IP Library Patent Application 15768880
Patent Application
App. No. 15/768,880

ARYL SULFONAMIDES AS BLT1 ANTAGONISTS

Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US None
App. No.
15/768,880
Abstract

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are antagonists of leukotriene B 4 receptor 1 (BLT1) and may be useful in the treatment, prevention and suppression of diseases mediated by the leukotriene B 4 receptor 1 (BLT1). The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, insulin resistance, hyperglycemia, dyslipidemia, lipid disorders, obesity, hypertension, Non-alcoholic fatty liver disease/nonalcoholic steatohepatitis, metabolic syndrome, atherosclerosis, and cancer.

Claims (201)

1 . A compound of structural formula I:

or a pharmaceutically acceptable salt thereof, wherein

A is selected from the group consisting of:

(1) aryl, and

(2) heteroaryl,

wherein aryl and heteroaryl are unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl, C 3-6 cycloalkyl, and halogen;

B is selected from the group consisting of:

(1) aryl, and

(2) heteroaryl,

wherein aryl is unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl, halogen and CF 3 , and wherein heteroaryl is unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl, halogen, and CF 3 ;

X is selected from the group consisting of:

(1) —NHSO 2 CF 3 ,

(2) —NHSO 2 CH 2 CF 3 ,

(3) —NHSO 2 CHF 2 ,

(4) —NHSO 2 C 1-6 alkyl,

(5) —NHSO 2 CH 2 C 3-6 cycloalkyl, and

(6) —NHSO 2 C 3-6 cycloalkyl,

wherein alkyl and cycloalkyl are unsubstituted or substituted with 1-3 substituents independently selected from C 1-6 alkyl;

Z is selected from the group consisting of:

(1) hydrogen,

(2) C 1-6 alkyl, and

(3) phenyl,

wherein alkyl and phenyl are unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl;

R a is selected from the group consisting of:

(1) hydrogen,

(2) halogen, and

(3) C 1-6 alkyl; and

R b is selected from the group consisting of:

(1) hydrogen,

(2) halogen, and

(3) C 1-6 alkyl.

2 . The compound according to claim 1 wherein Z is hydrogen or —C 1-6 alkyl; or a pharmaceutically acceptable salt thereof.

3 . The compound according to claim 1 wherein Z is phenyl, wherein phenyl is unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl; or a pharmaceutically acceptable salt thereof.

4 . The compound according to claim 1 wherein X is selected from the group consisting of:

(1) —NHSO 2 CF 3 ,

(2) —NHSO 2 CH 2 CF 3 ,

(3) —NHSO 2 CHF 2 ,

(4) —NHSO 2 C 1-6 alkyl, and

(5) —NHSO 2 C 3-6 cycloalkyl,

wherein alkyl and cycloalkyl are unsubstituted or substituted with 1-3 substituents independently selected from C 1-6 alkyl; or a pharmaceutically acceptable salt thereof.

5 . The compound according to claim 1 wherein X is —NHSO 2 CF 3 ; or a pharmaceutically acceptable salt thereof.

6 . The compound according to claim 1 wherein A is selected from the group consisting of:

(1) phenyl, and

(2) heteroaryl,

wherein phenyl and heteroaryl are unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl, C 3-6 cycloalkyl, and halogen; or a pharmaceutically acceptable salt thereof.

7 . The compound according to claim 1 wherein A is phenyl, wherein phenyl is unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl, C 3-6 cycloalkyl and halogen; or a pharmaceutically acceptable salt thereof.

8 . The compound according to claim 1 wherein A is heteroaryl, wherein heteroaryl is unsubstituted or substituted with 1-3 substituents independently selected from C 1-6 alkyl, C 3-6 cycloalkyl and halogen; or a pharmaceutically acceptable salt thereof.

9 . The compound according to claim 1 wherein A is selected from the group consisting of:

(1) pyrazole,

(2) pyridine,

(3) thiophene,

(4) thiazole,

(5) benzothiophene,

(6) triazole,

(7) oxazole,

(8) pyrazine,

(9) thiadiazole, and

(10) pyridazine,

wherein pyrazole, pyridine, thiophene, thiazole, benzothiophene, triazole, oxazole, pyrazine, thiadiazole, and pyridazine are unsubstituted or substituted with 1-3 substituents independently selected from C 1-6 alkyl, C 3-6 cycloalkyl, and halogen; or a pharmaceutically acceptable salt thereof.

10 . The compound according to claim 1 wherein A is pyridine; or a pharmaceutically acceptable salt thereof.

