Back to results
US 6,211,197 B1Granted
Prostaglandin receptor ligands
AssigneeMerck Frosst Canada, Inc.
InventorsMichel Belley, Marc Labelle, Nicholas Lachance, Michel Gallant, Nathalie Chauret, Laird A. Trimble, Chun Li
Life of this patent
Estimating the term…
Abstract
Compounds and methods for treating prostaglandin mediated diseases, and certain pharmaceutical compositions thereof are disclosed. The compounds are represented by formula II: Ar1—W—Ar2—X—Q II The compounds of the invention are structurally different from NSAIDs and opiates, and are antagonists of the pain and inflammatory effects of E-type prostaglandins.
Claims12
A compound represented by formula II:
- Ar1—W—Ar2—X—Q II
- or a pharmaceutically acceptable salt or hydrate thereof, wherein:
- Ar1 is benzene, naphthalene, benzofuran or methylenedioxyphenyl, optionally substituted by R1 and R3;
- R1 is OH, OCH2Ar3, SCH2Ar3, OAr3, SAr3 or NR2CH2Ar3;
- R3 is R4, halogen, haloC1-6alkyl, N(R5)2, CN, NO2, C(R6)3, CON(R5)2, OR4, SR4 or S(O)nR7;
- R4 is H, lower alkyl, lower alkenyl, lower alkynyl, CHF2 or CF3;
- R5 is R4, Ph or Bn, or two R5 groups in combination with the atom to which they are attached represent a ring of up to 6 members containing carbon atoms and up to 2 heteroatoms selected from O, N and S;
- R6 is H, F, CF3 or lower alkyl, or two R6 groups may be taken together and represent a ring of up to 6 members containing carbon atoms and 0-2 heteroatoms selected from O, N and S;
- R7 is lower alkyl, lower alkenyl, lower alkynyl, CHF2, CF3, N(R5)2, Ph(R8)2 or CH2Ph(R8)2;
- R8 is R4, OR4, SR4 or halogen;
- Ar3 is selected from the group consisting of benzene, pyridine, thiophene, furan, oxazole and thiazole, said group being optionally substituted with R3;
- Ar2 is benzene, optionally substituted with 1-4 members selected from the group consisting of:
- R4, OR4, SR4 and halogen;
- W is selected from the group consisting of:
- CH2OCH2, (CH2)3, CH2CH═CH, CH═CHCH2, CH(OH)CH═CH, CH═CHCH(OH), CH2C≡C, C≡CCH2 1,2-c-Pr—CH2— and —CH2-1,2-c-Pr—;
- X represents a linker which is attached to Ar2 ortho to the attachment of W and is selected from the group consisting of:
- (CH2)2, CH═CH, C≡C and 1,2-c-Pr;
- and Q is CO2H or tetrazole.
15 more elements
A compound represented by formula II:
- Ar1—W—Ar2—X—Q II
- or a pharmaceutically acceptable salt or hydrate thereof, wherein:
- Ar1 is benzene, naphthalene, benzofuran or methylenedioxyphenyl, optionally substituted with R1 and R3;
- R1 is OH, OCH2Ar3, SCH2Ar3, OAr3, SAr3 or NR2CH2Ar3;
- R3 is R4, halogen, haloC1-6alkyl, N(R5)2, CN, NO2, C(R6)3, CON(R5)2, OR4, SR4 or S(O)nR7;
- R4 is H, lower alkyl, lower alkenyl, lower alkynyl, CHF2 or CF3;
- R5 is R4, Ph or Bn, or two R5 groups in combination with the atom to which they are attached represent a ring of up to 6 members containing carbon atoms and up to 2 heteroatoms selected from O, N and S;
- R6 is H, F, CF3 or lower alkyl, or two R6 groups may be taken together and represent a ring of up to 6 members containing carbon atoms and 0-2 heteroatoms selected from O, N and S;
- R7 is lower alkyl, lower alkenyl, lower alkynyl, CHF2, CF3, N(R5)2, Ph(R8)2 or CH2Ph(R8)2;
- R8 is R4, OR4, SR4 or halogen;
- Ar3 represents a member selected from the group consisting of:
- benzene, pyridine, thiophene, furan, oxazole or thiazole, said group being optionally substituted with R3;
- W is selected from the group consisting of:
- CH2OCH2, (CH2)3, CH2CH═CH, CH═CHCH2, CH(OH)CH═CH, CH═CHCH(OH), CH2C≡C or C≡CCH2;
- Ar2 is benzene, optionally substituted with R8;
- X represents a linker which is attached to Ar2 ortho to the attachment of W and is selected from the group consisting of:
- (CH2)2, CH═CH, C≡C and 1,2-c-Pr;
- Q is CONHSO2ZAr4;
- Z is a 0-2 carbon linker and is unsubstituted;
- Ar4 is selected from the group consisting of:
- benzene, pyridine, thiophene, furan, oxazole, thiazole, 1,3,4-thiadiazole and naphthalene, and is optionally substituted by R3.
