# US 10,369,140 B2 · Aryl dihydropyridinones and piperidinone MGAT2 inhibitors

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- Number: US 10,369,140 B2
- Document ID: US10369140B2
- Status: Granted
- Kind: B2
- Application number: 15/867,825
- Filed: 2018-01-11
- Published: 2018-05-17
- Granted: 2019-08-06
- Earliest claimed: 2011-12-02
- Assignees: Bristol-Myers Squibb Company
- Applicants: Bristol-Myers Squibb Company
- Inventors: Huji Turdi; Jon J. Hangeland; R. Michael Lawrence; Saleem Ahmad; Wei Meng; Robert Paul Brigance; Pratik Devasthale; Guohua Zhao
- Web page: https://patentgrep.com/patent/US10369140B2

## CPC

- A61K 31/438: The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
- A61K 31/4418: having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/50: for increasing or potentiating the activity of insulin
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 13/12: of the kidneys
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/02: Ophthalmic agents
- A61P 27/06: Antiglaucoma agents or miotics
- C07D 211/86: Oxygen atoms
- C07D 211/90: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 221/20: Spiro-condensed ring systems
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/10: linked by a carbon chain containing aromatic rings
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 407/14: containing three or more hetero rings
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero rings
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/14: containing three or more hetero rings
- C07F 9/4006: {Esters of acyclic acids which can have further substituents on alkyl}
- C07F 9/5352: {Phosphoranes containing the structure P=C-}
- C07F 9/59: Hydrogenated pyridine rings
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are monoacylglycerol acyltransferase type 2 (MGAT2) inhibitors which may be used as medicaments.

## Claims

### Claim 1

A compound of Formula (I):
or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof, wherein:
designates a single or double bond;
x and y can be both a single bond; when x is a double bond, then y is a single bond and R4 and R16 are absent; when y is a double bond, then x is a single bond and R5 and R16 are absent;
R1 is independently selected from the group consisting of: —CONH(C4-18 alkyl), —CONHC2-8 haloalkyl, —CONH(CH2)1-8Ph, —CONHCH2COC2-8 alkyl, —(CH2)m—(C3-10 carbocycle substituted with 0-2 Rb and 0-2 Rg), —(CH2)m-(5- to 6-membered heteroaryl comprising: carbon atoms and 1-4 heteroatoms selected from N, NRe, O and S; wherein said heteroaryl is substituted with 0-1 Rb and 0-2 Rg), and a C1-12 hydrocarbon chain substituted with 0-3 Ra; wherein said hydrocarbon chain may be straight or branched, saturated or unsaturated;
R2 is independently selected from the group consisting of: C1-4 alkyl, C3-4 cycloalkyl, and C1-4 haloalkyl;
R3 is independently selected from the group consisting of: H, F, Cl, C1-4 alkyl and CN;
R4 and R5 are independently selected from the group consisting of: H, F, Cl, and C1-4 alkyl;
when x is a single bond, R3 and R4 may be combined with the carbon atom to which they are attached to form a 3- to 6-membered carbocycle;
R6 is independently Rc or —(CH2)n—(X)t—(CH2)mRc;
X is independently selected from the group consisting of: O, S, NH, CONH, and NHCO;
when y is a single bond, R5 and R6 may be combined with the carbon atom to which they are attached to form a 3- to 6-membered carbocycle;