11 . The compound according to claim 1 wherein B is selected from the group consisting of:

(1) phenyl,

(2) pyrazine,

(3) pyridine, and

(4) pyridazine,

wherein phenyl is unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl, halogen and CF 3 , and wherein pyrazine, pyridine and pyridazine are unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl, halogen, and CF 3 ; or a pharmaceutically acceptable salt thereof.

12 . The compound according to claim 1 wherein B is phenyl; or a pharmaceutically acceptable salt thereof.

13 . The compound according to claim 1 wherein B is pyridine, wherein pyridine is unsubstituted or substituted with 1-3 substituents independently selected from halogen; or a pharmaceutically acceptable salt thereof.

14 . The compound according to claim 1 wherein R a and R b are independently selected from the group consisting of: hydrogen, and C 1-6 alkyl; or a pharmaceutically acceptable salt thereof.

15 . The compound according to claim 1 wherein R a and R b are hydrogen; or a pharmaceutically acceptable salt thereof.

16 . The compound according to claim 1 wherein

A is selected from the group consisting of:

(1) phenyl, and

(2) heteroaryl,

wherein phenyl and heteroaryl are unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl, C 3-6 cycloalkyl, and halogen;

B is selected from the group consisting of:

(1) phenyl,

(2) pyrazine,

(3) pyridine, and

(4) pyridazine,

wherein pyrazine, pyridine and pyridazine are unsubstituted or substituted with 1-3 substituents independently selected from C 1-6 alkyl, halogen, and CF 3 ;

X is selected from the group consisting of:

(1) —NHSO 2 CF 3 ,

(2) —NHSO 2 CH 2 CF 3 ,

(3) —NHSO 2 CHF 2 ,

(4) —NHSO 2 C 1-6 alkyl, and

(5) —NHSO 2 C 3-6 cycloalkyl,

wherein alkyl and cycloalkyl are unsubstituted or substituted with 1-3 substituents independently selected from C 1-6 alkyl;

Z is selected from the group consisting of:

(1) hydrogen, and

(2) phenyl,

wherein phenyl is unsubstituted or substituted with 1-4 substituents independently selected from C 1-6 alkyl; and

R a and R b are independently selected from the group consisting of: hydrogen, and C 1-6 alkyl;

or a pharmaceutically acceptable salt thereof.

17 . The compound according to claim 1 wherein

A is heteroaryl;

B is phenyl;

X is —NHSO 2 CF 3 ;

Z is hydrogen; and

R a and R b are hydrogen;

or a pharmaceutically acceptable salt thereof.

18 . The compound according to claim 21 selected from:

(1) N-(2-((3,4-Rac-cis)-3-benzyl-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(2) N-(2-((3,4-Rac-trans)-3-benzyl-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(3) N-(2-((3,4-Rac-cis)-3-([1,1′-biphenyl]-4-ylmethyl)-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(4) N-(2-((3,4-Rac-trans)-3-([1,1′-biphenyl]-4-ylmethyl)-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(5) 1,1,1-Trifluoro-N-(2-((3,4-rac-trans)-4-hydroxy-3-((5-phenylthiophen-2-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(6) N-(2-((3,4-Rac-trans)-3-((1H-pyrazol-3-yl)methyl)-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(7) 1,1,1-Trifluoro-N-(2-((3,4-rac-trans)-4-hydroxy-3-(pyridin-3-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(8) 1,1,1-Trifluoro-N-(2-((3,4-rac-trans)-4-hydroxy-3-(thiophen-3-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(9) 1,1,1-Trifluoro-N-(2-((3,4-rac-trans)-4-hydroxy-3-(thiazol-5-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(10) 1,1,1-Trifluoro-N-(2-((3,4-rac-cis)-4-hydroxy-3-(thiazol-5-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(11) 1,1,1-Trifluoro-N-(2-((3,4-rac-trans)-4-hydroxy-3-((5-methylpyridin-2-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(12) N-(2-((3,4-Rac-trans)-3-((1H-pyrazol-4-yl)methyl)-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(13) 1,1,1-Trifluoro-N-(2-((3,4-rac-trans)-4-hydroxy-3-((1-methyl-1H-pyrazol-5-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(14) 1,1,1-Trifluoro-N-(2-{(rac-trans)-4-hydroxy-3-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(15) 1,1,1-Trifluoro-N-{2-[(rac-trans)-4-hydroxy-3-(1,3-oxazol-2-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methanesulfonamide;