18 more elements
A compound falling withing the following table:
- TABLE I (Ar1—W—Ar2—X—Q) Ex Ar1 W Ar2 X Q 1 2-(BnO)-3-MePh (CH2)3 1,2-Phe (CH2)2 CO2H 2 2-(BnO)-3-MePh CH2CH═CH 1,2-Phe CH═CH CONHSO2-2- thienyl 3 2-(BnO)-3-MePh CH═CHCH2 1,2-Phe CH═CH CONHSO2-2- thienyl 4 2-((2-Cl-4-FPh)CH2O)- CH2CH═CH 1,2-Phe CH═CH CO2H 3-CF3Ph 5 2-((2-Cl-4-FPh)CH2O)- CH═CHCH2 1,2-Phe CH═CH CO2H 3-CF3Ph 6 2-(BnO)Ph CH2CH═CH 1,2-Phe CH═CH CO2−X+ 7 2-(BnO)Ph CH═CHCH2 1,2-Phe CH═CH CO2−X+ 8 4-(BnO)-3,5-(MeO)2Ph CH2CH═CH 1,2-Phe CH═CH CO2−X+ 9 4-(BnO)-3,5-(MeO)2Ph CH═CHCH2 1,2-Phe CH═CH CO2−X+ 10 2-(BnO)-5-AcPh CH2CH═CH 1,2-Phe CH═CH CO2H 11 2-(BnO)-5-AcPh CH═CHCH2 1,2-Phe CH═CH CO2H 12 2-(BnO)-3-(MeO)Ph CH2CH═CH 1,2-Phe CH═CH CO2−X+ 13 2-(BnO)-3-(MeO)Ph CH═CHCH2 1,2-Phe CH═CH CO2−X+ 14 4-(BnO)-3-(MeO)Ph CH2CH═CH 1,2-Phe CH═CH CO2−X+ 15 4-(BnO)-3-(MeO)Ph CH═CHCH2 1,2-Phe CH═CH CO2−X+ 16 2-(BnO O)-3-MePh CH2CH═CH 1,2-Phe CH2 CO2−X+ 17 2-(BnO)-3-MePh CH═CHCH2 1,2-Phe CH2 CO2−X+ 18 2-(BnO)-3-MePh CH2CH═CH 5-Cl-1,2-Phe CH2 CO2−X+ 19 2-(BnO)-3-MePh CH═CHCH2 5-Cl-1,2-Phe CH2 CO2-X+ 20 4-(BnO)-3-(MeO)Ph (CH2)3 1,2-Phe 1,2-c-Pr CO2H 21 2-(BnO)-3-MePh CH═CHCH2 4,5-(MeO)2- CH═CH CO2H 1,2-Phe 22 2-(BnO)-3-MePh CH2CH═CH 4,5-(MeO)2- CH═CH CO2H 1,2-Phe 23 3,4-(methylene CH═CHCH2 1,2-Phe CH═CH CO2H dioxy)Ph 24 3,4-(methylene CH2CH═CH 1,2-Phe CH═CH CO2H dioxy)Ph 25 Ph CH═CHCH2 1,2-Phe CH═CH CO2H 26 Ph CH2CH═CH 1,2-Phe CH═CH CO2H 27 2-(HO)-3-MePh CH═CHCH2 1,2-Phe CH═CH CO2H 28 2-(BnO)-3-MePh CH═CHCH2 1,2-Phe CH═CH CO2−X+ 29 2-(BnO)-3-MePh CH2CH═CH 1,2-Phe CH═CH CO2−X+ 30 2-((7-Cl-2- CH═CHCH2 1,2-Phe CH═CH CO2H quinolinyl)CH2O)-3- MePh 31 2-((7-Cl-2- CH2CH═CH 1,2-Phe CH═CH CO2H quinolinyl)CH2O)-3- MePh 32 2-(BnO)-3-MePh (CH2)3 1,2-Phe