalent of the compound of chemical formula 2, or in an amount ranging from 3 to 5 equivalents per equivalent of the salt (e.g., hydrochloride) of the compound of chemical formula 2. The reaction may be carried out in a solvent such as dichloromethane or tetrahydrofuran, preferably at 0°C to room temperature.

[0046] The coupling of the compound of chemical formula 3 and the compound of chemical formula 4 (i.e., quinuclidinol) may be carried out by a condensation reaction including the removal of ethanol. The reaction may preferably be carried out in the presence of a base such as sodium hydride. The reaction may also be carried out in a nonpolar organic solvent such as toluene at 120°C to 140°C.

[0047] The reaction of the compound of chemical formula 5 with AW-boronic acid substituted with X1, X2, X3, or X4 may be carried out according to the Suzuki reaction. The Suzuki reaction may be carried out using a palladium catalyst such as tetrakis(triphenylphosphine)palladium(O) (Pd(PPh3)4), palladium(II) acetate (Pd(OAc)2), or [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2). The Suzuki reaction may also be carried out in the presence of an inorganic base such as cesium carbonate (Cs2CO3), sodium carbonate (Na2CO3), potassium carbonate (K2CO3), or potassium phosphate (K3PO4). The Suzuki reaction may be carried out in a nonpolar organic solvent such as toluene or a polar organic solvent such as 1,4-dioxane, tetrahydrofuran, acetonitrile, 1,2-dimethoxyethane, or N,N-dimethylformamide at 50°C to 150°C, preferably 80°C to 120°C. Other reaction conditions, including reaction time, may be determined by known methods for the Suzuki reaction.

[0048] The conversion of the compound of chemical formula 1a to its pharmaceutically acceptable salt may be carried out according to conventional methods. For example, a pharmaceutically acceptable salt of the compound of chemical formula 1a may be prepared by dissolving the compound of chemical formula 1a in a water-miscible solvent such as methanol, ethanol, acetone, or 1,4-dioxane, and then crystallizing it by adding a free acid or free base.

[0049] Furthermore, the compound of chemical formula 1a or a pharmaceutically acceptable salt thereof according to the present invention can be produced by a manufacturing method that includes the steps of: reacting the compound of chemical formula 4 with bis(4-nitrophenyl) carbonate to obtain the compound of chemical formula 7, as shown in the reaction formula 2 below; reacting the compound of chemical formula 7 with the compound of chemical formula 2 to obtain the compound of chemical formula 5; reacting the compound of chemical formula 5 with AW-boronic acid substituted with X1, X2, X3, or X4 to obtain the compound of chemical formula 1a; and optionally converting the compound of chemical formula 1a into a pharmaceutically acceptable salt thereof.

[0050] [ka]

[0051] In reaction equation 2, X, Y, Z, W, the A ring, X1, X2, X3, and X4 are the same as those defined above.

[0052] The reaction between the compound of chemical formula 4 (i.e., quinuclidinol) and bis(4-nitrophenyl) carbonate may be carried out in a polar solvent such as N,N-dimethylformamide, preferably at 0°C to 25°C. Alternatively, the compound of chemical formula 7 may be produced by reacting the compound of chemical formula 4 with 4-nitrophenyl chloroformate in a solvent such as dichloromethane or acetonitrile, in the presence of a base such as triethylamine.

[0053] The reaction between the compound of chemical formula 7 and the compound of chemical formula 2 may be carried out at 0°C to 25°C in a solvent such as N,N-dimethylformamide, tetrahydrofuran, or acetonitrile, in the presence of a base such as N,N-diisopropylethylamine or triethylamine.

[0054] The reaction between the compound of chemical formula 5 and AW-boronic acid substituted with X1, X2, X3, or X4 may be carried out according to the Suzuki reaction as described above. Furthermore, the conversion of the compound of chemical formula 1a to its pharmaceutically acceptable salt may be carried out according to the usual method as described above.

[0055] Compounds having a 2,3-dihydro-1H-indene group or a 2,3-dihydrobenzofuran group according to the present invention, i.e., compounds of chemical formula 1 or pharmaceutically acceptable salts thereof, have excellent inhibitory activity against glucosylceramide synthase (GCS). Therefore, compounds of chemical formula 1 or pharmaceutically acceptable salts thereof can be usefully applied for the prevention or treatment of various diseases associated with GCS.

[0056] Accordingly, the present invention includes, within its scope, pharmaceutical compositions for inhibiting glucosylceramide synthase (GCS), comprising a therapeutically effective amount of the compound of chemical formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient. In one embodiment, the present invention provides a pharmaceutical composition for preventing or treating GCS-related diseases such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease, comprising a therapeutically effective amount of the compound of chemical formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.

[0057] The pharmaceutical composition of the present invention may contain pharmaceutically acceptable carriers such as diluents, disintegrants, sweeteners, lubricants, or flavoring agents. The pharmaceutical composition can be formulated into oral formulations such as tablets, capsules, powders, granules, suspensions, emulsions, or syrups; or into parenteral formulations such as topical solutions, topical suspensions, topical emulsions, gels (e.g., ointments), inhalants, sprays, or injections. These formulations may take various forms, for example, single-dose or repeated-dose dosage forms.

[0058] The pharmaceutical composition of the present invention may contain, for example, a diluent (e.g., lactose, corn starch, etc.); a lubricant (e.g., magnesium stearate, etc.); an emulsifier; a suspending agent; a stabilizer; and / or an isotonic agent. If necessary, the composition may further contain a sweetener and / or a flavoring agent.

[0059] The compositions of the present invention may be administered orally, or parenterally, including by routes of administration such as inhalation, intravenous, intraperitoneal, subcutaneous, rectal, and topical application. Accordingly, the compositions of the present invention can be formulated in various forms such as tablets, capsules, aqueous solutions, or suspensions. For oral tablets, carriers such as lactose and corn starch, and lubricants such as magnesium stearate are commonly used. For oral capsules, lactose and / or dried corn starch can be used as diluents. If an aqueous suspension for oral administration is required, emulsifiers and / or suspending agents can be incorporated into the active ingredient. Specific sweeteners and / or flavorings may be used as needed. For intramuscular, intraperitoneal, subcutaneous, and intravenous administration, it is usually necessary to prepare a sterile solution of the active ingredient and buffer it by appropriately adjusting the pH of the solution. For intravenous administration, it is necessary to adjust the total concentration of the solute to make the formulation isotonic. The compositions of the present invention can be in the form of an aqueous solution containing a pharmaceutically acceptable carrier, such as physiological saline with a pH of 7.4. This solution can be introduced into the patient's muscle bloodstream via local bolus injection.

[0060] The compound of chemical formula 1 or a pharmaceutically acceptable salt thereof can be administered to the patient in a therapeutically effective dose ranging from approximately 0.0001 mg / kg to approximately 100 mg / kg per day. Of course, the dose may be adjusted depending on the patient's age, weight, sensitivity, symptoms, or the activity of the compound.

[0061] Within its scope, the present invention includes a method for inhibiting glucosylceramide synthase (GCS) in mammals, comprising administering a therapeutically effective amount of a compound of chemical formula 1 or a pharmaceutically acceptable salt thereof to a mammal in need. In one embodiment, the present invention provides a method for treating GCS-related diseases such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease, comprising administering a therapeutically effective amount of a compound of chemical formula 1 or a pharmaceutically acceptable salt thereof to a mammal in need.

[0062] The present invention also provides the use of a compound of chemical formula 1 or a pharmaceutically acceptable salt thereof for producing a drug for inhibiting glucosylceramide synthase (GCS) in mammals. In one embodiment, the present invention provides the use of a compound of chemical formula 1 or a pharmaceutically acceptable salt thereof for producing a drug for preventing or treating GCS-related diseases such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease. [Examples]

[0063] The following examples and test examples are for illustrative purposes only and do not limit the scope of the present invention.

[0064] In the following examples, "brine" refers to a saturated sodium chloride solution. Unless otherwise specified, all temperatures are in degrees Celsius (°C). Unless otherwise specified, all reactions were carried out at room temperature.

[0065] The compounds prepared in the following manufacturing examples and examples were analyzed as follows: Nuclear magnetic resonance (NMR) spectroscopy was performed using a Bruker 400 MHz spectrometer, and chemical shifts (in ppm) were analyzed. Column chromatography was performed using silica gel (Merck, 70-230 mesh). Each starting material was a known compound, which was synthesized according to the literature or purchased commercially. All reaction and chromatographic fractions were analyzed by thin-layer chromatography (TLC) on 250 nm silica gel plates and visualized with ultraviolet or iodine (I2) staining.