(16) 1,1,1-Trifluoro-N-(2-{(rac-trans)-4-hydroxy-3-[(2-methyl-1,3-thiazol-4-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(17) N-(2-{(rac-trans)-3-[(2-cyclopropyl-1,3-thiazol-4-yl)methyl]-4-hydroxy-3,4-dihydro-2H-chromen-7-yl}phenyl)-1,1,1-trifluoromethanesulfonamide;

(18) 1,1,1-Trifluoro-N-(2-{(rac-trans)-4-hydroxy-3-[(1-methyl-1H-pyrazol-3-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(19) 1,1,1-Trifluoro-N-(2-{(rac-trans)-3-[(3-fluoropyridin-2-yl)methyl]-4-hydroxy-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(20) 1,1,1-Trifluoro-N-(2-{(rac-trans)-4-hydroxy-3-[(6-methylpyridin-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(21) 1,1,1-Trifluoro-N-(2-{(rac-trans)-4-hydroxy-3-[(3-methylpyridin-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(22) 1,1,1-Trifluoro-N-(2-{(rac-trans)-4-hydroxy-3-[(5-methyl-1,3-thiazol-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(23) 1,1,1-Trifluoro-N-(2-{(rac-trans)-4-hydroxy-3-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(24) 1,1,1-Trifluoro-N-(2-((rac-trans)-4-hydroxy-3-((2-phenylthiazol-4-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(25) 1,1,1-trifluoro-N-{2-[(3R,4S)-4-hydroxy-3-(pyridin-4-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methanesulfonamide;

(26) 1,1,1-trifluoro-N-{2-[(3 S,4R)-4-hydroxy-3-(pyridin-4-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methanesulfonamide;

(27) 1,1,1-Trifluoro-N-{2-[(rac-trans)-4-hydroxy-3-(pyrazin-2-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methanesulfonamide;

(28) 1,1,1-Trifluoro-N-{2-[(rac-trans)-4-hydroxy-3-(pyridazin-3-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methane-sulfonamide;

(29) 1,1,1-Trifluoro-N-(2-((rac-trans)-3-((5-fluoropyridin-2-yl)methyl)-4-hydroxychroman-7-yl)phenyl)methanesulfonamide;

(30) N-(2-((3,4-Rac-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(31) 1,1,1-trifluoro-N-(2-(3,4-rac-cis)-4-hydroxy-3-(thiazol-4-ylmethyl)chroman-7-yl)phenyl)metha-nesulfonamide;

(32) 1,1,1-trifluoro-N-(2-((3,4-rac-trans)-4-hydroxy-3-(thiazol-4-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(33) 1,1,1-Trifluoro-N-(2-((3,4-rac-trans)-4-hydroxy-3-(thiophen-2-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(34) N-(2-((3,4-rac-trans)-3-(benzo[b]thiophen-2-ylmethyl)-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(35) 1,1,1-Trifluoro-N-(2-((rac-trans)-4-hydroxy-3-((1-methyl-3-phenyl-1H-pyrazol-5-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(36) 1,1,1-Trifluoro-N-(2-((3S,4R)-4-hydroxy-3-((1-methyl-3-phenyl-1H-pyrazol-5-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(37) 1,1,1-Trifluoro-N-(2-((3R,4S)-4-hydroxy-3-((1-methyl-3-phenyl-1H-pyrazol-5-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(38) 1,1,1-Trifluoro-N-(2-((rac-trans)-4-hydroxy-3-((5-phenylpyridin-2-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(39) (2-((3S,4R)-4-hydroxy-3-((5-phenylpyridin-2-yl)methyl)chroman-7-yl)phenyl)((trifluoromethyl)sulfonyl)amide;

(40) (2-((3R,4S)-4-hydroxy-3-((5-phenylpyridin-2-yl)methyl)chroman-7-yl)phenyl)((trifluoromethyl)sulfonyl)amide;

(41) 1,1,1-Trifluoro-N-(2-((rac-trans)-4-hydroxy-3-((2-phenylthiazol-5-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(42) 1,1,1-Trifluoro-N-(2-((3S,4R)-4-hydroxy-3-((2-phenylthiazol-5-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(43) 1,1,1-Trifluoro-N-(2-((3R,4S)-4-hydroxy-3-((2-phenylthiazol-5-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(44) 1,1,1-Trifluoro-N-(2-((3,4-trans)-3-((5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)methyl)-4-hydroxychroman-7-yl)phenyl)methanesulfonamide;