bond CO2H 33 2-(BnO)-3-MePh CH═CHCH2 1,2-Phe bond CO2−X+ 34 2-(BnO)-3-MePh CH2CH═CH 1,2-Phe bond CO2−X+ 35 2-(BnO)-3-MePh (CH2)3 1,2-Phe CH═CH CO2−X+ 36 2-(BnO)-3-(MeO)Ph (CH2)3 1,2-Phe CH═CH CO2−X+ 37 4-(BnO)-3-(MeO)Ph (CH2)3 1,2-Phe CH═CH CO2−X+ 38 4-(MeO)Ph CH2CH═CH 1,2-Phe CH═CH CO2H 39 4-(MeO)Ph CH═CHCH2 1,2-Phe CH═CH CO2H 40 3,4-(MeO)2Ph CH2CH═CH 1,2-Phe CH═CH CO2H 41 3,4-(MeO)2Ph CH═CHCH2 1,2-Phe CH═CH CO2H 42 2-(BnO)Ph CH(OH)CH═CH 1,2-Phe CH═CH CO2−X+ 43 2-(BnO)-3-MePh (CH2)3 1,2-Phe (CH2)2 CON−X+ SO2-2- thienyl 44 4-(BnO)-3-(MeO)Ph CH2CH═CH 1,2-Phe CH═CH CON−X+ SO2-2- thienyl 45 4-(BnO)-3-(MeO)Ph CH═CHCH2 1,2-Phe CH═CH CON−X+ SO2-2- thienyl 46 2-(BnO)-3-MePh CH2-1,2-c-Pr 1,2-Phe CH═CH CO2−X+ 47 2-(BnO)-3-MePh 1,2-c-Pr-CH2 1,2-Phe CH═CH CO2−X+ 48 2-(BnO)-3-MePh CH(OH)CH═CH 1,2-Phe CH═CH CO2−X+ 49 2-(BnO)-3-MePh CH═CHCH(OH) 1,2-Phe CH═CH CO2H 50 2-((2,6-Cl2Ph)CH2O)- CH═CHCH(OH) 1,2-Phe CH═CH CO2H 3-MePh 51 2-((2,6-Cl2Ph)CH2O)- CH(OH)CH═CH 1,2-Phe CH═CH CO2H 3-MePh 52 2-((4-FPh)CH2O)-3- CH2CH═CH 1,2-Phe CH═CH CO2H MePh 53 2-((4-FPh)CH2O)-3- CH═CHCH2 1,2-Phe CH═CH CO2−X+ MePh 54 2-((3,4-F2Ph)CH2O)- CH2CH═CH 1,2-Phe CH═CH CO2H 3-MePh 55 2-((3,4-F2Ph)CH2O)- CH═CHCH2 1,2-Phe CH═CH CO2−X+ 3-MePh 56 2-((3,5-F2Ph)CH2O)- CH2CH═CH 1,2-Phe CH═CH CO2H 3-MePh 57 2-((3,5-F2Ph)CH2O)- CH═CHCH2 1,2-Phe CH═CH CO2−X+ 3-MePh 58 2-((2,6-Cl2Ph)CH2O)- CH2CH═CH 1,2-Phe CH═CH CO2H 3-(HOCH2)Ph 59 2-((2,6-Cl2Ph)CH2O)- CH═CHCH2 1,2-Phe CH═CH CO2H 3-(HOCH2)Ph 60 2-((2,6-Cl2Ph)CH2O)- CH2CH═CH 1,2-Phe CH═CH CO2H 3-MePh 61 2-((2,6-Cl2Ph)CH2O)- CH═CHCH2 1,2-Phe CH═CH CO2−X+ 3-MePh 62 2-((4-CF3Ph)CH2O)- CH2CH═CH 1,2-Phe CH═CH CO2H 3-MePh 63 2-((4-CF3Ph)CH2O)- CH═CHCH2 1,2-Phe CH═CH CO2−X+ 3-MePh 64 2-((4-(CHF2O)Ph) CH2CH═CH 