[0066] Manufacturing Example 1: (S)-Quinuclidine-3-yl (5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate Step 1: Ethyl (5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate 5-Bromo-2,3-dihydro-1H-iddene-1-amine (2 g, 9.4 mmol) was dissolved in dichloromethane (50 ml), and then triethylamine (1.45 ml, 10.4 mmol) and ethyl chloroformate (1 ml, 10.4 mmol) were gradually added. The reaction mixture was stirred at room temperature for 4 hours. After adding water to the reaction mixture, it was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting pale yellow oily residue (2.6 g) was used in the next reaction without further purification.

[0067] Step 2: (S)-Quinuclidine-3-yl (5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate (S)-(+)-3-quinuclidinol (3.5 g, 27.5 mmol) was dissolved in toluene (80 ml), and then sodium hydride (219.6 mg, 9.2 mmol) was added at 0°C. After stirring the reaction mixture for 15 minutes, ethyl (5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate (2.6 g, 9.2 mmol) prepared in step 1 was added. The reaction mixture was stirred under reflux at 140°C for 21 hours, and then cooled to room temperature. Salt water was added to the reaction mixture, and then extracted with ethyl acetate. The organic layer was washed twice with salt water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate / (methanol / aqueous ammonia = 1 / 1) = 9 / 1, v / v) to obtain the title compound as a white solid (1.3 g, yield: 46%). 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)

[0068] Manufacturing Example 2: (S)-Quinuclidine-3-yl (6-bromo-2,3-dihydro-1H-inden-1-yl)carbamate The title compound was prepared using 6-bromo-2,3-dihydro-1H-idden-1-amine as a starting material, following the same procedure as in Preparation Example 1. 1 H-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)

[0069] Manufacturing Example 3: (S)-Quinuclidin-3-yl (6-bromo-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate The title compound was prepared using 6-bromo-2,2-dimethyl-2,3-dihydro-1H-idden-1-amine as a starting material, following the same procedure as in Preparation Example 1. 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)

[0070] Manufacturing Example 4: (S)-Quinuclidin-3-yl (5-bromo-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate Step 1: 5-bromo-2,2-dimethyl-2,3-dihydro-1H-idden-1-amine hydrochloride 5-Bromo-2,2-dimethyl-2,3-dihydro-1H-inden-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 borohydride cyanohydride (157.7 g, 2509.3 mmol) were gradually added at room temperature. The reaction mixture was stirred at room temperature for 4 hours, then refluxed at 80°C for 22 hours. The reaction mixture was cooled to room temperature, basicized to pH > 12 with 1N sodium hydroxide solution, and then extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. Ethyl acetate was added to the resulting residue, and then hydrochloric acid solution (4M) in 1,4-dioxane was added. 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 obtain the title compound as a white solid. (100 g, yield: 86.5%) 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)

[0071] Step 2: (S)-Quinuclidin-3-yl (5-bromo-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate A solution of (S)-(+)-3-quinuclidinol (38.6 g, 303.7 mmol) and bis(4-nitrophenyl) carbonate (92.4 g, 303.7 mmol) in N,N-dimethylformamide (700 ml) was stirred at room temperature for 8 hours. 5-bromo-2,2-dimethyl-2,3-dihydro-1H-idene-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 stirred overnight at room temperature. The reaction mixture was diluted with water (500 ml), acidified to pH 1-2 with 1N hydrochloric acid aqueous solution, and then extracted with diisopropyl ether (300 ml × 2). The aqueous layer was basicized to pH 12 with ammonia and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was dissolved in isopropyl acetate, and then heptane was added. The mixture was stirred overnight at room temperature. The resulting solid was filtered under reduced pressure, washed with heptane, and dried to obtain the title compound in the form of a white solid. (56 g, yield: 56.3%) 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)

[0072] Manufacturing Example 5: (S)-Quinuclidin-3-yl (5-bromo-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate Step 1: 5-Bromo-2,2-diethyl-2,3-dihydro-1H-inden-1-one 5-Bromo-1-indanone (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. The reaction mixture was stirred for 15 minutes, and then iodoethane (19.1 ml, 236.9 mmol) was gradually added at the same temperature. The reaction mixture was stirred overnight at room temperature. After adding water to the reaction mixture, it was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (n-hexane / ethyl acetate = 10 / 1, v / v) to obtain the title compound as a white solid (17 g, yield: 67%). 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)

[0073] Step 2: 5-Bromo-2,2-diethyl-2,3-dihydro-1H-indene-1-amine hydrochloride Using 5-bromo-2,2-diethyl-2,3-dihydro-1H-inden-1-one prepared in Step 1, the title compound was prepared following the same procedure as in Step 1 of Preparation Example 4. 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)

[0074] Step 3: (S)-Quinuclidine-3-yl (5-bromo-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate Using the 5-bromo-2,2-diethyl-2,3-dihydro-1H-idden-1-amine hydrochloride prepared in Step 2, the title compound was prepared following the same procedure as in Step 2 of Preparation Example 4. 1H-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), 2.8~2.70(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)

[0075] Manufacturing Example 6: (S)-Quinuclidine-3-yl (5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate Step 1: 5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one 5-Bromo-6-methoxy-2,3-dihydro-1H-inden-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. The reaction mixture was stirred for 15 minutes, and then iodomethane (10.9 ml, 174.6 mmol) was gradually added at the same temperature. The reaction mixture was stirred overnight at room temperature. After adding water to the reaction mixture, it was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (n-hexane / ethyl acetate = 10 / 1, v / v) to obtain the title compound as a white solid (10 g, yield: 89%). 1 H-NMR (400MHz, CDCl3) δ 7.66(s, 1H), 7.21(s, 1H), 3.94(s, 3H), 2.93(s, 2H), 1.24(s, 6H)

[0076] Step 2: 5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-idene-1-amine hydrochloride Using the 5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one prepared in Step 1, the title compound was prepared following the same procedure as in Step 1 of Preparation Example 4. 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)

[0077] Step 3: (S)-Quinuclidine-3-yl (5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate Using the 5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-idden-1-amine hydrochloride prepared in Step 2, the title compound was prepared following the same procedure as in Step 2 of Preparation Example 4. 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)

[0078] Manufacturing Example 7: (S)-Quinuclidin-3-yl (5-bromo-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate The title compound was prepared using 5-bromo-6-fluoro-2,3-dihydro-1H-inden-1-one as a starting material, following the same procedure as in Preparation Example 6. 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)

[0079] Manufacturing Example 8: (S)-Quinuclidin-3-yl (5'-bromo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate Step 1: 5'-bromospiro[cyclopropane-1,2'-indene]-1'(3'H)-one 5-Bromo-1-indanone (5 g, 23.7 mmol) was dissolved in N,N-dimethylformamide (100 ml), and then 60% sodium hydride (2.7 g, 35.5 mmol) was added at 0°C. The reaction mixture was stirred for 15 minutes, and then 1,2-dibromomethane (5.1 ml, 35.5 mmol) was gradually added at the same temperature. The reaction mixture was stirred overnight at room temperature. After adding water to the reaction mixture, it was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (n-hexane / ethyl acetate = 10 / 1, v / v) to obtain the title compound as a white solid (3.5 g, yield: 62%). 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)

[0080] Step 2: 5'-bromo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-amine hydrochloride Using the 5'-bromospiro[cyclopropane-1,2'-indene]-1'(3'H)-one prepared in Step 1, the title compound was prepared following the same procedure as in Step 1 of Preparation Example 4. 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)

[0081] Step 3: (S)-Quinuclidin-3-yl (5'-bromo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate Using the 5'-bromo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-amine hydrochloride prepared in Step 2, the title compound was prepared following the same procedure as in Preparation Example 1. 1 H-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)

[0082] Manufacturing Example 9: (S)-Quinuclidin-3-yl (5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate Step 1: 6-bromo-1,1-dimethyl-2,3-dihydro-1H-idene A 1.0 M solution of titanium(IV) chloride in 28.4 ml of dichloromethane was gradually added to 20 ml of dichloromethane at -30°C under a nitrogen atmosphere. A 2.0 M solution of zinc dimethylate in 16.6 ml of toluene was gradually added to the mixture at the same temperature, and the mixture was stirred for 30 minutes. A 2 g, 9.5 mmol solution of 6-bromo-2,3-dihydro-1H-inden-1-one in 10 ml of dichloromethane was gradually added to the reaction mixture, and the mixture was stirred at -10°C for 4 hours. The reaction was quenched by adding ice water to the reaction mixture, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 5 / 1, v / v) to obtain the title compound as a white solid (2.1 g, yield: 99%). 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)

[0083] Step 2: 5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one 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 gradually added. Potassium permanganate (4 g, 25.3 mmol) was gradually added to the reaction mixture, and the mixture was stirred under reflux for 5 hours. After the reaction mixture was cooled to room temperature, it was filtered and concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 5 / 1, v / v) to obtain the title compound as a white solid (1.85 g, yield: 92%). 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)

[0084] Step 3: 5-bromo-3,3-dimethyl-2,3-dihydro-1H-idden-1-amine hydrochloride Using the 5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one prepared in Step 2, the title compound was prepared following the same procedure as in Step 1 of Preparation Example 4. The product was used in the next reaction without further purification.