R11, R12, R13, R14 and R15 are independently selected from the group consisting of: H, halo, C1-4 alkyl substituted with 0-2 Ri, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, —(CH2)m—C3-6 cycloalkyl, CN, NRfRj, ORj, SRj, NHCO2(C1-4 alkyl), NHSO2(C1-4 alkyl), and a 4- to 6-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, NRe, O, and S;
alternatively, R11 and R12, together with the carbon atoms to which they are attached, combine to form a 5- to 6-membered carbocyclic ring or a 5- to 6-membered heterocyclic ring comprising: carbon atoms and 1-3 heteroatoms selected from N, NRe, O, and S;
alternatively, R12 and R13, together with the carbon atoms to which they are attached, combine to form a 5- to 6-membered carbocyclic ring or a 5- to 6-membered heterocyclic ring comprising: carbon atoms and 1-3 heteroatoms selected from N, NRe, O, and S;
R16 is independently selected from the group consisting of: H and C1-4 alkyl;
Ra is, at each occurrence, independently selected from the group consisting of: halo, OH,
C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, N(C1-4 alkyl)2, —(CH2)n—(X)t—(CH2)mRc, and —(CH2)n—(CH2O)m—(CH2)nRf;
Rb is, at each occurrence, independently selected from the group consisting of: halo, OH, C1-10 alkyl, C1-10 alkoxy, C1-10 haloalkyl, C1-10 haloalkoxy, C1-10 alkylthio, C1-10 haloalkylthio, N(C1-4 alkyl)2, —CONH(CH2)4-20H, —O(CH2)sO(C1-6 alkyl), Rc, —(CH2)n—(X)t—(CH2)mRc, and —(CH2)n—(CH2O)m—(CH2)nRf;
Rc is, at each occurrence, independently selected from the group consisting of: C3-6 cycloalkyl substituted with 0-2 Rd, C3-6 cycloalkenyl substituted with 0-2 Rd, —(CH2)m-(phenyl substituted with 0-3 Rd), and a 5- to 6-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, NRe, O, and S; wherein said heterocycle is substituted with 0-2 Rd;
Rd is, at each occurrence, independently selected from the group consisting of: halo, OH, CN, NO2, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, tetrazolyl, OBn and phenyl substituted with 0-2 Rh;
Re is, at each occurrence, independently selected from the group consisting of: H, C1-8 alkyl, C1-8 haloalkyl, benzyl optionally substituted with C1-4 alkoxy, CO(C1-4 alkyl) and COBn;
Rf is, at each occurrence, independently selected from the group consisting of: H and C1-4 alkyl;
Rg, Rh and Ri are, at each occurrence, independently selected from the group consisting of: halo, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, and C1-4 haloalkoxy;
Rj is, at each occurrence, independently selected from the group consisting of: C1-4 alkyl, C3-4 cycloalkyl and phenyl;
n, at each occurrence, is independently 0 or 1;
m, at each occurrence, is independently 0, 1, 2, 3, or 4
s, at each occurrence, is independently 1, 2, or 3; and
t, at each occurrence, is independently 0 or 1.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein:
R1 is independently selected from the group consisting of: —CONHC4-18 alkyl, —CONH(CH2)1-8 Ph, C1-12 alkyl substituted with 0-2 Ra, C1-12 alkenyl substituted with 0-2 Ra, C1-12 alkynyl substituted with 0-2 Ra, —(CH2)m-(phenyl substituted with 0-1 Rb and 0-2 Rg), —(CH2)m—(C3-6 cycloalkyl substituted with 0-1 Rb), and —(CH2)m-(5- to 6-membered heteroaryl substituted with 0-1 Rb and 0-2 Rg), wherein said heteroaryl is selected from: pyridyl, oxazolyl, thiazolyl and