1,2-Phe CH═CH CO2H CH2O)-3-MePh 65 2-((4-(CHF2O)Ph) CH═CHCH2 1,2-Phe CH═CH CO2−X+ CH2O)-3-MePh 66 2-((4-CF3Ph)CH2O)- CH═CHCH(OH) 1,2-Phe CH═CH CO2H 3-(HOCH2)Ph 67 2-((4-CF3Ph)CH2O)- CH═CHCH2 1,2-Phe CH═CH CO2H 3-(HOCH2)Ph 68 2-((4-CF3Ph)CH2O)- CH═CHCH(OH) 1,2-Phe CH═CH CO2H 3-MePh 69 2-(PhCH2O)-3- CH═CHCH2 1,2-Phe CH═CH CO2H (HOCH2)Ph 70 3-(PhO)Ph CH2OCH2 1,2-Phe CH═CH CO2−X+ 71 2-(PhO)Ph CH2OCH2 1,2-Phe CH═CH CO2−X+ 72 3-(BnO)Ph CH2CH═CH 1,2-Phe CH═CH CO2−X+ 73 3-(BnO)Ph CH═CHCH2 1,2-Phe CH═CH CO2−X+ 74 2-(BnO)Ph O(CH2)3O 1,2-Phe CH═CH CO2−X+ 75 2-(PhCHMeO)-3- CH═CHCH2 1,2-Phe CH═CH CO2−X+ MePh 76 2-(PhCHMeO)-3- CH2CH═CH 1,2-Phe CH═CH CO2H MePh 77 3-(PhO)Ph CH═CHCH2 1,2-Phe CH═CH CO2−X+ 78 3-(PhO)Ph CH2CH═CH 1,2-Phe CH═CH CO2−X+ 79 3-Phbenzofuran-7-yl CH═CHCH2 1,2-Phe CH═CH CO2−X+ 80 3-Phbenzofuran-7-yl CH2CH═CH 1,2-Phe CH═CH CO2−X+ 81 Ph CH═CHCH2 1,2-Phe CH═CH CONHSO2- 2-thienyl 82 Ph CH2CH═CH 1,2-Phe CH═CH CONHSO2- 2-thienyl 83 4-(MeO)Ph CH═CHCH2 1,2-Phe CH═CH CONHSO2-2- thienyl 84 4-(MeO)Ph CH2CH═CH 1,2-Phe CH═CH CONHSO2-2- thienyl 85 2-(BnO)-1-naphthyl CH2NHCO 1,2-Phe CH═CH CO2H 86 2-((2-Cl-4-FPh) CH2CH═CH 1,2-Phe CH═CH CO2H CH2O)-3-MePh 87 2-((2-Cl-4-FPh) CH═CHCH2 1,2-Phe CH═CH CO2H CH2O)-3-MePh 88 2-((2,4-F2Ph)CH2O)- CH2CH═CH 1,2-Phe CH═CH CO2H 3-MePh 89 2-((2,4-F2Ph) CH═CHCH2 1,2-Phe CH═CH CO2H CH2O)-3-MePh 90 2-((2,4,6-F3Ph) CH2CH═CH 1,2-Phe CH═CH CO2H CH2O)-3-MePh 91 2-((2,4,6-F3Ph) CH═CHCH2 1,2-Phe CH═CH CO2H CH2O)-3-MePh 92 2-((2,6-Cl2-4-FPh) CH2CH═CH 1,2-Phe CH═CH CO2H CH2O)-3-MePh 93 2-((2,6-Cl2-4-FPh) CH═CHCH2 1,2-Phe CH═CH CO2H CH2O)-3-MePh 94 2-((2,4-F2Ph)CH2O)- CH2CH═CH 1,2-Phe CH═CH CO2H 3-(CHF2O)Ph 95 2-((2,4-F2Ph)CH2O)- CH═CHCH2 1,2-Phe CH═CH CO2H 3-(CHF2O)Ph 96 2-((4-FPh)CH2O)- CF2CH═CH 