[0085] Step 4: Ethyl (5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate The title compound was prepared using 5-bromo-3,3-dimethyl-2,3-dihydro-1H-idden-1-amine hydrochloride prepared in Step 3, following the same procedure as in Step 1 of Preparation Example 1. 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)

[0086] Step 5: (S)-Quinuclidin-3-yl (5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate Using the ethyl (5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate prepared in step 4, the title compound was prepared following the same procedure as in step 2 of preparation example 1. 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)

[0087] Manufacturing Example 10: (S)-Quinuclidine-3-yl (6-bromo-2,3-dihydrobenzofuran-3-yl)carbamate The title compound was prepared using 6-bromo-2,3-dihydrobenzofuran-3-amine as a starting material, following the same procedure as in Preparation Example 1. 1H-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)

[0088] Manufacturing Example 11: (S)-Quinuclidin-3-yl (5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate Step 1: 5-Bromo-2,2-dimethylbenzofuran-3(2H)-one 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. The reaction mixture was stirred for 15 minutes, and then iodomethane (9.15 g, 64.5 mmol) was gradually added at the same temperature. The reaction mixture was stirred overnight at room temperature. After adding water to the reaction mixture, it was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (n-hexane / ethyl acetate = 10 / 1, v / v) to obtain the title compound as a white solid (2.5 g, yield: 80%). 1 H-NMR (400MHz, CDCl3) δ 7.81(s, 1H), 7.79(d, 1H), 6.98(d, 1H), 1.47(s, 6H)

[0089] Step 2: 5-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-amine Using the 5-bromo-2,2-dimethylbenzofuran-3(2H)-one prepared in Step 1, the title compound was prepared following the same procedure as in Step 1 of Preparation Example 4. 1H-NMR (400MHz, CDCl3) δ 7.40(s, 1H), 7.27(d, 1H), 6.63(d, 1H), 4.12(s, 1H), 1.41(d, 6H)

[0090] Step 3: (S)-Quinuclidin-3-yl (5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate Using the 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-amine prepared in Step 2, the title compound was prepared following the same procedure as in Preparation Example 1. 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)

[0091] Manufacturing Example 12: (S)-Quinuclidin-3-yl (6-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate Step 1: 6-bromo-2,2-dimethylbenzofuran-3(2H)-one The title compound was prepared using 6-bromobenzofuran-3(2H)-one as a starting material, following a procedure similar to that of step 1 in Production Example 11. 1 H-NMR (400MHz, CDCl3) δ 7.53(d, 1H), 7.30~7.27(m, 1H), 7.21(dd, 1H), 1.47(s, 6H)

[0092] Step 2: (S)-Quinuclidin-3-yl (6-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate Using the 6-bromo-2,2-dimethylbenzofuran-3(2H)-one prepared in Step 1, the title compound was prepared following the same procedure as in Preparation Example 4. 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)

[0093] Example 1: (S)-Quinuclidin-3-yl (5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate To a mixture of (S)-quinuclidin-3-yl (5-bromo-2,3-dihydro-1H-inden-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 Preparation Example 1, 1,4-dioxane (1 ml) and water (0.5 ml) were gradually added. The reaction mixture was stirred under reflux at 120°C overnight and then cooled to room temperature. After adding water to the reaction mixture, it was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate / (methanol / aqueous ammonia = 1 / 1) = 9 / 1, v / v) to obtain the title compound as a white solid. (19 mg, yield: 64%) 1H-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)

[0094] Examples 2-24 The title compounds of Examples 2-24 were prepared using the (S)-quinuclidin-3-yl (5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate prepared in Preparation Example 1, and the corresponding substituted phenylboronic acid, respectively, following the same procedure as in Example 1.

[0095] Example 2: (S)-Quinuclidin-3-yl (5-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0096] Example 3: (S)-Quinuclidine-3-yl (5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0097] Example 4: (S)-Quinuclidine-3-yl (5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.0 5(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)

[0098] Example 5: (S)-Quinuclidine-3-yl (5-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 2.9 4(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)

[0099] Example 6: (S)-Quinuclidin-3-yl (5-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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), 3.0 4(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)

[0100] Example 7: (S)-Quinuclidine-3-yl (5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0101] Example 8: (S)-Quinuclidine-3-yl (5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0102] Example 9: (S)-Quinuclidine-3-yl (5-(2-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0103] Example 10: (S)-Quinuclidin-3-yl (5-(2-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0104] Example 11: (S)-Quinuclidine-3-yl (5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0105] Example 12: (S)-Quinuclidine-3-yl (5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0106] Example 13: (S)-Quinuclidine-3-yl (5-(p-tolyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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), 2.9 6~2.67(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)

[0107] Example 14: (S)-Quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0108] Example 15: (S)-Quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0109] Example 16: (S)-Quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0110] Example 17: (S)-Quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0111] Example 18: (S)-Quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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), 3.0 3(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)

[0112] Example 19: (S)-Quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0113] Example 20: (S)-Quinuclidin-3-yl (5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 3.0 3(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)

[0114] Example 21: (S)-Quinuclidin-3-yl (5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0115] Example 22: (S)-Quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0116] Example 23: (S)-Quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0117] Example 24: (S)-Quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0118] Examples 25-48 The title compounds of Examples 25-48 were prepared using the (S)-quinuclidin-3-yl (6-bromo-2,3-dihydro-1H-inden-1-yl)carbamate prepared in Preparation Example 2, and the corresponding substituted phenylboronic acid, respectively, following the same procedure as in Example 1.

[0119] Example 25: (S)-Quinuclidin-3-yl (6-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0120] Example 26: (S)-Quinuclidin-3-yl (6-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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), 3.0 0(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)

[0121] Example 27: (S)-Quinuclidin-3-yl (6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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, 1 H), 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)

[0122] Example 28: (S)-Quinuclidine-3-yl (6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 3.0 9(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)

[0123] Example 29: (S)-Quinuclidin-3-yl (6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0124] Example 30: (S)-Quinuclidin-3-yl (6-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0125] Example 31: (S)-Quinuclidine-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0126] Example 32: (S)-Quinuclidine-3-yl (6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0127] Example 33: (S)-Quinuclidine-3-yl (6-(2-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0128] Example 34: (S)-Quinuclidin-3-yl (6-(2-chlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0129] Example 35: (S)-Quinuclidine-3-yl (6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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, 1) H), 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)

[0130] Example 36: (S)-Quinuclidine-3-yl (6-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0131] Example 37: (S)-Quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.2 8(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)

[0132] Example 38: (S)-Quinuclidine-3-yl (6-(p-tolyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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, 1) H), 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)

[0133] Example 39: (S)-Quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0134] Example 40: (S)-Quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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, 1) H), 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)

[0135] Example 41: (S)-Quinuclidin-3-yl (6-(2,5-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0136] Example 42: (S)-Quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0137] Example 43: (S)-Quinuclidin-3-yl (6-(2,4-difluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0138] Example 44: (S)-Quinuclidin-3-yl (6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0139] Example 45: (S)-Quinuclidin-3-yl (6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0140] Example 46: (S)-Quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0141] Example 47: (S)-Quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0142] Example 48: (S)-Quinuclidin-3-yl (6-(3,5-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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, 1) H), 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)

[0143] Examples 49-72 The title compounds of Examples 49-72 were prepared using the (S)-quinuclidin-3-yl (6-bromo-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate prepared in Preparation Example 3, and the corresponding substituted phenylboronic acid, respectively, following the same procedure as in Example 1.