(45) N-(2-((3,4-trans)-3-((2-(tert-butyl)thiazol-4-yl)methyl)-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(46) N-(2-((3S,4R)-3-((1-ethyl-1H-pyrazol-3-yl)methyl)-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(47) N-(2-((3R,4S)-3-((1-ethyl-1H-pyrazol-3-yl)methyl)-4-hydroxychroman-7-yl)phenyl)-1,1,1-trifluoromethanesulfonamide;

(48) 1,1,1-Trifluoro-N-(2-((rac-trans)-4-hydroxy-3-((1-phenyl-1H-pyrazol-5-yl)methyl)chroman-7-yl)phenyl)methanesulfonamide;

(49) (2-((3,4-trans)-4-hydroxy-3-((1-phenyl-1H-pyrazol-5-yl)methyl)chroman-7-yl)phenyl)((trifluoromethyl)sulfonyl)amide;

(50) 1,1,1-trifluoro-N-{2-[(3R,4S)-4-hydroxy-3-(1,3-thiazol-4-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}-methanesulfonamide;

(51) 1,1,1-trifluoro-N-{2-[(3S,4R)-4-hydroxy-3-(1,3-thiazol-4-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}-methanesulfonamide;

(52) 1,1,1-trifluoro-N-(2-{(3S,4R)-4-hydroxy-3-[(5-methyl-1,3-thiazol-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(53) 1,1,1-trifluoro-N-(2-{(3R,4S)-4-hydroxy-3-[(5-methyl-1,3-thiazol-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(54) 1,1,1-trifluoro-N-{2-[(3 S,4R)-4-hydroxy-3-(pyridin-2-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}-methanesulfonamide;

(55) 1,1,1-trifluoro-N-{2-[(3R,4S)-4-hydroxy-3-(pyridin-2-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}-methanesulfonamide;

(56) 1,1,1-Trifluoro-N-(2-{(3R,4S)-4-hydroxy-3-[(2-methyl-1,3-thiazol-4-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)-methanesulfonamide;

(57) 1,1,1-Trifluoro-N-(2-{(3S,4R)-4-hydroxy-3-[(2-methyl-1,3-thiazol-4-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)-methanesulfonamide;

(58) N-{2-[(3R,4S)-3-benzyl-4-hydroxy-3,4-dihydro-2H-chromen-7-yl]phenyl}-1,1,1-trifluoromethanesulfonamide;

(59) N-{2-[(3S,4R)-3-benzyl-4-hydroxy-3,4-dihydro-2H-chromen-7-yl]phenyl}-1,1,1-trifluoromethanesulfonamide;

(60) 1,1,1-Trifluoro-N-(2-{(3,4-trans)-4-hydroxy-3-[(3-methylpyridin-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(61) 1,1,1-trifluoro-N-{2-[(3R,4S)-4-hydroxy-3-(thiophen-2-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methanesulfonamide;

(62) 1,1,1-trifluoro-N-{2-[(3 S,4R)-4-hydroxy-3-(thiophen-2-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methanesulfonamide;

(63) 1,1,1-Trifluoro-N-(2-{(3,4-trans)-4-hydroxy-3-[(6-methyl-pyridin-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl}-phenyl)methanesulfonamide;

(64) 1,1,1-Trifluoro-N-(2-((3R,4S)-4-hydroxy-3-((2-phenylthiazol-4-yl)-methyl)chroman-7-yl)-phenyl)methanesulfonamide;

(65) 1,1,1,-Trifluoro-N-(2-((3S,4R)-4-hydroxy-3-((2-phenylthiazol-4-yl)-methyl)chroman-7-yl)-phenyl)methanesulfonamide;

(66) 1,1,1-trifluoro-N-(2-{(3,4-trans)-4-hydroxy-3-[(1-methyl-1H-pyrazol-5-yl)methyl]-3,4-di-hydro-2H-chromen-7-yl}-phenyl)methanesulfonamide;

(67) N-{2-[(3S,4R)-3-(biphenyl-4-ylmethyl)-4-hydroxy-3,4-dihydro-2H-chromen-7-yl]phenyl}- 1 , 1 , 1 -trifluoromethanesulfonamide;

(68) N-{2-[(3R,4S)-3-(biphenyl-4-ylmethyl)-4-hydroxy-3,4-dihydro-2H-chromen-7-yl]phenyl}- 1 , 1 , 1 -trifluoromethanesulfonamide;