1,2-Phe CH═CH CO2H 3-MePh 97 2-((4-FPh)CH2O)- CH═CHCF2 1,2-Phe CH═CH CO2H 3-MePh 98 2-((4-FPh)CH2O)- (CH2)3 1,2-Phe CH═CH CONHSO2- 3-MePh (4-i-PrPh) 99 2-((4-FPh)CH2O)- (CH2)3 1,2-Phe CH═CH CONHSO2- 3-MePh (4-t-BuPh) 100 2-((4-FPh)CH2O)- CH2CH═CH 1,2-Phe CH═CH CONHSO2- 3-MePh (4-(MeO)Ph) 101 2-((4-FPh)CH2O)- CH═CHCH2 1,2-Phe CH═CH CONHSO2- 3-MePh (2,3-Cl2Ph) 102 2-((4-FPh)CH2O)- CH═CHCH2 4-Cl-1,2-Phe CH═CH CONHSO2- 3-MePh (5-Br-2- (MeO)Ph) 103 2-((4-FPh)CH2O)- (CH2)2S 3-F-1,2-Phe CH═CH CONHSO2- 3-MePh (2,3,4-Cl3Ph) 104 2-((4-FPh)CH2O)-3- (CH2)2S 6-CF3-1,2- CH═CH CONHSO2- MePh Phe (5-F-2-MePh) 105 2-((4-FPh)CH2O)-3- (CH2)2S 4,5-F2-1,2- CH═CH CONHSO2- MePh Ph (2,5-Me2Ph) 106 2-((4-FPh)CH2O)-3- (CH2)2SO2 1,2-Phe CH═CH CONHSO2- MePh (4-CF3Ph) 107 2-((4-FPh)CH2O)-3- (CH2)2SO2 1,2-Phe CH═CH CONHSO2-2- MePh naphthyl 108 2-((4-FPh)CH2O)-3- CH═CHCH2 3-F-1,2-Phe CH═CH CONHSO2- MePh (3-Cl-4-FPh) 109 2-((4-FPh)CH2O)-3- SO2(CH2)2 1,2-Phe CH═CH CONHSO2- MePh (4-n-PrPh) 110 2-((4-FPh)CH2O)-3- SO2(CH2)2 1,2-Phe CH═CH CONHSO2- (MeO)Ph (2-ClPh) 111 2-((4-FPh)CH2O)-3- SO2(CH2)2 1,2-Phe CH═CH CONHSO2- (MeO)Ph (4-FPh) 112 2-((4-FPh)CH2O)-3- S(CH2)2 1,2-Phe CH═CH CONHSO2- (MeO)Ph (2-PhPh) 113 2-((4-FPh)CH2O)-3- S(CH2)2 1,2-Phe CH═CH CONHSO2- (MeO)Ph (2-CF3Ph) 114 2-((4-FPh)CH2O)-3- S(CH2)2 4-t-Bu-1,2- CH═CH CONHSO2- (MeO)Ph Phe (4-Cl-2,5- Me2Ph) 115 2-((4-FPh)CH2O)-3- O(CH2)2 1,2-Phe CH═CH CONHSO2- (MeO)Ph (2,5-Cl2Ph) 116 2-((4-FPh)CH2O)-3- O(CH2)2 1,2-Phe CH═CH CONHSO2- (MeO)Ph (4-Br-2- (CF3O)Ph) 117 2-((4-FPh)CH2O)-3- O(CH2)2 1,2-Phe CH═CH CONHSO2- (MeO)Ph CH2Ph 118 2-((4-FPh)CH2O)-3- (CH2)2O 1,2-Phe CH═CH CONHSO2-1- (MeO)Ph naphthyl 119 2-((4-FPh)CH2O)-3- (CH2)2O 4,5-F2-1,2- CH═CH CONHSO2- (MeO)Ph Phe (2-FPh) 120 