[0144] Example 49: (S)-Quinuclidin-3-yl (6-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0145] Example 50: (S)-Quinuclidin-3-yl (6-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0146] Example 51: (S)-Quinuclidine-3-yl (2,2-dimethyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0147] Example 52: (S)-Quinuclidine-3-yl (2,2-dimethyl-6-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0148] Example 53: (S)-Quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-NMR (400 MHz, 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)

[0149] Example 54: (S)-Quinuclidin-3-yl (6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-NMR (400 MHz, 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)

[0150] Example 55: (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0151] Example 56: (S)-Quinuclidine-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0152] Example 57: (S)-Quinuclidin-3-yl (6-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0153] Example 58: (S)-Quinuclidin-3-yl (6-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-NMR (400 MHz, 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)

[0154] Example 59: (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-NMR (400 MHz, 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)

[0155] Example 60: (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(p-tolyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-NMR (400 MHz, 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)

[0156] Example 61: (S)-Quinuclidin-3-yl (6-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0157] Example 62: (S)-Quinuclidin-3-yl (6-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0158] Example 63: (S)-Quinuclidin-3-yl (6-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0159] Example 64: (S)-Quinuclidin-3-yl (6-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0160] Example 65: (S)-Quinuclidin-3-yl (6-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0161] Example 66: (S)-Quinuclidin-3-yl (6-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0162] Example 67: (S)-Quinuclidin-3-yl (2,2-dimethyl-6-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0163] Example 68: (S)-Quinuclidin-3-yl (2,2-dimethyl-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0164] Example 69: (S)-Quinuclidin-3-yl (6-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0165] Example 70: (S)-Quinuclidin-3-yl (6-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0166] Example 71: (S)-Quinuclidin-3-yl (6-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0167] Example 72: (S)-Quinuclidine-3-yl (6-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0168] Examples 73-275 The title compounds of Examples 73-275 were prepared using the (S)-quinuclidin-3-yl (5-bromo-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate prepared in Preparation Example 4, and the corresponding substituted phenylboronic acid, respectively, following the same procedure as in Example 1.

[0169] Example 73: (S)-Quinuclidin-3-yl (5-(4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0170] Example 74: (S)-Quinuclidin-3-yl (5-(4-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0171] Example 75: (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0172] Example 76: (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0173] Example 77: (S)-Quinuclidine-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0174] Example 78: (S)-Quinuclidin-3-yl (5-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0175] Example 79: (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0176] Example 80: (S)-Quinuclidine-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0177] Example 81: (S)-Quinuclidin-3-yl (5-(2-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0178] Example 82: (S)-Quinuclidin-3-yl (5-(2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0179] Example 83: (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(2-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0180] Example 84: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0181] Example 85: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(p-tolyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0182] Example 86: (S)-Quinuclidin-3-yl (5-(4-(difluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0183] Example 87: (S)-Quinuclidin-3-yl (5-(3,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0184] Example 88: (S)-Quinuclidin-3-yl (5-(2,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0185] Example 89: (S)-Quinuclidin-3-yl (5-(2,4-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0186] Example 90: (S)-Quinuclidin-3-yl (5-(3,5-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0187] Example 91: (S)-Quinuclidin-3-yl (5-(2,3-difluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0188] Example 92: (S)-Quinuclidin-3-yl (5-(3,4-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0189] Example 93: (S)-Quinuclidin-3-yl (5-(2,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0190] Example 94: (S)-Quinuclidin-3-yl (5-(3,5-dichlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0191] Example 95: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2,3,4-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0192] Example 96: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0193] Example 97: (S)-Quinuclidin-3-yl (5-(4-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0194] Example 98: (S)-Quinuclidine-3-yl (5-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0195] Example 99: (S)-Quinuclidine-3-yl (5-(2-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0196] Example 100: (S)-Quinuclidine-3-yl (5-(4-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0197] Example 101: (S)-Quinuclidin-3-yl (5-(3-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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, 3) H), 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)

[0198] Example 102: (S)-Quinuclidine-3-yl (5-(2-(methoxymethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0199] Example 103: (S)-Quinuclidine-3-yl (5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0200] Example 104: (S)-Quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0201] Example 105: (S)-Quinuclidin-3-yl (5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0202] Example 106: (S)-Quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0203] Example 107: (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(3-(methylthio)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0204] Example 108: (S)-Quinuclidin-3-yl (5-(3-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0205] Example 109: (S)-Quinuclidin-3-yl (5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0206] Example 110: (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0207] Example 111: (S)-Quinuclidin-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0208] Example 112: (S)-Quinuclidin-3-yl (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0209] Example 113: (S)-Quinuclidin-3-yl (5-(2,3-dihydrobenzofuran-5-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0210] Example 114: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-(2-morpholinoethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0211] Example 115: (S)-Quinuclidin-3-yl (5-(4-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0212] Example 116: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-(2,2,2-trifluoroethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0213] Example 117: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-(2-morpholinoethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0214] Example 118: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(2-(trifluoromethyl)pyridine-4-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0215] Example 119: (S)-Quinuclidin-3-yl (5-(2,5-dichloropyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0216] Example 120: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-NMR (400 MHz, 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)

[0217] Example 121: (S)-Quinuclidin-3-yl (5-(2-chloro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0218] Example 122: (S)-Quinuclidin-3-yl (5-(3-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0219] Example 123: (S)-Quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0220] Example 124: (S)-Quinuclidin-3-yl (5-(2-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0221] Example 125: (S)-Quinuclidin-3-yl (5-(4-chloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0222] Example 126: (S)-Quinuclidin-3-yl (5-(2,3-dichloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0223] Example 127: (S)-Quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0224] Example 128: (S)-Quinuclidin-3-yl (5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0225] Example 129: (S)-Quinuclidin-3-yl (5-(3-(dimethylamino)-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0226] Example 130: (S)-Quinuclidin-3-yl (5-(chroman-6-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0227] Example 131: (S)-Quinuclidin-3-yl (5-(4-cyclopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0228] Example 132: (S)-Quinuclidin-3-yl (5-(4-(dimethylamino)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0229] Example 133: (S)-Quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0230] Example 134: (S)-Quinuclidin-3-yl (5-(4-Methoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0231] Example 135: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0232] Example 136: (S)-Quinuclidin-3-yl (5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0233] Example 137: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(thiophen-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0234] Example 138: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-methylthiophen-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0235] Example 139: (S)-Quinuclidin-3-yl (5-(3-(2-(dimethylamino)ethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0236] Example 140: (S)-Quinuclidin-3-yl (5-(Isoquinoline-8-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0237] Example 141: (S)-Quinuclidin-3-yl (5-(Isoquinoline-5-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0238] Example 142: (S)-Quinuclidin-3-yl (5-(Isoquinoline-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0239] Example 143: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0240] Example 144: (S)-Quinuclidin-3-yl (5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0241] Example 145: (S)-Quinuclidin-3-yl (5-(2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0242] Example 146: (S)-Quinuclidin-3-yl (5-(4-(tert-butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0243] Example 147: (S)-Quinuclidin-3-yl (5-(4-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0244] Example 148: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-morpholinophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0245] Example 149: (S)-Quinuclidin-3-yl (5-(4-(methoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0246] Example 150: (S)-Quinuclidin-3-yl (5-(4-(2,2-difluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0247] Example 151: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-methyl-4-morpholinophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0248] Example 152: (S)-Quinuclidin-3-yl (5-(3-fluoro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.1 4(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)

[0249] Example 153: (S)-Quinuclidin-3-yl (5-(3-chloro-4-morpholinophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0250] 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-inden-1-yl)carbamate 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), 3.2 5(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)

[0251] Example 155: (S)-Quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0252] Example 156: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(quinoline-8-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-NMR (400 MHz, 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)

[0253] Example 157: (S)-Quinuclidin-3-yl (5-(benzofuran-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 3.2 5(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)

[0254] Example 158: (S)-Quinuclidin-3-yl (5-(benzofuran-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0255] Example 159: (S)-Quinuclidin-3-yl (5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.2 5(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)

[0256] Example 160: (S)-Quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0257] Example 161: (S)-Quinuclidin-3-yl (5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0258] Example 162: (S)-Quinuclidin-3-yl (5-(2,4-dichloro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0259] Example 163: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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), 2.91~2.7 4(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)

[0260] Example 164: (S)-Quinuclidin-3-yl (5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 2.91~2.7 4(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)

[0261] Example 165: (S)-Quinuclidin-3-yl (5-(2,3-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0262] Example 166: (S)-Quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.2 5(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)

[0263] Example 167: (S)-Quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 3.2 5(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)

[0264] Example 168: (S)-Quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0265] Example 169: (S)-Quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.2 5(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)

[0266] Example 170: (S)-Quinuclidin-3-yl (5-(4-ethoxy-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0267] Example 171: (S)-Quinuclidin-3-yl (5-(2,5-difluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 2.9 1~2.74(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)

[0268] Example 172: (S)-Quinuclidin-3-yl (5-(2-fluoro-5-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0269] Example 173: (S)-Quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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), 2.91~2.7 4(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)

[0270] Example 174: (S)-Quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0271] Example 175: (S)-Quinuclidin-3-yl (5-(2-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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), 2.9 1~2.74(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)

[0272] Example 176: (S)-Quinuclidine-3-yl (5-(2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0273] Example 177: (S)-Quinuclidin-3-yl (5-(2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0274] Example 178: (S)-Quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 2.9 1~2.74(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)

[0275] Example 179: (S)-Quinuclidin-3-yl (5-(4-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 2.9 1~2.74(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)