### Claim 3 (depends on 2)

A compound according to claim 2, wherein:
R11 and R15 are independently selected from the group consisting of: H, C1-4 alkyl and halo;
R12 and R14 are independently selected from the group consisting of: H, halo, C1-4 alkyl and C1-4 alkoxy; and
R13 is independently selected from the group consisting of: H, halo, C1-4 alkyl substituted with 0-1 Ri, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, —(CH2)m—C3-4 cycloalkyl, CN, NRfRj, SRj, NHCO2(C1-4 alkyl), NHSO2(C1-4 alkyl), and a 4- to 6-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, NRe, O, and S.

### Claim 4 (depends on 3)

A compound according to claim 3, wherein the compound is of Formula (II):
or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 4)

A compound according to claim 4, wherein:
R1 is independently selected from the group consisting of: C1-6 alkyl, C3-6 cycloalkyl, —CONHC4-18 alkyl, —CONHC2-8 haloalkyl, —CONH(CH2)1-8 Ph, —(CH2)m-(phenyl substituted with 1 Rb and 0-2 Rg), and a 5- to 6-membered heteroaryl substituted with 0-1 Rb and 0-2 Rg, wherein said heteroaryl is selected from: pyridyl, oxazolyl, thiazolyl and
R2 is independently selected from the group consisting of: C1-4 alkyl and C1-4 haloalkyl;
R3 is independently selected from the group consisting of: H and F;
R4 is independently selected from the group consisting of: H and F;
R6 is independently Rc or —(CH2)n—(X)t—(CH2)mRc;
R11 and R15 are independently selected from the group consisting of: H, C1-4 alkyl and halo;
R12 and R14 are independently selected from the group consisting of: H, halo, C1-4 alkyl and C1-4 alkoxy;
R13 is independently selected from the group consisting of: H, halo, C1-4 alkyl substituted with 0-1 C1-4 alkoxy, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, —(CH2)m—C3-4 cycloalkyl, CN, N(C1-4 alkyl)2, NHCO2(C1-4 alkyl), NHSO2(C1-4 alkyl), pyrazolyl, and morpholinyl;
alternatively, R12 and R13, together with the carbon atoms to which they are attached, combine to form a 5- to 6-membered carbocyclic ring or a 5- to 6-membered heterocyclic ring comprising: carbon atoms and 1-3 heteroatoms selected from N, NRe, O, and S;
Rb is, at each occurrence, independently selected from the group consisting of: halo, OH, C1-8 alkyl, C1-8 alkoxy, C1-8 haloalkyl, C1-10 haloalkoxy, —O(CH2)sO(C1-6 alkyl), N(C1-4 alkyl)2, —CONH(CH2)6-20H, —(CH2)m(C3-6 cycloalkyl), —(CH2)m(C4-6 cycloalkenyl), —O(CH2)m(C3-6 cycloalkyl), 4-C1-4 alkoxy-Ph, —O(CH2)mPh, morpholinyl, pyridyl, 2-C1-4 alkoxy-pyridin-5-yl, pyrimidinyl, pyrazinyl, and —O-pyrimidinyl;
Rg is, at each occurrence, independently selected from the group consisting of: halo, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, and C1-4 haloalkoxy;
m, at each occurrence, is independently 0, 1, 2 or 3; and
s, at each occurrence, is independently 1, 2, or 3.

### Claim 6 (depends on 5)

A compound according to claim 5, wherein:
R1 is independently selected from the group consisting of: C1-6 alkyl, —CONHC4-18 alkyl, —CONH(CH2)1-8Ph, and
R6 is independently Rc, ORc, —CONHRc, or —NHCORc;
R12 is independently selected from the group consisting of: H, halo, C1-4 alkyl and C1-4 alkoxy;
R13 is independently selected from the group consisting of: H, halo, C1-4 alkyl substituted with 0-1 C1-4 alkoxy, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, —(CH2)m—C3-4 cycloalkyl, CN, N(C1-4 alkyl)2, NHCO2(C1-4 alkyl), NHSO2(C1-4 alkyl), pyrazolyl, and morpholinyl;
alternatively, R12 and R13, together with the carbon atoms to which they are attached, combine to form a 5- to 6-membered carbocyclic ring or a 5- to 6-membered saturated heterocyclic ring comprising: carbon atoms and 1-2 oxygen atoms;
R14 is independently selected from the group consisting of: H and C1-4 alkoxy;
Rb is, at each occurrence, independently selected from the group consisting of: halo, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-10 haloalkoxy, —O(CH2)sO(C1-6 alkyl), —CONH(CH2)6-20H, —(CH2)m(C3-6 cycloalkyl), —(CH2)m(C4-6 cycloalkenyl), —O(CH2)m(C3-6 cycloalkyl), phenoxy, benzoxy, morpholinyl, 2-C1-4 alkoxy-pyridin-5-yl, pyrimidin-5-yl, pyrazin-2-yl and —O-pyrimidinyl; and
Rc is, at each occurrence, independently selected from the group consisting of: C3-6 cycloalkyl substituted with 0-2 Rd, —(CH2)m-(phenyl substituted with 0-3 Rd), and a heteroaryl selected from: oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, oxadiazolyl, triazolyl, tetrazolyl, pyridyl, and pyrazinyl; wherein said heteroaryl is substituted with 0-2 Rd.