(69) 1,1,1-Trifluoro-N-(2-{(3,4-trans)-3-[(3-fluoropyridin-2-yl)methyl]-4-hydroxy-3,4-dihydro-2H-chromen-7-yl}phenyl)methanesulfonamide;

(70) 1,1,1-Trifluoro-N-(2-{(3,4-trans)-4-hydroxy-3-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-3,4-dihydro-2H-chromen-7-yl)}phenyl)-methanesulfonamide;

(71) 1,1,1-trifluoro-N-{2-[(3,4-trans)-4-hydroxy-3-(1H-pyrazol-3-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}-methanesulfonamide;

(72) N-{2-[(3S,4R)-4-hydroxy-3-(pyridin-2-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methanesulfonamide;

(73) N-{2-[(3R,4S)-4-hydroxy-3-(pyridin-2-ylmethyl)-3,4-dihydro-2H-chromen-7-yl]phenyl}methanesulfonamide;

(74) 1,1,1-Trifluoro-N-(3-((3,4-rac-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyrazin-2-yl)methanesulfonamide;

(75) N-(2-((3,4-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)phenyl)-1-methylcyclopropane-1-sulfonamide;

(76) 2,2,2-Trifluoro-N-(3-((3,4-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyrazin-2-yl)ethanesulfonamide;

(77) 2,2,2-Trifluoro-N-(3-((3R,4S)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridin-2-yl)ethanesulfonamide;

(78) 2,2,2-Trifluoro-N-(3-((3S,4R)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridin-2-yl)ethanesulfonamide;

(79) 2,2,2-Trifluoro-N-(2-((3R,4S)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)phenyl)ethanesulfonamide;

(80) 2,2,2-Trifluoro-N-(2-((3S,4R)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)phenyl)ethanesulfonamide;

(81) 1,1-Difluoro-N-(2-((3R,4S)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(82) 1,1-Difluoro-N-(2-((3S,4R)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(83) 1,1,1-Trifluoro-N-(4-fluoro-2-((3,4-trans)-4-hy droxy-3-(pyridin-2-ylmethyl)chroman-7-yl)phenyl)methanesulfonamide;

(84) 1,1,1-Trifluoro-N-(5-fluoro-3-((3,4-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridin-2-yl)methanesulfonamide;

(85) 1,1,1-Trifluoro-N-(5-fluoro-3-((3,4-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridin-2-yl)methanesulfonamide;

(86) 1,1-Difluoro-N-(3-((3,4-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridin-2-yl)methanesulfonamide;

(87) 1,1,1-Trifluoro-N-(3-((3,4-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridin-2-yl)methanesulfonamide;

(88) 2,2,2-Trifluoro-N-(3-((3,4-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)-5-(trifluoromethyl)pyrazin-2-yl)ethanesulfonamide;

(89) N-(6-chloro-4-((3R,4S)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridazin-3-yl)-1,1,1-trifluoromethanesulfonamide;

(90) N-(4-((3,4-trans)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridazin-3-yl)-1,1,1-trifluoro-methanesulfonamide;

(91) N-(6-chloro-4-((3S,4R)-4-hydroxy-3-(pyridin-2-ylmethyl)chroman-7-yl)pyridazin-3-yl)-1,1,1-trifluoromethanesulfonamide;

(92) 1,1,1-Trifluoro-N-(2-((3R,4S)-4-hydroxy-3-(1-(2-phenylthiazol-4-yl)ethyl)chroman-7-yl)phenyl)methanesulfonamide; and

(93) 1,1,1-trifluoro-N-(4-fluoro-2-(4-hydroxy-3-(1-(pyridin-2-yl)ethyl)chroman-7-yl)phenyl)methanesulfonamide;

or a pharmaceutically acceptable salt thereof.

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

20 . (canceled)

21 . (canceled)

22 . A method of treating or preventing a disorder, condition or disease that may be responsive to the antagonism of the BLT1 receptor in a patient in need thereof comprising administration of a therapeutically effective amount of a compound according to claim 1 .

23 . A method of treating type 2 diabetes mellitus in a patient in need of treatment comprising the administration to the patient of a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2018
From: HAN, YONGXIN; LIM, JONGWON; SILIPHAIVANH, PHIENG; SPENCER, KERRIE
To: MERCK SHARP & DOHME CORP.
Reel/Frame 045561/0922 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2018
From: TUMMANAPALLI, SATYANARAYANA
To: ALBANY MOLECULAR RESEARCH INC.
Reel/Frame 045562/0045 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2018
From: ALBANY MOLECULAR RESEARCH, INC.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 045562/0229 →