Spiroketone acetyl-CoA carboxylase inhibitors

A technology of alkyl and phenyl, applied in the field of 1'-spiro[benzopyran-2

Inactive Publication Date: 2009-09-23
PFIZER PRODS ETAT DE CONNECTICUT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Currently, no ACC1 or ACC2 inhibitors are used as weight loss drugs

Method used

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  • Spiroketone acetyl-CoA carboxylase inhibitors
  • Spiroketone acetyl-CoA carboxylase inhibitors
  • Spiroketone acetyl-CoA carboxylase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0091] The examples set forth herein below are for illustrative purposes only. The compositions, methods, and various parameters described herein are merely illustrative of various aspects and embodiments of the invention and are not intended to limit the scope of the invention as claimed in any way.

[0092] All reactants were obtained from commercial sources unless otherwise stated.

[0093] Flash chromatography was performed according to the method described by Still et al., J. Org. Chem., 1978, 43, 2923.

[0094] Use 40M or 40S Biotage with KP-SIL silica (40-63 μM, 60 Å) Columns (Bioatge AB; Uppsala, Sweden) were used for all Biotage described herein purification.

[0095] Fill RediSep with Columns of silica utilizing CombiFlash Companion systems (Teledyne Isco; Lincoln, Nebraska) performed all Combiflashes described herein purification.

[0096] Mass spectra were recorded on a Waters (Waters Corp.; Milford, MA) Micromass Platform II spectrometer. Mass spectra w...

Embodiment B1-B14

[0428]

[0429] Ex.

square

Law

R 1

R 2

R 3

R 4

ACC1

IC 50

(nM)

ACC1

n *

ACC2

IC 50

(nM)

ACC2

n *

MS(ACPI)

m / z

(M+H) +

HPLC

RT

(min)

B1

B

H

CH 3

CH 3

H

24.1

1

424

2.3

B2

B

H

OCH(CH 3 ) 2

H

H

16.1

1

31.1

1

454

2.5

B3

B

H

OCH 2 CH 3

H

H

21.4

1

34.3

1

440

2.4

B4

B

H

Cl

CH 3

H

56.8

2

127

1

444

2.5

B5

B

H

OCH 3

H

H

81.0

1

231

1

426

2.3

B6

B

OCH 3

H

H

H

109

1

426

1.9

B7 ...

Embodiment C1-C5

[0446]

[0447] Ex.

method

R1

R2

R3

R4

ACC1

IC 50

(nM)

ACC1

n *

MS(ACPI)

m / z(M+H) +

HPLC

RT

(min)

C1

B

H

CH 3

CH 3

H

17.5

2

418

2.5

C2

B

H

OCH 3

H

H

22.6

2

420

2.2

[0448] C3

B

OCH 3

H

CH 3

H

29.5

2

434

2.2

C4

B

H

C1

CH 3

H

30.6

2

438

2.7

C5

B

H

CO(O)CH 3

H

H

49.8

2

448

2.3

[0449] * -n is the number of times the trial is performed.

[0450] Ex.C1: 1'-[(7-ethyl-1H-indazol-5-yl)carbonyl]-6,7-dimethylspiro[benzopyran-2,4'-piperidine]- 4(3H)-ketone.

[0451] Ex.C2: 1'-[(7-ethyl-1H-indazol-5-yl)carbonyl]-6-methoxyspir...

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PUM

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Abstract

The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R, R, R, R, R, R, R, R and R are as described herein; pharmaceutical compositions thereof; and the use thereof in treating mammals suffering from the condition of being overweight.

Description

technical field [0001] The present invention relates to a substituted 1'-(benzoyl)spiro[benzopyran-2,4'-piperidin]-4(3H)-one compound as acetyl-CoA carboxylase and the present invention relates to the use of the above compounds in the treatment of obesity. Background technique [0002] Obesity is a major disease in the United States and other countries. Complications include hypertension that significantly reduces life expectancy, diabetes, coronary heart disease, stroke, congestive heart failure, venous disease, multiple orthopaedic diseases, and pulmonary insufficiency. Various medical treatments, including diet therapy, psychotherapy, drug therapy, and behavioral therapy, have yielded very poor results in multiple trials. Several surgical treatments have been tried that reduce the absorption area of ​​the small intestine or aim to reduce the size of the stomach by segmentation or bypass. Performing these procedures in morbidly obese patients has been shown not only to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107A61K31/39A61P5/00
CPCC07D491/107A61P35/00A61P3/04A61P3/06A61P43/00A61P5/00A61P9/00A61P9/04A61P9/10A61P3/10C07D491/10A61K31/39
Inventor 杰弗里·维恩·克比特理查德·路易斯·埃利欧特安德鲁·西蒙·柏尔
Owner PFIZER PRODS ETAT DE CONNECTICUT
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