[0276] Example 180: (S)-Quinuclidine-3-yl (5-(4-methoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0277] Example 181: (S)-Quinuclidin-3-yl (5-(4-(tert-butoxymethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0278] Example 182: (S)-Quinuclidin-3-yl (5-(2-chloro-3-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0279] Example 183: (S)-Quinuclidin-3-yl (5-(2-chloro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0280] Example 184: (S)-Quinuclidin-3-yl (5-(2,6-dimethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.2 5(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)

[0281] Example 185: (S)-Quinuclidine-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0282] Example 186: (S)-Quinuclidin-3-yl (5-(benzo[b]thiophen-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 2.9 1~2.74(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)

[0283] Example 187: (S)-Quinuclidin-3-yl (5-(2-(tert-butoxy)pyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 2.9 1~2.74(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)

[0284] Example 188: (S)-Quinuclidine-3-yl (5-(6-Methoxy-5-(trifluoromethyl)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0285] Example 189: (S)-Quinuclidine-3-yl (5-(6-methoxynaphthalene-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0286] Example 190: (S)-Quinuclidin-3-yl (5-([1,1'-biphenyl]-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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), 3.2 5(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)

[0287] Example 191: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(quinoxaline-6-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0288] Example 192: (S)-Quinuclidin-3-yl (5-(3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0289] Example 193: (S)-Quinuclidin-3-yl (5-(Fran-2-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0290] Example 194: (S)-Quinuclidin-3-yl (5-(4-Isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0291] Example 195: (S)-Quinuclidin-3-yl (5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0292] Example 196: (S)-Quinuclidin-3-yl (5-(6-Isopropoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 2.9 1~2.74(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)

[0293] Example 197: (S)-Quinuclidin-3-yl (5-(3-(2-fluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0294] Example 198: (S)-Quinuclidin-3-yl (5-(2-ethoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-NMR (400 MHz, 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)

[0295] Example 199: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0296] Example 200: (S)-Quinuclidin-3-yl (5-(2-methoxy-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0297] Example 201: (S)-Quinuclidin-3-yl (5-(2-butoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.2 5(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)

[0298] Example 202: (S)-Quinuclidin-3-yl (5-(4-butoxy-3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0299] Example 203: (S)-Quinuclidin-3-yl (5-(2,4-dipropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.2 5(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)

[0300] Example 204: (S)-Quinuclidin-3-yl (5-(3-chloro-4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0301] Example 205: (S)-Quinuclidin-3-yl (5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0302] Example 206: (S)-Quinuclidin-3-yl (5-(4-ethoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0303] Example 207: (S)-Quinuclidin-3-yl (5-(3-chloro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0304] Example 208: (S)-Quinuclidin-3-yl (5-(5-fluoro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0305] Example 209: (S)-Quinuclidin-3-yl (5-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0306] Example 210: (S)-Quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0307] Example 211: (S)-Quinuclidin-3-yl (5-(2-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0308] Example 212: (S)-Quinuclidin-3-yl (5-(5-chloro-2-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0309] Example 213: (S)-Quinuclidin-3-yl (5-(5-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0310] Example 214: (S)-Quinuclidin-3-yl (5-(2-fluoro-6-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0311] Example 215: (S)-Quinuclidin-3-yl (5-(3-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0312] Example 216: (S)-Quinuclidin-3-yl (5-(3-fluoro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0313] Example 217: (S)-Quinuclidin-3-yl (5-(5-chloro-2-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0314] Example 218: (S)-Quinuclidin-3-yl (5-(3-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0315] Example 219: (S)-Quinuclidin-3-yl (5-(3-fluoro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0316] Example 220: (S)-Quinuclidin-3-yl (5-(5-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0317] Example 221: (S)-Quinuclidin-3-yl (5-(2-chloro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0318] Example 222: (S)-Quinuclidin-3-yl (5-(3-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0319] Example 223: (S)-Quinuclidin-3-yl (5-(2-chloro-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0320] Example 224: (S)-Quinuclidine-3-yl (5-(3-methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0321] Example 225: (S)-Quinuclidin-3-yl (5-(2-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0322] Example 226: (S)-Quinuclidin-3-yl (5-(4-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0323] Example 227: (S)-Quinuclidin-3-yl (5-(3,4-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0324] Example 228: (S)-Quinuclidin-3-yl (5-(4-fluoro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0325] Example 229: (S)-Quinuclidin-3-yl (5-(2-fluoro-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0326] Example 230: (S)-Quinuclidin-3-yl (5-(2-fluoro-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0327] Example 231: (S)-Quinuclidin-3-yl (5-(2-fluoro-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0328] Example 232: (S)-Quinuclidine-3-yl (5-(5-isopropyl-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0329] Example 233: (S)-Quinuclidin-3-yl (5-(2-fluoro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0330] Example 234: (S)-Quinuclidin-3-yl (5-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0331] Example 235: (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(5-methylfuran-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0332] Example 236: (S)-Quinuclidin-3-yl (5-(3-fluoro-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0333] Example 237: (S)-Quinuclidin-3-yl (5-(2-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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, 7) H), 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)

[0334] Example 238: (S)-Quinuclidine-3-yl (5-(benzo[b]thiophen-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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, 7) H), 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)

[0335] Example 239: (S)-Quinuclidin-3-yl (5-(4-fluoro-2-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0336] Example 240: (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)-5-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0337] Example 241: (S)-Quinuclidin-3-yl (5-(2-chloro-5-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 3.2 5(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)

[0338] Example 242: (S)-Quinuclidin-3-yl (5-(4-chloro-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0339] Example 243: (S)-Quinuclidin-3-yl (5-(2-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0340] Example 244: (S)-Quinuclidin-3-yl (5-(5-cyano-2-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0341] Example 245: (S)-Quinuclidin-3-yl (5-(3-ethoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0342] Example 246: (S)-Quinuclidin-3-yl (5-(3-fluoro-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0343] Example 247: (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(3-methyl-4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0344] Example 248: (S)-Quinuclidine-3-yl (2,2-dimethyl-5-(3-(methylthio)-5-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0345] Example 249: (S)-Quinuclidin-3-yl (5-(3-fluoro-4-(trifluoromethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0346] Example 250: (S)-Quinuclidin-3-yl (5-(2-ethoxy-4-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0347] Example 251: (S)-Quinuclidine-3-yl (5-(2-Methoxy-5-(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0348] Example 252: (S)-Quinuclidin-3-yl (5-(2,4-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0349] Example 253: (S)-Quinuclidin-3-yl (5-(3-chloro-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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, 7 H), 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)

[0350] Example 254: (S)-Quinuclidine-3-yl (5-(3-methoxy-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0351] Example 255: (S)-Quinuclidin-3-yl (5-(4-fluoro-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0352] Example 256: (S)-Quinuclidin-3-yl (5-(2-ethoxy-5-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0353] Example 257: (S)-Quinuclidin-3-yl (5-(3-fluoro-5-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0354] Example 258: (S)-Quinuclidin-3-yl (5-(3,5-bis(trifluoromethyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0355] Example 259: (S)-Quinuclidin-3-yl (5-(3-chloro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0356] Example 260: (S)-Quinuclidin-3-yl (5-(2,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0357] Example 261: (S)-Quinuclidin-3-yl (5-(3-chloro-4-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0358] Example 262: (S)-Quinuclidin-3-yl (5-(6-ethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0359] Example 263: (S)-Quinuclidin-3-yl (5-(2-ethoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0360] Example 264: (S)-Quinuclidin-3-yl (5-(2-Isopropoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0361] Example 265: (S)-Quinuclidin-3-yl (2,2-dimethyl-5-(6-propoxypyridine-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0362] Example 266: (S)-Quinuclidin-3-yl (5-(6-butoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0363] Example 267: (S)-Quinuclidine-3-yl (5-(6-(2-methoxyethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0364] Example 268: (S)-Quinuclidin-3-yl (5-(6-isobutoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0365] Example 269: (S)-Quinuclidin-3-yl (5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0366] Example 270: (S)-Quinuclidin-3-yl (5-(4-butoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0367] Example 271: (S)-Quinuclidin-3-yl (5-(2,4-dimethoxypyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0368] Example 272: (S)-Quinuclidine-3-yl (5-(2-acetylthiophen-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0369] Example 273: (S)-Quinuclidin-3-yl (5-((E)-3-fluorostyryl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0370] Example 274: (S)-Quinuclidin-3-yl (5-((E)-4-ethylstyryl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0371] Example 275: (S)-Quinuclidin-3-yl (5-((E)-2-cyclohexylvinyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0372] Examples 276-311 The title compounds of Examples 276-311 were prepared using the (S)-quinuclidin-3-yl (5-bromo-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate prepared in Preparation Example 5, and the corresponding substituted boronic acid, respectively, following the same procedure as in Example 1.