### Claim 7 (depends on 6)

A compound according to claim 6, wherein:
R1 is
R6 is independently selected from the group consisting of: OPh, —CONH(C3-6 cycloalkyl), —CONHPh, —CONH-(2-halo-Ph), —CONH-(3-halo-Ph), —CONH-(4-halo-Ph), —CONH-(4-C1-4 alkyl-Ph), —CONH(4-OH-Ph), —CONH-(3-C1-4 alkoxy-Ph), —CONH-(4-C1-4 alkoxy-Ph), —CONH-(4-C1-4 haloalkyl-Ph), —CONH-(4-C1-4 haloalkoxy-Ph), —CONH-(4-CN-Ph), —CONH-(4-tetrazolyl-Ph), —CONH-(3-halo-4-C1-4 alkyl-Ph), —CONH-(3-halo-4-C1-4 alkoxy-Ph), —CONH(CH2)2Ph, —CONH(4-(4-C1-4 alkoxy-Ph)-thiazol-2-yl), —CONH(1-C1-4 alkyl-pyrazol-3-yl), —CONH(5-C1-4 alkoxy-pyrid-2-yl), —CONH(6-C1-4 alkoxy-pyrid-3-yl), —CONH(5-C1-4 alkoxy-pyrazin-2-yl), —CONH(6-C1-4 alkoxy-pyridazin-3-yl), —NHCO(CH2)SO2(C1-4 alkyl), —NHCOPh, —NHCO(2-C1-4 alkyl-Ph), —NHCO(3-C1-4 alkyl-Ph), —NHCO(4-C1-4 alkyl-Ph), —NHCO(2-halo-Ph), —NHCO(3-halo-Ph), —NHCO(2-C1-4 haloalkyl-Ph), —NHCO(2-C1-4 haloalkoxy-Ph), —NHCO(2-halo-4-halo-Ph), —NHCO(2-halo-5-halo-Ph), —NHCO(oxazolyl), —NHCO(isoxazolyl), —NHCO(3-C1-4 alkyl-isoxazol-5-yl), —NHCO(4-C1-4 alkyl-isoxazol-5-yl), —NHCO(3-C1-4 alkoxy-isoxazol-5-yl), —NHCO(4-C1-4 alkoxy-isoxazol-5-yl), —NHCO(3-halo-isoxazol-5-yl), —NHCO(3-OBn-isoxazol-5-yl), —NHCO(3-(2-halo-Ph)-isoxazol-5-yl), —NHCO(3-(3-halo-Ph)-isoxazol-5-yl), —NHCO(5-C1-4 alkyl-1H-pyrazol-3-yl), imidazolyl, —NHCO(5-C1-4 alkyl-1,3,4-oxadiazol-2-yl), —NHCO(1-C1-4 alkyl-1,2,3-triazol-4-yl), —NHCO(6-C1-4 alkoxy-pyrid-3-yl), —NHCO(pyrazinyl), —NHCO(6-halo-pyridazin-3-yl), 5-C1-4 haloalkyl-1,3,4-oxadiazol-2-yl, 3-NO2-1H-1,2,4-triazol-1-yl, tetrazolyl and 5-C1-4 alkyl-tetrazol-1-yl;
Rb is independently selected from the group consisting of: halo, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-8 haloalkoxy, —CONH(CH2)6-20H, C3-6 cycloalkyl, C4-6 cycloalkenyl, —O(CH2)m(C3-6 cycloalkyl), phenoxy, benzoxy, pyrimidinyl, pyrazinyl and —O-pyrimidinyl; and
Rg is independently selected from the group consisting of: halo and C1-4 alkyl.