2-((4-FPh)CH2O)-3- (CH2)2O 1,2-Phe CH═CH CONHSO2- (MeO)Ph (2,4-Cl2Ph) 121 2-((4-FPh)CH2O)-3- (CH2)3 1,2-Phe CH═CH CONHSO2- (MeO)Ph CH═CHPh 122 2-((4-FPh)CH2O)-3- (CH2)3 1,2-Phe CH═CH CONHSO2- (MeO)Ph (3,5- (CF3)2Ph) 123 2-((4-FPh)CH2O)Ph (CH2)3 1,2-Phe CH═CH CONHSO2- (2,5-Cl2-3- thienyl) 124 2-((4-FPh)CH2O)Ph (CH2)4 3-F-1,2-Phe CH═CH CONHSO2- (3-BrPh) 125 2-((4-FPh)CH2O)Ph (CH2)4 3-MeO-1,2- CH═CH CONHSO2- Phe (2-BrPh) 126 2-((4-FPh)CH2O)Ph (CH2)4 1,2-Phe CH═CH CONHSO2- (2-NO2Ph) 127 2-((4-FPh)CH2O)Ph (CH2)5 1,2-Phe (CH2)2 CONHSO2- (3-ClPh) 128 2-((4-FPh)CH2O)Ph (CH2)5 1,2-Phe (CH2)2 CONHSO2- (4-(CF3O)Ph) 129 2-HOPh CH═CH(CH2)2 1,2-Phe (CH2)2 CONHSO2-8- quinolinyl 130 2-((4-FPh)CH2O)Ph CH═CH(CH2)2 5-(CF3O)- (CH2)2 CONHSO2- 1,2-Phe (3,4-Cl2Ph) 131 4-((2,6-Cl2-4- CH═CH(CH2)2 3-F-1,2-Phe (CH2)2 CONHSO2- FPh)CH2O)-3-MePh (4-EtPh) 132 2-((4-FPh)CH2O)Ph CH2CH═CH 1,2-Phe (CH2)2 CONHSO2- (4-Cl-2- NO2Ph) 133 2-((4-FPh)CH2O)Ph CH═CHCH2 4,5-F2-1,2- CH═CH CONHSO2- Phe (2-Cl-3-Br-5- thienyl) 134 2-((4-FPh)CH2O)Ph CH2CH═CH 4,5-F2-1,2- CH═CH CONHSO2- Phe (3,4- (MeO)2Ph) 135 2-HOPh CH═CHCH2 4,5-F2-1,2- CH═CH CONHSO2- Phe (2,5-Cl2-3-Br- 4-thienyl) 136 4-((4-FPh)CH2O)-3- CH2CH═CH 4,5-F2-1,2- CH═CH CONHSO2- (MeO)Ph Phe (4-Br-2,5- F2Ph) 137 4-((4-FPh)CH2O)-3- CH═CHCH2 1,2-Phe CH═CH CONHSO2- (MeO)Ph (5-(AcNH)- 1,3,4- thiadiazol-2-yl) 138 4-((4-FPh)CH2O)-3- CH2CH═CH 1,2-Phe CH═CH CONHSO2- (MeO)Ph (2,3,4,5,6- F5Ph) 139 4-((2-Cl-4-FPh)CH2O)- CH═CHCH2 1,2-Phe CH═CH CONHSO2- 3-MePh (2-CNPh)2 140 2-((4-FPh)CH2O)Ph CH2CH═CH 4-F-1,2-Phe CH═CH CONHSO2- (2-Cl-6- MePh) 141 2-HOPh CH═CHCH2 1,2-Phe CH═CH CONHSO2- (2,4,6- Me3Ph) 142 Ph CH2CH═CH 1,2-Phe CH═CH CONHSO2- (2,3-Br2-2- thienyl) 143 2-((4-FPh) CH═CHCH2 1,2-Phe CH2O CONHSO2- CH2O)Ph (4-NO2Ph) 144 2-((4-FPh) CH2CH═CH 1,2-Phe CH2O CONHSO2- CH2O)Ph (3,5-Cl2Ph) 145 2,4-((4-FPh) CH═CHCH2 1,2-Phe prop-1- CONHSO2- CH2O)2Ph yne-1,3- (5-Cl-2- diyl thienyl) 146 4-((2,4-F2Ph)CH2O)- CH2CH═CH 1,2-Phe CH2O CONHSO2- 3-(MeO)Ph (4-CF3Ph) 147 2-HO-3-MePh CH═CHCH2 1,2-Phe CH2O CONHSO2- (2,4-F2Ph) 148 2-((4-FPh)CH2O)Ph CH2CH═CH 4-F-1,2-Phe 1,2- CONHSO2- ethyne (4-ClPh) diyl 149 2-((4-FPh)CH2O)Ph CH═CHCH2 1,2-Phe 1,2- CONHSO2- ethyne (3-CF3Ph) diyl 150 4-HOPh CH2CH═CH 1,2-Phe 1,2- CONHSO2- ethyne Ph diyl 151 2-((4-FPh) CH═CHCH2 1,2-Phe prop-2- CONHSO2- CH2O)Ph yne-1,3- (5-Br-2- diyl thienyl) 152 2,4-((4-FPh) CH2CH═CH 1,2-Phe 1,2- CONHSO2- CH2O)2Ph ethynediyl Me 153 2,4-((4-FPh) CH═CHCH2 1,2-Phe 1,2-c-Pr CONHSO2- CH2O)2Ph (2,5- (MeO)2Ph) 154 6-((4-FPh)CH2O)- CH2CH═CH 4-F-1,2-Phe 1,2-c-Pr CONHSO2- 2-naphthyl (3-MePh) 155 2-((4-FPh) CH═CHCH2 1,2-Phe 1,2-c-Pr CONHSO2- CH2O)Ph (4-MePh) 156 4-HO-3-(MeO)Ph CH2CH═CH 1,2-Phe 1,2-c-Pr CONHSO2-n- Bu 157 4-((4-FPh)CH2O)- CH═CHCH2 1,2-Phe 1,2-c-Bu CONHSO2- 1-naphthyl (2-Cl-4-FPh) 158 Ph CH2CH═CH 1,2-Phe CH═CH CONHSO2- (2-MePh) 159 2-((4-FPh) CH═CHCH2 1,2-Phe CH═CH CONHSO2- CH2O)Ph c-Pr 160 2,4-((4-FPh) CH═CHCH2 1,2-Phe CH═CH CO2H CH2O)2Ph 161 4-((2,4-F2Ph) (CH2)3 4-F-1,2-Phe CH═CH 1H-Tetrazol- CH2O)-3-(MeO)Ph 5-yl 162 2-((4-FPh) CH═CHCH2 3-MeO- CH═CH 1H-tetrazol- CH2O)Ph 1,2-Phe 5-yl 163 2,4-((4-FPh) CH═CHCH2 1,2-Phe CH═CH 1H-tetrazol- CH2O)2Ph 5-yl 164 4-HO-3-(MeO)Ph CH═CHCH2 1,2-Phe 1,2-c-Pr 1H-tetrazol- 5-yl 165 Ph CH═CHCH2 1,2-Phe (CH2)2 1H-tetrazol- 5-yl 166 2-((4-FPh)CH2O)- CH═CHCH2 1,2-Phe CH═CH SO3H 3-(MeO)Ph 167 2-((4-FPh)CH2O)- (CH2)3 4-F-1,2-Phe (CH2)2 SO3H 3-MePh
- wherein X+ represents a cation.
Dependencies are inferred from the claim text.