[0373] Example 276: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-NMR (400MHz, 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)

[0374] Example 277: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-ethylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0375] Example 278: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0376] Example 279: (S)-Quinuclidin-3-yl (5-(4-(tert-butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0377] Example 280: (S)-Quinuclidin-3-yl (5-(4-butylphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0378] Example 281: (S)-Quinuclidine-3-yl (5-(4-cyclopropylphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0379] Example 282: (S)-Quinuclidine-3-yl (2,2-diethyl-5-(4-isopropylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0380] Example 283: (S)-Quinuclidine-3-yl (2,2-diethyl-5-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0381] Example 284: (S)-Quinuclidin-3-yl (5-(4-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0382] Example 285: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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), 2.8 8~2.71(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)

[0383] Example 286: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-isopropoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0384] Example 287: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(4-isobutylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0385] Example 288: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0386] Example 289: (S)-Quinuclidine-3-yl (2,2-diethyl-5-(3-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0387] Example 290: (S)-Quinuclidin-3-yl (5-(3-ethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0388] Example 291: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(3-isopropoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0389] Example 292: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(3-ethylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0390] Example 293: (S)-Quinuclidine-3-yl (2,2-diethyl-5-(3-isopropylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0391] Example 294: (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0392] Example 295: (S)-Quinuclidine-3-yl (5-(2,3-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0393] Example 296: (S)-Quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0394] Example 297: (S)-Quinuclidine-3-yl (5-(2,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0395] Example 298: (S)-Quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0396] Example 299: (S)-Quinuclidine-3-yl (5-(3,5-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 3.2 4(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)

[0397] Example 300: (S)-Quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0398] Example 301: (S)-Quinuclidin-3-yl (5-(3-(difluoromethyl)phenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0399] Example 302: (S)-Quinuclidin-3-yl (5-(3-(dimethylamino)phenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0400] Example 303: (S)-Quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0401] Example 304: (S)-Quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0402] Example 305: (S)-Quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0403] Example 306: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(thiophen-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0404] Example 307: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(furan-3-yl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0405] Example 308: (S)-Quinuclidine-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0406] Example 309: (S)-Quinuclidine-3-yl (5-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0407] Example 310: (S)-Quinuclidin-3-yl (2,2-diethyl-5-(2-fluoro-4-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0408] Example 311: (S)-Quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-2,2-diethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0409] Examples 312-348 The title compounds of Examples 312-348 were prepared using the (S)-quinuclidin-3-yl (5-bromo-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate prepared in Preparation Example 6, and the corresponding substituted boronic acid, respectively, following the same procedure as in Example 1.

[0410] Example 312: (S)-Quinuclidin-3-yl (5-(4-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0411] Example 313: (S)-Quinuclidine-3-yl (6-Methoxy-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0412] Example 314: (S)-Quinuclidin-3-yl (5-(4-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0413] Example 315: (S)-Quinuclidine-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0414] Example 316: (S)-Quinuclidin-3-yl (5-(4-(tert-butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0415] Example 317: (S)-Quinuclidine-3-yl (5-(4-cyclopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0416] Example 318: (S)-Quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0417] Example 319: (S)-Quinuclidin-3-yl (6-Methoxy-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0418] Example 320: (S)-Quinuclidin-3-yl (5-(4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0419] Example 321: (S)-Quinuclidin-3-yl (5-(3,5-dimethyl-4-propoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0420] Example 322: (S)-Quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0421] Example 323: (S)-Quinuclidine-3-yl (5-(2-fluoro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0422] Example 324: (S)-Quinuclidin-3-yl (5-(4-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0423] Example 325: (S)-Quinuclidin-3-yl (5-(4-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0424] Example 326: (S)-Quinuclidine-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0425] Example 327: (S)-Quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0426] Example 328: (S)-Quinuclidin-3-yl (5-(4-butylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0427] Example 329: (S)-Quinuclidine-3-yl (6-Methoxy-5-(4-Methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0428] Example 330: (S)-Quinuclidine-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0429] Example 331: (S)-Quinuclidine-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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), 2.3 1(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)

[0430] Example 332: (S)-Quinuclidine-3-yl (6-Methoxy-5-(2-Methoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0431] Example 333: (S)-Quinuclidine-3-yl (5-(3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0432] Example 334: (S)-Quinuclidine-3-yl (5-(3-ethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0433] Example 335: (S)-Quinuclidine-3-yl (5-(3-isobutylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0434] Example 336: (S)-Quinuclidine-3-yl (5-(3-isopropylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0435] Example 337: (S)-Quinuclidine-3-yl (5-(3-(tert-butyl)phenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0436] Example 338: (S)-Quinuclidine-3-yl (6-Methoxy-5-(3-Methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0437] Example 339: (S)-Quinuclidine-3-yl (5-(3-ethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0438] Example 340: (S)-Quinuclidin-3-yl (6-Methoxy-2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0439] Example 341: (S)-Quinuclidin-3-yl (5-(3-isopropoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 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)

[0440] Example 342: (S)-Quinuclidin-3-yl (5-(3-butoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0441] Example 343: (S)-Quinuclidine-3-yl (5-(3-isobutoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 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)

[0442] Example 344: (S)-Quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0443] Example 345: (S)-Quinuclidine-3-yl (5-(3,5-dimethoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0444] Example 346: (S)-Quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0445] Example 347: (S)-Quinuclidine-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0446] Example 348: (S)-Quinuclidin-3-yl (5-(4-isopropoxy-3,5-dimethylphenyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0447] Examples 349-388 The title compounds of Examples 349-388 were prepared using the (S)-quinuclidin-3-yl (5-bromo-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate prepared in Preparation Example 7, and the corresponding substituted boronic acid, respectively, following the same procedure as in Example 1.

[0448] Example 349: (S)-Quinuclidin-3-yl (5-(4-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0449] Example 350: (S)-Quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0450] Example 351: (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0451] Example 352: (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0452] Example 353: (S)-Quinuclidin-3-yl (5-(4-(tert-butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0453] Example 354: (S)-Quinuclidin-3-yl (5-(4-cyclopropylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0454] Example 355: (S)-Quinuclidine-3-yl (6-fluoro-5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0455] Example 356: (S)-Quinuclidin-3-yl (5-(4-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0456] Example 357: (S)-Quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0457] Example 358: (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0458] Example 359: (S)-Quinuclidin-3-yl (5-(3-chloro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0459] Example 360: (S)-Quinuclidin-3-yl (6-fluoro-5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0460] Example 361: (S)-Quinuclidin-3-yl (5-(4-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0461] Example 362: (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0462] Example 363: (S)-Quinuclidine-3-yl (5-(6-(cyclopropylmethoxy)pyridine-3-yl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0463] Example 364: (S)-Quinuclidin-3-yl (5-(5-chloro-2-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0464] Example 365: (S)-Quinuclidin-3-yl (5-(4-butylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0465] Example 366: (S)-Quinuclidin-3-yl (6-fluoro-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0466] Example 367: (S)-Quinuclidin-3-yl (5-(4-ethoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0467] Example 368: (S)-Quinuclidin-3-yl (5-(4-butoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0468] Example 369: (S)-Quinuclidin-3-yl (6-fluoro-5-(2-methoxypyridine-4-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0469] Example 370: (S)-Quinuclidin-3-yl (6-Fluoro-5-(3-Fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0470] Example 371: (S)-Quinuclidin-3-yl (5-(3-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0471] Example 372: (S)-Quinuclidin-3-yl (6-fluoro-5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0472] Example 373: (S)-Quinuclidin-3-yl (6-fluoro-5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0473] Example 374: (S)-Quinuclidin-3-yl (5-(3-(tert-butyl)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0474] Example 375: (S)-Quinuclidine-3-yl (6-fluoro-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 6.91(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)

[0475] Example 376: (S)-Quinuclidin-3-yl (5-(3-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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), 6.89(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)

[0476] Example 377: (S)-Quinuclidin-3-yl (6-fluoro-2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H-NMR (400 MHz, 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)

[0477] Example 378: (S)-Quinuclidin-3-yl (6-fluoro-5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0478] Example 379: (S)-Quinuclidin-3-yl (5-(3-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0479] Example 380: (S)-Quinuclidin-3-yl (6-fluoro-5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0480] Example 381: (S)-Quinuclidin-3-yl (5-(2,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0481] Example 382: (S)-Quinuclidin-3-yl (5-(2,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0482] Example 383: (S)-Quinuclidin-3-yl (5-(2,6-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0483] Example 384: (S)-Quinuclidin-3-yl (5-(3,5-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0484] Example 385: (S)-Quinuclidin-3-yl (5-(3,4-dimethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H-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)

[0485] Example 386: (S)-Quinuclidin-3-yl (5-(2-chloro-4-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1H-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)

[0486] Example 387: (S)-Quinuclidin-3-yl (5-(4-ethoxy-3-fluorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0487] Example 388: (S)-Quinuclidin-3-yl (6-fluoro-5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0488] Examples 389-398 The title compounds of Examples 389-398 were prepared using the (S)-quinuclidin-3-yl (5'-bromo-1',3'-dihydrospiro[cyclopropane-1,2'-inden]-1'-yl)carbamate prepared in Preparation Example 8, and the corresponding substituted phenylboronic acid, respectively, following the same procedure as in Example 1.