### Claim 8 (depends on 7)

A compound according to claim 7, wherein:
R2 is independently selected from the group consisting of: CF3 and Me;
R3 is independently selected from the group consisting of: H and F;
R4 is independently selected from the group consisting of: H and F;
R6 is independently selected from the group consisting of: OPh, —CONH(cyclopropyl), —CONH(cyclobutyl), —CONH(cyclopentyl), —CONH(cyclohexyl), —CONHPh, —CONH(4-F-Ph), —CONH(2-Cl-Ph), —CONH(4-Cl-Ph), —CONH(4-Me-Ph), —CONH(4-OH-Ph), —CONH(3-OMe-Ph), —CONH(4-OMe-Ph), —CONH(4-CF3-Ph), —CONH(4-OCF3-Ph), —CONH(1-Me-pyrazol-3-yl), —CONH(4-(1H-tetrazol-2-yl)-Ph), —CONH(4-(2H-tetrazol-5-yl)-Ph), —CONH(3-F-4-Me-Ph), —CONH(3-F-4-OMe-Ph), —CONH(CH2)2Ph, —CONH(5-OMe-pyrid-2-yl), —CONH(6-OMe-pyrid-3-yl), —CONH(5-OMe-pyrazin-2-yl), —CONH(6-OMe-pyridazin-3-yl), —NHCO(CH2)SO2Me, —NHCOPh, —NHCO(2-Me-Ph), —NHCO(3-Me-Ph), —NHCO(4-Me-Ph), —NHCO(2-Cl-Ph), —NHCO(3-Cl-Ph), —NHCO(2-C1-4—F-Ph), —NHCO(2-C1-5—F-Ph), —NHCO(isoxazol-5-yl), —NHCO(3-Me-isoxazol-5-yl), —NHCO(4-Me-isoxazol-5-yl), —NHCO(3-OMe-isoxazol-5-yl), —NHCO(3-Br-isoxazol-5-yl), —NHCO(3-(2-Cl-Ph)-isoxazol-5-yl), —NHCO(3-(3-F-Ph)-isoxazol-5-yl), —NHCO(3-OBn-isoxazol-5-yl), 1H-imidazol-1-yl, —NHCO(5-Me-1,3,4-oxadiazol-2-yl), —NHCO(1-Me-1,2,3-triazol-4-yl), —NHCO(6-OMe-pyrid-3-yl), —NHCO(6-Cl-pyridazin-3-yl), 5-CF3-1,3,4-oxadiazol-2-yl, 1H-tetrazol-1-yl, 1H-tetrazol-3-yl, and 2H-tetrazol-5-yl;
R11 and R15 are independently selected from the group consisting of: H, Me, F, and Cl;
R12 is independently selected from the group consisting of: H, F, Cl, Me and OMe;
R13 is independently selected from the group consisting of: H, F, Cl, Br, Me, OMe, OEt, CH2OMe, CF3, CH2CF3, OCHF2, OCF3, CN, N(Me)2, cyclopropyl and cyclopropylmethyl;
alternatively, R12 and R13, together with the carbon atoms to which they are attached, combine to form a 5- to 6-membered carbocyclic ring or a 5- to 6-membered saturated heterocyclic ring comprising: carbon atoms and 1-2 oxygen atoms;
R14 is H;
Rb is, at each occurrence, independently selected from the group consisting of: n-pentyl, methoxy, n-butoxy, i-butoxy, i-pentoxy, —O(CH2)1-6CF3, —O(CH2)1-4CF2CF3, —CONH(CH2)6-20H, cyclopropyl, cyclopent-1-en-1-yl, cyclohex-1-en-1-yl, —O(CH2)2(cyclopentyl), phenoxy, benzoxy, pyrimidin-5-yl, pyrazin-2-yl and —O-pyrimidin-2-yl; and
Rg is F.

### Claim 9 (depends on 6)

A compound according to claim 6, wherein:
R13 is independently selected from the group consisting of: H, halo, C1-4 alkyl substituted with 0-1 C1-4 alkoxy, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, CN or C3-4 cycloalkyl.

### Claim 10 (depends on 9)

A compound according to claim 9, wherein:
R1 is independently

### Claim 11 (depends on 10)

A compound according to claim 10, wherein:
Rb is independently selected from: —O(CH2)1-6CF3, and —O(CH2)1-4CF2CF3.

### Claim 12 (depends on 11)

A compound according to claim 11, wherein:
R6 is independently 5-membered nitrogen heteroaryl.

### Claim 13 (depends on 12)

A compound according to claim 12, wherein:
R6 is independently 1H-imidazol-1-yl, 1H-tetrazol-1-yl, 1H-tetrazol-3-yl, or 2H-tetrazol-5-yl.

### Claim 14

A compound selected from:
or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof.

### Claim 15 (depends on 1)

A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a compound of claim 1, or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof.

### Claim 16 (depends on 15)

The pharmaceutical composition according to claim 15, further comprising one or more other suitable therapeutic agents selected from: anti-diabetic agents, anti-hyperglycemic agents, anti-hyperinsulinemic agents, anti-retinopathic agents, anti-neuropathic agents, anti-nephropathic agents, anti-atherosclerotic agents, anti-ischemic agents, anti-hypertensive agents, anti-obesity agents, anti-dyslipidemic agents, anti-hyperlipidemic agents, anti-hypertriglyceridemic agents, anti-hypercholesterolemic agents, anti-restenotic agents, lipid lowering agents, anorectic agents, and appetite suppressants.

### Claim 17 (depends on 1)

A method for the treatment of diabetes, hyperglycemia, impaired glucose tolerance, gestational diabetes, insulin resistance, hyperinsulinemia, nonalcoholic fatty liver disease, nonalcoholic steatohepatitis, retinopathy, neuropathy, nephropathy, delayed wound healing, Metabolic Syndrome, obesity, dyslipidemia, and glaucoma, comprising administering to a patient in need of such treatment a therapeutically effective amount of at least a compound of claim 1.