[0489] Example 389: (S)-Quinuclidin-3-yl (5'-(4-fluorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 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), 2.9 1~2.72(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)

[0490] Example 390: (S)-Quinuclidin-3-yl (5'-(4-chlorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 1 H-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)

[0491] Example 391: (S)-Quinuclidin-3-yl (5'-(4-(trifluoromethyl)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 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)

[0492] Example 392: (S)-Quinuclidin-3-yl (5'-(4-(trifluoromethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 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), 2.9 5~2.76(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)

[0493] Example 393: (S)-Quinuclidin-3-yl (5'-(3-chlorophenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 1H-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), 2.91~2.7 2(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)

[0494] Example 394: (S)-Quinuclidin-3-yl (5'-(3-(trifluoromethyl)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 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), 2.91~2.7 2(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)

[0495] Example 395: (S)-Quinuclidin-3-yl (5'-(4-(2-methoxyethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 1H-NMR (400 MHz, 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)

[0496] Example 396: (S)-Quinuclidin-3-yl (5'-(3-(2-methoxyethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 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)

[0497] Example 397: (S)-Quinuclidin-3-yl (5'-(4-(methoxymethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 1H-NMR (400 MHz, 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)

[0498] Example 398: (S)-Quinuclidine-3-yl (5'-(3-(methoxymethoxy)phenyl)-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-1'-yl)carbamate 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), 5.22(s, 2H), 5.02(m, 1H), 4.92(m, 1H), 4.75(m, 1H), 3.51(s, 3H), 3.25(m, 1H), 3.0 8(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)

[0499] Examples 399-403 The title compounds of Examples 399-403 were prepared using the (S)-quinuclidin-3-yl (5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate prepared in Preparation Example 9, and the corresponding substituted phenylboronic acid, respectively, following the same procedure as in Example 1.

[0500] Example 399: (S)-Quinuclidin-3-yl (5-(3-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0501] Example 400: (S)-Quinuclidin-3-yl (5-(2-chlorophenyl)-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate 1 H 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)

[0502] Example 401: (S)-Quinuclidin-3-yl (3,3-dimethyl-5-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 1H 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), 2.92~2.7 3(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)

[0503] Example 402: (S)-Quinuclidine-3-yl (3,3-dimethyl-5-(3-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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, 5) H), 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)

[0504] Example 403: (S)-Quinuclidine-3-yl (3,3-dimethyl-5-(2-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 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)

[0505] Examples 404 and 405 The title compounds of Examples 404 and 405 were prepared using the (S)-quinuclidin-3-yl (6-bromodihydrobenzofuran-3-yl)carbamate prepared in Preparation Example 10 and the corresponding substituted phenylboronic acid, respectively, following the same procedure as in Example 1.

[0506] Example 404: (S)-Quinuclidin-3-yl (6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate 1 H-NMR (400 MHz, 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), 2.0 3~2.00(m, 1H), 1.77~1.65(m, 2H), 1.59~1.57(m, 1H), 1.45~1.30(m, 1H)

[0507] Example 405: (S)-Quinuclidine-3-yl (6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate 1 H-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)

[0508] Example 406: (S)-Quinuclidin-3-yl (5-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate The title compound was prepared using (S)-quinuclidin-3-yl (5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate and 3-fluorophenylboronic acid, prepared in Preparation Example 11, following the same procedure as in Example 1. 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, 1 H), 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)

[0509] Examples 407-411 The title compounds of Examples 407-411 were prepared using the (S)-quinuclidin-3-yl (6-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate prepared in Preparation Example 12, and the corresponding substituted phenylboronic acid, respectively, following the same procedure as in Example 1.

[0510] Example 407: (S)-Quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate 1H-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)

[0511] Example 408: (S)-Quinuclidin-3-yl (6-(3-chlorophenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate 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)

[0512] Example 409: (S)-Quinuclidine-3-yl (2,2-dimethyl-6-(3-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate 1H-NMR (400 MHz, 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)

[0513] Example 410: (S)-Quinuclidine-3-yl (2,2-dimethyl-6-(3-(trifluoromethoxy)phenyl)-2,3-dihydrobenzofuran-3-yl)carbamate 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)

[0514] Example 411: (S)-Quinuclidin-3-yl (6-(3-(2-methoxyethoxy)phenyl)-2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)carbamate 1H-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)

[0515] Test Example 1: Evaluation of inhibitory activity against GCS The inhibitory activity of the compounds of the present invention against GCS was evaluated as follows, according to the method described in a known document (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 Biochemistry 345 (2005) 181-186). Ibiglustat, known as a GCS inhibitor, was used as a control substance.

[0516] (1) Material A549 cells (ATCC, CCL-185) NBD C6-Ceramide (Thermo Fisher, N1154) UDP-glucose (Sigma, U4625) Potassium chloride (Sigma, P9333) UltraPure TM 0.5M EDTA (Invitrogen, 15575-038) BCA Protein Assay Kit (Thermo Fisher, 23227) Iviglustat (Shanghai Systeam Biochem Co., Ltd., Genz-682452) HEPES (sigma, H3375) Protease / phosphatase inhibitor cocktail (CST, 5872s) DMEM (GIBCO, 11995-065) FBS (GIBCO, 16000-044) Antibiotic-Antimycotic(100X)(GIBCO, 15240-112) 200 mM L-glutamine (GIBCO, 25030081) PBS (GIBCO, 10010-023) 0.25% Trypsin-EDTA (GIBCO, 25200-056) Dimethyl sulfoxide (Sigma, 34869) 2-Propanol, HPLC grade (Burdick & Jackson, AH323-4) Hexane, HPLC grade (Burdick & Jackson, AH216-4) Chloroform (Sigma, C2432) Methanol (Merck, 1.06009.1011)

[0517] (2) Protocol <1> Preparation of cell lysates A549 cells (ATCC, CCL-185) were cultured in DMEM medium supplemented with 10% fetal bovine serum (FBS), 1x Antibiotic-Antimycotic, and 1x L-glutamine in a 37°C, 5% CO2 incubator. After washing the cells attached to the culture dish with phosphate-buffered saline (PBS), the cells were scraped off with a cell scraper and centrifuged (4000 rpm, 3 min, 4°C) to collect the cells in a 50 ml tube. The cell pellet was suspended in lysis buffer (50 mM HEPES, pH 7.3, containing a 1x protease / phosphatase inhibitor cocktail), lysed by sonication, and the lysate was centrifuged (13000 rpm, 10 min, 4°C). The resulting supernatant was used for quantitative protein analysis. Protein levels were measured using a BCA protein assay kit with bovine serum albumin as the standard.

[0518] <2> GCS enzyme reaction The enzymatic reaction was initiated by sequentially adding the following reactants to a 96-deep-well plate. The reaction was then carried out at 37°C for 90 minutes. [Table 1]

[0519] <3> lipid extraction The enzymatic reaction was stopped by adding 100 μl of chloroform / methanol (2:1, v / v). After vortexing for 15 seconds, each mixture was centrifuged (4000 rpm, 10 min, 18°C). The lower layer (50 μl) was transferred to a new 96-deep-well plate and dried in a vacuum concentrator.

[0520] <4> HPLC analysis The lipid was dissolved in 100 μl of isopropyl alcohol / n-hexane / H2O (55:44:1, v / v / v) and transferred to an HPLC glass vial (Agilent, 8004-HP-H / i3u). The sample (100 μl) was automatically loaded onto a normal-phase column (Intersil SIL 150A-5, 4.6 x 250 mm, GL Sciences, Japan) and eluted with isopropyl alcohol / n-hexane / H2O (55:44:1, v / v / v) at a flow rate of 2.0 ml / min. The fluorescence was measured using a fluorescence detector (Agilent, 1260 FLD Spectra) with excitation and emission wavelengths of 470 nm and 530 nm, respectively.

[0521] <5> Data Analysis Data analysis was performed using the following formula. % Area (Sample) = Area (GlcCer) / [Area (Cer) + Area (GlcCer)] x 100 %GCS activity = [Area (sample) - Area (ibiglustat)] / [Area (DMSO) - Area (ibiglustat)] x 100 The obtained %GCS activity data was analyzed using the software GraphPad Prism (Ver 5.01) to determine IC 50 The values ​​were calculated. The results are shown in Tables 1 to 4 below. [Table 2] TIFF0007880463000006.tif80166 [Table 3] TIFF0007880463000008.tif78165 [Table 4] TIFF0007880463000010.tif77164 [Table 5]

[0522] The results in Tables 1 to 4 show that the compounds of the present invention exhibit excellent inhibitory activity against GCS.

[0523] Test Example 2: Evaluation of inhibitory activity against GM1 production GM1, the end product of sphingolipid metabolism, is expressed on the cell membrane and is therefore easily detected. Furthermore, the amount of GM1 represents the conversion of ceramide to glucosylceramide. Accordingly, the inhibitory activity of the compounds of the present invention on GM1 production was evaluated as follows, according to the method described in known literature (Dijkhuis et al., Gangliosides do not affect ABC transporter function in human neuroblastoma cells. The Journal of Lipid Research 47 (2006). 1187-1195). Ibiglustat, known as a GCS inhibitor, was used as a control substance.

[0524] (1) Material Jurkat cells, clone E6-1 (ATCC, TIB-152) Cholera toxin subunit B (CTB), FITC (Sigma, C1655) Iviglustat (Shanghai Systeam Biochem Co., Ltd., Genz-682452) DMSO (Sigma, D2650) Fixation buffer (BD, 554655) RPMI1640 (Gibco, A1049101) FBS (Gibco, 16000-044) Antibiotic-Antimycotic (100X) (Gibco, 15240-122) FACS sheath fluid (BD, 342003) Jurkat cells were cultured in RPMI1640 medium supplemented with 10% FBS and 1X Antibiotic-Antimycotic. Washing solution was prepared by adding 10 ml of FBS to 490 ml of FACS sheath solution. CTB-FITC solution was prepared by diluting CTB-FITC stock solution (10 mg / ml) with washing solution to a final concentration of 2 μg / ml.

[0525] (2) Protocol Cell suspension (1X10 5Cells / ml were prepared in culture medium (RPMI 1640 medium supplemented with 10% FBS and 1X Antibiotic-Antimycotic). 200 μl of the cell suspension was added to each well of a 96-well plate (20,000 cells / well), and the compound was added to each well at a final concentration of 0.05–3000 nM (3x, 11 points). Each mixture was incubated in a CO2 incubator at 37°C for 72 hours. After removing the medium by centrifugation at 1500 rpm for 3 minutes, the cells were resuspended in 200 μl of washing solution per well. After removing the washing solution by centrifugation at 1500 rpm for 3 minutes, the cells were resuspended in 200 μl of 2 μg / ml CTB-FITC solution. The resulting suspension was incubated at 4°C for 60 minutes without light. After removing the CTB-FITC solution by centrifugation at 1500 rpm for 3 minutes, the cells were washed with 200 μl of washing solution. The washing process was repeated two more times. After removing the washing solution by centrifugation at 1500 rpm for 3 minutes, the cells were completely resuspended in 200 μl of fixation buffer. 50 Guava TM The values ​​were determined by quantifying FITC fluorescence using easyCyte 5HT (Merck Milipore, 0500-4005).

[0526] Data analysis was performed using the following formula. %MFI (Median Fluorescence Intensity) = (Fluorescence value of drug-treated group / Fluorescence value of DMSO-treated group) × 100 %Cells = (Cell concentration in the well / Cell concentration in the DMSO-treated group) × 100 %MFI and %cell data were analyzed using the software GraphPad Prism (Ver 5.01) to obtain IC 50 The values ​​were calculated. The results are shown in Tables 5 to 8 below. [Table 6] TIFF0007880463000013.tif78165 [Table 7] TIFF0007880463000015.tif77163 [Table 8] TIFF0007880463000017.tif77170 [Table 9]

[0527] The results in Tables 5 to 8 show that the compounds of the present invention exhibit excellent inhibitory activity against GM1 production.

Claims

1. A method for producing a compound of chemical formula 1a or a pharmaceutically acceptable salt thereof, wherein the compound of chemical formula 5 is X １ , X ２ , X ３ , or X ４ A manufacturing method comprising the step of reacting an A-W-boronic acid substituted with a compound of chemical formula 1a. 【Chemistry 1】 【Chemistry 2】 (In the formula, Y is -CR1R2- or -O-, Z is -CR 1 R 2-, R １ and R ２ are each independently hydrogen or C １ to C ６ alkyl, or R １ and R ２ together with the carbon atom to which they are attached form C ３ to C １０ cycloalkyl, X is hydrogen; halogen; C １ ~C ６ Alkyl; C substituted with 1 to 3 halogens １ ~C ６ Alkyl; C １ ~C ６ Alkoxy; or C substituted with 1 to 3 halogens １ ~C ６ It is an alkoxy, W is a bond or -CH=CH-, Ring A consists of 6-12 membered aryls; 5-12 membered heteroaryls; C ３ ~C １０ Cycloalkyl group; or a 3- to 12-membered heterocyclic group, X １ , X ２ , X ３ , and X ４ These are, independently, hydrogen; cyano; halogen; and C. １ ~C ６ Alkyl; C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl; C substituted with 1 to 3 halogens １ ~C ６ Alkyl; C ３ ~C １０ Cycloalkyl; 3- to 12-membered heterocyclic group; C １ ~C ６ Alkoxy; C substituted with 1 to 3 halogens １ ~C ６ Alkoxy; C １ ~C ６ Alkoxy-C １ ~C ６ Alkoxy;morpholinyl-C １ ~C ６ Alkoxy; mono- or di-C １ ~C ６ Alkylamino-C １ ~C ６ Alkoxy; C ３ ~C １０ Cycloalkyl-C １ ~C ６ Alkoxy; C １ ~C ６ Alkylthio; amino; mono- or di-C １ ~C ６ Alkylamino; C １ ~C ６ (It is alkylcarbonyl; hydroxy; or nitro.)

2. The manufacturing method according to claim 1, further comprising the step of converting the compound of chemical formula 1a into a pharmaceutically acceptable salt thereof.

3. Compound of chemical formula 5 and X １ , X ２ , X ３ , or X ４ The manufacturing method according to claim 1, wherein the reaction with the A-W-boronic acid substituted with is carried out using a palladium catalyst.

4. Compound of chemical formula 5 and X １ , X ２ , X ３ , or X ４ The manufacturing method according to claim 1, wherein the reaction with A-W-boronic acid substituted with is carried out in the presence of an inorganic base.

5. A method for producing a compound of chemical formula 5, obtained by coupling a compound of chemical formula 3 with quinuclidinol, according to any one of claims 1 to 4. 【Transformation 3】 (In the formula, X, Y, and Z are the same as those defined in claim 1.)

6. The manufacturing method according to claim 5, wherein the coupling is carried out by a condensation reaction including the removal of ethanol.

7. The method for producing the compound of chemical formula 3, wherein the compound of chemical formula 2 or a salt thereof is obtained by reacting it with ethyl chloroformate, according to claim 5 or 6. 【Chemistry 4】 (In the formula, X, Y, and Z are the same as those defined in claim 1.)

8. The manufacturing method according to claim 7, wherein the reaction between the compound of chemical formula 2 or a salt thereof and ethyl chloroformate is carried out in the presence of a base.

9. A manufacturing method according to any one of claims 1 to 4, wherein the compound of chemical formula 5 is obtained by reacting the compound of chemical formula 7 with the compound of chemical formula 2. 【Transformation 5】 【Transformation 6】 (In the formula, X, Y, and Z are the same as those defined in claim 1.)

10. The manufacturing method according to claim 9, wherein the reaction between the compound of chemical formula 7 and the compound of chemical formula 2 is carried out in the presence of a base.

11. The method for producing the compound of chemical formula 7 according to claim 9 or 10, wherein the compound is obtained by reacting quinuclidinol with bis(4-nitrophenyl) carbonate.

12. The method for producing the compound of chemical formula 7 according to claim 9 or 10, wherein the compound is obtained by reacting quinuclidinol with 4-nitrophenyl chloroformate.

13. Compounds of chemical formula 5: 【Transformation 7】 (In the formula, Y is -CR1R2- or -O-, Z is -CR 1 R 2-, R １ and R ２ These are, independently, hydrogen or C １ ~C ６ Alkyl or R １ and R ２ C ３ ~C １０ Forming a cycloalkyl group, X is hydrogen; halogen; C １ ~C ６ Alkyl; C substituted with 1 to 3 halogens １ ~C ６ Alkyl; C １ ~C ６ Alkoxy; or C substituted with 1 to 3 halogens １ ~C ６ It is an alkoxy.

14. Y is -CR 1 R 2 - and Z is -CR １ R ２ -The compound according to claim 13.

15. X is hydrogen, halogen, or C １ ~C ６ The compound according to claim 13, which is an alkoxy.

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